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  • A College Sissy Ch. 01

A College Sissy Ch. 01

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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."

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