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.”
“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.
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.
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.
Sissy Cuck Boy 