Date: Wed, 12 May 2004 13:00:27 -0700 (PDT)
From: Jeremy Rogerson <jeremyrogerson@yahoo.com>
Subject: Jeremy, Aaron and Jack as Crossdressers

     One day I was on-line chatting and looking for another local man that
had the same interests as I had and also looking for some great sex.  As
luck would have it, a man came on and was looking for the same thing I was.
After chatting for a few minutes on-line, we decided to meet at a hotel
nearby for a great night of sex later that night.

     We were both looking for another guy who liked to dress in women's
lingerie.  We lucked out and met each other.  I had never met nor told
anyone else that I liked the feeling of panties, a garter belt and
stockings on my body.  I couldn't believe I was about to go meet with
another guy and show myself to him in lingerie.  He was also going to bring
along some lingerie for himself and we were going to have a great night of
sex.

     We were to meet in a bar connected to the hotel at 7:00 that night.
So I quickly returned to my apartment and gathered my garter, stockings, a
pair of panties and a matching bra and quickly left to meet my "date."
When I got there, I was able to locate Aaron by his description he gave me
on-line.  As I nervously approached him at the bar, I thought about leaving
and skipping this encounter because I was so nervous.  When I got beside
him, he also recognized me by my description and we introduced ourselves,
and I joined him for a drink to relax a little.  We did not talk about the
plan for the evening, so no one around us would know what we were doing.
After 15 minutes or so, we went to get our bags of clothes and to get a
room for the night.

     As we were heading to our room, I was extremely nervous.  Two hours
earlier and I had never heard of this man, and now I was on the way to a
room to have sex with him.  I guess I need to explain that I was 23 at the
time and he was 36, so the age difference along with not knowing anything
about him had me worried.  He seemed like a nice guy from talking with him
and I had experience with other men, so I was not worried about that.  My
worst fear was that something extremely bad was going to happen and people
would now that I liked other men and liked dressing in women's lingerie.
Although nothing major happened, I did learn a lesson about meeting a
stranger in a hotel room.

     When we got to the room, he opened the door and we entered the room.
He shut the door behind him and locked it so we would not be disturbed.  He
was the more dominant person and he was in charge of the night.  I was
submissive and did what was asked of me.  I was never one to say no and
that is how I first got started in sucking cocks.  My best friend in high
school coaxed me into sucking his cock and I didn't say no because I didn't
want to hurt our friendship.  For the next 4 years, almost every time we
were together and alone, I sucked his cock.

     We put our bags down, and we went to the bed and sat down and we
talked a little to get to know a little more about each other and he was
able to calm my fears.  After a while, Aaron decided we had wasted enough
time, and that we should "get down to business."  We decided to increase
the anticipation, we would get dressed in our lingerie in separate rooms.
So, I went to the bathroom to get ready and Aaron stayed in the room to get
dressed.  I should have been suspicious when he insisted that I go into the
bathroom to change.

     As I started to get undressed in the bathroom, my heart was really
racing.  As I stood there naked with my 5" cock at full attention, I began
to fantasize about what was going to happen in a few minutes.  First, I
grabbed the black lacy bra and put it on, and placed the breast forms into
the cups, giving me nice looking breasts.  I adjusted my breast forms so
they were not noticeable.  Next, I grabbed the garter belt from my bag and
put it in place.  I then slowly rolled the black silk stockings up each of
my legs, getting them ready to fasten to the garter.  But first, I needed
to put the panties on to complete the dressing for sex.  I grabbed the
black panties from the bag and pulled the panties up into place, totally
covering my 5" hardon.  The bulge in the front of the panties was quite
noticeable.  This got me thinking, I wonder how big Aaron's cock is?  I
would find out soon enough.  I finished by clipping the straps on the
garter to the stockings and I was ready to go.

     A few minutes later, Aaron said he was ready and that I could come out
now.  When I opened the door and turned the corner into the main room, I
was extremely shocked at what I saw.  First, there was another man there
with Aaron and secondly, Aaron was completely hairless except for the hair
on his head.  I on the other hand, had hair all over my body.

     When I saw the other guy with Aaron, I was very scared and nervous.
He immediately told me that, Jack, was his boyfriend, and that he wanted to
watch and join us.  I was scared.  This was the first time anyone had seen
me in lingerie, and now there were 2 guys there.  Jack turned out to be a
good guy, but when I first saw him I was frightened.

     Aaron had calmed me down about Jack, telling me they had lived
together for 3 years and that I had nothing to worry about.  He had this
planned as soon as we were off-line.  He told me not to worry and to enjoy
the evening.  He told me how they had lived together and how Aaron acted as
if he were the woman of the house.  Since Aaron did not go out much, he was
able to completely shave his legs and chest.  He thought that I also would
be likewise, but I was not that far into it.

     Aaron looked great in his lingerie.  A pink thong and matching bra and
also white stockings, with a pair of high heeled shoes.  The bra was also
filled with breast forms as was mine.  He also had on bright red lipstick.
I also noticed a huge bulge in the panties, that left very little to the
imagination.

     Aaron was a little disappointed that I was not shaved like he was, and
when he mentioned it, Jack told him to shave me.  Aaron asked me and I
refused because I see to many people, and I didn't want to be hairless.
Jack and Aaron insisted that I shave in order to look more feminine for the
night.  I agreed that they could shave some, but I had nothing to shave
with.  Of course, Aaron had in his bag, a razor and shaving cream.  We
ended up shaving most of my chest hair and a good portion of my leg hair
off.  Just when I though we were done, Aaron told me I needed to shave all
of my pubic hair, or they would not have sex with me.  I was very hesitant
to do this, but I had come this far and wasn't going to let this stop me,
so off came my pubic hair, except for a small patch just above my cock.
Luckily, I did not have a girlfriend at the time, so no one would know.
After rinsing off, I was ready to go again.

     Jack was watching TV as Aaron had shaved me.  When we entered the
room, Jack told us "I'm glad my two women are ready to serve me."  Jack
told Aaron to apply some of the lipstick to me and we were ready to begin.
To begin, Jack wanted "the lesbians" to get in the 69 position and suck
cock while he watched.  As we both got into position and Aaron and I pulled
our cocks free from the panties, I was shocked at how big Aaron's cock was.
It had to be 9 - 10 inches long and thick.  My 5 inch cock paled in
comparison.  I had sucked the cock of my high school friend years earlier,
but his was about 7 inches long, and not nearly as thick.  This was going
to be fun!

     As we sucked each others cocks, you could hear Jack on the other bed
softly moaning, as he was stroking his cock while he watched us.  We
couldn't have sucked cock for more than 5 minutes before Jack told us to
stop.  When I noticed Aaron's cock, I saw my lipstick on his cock.  That
was very arousing.  He told us to stand and remove our panties, so he could
see both of our cocks.  Aaron quickly had his off, but I took a little
longer because I had to undue the garter first to get them off.  It was
quite a rush to be standing in women's lingerie, being smooth shaved and
with two guys with nice cocks to suck on.

     Jack stood up and asked us to remove his clothing from him.  It didn't
take long and he was completely naked.  He, just like Aaron had a very big
cock.  It too was about 9 - 10 inches and even thicker than Aaron's cock.
We were to both get on our knees in front of Jack and worship his cock as
the other one sucked it.  I was eager to get his cock in my mouth, so I
started sucking it as Aaron told Jack how big his cock was and that sluts
like us were lucky that he allowed us to suck it.  Aaron wanted to suck
Jack's cock, so we switched as he sucked and I praised Jack's cock and his
willingness to allow cocksuckers like us to suck his magnificent cock.
Aaron and I kept taking turns sucking cock and worshipping his cock.  Jack
then decided it was time to get started.

     Jack decided that since I had the smallest cock, I was going to be
fucked first by him.  I was told to bend over the bed and get ready to be
fucked.  I had never been fucked before and told Jack that and he was glad
that he was going to be my first.  He told Aaron to kneel on the bed, so
that his cock was in front of my face and so I could suck it while I was
getting fucked by Jack.  Aaron got in place and I started to gladly suck
his cock while Jack was applying some lube to my ass and his condom covered
cock.  He slowly worked in one finger then two fingers, then three, slowly
stretching my ass and preparing it for entry.  As he was doing this he made
lewd comments about the two "lesbians" who were going at it on the bed.  I
would suck Aaron's cock for a while, then stroke it and lick it like an ice
cream cone from the base to the tip.

     Jack was ready to begin fucking me and he slowly inserted the head of
his cock into my ass.  At first, it was excruciating, but then the pain
subsided and was replaced with a great feeling.  He slowly pushed more and
more into my ass, stopping just long enough to allow me to adjust to the
huge cock in my ass.  When he was fully inside me, he pulled all the way
back out and then slammed his cock back into my ass.  He left his cock sit
there for a while, then slowly began to fuck my ass.  He continued to
thrust this cock in and out of my ass, all the while commenting on myself
and Aaron, the two "lesbians."  Aaron was beginning to fuck my face at this
time.  He was so turned on by Jack fucking my ass, that he started fucking
my face.  Jack began increasing his speed and was really working his cock
in and out of my ass.  I noticed that both Jack and Aaron began breathing
heavier, so I knew that they were both close to cumming.

     Then I realized I hadn't asked them to pull out before they came,
because I did not want cum from strangers inside me.  Luckily, Jack had a
condom on as he was fucking my ass, but Aaron did not have a condom on as I
was sucking his cock.  With Aaron, I started to taste some pre-cum that was
starting to leak from his cock.  It was salty, but tasted great.  Within
minutes, both Aaron and Jack had pulled their cocks out and were going to
shoot their cum all over me.  Jack ripped the condom from his cock and
stroked his cock until he was shooting torrents of cum onto my ass and
back.  Meanwhile, Aaron was stroking his cock in front of my face and was
soon shooting his load of cum onto my face and into my hair.  What a sight
it was to have a man dressed in lingerie shooting a load of cum onto my
face.  When he was done shooting, he rubbed his limp cock in some of his
sperm from my face and told me to clean his cock, which I happily did.

     At this point, I was a little sore in the ass, but extremely happy to
have sucked cock and have hot sperm all over my lingerie and body.  I was
also extremely horny now and ready to cum in torrents.  Jack ordered that I
lay on my back on the bed and have Aaron stroke me until I came.  That
didn't take long before I was shooting more cum onto myself, hitting not
only the garter, but one shot came up to my bra.

     We were all exhausted now, but Jack was not done.  He wanted me to get
in the same position over the bed and Aaron and he were going to switch
positions.  So I got into position and Aaron pulled a condom over his hard
again cock and slowly inserted his cock into my awaiting ass.  Jack knelt
in front of me with his cock hard again and I took it into my mouth and
started sucking it as Aaron pounded away on my ass.  It didn't take very
long this time before Aaron and Jack were ready to shoot their second load
of cum onto me.  Aaron was first and pulled his cock from my ass and shot a
load onto my ass and back.  As he was almost finished, Jack pulled his cock
from my mouth and shot a load of fresh cum onto my face and hair.  He also
rubbed his cock into some cum and had me lick him clean.  By this time, I
had quite a bit of the gooey cum on me and Jack told me to fix myself up.

     When Aaron and I got to the bathroom, I realized what he meant.  My
lipstick was smeared and my breast forms needed realigning and my stockings
needed straightened out.  Aaron put more lipstick on for me and we went
back out into the room with Jack.  I though we were done for the night, but
I was wrong.  Jack wanted me to suck Aaron's cock while he watched.  I got
on my knees in front of the bed and grabbed Aaron's cock in my hand, and
stroked it back to life.  He was at full size within a minute and ready to
go.  Jack told me to give him the best blowjob, because Aaron was his "best
lady, and she deserved it."  This was his reward for setting this up for
tonight.

     It had been 4 years since I had sucked my friends cock, and the first
time back into it and I was about to give another blow job.  Lucky for me,
I really like to suck cock.  I grabbed Aaron's cock and slowly ran my
tongue on the underside of his cock from the base to the tip.  Aaron's cock
flinched as I did this.  He let out a big moan of pleasure.  I repeated
this two other times before I began to suck his cock.  I went down as far
as I could on his huge cock, but was only able to get about half of his
cock in my mouth.  I slowly bobbed my head up and down his shaft while my
right hand stroked the bottom part of his cock.  As I pulled my head up, my
hand would come up, working his cock for his love juice.  As I pulled up
one time, I did not go back down until I had sucked on the head of his
cock.  I sucked on the head like a vacuum, all the while my tongue was
caressing his cock head.  I pulled off completely and slowly stroked his
cock with my hands.  The last pull, I grabbed firmly around the base and
squeezed the cock to force out a drop of pre-cum.  Sure enough, I was
rewarded with a glistening, salty drop of cum at the tip of his dick.  I
licked it off and his cock twinged with excitement.  I once again, slowly
licked the underside of his cock from the base to the tip causing him to
moan loudly with pleasure.  I wanted to cool him down a bit before I
continued, so I took his balls and sucked them in my mouth one at a time
for a few minutes, giving him time to cool off.  I licked the underside of
his cock a few times before I started to really suck his cock.  I bobbed my
head up and down his shaft, all the while keeping my hand in motion
stroking his cock as my head pulled up.  I once again sucked on the head of
his cock, while I stroked his cock with my hand.  Twirling my tongue around
his cock head cause some more moans.  I realized it wasn't going to be long
before Aaron was going to cum, so I intensified my efforts.  I started to
suck his cock, taking as much in my mouth as I could, making sure that my
tongue was rubbing up and down the underside of his cock.  Aaron really
began to breather heavier and moan louder, so I knew it was about time for
him to cum again, and sure enough he did.  It was the biggest load of the
evening and completely covered my face with his cum.  He thanked me for the
best blow job he ever had.

     Jack was so impressed, I had to do the same thing to him.  Which I was
happy to do.  By the time I was done blowing Jack, they had each came 3
times and I had only cum once.  This was not lost on Jack or Aaron, so they
asked me to jack off in front of them as they watched and shoot my cum onto
myself.  I did as I was told and was soon shooting cum onto my chest.
Aaron grabbed some cum from my chest and fed me my cum.  I had never tasted
it before, but it was almost like Aaron's.  He continued to feed me a
mixture of our cum that had been shot on my body throughout the night.

     With this, Jack was ready to go to sleep for the night and wanted
Aaron and I, the "two lesbians" to sleep one on each side of him.  But
first, he wanted us to remove everything except for a pair of thongs, so we
could have as much of our smooth bodies in contact with him throughout the
night.  We fixed up our lipstick again and went out to go to bed for the
night.  We kissed each other good night, which was the first time I kissed
another man.  It wasn't long before Jack and Aaron were asleep, but I was
up for a while replaying the nights activities in my mind.

     Earlier I hadn't even thought about letting another guy see me in
lingerie, and now here I am sleeping with two men who not only saw me in
lingerie, but who I had sex with.  With this experience, I really began to
love to suck cocks.  I don't need reciprocation, as long as I can suck a
cock.  I couldn't believe I had done this and I couldn't believe, I was
shaved and cum covered in lingerie in a hotel room with two strangers from
a few hours earlier.

     Unfortunately, in the morning, I was told by Jack and Aaron that they
had taped parts of the prior evening showing me in lingerie and sucking
each of their cocks.  They told me that if I did as they wanted in the
future, I would not have to worry about anything.  Now I was scared, and
knew why I shouldn't have met a stranger in a  hotel room for sex.

     If you would like to hear about the next time Jack and Aaron called on
me, let me know at jeremyogerson@yahoo.com.