Dirty Angel

"Are you really gonna go through with this?" I asked skeptically.

"Yes, I am," said Scott, in his end-of-discussion voice.

"And what if you're recognized by someone you know?" I said.

"Then I'll simply tell them that I'm doing this to get into the fraternity," said Scott patiently, as if I had been a stupid kid.

He put his high-heeled shoes on, pinched at the hem of the skirt, and fluffed up his wig a bit. He looked just like a girl, which was the assignment for tonight - well, that and waiting on the frat brothers at the keg party.

"You just be careful the frat won't try to get into YOU," I warned him. "You look like a slut."

Scott playfully flipped me the finger and left. I turned my attention back to my English Literature.

"Jane Austen..."

How could he humiliate himself like that? Dress up in drag and put on a wig and make-up! Hell, no frat, no matter how cool, was worth that!

"Jane Austen, author of..."

He made a convincing woman, though. He had a rather feminine face, with big blue eyes and a pouty mouth, and those slim legs... Focus!

"Jane Austen, author of `Sense and Sensibility´, `Pride and Prejudice´, `Emma´..."

He walked remarkably easy in those high-heeled shoes. Perhaps he was used to them..? I put my books aside. There was no use. I couldn't concentrate on homework tonight. I turned on the TV and watched some boring movie about war in a tropical country. I fell asleep midway through it.

* * * * *

I woke up at 4 am by a loud "thump!" at the door. Scott was back. He didn't come in though, and after a few minutes I got up and opened the door. What a mess! Scott was lying on the carpet in the hallway just outside our door, but if he had fallen there or if some of the frat brothers had simply dumped him there, I couldn't tell. Scott's clothes were twisted and wrinkled, his wig hung crooked, and the make-up was smeared out all over his face.

"Scott? Are you OK, man?"

I shook him gently by the shoulder, but he just mumbled something and nodded off. He was pissed drunk.

"Fuck this frat shit..!" I muttered, and dragged him into our room.

I managed to heave him up on his bed. He looked really awful. His black pantyhose had several runs on both legs. The short dress had risen up to a microskirt length, and he had lost one of his shoes. The mascara had floated out all around his eyes, as if he had been rubbing them - which he probably had. His lipstick was smeared out all around his mouth - I didn't want to know how THAT had happened. He looked sleazy. Cheap. Slutty.

I took his remaining shoe off and dropped it next to the bed. I better get that outfit off him, or he'd be uncomfortable - that is, if he noticed anything at all. He seemed pretty wasted. I tried to take the wig off, but it was more difficult than I thought. e had used a lot of hair pins to make sure it stayed on. I sat down by the side of the bed and searched through the wig for every damned pin, and tossed them on the floor, muttering some very dirty words. Scott mumbled something and put his hand on my arm.

"Are you awake, man?" I said.

No answer. I put the wig on his nightstand. He looked weird without it. With the wig on, he looked like a slutty girl. Without it... without it he looked like a guy in drag with a messed-up make-up! He was still cute, though. Even cuter than normal, actually. He looked slutty and sexy and totally defenseless. I bet he wouldn't even remember me undressing him. The sudden realization of the power I had over him right now made me giggle. I could do whatever I wanted to him, and he wouldn't remember it! Hell, if I tattooed "I LUV MY MUMMY" on the guy's back, he'd just assume it happened at the keg party!

I couldn't do anything nasty to him, though. Scott was such a sweet kid. I liked him. A lot. I moved my finger over his red lips. His front teeth pointed just a tad forward, resting against his pouty lower lip. I pushed it gently, and was surprised when he put his lips around my finger and sucked on it! My heart pounded, and I felt warm and heavy. That little red mouth looked so hot sucking on my finger. So sexy... All of a sudden, I wanted to see those hot lips wrapped around another body part of mine. Could I..? What if he woke up?

Oh, what was I thinking? He WAS awake, he was just so drunk that he had no clue what he was doing! Carefully, I pulled my dick out and jerked it off a little to make it really hard. I straddled Scott's chest, held his head up, and pushed my dick against his lips. He opened his mouth like a good boy, and I stuck my dick inside it.

Fuck, I was in heaven!

His mouth was wet and warm and soft, and I had to hold back not to come immediately. I wanted this wonderful feeling to last. Scott didn't react when I slowly fucked his mouth. The only way I could tell that he wasn't unconscious was an occasional grunt. I had to pull out to stop myself from shooting down his throat. I was afraid he might choke to death on my cum.

Instead, I moved down and let my hands roam over his body. His fake boobs weren't interesting, I knew they were just socks. But his slim, sexy legs... I caressed them, smiling at the fact that Scott had even taken the time to shave them before going out. His calves were slim and firm and smooth under my touch. I moved my hands higher, up his thighs, scraped his skin with my nails as I travelled towards Pleasureville. He shifted slightly. When I reached the hem of the skirt, I could clearly see the growing bulge under it. I lifted the skirt up, and pulled the pantyhose and briefs off one of his legs. I needed free access to his crotch, but at the same time I kind of liked seeing him in black pantyhose - it made this game even hotter. His dick was already hard and dripping with pre cum. I took it in my hand and jerked him off carefully. He moaned. His eyelashes fluttered. He couldn't keep still.

God, he was sexy! I had to have him, had to get inside his hot little ass and pump all I had into him, the sexy little slut! But I couldn't very well rape him. He had to enjoy it. I had to prepare him.

I parted his legs to get better access to that sweet ass. I let my tongue slide from the head of his dick, down the shaft, down to his balls. I took a little time to suck on them, and he writhed and breathed heavier. I still moved my one hand up and down his shaft, and wet one of my fingers on my other hand before I pushed it against that little pink star. He was tight as hell, and my finger only made it to the second knuckle. He groaned again, but this time out of discomfort. I pulled my finger out, dripped some saliva in his hole, and pressed my finger back in. It slid in a little easier now, but he was still tight, and I wondered how in the world I was going to fit my dick into this tiny hole. Scot grunted, partly from discomfort, but also from pleasure, and I smiled. If I'd just do this a little while longer, he'd relax and start to feel good. I forced my finger all the way in to the third knuckle, pulled it out, and pressed it back in.

As I fingerfucked his ass, Scott's breathing got more ragged, and his dick dripped more pre cum onto my hand. I used some more saliva for lubricant before I pushed two fingers into him. He winced a little, but soon he was back at moaning and shivering and bucking his ass back against my hand. I decided to go for it, and put lots of saliva over my hard dick to slick it up some more. Scott whimpered when I pushed the head of my dick passed his sphincter. I jerked him off some more to keep him horny, got into the position I wanted, and then, with one mighty thrust, I buried myself all the way inside his ass. I silenced his cry with my mouth. He opened his eyes and stared at me, and for a moment I thought he had sobered up and was going to get mad at me. I jerked his dick off as fast as I could. He moaned, closed his eyes, and put his arms around me.

That was all the approval I needed. I thrust into him again and again, jerked him off, and kissed him harder than I've ever kissed any girl. He kissed me back, held up his legs to let me penetrate him even deeper, and when he came, he bit my shoulder to keep quiet. His cum shot all over my hand. I wiped it off on his dress. He sighed loudly and relaxed. I pulled back a little, grabbed his dress, and used it to pull him closer to me. I lifted his pantyhose-clad leg up over my shoulder. He raised his arms over his head and gave me a sleepy smile.

My dirty little angel! I thrust harder into him, determined not to let him fall asleep before I was done with him.

He closed his eyes and licked his lips. Those sweet, dirty lips that had been wrapped around my dick just a few minutes ago. He didn't groan out of pain anymore, no matter how hard I shoved my dick up his ass. Instead, he moaned with delight, and even looked up once to fucking WINK at me, the little slut! The sexy sight made my balls explode, and I sent jets of hot cum inside his ass. I buried my head against his shoulder to stifle my scream.

I lied still for a moment, catching my breath, then I pulled out of him. I was about to get out of there when he put his arms around me and whispered:

"Don't go, Rick. Sleep with me... please?"

So I curled up next to him, sank into his warm embrace, and lied there, listening to his breath, as we drifted off to sleep.