My Roommate, Brian

byOptimusCrime©

I stood in the middle of my room, frozen in shock and total disarray. On the other side of the doorway stood my roommate Brian, staring at me in disbelief. It wasn't a very confusing situation, and not many excuses I could come up with. I had my boxers around my ankles, and my lotion covered hand wrapped around my dick. Well, not much of my dick was showing. It wasn't exactly a decently sized one, topping out at just under 4 inches. On my computer was a porno starring a very obvious transvestite getting penetrated by a man. I was beet red, naturally, and was almost ready to cry when he suddenly burst out laughing. Not just a few giggles either; he was doubled over laughing till tears came to his eyes. Finally he sobered up enough to collect himself again, and apologized for entering without knocking. Still chuckling to himself, Brian left the room, while I tried not to cry.

It was an hour before I dared leave my room again. I went into the kitchen to find Brian eating a bowl of cereal. I couldn't look him in the eyes, but I could swear he was smirking at me. We didn't talk much over the next few days, which were the most embarrassing of my life. Everywhere I went, I felt eyes on me. Finally, Brian walked up to me while I was in the kitchen, making myself a sandwich.

"I'm going to the bar with some of the guys," he said calmly, with no indication that there was any awkwardness between us. "I'm asking if you wanted to come, but I guess you probably don't."

"Oh," I said nervously, the shakiness of my voice betraying my continuing embarrassment. "Yes, I think I'd rather stay home today."

"Okay, your call," he replied with a smile. "I figure I better be leaving now. Think you could grab me my jacket? It's on the couch."

"Sure thing," I said, secretly relieved that he would be leaving for a while. Perhaps this whole thing had blown over. I certainly wanted to put it out of my mind forever. I grabbed his jacket off the couch and went over to the door, where he was putting on his shoes.

"Thanks," he said as I handed it to him. "Oh, and I almost forgot. I got this huge pile of dirty clothes in my room that I never got around to, could you be an awesome guy and do that for me? I'll make it up to you, I swear."

I agreed. Laundry wasn't a very tedious chore, and I had my own to do anyway. However, he had one more thing to say.

"And also, I'd like you to use this," he said, handing me a big cardboard box. It was a shipping delivery, and had gotten in recently, probably while I was in class. I opened it to look inside, and my jaw dropped. It was a maid outfit. Not a real one, but one of those lingerie style fetish outfits. I looked up at Brian in shock, and he smiled down at me.

"Just try, it'll be fun," he said. "I'm dead serious. Just try."

I hesitated, wondering whether he was just making fun of me or not. I saw nothing but honesty in his eyes, however, which made me trust him. I told him I would try, and he said he was glad.

With that, Brian opened the door and left, leaving me standing dumbfounded with the box in my arms.

It was a while before I could collect my thoughts enough to actually make any kind of decision about this. I went to my room, and laid out the contents of the box on my bed. There was a short black dress, with a white apron attached, a black thong, matching black bra, and fishnet stockings with lace at the top. Underneath these was a pair of high heeled shoes, a blonde wig, and a makeup box. I couldn't believe Brian expected me to wear any of this! I was very turned on by crossdressing however, and something told me this was a chance to see how I liked it. It was probably just a prank by him, so he could get some embarrassing photos of me, but I could always get a new roommate if I had to.

I took a shower, and shaved my legs for the first time in my life. It was a very slow process, and I scratched myself more than once. To be honest, hairless legs felt pretty good once I was done. Next I shaved my crotch and my arms. To my own embarrassment, I was fully erect when I slipped on the tight black thong, and I liked the way the strap felt against my butt. I tucked my little cock to the side without much difficulty, and immediately felt very feminine. The bra was also in my size, and I slipped the dress over it. The silk felt good against my smooth skin, and I was more than a little turned on. I pulled the stockings up on my legs and fastened them to the panties easily, even though I'd never done this before. I finally placed the short blonde wig on my head, and went into the bathroom to do my makeup.

The moment I caught sight of the mirror, I stopped in my tracks. I saw a sexy little maid looking back at me, instead of the not-so-sexy man that was usually there instead. I felt so beautiful, and wiggled my hips in glee. With renewed zeal, I put on the makeup. I'd never done it before, so it came out a bit thick, but I kind of liked it. It looked edgy and slutty, which turned me on much more. I felt a little bit of wetness in my panties. I walked over to Brian's room to pick up the laundry, tottering a little in my new heels. I carried it over to the washing machine, and began my maid duties. As I washed and folded his clothes, I noticed for the first time how much bigger than mine they were. Brian was 6 foot 2 and beefy, much larger than my skinny 5 foot 6 frame. The more I thought about him, the more my heartbeat sped up.

Just as I was finishing folding the freshly washed clothes, I heard a key in the door, and my heart skipped a beat. Brian was back. How would he react to me in my outfit? I walked out of the laundry room to greet him just as he walked in the door. His reaction was immediate.

Brian stopped, mouth agape, starting at me from head to toe. He looked for a while before walking up to me and running his hand down my blonde hair, cropped slightly below my ears.

"I had no idea you'd look so hot," he breathed in disbelief. I didn't say anything, trying to make sense of why I was so incredibly turned on. Brian slowly stroked my slim body down to my hips. His right hand snaked around my waist, and pulled me in close to him. I stared up at him with wide eyes, feeling perfectly submissive to the big man in front of me. Hand still on my waist, he leaned down and kissed me full on the lips.

I felt like I had been electrified. The tingle running down my spine was the most intense I had ever felt, and I sighed deeply and melted into his arms, letting his tongue invade my mouth. As we passionately kissed, I felt his hands sneak down to my butt, rubbing it all over. Instinctively, I moved my hands down over his cock, rubbing it gently through his jeans. He was hard as a rock.

Brian finally broke off the kiss and smiled down at me. I continued slowly rubbing his cock, enjoying feeling the hardness, knowing he wanted me. Brian moved his hand back up to my shoulder, this time pushing down. I knew what was expected of me, and suddenly found myself wanting nothing more than his dick filling up my girly mouth. I knelt down in front of him, tucking my dress down under my bottom.

I undid his belt, and his pants dropped down. I could see his bulge already. I pulled down his underpants and his cock jumped out at me. My eyes widened as I saw its size. It was about nine inches long, and much thicker than mine, which was at this point harder than it had ever been in my life. In awe, I slowly wrapped my hand around Brian's shaft. He closed his eyes and sighed deeply as I brushed my hair out of my face and brought my freshly lipsticked red lips to the tip of his cock, kissing it slowly. I ran my tongue down the underside of it, down to his balls, and I loved the way his breathing quickened. I had never felt as wonderful in my life as I did on my knees, in my slutty little maid outfit, sucking his cock. I was getting into it now, sliding my mouth up and down his length, swirling my tongue over the head.

Brian was exhaling deeply, almost sighing with pleasure with each movement of my tongue. I tentatively deep throated him, going a little deeper each time. I got a little too excited though, and tried to go too far, starting to gag. Brian pulled his dick out of my mouth, and asked me if I was okay. I so desperately wanted to please him; I nodded my head yes. I kissed his balls, and was rewarded with a grunt of satisfaction. I went back to sucking his cock, feeling its girth slide in and out of my mouth, as I moaned with every thrust of Brian's hips. His grunts got closer and closer together, and I knew he was close to orgasm! I quickened the pace of the head I was giving him, using my tongue on his head, trying to get him to cum in my mouth. And cum he did!

I had no idea anyone could cum so much. With a loud moan, Brian exploded right in my mouth, and I squealed in shock. I struggled to swallow all of his hot, salty cum without spilling any. I licked his cock clean, and gave his balls a last tender kiss before sitting back on my heels, kneeling on the floor. Brian pulled his pants back up. He stepped back and grinned down at me, and I could only smile back. I didn't know where this would go, but I knew one thing for sure. I wanted nothing more than the chance to be this man's girl for the rest of my life.

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by Anonymous

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by hollandguy06/17/14

nice

Great story loved it. More pkease

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by TurningintoCD01/24/14

Love this story!

Great job! Stories of crossdressing for a guy, which end sweetly, are so rare. Keep it up!

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