Date: Fri, 18 Feb 2005 15:17:21 -0800 (PST)
From: Jeremy Rogerson <jeremyrogerson@yahoo.com>
Subject: Jeremy and his Roommate Part 1  TG

While I was growing up, me best friend from down the road had talked me
into sucking his cock.  Between the ages of 13 and 18, when we graduated
high school, I must have sucked his cock hundreds of times.  One thing he
didn't know about me during that time though was that I loved the feel of
women's lingerie as it caressed my body.

I had a small stash of lingerie and stockings building up throughout my
high school years.  When I had a chance, I would dress up in panties,
stockings and a bra and jerk myself off.  Because nobody knew my little
secret, I had to bring my stash with me when I headed off to college.  I
was fearful that my new roommate would find them, so I kept them hidden in
my suitcase under my bed.

This worked fine for a while, I would dig them out on the weekends when he
went home and not have to worry about anyone coming in on me, so I was
starting to spend a lot of time on the weekends in sexy lingerie as I
studied and stayed around the room.  Every once and a while I would wear
the panties and stockings under my pants all day on a weekend, knowing
nobody would see them.  I loved the feeling of the nylon on my legs and
cock.

While I was in college, I was unable to add to my collection of lingerie I
had built up, but I now had a black lacy bra, fake breasts, 2 pair of lacey
panties, one red and one black, and a lot of different stockings and
pantyhose.  I figured by keeping this in my suitcase under the bed, I
wouldn't need to worry about anyone finding the stuff, but I was wrong.

My college roommate was new to me.  I went to school far from home and did
not know anyone there, so on move in day I met my new roommate.  He was
about 5'8", 150, brown hair and brown eyes.  He actually looked a lot like
my friend from home, whose cock I sucked back home.  I was pleasantly
surprised.  We spent the weekend getting to know other people in the dorm
and the lay-out of the campus before classes started.  He lived close by,
so he was going to go home every weekend, so I knew I would have time to
dress up in my lingerie I had.

When classes started, we had some of the same classes, but we also had
separate classes.  I worried that he would rummage through my stuff when I
wasn't there.  I figured that he may look through my drawers, the desk,
etc., but I never expected him to look into my suitcase.  Let me explain
how that day unfolded and how we went from being just roommates to being
intimately involved.

The day had started out the same as the first few weeks.  It was Monday
morning and we had the same first class together and we went to class.
After that class I had another class, and he was able to go back to the
room until later that morning.  So off I went to my class and off he went
back to our dorm room.  While I was in an English class learning how to
write papers and do research, he was back in our room doing some "research"
of his own.

After that class I headed back to the room and when I entered, it didn't
seem as if anything had happened.  It appeared that he had come back after
the first class and started to watch TV.  Later that night I would find out
what he was really up to during that time.  He later went off to class and
I stayed back at the room.  After his class, we met at the Cafeteria for
lunch.  We then each had an afternoon class, then our days  would be
complete.  He went his way, I went mine.

After watching some TV to pass the remainder of the afternoon, we went off
to the Cafeteria for dinner.  We ate and talked like we had the past few
weeks, like nothing had changed.  After dinner, we studied some and hung
out with other guys on the floor and watched some TV.  We decided to get
ready for bed around 10:00 that evening and that is when everything
changed.

When we were both ready for bed and he had climbed up to the top bunk, I
shut off the light and got into the bottom bunk.  We exchanged small talk
like we usually did before going off to sleep, only tonight he wanted to
talk about sex.  He had a girlfriend and was telling me how he loved when
she gave him blowjobs.  I thought nothing of this, he asked me if I had
ever had sex and I answered yes.  Really though, the only sex I had growing
up was giving blowjobs to my neighbor down the street, but I didn't want
him to know I was a virgin, so I told him yes.  Then he told me that he had
been looking for something today and happened to look in my suitcase and
was surprised to see women's lingerie.  I tried to tell him that it was
from my girlfriend, but he knew that they were mine.  After wearing them so
many times, you could see cum stains where I hadn't washed them good enough
after shooting my load onto them.  I was found out!

I was so afraid of what he was going to say or do to me.  I am the kind of
guy that is laid back and don't want to bother anyone and just go on with
life.  I hate to say no to anybody.  He climbed out of the top bunk and sat
on the edge of my bed.  My mind was racing.  What was he going to do?  What
was he going to say?, etc.  He said that he didn't believe that I wore
women's lingerie.  He said that as long as I went along with what he said,
everything would be fine and nobody would know.  I was a bit relieved by
that news, but what did he have in mind?  I was soon to find out.  He
wanted me to dress up for him right then and show him what I looked like as
a woman.

Nobody had ever seen me in the lingerie, now I was going to put it on in
front of my roommate as he watched.  He grabbed my suitcase from under the
bed and opened it up for me and told me to get dressed.  So I took off my
boxers I was sleeping in and put them on my bed.  Of course, I was
extremely excited to be naked in front of another guy, but this was
different than all the times with my friend from home who I blew so many
times.  This time the attention was on me.  I had a huge (for me) boner of
5 inches sticking straight out at this time and he asked me if I enjoyed
this.  I didn't say anything, but my cock spoke for me.

I first grabbed the black lace bra and strapped it on my body and proceeded
to stuff them with the fake breasts to fill them out.  I then grabbed the
black lace panties and slid them up over my extremely hard cock, encasing
it in the smooth panties.  I sat down on the bed and grabbed a pair of
stockings and slid them up my leg into place and finished my
transformation.  He then asked me to stand up, which I did.  He walked
around me looking me up and down.  He kept saying that he couldn't believe
that I wore women's lingerie.  At this point, I was so turned on by being
in these clothes, that I had started to leak some cum and it was visible
through my panties and then he asked me how long I had been doing this.

After telling him that I had loved women's clothing for as long as I can
remember, he just shook his head in amazement.  That lead to the next
question of, did anyone else know about this, which I replied no.  He then
asked if I really had ever had sex before, and I came clean and told him
no, not really.  He then asked what I meant by "not really" and I told him
that I never had sex with a girl, but I had sucked my friends cock many
times throughout high school.  At this point, I figured he knew I liked
men, so what was the big deal.  I told him that I sucked cock throughout
high school, but he didn't know that I wore this lingerie.

He was stating to relax a bit as he continued to question me about why I
did it, if I liked it, what it felt like, etc.  I also at this point was a
little more relaxed, but my cock was still stretching the front of my
panties.  This is when he asked me if I would suck his cock.  He said that
he never had a guy do this before and that he wasn't gay, but his
girlfriend hadn't sucked his cock in a long time.  He said that he was
getting horny and that he needed to be relieved, so I was more than willing
to suck his cock.

He removed his shirt and boxers and I was amazed by the size of his cock.
It had to be at least 8 inches long and 2 inches wide.  Compared to my
cock, this thing was a giant.  I got out of my bed and on my knees in front
of the bed and he walked over with his cock bouncing up and down with each
step.  He was a little hesitant at first to let me touch his cock, but I
reached up and took his huge cock in my hands and began to gently stroke
his shaft with my hands.  It had been a couple of months since I sucked off
my friend from high school, so I was glad to have a cock in my hand again.
What was even more exciting this time though was the fact that I was able
to suck cock in my lingerie.  After spending some time stroking his cock
and playing with his balls, I decided it was time to get down to business.

I took a hold of his cock at the base and stuck my tongue at the base of
his shaft on the underside and slowly licked towards the tip of his cock.
As I was doing this, I could tell that he was feeling more and more
comfortable by the moans escaping his lips.  I repeated the step one more
time and licked my way from the base of his cock to the head.  I then
opened my mouth and took his cock head into my mouth and began to lap at
his cock head with my tongue.  I pulled back from this and wrapped my hand
around the base of his cock and brought a nice load of pre-cum to the tip
of his head.  I licked that from his slit and savored the taste of cum once
again.  This one was saltier than my friend from home and tasted a little
better.  I then took his cock in my mouth and tried to swallow as much of
this monster as I could take.  I think I was able to get about three-
quarters of this giant in my mouth.  I slowly started to bob my head back
and forth over this cock, as he moaned his pleasures from above.  After a
few minutes of sucking his cock, I pulled off and started to stroke his
cock again for him.  Slowly at first, then picking up speed.  This was
really turning him on and he was lost in the moment.  I started to suck on
his cock again, while at the same time stroking his cock.  As I pulled back
on his cock, my hand followed my mouth up his cock and as I descended on
his cock, my hand went down his cock.  After a few minutes of this I could
tell he was breathing harder and was tensing up, so I knew he was close to
shooting his load.

I stopped sucking on his cock and replaced  my mouth with my hand stroking
him ever so gently at first, then faster and faster.  I took my tongue and
once again licked the underside of his cock from the base to the tip and
that drove him wild.  A few more strokes from my hand and the next thing
you know, he's shooting a huge load of cum onto my face and "breasts."  I
think he shot at least five good loads of his hot sperm onto my face before
he was finished.  When he finished, he looked down and was amazed at how
much cum he had shot.  I scooped some from my face as he watched and tasted
the salty treat.  I then again grabbed his now softening cock and placed it
in my mouth being sure to get the last drop sucked from his cock.  When I
was done, he put his boxers back on and sat down and told me that I gave
him the best blowjob he ever received.  I grabbed a towel and cleaned as
much of the cum from my face as I could and sat on my bed again.

We talked a little more about this before heading off to sleep that night.
He couldn't believe that I sucked cock and wore women's lingerie.  He did
mention that my secret was safe with him as long as I was willing to
service him whenever he wanted.  Of course I told him yes.  My favorite
thing to do was to suck cock and make the man happy and satisfied.  He
climbed back into bed and I stripped out of the lingerie and put it back
into the suitcase and laid back in bed naked.  My cock was extremely hard
and aching for relief, so I figured since I just sucked his cock, he
wouldn't mind if I jerked off.  So as I stroked my cock, I replayed the
nights events in my head and before long, I was shooting my own load of cum
onto my stomach and chest.  I grabbed the towel and cleaned myself up as
best I could and went to sleep.

That night was the first time another man had seen me in lingerie and
turned out to be the beginning of a good four years of college.  Whenever
he wanted his cock sucked, I was there for him.  If he went home for the
weekend and he and his girlfriend did not have sex, then I knew that Sunday
night when he returned, I had a cock to suck.  We stayed together as
roommates all throughout college and nobody else expected anything.

There were more memorable nights that we shared together in college and
even a few since then, but the first time was best.  If you would like to
hear more of my time spent with my college roommate and my lingerie, write
me at jeremyrogerson@yahoo.com.  I look forward to hearing from you and
writing about another night we shared.