Date: Sat, 2 Nov 2002 21:08:58 EST
From: HappyD172@aol.com
Subject: 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.

David S.
Rhode Island