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.