14 comments/ 86418 views/ 86 favorites A College Sissy Ch. 01 By: nat_rose For some reason I decided to go away to college. Like, a plane ride away from home. I guess part of me thought it would be good to separate myself from high school and my friends and family and start to explore who I really am. That's what college is all about, right? So after all was said and done, I decided to accept an admissions offer from a big state school in the south. When August rolled around I said goodbye to my friends and hopped in a car with my parents and my girlfriend, Emily. Emily would be finishing her final year of high school back home while I was away, and made me promise and promise and promise that we'd stay together while we were apart because so many couples split up in the first year of college and we just couldn't be like all the rest. Right I mean Emily is great. She's absolutely gorgeous—long, straight black hair with bright blue eyes. She's funny and smart and we lived just a couple houses away so it was always easy to sneak out and hookup in a neighbor's front yard or some other place. She had great style, too, arty yet sexy, unafraid to try new looks with her makeup or test the boundaries of both the school dress code and her snobby hipster friends who thought you couldn't be self-respecting if you dressed like a tart from time to time. Emily's fun and she plays in a million different worlds, and I'm attracted to that. If we truly make it, I'll be happy. Let's leave it at that. So we hop in the car and head off on the long ride to school. Emily and I are in the backseat the whole time, and I can tell she's getting sadder as the mile marker ticks lower and lower. We arrive at campus bleary-eyed, her from the emotion of it all; me from it being a long damn car ride. We check into a hotel, hook up for what might be the last time and get to sleep. In the morning, I check into my dorm. It's a dingy, white-walled cube with shabby furniture. There's a thin mattress on a creaky wooden bed, and an old wooden desk on my side of the room. It's duplicated on the other side for my roommate, whom I haven't met yet. Emily spends half her time looking at dismay at my subpar living conditions and half her time looking at dismay at the pretty girls walking by in the hallway. "It's OK, babe," I say to try to calm her down. She sits on my bed and starts to cry. "It won't be OK," she says. She's sobbing. "I'm going to go back to stupid high school and you're going to be here and forget I even exist and find some pretty new girlfriend and fuck her every fucking night." I thought maybe she could be right. Ha! What did I say at the beginning of this story? That I was looking for new experiences? You can't say that to your sobbing girlfriend, though. "It won't be like that. You'll come visit every other month; I'll come home for fall break and Thanksgiving. Then I have all winter off." I was working it. "Before you know it, it'll be summer and we'll be together again." Emily seemed to cheer up a little and nestled into my shoulder. After a few minutes of obligatory consolation, we started to clean up the room and put away my things. My roommate wasn't due in for another hour or two and I was hoping to get settled and help him out when he got here. Before no time, the room was looking pretty good so I went down the hall to check out the bathroom. On my way down the hall, I peeked into a room and saw an absolutely stunning brunette sitting cross-legged on her bed in just a tank top and short shorts. She was typing on the computer and looked up at me, probably because I'd stopped and was standing there, leering at her like a common pervert. "Hi! Are you moving in?" she asked. "Uh, yeah. Yeah!" I stammered. She had these stunning eyes with thick long lashes, and she had these wet ruby lips. She'd clearly thought about first impressions. "I'm Abby," she said, putting her computer aside and getting up to shake my hand. She was about as tall as me, and possessed the confidence that all pretty, smart girls have. It was a bit intimidating. "Alex," I said. I shook her hand like a damn woman. "Have you met anyone on the floor, yet?" she asked. "No, my roommate isn't here yet," I said. "You're the first." "Well maybe we could go walk around campus when you get settled," she said. I liked that idea. "I like that idea," I said, my brain working only in elementary school thoughts. I kept staring at her lacy, light blue bra beneath her tank top. She eventually noticed because she looked down and giggled and then arched her back in the doorway. She was that type of girl. I left Abby's room and went down to the bathroom, another dingy amalgamation of tile and outdated fixtures. When I came back to my room, Emily was a bit suspicious. "That took a while," she said. "Just getting my bearings," I said, trying to pass the issue off as quickly as possible. "Whatever," she said. "I had a good idea before we left, let me show you." Emily went over to the desk and picked up a framed photo of us she'd brought. "So you won't forget me," she said. Then she went over to the closet and opened up the bottom drawer. In the drawer was a stack of her clothes—dresses, shorts, tops, bras, panties and a makeup bag. "So I won't have to pack when I visit," she said, smiling. Great, I thought. Not only do I have even less room for my own stuff, now it's fully on display that I have a girlfriend. And a demanding girlfriend, that is. One that I have made a full commitment to. The idea of having Abby over for a quick bang before my roommate came quickly exited my brain. "Love it," I said in my best acting voice. "You're the best." We hugged and after about an hour of tidying, my father came up and told us to say our goodbyes because it's time to hit the road. Tears were shed, me included (it was a big moment, after all), and after a laborious and ceremonial process of hugs, kisses and "I love you's," Emily was in the car and I was back in my room. The feeling was immediate. That I was free. I wasn't expecting to feel a weight lift off me at this moment. I guess my subconscious had guided me toward a positive future, even though I wasn't sure what I was doing the whole time. As soon as I got to my room, I resolved to start anew. I'd break it off with Emily in due time, let her get back to school and be around her friends, but for all intents and purposes I was free to explore. I put the framed photo of us away. I wouldn't be able to look at it without feeling guilty for how immediate my feelings changed. I'd send her clothes back in a few weeks, so I kept them in the bottom shelf. Seeing nothing else to do, and seeing that my roommate had yet to arrive, I walked to Abby's room and knocked on the door feeling suddenly a lot more confident. She cheerfully answered and invited me in while she got her things together. "I hope you don't mind," she said, slipping down her cotton shorts and bending into her closet to pull out a pair of jeans. I was floored. She was wearing a lace white thong that slid smoothly over her pussy and into her ass. "No!" I yelled because I was in shock. "No, what?" she asked, pulling up her jeans. "No, I don't mind," I said. She laughed. "I'm a bit of a free spirit," she said. "I can tell." "A lot of my friends were free spirits in high school, too. We went to school naked once." "Is that so?" I said. "Yeah, all of us in the theater department. I'm a theater major so I guess being weird is part of the job," she said. She took my hand and pulled me up from the bed and we left. I didn't really know how to act around her. I had, however, learned one immediate thing about myself. I like strong women. I'm actually a little submissive around them. Here I was thinking I was in charge of my relationship with Emily, but she basically marked her territory and made me promise a million times to be with her. Even in our relationship, I did whatever she wanted us to do. And I did it happily because I thought, "Well, I'm fucking her. I must be in control." But having Abby so effortlessly take control of my thoughts made me think otherwise. Just because she was pretty, put together, assertive and unafraid to be different, I was several rungs below her in the power structure. I liked not having to make decisions and being told what to do and where to go. To follow and not to lead. Huh, I thought. We walked around for about an hour and returned to the dorm. I noticed my room door was open so I said goodbye to Abby, figuring my new roommate had made it in finally. I hadn't known anything about my roommate until then, except that his name was Bo, which sounded weird to me but I guess was a pretty popular name down here. The dude was big. He was wearing an old cutoff T-shirt and a pair of basketball shorts. I was tall but skinny as all hell, and this guy was taller and much more massive than I was. Helping him move his stuff seemed like an opportunity to show how embarrassingly weak I was. "Hi, Bo?" I asked. "Yup. You my roommate?" he said. "Yeah, I'm Alex." "Alex. Alright," he said with a smile. He seemed pretty easy going. "You need any help bringing stuff up?" I asked, hoping he would say no. "No, I'll be alright. Boxes are a little heavy down there," he said. "Did it so I didn't have to make too many trips up and down the stairs." I'm thinking he declined my help either because he's a nice guy and didn't want to put me to work, or because, as I feared, he just thought I was weak. "You can help me put away some of these things while I go pick up the boxes," he said. It was the latter. I agreed good-naturedly and he left the room to go get his stuff. I started going through Bo's boxes, folding his clothes and putting them where I thought he might like them. I hung up his dress shirts and pants. I arranged his supplies on his desk. Before I knew it, it had been like 30 minutes. Where the hell was Bo? What the hell was I doing? I looked out into the hallway and saw a lot more people moving in and meeting their neighbors. I walked down toward Abby's room at the end of hall to see if I could spot where Bo was, or else make some new friends myself. It seemed so suddenly that cliques were forming. That little groups of guys and girls were getting together and laughing. Almost to the point where I felt like I'd be intruding. Was I in that room for 30 minutes or 30 days? I got to Abby's room and who should I find, but Bo sitting on her bed, flirting with her. Abby was completely different around Bo. She was giggly and girly, twisting her hair in her finger, slapping Bo on the forearm as he made a terrible joke. Bo looked up and Abby twisted her head around, spinning her hair and looked at me like, "Alex, look at this hot guy I just met!" "Hey Alex," Bo said. "You know Alex?" Abby asked. "He's my roommate." "How fun!" Abby said, clapping a little. She was a little girl next to Bo, not the commanding woman I met just a few hours ago. What did that make me? "Hey Ali," Bo said looking up at me, his hand on Abby's lower back. "I don't want to impose on you but do you think you could make my bed? The RA said we have to, and I have to run to orientation soon." "Oh. Uh, sure," I said, a little surprised he would ask that of me. I guess it wasn't that bad. "Ali, I like that," Abby said. I hadn't even processed that. Bo had changed my name to Ali, and now Abby liked it and so that's two people who like it and so of course it'll catch on. So not only was I feeling like I was missing out on making friendships, I had changed my name to Ali and was making my roommate's bed. "Thanks, Ali," Bo said laughing a little. Abby laughed with him. Bo whispered something in her ear as I left, and she said, "No!" loudly and then erupted with laughter. I kept walking, feeling a little shaky about this whole thing. Still, I went back and made Bo's bed. I laid down the sheets, pulled up the comforter. I put the pillowcases on the pillows and fluffed them. I folded a quilt at the end of his bed and smoothed out the sheets. It looked nice, I thought. What the fuck! Why did I just do that? Hours ago I was talking about having sex with any number of my hot female dorm mates. Get out there, man. I kicked the bed out of frustration and headed, with determination for the door. I was met by Abby. "You," she said, putting her finger on my chest. "Me?" "You, Ali, are not going anywhere," she said. She was smirking, almost holding back raucous laughter. "No I'm going out to meet some friends," I said. But I was hopeless and Abby could tell. "No, I have a fun game for you." I squinted my eyes looking for more information. "We're going to give you a once-in-a-lifetime experience. That's what you wanted when you came here, right?" Abby asked. "You told me you wanted to explore this year, right?" "Right," I said. "But I don't know, I kind of want to do it on my own." "You can do that later. Just trust me," she said. She placed her hand lightly on my check. It was totally disarming. She, now again this beautiful commanding woman, had me with that simple gesture. "OK, Abby," I said. "Well that's the first thing," she said. "You're not allowed to call me Abby anymore." "What?" I laughed. "What should I call you?" "Mistress." "Mistress?" "Mistress," she said. "Try it out." "I don't think—." She slapped me. "Mistress," she said. "Sorry," I said. Feeling awkward about the whole thing but not wanting to get slapped, I said, "Mistress." "Good," she said. "And you're name is?" "Alex." "No," she said. "You know what your name is." I didn't really know what she meant. "Umm—." "You know what your name is. Your master said it earlier." I thought and it of course popped into my head. "Ali," I said. "Good girl," she said. "Wait, my master?" "Yes, your master. I am you mistress and your master is busy at the moment but he'll be back to check on you." "Bo?" She slapped me. "Master." "Master," I said. "Good girl." "What do you mean girl?" I asked. "I think it's very clear what I mean, Ali. Master saw your collection of makeup and slutty clothes in the bottom drawer. We think it would be a really good idea for you to experience college as a girl and to make our first year's a little easier and more fun while you're at it." Alright, this has gone too far, I thought. I could be open to new experiences. I didn't even mind exploring this new submissive side of me, but I wasn't envisioning anything life changing. I meant to explore it, like, in terms of friends and school and work and all that, not to be somebody's bitch, let alone my roommate who I've said 10 words to. This is all one big misunderstanding. Those were my girlfriend's clothes and I'm a goddamn man. "No, Abby, this isn't going—" She slapped me in the face and she grabbed my balls through my pants. "What is my name?" she asked, twisting my balls. It was excruciating. "Mistress," I cried. "Mistress!" "That's a good girl, Ali. Now don't fuck with me," she said. "OK," I said, grabbing my crotch and wiping away a tear. I was in pain and actually a bit overwhelmed. "Now look," she said. "If you do everything your master and I say, we'll give you anything you want. You want to fuck me? Follow our orders. You want a little girlfriend? Follow our orders. You want to join a fraternity? Follow our orders. You want some spending money? You want good grades? You want to have any social life at all and stay in college more than one fucking semester? Follow our orders." She placed her hand on my balls again and asked slowly, "Do you understand?" "Yes," I said. "Yes, what?" "Yes, mistress." "Stay here. I'll be back in five minutes," she said." She left and I sat back down on the bed and cried. What had I gotten myself into? When she came back she had a pink razor and a can of women's shaving cream. She handed them to me. "Shave your whole body. Then we can begin." "Then we can begin?" I asked. "No questions, Ali." "I don't even know how to do it," I said. "I've never shaved my whole body." "It's just like shaving your face, although," she said looking at my chin, "it doesn't look like you have to do that much." It was true. She continued, "Go in the shower, take a really long, hot shower, lather up and shave. Make it quick, too. Master will be back soon and we have a lot of work to do." I took the razor and shaving cream and headed for the door. "Ali?" "Yes, mistress?" "You're forgetting your sandals and towels," Abby said, handing me two pink towels and pink thong sandals. Oh god. Now I have to walk down the hallway like this. I took the items and walked out the door. "And don't forget to wear your sandals and cover your little tits with the towel on your walk back. You might want one over your hair too!" I got a weird look from some chick's dad who was still in the hallway carrying those items to the bathroom. I followed Abby's directions exactly. I hopped in the lime green tiled shower stall and turned the water on very hot. I rinsed and lathered my whole body and started shaving from the toes up. I made a few nicks but was remarkably good at it. I had a few hairs on my chest that were pesky but I rid myself of them too. I even shaved my pubes and my asshole, just in case I was going to be under investigation. I couldn't take any more pain. I'm not built to handle that. I wrapped the pink towel around my waist and pulled open the curtain. I immediately shut the curtain, remembering Abby's instructions. I pulled one towel tight around my chest, it hung just below my package because I'm tall, but thankfully it was mostly covered. I didn't know how to do the head wrap so I did my best impression of the Chiquita banana woman and put some 'do up. I slipped on the pink sandals, took a deep breath and headed out. Immediately I was met with laughter. Some guy shaving on the other side of the bathroom caught me in the mirror and whistled mockingly. I scurried out of the bathroom and hustled down the hallway. I made eye contact with two girls in their dorm who giggled and said "Hi!" I waved and walked to my room. "Oh, ho, ho, look at you," Abby said. "You're a pro. Look at those long legs." I looked into the mirror and regarded my legs. They were long. They were tan. They were smooth. They looked good, but whatever. I noticed that Abby had transformed my room. She had removed all of my regular guy clothes from my closet, folded them and put them in a box in the corner. She had taken all of Emily's clothes and hung up the dresses, tops and skirts in the closet, and put the bras and panties in the top drawer. I also noticed that she had added to my wardrobe, likely from her own supply as we were both about six feet tall. She had added lingerie, several tight, bright dresses and few costumes she'd likely kept from past theatrical performances. There was a saloon girl outfit, a lacey Victorian dress and a red latex catsuit. I got a little turned on just looking at all the sexy clothes. That was something that always attracted me to Emily, as I mentioned before, but to all girls in general. It was Abby's effortless sexy look that attracted me to her in the first place after all. Abby had also turned my desk into a vanity. She had a bright lamp, a makeup mirror and all of Emily's makeup laid out neatly on the table. She had also replaced my bed sheets with a light blue satin comforter. "You did all this?" I asked. "Where did you get all this stuff?" "Well, Ali," she said. "Most of it you already had, you little slut you." She was being playful. "I also donated some things from my wardrobe. But I also didn't hesitate to run across the street this afternoon and pick up a few items from the mall with your credit card." A College Sissy Ch. 01 "You have my credit card info?" "Master took it from your wallet while we were out, honey. He thought a girl ought to have more clothes than what you brought when he saw your closet, so he gave me your card and I had a little fun this afternoon." Oh god, I hope Emily doesn't look at my credit card statement. I hope my parents don't, Jesus. "Now that you're all smooth, it's time to get made up," Abby said. "Come have a seat." "What's going to happen when I'm made up?" I asked. "No questions. What did I tell you?" "Do what you say," I said. "Who?" "You, mistress," I said. She was silent, expecting. "And my master." My master, I thought. "Good." Abby said. "Now I'll be doing your makeup the next few nights, but you need to learn so pay attention, OK?" "OK," I said. "Now you have a pretty feminine face already so we're going to highlight those features and minimize some of your more masculine assets. I'm going to make you look hot, OK?" "OK," I said. "Being a hot young girl is a lot of fun but you have a lot to learn about it, so start preparing yourself to fight off guys, to reapply makeup multiple times a day, to go shopping a lot," Abby said. "OK," I said. "Now be quiet. I need to concentrate." "OK mistress," I said. She started to apply my makeup. First a layer of liquid foundation, then a light layer of powder foundation. She began to contour my face, as I'd seen Emily do countless times. After she blended the mix, I started to see an incredibly feminine face emerge. This must be good makeup, I thought. Abby got to work on my eyes, applying a fading colorful eye shadow, going from hot pink to sparkling white near the nose. She applied a little wing of mascara at the outer edges of my eyes and then put on a pair of long, thick fake lashes. She turned me around and told me not to look at my face yet. She then moved down to my lips, putting on multiple layers of goop. She then put a beauty mark on my cheek, I'm assuming, and blended the whole visage with a brush. "Don't look yet, honey," she said, giddy. "OK," I said. I have to admit, that after catching that first glimpse of my feminine face, I was pretty curious to see what I looked like, if not hesitant to see what came after I was all finished. "Now I'll pick your outfit for tonight, but I want you to pick out your bra and panties," she said. "A sexy bra and panties can make a girl really feel like a woman." I had no idea what would look good on me, but I did know what I liked to see. I went over to my underwear drawer and sorted through what had to be two dozen panties and six bras, neatly stacked. Abby had done some serious shopping. I picked out what I thought was the sexiest pair—I don't know why it was so easy—a satin pink push-up bra from Victoria's Secret with white lace and rhinestones, and a matching pair of pink satin boyshorts with white lace and a thin bow above the butt. "I knew you'd have no trouble with that," Abby said. "What a pair to pick." I felt a little embarrassed I had been so eager and decisive in my selection. It was the first time I'd made a decision all day. "Now your master wants you to wear a sexy dress tonight so I picked out a perfect one for your tall, slender body," Abby said. She went to the closet and pulled out a stretchy bodycon minidress with quarter sleeves ("To hide my shoulders," Abby said). It was shiny and light blue, low cut in the back. It would make my ass look even more incredible, Abby said. She was looking at my ass like that? Abby tightened my bra two notches too far and adjusted my chest so it looked like I had small breasts. She put a few dashes of foundation to accentuate curves. Looking down, it looked pretty realistic. She walked behind me and reached into my panties from behind and pulled back my dick and balls. I felt a ball pop and she said, "Perfect!" "When we go out, you'll have to tape this or wear pantyhose, OK?" she asked. "OK," I said. Going out in public was something I hadn't even thought of, but why wouldn't she have that in her plans? Abby handed me the dress and told me to step in. I slid it up my smooth body, over my panties and my new breasts. Abby brushed out the wrinkles and headed to the closet. "Now you need some shoes," she said. "This is the biggest size they had, can you squeeze into a 10?" "I think so," I said. "Good," Abby said and handed me a pair of white heels with light blue polka dots on them. They were really fashionable and looking at the label, realized this probably cost me about $500. The leather was perfectly cut and the shoes shined under the dorm room lights. I put my hand on Abby's shoulder and reached down to put one shoe on my right foot. I had seen Emily and my sisters do this move countless times but it just poured out of me. It was so definitively feminine. I could tell Abby was amused. The shoes were tight but they fit. Abby told me to practice walking around and after a few wobbles, I essentially got the hang of it. I love these shoes, I thought. They were so cute, I thought. How is this happening, I thought. Abby told me to sit and pulled out some jewelry. She put a string of pearls around my neck, "You're a southern girl, OK?" She put a few cheap rings on my fingers and put some clip-on pearl studs on my ears. "Almost done!" Abby said "One last thing." She went over behind the desk and pulled out a long brunette wig. "This is mine and it is very expensive," she said. "This is human hair. It is the best wig you can get. I'm lending it to you because I'm nice and because your master likes long hair. You will start growing your hair out, though, and you will buy a nice wig this weekend. Got it?" "Yes, mistress," I said. I was dying with anticipation at this point. I loved the shoes, I loved the dress, I loved the bra and panties. The makeup I saw looked good. The pearls were cute. I loved all of this stuff on girls, why wouldn't I love it on me? And a beautiful woman is paying this much attention to me? I'll do just about anything. Abby slid the wig on my head and adjusted it. She arranged my hair so that some shiny chestnut locks fell over my left shoulder, some bangs slid from left to right just above my eye and the rest fell to my lower back. "OK, stand up, Ali," she said. I stood and she took a step back. She was silent. She put her hands to her mouth and looked me up and down. I was beginning to feel self-conscious but when she lowered her hands, her mouth was the perfect mix of amazement and giddiness. Like she knew I'd look good but not this good. "Take a look, girl." I walked over to the full length mirror and looked at myself. It wasn't me. It was Ali. Some chick that went away to college and has a new friend named Abby and who wants to rush a sorority. She was a girl that liked to flirt and got a little wild at night. She wasn't afraid to show off her assets and wasn't hindered by any self-conscious flaws in her appearance. She was a confident girl, ready to explore what being a girl is. I looked fucking incredible, to be less poetic about it. I never realized my hips were so wide, my butt so big, my waist so small. Abby had done wonders to my breast and to my face. I was so turned on by the girl I suddenly was that my cock began to get hard, tucked almost into my asshole. I played with my hair, turned around in the mirror checking out my ass. I lifted up my heels and looked at them on me. I was stunned. I looked like a tall Anna Kendrick for Christ's sake. Just simply stunned. "Now," Abby said, snapping me out of my fantasy. "You have one task tonight. You will have more tasks going forward, but tonight is very simple." "What is it, mistress?" "You'll see. Just sit tight. Check yourself out, slut, you deserve it." I smiled and took a seat in the chair staring at myself in the mirror. In one short day, I had gone from guy looking for chicks to chick looking for... well. I don't know what. I'm not gay and have never been attracted to men. I've also never been made up to look like a beautiful woman and I certainly liked this. "I'm going to leave," Abby said. "But I have a few things I need to tell you. Your master is coming back any minute now. He is much more dominant than I am. He will hurt you if you don't listen to him, and I can tell you don't like that. It is in your best interest to listen to everything he says and do everything he tells you to do. Do you understand?" "Yes, mistress," I said. If I got here listening to Abby, who knows what'll happen if I listen to Bo. This isn't the experience I signed up for, but it is one I'm enjoying. "Good," Abby said. "Now when your master is done with you, he is going to go to sleep and you will need to be prepared to wait on him if he needs anything in the middle of the night. You may sleep, but always keep one eye on him. OK?" "Yes, mistress." "You will keep your makeup on tonight, and before you go to sleep, you will change into this nightie, OK?" Abby said, holding up a white silk nightie in the closet. It looked like it would look good on me, I thought. "Yes, mistress," I said. "Oh, I almost forgot," Abby said. "You will wait for him on your knees right here," she said, pointing to a spot on the floor. I obliged. She then reached into the closet and pulled out a thin rope. She came behind me and tied my hands together behind my back. It was tight, and there was no way of getting out of those cuffs. "Remember, do anything he says, OK?" "OK." "You look great, Ali. Can't wait for my turn," she said and left. I couldn't wait for it either, if I was being honest and I had no idea what it would entail. It wasn't ten minutes before Bo burst through the door. He smelled a little like alcohol, and I could tell he was acting a little looser than before. He looked at me on the ground, in a slutty dress, a beautiful woman before his eyes, hands tied behind my back. And he laughed. "What a fucking faggot," he said. "I knew you would be into this." I didn't know what to say. Did he think I looked good? That was the only thought running through my head. "Do I look pretty, master?" I asked. He burst into laughter. Why would I ask that? Why do I care? "You look like some fag in a dress," he said. My feelings were hurt. "There's a lot more to being a woman than dressing up and putting makeup on." "Like what?" "You know what, slut," Bo said. "I can't believe I'm gonna do this." I mean, I'm not stupid. I knew where this was going. I wasn't sure if it was going to be him or someone else having their way with me, but I thought it might also not be that. Maybe they'd just laugh at me or steal more of my money or something. I wondered why he was going to do it if he didn't think I was hot though. And why Abby put so much effort into making me look good if he wasn't into it. "Whatever you want," I said in my sluttiest, most feminine voice. Bo laughed and put his keys on the table. He locked the door and closed the curtains. He came to the front of me. He looked down at my face. I looked up and saw a hulking man. I saw dominance personified. This man was going to make me obedient. He was going to give me purpose. The purpose of getting him off. I was going to be used. I loved it. He spit on my face. "Before we start, a quick photo," Bo said and pulled out his cell phone. "Smile." And I smiled. He threw the phone on his desk and pulled off his shirt. His muscles were carved and he had a bit of hair on his chest. He was a man. This was a man I was going to serve. I licked my lips. "Lick the floor," he said matter of factly. I licked the floor without hesitation. It was clear he wanted to degrade me and I was more than willing to oblige. "Up, slut." He went to pull down his shorts when I noticed he'd been sporting a massive boner. He loved it. He was just trying to make me more obedient. The fact that he was into me as a girl, that he thought I looked hot, was enough for me to do whatever he said. My cock was rock hard tucked in my panties, under the weight of my body, as I sat kneeling preparing to suck my first cock. When he pulled down his shorts, his cock sprang to attention. Before I had any time to look it over, Bo had his big left on hand on the back of my head. I opened my mouth almost instinctively. Maybe I was some whore in a past life. Bo rammed his rigid, massive cock into my mouth. It tasted salty from sweat. It was warm and meaty. It slid right across my tongue and his head tipped the back of my throat. I began to gag, and he thrust again. Bo was raping my mouth and I loved it. He pulled his cock out, now swelling at full erection, and gave me some time to breath. My own spit and his spit from before was now covering my chin and when he slapped me across the face, calling me a slut, the spit shot onto the bed beside us. My knees were starting to burn on the carpet but Bo again thrust his cock into my mouth, this time using both hands on the back of my head for leverage. I started to automatically make the low humming noise I'd heard porn stars make in movies when they were getting deep-throated. It's just about the only sound you can make when you're simultaneously getting chocked by cock and so excited you just need to make a noise. Bo pulled out and the word, "More" just fell out of my mouth. "More what?" he asked, panting. "More cock." "Who am I?" "You're my master," I said. "And who are you?" "Ali," I said. "And what does Ali like to do?" "Ali likes to suck cock." "No she doesn't," Bo said. "Yes she does, master." "No, Ali likes getting guys off however they want." He was right. I'd only liked sucking dick and getting deep-throated so much because it was first on the agenda. With that, Bo lifted me up by the hips. It was easy for him. He bent me over the bed and lifted up my tight dress. He pulled off one of my heels and told me to suck the heel. He said I'm going to need to get used to fucking and sucking at the same time. Bo ripped my panties down and my cock finally was able to surge free. It was fully erect. I was going to blow my load at any moment. But my arms were still tied behind my back and I didn't think Bo was going to be the type of guy to get me off. "You ever been fucked in the ass, Ali?" Bo asked. "No master." "Good." Bo spit on his hand and rubbed into my asshole. I had never played with my butt before and apparently I didn't realize what I was missing. It was like the sensation of a handjob times a hundred. As his fingers lubricated my asshole, I began craving something to penetrate it. It must be the feeling women have when they just want a dude to fuck them. Being on the receiving end was totally helpless but it was also amazing to be getting something and not giving. I felt a sharp pain and moaned. "You fucking slut," Bo laughed. "You love this." It was painful in truth. Bo's cock was gigantic and he was raping my asshole with the vigor that he raped my mouth. I could feel his cock deep into my belly, almost poking the other side. I was a little concerned he was going too deep, to be honest, but I wasn't about to tell him that. I just kept quiet and enjoyed the ride he was giving me. "Say you love it," Bo said, panting heavier and heavier. "I love it, master," I said, heel in mouth, panties at my knees, bent over a bed with a miniskirt pulled over my ass, long flowing, shiny hair bouncing off my shoulder and with my 250 pound roommate pounding my ass. "What do you love?" "I love being a slut," I yelled. I realized our dorm mates could probably hear this. "You ready for your first load of jizz?" Bo asked. "Yes, master, please. Quickly. I want your jizz." Bo pulled out of my asshole and the feeling was absolutely incredible. I feel like I orgasmed for the first time in my life and I hadn't even come. Bo pulled me by the rope to the floor and got me on my knees again. He rammed his cock in my mouth again and I tasted myself for the first time. It was nasty but I loved it for some reason. After a minute of pumping, Bo pulled out and took his massive, bulging cock into his right hand. I closed my eyes. My face was covered in my roommate's warm jizz. I could feel it spray across my face, onto my hair, onto my lashes. It slowly begin to pool around my mouth, and it kept coming. At least 20 seconds of cum ropes landed on my face. I lapped up some in my mouth and swallowed, and Bo laughed. It tasted musky and salty, like I'd always imagined it would taste. It was so warm, too. I immediately craved more so I reached my mouth out for Bo's cock. "No more, bitch," Bo said. He pulled up his shorts and went back to the desk. He took a photo of my cum-drenched face. "So now we have the before and after, don't we?" Bo said laughing. I realized I might be blackmailed by all this, but I was too horny to care and I thought no one would recognize me as such a stunning woman. "We've also recorded all this, so if you don't do what your mistress and I say from here on out, bitch, we're sending it to everyone you know. Including Emily. Including your family. Got it?" "Yes master." Bo pulled a towel from his closet and wiped some sweat off. "There's just one more thing for tonight," he said. I was hoping to god he would let me cum. His jizz was still all over my face and I was getting tastes of it every now and again. "Anything you want, master." Bo pulled down his shorts and came over to me. Were we going to do it again? Please yes. "Open up," he said. I opened my mouth prepared for round two of the throat-fucking and admiring the stamina this man had. I closed my eyes and felt a stream of hot liquid hit me in the forehead, then dart around my face. My master was pissing on me. He was marking his territory and treating me like the lowest form of human imaginable. I started lapping up his piss without thinking, hoping to please him to no end. He had me. "Now go clean yourself up," Bo said when he was finished. "Where, master?" "Where else," Bo said. "The bathroom." My heart sank. Doing this in the privacy of my dorm room was fine. Even being recorded wasn't a death knell. But I could hear people in the hallway talking and laughing. This would be social suicide. I'd get kicked out for being a pervert. "But there's—" "Didn't your mistress tell you to do everything I say?" Bo asked. "You do not want to say no to this." "Yes master," I said. I got up from my knees. My cock was the hardest it has ever been. The cum and piss was dripping off my face and the top of my dress and my tits were drenched. I looked like a whore. I was the whore who got abused on the first day of college. It was me. Bo undid my ropes and I could feel the bruises on my wrists. I put my other heel back on and checked myself out in the mirror. My makeup was still fully intact thanks to some spray Abby had put on. I straightened my dress and tried to tuck my penis into my panties. At this point, I wish I didn't even have one. Bo opened the door and said, "Come back quick." The looks I got walking down the hallway were humiliating. Some girls laughed, some girls were horrifically offended. Some guys laughed and some guys checked me out way too long. One guy grabbed his junk and asked if I wanted a go. If it weren't for my strict orders to return to my master, I would have done anything for that random guy. For more cum. I had been transformed into a complete cock-hungry slut. Before I got to the bathroom, Abby popped her head out of her open door and looked me over, nodding approvingly and giggling. She said, "Get a good night sleep. Tomorrow is a big day for you, Ali." I was excited and nervous. When I got to the bathroom. I went to the sink and wiped off Bo's jizz with paper towels. Some of the makeup smudged, including my eye makeup. I tried my best to get his jizz out of Abby's wig so that she wouldn't punish me. I pulled it apart with my fingers and put it in my mouth. I don't know why I did that but it was like I was suddenly addicted to it. It was a drug. A College Sissy Ch. 01 When I walked back to the room, I heard people whispering about telling the RA that someone had hired a prostitute. Bo was laying on his bed, ready for sleep when I entered the room. I pulled off my dress, took off my jewelry, and kept my bra and panties on to feel as feminine as I could. If Bo and Abby wanted to use me, they would be using Ali, not Alex. I put on the white slip Abby had picked out for me and came to bed. "Do you need anything, master?" I asked. "No," he said. "May I ask one question sir?" "One." He was brief and tired. "May I please masturbate? It'll take one minute, sir. I'm just so horny and—." Bo looked up at me. He got up from his bed, grabbed his computer. He clicked a few buttons and handed it over to me. "You have one minute. You will watch how good a fuck slut you are. You will say 'Thank you, master,' while you're doing it. You will cum into your hand and eat it. Do you get it?" "Yes, sir, thank you." Bo handed me the laptop and I sat on my bed leaning against the wall. Watching Bo destroy me sexually was so hot, I couldn't help but say 'Thank you.' I came immediately and caught a massive load in my hand. I immediately felt silly about the whole night. A rush of guilt flooded over me now that I came. I had just gotten swept up in it. It was a big day. How had I let this happen? I'm a man dammit. This is the last time, I'll go to the RA, I'll tell— "Eat it," Bo said, starting to get up, looking ready to hit me. I looked down and poured the whole load into my mouth. "Show me." I opened my mouth and showed Bo my cum in my mouth. "Swallow." I swallowed. "Turn off the lights." I got up and turned off the lights. Whether I liked it or not, I was Bo and Abby's bitch. This was going to be an interesting semester. ***** Next: Chapter 2: Banging the floor to pay for Abby's tuition; Chapter 3: Tricked by a sorority and used as a fraternity's sex slave; Chapter 4: Cuckolded by my roommate when Emily visits; Chapter 5: Sexual favors to a teacher for a good grade; Chapter 6: Parents' weekend (the finale). A College Sissy Ch. 02 When I woke up the next day I was hit with guilt and shame. Bo was gone and I laid on my back, staring at the ceiling. I was dressed in the white silk nightie, and the pink bra and panties from the night before. My ass was sore from the pounding and my face was caked with leftover makeup. I felt bad physically and emotionally and so I started to cry. This is not what I had wanted and now I couldn't really get out of it. If I said anything to the RA or to my parents, the whole world would think I was some sexual deviant—some pervert who couldn't go away from home for one night before he dressed up like a woman and blew a guy. Abby and Bo had it all on tape, but what was the worst part about it was that I was so willing to do it. All it took was a little attention from a pretty girl and my life was ruined. My mind kept going in circles that morning. Will it be social suicide for me, where I admit to what I did, probably lose a lot of my friends and family, lose my girlfriend and likely have my tuition pulled from my parents? Or will it be social homicide, where I let Abby and Bo take control of me, turn me into whatever kind of sex puppet they want and see where I end up at the end of the year? I picked up my phone and saw a bunch of missed calls from my girlfriend, Emily. She must be going nuts. One night away and her boyfriend was already gone. She must've spent the whole night crying. I couldn't handle the guilt. I decided to call her and tell her what was going on. I'd leave school, start somewhere else in the spring semester and take a mulligan. What was I thinking last night? What was I thinking when I thought I could handle this? As I swiped my phone open, I heard a key enter the door. I turned around and saw Abby enter. I remembered she said we'd be getting started early today, but now I'd made up my mind and I was gone. No more of this. "Hey pretty girl," Abby said. "Abby," I started, sitting up in the bed. She closed the door and looked at me. "You know that's not my name, Ali," she said. "That's what I need to talk to you about," I said. "This is all a huge mistake. I know I was playing along last night but I just can't do this." I started to cry. Abby, to my mild surprise, came and sat beside me on the bed. She put her arm around me and wiped my tears from my cheek. "Shh, baby," she said. "It's OK. We don't have to do anything you don't want to." "It's too late," I said. "I can't be here anymore." Abby ran her fingers through my hair and reach back to pull a tissue out of the box. She dabbed my eyes, picking up the tears and mascara that was dripping down my face. Abby looked me in the eyes and smiled and said, "OK, just relax." I composed myself eventually, feeling no better or worse than before she got in there. "Are you gonna be OK?" she asked sweetly. "Yeah, I just, I just need to go home," I said. "Why don't you lay down. Let's stay in today," she said. I lay down on the bed, getting back under the covers. It was better than whatever she had originally had in store for me. I was really grateful for Abby's sweetness. She was acting like a friend again. "Do you mind if I lay with you?" she asked. "No," I said, a little happier. "Come on in." She stood up and pulled off her sweatshirt. She was wearing only a shiny yellow bra, which propped her breasts up and made them jiggle with each move. She then pulled down her shorts, revealing a white thong. I remembered the image of her pulling her pants down from yesterday, and how hypnotizing the curve of her pussy was underneath her panties. I was staring as she climbed into bed, and embraced me from behind. "Let's just lay here for a while," she said. I was more than happy to do that. Her tender sweetness and physical openness reminded me of how wonderful a thing a friend is, and how loving a woman can be. We dozed in and out of sleep that morning, always with Abby having her arm around me. When we both opened our eyes a few hours later, Abby kissed me on the neck, and asked, "Feel any better, sweetie?" I did. Maybe the night before was just some game she wanted to play. She was a freshman too after all. I mean, maybe this is her form of experimenting and that she wanted the same things I wanted—to make friends, hook up and have a good experience. I could see that. Abby kissed my neck again and slid her left hand from my chest down to my crotch. She rubbed her hand gently over my cock, which was still encased in lacy pink panties. It felt so nice to have this beautiful woman in her bra and panties rubbing my cock and showing me tender affection. I turned around and we met lips. She let me slide my tongue into her warm mouth. She shifted the position of her hand on my cock and started rubbing it with upward motions. It instantly grew to become fully erect, sliding sideways to stay encased in my panties. Abby broke off the kiss and giggled. "What do you want me to do?" she asked. Where was this last night? This chick was clearly into domination and submission equally, which it struck me might be just exactly what I was into. I clearly liked being dominated yesterday, even if things went entirely too far, and I was really enjoying taking control of Abby. This could be the start of a really rewarding experience. "Suck my cock." I said. Abby giggled and worked her way down to my dick. She lifted up my slip and kissed my smooth chest. When she got down there, she kissed my cock through the panties. Eventually she took the tip her mouth while it was still encased in the silk, and then pulled the edge of my panties over the cock. My erection sprung free and Abby kissed the shaft up and down sweetly. I put my hand on the back of her head as Bo had down to me the night before and she engulfed my entire cock in her mouth. We simultaneously moaned in delight. I looked down and was enraptured by the sight. A beautiful brunette in a lacy yellow bra and thong taking my entire dick in her mouth. She looked up at me with her stunning eyes and I knew I was close. I wanted to blow my entire load into the back of her throat and prove to her that I wanted to be dominant now and again. If she wanted to see if I could hang, switching control back and forth, as some sort of test to see if I could be her boyfriend, I'd show her. "You ready, bitch?" "Mhm," she murmured, her mouth filled with my cock. I prepared to shoot my load when suddenly she pulled away. She sat up on her knees, gorgeous as ever, looking at me. "Aren't you going to cum?" she asked. "Aren't you going to finish, bitch?" I asked, trying on a dominant voice. She laughed. "No," she said. "Well, yes. But first you have to earn it." Here we go again. "What do you mean earn it? I told you I'm not doing this anymore," I said, sort of lying because I was on the edge of cumming, with a stunning chick in front of me and I would've punched my mother for her to suck me for just 10 more seconds. "You do everything I say today, and I'll finish you off," she said. "What do I have to do?" I said. "It's nothing like last night," she said. "Can't you just finish me now and then I'll do whatever you want?" I said. "I can't trust you to do that yet, dummy," she said cutely. "How long will I have to wait?" I asked. "Oh, not long, we'll be back before dinner," she said. I thought. "Do I have to go out dressed as a girl?" I asked. "Nope," she said, smiling. "OK, let's do it," I said, feeling like I'd won a small victory and excited to see what this new version of Abby had in store for me. More than anything, I felt like I had 50 times the amount of my normal testosterone and adrenaline coursing through my veins, imploring me to do anything necessary to get off. "Clean off your makeup and put on some boy clothes. They're in the box," she said. "I'll be back in 20 minutes to pick you up." I got up from the bed when Abby left and pulled down my panties and lifted off the slip. I undid my bra and placed everything in the clothes bin. I pulled out a pair of boxers, jeans and a T-shirt from my boy clothes box and put them on. I grabbed a hat and pulled it low over my face so no one would have to see me in makeup while I walked to the bathroom. I washed off all of Abby's work, peeling off a few bits of dried cum from the night before. I finished cleaning and went back to my room to wait for Abby. She came by a few minutes later and entered the open door. She was wearing a pair of black shiny leggings with a loose black tank top. She had her hair in a pony tail and her makeup was minimal but striking. She closed the door, undid my jeans, pulled down my pants to my knees and started sucking again. I immediately regained a full erection and felt like I was on the edge. I grabbed Abby's ponytail and forced her head down the full length of my shaft. This was it. "I'm gonna cum," I said, loosening my grip on Abby's hair. She pulled off and said, "Alright, pants up. Let's go." She said it so matter-of-factly and had switched gears so easily from cockslut to mistress that I stood a little dumbfounded. She had turned on that switch in men that makes them do irrational shit if they don't cum. It's an overwhelming feeling, to be on edge for a long period of time. Your mind becomes locked solely on pleasure and there's an incredible energy that transforms you into somebody on a mission. The thing is, I didn't know who was in charge anymore. I was back dressing and acting like a guy with a beautiful chick sucking my dick every 20 minutes, but here we were going to do whatever it is she had in store. She'd changed the chemicals in my brain to control me through my dick. The difference between this and last night, though, is this is the type of control I can get behind. We hopped in Abby's car and drove about 20 minutes to the big mall on the other side of town. "Now look," she said as we got out and started walking toward the entrance. "You have to do whatever I say and only then will I blow you, OK?" "OK," I said. "What are we shopping for?" "You," she said. She pushed me up against the nearest car and stuck her tongue deep in my mouth. She took my hand in her hand and slid it down the front of her shiny leggings. I felt the warmth of her pussy and started fingering her. She moaned and leaned back from our kiss and bit her lip. An old couple walked by and I pulled my hand out and we giggled. I was rock hard. "Anything I say, got it?" she asked. "Got it," I said, so goddamn turned on. "No questions asked or the deal is off," she said. "Let's go," I said, ready to get over whatever she had planned. We walked into the mall. It was a Saturday and the early afternoon so it was pretty busy, mostly packs of high schoolers and other college kids. Abby slipped her hand into mine and started to lightly pull me in directions. We veered off the main walkway into our first store, Victoria's Secret. The whole place was a tart's dream. Pink interior with satin wall fixtures and chandeliers. And of course all the lingerie, bras and panties any girl could want. There were packs of young girls walking in and out hurriedly through the store. We stopped in the doorway. "OK, so here you're going to pick out a bra, a pair of panties, a garter belt and some stockings," Abby said, letting go of my hand. "Are they for you?" I asked. "Yeah, they're for me," she said, laughing. "Were you not there last night?" "Abby, I told you, I wasn't going to do this," I said. "And I told you I'd let you cum in me if you did everything I said without any complaints," she said. She leaned over and started to whisper. "Now we can leave right now, go back to the dorm, post that video of you dressed up like a sissy slut blowing your roommate on Facebook and you'll never get to touch me again. Or you can do what I say and I'll finish you off." My brain said no, but cock said yes. "OK," I said. "Good girl, Ali," she said loudly. I blushed when a couple girls looked my way. "Now this is what you're going to do. You're going to go up to that cute salesgirl and asked to get measured." "Abby," I started. "Listen," she said firmly. "You're going to get measured, then you're going to pick out your lingerie. You will hold up several pairs of panties to your waist to see how they look. You'll ask the salesgirl if you can try your little girl clothes on. Then when she asks if you're doing alright in the dressing room, you will say 'Yes' and ask if you can wear the clothes out." I looked at Abby and exhaled. "You want this," she said. "You want me." "Are you coming with me at least?" "Nope, I'll be on the bench out here making sure you're doing a good job." I sighed and walked into the store. "Can I help you sir?" the young salesgirl asked. She was wearing tight black pants and a black shirt, and obviously a push-up bra from the store. I looked at Abby who gave me a "go ahead" motion with her hand. "I was wondering," I whispered, embarrassed, "if, uh, if you could measure me for a bra and panties." The young blonde with perky tits laughed in my face. "Uhh, if that's what you want, hun," she said. "You serious?" "Yeah," I said, blushing. She laughed and started walking toward the back, waving me with her. "You get a lot of men in here?" I asked trying to make conversation as she took a tape measure to my chest. "Yeah, but they're usually shopping for their wives or girlfriends," the salesgirl said. "Are you gay?" "No," I said offended. "Well then why are you buying a bra for yourself?" "It's complicated," I said. "Are you a drag queen?" she asked. A group of teen girls walked by on their way to the dressing room and one said, "Looking good, girl!" and laughed. "No," I said. "Are you going to a costume party?" she asked. "No," I said, wishing she would just drop it. "Then why am I fitting you for a bra?" she asked. I didn't really know how to answer her. Why was I really getting fit for a bra? I couldn't say it's because a mistress told me to. That's more humiliating than just saying it's for me. "OK, it's just cause I like it," I said. "I'm a crossdresser." "Do you want to be a girl?" she asked. "Yes," I said, exasperated. "Is that good enough?" "I'm sorry, hun," she said. "I was just trying to get you to open up about it." I felt bad about snapping at her. "It's OK," I said. "I'm just a little embarrassed. "You don't need to be," she said, giggling. "You're going to be a 36-A, but if you want to stuff your bra, you can probably get a B or a C." "Thanks," I said and walked out of the back room to pick out my clothes. "I'll be right with you to help you out," she said. As I walked out, I passed display after display of bras and panties. I had no idea which one I wanted, but I just wanted to get out of there so I stopped at the nearest stand that caught my eye. I remembered Abby's instructions to hold panties up to the mirror, so I picked out a pair of lacy black boyshorts, a blue satin thong and a stretchy red pair. I held each up to the mirror and looked self-consciously around. I caught a middle-aged woman looking at me and she quickly averted her eyes. "Do you think any of those panties are going to hide your junk?" the salesgirl asked, coming from behind. "I wore this exact pair last night," I said, pointing to the boyshorts, "and they fit fine." The salesgirl giggled. "How about a bra?" she asked. "I have a bra that'll go perfectly with that blue thong." "That'll work," I said. The salesgirl reached down and pulled open a drawer. Inside was a light blue bra with white lace trim and shiny light blue straps. In the middle was a girly blue bow with a diamond in the center. "Pretty, right?" she asked. "Shall we try them on?" "Uh," I started. "I actually wanted to get a garter and stockings, too." "Oh," the salesgirl laughed. "Big night, huh?" "Come on," I said sheepishly. "OK, OK. You go try these on and I'll bring you a garter and a pair of thigh highs." "Great," I said, taking the bra and thong from her, glad to be out of the main floor. I went back to the dressing room and took the nearest empty stall. I locked the door, took a deep breath and started to take off my clothes. I slide the satin thong up my legs first. When the material reached my cock, I started to get hard. It had been teased with so much all day that the first sign of femininity got it going. I tucked my cock back and picked up the bra. I put it on backwards and then slid it up to my chest. I had fastened it tight, as Abby had done for me, and propped my chest into the cups to simulate breasts. It kind of worked. I was too tall for the mirror and so my head didn't show, but the body that was on display in the light blue satin and lace bra and panties was feminine and hot. The salesgirl knocked on the door and entered my stall. "What are you doing?" I asked, embarrassed. "Oh, please," she said. "I go in with every girl. I can leave if you want." "No, it's fine," I said, letting my guard go down. "It's, uh, fine." "Hubba hubba," she said. "You really look alright, hun." She handed me a matching blue garter belt and a pair of sheer white stockings. She fastened the belt for me, "This would take you forever," and I sat down to slide the stockings up my legs. I'd never experienced the sensation of the stockings on my shaved legs. It felt oddly erotic. The salesgirl fastened my garter to my stockings and said, "There." It looked good and I took turns rotating in the mirror to check out my ass, which looked nice with a satin thong in the middle of it. "Alright, take those off and I'll ring you up," she said. "What name should I put for the register?" "Alex," I said. "Er, no. Uh, Ali." "Ali," the salesgirl said. "Right." "Oh, wait," I said as she was leaving. "I was wondering if it was possible to wear these out?" "Well," she said. "You have to put clothes on top of them so we don't all get arrested for indecent exposure, but sure. Let me just take the tags and I'll meet you at the register, Ali." I put my clothes back on. The outline of my bra was clearly visible through my shirt and my panties stuck out when I bent over. The stockings also obviously popped out of the bottom of my jeans. Oh well, the task was done. I left and paid for my items, catching a few more giggles on my way out. I saw Abby sitting on the bench and she perked up when she saw me. "So I did it," I said, walking toward her. "Can we—" Abby cut me off and lifted up my T-shirt in the middle of the mall to see my bra. She held it there and I tried to push the shirt back down, but she wouldn't let me. "Wow," she said. "Nice choice. I don't think I have a bra this nice." "Abby, please," I said. "Just let me see your panties," she said, unbuckling my pants and peering in. "Oh, wow, satin. You slut." "Are we done now?" "Two more stops," she said. "That's it. We'll be out of here in an hour." I swallowed my pride and took Abby by the hand as she led me down the mall aisle. We arrived shortly at the entrance of Forever XXI. "We're going to go in here and pick out an outfit for you," she said. "We'll have to find something to go with those slutty white stockings, so I'll help you this time." Before I could protest, she took me by the hand and dragged me into the store. I didn't care anymore at this point. The humiliation at Victoria's Secret was about as much humiliation as one guy can get, so this was all a cakewalk. It's like when you win the lottery, picking up a dollar on the floor seems meaningless—I'd reached my humiliation capacity and my ability to feel shame was broken. In a way it was liberating—to not care what people thought of me. Plus, at the end, I was getting a blowjob. And most of all, I think Abby was really into this and pleasing her seemed like what any respectful boyfriend would do. Am I making this seem more normal than it is? A College Sissy Ch. 02 "I got it," she said, excited. "To commemorate the loss of your virginity, we'll put you in white!" "Whatever," I said. Abby pulled off a couple white dresses and held them up against me. Some of the older girls in the store were looking at me and were a lot more judgmental than the ones at the other store. Eventually Abby decided on a stretchy, tight cocktail dress, with thin shoulder straps and a miniskirt. It had cream and white colored sequins on it, which made it sparkle. The back of the dress went all the way up to my nape, but the neckline in front was low. "Good thing you got a push-up," Abby said. "Let's go try it on." We went into the dressing room and I took off my clothes. Abby smiled when she saw me in the lingerie. She helped me into the dress. She had gotten it in the largest size, because I'm so tall, but it was still a little short. It reached to just below the top of my stockings. Anytime I bent over in the mirror, the light blue garter strap would show. "This is going to be good," she said, adjusting the straps up top, which were about an inch thick and hid the bra straps underneath, at least while I was standing still. "I'm going to go get you some shoes, stay here." Like I was going to go somewhere. I danced around in the mirror, running my hands over my new curves. It all felt good because I was being held in some tantric sex state thanks to Abby, and my cock began to get hard again in my panties. Abby came back a few minutes later with a shoebox. Inside the box was a pair of velvet blue heels, the kind where the fabric turns them into wedges. They were hot as hell. I slipped on the pair and kicked up my heel like a girl in the mirror. Abby clapped enthusiastically and said, "That's a look." "Do I have to walk out like this?" I asked. "What do you have to be afraid of?" she said. "Uh, looking look a fool," I said. "Babe, you look better than I do," she said. She same over and pressed her body up against mine and kissed me deeply. She then got down on her knees, lifted up my dress and pulled my cock from the satin thong. She took it in her mouth and I felt that energy again—that energy that made nothing else in the world matter besides blowing a load inside this girl's mouth. She pumped a few times on my dick and pulled back like the last time. I was kind of enjoying the energy at this point. "I'll go pay for this. Meet you outside." I waited for my boner to subside a little and slid it half-erect back into my panties, which almost made me cum right there. The heat of my dick touching my asshole reminded me of the pleasure I felt last night when I was getting pumped in the ass. For as much as I felt guilty about it, there was no denying the pure physical fact that it felt incredible. I pushed open the door and walked out to the store entrance. Abby kept me waiting for a few minutes, so I stood on the corner, trying to pose as feminine as I could. If I was going to look like this, I'd rather try to come off as a girl, or something like that, rather than fight it and humiliate myself as a man. A few young girls came by and started a conversation with me, clearly wanting me to be their gay friend and help them pick out clothes. Abby came out and said, "Alright girls, Ali's got an appointment, she'll talk to you later." Abby took me by the hand and led me back into the mall. I still looked like a 6'4" freak man in my heels and without a wig or anything, but the sight of us two together definitely turned some guys' heads. Maybe they were just wondering what a hot chick was doing with the tranny. "One more appointment for you, little miss," Abby said, pointing to the Sephora makeup store. "Go in, say your name is Ali and that you have a makeup appointment. I'll be downstairs at the kiosk picking out a wig for you. No more cum in mine." I walked into the Sephora glad that this was not only my last duty before I could fuck Abby, but glad that makeup and a wig would be added to my look so that I could at least hide who I was. Everyone could've seen Alex, the freshman dude, wearing a dress and shopping for panties. Who knows if I'll get recognized in the future. "Hi, I'm Ali, I'm here for a makeup appointment," I told the nearest salesperson. "Ali!" the girl said. "Right this way. We've been waiting for you." I sat down in front of a big, lighted mirror and two makeup artists came over to work on me; one guy and one girl. They chatted about what the best thing would be for me, saying I had girly cheekbones and a feminine chin, but that my eyebrows were a problem and they needed to make my sunken eyes pop. They just assumed I was a girl. Rather, they treated me like a girl. It was refreshing to not have to explain it to other people and to just be accepted for what I was. What I was. Who knows what that is. They got to work, applying layer after layer of makeup. In thirty minutes, they had done their job and stood back feeling accomplished. What I saw in the mirror was different than what I saw last night. They had transformed me. As I was marveling at the look, Abby came up behind me and put a long, dark brown wig on my head. It had some wave to it, and fell just below my shoulders. The makeup guy then went behind me and started arranging the hair. He tossed much of it over to one side, brushed it out, clipped some parts and eventually pulled the whole thing back into a loose bun with a large bang running down the left side of my face. It was elegant and feminine, and I loved the look. "Well done, guys," Abby said. "Anything to say, Ali?" "Thank. Uh, thank you," I said, still admiring myself, now fully turned on by the image in the mirror thanks to the level of arousal I'd maintained all day. "She's excited," Abby said. "She has a big night." "I bet she does," the guy said. "Good luck, honey." "Thanks," I said, mindlessly. I walked out of the store with Abby and the looks were different. I was still self-conscious and obviously I wasn't a woman. I was too tall and my shoulders were too broad. I walked like a man, too. But I embraced this new identity. This person who took femininity to a new level. Who, though he isn't a woman, chooses to embrace the things that make women so beautiful. It was sex that I was selling. Feminine power that only comes from being able to make guys do whatever you want because they think with their dicks and not their brains. And that's when I looked at Abby and realized she had turned me into her. She was my sister, not my fucktoy. This was the big game, and my suspicion early on that this was all a rouse, that nothing had changed and that she was always in control, was correct. But I experienced it first hand now. I didn't need to be told or scared into it. I wasn't operating out of fear anymore; I was operating out of my own free will, powered by the electric energy of sex she was charging me with. We got into the car, and every time I caught myself in the mirror on the drive home I remembered what my relationship with Abby had become. She was my sister, my mistress, my girlfriend. But more importantly, she had transformed the way I think. The trip to the mall was some diabolical genius on display. "Are you ready for tonight?" Abby asked. "What's happening?" I asked. Abby smirked and took her eyes off the road for a second to look at me. She looked back at the road and put her hand on my knee. "We're going to a fundraiser," she said. "Oh, where is it?" I asked, realizing why Abby had put in so much effort to make me look good. "Just in the dorm," she said. "It's a cause you'll feel very compelled to support, too." "And what's that?" "You'll see, deary," she said playfully. I chuckled to myself, embracing the affection from Abby, eager to please her and a little excited to live a night in public exuding my newfound acceptance of femininity. We got back to the dorm as it began to get dark outside, early in the evening. Abby parked the car and told me to wait before we got out. "Now, look," she said. "The fundraiser just started so just get ready to act the part, OK?" "OK," I said. She slipped her hand under my dress and between my legs, digging for the cock that I had buried in my panties. "I could barely find it," she said. "It's like you don't even have one anymore, Ali." I felt the energy I had felt all day while Abby was teasing me. "Do you think you might be able to finish what we started earlier?" I asked. "I could," Abby said. "And if you want me to, I will. A promise is a promise." She pulled out my cock and started stroking it slowly. It began to get hard. "But," she continued. "Don't you feel really good right now?" "Yeah," I said. "Actually I do. It's this crazy energy, like being on a drug." "Yes, baby," she said. "That's it. I'll tell you the truth and the truth is that the longer you wait, the more intense your orgasm will be when I blow you. Plus, all this pent-up sexual energy might make you more flirty and fun tonight, don't you think?" "I can see that," I said smiling. "Here's one more taste to remind you," Abby said before she lowered her mouth again onto my cock. Looking down and seeing my slutty outfit, my shaved cock sticking out of panties and this gorgeous girl blowing me was the perfect reminder of this crazy experience I was having. Abby pulled up and kissed me lightly on the lips. She slid her tongue into my mouth, parting my lips. I tasted my own salty precum and remembered the erotic taste of Bo's that I had last night. It was like a synapse had been formed in my brain that now connected the taste of cum with intense sexual pleasure. Abby was a mastermind. "Alright, Ali," she said. "Let's go." I tucked my cock back into my panties and got out of the car. I had gotten used to walking in the slutty wedges by then and my walk had become a little more feminine because of it. "Now when we get up there, you'll see where to go, but we'll probably get separated," Abby said. "OK, well will we talk at all tonight?" I asked. "I'm sure we will," she said with a smirk. We walked into the dorm and the RA on duty leered at both of us. He was a repulsive looking guy in dirty clothes, and he had an unkempt beard. He looked once at Abby, who winked at him, and then looked at me and smiled. "Ladies," he said. "Hi," I responded in my girliest voice. I guess I had done it automatically to try to fit in as a girl, even though I knew I looked like a tranny. "See ya later," he said. We walked by and got into the elevator. "Ready?" Abby asked. "I think so," I said, unsure of what was to come. Abby pressed the B button in the elevator, which only had the laundry room and a dank storage space. There couldn't be a school event here. Maybe she just wanted to pick something up. When the door opened, Abby put her hand on my back and pushed me out. I tripped over my heels and fell on the fround. She stayed in the elevator and waited for it to close. I looked up as she said, "Have fun." I stood up and turned to the laundry room where I saw a group of guys hanging out. There were probably about 10 or 12 just standing there. I recognized a lot of them from our dorm floor—the guys in the room next to us, that guy who grabbed his crotch when I was walking past him last night. I started to think this was going to be a repeat of last night times about, well, 10. "Hey, sugar," I heard from the laundry room. "Come on over here." I walked over to the laundry room from the elevator hesitantly. I didn't know if I was going to get the shit kicked out of me, or if I was going to get robbed or taken sexually. It was a quick turnaround from the warm, loving day I had had with Abby. "Ali," said a familiar voice. It was Bo. "You're going to help raise some money for your mistress's tuition." "How?" I asked, speaking in a feminine voice. "How am I going to do that?" A bunch of the guys laughed. The room was filled with the stench of sweat—the unmistakable scent of men. The room itself was poorly lit with one long fluorescent light that flickered on and off. The white tile on the floor was cracked and stained. The washing machines were old, and the boys sat on them. "Well, these boys all paid 20 bucks to get their dick sucked," Bo said. "I told 'em you'd get 'em off in two minutes or less or their money back." I swallowed deeply. I contemplated running for the door, but where would I be running? Here I was again, caught in a trap I made for myself. My subconscious really must be a sissy. "But first, you gotta pay for all those pretty clothes your mistress bought for you today," he said. "Abby said she would pay for it, or... at least I thought she did," I said. Bo got up from his chair and stood right in my face. "Who said?" "Mistress, sir." The boys laughed. I wondered if they were here on their own volition or if Bo had strong-armed them into it. When I noticed a few cocks poking through their shorts, I thought maybe they were all here for me. "You've built up quite a reputation, Ali," Bo said. "Everyone knows that my roommate is a little sissy bitch who sucks cock and takes dick in his tranny ass better than any of the girls on the floor." And now there was officially no turning back, I thought. "So seeing that you owe your mistress a couple hundred dollars for your outfit, and seeing that you need to start collecting money for her tuition payment," Bo said, "And seeing that you have this reputation as the fuckdoll to end all fuckdolls... I'm putting your ass on sale for $50." The boys in the room started to laugh. I even heard a couple guys slap hands. "Your two minute time limit still remains," he said. "Now get the fuck on the floor." I did as Bo said and kneeled on the ground. I placed my hands in my lap. My dress rode up a little, revealing my blue satin panties and my stockings. "Who's first?" Bo asked. A short, muscular guy in a wifebeater hopped off the laundry machine and handed Bo a 20 dollar bill. He came up to me and laughed at me. He slapped me across the face. "Hey, slapping's another $5," Bo said. "I'll get it to ya," the muscle guy said. "Let's see this bitch suck cock." He pulled down his pants and revealed a cock about as big as his arm. It sprung to life and I wasted no time in putting it in my mouth, trying to keep under the two minute time limit. The guys started cheering the deeper I got onto his cock. I could feel his dick get even harder and I knew from my own experience that that meant he was about to cum. I was probably sucking him for about a minute before he grabbed the back of my head and pulled me all the way down his cock. I gagged when the tip of his dick reached my throat, and he pulled back the tiniest bit, shooting his warm load directly into my throat. I was breathing through my noise, a trick I'd learned when Bo was throatfucking me the night before, and the sensation of the warm jizz that deep was new. It made me feel like a useless sex toy. All that talk of being a pillar of femininity, a person who chooses to embrace their sexual identity in this new generation that accepts all, was lost. I was just a sex toy for these college guys. The muscle guy pulled off and I caught my breath. But before I got three breaths in, a fat kid with a tiny dick stepped in front of me. "Two minutes starts now," Bo yelled, seeing that I was trying to catch my breath and digest the muscle guy's cum. I took a deep breath and got underneath the kid's belly to his cock. I immediately thought what a fucker this guy is. He can't take care of his body, and he's got the smallest dick. He wasn't a real man. At least I could respect getting taken by a real man. These are the thoughts of a slut, I realized. As much as I hated what Abby did to me on the surface, the deed was done and my brain had changed into a sissy's. I took the fat guy's whole package in my mouth, tasting his sweaty balls, and he said something dumb like, "Look at this faggot." He was the faggot, I was the chick everyone wanted to fuck. "30 seconds," Bo said. I started to work double time, sucking this asshole's cock like I've only seen porn stars do. He put his hands on my shoulders and said, "I'm cumming!" excitedly. "I'm doing it!" It occurred to me that I was probably this guy's first blowjob. When he was finished he pulled back, feeling embarrassed. Embarrassed because he had lost his virginity for all intents and purposes to a tranny whore. The other guys laughed at him and he picked up his pants and left. I swallowed his cum and prepared for the next one. The next guy came up a little hesitantly. I think he was intimidated by me. Why wouldn't he be? I was looking really put together, had just taken the manhood of one our classmates, and was ready to take it from his. I saw the intimidation I felt for Abby from the other side again. I reached out and undid his belt when he hesitated for too long. I ripped down his pants and took his skinny cock into my mouth. He immediately made a sigh of pleasure and kept saying "Oh yes." I worked his cock hard. I realized, this being my fourth cock, which is more than some girls suck in their life, that I liked long, skinny cocks. They had more surface area to taste their manhood, and they were manageable to fit in my mouth. They could also still touch the back of my throat when I wanted to feel used. Here I was pontificating on the types of cock I liked, on my knees, dressed like a slut in a room full of horny guys. And I felt like I was in control in some weird way. The guy with the long cock suddenly pulled his junk out of my mouth and squirted his cum all over my pretty face. Bo immediately got up and said, "Hey! No facials!" The guy chuckled to himself and Bo came over to him. "That's 20 more bucks," he said. And the guy reached into his wallet, pulling out a 20. "And you have to clean her up." "What?" he said. "No way." "Fucking do it," Bo said and punched the guy in the stomach. "You don't cum on her unless you're told to, bitch." "Alright you have a towel?" he asked. "Use your fucking tongue, asshole," Bo said. "Wait, no way," he said. Bo backhanded him across the face. I was kind of turned on that Bo would stick up for me like that. The guy got on his knees and started licking the cum off my face with the tip of his tongue. He gathered up a few wads and went to get up to spit it out. Bo put his hand on the guy's shoulder and said, "Kiss her." The guy looked at me, clearly not wanting to get hit again, and put his lips to mine. I opened my mouth to receive his tongue and his warm cum. He worked his tongue in and out of my mouth, getting all the cum in, and when he was done, he ended it with a peck on the lips. He liked it, that little bitch. I swallowed his load and smiled at him. "Got ourselves a show here, boys," Bo said. "How 'bout we up the ante here." Two guys hopped off a washer as if on queue and one of them gave Bo a crisp $100 bill. One said, "Ready?" to the other like this was some kind of dare. They must've been drunk. I didn't really look at their faces, as I was just focused on their cocks. I still wanted to get them off in two minutes, so when they came over, I took one in my mouth and one my hand. They were already semi-hard and one immediately got as hard as a boner can be. I pulled him out of my mouth and said, "Fuck me," while looking up at him. He looked like he almost came right there. The guy moved behind me and I lowered myself onto all fours. I took the slow-riser into my mouth and started bobbing my head and swirling my tongue up and down his cock. I was going to try giving a beautiful blowjob this time. I wanted it to be powerful yet feminine. Playful, yet dominating. A few love nibbles to let him know I'm there. A few— A College Sissy Ch. 02 Then I got rammed in the ass. Feeling that cock enter me was incredible. It straddled that thin line between pleasure and pain, and I started to moan, my mouth full with his friend's cock. "Hey Bo," the guy fucking my ass said. "Where should I cum?" He was asking my master, not me, where to cum. I guess I owed it to Bo for sticking up for me when the asshole came on my face. "Cum as deep inside her as you can," Bo said. "That'll be nice lube for the next guy." The guy behind me grabbed my hips and started fucking me as hard as he could. My satin thong had been pulled to the side and he was pumping deep inside me. My heels wrapped around his waist. "You ready?" the guy in my mouth said. "Let's do it," the other said. I first felt a wad of cum shoot onto my tongue. I sucked the head of his penis to get everything out, and kept his load in my mouth while the guy behind me started to orgasm. I felt the hot liquid shoot into my asshole and when I leaned up, some of the first guy's jizz dribbling down my chin. I scooped it up with my hand and put it back in my mouth. The guy behind me pulled out and the two left the room. There were four guys left and Bo. I was there on all fours, trying to catch my breath, my belly and ass full of cum. The guys all sat in a row on the washing machines of one side of the room. "Ali," Bo said. "If you get all these guys off in five minutes, we'll let you fuck your mistress." "Yes, sir," I said. I stood up for the first time in a while and wobbled like a bimbo on my heels. "Pants off, guys," I said. "Hold on," Bo said. "I got an idea." Bo went to the corner and pulled out a small table and dragged it to the center of the room. "On your back," Bo said to me, and I did as I was told. I lay down and my cock sprung free from my panties, sticking straight up. "Hmm. One second." Bo left the room and the guys all circled around me. "Which one wants want?" I asked. "I want her mouth," one guy said. "What hand do you write with?" one said. "My right," I said and he moved over to my right. There was then a scramble for my asshole. Seeing two college guys fight it out to fuck my ass was not something I anticipated liking so much. Bo came back and with him was a dolled up Abby. She was wearing a lingerie set—baby pink satin bustier with pink ruffle panties and shiny pink latex leggings with heels. Her hair was still pulled back like this morning. The guys looked at her and one said, "Can I fuck her?" I was immediately put back in my place and felt humiliated. "No shithead," Bo said. "You can fuck Ali. This one's for me." "Hi Ali," Abby said. "You having fun?" "Yes, mistress," I said. "You making a lot of money for me?" she asked. "Yes, mistress." "You ready for that blowjob?" I was floored. I thought this was all a trick. And now Abby was going to come through with her promise after all. These guys were actually kind of nice. This is all just a big game and I was right about us being in a free-flowing relationship. "Yes!" "Well get those guys off and it's all yours." I immediately leaned my head back and took the first guy's cock in my mouth. Then I reached out with my hands and found the other two guys' dicks. I lifted up my legs and gurgled, mouth full of dick, "Fuck me hard." Getting my throat fucked upside down was a new thrill. Getting fucked on my back was even better. I was pleasuring four guys at once. I had all of their manhood's in my control at once. What power. "Three minutes left," Bo said. I took the cock out of my mouth and looked up to see Abby on her knees blowing Bo's cock like a professional. I took the guy's meat back in my mouth and pretended to be as good as Abby was at this. I let the rhythm of the guy assfucking me take control. There was beauty in getting gangbanged. And I was the main beauty. "I'm gonna cum," the guy in mouth said. He shot a load deep into my throat and I swallowed it without any thinking. I pulled the guys I was jerking off toward my head and told them to blast their loads on my face. I could tell they were close so I alternated sucking them from either side. "One minute left," Bo said, his hand on the back of Abby's head like he did to me the night before. The guy on my left starting to shake so I took him into my mouth and sucked down his warm wad of cum. The guy on my right stuck his dick in my face as I was finishing and shot his load onto my mouth. I tried to put both the dicks in my mouth at once and keep it as clean as I could by eating every drop of cum that came out. The guy fucking me then bent my legs up as high as they could go and thrust his cock deep into my asshole. He pumped vigorously for 20 seconds and then pulled out. I could feel the jizz drip out of my asshole. The guys pulled away, laughing, and left the room. "Nice job, Ali," Bo said. "You made a couple hundred bucks." "Thanks, Ali," Abby said with Bo's cock in her mouth. "You wanna give her what she wants, babe?" Bo asked Abby. "She earned it didn't she?" Abby stood up from her position and came over to the table. She squatted down on her heels and slid my panties to the side. She pulled out my bulging cock and started to suck. It felt incredible. Bo came over and stuck his massive dick in my mouth from the side. I began to work hard to get him off, thankful for all the money he had helped me raise for Abby, and for keeping me safe from all the other guys. If this is what being dominated felt like, and was like, I think I was in. Bo's meat was the best of all the guys I sucked that night. It tasted like a man and it felt like I was doing something kind by sucking him. I flashed my eyes at him. I licked his shaft. I sucked his balls. I deepthroated him. I did everything but look down at the beautiful woman sucking my dick. I realized this was all part of the plan too. They had now successfully confused my sex drive so that I was more focused on serving than receiving. More interested in cock than in pussy. That's why when Bo came, I came. One hand on Abby's head, the other on Bo's butt. My mouth on his cock, my dick in Abby's mouth. "Don't swallow," Bo said. Abby came up from my crotch and crawled over me on the table. There we were, two sluts in sexy clothes, and now we were swapping cum. We kissed for a while. She sucked up as much as she could and spit it into my mouth. I played the part. I swallowed it all. "Now," Abby said. "Any more second thoughts? Any guilt? Any shame?" I thought about it. "No," I said. "Good girl," Bo said. Abby kissed me. "That's going to make this a lot more fun," she said. ***** Next: Chapter 3: Tricked by a sorority and used as a fraternity's sex slave; Chapter 4: Cuckolded by my roommate when Emily visits; Chapter 5: Sexual favors to a teacher for a good grade; Chapter 6: Parents' weekend (the finale). A College Sissy Ch. 03 There was the time I was playing hide and seek at my friend's house. I was hiding. I ran upstairs, looking for some place to sneak into so I wouldn't be found. I felt my time slipping, but before it was too late, my friend's sister caught onto the game we were playing and waved me into her room. Her name was Stephanie. I was a shy kid, and my face turned red when I walked into Stephanie's room and saw a pink bra with rhinestones and lace strewn on the edge of her bed. She must have noticed because she giggled and said, "Do you want a really good hiding place?" She was stunning; a senior in high school. I was just at the age where maybe I knew what attracted me to her, but no, not really. I remember her waist tapering in, perfect and soft, behind a tight, low-cut, white cotton t-shirt. "Yeah," I said. Stephanie tossed me the girly bra I'd been ogling. I caught it and felt a stir in my belly like I'd only felt secretly looking through the Victoria's Secret catalog that came in the mail to my mother. "I won't look, but put it on," Stephanie said. She turned and reached into a drawer and pulled out a matching pair of panties. They were soft and shiny and cut like a bikini, I thought, with a triangle in the front that turned into a full-butted cover in the back, with two elastic pink satin bands connecting the two at the hips. Stephanie stretched the panties with her thumbs and tossed them over to me. "Then I'll look for a dress that'll fit. We look like we're the same size." I turned into the corner of her room and awkwardly pulled the panties up and fumbled with the bra. I couldn't clasp it behind my back. "How do you get this on?" I chuckled nervously, going with the whole game because I was, well, young and inhibited. And curious. "Put it on backwards around your belly, clasp them in front of you, then turn it around and pull the straps over your shoulders," Stephanie said with a laugh. "Ooh! I forgot about this." Stephanie pulled down a curly blond wig from the top of her closet and brushed it with her fingers. "I went as Marilyn Monroe on Halloween a couple years ago!" She placed the wig on the bed, and racked through clothes in her closet. She pulled a dress halfway out, looked at it, looked me up and down, all lanky and shy in bra and panties, and she said, "Perfect!" She pulled out a satin white dress, with a rhinestone buckle in the middle of the waist. It had two thick straps that went from the breasts over the shoulders and met at the collar on the back of the neck. The back was sheer white until it got to the butt, where it turned back to satin. The dress was long, with a slit going up the side of the left leg. "I wore this to prom two years ago," Stephanie said. "Everyone said it was so pretty, but it's not like I can wear it again." She waved me over to her and helped me slide into the dress. Feeling the satin against my skin was another bolt of lightning like I'd rarely experienced before. I didn't know clothes could be so evocative. "Oh, this is good," she said. "Now some makeup." Stephanie led me over to her dresser. As the dress stretched and rubbed against my panties, it created a friction and stir in me for what felt like the first time in my life. "You have such natural skin and a great bone structure, so we won't need much," Stephanie said. She put something colorful on my eyelids, some blush on my cheeks and some lipstick. Then she fixed the wig on my head and started to style it with pins and a flower hair clip she had on the dresser. Stephanie leaned back and looked at me. "Stunning," she said. "He's never going to know where to find you," Stephanie said, and I remembered I was in a game of hide and seek. "I'll open the door and we'll paint our nails and he'll think you're one of my friends. You look like my friend, Natalie, anyway!" I couldn't stand the thought of my friend catching me dressed like a girl. He was the kind of kid that'd go and tell everyone in school that I was a faggot and I'd never have a chance with making any friends, or girlfriends, ever again. But the truth was I liked looking like a girl, at least looking like this girl. And I liked that a girl as pretty and popular as Stephanie was in control. Stephanie closed the blinds and turned on a few soft lamps. She pulled up a bag of nail polish and told me to pick a color. I picked a light, sparkly green and Stephanie giggled. She got up from the bed and said, "Ready?" and opened the door. My heart began to beat harder, but I didn't really look like me anymore so maybe my friend wouldn't notice. Stephanie grabbed my left foot and started to paint the big toe. "So, do you have a crush on anyone?" she asked. "Um, no," I said. "Alex," she said, whispering, "Play the part." "Oh," I said, turning my voice into a girl's. "Well, yeah there is this one boy." "Who is it?" Stephanie said. I wasn't sure if she was giggling to keep up the role-playing or if she was giggling at how quickly I'd turned into a girl. "Just this guy on the football team," I said. "Giggle," Stephanie whispered. "My brother's coming." I giggled in the girliest way I could pretend and flipped my hair back over my shoulder. "Steph, have you seen Alex?" my friend asked coming into the room. He stopped in the doorway and looked at me. He smiled. I'd been caught. "Brandon, have you met my friend... Natalie?" "No," he said. "Do you go to our school?" "No, she doesn't," Stephanie said, speaking for me. She must not have trusted my voice. "Ew, Brandon, stop looking at her like that." I realized my friend had been staring at me the way I'd been staring at Stephanie earlier. I blushed. "It's fine," I said to Stephanie, leaning forward to touch her arm lightly. Brandon turned red. "OK, bro, get out of here," Stephanie said. "Go play your stupid little game. Aren't you too old for this shit anyway?" Brandon brushed her off and turned to leave. "Bye, uh, Natalie," he said as he left. "Ew, Brandon, go!" Stephanie finished painting the nails on my foot. "You know, you shouldn't break guys' hearts like that. It'll come back to bite you one day." ** I woke up. I was back in bed, in college, with a lavender slip on. Bo was gone from the other bed. My mind started to come awake. Was it a dream? Was I going down this road again? And what of the dream I'd had the night before — did that really happen, did Stephanie really feminize me when I was younger? Did she really take a photo of me and promise to show only her friends? Did she really then take that photo and pass it to everyone on the football team; on my football team? Did the football coach then really pull me into his office and ask if I was a 'tranny'? Did the upperclassmen post the photo on my locker and put pairs of panties in my backpack? Did I really have to leave transfer schools and promise to never think about this again? To block it out of my memory? To commit myself to being a regular guy who likes regular girls? To so thoroughly suppress the urge to go shopping for women's clothes or try on my sister's panties or pretend to be a girl online that I killed that part of me, and killed a part of what makes me human and happy? Did I really kill my true identity? Or was it all a made-up dream? Did Abby slip into my room after the fuckfest the other night and whisper stories about how I've always been a girl into my ear? Did my brain turn those stories into memories so that I dream of them as if I've been denying my true calling in life: to be a woman who so deeply craves validation that she'll do anything other women say and perform any act on any man that comes by? What confusion. I was thirsty so I reached for my water cup. There was a note on my bedside table. I opened it. It read: Hi cutie! You were wonderful at the fuckfest the other night. You showed your master and I that you're ready to be serious about becoming a woman, and acting like one. And even better, you showed me that you're a good girlfriend. So good in fact that I'd like you to come to our sorority rush party today. I think the girls will love you, and you'll finally have that sisterhood that I know you're craving. Meet me at KKG house at 3. I hope you've been practicing your makeup, your hair and your walk. Wear the clothes I laid out for you in your closet. Look hot. It's going to be a big night. Lova ya, baaatch. I put the note down back on the table and smiled. Whatever transformation was happening — and whether it started years ago or really just this semester — was turning out to be a good one regardless. There were growing pains for sure, but that's because I had to overcome a lot of obstacles in my subconscious, it seemed. It required aggressive femininity to become a girl, and now that was on the other side, I was glad I had made the effort. I got out of bed and put on the pink bathrobe Abby had given me. I didn't mind walking down the hall of the dorm to the bathroom anymore; girls scoffed and guys looked, but I had adopted this attitude that whatever I am, I am desirable. I'd gotten dozens of guys off, and I was starting to look like an actual normal college girl. That's what I told myself at least. I hopped in the shower and shaved my legs and the little bits of my chest. I had gotten really thin after switching diets to look more feminine, but by butt was still a bubble that I'd learned to sway back and forth when I walked. I finished my shower and plucked my eyebrows in the bathroom. A nice boy from the down the hall, Rob, walked by and whistled playfully. He was one of the guys whom I'd sucked off in the basement the other night, and he patted me on the ass as he walked by and said, "Stop by anytime, Ali." He was clearly one of the guys who reacted well to the gangbang; some boys who were insecure in their masculinity and sexuality looked like they wanted to beat the shit out of me. I kind of liked the feeling of subverting their sexuality and fucking with their minds. I went to leave, but instead paused and turned toward Rob's shower stall. I thought I'd thank him for his kindness. I put my robe on another hanger so it wouldn't look like we were in the stall together. I slid open the curtain and snuck in behind him. I reached my arm around him as he was washing his hair and grabbed his cock. "What the-" he said. "Not here, man." "Shh," I said. "And just pretend I'm a girl, 'k? Like the other night?" I remembered the aweomse feeling of being a woman in control of a man. I dropped to my knees and took his cock in my mouth. He was hard already; I knew he liked me. Water came pouring down from his body down onto my face, making it hard to breathe with his cock in my mouth, so I pumped my head back and forth as fast as I could, rubbing my tongue underneath his cock. He put his hand on the back of my head, and it occurred to me that this was the first time I was naked and having sex with a guy. I had internalized my femininity so much that I didn't need clothes or makeup to justify my girly actions. Rob took the back of my head in both hands and pulled me down on his cock so my nose touched his stomach. He shot a massive load deep into my throat and I moaned in delight, swallowing as fast as I could. The warm jizz slid down my throat as I kissed the top of his cock, got up from my knees and left like it was nothing. I grabbed my bathrobe and went back to my room. I opened the closet to see what Abby had laid out for me. I was shocked. Arranged neatly on the top of the dresser was the pink rhinestone and lace bra and panty set that I'd dreamed about the night before. The panties were satin and stretchy, and so sexy. The bra was so feminine, and felt so much like an expression of my style and identity. And then I saw the shoes: patent leather heels in the same shade of green Stephanie had painted on my toes in my dream, or when I was younger, or... I don't know when but they were the same. I slid on the satin panties and tucked my cock into them. I loved the feel of the full satin bikini on my ass, and I couldn't keep my hands off myself. I slipped the bra on, and this time had no issue with the clasp; a subtle womanly quality I'd acquired over the course of the last few weeks. Then I pulled out the dress Abby had picked out for me: a white, tight satin cocktail dress with two thick straps that met behind the neck. The back was full and sheer, and tapered down to just above the butt, where it returned to tight satin. Unlike the dress in my dream, it tapered off as a cocktail dress, like it had been altered from a prom dress to an adult woman's evening dress; like I'd graduated from playing games of dress-up to realizing that I may have always been better off as a woman. I slipped the dress on, and it hugged all my curves. It came down mid-thigh, and my tan, smooth legs looked incredible in them. I put the heels on and squealed in delight. I had to tuck my cock back into my satin panties, becoming ever more a hindrance, to keep from showing my excitement. I did my makeup for the event as a symbol of how I felt on the inside: playful, bold, exotic and utterly feminine: Big sparkly eye shadow that faded from silver to green from the inside of my eyes out; big thick lashes; a bright, cherry red lipstick that shined with gloss. I went heavy on contour, bumping up my cheekbones to highlight my eyes and make my face more feminine. I was getting startlingly good at this. I grabbed the long brown designer wig I'd bought and styled it like a pinup model got a makeover from someone on Jersey Shore. I puffed up the front of my bangs, clipping it on the top of my head, and straightened the sides, letting some strands fall before my shoulder, but the rest in the back. I put on a string of pearls, because that's what Southern ladies do, I was told. I put on some pearl studs, too, and sat at my desk to paint my nails the sparkly shade of green from my dreams. ** I was a little fashionably late to the sorority house. I knocked on the door and two young girls dressed in classy white peplum dresses invited me in. They giggled, but were very nice to me, and one said, "Come on in, Ali, it's so nice to meet you." The two girls looked so perfect and pretty that it made me feel a little silly to be so done up and to have convinced myself that I was turning into a girl. They had hips and small waists and perfect little breasts; their hair was natural and long and stunning. They walked with grace I hadn't yet learned. But as soon as I got down on myself, I was led into the banquet room of the sorority house and a group of 50 stunning young women were waiting to welcome me. They went into some kitschy chant about sisterhood, and Abby came from seemingly out of nowhere, and led me into the middle of the circle. All the girls were wearing the pretty white peplum dresses, with perfect makeup and perfect hair. They were smiling and clapping and cheering me, and I felt loved. I felt like a sister. "Pledges, you are excused," Abby said. About 15 of the girls left the room, and the last one shut the door. "Now," a blonde girl said. She was a Stepford wife type. "Abby here has told us all about you. And part of what we do as a sisterhood is welcome in girls who need some help becoming more feminine." "But it's not a free proposition," Abby said, cutting in. "In order to be a Kappa, you need to prove to all the sisters here that you're committed to femininity, and committed to doing whatever it takes to become a sister. Does that sound like something you want to do?" "Absolutely," I said in my new feminine voice. I heard some girls on the side giggle, but the blonde girl, the sorority president, Meredith, shot them eyes and they shut up. "Perfect," Meredith said. "Well, you've done most of the hard work for us. You and Abby, at least." "She looks great, doesn't she?" Abby said. The group of girls gleefully said yes in chorus. "Thank you, girls," I said. "Oh you're welcome, Ali," Meredith said, pacing back and forth in front of me. I watched as she gracefully walked in heels, a perfect model of womanhood. "Now, are you ready for your one and only challenge to become a Kappa?" "Yes," I said, sitting up and arching my back. My legs crossed at the ankles like I'd been taught. "Great, then come with Abby and I," Meredith said. "Say goodbye, girls." The group of sorority sisters said goodbye in unison. The small group of pledges opened the door of the banquet room, and the two girls who let me in waved me to the front. Abby and Meredith followed behind me. When I got to the front, my vision went black. "Now, we're going to blindfold you for just a little bit," Meredith said. "We do this for every girl who does this." "OK," I said, nervous. It was hard enough to walk in heels with full vision. We walked for about five minutes until I heard the deep bass of men's voices. I was led up some steps and into a building. I walked along a wood floor clacking my high heels, with the two pledges guiding my arms and Abby and Meredith talking quietly behind me, saying hello to guys as we walked down the hall. I could feel the atmosphere change; there was a lot of testosterone in this new building. Finally we stopped walking, and the girls let go of my arms. "On your knees," Abby said. I obliged. I heard the laughter of a pretty large group of guys. The blindfold was removed. I looked around and I was in the middle of a circle of about a hundred guys. On the inside were about 20 naked boys around my age. They formed an immediate circle around me, Abby and Meredith. On the outside, the rest of the guys sat on chairs, stood in corners or rested on furniture with beers in hand, talking to each other and cracking jokes. "Say hello to our new pledge, boys," Meredith said laughing. She had this disengaged quality about her that was unlike what Abby had shown me in this period. I was a tool for her, it seemed like, and I was beginning to learn that she hated everything about me. The guys started laughing at Meredith's request, giddy with the prospect of humiliating me, and so I hated her, too, for that. Some of the guys made sarcastic catcall sounds, some were less tactful and said, "Look at that bitch," or worse, "Look at that faggot." A good-looking guy in a blazer with broad shoulders and combed hair came out of the shadows and approached Meredith. "Hi Mr. President," she said sweetly. How quickly she switched from dom to sub in the presence of a strong man; Abby had done that with Bo, too. They whispered things in each other's ears, seemingly finalizing plans. "Gentlemen of Delta Chi," the president said. "This is the culmination of our fall rush. Our 21 pledges stand before you, all with the hopes of becoming a brother of our organization. They have done everything we have asked of them. Not all who started have made it until today, but the ones who do stand here have earned the right to do so. This final contest will serve as the final challenge of rush." The crowd of guys burst into cheers. "Now, upperclassmen, you know what is about to happen," the guy said. "Before us we have a sacrifice from the Kappas. This... thing... is a sissy little bitch that the lovely Abby here has made as feminine as possible." The crowd cheered again. For Abby, I'm guessing, because she raised her arm in the air and waved. "We've set up a challenge to see how dedicated these pledges are to the fraternity. This tranny whore will do everything he... or, uh, she... can to turn on our pledges. The first pledge to get a boner will be kicked out of the fraternity," the president said. "That is, unless they have sex with the tranny right here, in front of all of us." The crowd whooped into a holler. The 21 pledges looked at each other, and then at me, and then back at each other. I felt so humiliated, and not at all like a woman. I felt like what the guy'd called me: a sissy tranny faggot. A College Sissy Ch. 03 "Now because this tranny is so ugly she'd never get anyone hard, we'll kick this off with a bang," the guy said. "Ladies?" The crowd started to cheer. Abby turned to Meredith and they embraced. They began to make out hard. Abby reached down to Meredith's ass and squeezed. Meredith, this incredible, composed and perfect blonde woman, kissed Abby's neck and reached into the front of her panties to finger her. The crowd went wild. I looked around at the pledges, none had sprung erections, but a few were looking up at the ceiling, pained. "Alright," the frat president said. "You passed the first test. This should be easy, pledges, unless you really do like trannies. Abby, any final words to your... pledge?" He paused on the word pledge like it was absurd I could ever be a sorority girl, or a girl at all. "Ali," Abby said, whispering, as the crowd started to grow rowdy, throwing beer cups into the middle of the circle. "If you can get one these guys hard, you're in. We all had to do it in Kappa, OK?" "OK," I said. "You look great, hon," Abby said. I appreciated her sweetness. For every trick she pulled, she came back with something sweet. It was a crazy game she played with me. I did, however, feel renewed determination to make at least one of these guys hard after her pep talk. I stood up and started to dance as sexily as I could. It was embarrassing. All the guys on the outside started to laugh, and Meredith doubled over in laughter, leaning into Abby. Even she was laughing, too. I slowly pulled up my tight dress over my ass to reveal my pink satin panties. More catcalls came from the crowd. I didn't see a hard cock in sight, but I saw several guys looking away from me. Actually more guys were looking away from me than when Abby and Meredith made out. I looked around the circle, tousling my hair, and dancing to the music that a guy had started to play on the speakers — Dude Looks Like a Lady. Of course. But I felt like a stripper, and I knew overcoming humiliation was part of the transformation process, and part of what the sorority was looking for. I finally caught eyes with a guy who looked really scared. He had long-ish, wavy brown hair. His muscles were slightly defined. He was tall and tan, with dark brown eyes. He had his hands behind his back. "Uh oh," came a chorus of guys as I started to walk over to him. "What's your name?" I whispered in his ear, turning my back to him and sliding down his front. "Go away," he said. "Please." I felt bad, but I wanted to show how quickly I could win this challenge. "Shh," I said, putting my finger on his lips and smiling. The crowd loved it and laughed. "Just fuck me like you want to and this'll be over." He sighed and looked me up and down as I danced up on him. I rubbed my satin pantied ass over his cock, back and forth. I turned to face him and placed his hand under my dress and onto the bulge in my panties. He shuddered and let out the littlest smile. I immediately leaned in and kissed him on the lips. He opened his mouth slightly, forgetting where he was, and for a second, he slipped his tongue into my mouth. He pushed me away and said, "Fuck," loudly and angrily. When I looked down, his cock was rock hard. "Wow, that was quick!" the president said. "You must love fucking sissies you goddamn queer. Alright, Mark, you know what you gotta do if you want to be in. Everyone else, you're brothers. And brothers stick together. So if you also want to be in the fraternity, you're going to have to cum, too. So start jacking off, and when these two sissies are done, you're going to cum on them." The president barely got out the orders before laughing uncontrollably and falling into his laughing buddies. Mark looked at me softly. I could feel for him. We were in this together, and he and I were in remarkably similar positions. He clearly had a thing for me, and probably had a thing for guys, transgender people or something in between. Meanwhile, I was just trying to validate my own femininity through sexual actions; the only way I knew how. We were both trying to gain access to clubs that are based on gender — a fraternity and sorority — yet here we were, clearly blurring gender and romantic lines. I think I fell a little bit in love with him. Or, the idea of him at least. "C'mon, Mark," the president said. "Fuck that tranny." "Do it," I said, smiling a bit. "Let's just get it over with." I dropped to my knees and starting blowing Mark as best as I could. Even with all the guys jacking off and looking at us, I blew him not to prove anything to anyone but him. I wanted him to feel so good that he would think this was natural and that he'd be OK with maybe loving me back. I grabbed his ass and thrust his cock deeper into my mouth. "Gag that fag!" someone yelled from the crowd. I looked up at Mark's eyes with his massive cock in my mouth and nodded. He grabbed my head and thrust me down until I gagged several times and slobbered all over my chin. I had glittery tears running down my cheeks. Then the crowd started to chant "Kiss!" I pulled Mark out of my mouth and stood up, wiping away my strewn makeup. We were the same height with me in my heels. He put his arms around me and pulled me in. We met lips and enjoyed a deep kiss. Our tongues wrestled for a minute or more, occasionally bobbing back into our own mouth so we could touch lips tenderly. Mark put his hands on my butt and lifted up my dress to feel my panties. He poked his finger into my asshole from the outside of my panties. "Now fuck!" came more calls. "It's all yours, Mark," I whispered in his ear. I got on all fours, in this banquet room filled with fraternity brothers cackling and calling me 'tranny' and 'faggot' with this guy I'd never met but whom I think I had a connection with and who was about to plow my ass in front of the crowd. I got on my knees and he got on his, and spit down on his cock. He forced it into my hole and the crowd cheered as he leaned back and sighed in subdued delight. It hurt my tight, dry hole, but I loved the attention and I wanted to be as close to a girl for Mark as I could. He pumped hard, trying to get off as quickly as possible so we could be done with the show, and I pumped back, bouncing my fat ass for him, occasionally spinning my hair and looking back at him in my sexiest feminine gaze. I was going to be his girl tonight. That was the plan until someone yelled, "Cum in each other's mouths!" which elicited a huge response from the crowd. Mark pulled out and I got on my knees to face him. "I'm sorry," I said, pushing his back onto the ground. I straddled him and took my dress off finally, and the crowd went wild, half mocking but also half eager to see the grand finale. I pulled my panties aside and pulled the hair over my head and lowered myself onto Mark. He took my cock into his mouth and the warmth of it nearly had me explode immediately. I took his cock into mine and we 69'ed in front of the crowd hollering, "Cum!" I bobbed my head aggressively up and down on his cock to put on a show. Mark sucked my dick like it was his first time, and it probably was. Though, he was eager. I soon pulled off his cock and sat back on his face to ask him, "Ready?" The crowd loved that I was sitting on his face. He answered back, "Yes," muffled. I got back down on his cock and felt my cum go. Just as I did, I took the biggest load in my mouth that I'd ever taken. "Don't swallow," someone said. And so I sucked Mark dry and then got up, knowing what to do. I turned around and laid on top of him, in my pink bra and panties and high heels, with my slutty makeup and hair, and swapped cum with him. It was messy, but Mark seemed relieved and aggressively tongued me back. "Ok, ok, faggots," the president said. "Boys, get to it." The group of young guys circled in, tugging on their throbbing red cocks. I was in such bliss with Mark, having felt such a connection, that I had forgotten about the rest of the job. One by one the pledges stepped forward to shoot their loads over Mark and I as we passionately made out throughout the entire process. Mark had to pretend to get out of the way of the cumshots, to save face with his brothers, so when jizz did land on his face, I'd pull my tongue out of his mouth to lap it up. Before I swallowed, I'd kiss him deeply. That was just for us. He grew resigned with the fact that he liked it; his brothers be damned. Occasionally I'd peel off to catch a cumshot on my face if I saw a guy was ready. Some aggressive guys would push my head away and say, "Stop it, faggot," which hurt, but I guess I was getting the last laugh, huh? The final guys finished up, and by the end of it, Mark and I had swallowed about 23 loads. Exhausted, I pulled off Mark and got my dress. I slid it back on as the crowd dissipated, humiliated by what they'd seen, while some guys clearly tried to compensate for their confused feelings of arousal during the process. I walked over to Abby and Meredith at the door. "So, did I get in?" I asked. Meredith laughed. "You're a fucking tranny whore. We're a sorority of women, and you'll never be one. So no, you're not in, faggot," Meredith said. I looked at Abby. "Sorry, Ali, it was my turn to get a sacrifice for the boys," she said. "But don't act like you didn't love it." "Yeah," Meredith said. "You're not a sorority sister, or a woman, but you clearly loved every second of that. And I think we're going to use you again in the future. Is that OK, Abby?" "That's why we have her," Abby said. "Now go back to the dorm. I'll meet you there later tonight." I felt used. Mostly because I was. But I was shocked that my brain had developed an attraction to a man. To Mark. That relationship, me as a girlfriend, felt new and exciting. Whatever Abby did to me and however she abused me was immaterial, because I had gotten to this new point. I had something new to latch onto—being a girlfriend, or fantasizing about being one. I had no idea if Mark felt the same. I got back to the dorm and laid down on the bed in my dress, bra and panties. The same outfit I wore in my dream when I was younger. My past and present, my dreams and my reality, were colliding. I saw I had two texts. The first was from Mark: "Hi Ali. It's Mark from the thing. I got your number from Abby. I'm sorry for what happened in there. I rejected the pledge bid from the fraternity. Do you want to meet sometime tomorrow?" The second was from my girlfriend back home, Emily. My distant girlfriend who still loved me and knew nothing of my new life as Ali: "Ready for me to visit you at college next weekend?" My past and present colliding. --- Chapter 4: Cuckolded by my roommate when Emily visits; Chapter 5: Sexual favors to a teacher for a good grade; Chapter 6: Parents' weekend (the finale).