A Lost Bet Ch. 05


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.

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