A new day

It's sunday and i'm bored. Can't wait 'till tomorrow so that I can be away from the she-devil in my house. It will be welcome relief.

What do your think?

I feel good about that last post. I would like some feedback so i can tweak my writing style a little.

You wish you could do this. An Original Story.

Evelyn moved into town taking over a class while the teacher was away having a baby. No one knew her and she would be moving on at the end of the year so she felt confident consulting a local surgeon for cosmetic surgery after dreaming for some time of having her small breasts enlarged.

Every onerous task had been completed at the end of the school year so from now on every hour would be her own time or so she thought.

Andrew left high school that year without the expected results and nursed a grudge against his tutor. Working at the hospital as a penance, imposed by his father for the poor results, he discovered her little secret.

Breaking into the hospital computer he changed the consultant's notes for her surgery, adding some little adjustments. Each day he made some changes becoming carried away with the game.

Eventually a complete new identity had been built to justify the new body shape until she was no longer a teacher but a porn star from California.

As the date came round for her surgery he realized he had gone too far and signed on to change everything back to what it had originally specified.

"Damn! They've changed the password." He said to himself. Trying the administrators and everyone's in the office didn't help, the records were locked down.

He laughed to himself. "It won't be done. It's too ridiculous. The consultant will see they have been changed and put them right." He sighed to himself, only half convinced. He sat for awhile wondering if the changes could be traced back to him.

The consultant was too busy to meet and greet Evelyn before surgery as an important golf game had come up organized by a pharmaceutical company. It was just a routine case so the surgeon would take care of things from the notes.

***

Miss Evelyn Simpson awoke to find herself still bandaged but no longer in hospital. She lay there wondering where she was for this wasn't her apartment either.

The door opened and a young man walked in. In a befuddled state she didn't recognize him as one of her students.

"So you are awake at last. You had better take this it's the last of your pills. The hospital gave you." Andrew told her.

"What are you doing here?" She asked. Her mouth was dry and she felt so tired it was difficult to concentrate.

"This is my parent's house. The hospital phoned to come and pick you up. Don't you remember?" Andrew said.

She shook her head and regretted it. The room span around causing her to feel sick. "Why would the hospital phone you?" She asked.

"There was an emergency, a big crash on the freeway, and they needed all the beds in your ward. You must have had their number in your purse or written the wrong number in the notes. Any way they collected you and brought you here. You were about to be discharged anyway." He lied.

Andrew had finally cracked the computer password after the surgery. He had been in a panic for the consultant would be looking in on her yesterday afternoon. He upped the date for discharge and added that her brother was collecting her.

Yesterday morning was fraught with danger as he collected his teacher from hospital, expecting any moment to be found out.

In a daze Evelyn let the nurse wheel her out to his car. "I don't think she should be going home just yet despite what the notes say." The nurse told him. "I'll phone the consultant."

"It's OK. Mom is a nurse and she's worked post surgery for years. She'll look after sis." Andrew said, hoping awkward questions wouldn't be asked.

The nurse was called away just in time. He signed the papers and a young nurse who didn't seem to care if the patient was dead or alive wheeled her out.

"Here take this and you'll be fine." He told her.

She swallowed the pill then thought to ask what it was. He told her it was a sleeping pill but she was already drifting off.

***

Sitting beside the bed reading a book he watched her eyes flicker open. "I'm Andrew remember me telling you yesterday?" he asked.

"Yes, I remember now, Andrew from my class. Was it yesterday? Have I been out of it a whole day? Can you call your mother for me?" She asked.

"She's away. They went away to Europe for a few weeks." He said. Not adding he would have gone with them if she had tutored him better this last year.

"Who's been looking after me then?" She said in surprise.

"I have. Since you arrived I've been looking after you." He told her, expecting some thanks.

The implications started to sink in. "But what about. I mean, how did I get to the bathroom?"

"I managed to get you to the bathroom eventually. I changed the sheets once and you used a bed pan once." He told her sourly. He hadn't anticipated that in his plan at all.

Looking a embarrassed at the idea of it she nevertheless bowed to the inevitable. "I'm sorry but I need to go. I need help to get there." She said raising an arm for him to hold onto. It wasn't enough he had to wrap his arms around her and lift.

With one arm around her they managed to shuffle there. "The hospital shouldn't have let you take me away. Your not family your one of my pupils. What happened, how did this happen?" She asked. Although there was no one else she knew in this town it was improper for a young man to be looking after her in this helpless state.

"An administration fault I guess." He didn't add he had seen plenty of errors for he dare not reveal he had worked there.

Unable to even lift the loose shift covering her naked body she asked him for help. Unable to wait until he left she suddenly let loose a hot stream into the pan. Without a chance to stop him he unexpectedly wiped her between the legs with a tissue. So embarrassed was she her mouth flapped without a word leaving her throat.

On the away back to bed she wondered what he had done to her last night. Back in bed she was so exhausted she lay their supine nodding off to sleep. He began to sponge her down without protest not having the strength to stop him.

On waking later she felt more refreshed for the sleeping pills had started to wear off. She was hungry and the appetite ruled her head as she tucked into a bowl of soup.

"Its delicious, it's home made isn't it. And this Cabata is gorgeous."

"

I'll get rid of these crumbs then get you another drink." He told her.

W

ith the sheets off the bed she watched him shake them but was surprised when he laid them on the floor. With a little anxiety she watched him squeeze out a cloth and sponge. She didn't know what to say but lay there feeling vulnerable and embarrassed. He had obviously done this a few times before.

After all, the bandages seemed to protect her person more than a bikini would at the beach. His touch was soothing and she especially liked it when he massaged her back. Up until then she had only been faintly aware of what he was doing to her with the drugs keeping her compliant.

This was different, she was fully awake and it seemed wrong. Nice, but wrong for one of her students to be bathing her in bed.

"I need to go to the bathroom. Do you mind giving me a lift out of bed? I can make it the rest of the way." She stated, trying to sound confident.

She leaned on him to the bathroom but thankfully managed by herself once there. On the way back from the toilet she stopped before a mirror, which had been deliberately uncovered for her to notice the bandages.

He had become impatient wanting to unveil the new Miss Evelyn Simpson. Looking at herself in the mirror she asked. "Why are there so many bandages over my body? Surely they should have just covered my, I mean just the one set."

"Let's get back to your room. We can look at the notes." He said. Sitting on a chair out of reach he read out the notes that he had tampered with just a couple of weeks ago. The expected operation was read out only he didn't mention their new dimensions. He softened his voice feeling guilty.

"The waist has been reduced. The thighs reduced too"

She looked at him still unsure of what was going on, not wanting to believe it.

"Are you sure?" She asked. "There must have been some mistake. All I wanted. Well you know now." She said.

"I had better check my body with those notes and see what the hell those idiots have been up to. You can help with these bandages." Privacy gave way to expediency for she was intent on finding out what they had done to her.

He helped roll the bandages away from her torso as she couldn't manage them. Not caring that he was stripping her naked she just wanted to see what had been done to her figure.

He helped her up off the bed to stand before a mirror.

Supported by him she looked in amazement at this new body that hardly looked real. "It's a mistake, surely." She whispered.

Her breasts had implants inserted as she had wanted only they were huge. She noticed a scar under both ribs where the waist had been reduced to an extraordinary degree. Her breasts were sculpted massive over the tiny waist. Her body looked out of proportion like some bizarre doll.

Her thighs had been reduced which was something else she hadn't asked for. Her legs looked long and thin unable to support the top heavy figure.

He helped her into bed while she asked in a daze. "What happened? This is not what I discussed with the consultant."

She was not listening to him as he explained quietly what had been done.

Slowly taking in what he was saying brought her thoughts to a terrible realization.

Looking in horror across the room she asked. "You brought me here. What? What have you done to me? What have you done to my body? It's ridiculous! You've turned me into a cartoon character."

The obvious look of guilt upon his face as he turned away from her confirmed it. Suddenly suspicious she asked. "Did you? Did you do anything else?" She stared across the room at him taking in the look of his shame and just knew there was more.

"What aren't you telling me? Tell me." She pleaded. "Please, just tell me." She said. He picked up the notes, although he didn't need them as a reminder of the little extra changes.

"Several other things were done. Your lips have been enlarged and inside you have been reduced."

She quickly put her fingers to her face but knew there had been no changes there. Looking down between her legs she put a hand there and in a small voice she said. "These lips down here?" He nodded. Struggling to speak she said. "Inside has been reduced?" Again he nodded.

"What else was change?" He looked away to reply very softly.

"The anus has been enlarged." She looked across the room not seeing him.

She started to speak very quietly, her voice rising to a shriek. "What do you mean 'the' anus? You mean 'my' anus has been enlarged. You've had MY anus enlarged. What for? Of what use is my anus to you. Do you have plans to use it? Oh! I see." She sat looking even paler than she had been.

Her face glowed with rage becoming red with rage; her hands were balled into tight fists as she began again quietly building to a shriek.

"My breasts have been enlarged for you. My vagina has been tightened for you. My anus made looser for you. You bastard! I'm not a cartoon character but a plaything. I'm a sex doll. You've made me into your private sex doll. This is what you've done; you've turned your teacher into a sex object. The options you chose for me are those that a common whore would have done to her. I'm a slut whose body is shaped for men to use more easily. That's what you've done to me, you idiot!

You've made me into a slut. You've changed me from a decent respectable teacher into a real low down whore." She bellowed at him.

Andrew didn't know where to look he just wanted to run. This is not what he had planned at all. A little revenge had turned into a nightmare, for them both. He saw that now but it was too late.

"This is my body. It's mine, do you understand? These ridiculous things are my breasts." She said wrapping her arms around them. She had to stretch her arms out they were so huge. The enormity of her situation hadn't sunk in but already it was threatening to overwhelm her.

He watched her fingers grip her breasts and unavoidably touch the enlarged nipples. "I wouldn't do that if I were you." He warned her.

"I told you they are mine not your play things." She shouted at him. As though to demonstrate they belonged to her she squeezed the nipples.

He watched her face change from rage to curiosity. She blinked several times with her head on one side as though listening for something. She shook her head trying to clear it of some misunderstood message.

She seemed to grow restless as though too hot and was finding the room constricting. She opened her legs a little wanting to cool her body.

She spread her legs wide in a lewd gesture. No longer shouting she glared at him intently.

Quietly she said. "Come on then Andrew. Use your new toy. Make use of your slut. You spent all that money on this body so it's yours now. It's not mine any more. It's bought and paid for, so just use it."

She continued sweetly in a dreamy voice. "Don't bother asking just help yourself. Just make use of it as you want. It's already prepared, so choose an orifice. Dip in anywhere you want." She said, becoming more agitated with every breath.

True to her word she became a slut helping and encouraging him to explore his sex doll. She pulled him onto the bed grappling with his trousers to extract his cock.

He was too afraid of her to be hard and so she sucked it into her mouth. It seemed like an adventure with a new intensity of sensations assaulting her mind.

She felt him grow hard and let go to kiss its head licking the wetness leaking there. She climbed onto him and positioned herself. With a low moan she felt his hardness crease her lips then plunged down on his hardness absorbing him into her vagina seeming to suck it in.

He lay there silent and still while she huffed and puffed up and down. He stared up at his teacher amazed at the sight of those huge breasts bouncing around.

'Shit!' He thought. 'My teachers fucking herself on my cock!' He began to move his hips thrusting up at her tight pussy unable to stop.

She experienced more intense feelings pushing her onward to fulfill a great overpowering need. She felt him coming but she wasn't ready and she cried out in fear.

When he flagged she renewed him with caresses to his cock and words of encouragement. "Please Andrew! I need your lovely cock inside me. Make me cum. Only you can fulfill me. I need you Andrew, please." She begged him.

She needed him to take her further, to take her again. She worked him so well with her mouth and throat he recovered quickly. Guiding him in to her body she rode him again. This time she moved her feet either side of his head to be penetrated so deep she could feel his cock hit the entrance to her womb.

It seemed to be an eternity before becoming sated. Her whole body shook with passion as the orgasm spread from between her legs. She had become so physically exhausted her body allowed her to rest with sleep taking over for a fretful dream.

She awoke suddenly both eyes wide with fear. He sat beside the bed looking at her. She peered at him over the new mounds that were her breasts. If they hadn't been hers she would have laughed at them.

"What happened? Did I dream it or did we just make love." She whispered. With anger flashing in her eyes she said. "I mean, did we have sex."

"Yes. I did try to warn you." He said in a flat voice. It was time to tell her the rest.

"What do you mean, 'warn me'."

She would guess soon enough so he cleared his throat and braced himself for another hysterical outburst. "Your nipples have been." He started then hesitated trying to gain the courage to tell her.

"There is an implant attached to your nipples. An experimental device, a miniature stimulator has been inserted behind each nipple." He said not daring to go on.

"What the hell are you talking about." She shouted.

"It sends an electrical signal, like a nerve would do, direct into the brain. Its connected to a pleasure centre or gland or something." He looked away unable to face her. It all seemed so terrible now she sat before him. He had thought of it as a prank not expecting it to really happen. Andrew tried to console himself with the excuse he had tried to reverse the notes but failed.

Evelyn sat dumbfounded. She suddenly threw her hands away from her body in fear. "I mustn't touch my nipples then." She stated.

The hysterical rant didn't materialize. He looked at her wondering if she had lost her mind.

"No one must touch them." He said quietly.

"What happened then was because I touched my nipples? The nipples, something implanted?" She asked. He nodded.

"It stimulates a gland to send a message to your brain and your body becomes hypersensitive needing to be sexually stimulated to orgasm. Touching the nipples sets it off." He said.

"No, don't touch them! You'll trigger it off again." He added quickly not able to face another onslaught upon his body.

She looked at the swollen nipples. They looked in proportion to the massive breasts yet hid a terrible secret. She was in shock with her mind trying to catch up.

"No!" She said in a little whimper of a voice. "You stupid little shit. You really have turned me into a sex doll. No! If I go out like this not only will I be stared at I'll be in real danger. Some stranger only has to touch my nipples and I'll be turned on, out of control. That's right isn't it? If my nipples are tweaked it turns me into a raving sex mad slut." She whispered.

He hadn't thought about how she would live her life like this. It had all just gradually evolved with him adding more and more modifications to her notes, a little more each day.

"Once the nipples have been gripped it starts the, err, it starts the process off. Then you will have to complete it." He said, trying to say it in as neutral way as possible.

She looked at him demanding his full attention. "Your telling me once my nipples have been squeezed the sexual stimulation won't stop until I have sex? No! It won't stop until I have an orgasm. Can't I control it? What have you done to me you stupid man?"

She sat rocking back and forth with her hands well away from her breasts.

"I'm a sex doll. Just switch me on and I'll perform." She murmured to herself while rocking back and forth, with an expression of shocked horror. "Now I know what's happening to me perhaps I can learn to control it." She said weakly.

Gasping loudly she whimpered with overwhelming emotion. She sat on the edge of the bed intently staring in the mirror at the stranger that her own body had become. She watched as the body clearly became excited, seeing the legs open, wanting to be explored more deeply.

He watched her eyes begin to glaze as she gripped the nipples gently squeezing them in a steady rhythm. She parted her legs and reached down between them. The hand dove between her lips to stimulate herself in a growing desperation.

Throwing her head back she moaned then reached out to him with both hands grasping tight.

Pulling his shorts to one side she fought in desperation to reach what was so desperately needed.

He fought her grip to slide off the bed out of reach, as she couldn't roll sideways in pursuit with those huge breasts.

"Come back. Please, let me have you. I need you." She cried out.

He reached under the bed and thrust a rubber dildo into her outreached hands that had been clawing the air for him. She perhaps mistook it for him but anyway thrust it in moving her whole body to its rhythm.

He moved between her outstretched legs maneuvering what was left of it into her ass.

At last the begging stopped to be replaced by a whimpering sound. So at last she was coming.

Her body collapsed on the bed, replete once more.

Knowing it wasn't her desire driving this vulgar behavior was both a relief and a terrible shock, especially with that lewd demonstration; it brought it home how deeply she was out of control. Feeling him remove the dildo from both her orifices she looked startled at what she had done to herself.

The thing was long and fat and she had greedily consumed it. Even now she wanted to hold onto it only his grip was stronger than hers. When it was finally dragged from her body she felt a sense of loss. Still under the influence of the orgasm a nasty thought crossed her mind, driven by a deep feeling of satisfaction, that it might not be so bad after all.

Shaking her head free of the alien thought she keenly kept her hands away from both nipples all the time intently staring at them in horror. Once more she slumped onto the bed feeling exhausted.

He looked at her thinking perhaps this was going to be too much for him. How could he possibly satisfy her if she were to play with her nipples again?

A sly grin crossed her face. "My! That was fantastic. I have never ever done anything like that before. I think I must have." She started to say, and then stopped. Not wanting to spill the sordid secret of how many orgasms she had experienced to him.

It was time to take back some control of the situation. "I must go home. Can you get me some clothes? I don't know what could possibly fit these huge things." She said.

"I paid off the lease for your apartment so there is no where to go. All your things are in storage. You should stay here. Besides, your bank account was wiped out paying for the surgery.

"You did what?" She asked not wanting to believe how her life had been turned upside down. "I can't go out like this! People will stare. I'm a freak. I certainly can't go to the next school looking like a Barbie doll. Now you tell me my savings are gone. I thought I could have these breasts reduced but I don't have the money. If there's anything else I'll kill you. She shouted at him.

***

It was dark when she awoke; coming too hoping it had all been a nightmare finding it was only too true she shivered in fright. Her whole world had changed. "I can't go out like this. What am I to do?" She said half to herself partly asking Andrew.

While she slept he had thought about what to do with her for it was patently obvious he wouldn't be able to cope with her by himself. It would take some time for him to come to terms with what he had done to her but he wasn't ready to tell her his plans, while she too was hardly ready to cope with the idea.

"I've nowhere to go and I can't go out looking for an apartment, even if I had the money, so it looks as though I have to stay here."

She looked at him meanly. "So, you have yourself a captive sex doll." She spat the words at him. "Do you realize what you have done to me? Where am I to get the money to undo this, this." She said waving her arms about her body careful not to touch it.

He moved to sit close to her meaning to comfort her.

"No! Don't touch me. Please. We will have to sort this mess out. You will have to help me, you must. Please!" She begged. 

A Wager Lost Ch. 5

I slept soundly that night. For the first half off the night, I don't think I moved from the position in which I'd crawled into bed. I do remember waking up though, about 2 or 3 in the morning, to use the bathroom and get a drink of water. Upon returning to bed, I drifted off into a sleep filled with vivid dreams...much like the night before. This time, instead of falling down Alice's rabbit hole, I dreamt that I sitting in a classroom full of students, and I was one of them. As I looked around, I noticed that there were men and women in the class, but we were all wearing school uniforms. The guys had on slacks, shirts, and ties, and the girls were wearing grey, pleated skirts, white blouses, knee-high white stockings, and black mary-jane shoes...the classic schoolgirl look. The teacher was lecturing on sex education when he started asking students to pair up, male and female. I looked around and there was only one other available person and we were both guys. We looked at the teacher and told him, "we don't have partners."

"Don't worry about it. Just partner up together," he said. "One of you can change clothes and take on the girl's role." My new partner and I looked at each other and it quickly became apparent that I was going to be the girl in this class. My dream partner was 6'3", 220 lbs. of muscle. My 5'9", 190 pound frame made me a man, but once we got the clothes, we realized that he would never fit. Resigned to my role, I quickly stripped off my men's clothes and started donning the schoolgirl outfit. Once I was dressed, the teacher continued his lecture. He talked about sex...STDs and health maintenance...vaginal...oral...anal...how to use a condom...bondage...control & submission...role playing...and on and on. Finally, he started handing out in-class assignments. Each pair was to re-enact something that he had lectured about. He started handing out assignments, and when my partner and I received ours, I blushed. I couldn't believe the assignment we'd drawn. Our task was to role play in front of the class a doctor's visit.

My partner quickly donned the doctor's coat (I have no idea where it came from...it just appeared in his hand) and told me to go lie down on the examining table. I did. He told me to close my eyes. I did. He told me to raise my arms above my head. I did. Quickly, using whatever tape was handy, my partner tied my hands together to a bar extending above the headrest. I lay there waiting as I felt his hands caress my arms down to my body. He unbuttoned my blouse and I felt him massaging my chest. I could hear the murmurs of my classmates as they took notes on what my partner was doing. I felt him move away from my body, heard a click, then I felt him come close again by my legs. He lifted my legs up and spread them apart. I opened my eyes to see what he was doing and almost jumped off the table as I saw him start to secure my right leg to one of the stirrups. He wasn't giving me just any doctor's exam. He planned to add a gynecological exam to the role play.

He finished tying my right foot to the stirrup then focused his attention on my left leg. I tried to struggle and get away from him but I didn't have the leverage to do so. Without a second thought, he secured my left foot in the stirrup and left me spread wide open for the class to see. I started to complain in protest and say that this was not a part of the class, but he ignored me. He slid up my skirt then took a pair of scissors and cut my panties off. I cried out and asked him what he planned to do, but I soon had my answer as he came around towards my head, stuffed my panties in my mouth, then used tape to secure them there. Now the only sounds I could make were muffled gasps and moans...both of which I found myself doing as I felt his hands caressing my legs and playing with my balls and cock.

I felt him start to slide his fingers into my anus. He pulled out some KY jelly to make it easier then stepped back. I couldn't see him. No matter how hard I strained, I couldn't see what he was doing. I felt him before I saw him again. There was an uncomfortable pain in my rear as I felt him try to force something up there. It felt too firm to be his fingers. Then he uttered one word... "speculum." And with that my humiliation was almost complete. I felt the tears in my eyes as I tried to cope with an experience that women dealt with on a daily basis. I struggled and squirmed, but that only made me more uncomfortable.

So I lay still and let my tears silently roll out of my eyes. As I felt more pressure, I realized he was opening up the speculum making it wider so he could get a better look inside...if that's what he was going to do. But I was wrong. Instead of just taking a look around, he walked away then came back with an enema bag. Somewhere in the distance, I swore I heard the teacher describing what was going on to the class...the elements of control and submission, role playing, anal play, and the like. But I tuned the teacher out. My focus was drawn to the feeling of the liquid being forced into my body. It started to feel warm...then warmer. I started to feel pressure build up and I started squirming, trying to get away. But it didn't stop. As he started to push the devices in and out of my anus, my hips started to grind trying to find whatever pleasure might be there.

On and on this went until I felt I was about to burst. I couldn't speak. I could only moan with frustration and a desire to be free from the torment that my partner was heaping on me. I was fighting for control but feeling powerless. My moans continued as I lay on the bed shuddering and twitching, while my partner came up near my head. He leaned down to whisper in my ear "embrace the pleasure, enjoy the pain, and...wake up!"

A searing light tore through my eyelids. "Hunh? What? What's going on?" I mumbled incoherently as I tried to remember where I was.

"Come on Jo. We're gonna be late for skiing, again" Frank said through the door. "Get up, get dressed, and come eat."

"Okay, okay," I replied. As I got over the shock of my rude awakening and started to get oriented as to where I was, I lay back on the bed and stared at the ceiling and tried to remember what I'd been dreaming about. Minute after minute, I lay there trying to remember. But all I could come up with was that I felt aroused, and full. My hands found their way to my erection and began to caress it through the nightgown, but it took me a minute to remember that the full feeling I had was caused by the tampon in my rear. "Shit...I guess I should get up and take care of things. First and foremost, get rid of the tampon, then maybe I can focus." My thoughts were starting to gain clarity through the early morning fog. I rolled out of bed and gathered my things so that I could get cleaned up and ready to hit the slopes.

As I made my way towards the bathroom, Tom called out "that must have been some dream Jo. You were moaning like a champ." I blushed as I scurried into the bathroom to relieve myself. After finishing with the can, I pinned up my wig then hopped in the shower. The water felt exquisite as it ran down my body, washing away the remaining tension from the day before and opening up my mind to the possibilities of the day. I finished up the shower then got ready for skiing. With the panties and bra, thermals, turtleneck, stretch pants, and vest, I was ready to go. A little light makeup and pulling my wig into a ponytail, I stepped out to meet the guys.

"Good. You're ready," said Frank. "We're late, so we put breakfast in a bag for you. We're heading to a different resort today, so that's the reason for the rush."

"Oh, okay. Well, let me put my shoes on, then we can go." I rushed to slide my feet into my boots and grab my coat, hat and gloves. "We're off." As we piled into the truck, we talked about plans for the day. But slowly, the conversation drifted back to the events of the day before.

"You know, Jo, I've gotta give it up to you," Frank said. "You were something to see yesterday. Very sexy. Probably sexier than you thought you were."

I found myself blushing again.

"Yeah Jo," Tom added. "As a matter of fact, we got a number of compliments...about you. Some of the people who saw you with us were impressed by your...performance. They actually wanted to meet you, but we told them you'd be tired. So, we arranged to go out to dinner tonight with a couple of the people that were there."

"Wait...are you for real?"

"Sure. It's no big deal. And it's not like you haven't been out dressed before. I mean, did you already forget being my arm candy all day in the casino yesterday?" Tom asked.

I tried to respond, but no words were coming out.

"Don't worry about it Jo. Dinner will be fun. Besides, we promise to have it just be dinner. Nothing you don't want to do."

"Frank, you seem to forget that this whole trip has had elements of me doing things I didn't want to do," I responded.

"Perhaps that's true," Frank said. "But can you honestly tell me that you haven't been enjoying yourself? Way, deep down...honestly...have you enjoyed yourself?"

I sat silently for a little while as I gathered my thoughts. I thought about the shopping trip on the way to the slopes. I thought about the bondage and being fucked by Tom and Frank. I thought about my willingness to ski while en femme. I thought about the sensual evening that Frank and I spent together. I thought about Tom's treating me like a lady, his lady, while we were at the casino. I thought about the display that I'd put on at the sex show. There were a lot of parts that I had been uncomfortable with, at least on some level. I guess, if I'd really wanted to avoid any parts of it, I could have started by not coming on the trip, especially since I knew what their goal was. I could have fought harder and been a less compliant lady. If I'd had the courage, I could have gone to the cops, dressed as I was, endured the humiliation of other people's thoughts and perceptions, but at the least, I could have gotten a ride to the bus station and a ticket home. I could have fought Frank's kindness and not accepted his gentle overtures. But I didn't. I didn't do any of those things. I went along with each step of their plan, giving up a little of myself along the way. Why? Did I really want to be a woman? Did I want to be their woman? What would happen when we got back to "civilization?"

"Frank," I started, "I'm not going to say that I didn't have times when I enjoyed myself. I mean, I've gotten past the stage of hating you and Tom for what you've forced me to do. And I guess, if I'm being honest, I've even allowed myself to enjoy some parts of it. That doesn't mean that I'm totally comfortable with everything that's happening. But I guess everything that's happened has tapped into some deep curiosity in me. Granted, I feel resigned to my fate of being your woman for the trip, and I imagine that I'll be in this role again at different points in the future. Hell, I might even have a little anticipation for some of those times. But, I'm still not sure what this all means... I guess, yes, I have enjoyed myself on some parts of this trip more than others. But I've also found myself doing some things that I would not have otherwise done if there were not some fear there about the possibility of something worse coming down the line."

"Jo, we're not going to hurt you, and we're not going to let anyone else hurt you...at least not in a way that causes any permanent damage," Tom interjected. "But we are pushing your limits, and we know that. Be hesitant. That's fine. Be wary. That's cool. But let go and enjoy it. Enjoy the surrender...the release...the powerlessness. You might even find out some things about yourself that you didn't even know were there."

I stared out the window at the passing trees. "Maybe..."

"Jo, tell me something," Frank paused before he continued. "When you're dressed as you are, even though it wasn't necessarily your decision, how do you feel?"

"I don't know. Soft I guess."

"Keep talking Jo," Frank encouraged.

"I feel...feminine is a word I would have to use. Maybe vulnerable too. I mean, it's a little scary to be out in public like this." I paused for a moment to gather my thoughts. "I am glad that we're in an area where nobody knows us because that makes it easier. But I still feel nervous about what someone might say if they read me."

"Okay, but what about when you're in a situation where nobody cares...like the sex show?"

"Well, there it was different. I felt out of control there because for the first part, things were being done to me...that spanking and whatnot. I guess it was different when you made me fuck myself with the dildos. I mean, I was more in control in the sense that I was doing myself. I could control the tempo, the depth, the position...all that was under my control. I lost myself in my head at that time and started to think of myself as a woman. Or at least I thought to myself, how would a woman respond if she were in this position? But I still felt out of control because I was responding to your commands and instructions...and that made me feel...free, I guess is the word. I didn't have to worry about what I was doing because it's like I was being told to do it."

"Kind of like you were being given permission to let go?" Tom asked.

"Yes," was all I could say. "It's not a feeling that I've had before, especially not in a sexual situation. Even with the women that I've been with, I was still the one in charge, and I did like seeing them lose it."

"See," Frank jumped in. "That's all we really want from you...for you to let go, lose control and ride the experience for all it's worth. When else are you going to be in a position to truly explore all those areas of your mind that you're afraid to uncover? When else are you going to be in a position to be so free and out of control because you know you've got people around you who are going to take care of you?"

"Well hopefully, in my next relationship," I retorted quickly.

"Okay, Jo. Fine," Frank said. "Hopefully you'll find that with the girl you don't know yet. But until you find her, why not let yourself go? See what it's like to be in her role. It just might make you a better lover."

Frank was trying to push some interesting buttons at this point, but I had to give it to him. He was making some interesting observations.

"Have you ever...let yourself go with your girlfriends Frank? Tom, what about you?" I asked, trying to regain some measure of composure.

"I wish I had. But I had to learn things the old-fashioned way," Frank said. "With some of my past lovers, they've been pretty open about things and the way that they felt while we were having sex. Hell, some of them turned me onto some of the same things that we've been doing with you. Now, I've never enjoyed receiving anal sex like you, but that doesn't mean that I didn't let one of my girlfriends stick her finger up my ass, just out of curiosity. It just didn't do it for me, not like it does for you."

"Same here," Tom added. "I've been into the bondage thing with my girl for awhile. We switch it up. Sometimes she's in control, sometimes I am. But whatever the case, we've both learned how to push those limits and learn how to be free in the moment."

"So, you're saying that you've done all these things for me for MY benefit?" I replied sarcastically.

"Honestly Jo," Frank looked thoughtful as he prepared his response. "Not entirely. Yes, I've thought you could stand to loosen up a little bit, but I also thought that it might be fun to step outside the lines a little and see what was there. Now that I've gone there, I've got a few more ideas of things to do with my girl."

I sat back, feeling pensive as I saw the sign for the resort coming up.

Tom said, "look, why don't we table things for now, and we can continue this discussion at dinner. Alright? For now, let's just hit the slopes and have some fun."

"Sounds like the best plan of the day," was Frank's response. "Jo? You okay?"

"Yeah. Just thinking." We grabbed our stuff from the back of the truck and off the ski rack and made our way to the day lodge. "I'm going to run to the 'ladies' room. Can you watch my stuff for me?"

"Sure Jo," Tom replied. "We'll be right here when you get back."

I walked off to the restroom to take care of business. In the hustle and bustle, no one paid me any mind, so I was able to get in, use the facilities, touch up my lip gloss, and head back outside. I found the guys in the same spot that I'd left them. "Okay. I'm ready."

We stepped into our skis and took off towards the nearest lift. We skied run after run, sometimes just cruising down the slopes, other times playing follow the leader, and other times racing each other to the bottom. We were always careful to try not to fall because whenever one of us did, the other two promptly aimed straight for the fallen friend before sliding to an abrupt "hockey stop" and spraying the downed person with piles of snow. There was probably more laughter during today's runs than during the first day because I was more relaxed in my role. I let the guys treat me like a lady and, in return, I favored them with flirtatious attention. They even play fought over me at one point. All in all, it was a great day on the mountain. The ride back to the cabin was much more relaxed and the conversation flowed more freely. Frank even took to the time to tease me about a couple of guys he had seen checking me out in the lodge. I blushed a little, but teased him back about how he'd been trying to run some game on a couple of other ladies there while he thought my attention was all on Tom. The jokes and banter continued all the way home. Finally, we pulled up to the cabin and took our stuff inside.

"Jo, ladies first in the shower. We KNOW how long it takes you to get ready," Frank said with a playful tap on my rear.

"That's right. I should get to take my time. After all, this kind of beauty isn't achieved overnight."

"Fine, fine," Tom added. "Take all the time that you need, so long as you're ready in an hour. Don't forget we've got dinner plans."

In the midst of having fun with my guys, I had temporarily misplaced that particular thought. "Right. I'll be ready." And I scampered off to the bathroom, shedding jackets and turtlenecks and ski pants along the way. I thought I heard Frank mumble something about getting his dollar bills ready for a private strip show later on, but I'd already closed the door by that point and was running my shower. I shaved and scrubbed and let the water wash over me. I got out and patted myself dry, feeling clean and refreshed. I sprayed perfume in all my intimate places and reflected on how much I seemed to be getting into my role as a woman. With each passing day, I fell further and further down the rabbit hole...but I didn't care. At least for the remaining time with the guys, I was okay being the girl. I accepted that there were things I should experience and learn about, and if I could find a way to integrate them into who I was trying to be, then it would all be worth it.

I sauntered out of the bathroom and across the hall into my bedroom. Through the door I called out to the guys, "hey, what kind of restaurant are we going to?"

Tom answered, "It's kind of upscale. We're wearing slacks and sweaters. I'm sure you'll find something appropriate."

I rummaged through the clothes that we had bought on the ride up and found a variation on the outfit that I'd worn to the casino. It was a pale blue suede miniskirt with a slit up the left thigh and matching jacket, which I paired with a black bustier with attached garters, black thigh hi stockings, black mesh panties with bows on the sides, and black 4" pumps. Probably the most striking feature of the outfit was the length of the skirt. It was short enough that you could see the tops of my stockings even while I was standing, but when I sat down, if my legs weren't crossed, my panties were pretty much in full view of anyone sitting across from me or next to me. I knew that the outfit was a little risqué given our location, but I figured that I might as well have a little fun with the guys. I let the hair from my wig fall across my shoulders and stepped out into the hallway.
"Hot damn Jo! You look amazing!" Frank had a look of awe on his face as I turned around to give him the full effect.

"What? What?" Tom called out from the shower.

"Don't worry about it," Frank responded. "You'll see when you're done." Frank returned to memorizing every curve that was hinted at by my outfit. I could have sworn I saw him licking his lips.

"You look pretty dapper yourself," I said to him to try and get his attention focused anywhere else. I was afraid that he might decide that he wanted to have me as an appetizer...which might not have been too bad, but I still wanted to maintain some level of decorum.

"Thanks Jo," he replied. "Can I get you anything while we're waiting on Tom?"

"Just water, thanks. Now what you can do is tell me about the people we're supposed to be eating with. I know you said that you and Tom met them during 'my show,' the other day. But who are they? What's the plan for tonight?"

"Well, it's a group of about 3-4 people that we're planning to meet at the restaurant. It's supposed to be 2 couples, males and females. The plan is just to enjoy a night out on the town and to meet some new people. Whether or not anything physical happens...we'll just have to wait and see. But I do know that the women want to get to know you. Back at the show, they were real curious about what your experiences had been like."

I nodded as I thought about what I might tell them. As I sat down to wait, I watched Frank's eyes follow my every move. I gave him a little show when I crossed my legs and I know I saw the front of his pants start to bulge. "Everything okay Frank?" I asked sweetly.

"Hunh? Oh, I'm fine. You know...just...taking in the sights," he said with a smile. "And I've gotta say, you are a helluva sight."

Tom finally came out from the back room to join us. "So what was all the commotion ab...?" He stopped dead in his tracks as he gave me the once over...then the double-take. "Jeez, I think I'm having a heart attack." Frank and I laughed. "Seriously, Jo...you look amazing."

"Thank you Tom." I smiled at him.

"Frank, do you notice that something seems different about Jo? There's something...I can't quite put my finger on it..."

"You're right Tom," Frank said. "I had the same feeling but I also wasn't too sure about what it might be." They looked at each other, then looked at me as if they were waiting for an answer. I sat for a minute soaking up the ambience and letting their minds work before responding.

"Guys, it's nothing physical. I didn't do anything different. The clothes are the same ones we saw in the store. The wig is the same one I've been wearing for the last few days. The amount of makeup I'm wearing hasn't changed, still just a little lip gloss." I paused before continuing, "The only thing that's different is my attitude." I looked each of them in the eye for a moment, trying to see if they understood. I decided to tell them a little more.

"Look, while we were talking this morning, you gave me a few things to think about. And some of it represented the same 'struggles' we've been having since you guys started me down this path. Don't get me wrong, once we get back to civilization, my male stuff is coming back. There will still be basketball and football and poker and all the things that generally like to do when we're hanging out. But what I've finally come to grips with is the idea that, in a situation like this, where I'm under someone else's control, I'm free to do whatever I want and be whoever I want. Granted, it's not like I'm going to go out and be some tramp or floozy. That's just not my style. But I can get into being a lady, even one who occasionally acts a little slutty for the guys that I'm with, which is basically you two. I know that there are still things we might explore, but we've already done a lot. I've experienced a lot as your 'girl,' and it's been an eye-opener. A little uncomfortable, sometimes more than others. But I'm accepting that I've still done most of these things willingly, even under the threat of punishment, it was still my choice. And there have been parts that I've enjoyed. So, I say let's see where this goes. For this trip, I'm your lady and I expect to be treated like one. Of course, I think we're all about to see just what that means, but it ought to be an interesting experience. I guess you could say that I've gone over to 'the soft side.'"

The looks on their faces as I'd been talking changed from curiosity to confusion to understanding. They knew that I'd finally stopped resisting and that I was ready to relax and have fun and be open to whatever it is they still wanted to show me. I knew them well enough to know that they would still treat me with a level of respect, but I also knew that they still had some kinky stuff up their sleeves that they were waiting to roll out.

"Are you ready?" I asked them.

"Yep," replied Tom. "It's about that time."

"On so many levels," Frank added. "Let's go." Tom simply nodded as he helped me put on my outer coat. As we walked to the truck, Frank was even gentlemanly enough to open the door for me and hold my hand as he helped me in. Before long, we were cruising down the road on our way into town to meet our companions for the evening. Along the way, we recounted our day's exploits on the mountain and laughed at various jokes. We also talked about future get-togethers...where we might go and what we might do. We arrived at the restaurant almost too soon.

As soon as we walked in, Frank waved at a couple in the waiting area. "Hey Gina, Mark. Good to see you again. Have you been waiting long?"

"No, not at all," Gina replied. "You must be Jo," she said as she turned to look at me.

"I am. It's nice to meet you," I replied with an outstretched hand.

"Oh come, come," she said as she pulled me into one of those hugs that girls tend to give each other. "I've heard so much about you that I feel like we're already friends." Her smile was mischievous, but sincere. "You look delectable in that outfit."

I smiled and complemented her back, "so do you. That dress looks fantastic on you." She gave a little twirl in her burgundy cocktail dress. "You're not too cold, are you?" I winked as she glanced down and saw her nipples pointing through the dress. She laughed.

"Not really. Besides, I've got Mark to warm me up." In the midst of me getting to know Gina, Mark had gone on to greet Frank and Tom. As I looked at him, I thought his face was kind of familiar and I realized that he must have been at the show earlier that week.

"Are the others here?" asked Tom.

"Yep. Elise and Alex are already seated," Mark informed us. "They're waiting on us."

Frank, Tom, and I followed Gina and Mark to a private booth in the back of the restaurant. It was obvious that the restaurant was designed to create as much privacy in a public place as possible. As I was introduced to Elise and Alex (apparently both of them had been at the show with Mark), I slid into the booth between Frank and Tom. Everyone chit-chatted as we looked over the menus and tried to figure out what we wanted to order. The waiters brought bread and water and took our drink orders while we continued to get to know each other.

"So, Jo," Elise started in, "I thought your performance at the show the other day was very memorable. I'd never seen a transvestite live before and you looked like you were enjoying yourself." I felt my face get hot and was thankful that my brown skin hid what would have been a raging blush. "I've been dying to know how long you've been dressing and what it feels like for you."

"Oh definitely," chimed in Gina. "I really want to know the full story because you really do look amazing and feminine and you seem to really enjoy being with Frank and Tom."

"Well...would you believe that this whole 'situation' started with a bet about 6 months ago?"

"No," Gina gasped. "Six months? That's it?"

"It's true," Frank said. "Tom, Jo, and I were playing poker and Jo lost a bet. He had to do whatever we told him to do and we asked him to dress like a girl."

"So, you had him dress like a girl. Did he look as good as he does now?" Mark asked.

"Did you do anything else that day? That's the real question," Alex chimed in.

"Well, we shouldn't kiss and tell..." said Tom, "but since we did more than kiss, I guess it's okay." Everyone laughed. "Once we got Jo dressed, it didn't take long before we had him serving us drinks and food...and after a few minor disagreements regarding point of view, Jo came around."

"Oh really?" asked Elise. "How so?"

Frank took this part of the response. "Well, he came over the couch after we tied him up and popped that cherry. He actually sucked his first cock that night...at least as far as we know."

"That was my first, thank you very much." The group laughed at my playfully indignant response. "The guys were my firsts for a lot of things. And I'll be honest, that first night left me pretty pissed off."

"I'll bet. It's just like a couple of guys to take advantage of a vulnerable young lady," Elise laughed as she responded with partial sympathy and scolded the guys. "Seriously though, you must have had a rough time."

"I don't know Elise," Gina replied. "After the first couple thrusts, I'd have imagined that Jo had a pretty smooth time." The laughter flowed freely at this point. The waiter returned with our meals so we put the conversation on hold while he was there. After he left, we started right back in.

"I'll be honest, it took me a few months after that night to even be willing to risk going out with those two again. My issue was that they told me that, now that they'd had me once, they were going to make it their goal to have me again and again whenever we were in private. That kind of scared me."

"So how did this trip come about?" asked Alex.

"It really happened because Jo made a mistake," said Tom. "Jo finally came by to hang out with us again for the superbowl. In the midst of the excitement of the game, he made a bet with Frank and Frank won...again. The bet consisted of this trip and Jo's obedience. And we have to give it to him, Jo has been a total sport going along with the bet. We've actually been talking a lot over the last few days and Jo has been coming to grips with 'her' position."

"Is that so?" asked Mark. I thought I caught a gleam in his eye.

"Within reason," I quickly added. "Yes, I've done some things over the last few days that are WAY out of the norm for me, but that's because Frank and Tom have generally treated me with respect and not made any demands that were inappropriate for the situation."

"So," Elise asked, "you were willing to do the demonstration at the sex show because everyone was doing it and it was basically okay?"

"Yes," I responded. "I'm not going to do anything in public that's going to cause me any unnecessary embarrassment and Frank and Tom have respected that. And as long as they continue to respect that, then I guess I'm willing to try most of the things they want to do...in private."

"So, what say we test that theory," Alex challenged.

"What are you thinking Alex?" asked Gina. Elise and Mark also looked curious, but I got the sense that they already had some ideas.

"Frank, if you and Tom are willing, how about we swap partners for the night?"

"What, you want to trade Jo for Elise?" Frank asked.

"No. I want to trade Elise and Gina for Jo...for Mark and myself." Alex said.

Frank and Tom looked at me. "What do you say, Jo? Are you willing?"

A Wager Lost Ch. 4

As I slept that night, I dreamt vivid dreams...sexual dreams. The next morning, I was able to remember one of the dreams that I had but I didn't tell Frank or Tom. I kept it to myself because I wanted to understand what it meant. I'd dreamt that I was walking down the street when I got close to the entrance of a park. It was me in my male clothes. As I got closer to the entrance I heard a voice behind me. I couldn't understand what it was saying but as I turned to look, I saw someone start to run after me.

As I started to run forward, I saw another figure start running towards me from in front of me. In order to get away, I turned into the park to try and get away. As I ran, the hedges started to grow taller and taller until they stretched far above my head. They were too thick to run through, so I twisted and turned along the path trying to get away. I ran full speed, missing some corners and crashing into hedges as I tried to escape from the voices of my pursuers. With each crash, my clothing became torn, and as some parts of what I figured was a maze got narrower, or were overgrown, I found myself losing some of my clothes entirely.

Finally, I entered the center of the maze but I felt a breeze all over my body. I looked down and realized that I was completely naked. I'd even managed to lose my shoes in the process of running away. I staggered towards what I believed to be a bench to catch my breath, but when I sat down, I fell straight through. It was as though the rabbit hole from Alice in Wonderland had swallowed me up. I slid down the hole faster and faster until I fell out onto a pile of pillows. I looked up, dazed and confused, but as I gathered my bearings I saw I was in a bedroom. I stumbled to my feet and looked around and there on the bed was a set of clothes that I could put on. The closer I got to the bed, the more the clothes looked like the very ones that Alice had worn in the story. I picked up the clothes and heard voices from outside the room...some in the hallway, others echoing down the tunnel through which I'd just fallen. I started rushing to get dressed in order to be able to make a partially decent escape...but I saw no door. Then, in the corner I saw nothing but a smile...the hallmark of the Cheshire Cat. "Now," he told me "it's time to find out just where the rabbit hole goes."

I started awake. "Jo, baby...you okay?" Frank roused from his slumber and reached for me. I was sitting up, breathing hard from the experience of the dream.

"It was nothing. Just a dream."

"Okay. If you say so." He rolled over to look at the clock. "It's about time to get up anyway. I must have been more tired than I thought."

As I gathered the covers around me, I felt fresh cum leaking from my ass. Frank saw me squirm and said "I guess we must have gone another couple of rounds in our sleep." He winked at me and made his way to the shower. While he was in the bathroom, I lay there contemplating my dream and figuring that the only meaning was that I was willingly ready to explore further dressing as a woman and whatever came with it. I had feelings of anxiousness and nervousness as I adapted to my new role, but I asked myself "how bad could it be? Last night wasn't that bad. It was actually kind of nice." I smiled as I thought about Frank's seduction of me. It really had been an interesting experience.

With those thoughts and feelings in mind, I made my way out of his bed and back towards my room.

"Hey Jo," Tom called out from the living room. "You guys sounded like you were having a REALLY good time last night." He laughed. "Well, today, you're with me. I laid out the outfit I want you to wear. I was going to wait for you, but it started getting so late that I figured you wouldn't mind."

"No problem Tom. Let me get cleaned up, get something to eat, then you can tell me what you've got planned."

I turned into my room and started to gather up what I needed for the bathroom. I saw the outfit Tom had laid out for me. It was a black leather miniskirt with matching jacket, royal blue corset with matching thong panties, black thigh-hi stockings, and knee hi boots with a stiletto heel.

"Tom," I asked, "where exactly are we going today?"

"Well, you're going to be my arm candy while I do some gambling. It always helps to have a sexy lady on your arm when you're at the tables."

"Okay." I didn't say anything else. I simply went into the bathroom and started getting cleaned up. After a few minutes, I heard Tom and Frank's muffled voices through the door...

"Frank, whatever you did last night really mellowed Jo out. What did you do?"

"Nothing big. Just treated Jo like the lady we knew he could be. I think she'll be much easier to handle throughout the rest of the week."

"Cool. Hey, check out this show that's taking place at the casino tonight. You think we should go?"

I didn't hear anything for a minute, then finally Frank responded "oh definitely. That party will be worth the trip. I'll tell you what. You guys enjoy your day, then I'll meet you at the casino around 5 this afternoon, a little before the show."

I was curious as to what party they were talking about, but I didn't have time to worry about it since I needed to get dressed. With that, I jumped in the shower and started my routine of showering, shaving, and putting on some light makeup. After I finished up in the bathroom, I went back to my bedroom to finish getting dressed. Once I was done, I stepped out into the hallway.

"Tom, do I look alright?"

"Jo, you look fantastic." Tom was looking rather dapper in a pair of slacks, a short-sleeved sweater, with his leather coat draped over his arm.

"Are you sure we'll be warm enough? I mean, we're surrounded by snow?"

"Don't worry. Once you get into the car, you'll be fine. The casinos will be warm enough and we'll be there for the afternoon. Frank will meet us there for dinner and a show later on this evening." Frank then tossed me something. "Last thing Jo. Put this in."

I caught it and looked at it. It was a large butt plug. "Umm. I don't know if this is going to fit."

"Come here," commanded Tom. Slowly, I walked towards him. As I reached him, he put his coat on the chair then told me to "bend over." I leaned over the table with my ass in the air as Tom started lubing up the plug. He pulled my thong to the side, then slowly and gently started filling my ass with the butt plug. I moaned as he pushed it in. Finally, when it was all in, I noticed that my breathing was a little ragged. "Don't worry Jo. You'll get used to it. I just wanted you to wear it because it will give you a little more sway to your walk." As I stood up, I felt incredibly full. And as I walked towards the door, I noticed my hips swaying a little bit more as I tried to accommodate the plug in my ass.

Tom opened the door for me, and as I sat down in the truck, I really felt the pressure from the plug. I squirmed. "You doing okay over there?" Tom asked as he slid in the driver's side. "Yeah, just adjusting. Don't go over any bumps, okay?" I joked. Tom laughed and pulled off. We engaged in small talk all the way to the casino. He asked what happened last night and I gave him a brief description of the massage.

"How did you feel?"

"I guess I enjoyed it. I still feel a little funny, but last night was probably the most relaxing time that I've had with you guys so far."

"Well, that's good to hear. Hopefully you'll enjoy today too."

Once we got to the casino, we parked in the underground garage. "What are you going to do first?" I asked.

"I figure we'll start with roulette, then maybe play some blackjack. We'll see how things go from there. But first," Tom said as he started to unzip his pants, "how about a little blowjob to take the edge off?"

"Tom, somebody might see." I started to panic and backed up against the door as my eyes darted from side to side.

"No, they won't. Trust me, nobody's looking for anything down here. And even if they do see, it's not like they haven't seen it before."

"What happened to not making me do anything out in public?" I asked, imploring him with my eyes to forego the blowjob.

"This...this is not public. I could have asked you to follow me into a restroom in the casino. I could still try to fuck you in the elevator. I could take you outside, find an alley in the cold snow and make you give me a blowjob there. I am ASKING you for one here in the privacy of my ride. I'm only going to ask the question one more time: Jo, please give me a blowjob before we go into the casino." Tom looked serious, but I didn't think he would hurt me if I refused.

"I...I can't. I'm too nervous. I'm sorry," I said as I put my head down and looked away. "Please don't be mad at me. It's just that...the cabin was one thing. This is another. I'm having a hard enough time knowing that I'm about to be in a public place dressed as a woman with a huge butt plug up my ass. Don't you think that's enough for me to have to do?"

"You're right Jo. No problem." And he zipped up his pants. "Let's go." He didn't look happy, but he didn't look pissed either. I really couldn't get a good read on what he was feeling.

"I'm sorry Tom. Look, I promise I'll make it up to you once we get back to the cabin. I promise," and I smiled at him, my eyes begging for forgiveness.

"Come on Jo," Tom said as he opened the door. "Don't even worry about later. For now, just be a sexy lady on my arm." He offered his arm to me as he walked me through the garage and into the elevator. He didn't say much to me as we walked but I tried to dismiss it and focus only on being as feminine as possible. I figured that the less I talked, the less likely I was to be read as a man.

I was so focused that I missed Tom's comments.

"Jo...Jo...listen to me. I was going to let you off the hook, but I think you should know that your refusal in the garage will have repercussions later on."

"Like what?" I asked hesitantly.

"I'll start with this," Tom said as he reached into his pocket. All of a sudden, I felt intense pressure in my ass as the butt plug started vibrating and pulsing.

"Oh...n-n-n-no...turn it off...please turn it off..." I stuttered and stammered as I tried to maintain my composure. "It's too intense."

"If you'd only done like I asked, you could have just enjoyed the plug," said Tom. "Since you still had to resist, you left me no choice. Well, that's not really true. I'm going to enjoy watching you squirm for the rest of the day, and that's a choice that...doesn't really bother me at all. You?" He smirked as he waited for my response. I was speechless as I rode the sensations and tried to stay ladylike. "Good. Glad to see you're not bothered. And you will make it up to me later. I guarantee it."

We walked to the main casino floor. Or perhaps Tom walked while I stumbled along beside him trying not to fall over due to the random sensations sent through my nether regions. Over the next few hours, we stopped at the blackjack tables, roulette tables, craps tables, and finally, the poker tables. Tom only let me sit down at the blackjack and poker tables. Honestly, I wasn't sure whether I was better off sitting or standing, because when I sat down, the plug got shoved further up my rear where it continued to twitch and vibrate and put pressure on my prostate. But when I was standing, I felt like me knees were going to buckle. There was no escaping its' relentless assault on my ass. I was only minimally aware of the occasional soft moan escaping my lips, but Tom paid me no mind. It was some of the looks that I got from others nearby that let me know that I'd actually made a sound. I saw some of the quizzical looks on their faces, but tried to ignore them, and they ignored me as they focused on their gambling. But I know that every now and again, while Tom and I were at the roulette and craps tables and the crowds were pressed together, I felt a hand pinch my ass. I knew it wasn't Tom because I could see both of his, but I couldn't turn around to see who might have done it. It didn't matter anyway, because I would soon be focusing on the vibrating butt plug again, alternately praying that the batteries would die so I could get a break and hoping it would continue so that I could cum. Neither one happened.

A few years later (okay, actually just a few hours later), we met up with Frank in the lobby of the casino.

"How'd you guys do?" Frank asked.

"I'm up about $700, so I'm pretty happy," said Tom. "Jo is feeling something else for an entirely different reason."

"Oh no. You didn't have to use it on her, did you Tom?" Frank asked as he shook his head.

"Yep. She refused a simple request when we got here, and I had to remind her that even minor innocuous requests should not be refused." Tom look disappointed as he continued on to say, "I thought that after last night with you, she'd be easier to work with, but since that doesn't seem to be the case, I guess we're running out of options."

"What...what are you guys talking about?" I stammered through my sensual onslaught.

Frank and Tom both looked at me, then each one took an arm and they led me to a hallway leading towards the ballrooms. They said nothing while we walked and I continued to look from one to the other for a response. Once we were in front of one the ballroom doors, they stopped.

"Jo," Frank said. "We're about to go into a different kind of show. The show is called Erotique, and there's a few things you ought to know. First of all, we'll probably be a few of only a small group of Black folks in the show. So that's going to draw attention to you regardless of anything else. Secondly, had you only obeyed, we might have let you enjoy the show in a different capacity. But since you continue to be stubborn, even after we had such a great night last night, then you're going to have to learn a few things. One is how to obey. The second is how to give pleasure on a moment's notice. The third is to surrender. I hate to say it, but in this show, the more you fight, the harder your life is going to be. I know I said back at the cabin that I don't mind a little fight because I like the challenge. But here, and know that I'm telling you this because I like you, fighting back, resisting is bad. Like on Star Trek, with the Borg... 'resistance is futile.'" Then he nodded at Tom who grabbed my wrists, turned me around and forced me to face the wall. As I started to stutter out a question, Frank produced a ball gag, seemingly from out nowhere and forced it into my mouth. "To keep the protests to a minimum," he said. I started having flashbacks to the first night the guys had their way with me and I started feeling nervous. I tried to squeeze a question out around the gag, but succeeded in making nothing more than a few mumbling sounds. Tom slid my jacket off my shoulders and arms, then tied my wrists together behind me.

"Are you ready Frank?"

"Yep. Let's go." Then Frank opened the door and guided me through the door in front of him. We took a couple of steps down a short hallway, then knocked on another door. A slat slid open and an eye looked us all up and down, then slowly pulled the larger door open. As we entered into the darkened room, my eyes started to adjust and I took in the scene around us. It was nothing like I'd ever seen before. Everywhere I looked, I saw people in bondage...people having sex...people being teased and tortured... I turned and looked at Frank and Tom with fear in my eyes because I knew what they were thinking. My eyes pleaded with them to walk us out of there. I pressed myself against Tom trying to coax forgiveness out of him by offering myself to him, but he just turned to Frank and said "I think our little Jo is feeling kind of frisky. Where should we start?" Either he'd misinterpreted my body signals, or he was just choosing to ignore my desire to escape.

Frank took my arm and started leading me through the room towards a corner that seemed to have an array of spanking mechanisms. As we walked, I saw people turning to look at us making our way through the room. I looked around and was able to spot only one or two other Black faces and I knew that Frank's words were true. I was going to be an attraction.

When we arrived at the corner, Tom unzipped my skirt, pulling it to the floor and I heard a few whispers and giggles as the crowd noticed that, not only did I have a large, vibrating butt plug in my ass, but I was also a man. "Mmm... I'd like to get a piece of that ass," I heard someone say, but I had no idea who it was. More comments followed as Frank and Tom pulled me towards one of the devices. There was a woman standing there, and she almost looked like a saleswoman.

"I see you've got a 'bad girl' there. Does she need a proper spanking?" She asked with a twinkle in her eye. Her name tag said "Lisa," and she and the guys started to talk as if I wasn't even there.

"Lisa, our girl Jo just refuses to act right. We figured that we'll have her make the rounds of some of the activities here until she gets her attitude right. What can you tell us about what we've got here?" Frank asked her as he pointed at different set-ups.

"Well, we've got various hand-held spanking instruments that you're welcome to use, and buy if you'd like to take them home with you. We've got paddles, whips, rulers, breadboards, belts...and a couple of other things that I KNOW you'll enjoy. If you'd like to try some of them out, why don't you get...Jo, is it?...set up, or tied down over here." She pointed to what looked like a padded counter. Frank and Tom dragged me over to it as I tried to resist being moved over there. But there was nothing I could do. The pushed me over the padded edge of the counter and spread my feet apart. Tom secured my feet to each leg of the counter while Tom grabbed a chain that was hanging down and tied my wrists to it. It was a position I'd been in before, but this time I felt much more vulnerable. I could almost feel the tears start to form in my eyes.

"Don't cry yet Jo," said Tom. "We haven't even started yet."

Then Lisa noticed the butt plug. "Did you want to take out her plug, or leave it in?"

"Leave it," both Frank and Tom said in unison which drew a round of laughs from the gallery.

I continued to moan and struggle in my bonds but there was nothing I could do to free myself. As I looked ahead, I saw Lisa moving a mirror in front of me so I could see exactly what they were about to do to me. "Such a deserving girl. I'm sure that whatever you're about to receive, you had coming to you." Then she returned to Frank and Tom and discussed the merits of each spanking instrument.

I heard her say "the smaller instruments give a more focused sensation and tend to leave marks. See?" Then I jumped as she slapped my ass with a ruler. Again and again, harder and harder...she just kept spanking my ass and legs. "You've got to be careful though, because if you hit too hard with the smaller ones, the likelihood that you'll break the skin goes up. You want to try and find a balance. The larger tools, you want to be more careful for a different reason. While they do produce an overall stinging sensation in the spank-ee, you don't want to hit too hard. I've heard of people actually causing internal injuries from spanking someone too hard with one of the larger paddles or breadboards." She then proceeded to demonstrate what a good level of force could be. "Anything that strong or less should get you maximum reaction without feeling like you're not doing your girl too much damage. Here Tom, give it a try." I looked on in horror as Tom wound up and proceeded to paddle my ass. With each stroke, I squealed and moaned. After about 5 strokes, Tom backed away and Frank came from the other side with one of the breadboards. The larger paddles left my entire ass tingling and each stroke forced the butt plug further and further in. I was losing myself in the pain and humiliation.
"Now, I want to show you guys something really special," said Lisa. "Since you've already gotten her ass warmed up, I'm going to cool it down with a little ice before bringing out the next toy." A muffled yelped came out of through the ball gag as she ran a couple of ice cubes over my sensitive skin. When she took the ice away, my rear felt tingly...a cross between feeling numb and overly stimulated. I looked up into the mirror to see what she was doing and I heard the crowd mumble and "ooh" and "aah" and say "that's pretty cool" as she wheeled a device up behind me. All I could see was that it looked like a bicycle wheel mounted on its side.

Lisa started her spiel. "This is our newest spanking device. It's been affectionately named 'Sir Spanks-A-Lot." The crowd laughed. "What you see is a bicycle wheel mounted on a small electric motor with adjustable speeds. You can position the wheel horizontally or vertically or anywhere in-between thanks to the adjustable mount. On the wheel, you can mount up to 6 attachments that are included in with the machine. If you want to use the harder spanking tools, we recommend that you position the spank-ee in a way that allows the machine to move them as they are spanked. For now, we'll just use the leather straps. Once the straps are attached, you plug in the machine and then adjust the speed by turning this knob here. We're working on a wireless remote for the motor, and that model should be available in the next few months. Once you set the speed though, just relax and watch the machine do all the work of spanking and discipline for you." With that she turned the motor on low and I felt my ass being spanked anew. My yelps and moans were in time with the slaps from the leather straps.

"Do it faster," I heard a few people in the crowd call out. "Faster...faster...faster." A chant had broken out as the crowd watched me get spanked by the machine.

"Okay. Now be aware that the faster the machine goes, the harder some of the lashes will be. We've got a built in governor to keep it from going fast enough and hard enough to break the skin." Lisa explained. "Do you all want to see the highest setting?" She called out. "Yeah!" responded the crowd.

"Is that all right with you gentleman?" Frank and Tom nodded. And Lisa turned the speed on the motor up to high.

"MMMHHHMMPPH!!!..." was all I could get out as the leather straps bombarded my cheeks. There was no more moaning with the beat. The licks came quick with no breaks to catch my breath. My ass was so sore and tender that each slap sent a spark through my body. I wanted the spanking to be over more than I'd wanted anything else in my life. Tears started to run down my cheeks and my sobs could be heard through the gag. Finally, Lisa turned off the machine and Frank came around in front of me.

"Jo, Jo...are you finally ready to stop resisting and do what's being asked of you?" He asked these words while cupping my face with his hand and slowly wiping some of the tears away.

I nodded.

"Do you promise to do whatever we ask you to do?"

I sniffed...and nodded.

"Let her up Tom." And Tom started untying my arms from the hanging chain.

"Lisa," Tom said, "make sure we have your card and a brochure because I know we'll want to order one of these."

"Oh, most definitely," Lisa responded with a million-dollar grin. "Thank you for helping out with the demonstration. I think that worked much better than just displaying the products."

And indeed it had, because the line of people touching and examining the machine was long.

Frank helped me stand up after Tom finished releasing my feet, and he cradled me to his side while I shed the remaining tears. Tom came by and slowly ran his hands over my ass and I squirmed. Everything was so tender that the slightest touch felt like fire on my cheeks. The guys guided me away from that particular corner and headed over to a wall. There they removed the butt plug from my ass and I stood there shivering and shaking as I got used to the empty feeling.

"Okay Jo. Are you ready for your first test?"

I nodded.

The guys led me to another corner where there was a huge array of dildos and vibrators. Some were hand-held, but others were attached to a board jutting from the wall just high enough that someone could get on their hands and knees and fuck themselves with it. I knew what they were going to ask me to do because I could see a woman on her knees fucking herself against the mounted dildo with another one in her ass. Her eyes were glossy as she reveled in the self-induced pleasure while a group of people looked on. She continued to fuck herself while a man came up to her and started teasing her breasts. She moaned in apparent ecstasy. Then, someone who had apparently been at the other booth watching my "demonstration" called out, "let's see the Black tranny fuck herself!"

Tom and Frank looked at me as I shrunk. But knowing I had no choice, I hung my head while they untied my hands from behind me and retied them in front of me. "Jo," said Tom, "you can pick the first dildo to use. But before you cum, you have to use 'the big one' and you have to use the one on the wall." I looked up to see what "the big one" was and nearly froze as I saw a dildo that must have been 5 inches in diameter and 11 inches long. I couldn't stop staring at it...whether it was out of fear or desire, I couldn't tell. I'd never had anything that big in my ass and I wasn't sure about trying it in front of a large group of people.

I started to shuffle forward to some of the dildos lying around, trying to see which ones looked manageable. Finally, I found one that was about 6 inches long, and about an inch in diameter. I picked it up, then looked at Tom and Frank for approval. They nodded that it was okay. I knelt down, then had to reach through my legs to insert the dildo into my ass. My hands felt delicate as I eased it in with a small whimper. Slowly, I started to fuck myself with it, moving it around until I found a spot where it actually started to feel good. For the first time since the night before with Frank, my ass felt good being invaded. I started to moan in pleasure and my hips started to writhe. My eyes were half-closed and I didn't see Tom approaching me. It wasn't until I felt his hands on my chest that I looked up. He'd gotten some weighted nipple clamps from somewhere and he put them on my nipples one at a time. I gasped at each pinch and started to squirm even more. As I continued fucking myself, Frank appeared and handed me a larger dildo. It had to have been about the same length, but it was wider, probably 2-3 inches around. I slid the first one out and slid the second one in. My moan was louder as the feelings were more intense this time. Still, I continued to enjoy the erotic feelings that were waking inside me. I started to surrender to the pleasure...feeling my ass full, my nipples taut, and my cheeks tingling. It was an extremely exotic and erotic moment. The minutes passed and I could tell people were still watching me because I could hear their comments, but I started not to care. I did, however, attend to Tom's voice when he said "use the one on the wall." I pulled out the dildo I had been fucking myself with and got on my hands and knees facing away from the dildo that was sticking, almost obscenely, out from the wall. Slowly, I eased myself back onto it, relishing the feeling of having my ass filled. I started to want it, and I moved faster. The change in positions brought different sensations, different feelings, and sent me to a new level. I rocked faster and faster. But the crowd wasn't satisfied.

"Give her 'the big one.'"

"We want to see her ride 'the big one.'"

I opened my eyes to look around and see what Tom and Frank wanted me to do. I hoped they would let me stay here because I was so close to cumming. But they didn't. They motioned to the large dildo on the rack and I crawled forward towards it, hearing a small pop as my friend on the wall exited my rear.

"Jo, stop right there for a minute." I turned to see Frank heading towards me. I wondered what he was planning to do. "You're going to need both hands for that one," he said as he untied my wrists. Then, he surprised me by taking out the ball gag. "The crowd wants to hear your unadulterated pleasure." He stepped back and let me continue on my path towards climax. I reached the rack and took down 'the big one.' I positioned myself on my knees over the huge dildo and aimed it at my ass. I started to force myself down onto it, trying to hold it steady with both hands, but was only moderately successful. I tried again and again, until I was panting from the exertion and pressure. I'd never felt that stretched before and it was taking awhile to get comfortable.

"Frank...Tom...please help me." The words came out of my mouth before I could realize what was happening. They both smiled at me and came over.

"Get on your hands and knees," Tom instructed. Frank took hold of the dildo and started to push it in while Tom dribbled more lubricant down my ass crack. Slowly, inch by inch, it went in. I was gasping and moaning and mewing, and the crowd was eating it up. Frank stayed behind me and started to fuck me with the dildo. My eyes closed. Then Tom started playing with my nipples and caressing my ass. I was in another world. This continued on for a couple of minutes and the crowd was appreciating the show. The last straw came when I felt Frank reach around me and grab my dick and start to caress it. My mouth opened as my breathing got ragged. He started stroking me in time with the pushes of the dildo. I think I started calling out "yes...more...please fuck me...don't stop..." but I'm not sure. My body was convulsing and my legs were shaking and I was so gone by that point that I didn't know what I was doing.

Until finally...I came. I spurted jet after jet of cum onto the floor in front of me, getting the release that had eluded me all day. I collapsed onto the floor to rousing applause from the crowd. "Oh my God," I thought to myself as I started regaining control of my senses. "What did I just do? What just happened?"

I opened my eyes to see Frank and Tom standing there like proud parents. "That's our girl. We always knew you could do it." I continued to lie there trying to catch my breath. Other people that had been watching stopped to congratulate Tom and Frank on having such a wonderful girl to play with. I saw them exchange information with a few people and heard mumbled words about a private party at a cabin by the lake in a couple of days. But I wasn't focusing on much. My body was wired and I could feel everything. The stickiness of the cum underneath me. The dildo still lodged in my ass which I was afraid to remove without help. The nipple clamps pulling. The twitching in my dick that was always there after climaxing.

Finally, Frank and Tom turned their attention back to me. They removed the dildo from my rear, then took off the nipple clamps. They helped me stand up as Frank handed me my panties and skirt. "Jo, you are turning into quite the amazing lady," he said with a proud smile.

"That she is," Tom added as he helped me put on my coat. "That she is. Are you ready to go or was there more stuff in here that you wanted to see?"

Before Frank could respond, I interjected "could we PLEASE go home?"

Frank laughed at my response. "Sure, sure. After all, we can see some of the things that were in here another time." He winked at Tom. At least I thought he did. I couldn't really be sure because I was so exhausted that it took all my concentration to hold onto his arm as I tried to put one foot in front of the other.

We walked out of the "show" and back to garage. I gingerly sat down in the truck feeling both empty and sore. "Please, no more tonight. I just can't do anything else. All I want to do is go home and crawl into bed."

"Okay Jo. We'll give you a break, at least as far as sex goes. Just...take a bath when we get home, then you can go to sleep," Frank reassured me.

"Thank you. I promise, tomorrow, we'll do what you want. I just really want to sleep."

Tom turned on the radio and I nodded off on the way home. Once we got there, Frank roused me and helped me inside and then into the bathroom where he started running the bath for me. "Just strip off your clothes and leave them in here. I'll take care of them for you. And I'll be back with a nightgown for you." He left me to get undressed and it felt so good to take off the jacket...the boots...the stockings...the skirt...the panties...and the bustier. My nipples and ass were still tender, and as I slid into the tub, I felt the water start to massage away some of the pain. I also felt it slip into my still stretched ass. "I guess I'll have to wear a tampon tonight anyway," I thought to myself before closing my eyes and relaxing in the tub.

About 30 minutes later, Frank came in with a pink cotton nightgown. "Here you go. Get some rest tonight, okay Jo? Don't forget, we're still going skiing tomorrow." I groaned as he winked at me and left. "Can't a sistah catch a break?" I thought before getting out of the tub and toweling off. I got dressed in the nightgown, waved goodnight to the guys, and crawled into bed. I passed out with unrecalled thoughts and dreams about what the next couple of days would bring.

A Wager Lost Ch. 3

I woke up the next morning feeling a little tired, a little stiff, and definitely sore. But it wasn't the kind of soreness that came from exercise. It was just my rear. The beads and the pounding from Tom had done their job. As I rolled out of bed, I felt the tampon in my rear and immediately wanted to get rid of it. I started to walk but even that felt different. I hoped the feeling would go away, but I didn't that it would because I knew that whatever Frank and Tom had planned for me would probably culminate in some sort of anal experience. As I grabbed my things and made my way to the shower, I heard Frank in the kitchen.

"Good morning Jo. Did you sleep alright?"

"I slept better this time than I did back at your house Frank, if that's what you're asking." My feelings were still a little raw and bitterness coated my words. Frank just shook his head and went back to eating breakfast.

"Jo, while you're in the shower, I'll lay out your ski outfit for you."

"Why? Do you think I'm incapable of dressing myself," I snapped.

"Dammit Jo. Just chill for a minute. All this hostility is going to make this week really rough and it doesn't have to be that way." Frank sounded exasperated.

"Alright, alright. I'm sorry." I said. "I just want to go get cleaned up."

"Fine, but don't take too long. Tom should be ready in a few minutes too, and I'm eager to hit the slopes." Frank looked like he was done, but there was one more thing he wanted to say... "By the way Jo. One last request."

"What's that Frank."

"Shave."

"What? Why?" I asked.

"Well, for two reasons," Frank responded. "The less important reason is that I want you to." He paused for a moment. "The more important reason is that if you're going to be out wearing women's clothes, do you really want a lot of people looking at you?"

That caused me to pause because up until that moment, I hadn't considered that Frank and Tom might actually make me leave the house en femme.

"Frank, you're not seriously going to make me go outside dressed like a woman are you?" I started to feel panicked.

"Yes Jo, I am. But I still want you to be comfortable." He said. "I figure that if you shave...everything...then maybe, with a little make-up, you could pass for a woman. I mean, you won't be able to stand up to any in-depth scrutiny, but hopefully, it will be just enough to minimize the stares that I know you're worried about getting. Just trust me."

And with that, I was face-to-face with a stark realization. Frank and Tom wanted their 'ski bunny' and I was it. And if they wanted to go out on the town, they planned to drag me along. If I didn't want to be further embarrassed, I needed to get with the program. I started to shake.

"Frank, please don't make me do this. Don't make me go out like a woman. Just give me my ski clothes so I can be a man for the day and when we get back, I promise, my attitude will change. I'll be more feminine in the cabin. I give you my word. Just don't make me go out dressed." I begged with fear and nervousness tinging my voice.

"It's too late Jo," he said and I cringed. "I'm not doing this to be cruel. Honestly, it's just that the only clothes we brought for you are women's clothes, so you don't really have much choice as to what you're going to wear. Where you do have some control is in how people respond to you. I can guarantee you that wearing the outfits we brought will generate stares if you've got facial hair. Take the hair off and you'll get away with a lot more. Plus, I've got another special item for you that should also make it easier."

"God Frank. Do you hate me? Is that why you're torturing me like this?"

"No, it's not that at all. Tom and I just have specific things that we like and want. This time around, we hadn't planned on things taking the turn that they did, but now that we're here, we both intend to make the most of it. If you could stop being so pissed off at us, you'd see that our behaviors towards you are limited in their context. Once the bet is over, we'll treat you like the man you are. But until, we're treating you like our girl. And we want to make that easy for you, but you keep fighting us every step of the way. Now I don't mind a little bit of a challenge, and a little fight from you keeps it interesting and fun. However, once we step foot outside that door, Tom and I will only be able to do so much for you. You're the one that's going to control how others perceive you. If you want them to see you as a man en femme, then that's what they'll see. If you want to make them second-guess what they're seeing, then do what you've gotta do. The second option will be less embarrassing for you, I guarantee it. But if you want to fight us, go ahead. You'll be bringing the external humiliation on yourself, then you'll have to deal with the consequences once we get back and are behind closed doors." Frank stopped his diatribe and stared at me. "Jo, I've told you what I wanted. I've given you options when I chose to, but now, we're entering a situation that is beyond my control. It's your turn to make the decision. What are you going to do?"

Tom had, without my knowing, stepped out into the hallway and he echoed Frank's question, "what are you going to do Jo?"

Reluctantly, I nodded my head and turned back towards the bathroom. "Okay," I responded meekly. "I'll shave. I'll do whatever I have to in order to blend in as much as possible in public." And with a tear in my eye, I closed the bathroom door knowing that I had just made a major decision to do whatever I had to in order to survive. It wasn't physical survival that I felt threatened with. It was my emotional well-being that I had to look out for. I figured that following the commands from Frank and Tom would be easier to cope with than the potential public ridicule I would face if I continued to be stubborn and obstinate. I wasn't happy with my decision because I felt like a piece of "me" was slipping away, but I hoped that in the long run things would be easier if I did things their way.

So, with my fingers crossed and a wish on my lips, I began getting cleaned up. I shaved my face, my body, my legs, even my groin. I showered, patted myself dry, then started putting on what was to be my public persona for the next few days. I slid on another pair of cotton panties, some hi-cut bikinis, and a matching camisole.

"Jo," I heard Tom call through the door. "We left your clothes on your bed. Get a move on or else we're gonna get a bad parking spot and miss out on the best runs of the morning."

"Okay, I'm coming." I stepped out the bathroom and made my way across the hall to my room.

"Let us know when you're done getting dressed," Frank said. "Don't forget, we've got at least one more item that ought to help. Oh, and don't worry about any tampons or other anal gear. At least not for today. Unless you need them or want them...?"

"No, no. I'm okay. I'll be dressed in a few minutes," I responded.

As I shut my door, I looked at the clothes they had laid out. Since it was cold, they'd left me some silk thermals and sport socks to wear, but it was the ski outfit that did me in. They'd gotten me a baby blue turtleneck, a black fleece vest, a pink and blue ski coat, and some black stretch pants with a decisively feminine fit. I knew that anybody who saw me wearing those clothes would think I was a girl, so I was semi-glad that I'd gone along with Frank's suggestion to shave. After sliding into all the clothes but the jacket, I turned to the dresser. There, they'd left an array of make-up with a note that said "use only what you want...but lip gloss is required." As a show of defiance, I only put on the lip gloss. It was like winning a small victory.

I grabbed my coat and headed out the room to meet the guys.

"Jo, like we said, we've got one more thing for you. Sit down please," was Tom's request. "This will hopefully make it a little easier to feel feminine and it should pass casual inspections." Then I felt Frank placing something onto my head. It was a wig. I knew that the minute I felt the strands brush the side of my face. Frank tugged it, and shifted it a little until Tom gave him the ok. "Have a look," said Tom as he moved from in front of a mirror.

And there I was. A softer face, made so by the black wig that framed my face, falling to just below my shoulders, and lip gloss giving my lips kind of a wet look. I wasn't perfect. Anyone looking closely would be able to tell that I was a guy, but for the first time that morning, I felt like I had a chance of making it through the day without broadcasting my (remaining?) masculinity.

"We added some adhesive to the wig that will definitely keep it from falling off," Frank said. "You can put it in a ponytail if you want, or even get it styled later on...if you want. But it won't come off until we add some of the solvent that came with it. So feel secure that you're not going to be flying down the mountain and then see your hair go in the opposite direction." He smiled.

I offered a small smile of thanks back to both of them.

"Now, are we ready to go? Jo, got your tennis shoes?" I nodded.

"Okay then. Let's hit the slopes."

"Oh yeah...Jo, one more thing to remember," Tom added.

"What's that?"

"Well, we know you can keep a few small items in your pockets, so here's some lip gloss, a tampon if you need it," Tom smirked as he said that, "some money, and your cell phone. Last thing. Don't forget to use the LADIES room if you have to go to the bathroom."

"And for Pete's sake, sit down while you're in there," Frank added through a sudden fit of laughter.

My blush would have been visible if not for my brown skin.

"Off we go."

And off we went. We got to the slopes and, while we had missed a chance to lay "first tracks," we still got to do some great skiing. The guys were gentlemanly in their behavior towards me all day. They joked with me, teased me, and flirted with me as though I was a real girl. It was a little unnerving at the beginning because I was so worried that I'd be "read." Of course, it probably was a little easier since I had on ski clothes, which are generally a little bulky, hiding me. Still, once we got going, things were okay. I actually forgot about my appearance while we were actually skiing. Once we stopped for lunch though, I was reminded of my current state because I had to go to the bathroom. And that was the one time during the day that the guys subtly reminded me of my current position. When I made my intentions known, Frank leaned in and whispered, "remember...it's the door with the girl on it." Then he sat back with Tom and laughed. I quickly hustled off to take care of business, remembering to sit down while I was in the stall, and even going so far as to touch up my lip gloss as I was at the sink. I quickly made my way back to the guys who were still sitting at the table, enjoying what was left of lunch.

"Ready to go?" Tom asked as I got back to the table. I nodded. We gathered up our things and made our way back out for the afternoon runs. It felt really good to be floating down the mountain, twisting and turning and enjoying the challenge. But after about 2-3 hours, we were all ready to call it quits. We knew it was time to go when Tom got to the bottom of the hill and, in trying to show off, came to a stop, then promptly flipped over when his skis stuck in the slush at the bottom of the hill. We all laughed and got our gear together as we headed back to the truck.

"Jeez, I'm sore," I said as we climbed into the truck. "It's been a long time since I've had that type of workout."

"Really," said Frank. "What about last night?"

"That was different and that resulted in a different type of localized soreness. This, this is an all over type of soreness."

"Tell you what Jo, since you've been such a good sport today and it looked like you actually enjoyed yourself, how about I give you a massage after dinner?" I looked shocked and surprised at Frank's offer. But being naturally suspicious, I had to ask "what's the catch?"

"No catch," Frank responded. "Just trying to be nice. I'm not saying that there won't be 'extracurricular activities,' I'm just trying to help you take some of the edge off."

I looked at Tom for confirmation.

"Jo, you should do it. It doesn't all have to be forced. We told you that we wanted you to have a good time too, so let us hook you up. Once we get back to the cabin, take a bath, read a book. We'll have dinner, then for tonight, I'll make myself scarce. You two can have fun and do whatever. I'll rejoin the activities tomorrow. Does that sound any better?" Tom asked.

I was skeptical but figured I might as well take the shot, if for no other reason than to see if they were being sincere, or if they were just trying to sucker me in for something else.

"Okay Frank. After dinner, I'll take you up on your offer." I was still a little nervous about getting a massage from a guy that I knew, but I figured he'd already fucked me, so it's not like I had to worry about him making a pass. That was guaranteed. But it was still different, because before, I hadn't been in control. I had been forced to submit. Now, I was giving myself over to Frank willingly and that was my struggle. That was the thought on my mind as I fell asleep for the rest of the ride back to the cabin.

"Jo, wake up Jo. We're back," Tom said.

I had no idea that I'd been that tired. "Oh, okay. Thanks." I almost fell out of the truck while trying to gather my things together.

"Hey, try not to drown while you're in the bath, okay?" Frank laughed as he noticed my struggles. "Here, let me take the skis and poles." I was again surprised by his behavior because it was just so different from anything I'd seen or experienced before. I decided not to look a gift horse in the mouth and let him carry my equipment into the house while I headed straight for the bathroom to start the bath, then to my room to change. As I went into the bathroom for the bath, I heard the guys watching TV and planning dinner, so I figured I'd be undisturbed for awhile. As I started to lower myself in the tub, I remembered the wig and quickly found one of the scrunchies they'd provided me with and tried to put up my hair the way I'd seen past girlfriends do it. It wasn't perfect, but at least my new hair didn't get wet.

I must have lounged in the tub for almost an hour, just soaking the stresses of the day away. Finally, when my stomach reminded me that it needed attention too, I got out of the tub and dried off. As I made my way across the hallway I heard Frank call out "I left two outfits on your bed for you to wear tonight. Your choice." Then he went back to watching TV. As I entered my room, there on the bed were my options. One was a black sheer teddy with an open back. The other was a sheer black chemise with matching thong panties. I was intrigued by both of them, but decided to go with the teddy. Slowly, I pulled it on, first sliding my legs in, then tugging it close against my body, tucking my penis beneath me, before finally attaching the halter straps behind my neck. It was a unique type of feeling, being wrapped in the teddy as I was. I decided to keep Frank guessing by grabbing one of the sweaters that he'd bought for me on the way and pulling that on. I also grabbed a denim skirts and quickly slid that on with a pair of pumps before sauntering out for dinner. As Frank looked up with a question in his eyes, I ignored him and sat down at the table while waiting for Tom to bring the food.

"Well, that wasn't quite what I bargained for," said Frank.

"True," Tom added, "but you didn't specify in the note that she couldn't wear something on top of the outfits that you selected."

"Well, I guess I'll just have to be more specific next time," Frank responded with a smile.

As we ate, we talked about the runs we enjoyed during the day and we made plans for the rest of the week. We decided to take the next day off, then ski at a different resort for the following days. But as for tomorrow, the guys wanted to take me to the casinos for a little gambling and a show.

"I'll go to the show, but I'm not gambling. Don't think I've forgotten that that's what got me in this mess...or position to begin with. No thank you. No gambling for me." They both laughed.

"That's fine. You can be my arm candy," said Tom.

"Well, you two have fun tomorrow. I think I'm going to gamble for awhile, but maybe I'll hook up with you for the show. But as for tonight, I think I'm ready to flex my muscles a little bit."

"That's my cue. You kids be good now." And with a wink and a nod, Tom excused himself from the table, put his dishes in the sink, then retired to his room to watch movies or sleep.

"So..." Frank looked me up and down. "Where would you like to receive your massage? Your room or mine?"

"So many decisions," I joked. "What am I to do?"

"Pick one, before the decision is made for you." Frank was about to take control again. "I'm going to clear the table. When I'm done, I'm going to find you wherever you are, then I'll give you a massage and we'll see how things go from there." He got up and started stacking dishes. I waited until he had ventured further into the kitchen before sliding my chair out and making my way down the hall. I was still mentally adjusting to the role that I had so willingly taken on during the day, but I swallowed my nervousness and made my way into Frank's room. As I stood in the doorway, I heard footsteps behind me.

"Go ahead."

I turned to face Frank. I looked him in the face and let him see my confusion and distress.

"Don't worry about anything. What happens here stays here." With that, he gently grabbed my waist and guided me further into the room. "Before we go any further, I want to see what you're wearing. Just take off the sweater and skirt. Keep the shoes on." Then he stepped back and waited for me to strip. Slowly I shimmied out of the skirt, letting it fall to my feet. As I started pulling the sweater up over my head, I heard him say in a soft voice "very nice." I stood there before him, dressed only in a teddy and pumps, with my hair hanging across my shoulders and my hands crossed in front of me.

"Lie face down on the bed."

I moved around the side of the bed and crawled onto it. I put my face on the pillow and tucked my hands underneath the pillow so he wouldn't see them shaking. I heard him taking off his clothes. By the time he got close, he was wearing only his boxers. Then I heard him turn on some soft music. He didn't sound like he was close by so I opened my eyes to peek at where he was. I saw him lighting candles around the room and I thought to myself "is he trying to set up a seduction." I didn't say a word. I just lay there and closed my eyes waiting for him to make the next move. I felt him looking me up and down, soaking the image of me in and burning it in his memory. I closed my eyes and waited for him to make the next move. I smelled it before I felt it. It was the scent of perfume. Then, I felt lotion being spread on my back. I felt Frank's hands kneading the muscles in my back, pushing all soreness and stress away. He started up towards my shoulders and worked a knot that had been there all day. "Relax" was all he had to say. Then he continued with the massage. He spent a few more minutes working on my shoulders and arms, then started working his way down my back again. I felt him spread more lotion on my lower back as he neared my hips and ass. He massaged my lower back and ass and only flirted with my asshole. I felt his fingers dip into the crack of my ass and just lightly probe my hole before he continued past it and started working on my legs. Slowly and methodically, Frank worked the muscles of my legs and involuntarily, I felt a moan escape my lips. I blamed it on the skiing we had done earlier and appreciated the relief his hands provided. Minute after minute, he worked on my legs moving with tender care further and further down until he reached my feet. I was surprised when he started taking my shoes off. I started to say something, but Frank stopped me. "I'm going to put them back on in a minute. I just wanted to massage them too, and put some lotion on them." I didn't say another word. I was still somewhat dazed by Frank's outpouring of gentleness and caring, and I was relishing the sensitivity with which he treated me. His massage nearly put me to sleep, but I suppose it was my curiosity at where he would take things next that kept me awake. Still, I could see how people got addicted to receiving massages.
"Roll over," he said. Slowly, I rolled over onto my back, feeling relaxed and sensual. It was a very different experience than the other times that I had been used by Frank. "Keep your eyes closed," he said. I felt him start to rub the front side of my legs with lotion and I couldn't believe that the massage was continuing. I started to peek at the clock when I heard him say "you're stubborn to the end aren't you?" But there was no malice or harshness in his tone. Not even the commanding nature that had characterized our other encounters. "I guess there are some things that we just won't be able to change," he said as he reached up and softly closed my eyes for me. "Since you seem to want to peek, against my requests, I'm going to blindfold you. After I do that, please, just try to relax...for me." I didn't say anything, but I did raise my head so he could slide the blindfold over my eyes.

"Now, back to the massage." And he started up right where he'd left off...rubbing the front part of my legs and working his way up to my thighs. As he got closer and closer to my groin, I felt myself start to harden, even while tucked away in the teddy.

The next touch surprised me. Frank started to spread my legs and he pulled my penis loose. His lotioned hand started to stroke it slowly, gliding up and down, until he decided to tuck it in the front part of my teddy, trapping it against my stomach. I was in shock because in our past two encounters, Frank had never really acknowledged that I even had a penis, let alone touch it. Tom had been the one to put it in captivity the other night. So for Frank to touch it at all left me shaken and quivering with a desire for release that had long been denied to me.

Frank continued to massage my front...my thighs...my hips...my stomach...then he reached my chest. I wished I could see what he was doing but the blindfold made it impossible. I could only wait for the next touch, imagining where it would be. Then, it came. The soft touch on my nipples and my pecs/breasts. Frank started to massage them slowly, rubbing them all over then teasing the nipples through the teddy. He pinched them, but not to cause pain. But with each pinch, I still gasped and I felt my body arch as he pulled on them lightly. I'd never known a feeling like this. I almost wished he would continue...until I felt his hot breath on my right nipple as he started to lick it through the teddy. He licked it, then sucked it and I moaned. I felt myself starting to squirm with a pleasure that had been denied to me before. I thought to myself "my God...if this is what girls feel when guys are kissing on them, it's no wonder they like it..." I had no time to pause and consider the changes in my thought process because Frank moved to my left nipple and started the process all over again. I lay there, soaking in the experience, feeling myself moving closer to a precipice I never thought I'd reach with a man...a point that I'd never considered reaching with a man because I wasn't gay (was I?). I knew that I was moving towards a climax, but wasn't there yet. I was somewhat ashamed to be this aroused under the ministrations of another man, but I didn't want it to stop.

Frank pulled himself away and I heard myself utter a moan of a disappointment. I couldn't believe that the sound came from me, but a part of me didn't care. I found that I was enjoying the experience of being on the other side of things. I wasn't the aggressor. I wasn't expected to be in control. I knew that I was still a participant, but for the first time, I started to really feel out of control...in a good way.

"If you're enjoying yourself more than you thought you would, nod." I nodded. Slowly, but with no hesitation. "Good," he said. "Finally, you're coming around to the possibilities of what could be...at least in this time and place."

I felt his weight come back on the bed, but I could feel him at the foot of the bed. As he moved up the bed, he spread my legs wide and situated himself on top of me. He didn't rest his weight on me though. I could tell he was using his arms to support himself as I felt his breath on my neck. Then, a nibble on the right...a nibble on the left...a little tongue in my left ear...a gentle kiss on my forehead...a light tonguing of my right ear. My breath was coming in sporadically and raggedly. I could feel his dick pressed against my balls while my dick strained against the teddy. I could feel his stomach pressed against mine. I reached out and felt his arms taut, supporting his body. Then...I felt his kiss on my lips. Lightly he kissed them. His tongue caressed my lips and parted them. I responded to his kiss as though I had no control over my own body. Deeper and deeper he kissed me and I felt myself rising to meet him. I wished I could see, but I settled for feeling as I wrapped my arms around his back.

We continued kissing and rubbing our bodies against each other for a few more minutes before I felt Frank pull away again.

"Roll over, but stay lying down on your stomach."

I rolled, then waited for the next sensation. Again, I felt Frank spread my legs and position himself between them. I felt his hands on my ass, spreading my cheeks apart so he could find my hole. As he started to tease my hole with his fingers, I felt the coolness of the lotion dripping in. I tried to relax as he slid his fingers in...first one...then two...then three...I squirmed and he used his other hand to put pressure on my lower back, keeping me in place. I started to breathe ragged little breaths as he finger-fucked me for a few minutes, but I was mildly surprised as his slid his fourth finger into my ass. I gasped and tried not to move while I got accustomed to this sensation. This was so different from the invasion I had experienced from the vibrator on the machine, or the beads, or even from the cocks of Frank and Tom. This was a little more tender...a little less pressured...and a little more unpredictable. That last thought hit as he started moving his fingers around in my ass, causing me to sharply inhale right before a little moan escaped my lips.

"Are you ready?" he asked.

"Ready for what?" I replied. Only I didn't get all of my answer out because right in the middle, Frank started forcing his entire hand into my ass. "Wait...wait...wait..." was all I could manage to get out. Even though he was going slow, the pressure was amazing and I had never been stretched quite like that. "Oh God...it's too much..." I moaned into the pillows. But Frank didn't stop. He pushed, added lotion, then pushed some more until his entire hand was up my ass. I didn't move. I just lay there reveling in the mix of pleasure and pain praying that he wouldn't move...because then I'd have to readjust.

"I'm pulling out now." And he did just that. Slowly, gently, he removed his hand from my ass and I was left shuddering on the bed trying to get my mind around the fact that I had just had another man's hand ENTIRELY up my ass. I wasn't able to ponder the thought long though, because Frank moved on top of me and gently eased himself into me.

This was different. I wasn't bound. I wasn't being handled by two guys at once. It was one man on top of me, slowly, almost lovingly, fucking my ass. For the first time, I didn't feel like I was being assaulted...I felt...sensual. Feeling his weight on my back with his dick in my ass, I wanted to move against him. Even as he fucked me, his hands caressed my arms and pulled them above my head where he intertwined his fingers with mine. His fucking was slow and luxurious and it forced me to grind my own dick into the bed. With each of his thrusts, my cock was caressed by the mattress and teddy giving me my own special pleasure. Thrust after thrust from Frank and my pleasure built.

"Oooh Frank," I moaned. "I think I'm gonna cum."

"That's good Jo...that's good...I'm not far behind you."

Frank started pumping faster and his pressure on my prostate combined with the sensations from rubbing against the teddy made me feel like I was going to burst.

"Please...Frank...please...quick...can't hold on..." My statements were jagged. My breath was ragged. My body was starting to shake from the exertion and the pleasure. I felt muscle twitches all over my body and second after prolonged second, I tried to hold on until I could go no further. "Mmm...ooo...uunnhh...mmmm...!!" was all I could sputter as I came all over my stomach. Then Frank started grunting...harder and harder...and his pounding reached a new level until finally...he came with a bed-shaking, toe-curling orgasm. My mouth was open in a silent "O" as I tried to breathe under the pressure. My hips bucked as Frank spurted jet after jet of cum into my ass. After he was done, we lay there for minute after minute, trying to breathe and recover our spent energies.

Finally he spoke. "So...was it good for you?"

I laughed. I didn't mean to. I never thought I would. But I did. I giggled and said "yes."

"See what can happen when you just relax?" I could hear the smile on his face as he spoke. Slowly, he let go of my hand and began to trace the outline of my body with his finger. I shivered at his touch, but I longed for more.

"Jo, that was the way things should have been. Maybe if we'd started there, you wouldn't have been so resistant all along."

"No. I disagree." I stated. "I never wanted any of this to happen. At least not on a conscious level. Now that it did, I'm still not entirely sure how I feel about it."

"Oh really?" teased Frank as he ran his hand over my nipples and then down to my softening cock which twitched involuntarily in his hand.

"Yes Frank. Really. I'm not going to lie to you though, and say that I didn't enjoy what just happened. I mean, that was amazing...and surprising...and sensual...and scary...and enjoyable. And I guess that while we're here on this trip, I'll go along with some of your games and plans. But once we get back, I want my life back. I want my manhood back."

"Okay Jo. I can respect that," said Frank as he continued to caress my body. "Let's deal with the real world once we're back in it though. Is that a deal? Can we just enjoy the moment and let tonight be tonight and this trip be what it is?"

"I suppose so," I mumbled through a yawn. "Damn, I'm tired."

"I know. I've got skills," Frank laughed.

"Oh, don't try to get a big head about things. You forget, I was already tired from skiing."

"Potato, po-tah-to." Frank continued to laugh lightly as he nuzzled my neck. "Go to sleep, but don't be surprised if you get woken up later on."

"I won't. I know you well enough to know that I need to expect the unexpected." Then I turned my head, pushed myself back into Frank's embrace and passed out dreaming of what the next day would bring.