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The School Tramp (From "Boy" to "Boy oh Boy!!") by Mistress Tawny Suede Chapter 1 - The School Tramp I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made. I was nineteen years old at the time and entering my junior year of high school. Yes, my junior year. I had been very sick when I was six and had missed two years of school. So, when I started my junior year, my sister who was only eighteen was starting her senior year at the same high school. Heck, Bigelow was such a small town that there was only one high school. As a result of being sick, I was also much smaller than would be expected. I was only five foot four, and while I was quite strong for my size, I looked very thin and, yes, you guessed it, even a bit effeminate - or cute, as my sister constantly reminded me. She kept telling me I would make a much better younger sister, rather than older brother. She'd always had that idea in her head and that is where the mistake comes in, but I will get to that in a minute. Back to being a virgin, and not wanting to be a virgin.... Becky Winters was the school tramp. She was a senior and was supposedly Dwight Moore's girlfriend. Dwight was the star receiver on the football team. But everyone knew that Becky would put out for anyone who took her on a date. It was said that she'd had sex with almost all the guys in the Senior class and over half of the guys in the Junior class. She was also supposed to have blown or fucked over half of the male teachers at the school, including the principal and vice-principal. I said she'd had sex with over half of the guys in the Junior Class., right? Well, I was not one of them. I was too shy around girls, partly due to my height, and just because, well, I was a geek, a nerd, a nobody. My school marks were terrific - but that was because I had no personal life. I did not go out for any sports, I did not go to school dances or any social events. I was too shy. My only friends were the other guys who were called geeks and nerds by the supposedly hip, cool kids who hung out front of the school smoking all day. I spent a couple days after school in the Chess Club and Math Club with a half dozen other shy and awkward guys. I spent my weekends in my bedroom studying so I could go to University in a couple years, or playing video games online with the geeks from elsewhere who never went outside. Also, I had discovered online porn recently and had easily figured out how to not leave any trace for mom to find when she periodically checked the sites I was visiting. Looking at the pictures, and the videos, made me finally realize that there was something missing in my life. I could not talk to a girl unless she talked to me first. I'd had exactly one date in my whole life and that was with my cousin, Lucille, when her family visited ours last Christmas. And that was a humiliating experience that I will not explain further. I was determined to end my virginity and the best way to do that, I figured, was to go out on a date with Becky Winters. I was convinced that if I did, I would finally get my cock inside a pussy! I was too shy to ask Becky out though and so I asked my sister to help me out, by speaking to Becky for me. I haven't told you about my sister Cassandra yet, have I? As I said, Cassie had just turned eighteen in the summer. She stood five foot eight, had long black hair and a gorgeous face. Cassie had been dating Johnny Long, the quarterback of the football team for the past two years. (And yes, predictably, Cassie is the head cheerleader.) As of a month ago, she had been wearing Johnny's school ring and the two of them had been fucking like animals in her bedroom a couple nights a week ever since. Mom took Cassie to the doctor and made sure she was on the pill. Mom was very open minded and realized that her horny daughter would be banging away with one or more boys as soon as she was of age and so she made sure her daughter was well protected. Mom had even bought me a box of condoms and had THAT awkward conversation with me when I turned eighteen last year. Dad had run out on us when I was only ten and so Mom struggled with raising her two kids. (Mom said he had run off with a woman from the next town, but I had been taunted recently by the Barlow twins who told me that their dad had said my dad was a fruit and had run away with another man!) I'm pretty sure she was disappointed in me for NOT bringing any girls back to my room, but she never said so, in so many words. Oh, my name is Carl by the way; Carl Barton. So anyway, I asked Cassie to get me a date with Becky, the school tramp. I even told her that I wanted the date so that I could lose my virginity. Cassie giggled and turned things around on me. She turned it into a bet. It doesn't matter what the wager was, just the stakes - If I won, then she would set me up on a date with Becky, and would guarantee that I would have sex with her; and if I lost... well, if I lost then she should set me up with the date of HER choice and I would have to do whatever she said on the date, but she would also guarantee that I would have sex. So, either way I would lose my virginity! A no lose bet, right? More like a no win bet, as it turned out! Well I lost the bet of course, and so, no date with Becky Winters. But it did explain why, the next Saturday night, I was dressed in a bra, panties, dark stockings, short short skirt, blouse and two inch heels, with a bracelet on my wrist and wearing clip-on earrings. I was wearing lipstick and eye shadow and my long blonde hair was conditioned and pulled back in a ponytail. I was carrying a small clutch purse which contained keys, lipstick, makeup compact and identification. I was nervously waiting for my sister to come down and join me, to wait for our dates with Johnny and his out of town friend, Kenny. Chapter 2 - The Date When my sister told me I would be going on a date with a boy, it did not surprise me. She could be an evil bitch when she wanted to be (which was often!), and she had always told me I would look cute as a girl. She chose a weekend when Mom was out of town and then got her boyfriend Johnny to find me a date. The day of the date she spent a couple hours getting me ready. I won't bore you with the details except to tell you that after she was finished with me, I was definitely cute - more than cute! I was a knockout. The nerdy boy was gone and the hot girl was revealed. I had to stop looking at myself in the mirror because I kept getting a hard-on in my panties. Not only did it not look becoming for a girl in a tight skirt to have a penis outline, but it kept leaving wet spots that took several minutes to dry! The boys picked us up on time. Cassie introduced me as Sindy, her cousin. I thought she meant Cindy, but she emphasized that I spelled it with an S, as in Sin, since I was a naughty girl all the time! I blushed as Kenny's smile broadened. We drove to our nearby big city, Springfield, twenty miles away. During the drive Cassie snuggled up to Johnny who drove and Kenny and I sat far apart in the back seat making idle conversation. Kenny was definitely cute himself, in a boy way of course and seemed a bit shy. We stopped for burgers on the way and then went to a dance club. The music was seriously thumping inside! At the door we all got asked for ID. I nervously showed the bouncer my Carl ID. He looked me over, smiled, and waved us all inside. The lights were flashing, the bass beat was so low that the floors vibrated, the dry ice was creating clouds of smoky steam on the dance floor. We grabbed a table and the boys went to buy us drinks. Cassie told me not be nervous and just enjoy the night out. I had never been to a place like this as a boy, and I was excited to be here. I sputtered at my first sip of my drink, never having had alcohol before. Kenny laughed. He was even more cute when he laughed. He and I sat talking as Johnny and Cassie went to dance. After ten minutes I realized that Kenny was too shy to ask me to dance, so I grabbed his hand and dragged him to the dance floor. I had never danced in my life, but the small amount of alcohol emboldened me. I was going to enjoy myself, dammit! We were on the dance floor for twenty minutes, that first time - and I ran back to the table several times for more of my drink. Kenny was actually fun to dance with and every once in awhile his hands would touch my wrist, or waist - never for long, but each time it sent a thrill through me. When we all began to get tired, we returned to the table, but just for a moment. Cassie dragged me off to the powder room. Well, we didn't actually go to the washroom. Instead we went outside to the smoking area so that Cassie could have a nasty cigarette. While she smoked, she asked if I was having a good time, and did I like Kenny? I told her yes to both questions. She asked me if I liked Kenny enough to let him kiss me at the end of the date. I'd already been thinking of this, and told her yes. When we went back inside, we discovered that our seats were taken up by a couple of Johnny's teammates and the boys were avidly talking with each other. Cassie bought us drinks and we took them up to the dance floor, put them on a sideboard, and danced with each other for the next half hour. Well, not quite with each other, since other boys kept coming up and asking if they could dance with us. I found it quite fun dancing with different boys - tall ones, short ones. Heck a couple of them were at least in their thirties! These older guys all wanted to dance much closer and had their hands around my waist a lot of the time. I found it strangely stimulating to have guys touching me so much. Two or three of the boys were friends of Cassie, from her senior class. Several of the boys asked if they could call me. I was too polite to say no, but I didn't give out my phone number - I didn't want them phoning Carl! I did let a couple of them give me their email addresses. And I even gave Cassie's email address to a really good looking guy named Jeremy. When I wanted to get out on a date again, he might be... wait, I was thinking of doing this again?!? When I complained to Cassie that the heels were starting to hurt my feet, we went outside for a smoke break again. Cassie giggled at all the attention I was receiving and told me that even after a couple of hours, I was holding up well. My mind was buzzing from the three drinks I had had, and I had to admit that it had been fun flirting with the guys. One of the girls who also out in the smoking area was Becky Winters, the school tramp who I had hoped to have a date with. I realized that I actually looked better than she did!. However she was smoking a cigarette and looking extremely slutty. I was jealous of that look. I was also jealous of her for having a man sitting beside her, his arm around her waist and his lips locked to hers every time she was not puffing on her cigarette. I asked Cassie for a cigarette. She looked at me in amusement but handed me one. She lit it for me. I tried to hold the cigarette like Becky did, and inhaled for my first time. I then had a two minute hacking and coughing fit as Cassie laughed loudly. But I did finish my first cigarette and was determined to eventually be able to match that sexy look that Becky had! Back inside, we danced with the boys some more. Kenny was now much bolder and held my hand a good deal of the time. I squeezed his hand several times and this made him smile a lot. At one point he held me very close and whispered that he was having a great time. I realized with a start that he had a boner and it was pressing against my thigh. I pulled back from him, because I realized that I too was hard in my panties and did not want to be pressing my own cock against him! After awhile we changed partners and I was dancing with Johnny. Johnny was much more handsome than Kenny and a much smoother dancer. While Kenny looked at me with innocent eyes, Johnny stared at me with lust. As we danced, his hands caressed my arms and his hands touched my hips repeatedly. I was definitely getting hot and bothered dancing with Johnny. Deciding to be a bit of a tease, I actually let my hand slide along his pants and I gave his hard cock a subtle squeeze! Johnny gave a startled groan and grinned at me. I don't know if Cassie noticed my "handling" of her boyfriend, or if she was just tired, but she decreed that it was time for us to head home. Cassie was staggering quite a bit. While I had had three drinks, she'd had at least twice that much, as well as some shots that various guys had bought her on the dance floor. Chapter 3 - First Kiss, and more As we drove home, Cassie was sitting as close to Johnny as the two front seats would allow. She was constantly kissing his neck and running her fingers through his hair. From the back it was hard to see what she was doing with her other hand, but it appeared to be in his lap. In the back seat, Kenny and I were sitting side by side with every part of my right side, up tight against his left side. We were holding hands and talking in small whispers. After a prodding glance back from Cassie, I turned my head and kissed the shy Kenny on the lips. He kissed me back eagerly. I had never kissed anyone like this before and did not care that my first kiss was with a boy. Soon our hands were caressing each other's bodies as we mashed lips hungrily. I soon found Kenny's tongue in my mouth and our tongues jostled and played with each other as we took turns sucking on each other's tongues! A few minutes later Johnny pulled off the highway and parked the car along a dark country road. Evidently he and Cassie were very familiar with this spot. My sister and her boyfriend were soon exchanging their own deep kisses. Meanwhile, I found myself laying on the back seat with Kenny lying on top of me. As we continued to kiss, he worked his hand under my blouse and unsnapped my bra. Shortly after, my blouse was undone and Kenny was licking at one of my nipples. Of course, being a boy, I was flat chested, but Kenny did not seem to mind. As he flicked his tongue across first one and then the other nipple, they stood up firmly pert. I groaned and Kenny moved up and covered my mouth with his own as his fingers continued to tease my nipples. I could not see what Cassie was up to in the front seat, but by her position I assumed that her head was buried in Johnny's lap, meaning she was probably sucking on his cock. Well, in for a penny, in for a pound! I could feel Kenny's hard cock pressing against my thigh, and I had quite the stiff rod of my own. I didn't need Kenny shifting position and suddenly feeling my dick pressing against him, so I flipped us around such that I was on top. Kenny put up no protest as I undid his belt, and then his zipper, pulled down his pants and then his underwear. Kenny's cock sprang erect. It was about five inches long and already very messy with all the precum he had been leaking. Kenny muttered something like, oh yeah babe, suck it! Cassie's head briefly rose up and she looked back at me, grinning broadly and nodding at me to go ahead. She watched as my lips slid down on a cock for the very first time, giggled, and then went back to her own cocksucking. I was a boy, dressed as a girl. Should I have been doing this? Um, let me put that another way. I was a nerdy boy, dressed as a hot girl! From the moment I saw Sindy in the mirror, I knew I was going to enjoy being a girl for the night, much more than I had ever enjoyed being a boy. I had decided I would do whatever it took to have the best time possible. I liked Kenny, and I was eager to be the best girl I could be for him. I eagerly kissed, and slurped and sucked on his cock. I bobbed my head up and down and swirled my tongue along that nice warm stick of meat. I had never had a blowjob, but had watched several on my computer. II knew what felt right. Kenny guided me with his grunts and his groans, and his hands were holding my head at times. As I bobbed my head up and down, I looked forward again and realized that Johnny had adjusted the rear view mirror so that he could watch the rear seat action. I gazed directly into his eyes as I took Kenny's cock from my mouth and kissed the head. I then blew a kiss at Johnny who grinned and winked at me. Cassie still seemed to have her head in Johnny's lap, but appeared to not be moving. Moments later, Kenny started breathing hard. His leg muscles went rigid and he panted that he was cumming! I held just the head of his cock in my mouth as he spurted three strong jets of cum into my mouth. Without thought, I swallowed his cum and then I licked the rest of his juices off of his dick head. As we straightened up our clothing, I noticed that Kenny was no longer interested in kissing me. I guess he did not like my cum breath! Johnny was arranging Cassie in her seat. Apparently the alcohol had gotten to her and she had passed out with his cock in her mouth. It was a short drive back to Bigelow. We dropped Kenny off at the house of the friends he was staying with. I got out of the car and we hugged (no goodnight kiss!). He asked if we could call me when he came to town again. I said that it would depend on if I was visiting Cassie at the same time. He gave me his email address, and I gave him Cassie's. He kissed me on the cheek. Back in the car, Johnny and I were both silent and Cassie was passed out. When we got to my house, I helped Johnny get Cassie out of the car, and he took her upstairs. Since they had been lovers for a couple months now, I had no problem with him stripping her and putting her to bed. I waited up to say goodnight to Johnny. I assumed he was not going to stay over, since Cassie was in no shape to have headboard thumping sex with him. As I waited I scrounged in Cassie's purse for a cigarette, and I grabbed a coke from the fridge. Chapter 4 - Johnny When Johnny came back downstairs he was feeling chatty, so I handed him another coke and we sat on the couch, side by side. I explained that I would be sleeping on the couch while visiting my cousins. My aunt was out of town, Cassie was sound asleep in her room and, I assumed, Carl was asleep in his. Johnny made as if to get up and leave, but I told him to sit down, I enjoyed his company. We chatted about the evening and the club. I told Johnny I had a great time and that I had never been to a club like that "back home." He told me that I looked really hot, even better than Cassie had described when she asked him to set me up on a date. I told him that I thought he was pretty hunky and it was too bad that Cassie had dibs on him. I leaned in to him slightly and he met me halfway, our lips meeting in a delicious tender kiss. For the next five minutes we kissed and sucked each other's tongues. My hands roamed over his strong back and then reached for his belt. I giggled and said that I noticed that Cassie had not finished sucking him off, coyly asking him if he would like me to finish the job for him? In reply, Johnny rolled down his jeans and underwear and spread his legs. For the first time in my life, but by no means the last, I knelt in front of a man and worshipped his cock. Johnny had a nice firm seven inch dick and I eagerly engulfed it in my mouth. This was my second cock of the night and it seemed so much more alive - firmer, spongier, tastier. While I sucked up and down its length, my fingers toyed with Johnny's balls. Johnny moaned appreciatively and I could tell he was getting close to shooting his load. But then he pulled my head off of his cock. Johnny pulled me up on his lap and I sat straddling him. His mouth hungrily found mine and we kissed passionately. I felt his rampant cock rubbing along my ass crack. Then he said, I want to fuck you, Carl! He knew! He knew I was Carl, not Sindy. And he still wanted to fuck me! I stood, took his hand and led him up to my bedroom. He explained that he had known who I was all evening - Cassie had explained the bet and during the evening had expressed disbelief to Johnny at how easily I had passed as a girl. I pushed Johnny onto my bed and took my clutch person into the upstairs bathroom. I spent five minutes touching up my lipstick and makeup. I nervously looked through the medicine cabinet and found an old jar of Vaseline which I took with me to my bedroom. Johnny was naked on my bed and he helped me to strip off my blouse, skirt and panties. When my erect cock bobbed into view, framed by my stockings, it did not phase him at all. We kissed some more as he lay me down on the bed. Johnny pushed my legs back and used his fingers to massage some of the Vaseline around and into my asshole. As his fingers pushed inside of me, I felt an electric tingle. He lathered more lube onto his firm cock and then he lay down upon me. We kissed a great deal more until I was feeling comfortable and I told him I was ready. I spread my legs wide as my man placed the head of his cock at the entrance to my ass and then he slowly pushed. At first my anal ring resisted, but suddenly the head was inside me. Johnny paused for a moment to give me a chance to get used to the feeling. Then he pushed some more and slid another couple of inches inside of me. I grunted at the pain, but nodded encouragement at him. He slid back out a bit and then in again, further. Slowly over the next couple of minutes, he worked his cock back and forth, in and out and I got used to the feeling of being so very full. At one point, his cock slid over something inside of me, and I saw stars! A minute later he did it again. I soon figured out how, and where, and each time Johnny fucked into me, I wriggled my bottom so that he rubbed against that same spot. Johnny moaned, telling me that I was so fucking tight! He loved jamming his pecker into my sweet ass pussy, as he called it! I wrapped my legs around his back and pulled his head down for another delectable kiss. My man started fucking me harder and faster. I was moaning and shouting. My nails dug into his back at one point and he howled with pain. I was moaning and cursing him as he pounded away at my ass, his cock rubbing hard along my pressure point. My own cock was rigid between us. Finally Johnny buried himself deep inside of me and I could feel his cum gushing into my ass. My man was seeding me! Johnny collapsed on top of me and then moved his weight onto the bed beside me. His cock slipped out of my ass and lay on my thigh. We cuddled and kissed tenderly for several minutes. After a few minutes Johnny got dressed and I walked him down to the front door. I was just wearing my stockings and heels, the rest of my girl clothes having been strewn around my room. My cock was limp. I kissed Johnny tenderly on the lips as he left. I walked back up to my room, my ass hurting, but in a nice way, as I did so. I looked in on Cassie. She was fast asleep. Johnny's howls and my groans had not disturbed her drunken slumber. I lay on my bed, recalling the evening. I had had a great time at the club, sucked off two boys and been fucked in the ass. What more could a girl ask for on her first date? In all of the excitement of the evening, I had not cum myself. I returned to the bathroom and fixed up my makeup one more time. I then went to mom's room and sat at the end of her bed, looking at myself in the full length mirror. I lit another one of Cassie's cigarettes (I was going to have to get some of my own!). I still wanted to practise that wanton slut look that I had seen on Becky Winters. I posed a couple of different ways and practised blowing out the smoke provocatively. I giggled as I realized that I was trying to emulate the school slut! As I stared in the mirror I saw a sexy blonde schoolgirl, dressed only in dark stocking and heels, with a cute cock sticking out from her groin. I grabbed hold of that cock and beat myself off. As I reached my climax, my cum geysered high into the air several times. I slept well that night, dreaming of Johnny, and Kenny, and Jeremy, and oh so many other boys! Chapter 5 - Lust The next morning Cassie was groggy and could not remember how she got home and into bed. It was a relief to know that she did not have any memory of me banging her boyfriend. I told her I had had a great time. It was pretty obvious to her that Sindy was not just a one-date wonder. She hugged me and said she would enjoy having a part time sister! I helped her to wash the clothes I had worn and in turn she sat down with me and gave me some tips on applying makeup. When she finished she dressed me in some of her smaller clothes, suitable for daytime wear and then she drove us in her car to the local cheap mall and I spent a couple hundred dollars of my savings on a bunch of girl clothes for me - some to be worn daytime, and some hotter outfits for evenings. When we got home, Cassie had several emails from men trying to contact me. She gave me the email addresses. In my room I set up a separate hotmail account for Sindy and replied to two or three of the guys. One was Kenny, one was Jeremy who had caught my eye. I was still walking uncomfortably at school on Monday, but by Wednesday my ass was fine. All I had were the memories of my glorious first ass fuck! I saw a lot of Johnny during the week. He and Cassie were always together at school, always walking hand in hand. I found many excuses to talk to Cassie and each time Johnny smiled at me. Once we briefly touched fingers and my heart skipped a beat. My email conversation with Kenny faded into nothing in a couple of days. He had gotten what he wanted from me. I was already learning about men! But, I talked to Jeremy a few times by instant messenger online and agreed to meet him for a date on Saturday night. Cassie agreed to help sneak me out of the house, since Mom was going to be home. I spent a nervous hour putting on my makeup and then my panties, stocking, bra, dress and heels. I had bought a larger bra and filled a couple of balloons with bird seed to give me a larger bosom. I made sure to not fill the balloons very full, since I was still a developing girl! Cassie helped me put my hair in a ponytail again and then distracted mom as I left the house and hid in the back seat of her car. Cassie came out and a couple blocks away I hopped into the front seat with her. We shared a cigarette as she drove me to my date. Jeremy lived in Seneca, the next town over, and he met me at a small restaurant. Cassie drove off for her own date with Johnny. We sat in a booth as we ate our meal and talked animatedly. I knew I looked pretty sexy and Jeremy had a hard time keeping his eyes off of me. We each had a drink, and then another - being a boy, Jeremy was drinking beer, but I had a margarita, then a cosmopolitan. Drinking girl drinks was fun! As the alcohol began to affect me, I scooted closer to Jeremy and was soon holding his hand under the table. We then went to a movie at the town's multiplex. As we sat there in the dark, I was starting to feel horny and leaned over and kissed Jeremy on the lips. He squeezed my hand tighter and tentatively kissed me back. Fortunately the theatre was fairly empty and so no one was sitting behind us, to complain of us blocking their view. We ignored the rest of the movie and kissed and kissed. At one point, I rested my hand on Jeremy's pant leg, right on top of his rigid cock, and squeezed. For the next several minutes I massaged his dick and he squirmed and moaned in my mouth. When the movie was done, we hopped into Jeremy's car and he drove to a dark laneway, where we resumed our kissing. I unzipped Jeremy's pants and grabbed hold of his cock. Thinking back, I realized that this had been my goal for the evening. I was eager to try sucking on another cock! I rolled my fingers around the glans a few times, but when I went to suck on it, I realized that my position was too awkward - Jeremy drove a manual transmission and the damn stick shift was in the way. We hurriedly got into the back seat. Jeremy was such a sight, almost tripping over his pants! I then put his cock in my mouth and bobbed my head up and down hungrily. It took only five minutes until Jeremy pushed my head down hard on his dick and he splashed his cum down my throat. As we finished, I licked the rest of his cum off of his penis and teased the head with my tongue. Back in the front seat, we held hands as Jeremy drove me to the local hotel, where I got out in order to get a cab home at the cab stand there. Much as I liked Jeremy, I was not ready to let him know where I lived. He was a gentleman and got out and opened the car door for me. As we parted I turned my head so he could kiss me on the cheek, but he instead gave me a full deep kiss on the lips, with tongue. This was a boy who did not mind kissing a gal with cum on her breath! As I left the cab I looked at my watch. I was late enough that Mom was already in bed, but I still tip toed delicately upstairs to be sure I did not wake her. I stopped off in the bathroom to tidy up my makeup and then sat in my room, wondering why I was concerned about how I looked. Fifteen minutes later, the door downstairs thumped open, and I could hear Johnny and Cassie coming home. Ten minutes after that there was a faint tapping at my door. I opened it a crack and peered out. It was Johnny. I let him in. He smiled at me and then kissed me hungrily. I put my arms around him and we swapped tongues for the next five minutes. Johnny explained that he had made sure Cassie had a lot to drink, and she had passed out as soon as they got to her room. Blue balls again?, I asked Johnny. He nodded and a minute later I was on my knees with his beautiful cock between my lips. Five minutes later I was once again on my back on my bed, and my sweet man had his cock buried to the hilt in my ass. The first time we did this, we had sex. This time, we made love. My eyes smouldered as I made small mewling sounds as his cock drove in and out of me. Johnny whispered about how beautiful I looked, and how fucking sexy I was. We made love face to face, alternating tender kisses and deep tongue probing kisses. My cock was incredibly hard and bounced against each of our chests as Johnny thrust in and out of me. Johnny then surprised me by taking my cock in his hand and slowly running his hand up and down it, pausing to tease the head. I had to stifle my groans of lust to be sure Mom did not hear me! But it was only moments until I huskily whispered, I'm going to cum! Johnny's balls were also churning, and just as my cock spurted its fuck cream, I felt Johnny let loose his own torrent of jism deep in my bowels! We both mewed our love for each other as we spurted our cummies! It took fifteen minutes of cuddling for our heart rates to return to normal. Johnny's cock felt so delicious in my ass, even deflated, and I was disappointed when it finally slipped out of me. Johnny quietly left of my room, and got back into bed with Cassie. I removed the rest of my stockings, etc and went to the bathroom to clean off my makeup. I was back in bed soon and trying to drift off to sleep. But I heard noises from the next room, which I realized was the head board banging against the wall. Cassie had evidently woken up and Johnny was now banging my sister. I did not mind sharing Johnny with my sister. Or course, if she found out, she might not like sharing him with me! Chapter 6 - Skulking around On Monday at school Johnny managed to pass me a note asking me to put together a bag of clothes and makeup and meet him after classes the next day. Now that football season was over, the cheerleaders were practising cheers for the basketball team. Johnny did not play basketball. So he had two hours when he was free from Cassie and he wanted to see Sindy! When the final bell for the day rang, I got my Sindy bag from my locker and hopped in Johnny's car. We drove over to Seneca - just far enough away that it was unlikely any of our classmates would see us - and he got the key to a service station washroom. I spent 20 minutes changing clothes and putting on my makeup and lipstick. We then drove to a local burger joint and had some food while holding hands. Well, we held hands for the first few minutes. After that I was eating my burger and fries with one hand, while my other hand was under the table, squeezing Johnny's cock through his jeans. It was fun watching him squirm and drip mustard from his burger onto his shirt. He got me back by smearing a bit of ketchup on my face when he kissed me between bites. I had a raging hardon of my own in my panties which I tried to calm down when I went to the washroom to remove the ketchup and fix my lipstick. The sun was setting early those days. On the drive back, Johnny found a laneway and we parked hidden from the main road. We kissed frantically for a few minutes and then Johnny suggested we get out of the car. He bent me over the trunk of the car and pulled down my panties. Back at the service station I had lubed up my ass. Johnny stood behind me and slowly pushed his cock into my ass. The previous times we had fucked I had been on my back on a bed. This was my first time being stuck from behind, and standing. I missed kissing while fucking, but Johnny did get even deeper into me than he had before. Wow! And when I shimmied my ass, I was able to get him sliding along that pleasure point. I was seeing stars and he vigorously pounded into my ass pussy! Johnny grabbed hold of my hips and set to jack hammering into me. It only took five minutes and he was spurting into my bowels! My own cock was not stimulated by being squeezed against the hard metal of the car, but I was content, knowing that my man had used me so well! We repeated this again on Thursday after school. That time a farmer drove by us on his tractor, and just waved as he watched the young stud hammer away at his blonde girlfriend! Chapter 7 - Frat Boys Earlier in the week I had told Cassie that I was eager to get out on the weekend again as Sindy but had not yet decided on who to go out with. As far as Cassie knew I had only been dressed as Sindy a couple of times and sucked off my dates each time. When I told her that I had let Jeremy fuck me in the ass (not true, it was Johnny, but I could not tell her that!), and I had liked it, her jaw dropped. She told me that she definitely had to watch me get ass fucked! The next day she said that she had found a college guy to invite us to a frat house party on the Saturday night. Johnny was going to be off doing stuff with a bunch of his friends, so it would be a girls' night out for Cassie and Sindy, and she was sure that I would be able to get as much sex as I wanted! Getting out of the house on Saturday night was easy. Mom had a date and was long gone by the time that Cassie and I were ready to go out. Cassie helped me pick out an outfit that was more risque (can you say slutty?) than any I had worn before. I was wearing a black waist cincher and a short black skirt over black stockings. My heels were four inches this time. Cassie did up my makeup to accentuate my dark eyes. My long hair was again pulled back in a ponytail. I had found a piece of clothing called a gaff. A loop went around my penis head and I then pulled my cock back between my thighs, giving me a smooth front. No erections for me tonight, but also less chance of unsightly bulges. The frat house was in Springfield and Cassie drove, but only after I got her to promise that she would not drink much - she had to be able to drive home! We did each have one drink before we left. In the car, between cigarettes, Cassie pulled out a joint. I had never done any kind of drugs or such before (remember, as a boy, I was a geek!), but what the fuck, I was exploring my feminine side and so we shared a few hits and got a bit giggly as we drove to the party! When we reached the frat house, there were several people entering and we had to wait because they were checking id and stamping hands of the people who were old enough to drink. (Once we were inside no one paid attention to the hand stamps, it was all part of some administration bullshit). The guy checking the identifications was a really cute, bulky blond guy. The only id that I had was my Carl driver's license. He looked at me in surprise as he looked more closely at my face. Then he told me his name was Danny and he looked forward to seeing me inside later. He also told me to be careful. The frat house was huge. It had four floors and a basement. There had to be at least sixty people on the ground floor and I could see more going up and down the stairs. All the gals looked incredibly hot and they were all being pursued by guys. Cassie and I were barely inside the door when we were handed glasses of home made punch. I took a sip and the potent alcohol almost knocked my panties off! For the next hour Cassie and I were chatted up by most of the guys in the place. The music was thumping and we danced with several guys. Most took the opportunity to paw me on the ass and grind their pelvises into my thigh. If I was not wearing the gaff, my own cock would have been rock solid from being around all these hunky men. Cassie's objective for the evening was to watch me being fucked by a guy, and I was eager to get that happening. We could have both dragged just one guy up to a room, but Cassie was extremely horny herself. After about ninety minutes and several drinks, we found ourselves dancing with two hot studs who were both eagerly kissing us and fondling our butts. Cassie grinned and nodded at me. She took my hand and led me towards the stairs. We asked the boys if they wanted to join us in a private room upstairs, and they eagerly followed. It took awhile to find an empty room. We found most doors locked. Those that were open already had a guy and girl fucking or sucking each other. But one of our studs actually lived here and we went up to his room on the third floor. When we got in the room, the guys pushed us back on the beds and began kissing and groping us. After a couple minutes they got off of us and Cassie and I were laying there. My hand touched hers and she squeezed mine. The guys suggested that it would be pretty hot if we two girls made out with each other. Cassie grinned and pulled me to her, her mouth seeking mine. For the next five minutes we traded passionate kisses and our hands wandered each other's bodies. She pulled off her top and undid her bra and pulled my mouth to her tit. For the first time ever, I was sucking on a girl's nipple, and it was my sister's nipple! Cassie teased me by running her fingers along my trapped cock in my panties. I groaned against the teet in my mouth. By this time the guys had their shoes, pants and underwear off. Cassie and I knelt in front of them, and eagerly took their rods into our mouths. Cassie was sucking on Dave's nice 7 inch member, but Bruce's cock in my mouth was a disappointing four inches. Dave pulled Cassie up, pushed her on her back, whipped off her panties, and in moments had his dick deep in her pussy. He was grunting and groaning as he pumped away at her. Bruce pulled me to my feet, but I had to explain to him that I was on the rag that week, so he could not fuck my pussy - but he could have my ass if he wanted. His disappointed frown turned into an excited grin. Cassie pushed her beau off of her, saying she needed to help me. I braced myself against one of the desks in the room. Cassie knelt, and flipped up my skirt and pulled my panties down enough to expose my lubed asshole, but still keeping my cock hidden. Bruce was eager to plunge in to me. Cassie took him in her mouth and bobbed her head on his cock a couple of times to add even more lubrication. She then guided his cock to my asshole and watched as the cock easily sank into my boipussy. Cassie stared fascinated as Bruce pulled back and then sank deep inside me again. Well, as deep as a four inch cock would go. I loved the feel of a cock in my ass, but this one was frustratingly small! Dave had Cassie lean against the desk beside me and he thrust his cock back into her hot quim. As the two frat mates pounded our butts side by side, Cassie and I held hands and kissed passionately, swapping tongues eagerly. Cassie's hand squeezed mine hard as she came twice in quick succession. I was frustrated though. Bruce was enthusiastic, but lacked any technique and no matter how much I wiggled, I could not get his cock rubbing across my prostate with any consistency. One thing that I DID like though was that Bruce grabbed my long pony tail and wrapped it around his hand. He kept yanking on it while he was thumping away at my ass! This helped him get his tiny dick into me a bit deeper. I actually liked the feeling of being dominated in this way! Dave and Bruce both grunted and groaned and then shouted as they came. When they were done, they both left the room quickly, telling us to pull the door closed behind us. Cassie and I rearranged our clothing. As we made our way back downstairs, Cassie told me how hot I had looked. She giggled as she pointed to the cum running down my leg from my messy panties! Chapter 8 - Contest When we reached the ground floor, it seemed like most of the party had vanished. But we followed noises and found the stairs to the basement. As we descended, my heels rapped loudly on the steps. I still marvelled that is was ME wearing those heels. A crying girl rushed past us going up the stairs, away from the crowd in the basement. The basement was mostly one large room and there were about 70 guys and gals forming a circle. One girl knelt in the centre of the circle. A guy was standing in the middle, asking for a volunteer, since the other contestant had chickened out. Several guys were standing around the inside of the circle, looking very eager, but most of the girls were looking at the floor, trying not to be noticed. When the guy mentioned that the winning gal stood to win at least $400, Cassie pushed me from behind and I found myself stumbling into the centre of the circle! I glared at Cassie as everyone in the room cheered. The guy led me to kneel down two feet away from the other gal. I looked at her and realized that it was Becky Winters, the high school tramp. She smiled at me and wiggled her fingers in a brief wave. I smiled back. I was sure she did not realize I was Carl Barton. The organizer explained that we were going to have a blow job contest. Every guy who wanted a blow job had to put in twenty-five dollars and that went to the gal who managed to make him cum, regardless of whether she won or lost. Each of the spectators who was watching had to put in five dollars. The contest would last for twenty minutes, and whichever gal got the most guys to cum, got to take home the spectator money. The interested guys put in their money, and they put their names in a hat. To be fair, names would be drawn at random. Oh, and one last thing said the guy in charge. In order to be sure that the guys actually came, there was no swallowing. The guys had to pull out and ejaculate on the girl's face! Well, I had wanted more sex, and I was in for it now! Names were drawn from the hat and the first two guys stepped forward. They dropped their pants and pulled their underwear down to their knees. Becky and I each had a limp cock hanging in front of our faces . Someone had a stop watch and when they shouted GO, I immediately drew that first cock into my mouth. It took me two minutes of sucking and fisting of that dick before the guy stuttered that he was coming and he pulled out of my mouth and shot three streams of cum onto my cheek. When the second guy stepped forward I saw that Becky had a rope of cum across her nose and was working on her second cock. My second and third cocks were fairly small and I managed to get each of them off in three or four minutes each. The second guy squirted on my chin, but I forgot myself with the third and let him cum in my mouth. I swallowed before I remembered and so he did not count towards my total! As my number four stepped up, the crowd all giggled and clapped. I looked over at Becky to see her mouth up against her man's groin. As I watched she pulled back and a seven inch cock emerged from her mouth. She had deep throated the guy. I had never tried that, but I knew I was going to have to do that soon - but not in the middle of a contest. Becky's face had a good coating of cum on it already. At one point I noticed several people with their cell phones out, taking pictures. Cassie was one of them. I made sure to pose for her briefly at one point, with a cock poking solidly into my cheek and sticky ropes of cum across my nose and eyebrows! My fourth cock was a nice six inches, but he shot pretty quickly. One squirt went into my hair, but two powerful jets of cum hit my left eye. I used my finger to clear my eye, and then licked the cum off my finger. Two or three cocks later, I glanced at Becky again. I saw her working hard on her current cock. The guy she was sucking looked to be pretty drunk and I think he has having trouble staying hard. Becky pulled down her tube top and her large tits popped out. They were gorgeous breasts, though very round and obviously fake. But that just added to Becky's overall trampiness. Becky dragged the guy's cock across her nipples and moaned. Her guy needed no more than that as he suddenly shot his jism across her tits. Becky reached for her next cock as my next one stepped forward. The guy with the stop watch told everyone that there were three minutes left and that Becky and I were tied with seven successful blowjobs each. My next cock stepped forward. He was big. He was black. He was hung. I looked up into the eyes of Dwight Moore, Becky's boyfriend. Yes, Becky's boyfriend had not only brought her to a frat party where she was blowing strange cocks, but he was also participating by being sucked off by her competitor. I could see why a tramp like Becky kept Dwight as her steady boyfriend. His cock was huge. Erect it was at least ten inches and seemed as thick as a soda can. I could barely fit the knob of his cock in my mouth! I ran my hands and tongue along the solid truncheon. I wondered if I would be able to fit that thing in my ass if he ever tried to fuck me! But for the moment, I had to get him off! I twirled my tongue around his glans, and I sucked on the head of his dick while my hands pumped up and down his shaft. The crowd cheered as Becky's guy came, his cum dripping onto her cheek and nose. The crowd counted down the seconds to the end of the twenty minutes, urging me on. I had a hard grasp on Dwight's balls and could feel the tension in his legs, telling me that he was going to shoot, but time was called before he did. I had lost, but I was not giving up. I continued to suck and spit on Dwight's shaft. Now that time was up and his girlfriend had won, Dwight was eager to shoot. He grasped my head and began to shove his cock into my mouth. My hands were gripping his ass tight as he finally shot a thick load and I eagerly swallowed bolt after bolt after bolt of hot jism. I smiled as I stood. The crowd applauded and Becky hugged me. I was handed $175, including Dwight's money and Becky was given her suck money, plus $350 from the crowd. The organizer then offered us each twenty five dollars more if we would lick the cum off of each other's face. Becky declined, but I said I would do it if they gave me the whole fifty bucks. The guy nodded and for the next few minutes I eagerly licked all of the thick jism off of Becky's face, and the cum that had been splashed across her large fake tits. I managed to tease her nipples with my fingers which made her moan. I kissed her on the lips and she eagerly kissed me back. Becky Winters, the school tramp, had kissed me! I collected my extra fifty bucks and everyone moved upstairs to resume the party. I found an empty washroom, washed my face and touched up my makeup. Chapter 9 - Danny The party was in full swing again. Cassie and I got separated on the dance floor and I spent the next half hour dancing and talking with various guys. All the guys were showing a LOT more interest in me and it was hard to keep their hands off of my ass as we danced. Several asked me to go to a private room with them, but I just wanted to dance for awhile. At one point I found Cassie again. Her hair was dishevelled. I wiped a bit of cum off of her chin and had her lick my finger. She giggled and said she had just blown this really cute second year college student. A few minutes later, I felt a tap on my shoulder and turned to face a grinning Danny. Remember, he was the guy checking id at the door? The one I said was hunky and cute? Well, he still was, and I felt my heart beat a bit faster as he asked me to dance. It took only three minutes for him to suggest that we go up to his room. With him I WAS in the mood. I asked if my cousin could come up with us, as she wanted to watch. Once the three of us were in Danny?s room and he had locked the door, Cassie plopped herself down in his desk chair, and Danny kissed me deeply. I wasted little time in getting on my knees, getting his cock out and jamming it into my mouth. Cassie pulled her panties down and was slowly frigging her clit with the fingers of one hand, and was every once in awhile clicking pictures on her cell phone with the other. Danny quickly removed all of his clothing and I realized that below the eyebrows he was completely hairless. He had even removed all of the hair from his cock and the rest of his groin. I found the sight of his bare hairless cock highly intoxicating and I knew I was going to have to do the same to myself! Danny made to remove my skirt and Cassie started to protest. But I told her to relax as Danny knew my secret. As he deftly removed my gaff and my cock sprung free after an evening of neglected torment, Danny admitted that he was gay. Danny pushed me back onto the bed and we fell into an embrace, kissing hungrily. I reached for his cock and he reached for mine. Johnny had briefly fisted my cock once when we made love, but other than that, this was the first time that another person had touched my prick. Danny?s hand was both gentle and firm as he stroked me. I moaned in lust, and Danny moved down my body and took my cock into his mouth. Another first! And oh god, did it feel so damn sweet to have his tongue and mouth moving up and down on my dick. Now I knew first hand why the guys liked it so much when I sucked them off! Danny spun around and presented his own cock to my mouth. I enveloped it hungrily and we were soon both eagerly devouring each other?s cocks. I heard Cassie get up and soon she was taking closeup pictures of my mouth bobbing on Danny?s dick. I tried to get Danny?s shaft into my throat, like I had seen Becky do, but I gagged and could not. I definitely needed practise before I was going to get a dick down in my throat! My own cock was close to shooting and I told Danny. This made him bob his head on my cock more vigorously and shortly thereafter my back arched and I shot my thick load into his mouth. As I lay there panting he reversed position again and kissed me long and lovingly. He pushed my own cum into my mouth and we swapped it back and forth before each swallowing some of it.. Danny reached into his bedside drawer and pulled out a tube of lube. He squirted quite a bit on my asshole and worked it in with his fingers. He thrust first one, then two, then three fingers inside of me, and I realized it felt quite nice to be fingered by someone who knew what he was doing. He had me kneel on his bed and squatted behind me. Cassie moved forward and took the lube and ran her fingers up and down Danny?s cock, making it slick. Wanting a very close view, she then scooted underneath me, her groin at my head, and her head underneath my dick and balls. She squealed in excitement as, just inches above her face, Danny pushed his cock against my anus. The head popped in easily and he slowly sank his entire, beautiful, thick, juicy seven inches all the way into my ass. Oh fuck, did that feel good! Cassie oo?d and ah?d as she watched my asshole pucker outwards as Danny pulled back, my ass trying to hold on to the invader. Her left hand began to frig her clit again as her right hand squeezed my balls. I squirmed and she giggled. For several minutes I was lost in pure bliss as Danny?s steady strokes rubbed his thick rod against my prostate. I shivered in ecstasy. I needed both hands to steady myself against the persistent pounding. Danny had both of his hands on my hips steadying himself, so I was surprised when I felt another hand grasp my cock and start pulling and stroking it. My own sister was jerking me off as a man pounded the shit out of my ass! When Danny noticed this, he pushed my head downwards. My arms collapsed and I found myself with my face up against Cassie?s muff. If sis was willing to fist my dick, I guess I had to be ?polite? to her. I gave her cunt a few tentative licks. She moaned and used her free hand to push my face more firmly into her crotch. But I had taken only a couple of licks before Danny changed things around. Grasping hold of me, he rolled over on his back. His cock slipped out of my ass. He told me to sit on his cock. This was new for me, being on top. I steadied his cock with one hand as I lowered myself on his dick. It slid inside me easily but when I bent down to kiss him it slipped out again. I turned around with my back to his face, and dropped onto his cock again. This time, he slid inside and stayed. In fact, my weight dropping on his cock, drove his dick deeper into me than any cock had ever been before. With his strong hands under my thighs, Danny helped me to bounce up and down on his dick. I was seeing stars as his dick ran across my prostate. Cassie was on the floor taking pictures of the lewd sight on me dressed as Sindy (well, undressed as Sindy!) bouncing up and down on a man?s dick as my own stiff rigid rod bounced around wildly. Suddenly Danny?s strong hands held me positioned in mid air and he furiously rammed his cock in and out of me. He screamed that he was cumming and I felt my bowels being washed by his cum. My own dickie let loose and I fountained six or seven streams of goo high into the air. We collapsed on the bed, both of us gasping for air. As we started to regain our breath, Danny reached into his bedside drawer again and pulled something out. As his softening cock slithered out of my ass, he pushed a butt plug up inside me. I had never seen one of these before (and would not actually see this one until I got home.) As he kissed me, Danny suggested that I keep the plug in my ass until I got home. That way I could enjoy the feeling of his cum sloshing around inside of me for awhile longer. We were momentarily distracted by soft moans from the floor. Cassie had just frigged herself to her own climax, and collapsed giggling onto the carpet. Danny and I exchanged email addresses before Cassie and I straightened ourselves up. Danny decided that he was just going to stay in his room for the rest of the night. As Cassie and I descended once again to the ground floor, I was walking strangely, due to the plug in my ass. And of course, because of the pounding my ass had just taken. The party was winding down and we decided to leave. We paused outside to each have a cigarette. As we smoked, Cassie told me that I had been utterly, fucking amazing! When she had suggested that I dress up for one date, she had never thought I would turn into such a cock hound! I blushed at the term, but had to admit to her that I enjoyed being a cock tease and was eager for more outrageous experiences! Carl had been boring for SO long. Sindy wanted excitement! As we ground our cigarettes under our high heels, Cassie gave me a long passionate kiss and we swapped tongues hungrily. She gave my cock a gentle squeeze and then we hopped into the car. On the way home, I made sure she stayed awake behind the wheel. At one point she confided in me that over the last few weeks Johnny had been hinting to her that he would like to try fucking her in the ass. She had no idea why that idea had suddenly come into his head (of course, I knew why!) and she had resisted any suggestions. But after watching me enjoy it so much...... My ride home had been a bit uncomfortable due to the butt plug in my ass. I had squirmed about on the seat a few times. When we got home I headed straight for the bathroom. It took me a few tries to properly grip the base of the plug so that I could pull it out. Thankfully I was sitting on the toilet because as I got the thing out, Danny?s lovely cum slid out of my ass and into the bowl. I washed off the plug and then brushed my teeth. As I did, I could feel the air wafting up into my ass. Lying in bed, I was very conscious of my ass gaping open. It was not an unpleasant feeling. As I drifted off to sleep that night, I tried to recall the number of guys I had had sex with, but kept losing track. God, I think I was becoming addicted to sex! Chapter 10 - Revelations The next week was eventful. Once again on Tuesday I met up with Johnny after school so that we could share a few moments of pleasure together. I think I enjoyed the kissing just as much as I did the feeling of his long cock stuffed up my pleasure canal! But I was feeling guilty about having sex with my sister?s boyfriend. I needed a steady boyfriend of my own, or rather I needed a steady COCK of my own! Danny looked to be a good candidate for a steady boyfriend, particularly because he had no problem with my cock. We began talking by email and tentatively set up a date for the next Saturday night. On the Wednesday, I skipped out of my afternoon classes and Cassie took me shopping. I had my winnings, or rather ?losings? from the blow job contest, plus some other money I had set aside. First visit was to one of her hair salons and Cassie convinced me to get my hair dyed just a bit more blonde with some silver highlights streaked through it. We also had my eyebrows tweezed a little bit into slightly more feminine arches. My nails were trimmed and buffed and a clear varnish applied. I liked the femme make over stuff, but still had to live my daily life as Carl. Remembering how much I liked Danny?s hairless groin, I also was brave and got a Brazilian wax - all the hair was stripped from my groin. That night when I got home, I posed in front of the mirror and admired my hairless cock and balls. There was something very erotic about the hairlessness and it did not take long before I pulled out my bottle of lube and knelt on the floor positioning the head of my dildo at my ass. The dildo... one of my other purchases. Cassie and I bought me a couple more cute outfits, plus some accessories like fishnet stockings. Our final stop was an adult sex shop where we wandered around for awhile. I eventually purchased some flavoured lube, a couple of shemale DVDs from the discount bin and a seven inch rubber cock. I had always thought of dildos as being long plastic vibrators, and I was surprised to find realistic looking cocks. I wanted one to practise deep throating, but knew it would also end up in my ass a lot. The dildo came with a suction cup base. So indeed that night, I had the dildo attached to my bedroom wall about eighteen inches off the floor and I pushed my ass back on to it and it sank slowly into my ass. For the next ten minutes I pounded my ass back and forth on the fake cock as I ran my hands along my hairless cock. My orgasm was great, but the whole experience left me empty. I needed a warm body attached to that cock! Sadly, Johnny was not able to meet up with me on the Thursday night, so I spent that evening practising my deep throat technique on the dildo. I thought I was making good progress, but the rubber dick did not slide as easily past the pack of my throat as I imagined a real cock would. I resisted sticking the dildo to the wall and ramming my bottom back and forth on it, since Mom had a bunch of neighbours downstairs in the living room, and my groans and banging around might raise too much curiosity! There was one negative aspect to the week. My grades. During the past several weeks Sindy had been taking over my life. My evenings were spent out on dates, or on the internet reading up on girl fashions or browsing porn sites. I had not been putting in the hours of study and homework which had been normal for me. I was an A student up until then, but this week I got back the results of tests in all of my classes and suddenly I was getting Cs and even some Ds! I was going to have to find more Carl time, and let Sindy out a bit less, if I wanted to be able to keep up my grades this year, and next, and get into a good university! But Sindy was having so much fun! A conundrum I was going to have to solve. I wanted the fun, but also wanted the good grades! I had another surprise this week, and did not know if it was a good one or a bad one. Danny and I confirmed our date for Saturday night. Cassie would drive me downtown and Danny would pick me up there. But... he wanted a date with Carl, not with Sindy. Danny said he was gay and was interested in guys, not gals, and so he wanted to spend time with me as Carl. I was a bit taken aback, but agreed. On Saturday night I shaved and showered and put on some nice boy clothes. Boy, was it different getting ready as Carl. Half an hour tops to get ready, instead of the two hours that Sindy needed! Mom was a bit taken aback by my new hair colour and fresh scrubbed appearance, but was thrilled that I was going out on a date, though I did not tell her it was with a guy! I do think she wondered though.... with my more feminine hair and eyebrows, she might be having thoughts that her son was discovering he was gay! Hmmm..... It didn?t help that I was walking with a bit of swish to my step too. Carl had asked me to wear the butt plug he had left inside of me the previous weekend. So after my shower I had lubed up my ass and slowly shoved the plug up inside my rectum until my anal ring had clamped around the base. It was both pleasant and unpleasant to be walking around with that thick plastic stuck inside of me and, indeed, it was difficult to walk straight. Mom?s own date picked her up just a few minutes before Cassie and I left. I was surprised to see that it was Mr. Henderson, the principal of my high school. That made me very nervous, but I realized it was a reaction to his authority. It was like Mom was dating the enemy! Mr. Henderson was a widower whose wife had died about eight years ago, before he had moved to Bigelow and taken over as principal at our school. I knew this because his son, Stevie Henderson was in my junior class and we were friends. His daughter Karen was in Cassie?s senior class and those two hung out together sometimes. I knew Mom had more than one guy who she was seeing. I guess she was serious enough about Mr. Henderson since she had an overnight case packed. Apparently the two of them were going out of town to see a Sunday football game somewhere far enough away that they would not be back until late the next evening. I haven?t really told you anything about my Mom yet, have I? Well her name is Miriam Barton and she is about 5 foot 5 with long dark hair. She is attractive, but not gorgeous. Her best feature, to my mind, is her long legs which she is not shy about showing off, either by wearing short skirts or by wearing patterned stockings. As a nerdy teenager, the occasional glimpse of my mom?s dark stockinged legs over the years has been about the only sexual thrill I ever got in person. Cassie has obviously taken after her, which has disappointed her because both have not got much in the way of tits. Mom had a tough time raising two kids but we seemed to b