Matt Jessica and Me

Having just recently gotten off the plane from my return trip to California, I am reminded of the first time Matt and I had sex. We were College freshman roommates; it was late October close to Halloween. It was Friday night and he was out supposedly for the night with his girlfriend Jessica. I, having recently broken up with my girlfriend, was in our dorm alone. After spending one teenage summer with my aunt in South Carolina and sneaking into her room while she was at work I had developed a fondness for wearing panties. And tonight I was girlfriendless and horny as I masturbated.

Matt came back to the dorm, which would be a surprise to me because he was suppose to stay with Jessica at her apartment. I was still in the middle of jerking off and didn't notice him coming in. His mock moan shocked me out of my fantasy masturbation. I was stunned. We sat there for what seemed like hours, but in reality only a few seconds. He stood up and undid his pants I was horny shocked scared all rolled up into one.

He stood at the edge of my bed with nothing but his shirt on. With a large drunken grin Matt sardonically says "you look pretty in my panties." I had never had sex with a guy before but had occasionally fantasized about. He mentioned that Jessica had decided not to go out tonight in order to prepare for the Halloween party they were throwing Saturday night. He had gone to party and was very horny. Matt said not to stop masturbating on his account.

"What were you masturbating to anyway?"

I had forgotten all about what I was fantasizing about but I stuttered I like the feel of panties and stockings and often got off just on the feel.

"Are you Gay?" Matt asked.

"No." I plainly stated although I had fantasized about giving a blowjob.

"Are you?" I asked as I started to move my hand against my crotch, a little surprised that I was still hard.

"NO! Hey I am not the one in panties here." Matt abruptly said

I grinned "no but you are practically naked"

He grinned back and asked if I wanted to jerk him off as well. I was really horny now and so I reached out and grabbed his semi-hard cock. It was different than mine he had more veins showing and was longer than mine. It instantly jumped to life as I started stroking him. That got me excited and I reached under my panties and was now stroking both of us.

Matt moaned and said I was just like some little party slut jerking to cocks at once. I closed my eyes and imagined I was a that party slut masturbating 2 frat boys their cocks inches from my face "put in your mouth" "MMMM yeah you want me to suck you don't you baby?..."

"Only if you want to!" Matt sheepishly said

Had I been vocalizing my fantasy? Whether or not I was I pulled Matt onto the bed above me and licked his cock Feeling Matt's cock jump as I did, got me even more excited I slipped him into in my mouth and heard Matt moan. I had never felt anything like this and I started rocking back and forth his cock sliding between my lips. Not really knowing what to do I tried things my girlfriends had done over the years. As Matt became more excited he started to thrust his hips into me as if he was fucking me. He was getting close and grabbed the back side of my head and thrust in deeper as his cock twitched and jumped in my mouth. Matt let out a guttural ohhh! as he exploded. I was so turned on knowing it was my mouth that had made him shoot streams of hot cum, that I hadn't realized I had already cum in my panties myself.

The next morning I awoke alone to a knock at the door. After throwing on some shorts I answered the door to find Jessica, Matt's Girlfriend waiting. I said Matt wasn't here but as she moved in to the room she said she knew.

"He sent me here to prepare you for tonight."

"Prepare me for what."

She smiled Why our party and your costume of course.

Jessica went on to explain she heard about what happened last night and was going to help me dress as a woman for their party tonight. She also giggled and winked that there was going to be a second party after the costume party. Over the next several hours Jessica took some measurements, we went shopping she picked stuff out so we looked like a just another couple going shopping for clothes. She took me to lunch gave me tips about walking dressing and she even went so far as to buy popsicles and gave me tips on giving a blowjob.

Eventually the party came. Jessica had dressed me in a deep blue full length cocktail dress, with matching silk elbow length gloves and a big blonde wig. I was impressed and I even came in second place in the costume contest, but what I was waiting for was after.

Once the party was over Jessica who had dressed a street hooker came out of the bedroom asking in a "New Yawk City" accent, if we wanted a party? she would give us a good time for the right price. Matt and I laughed but we quickly hurried into the bedroom.

Jessica was waiting on her knees on the bed pulled me onto the bed and began kissing me. Matt sat back and slowly undressed as he watched his new "lesbians" kiss in front of him. I couldn't believe in 24 hours I had gone from a single straight who had had nothing more than vanilla sex to a cross- dressing bi-sexual involved in a three-some.

With Jessica and I locked in a heated kiss, Matt moved up behind me running his hands down my back to my hips. I pushed my ass out a little letting him know he was free to roam.

"My what a job you did Jessica" Matt exclaimed

"She does look quite hot all night!"

I was becoming very wanton and turned around to reach for Matt' cock. Jessica Pulled me off the bed and down onto my knees in front of him. Yelling for me to show matt what I had learned. I quickly gulped his cock into my mouth and swirled my tongue down his shaft as I drew him in deep. I gagged at first still being new at oral sex but quickly had Matt moaning and rhythmically trying to make love to my face. Jessica moved next to me and began to lick his balls. It didn't take long for this double assault on Matt's cock to make him begin to cum. It was much more than I remember the night before but just a good when I pulled off it was running off my lips and down my chin I felt like such a slut at that moment.

"I do love the taste of his cum" Jessica proclaimed as she quickly licked me clean.

As I collapsed on the bed Jessica jumped on top of me and begged me to show her how good I was at my new found oral skills. With her on top of me and her sweet pussy wrapped around my face I began to run my tongue across the inner edge of her lips and quickly targeted her clit. After a few short minutes I had her bucking uncontrollably on my face as she jerked me to orgasm. We all collapsed on the bed and quickly rested for more sexual escapades that evening.

Now 13 years later I still get a thrill remembering that night. Matt and I remained roommates all four years of college. Including our senior year when the three of us lived together. Matt and Jessica got married after college and now live in San Diego Ca. Each year we get together for a vacation maybe I will put some of those times into a letter also.