A Lost Bet Ch. 05
Keywords: Ch., Bet, A, Lost, 05,
1 2 3 4 5 Next
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.
1 2 3 4 5 Next
Keywords: Ch., Bet, A, Lost, 05,