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Message-ID: <41914asstr$1050711004@assm.asstr-mirror.org>
NNTP-Posting-Date: Fri, 18 Apr 2003 13:07:19 -0500
Reply-To: "Samantha Hopkins" <bedroomcd@hotmail.com>
From: "Samantha Hopkins" <bedroomcd@hotmail.com>
Subject: {ASSM} Story: First Time with Mike (MM Crossdressing, True)
Date: Fri, 18 Apr 2003 20:10:04 -0400
Path: assm.asstr-mirror.org!not-for-mail
Approved: <assm@asstr-mirror.org>
Newsgroups: alt.sex.stories.moderated,alt.sex.stories
Followup-To: alt.sex.stories.d

Story contains explicit material...Do not read unless you are allowed to and
will not be offended by explicit material




I had just broken up with my live in girlfriend a few weeks earlier.  I was
still in that phase where I was thinking about her constantly.  Even though
we weren't compatible, by any stretch, she was so fantastic in bed, that I
desperately wanted it to work.

My long time friend Mike made the hour drive north to see me Saturday night
and we decided to do the BARmuda triangle.  There were three bars in town
within walking distance,  we would have a few drinks at each of them.  We
were pretty wasted when we left the basement bar that night.  We surely
shouldn't have been driving those back roads, but we managed to get back to
my place pretty well.

We both went up to my loft apartment and had some more drinks.  Mike brought
out some Joints he had and we puffed away.  It was clear that he wouldn't be
going home after a while.  I told him he could have my bed.  I would sleep
in Helen's bed.  Helen and I  had started out as "room mates" and things had
progressed from there.  She was a sex fiend.  She would do anything.  The
problem was she would do anything with anybody. As dumb as it was, I missed
her terribly.

Mike went off to bed after a while.  I puffed on some more of his smoke then
headed to bed myself.  I got into bed and could instantly smell her perfume.
As I laid in her bed getting comfortable, my feet kept feeling something
near them.  I caught it with my toe and brought it to hands reach.  I
quickly realized it was a pair of her panties.

"I wonder who she was screwing when these got left here?" I thought
bitterly.

"I want to try things while I am young" she argued with me before she moved
out  "What's wrong liking to be fucked?"

I laid there, smelling the sultry perfume she wore and a hint of her scent
on the panties. Man I missed her.  She had moved out in a terrible haste,
she grabbed a few things and was off to make someone elses life miserable.
But it had been nearly a month and she hadn't bothered to come back.  Too
much booze I guess, but I decided I was going through her drawers and
closets.  She hadn't taken hardly anything.

Mmmm her Jordache jeans. I held them up to myself as if  I was going to try
them on. God she wore them tight.  I went through her other drawers too.  I
came across a lacy red satin corset outfit, with long garters and matching
panties and stockings.  For some reason I decided to just see what it would
feel like to put on her stocking.

Before long I was gently and carefully unrolling the thigh high nylons up
each leg.  The sensation was awesome.  So sexy..so wrong.  The beer and the
pot easily squelched the voices of guilt and reason.  I stepped into her
shiny satin thongs, they electrified every nerve on my legs as I pulled them
up over the thigh high stockings.

"Wow" I said aloud as her thong parted my butt.  "no wonder she wants to try
as many guys as she can"   The feeling of the thong and unfamiliar pressure
on my ass drove me on.  I unlaced her corset as far as I could.  While I was
bugger than Helen in every way I was able to get the corset around me.  I
messed with the lacing, pulling it as tight as I could stand.

It took an eternity to attach the garters to the nylons only to realize that
I wish the panties were put on last so that I could take them off easy.  But
the second time I was much faster.  By then I was comfortable enough to pull
the lacing even tighter on the corset.

"I could almost fit into her Jordache Jeans ! "  I thought to myself.  I
couldn't believe how small her red satin corset made my waist look as I
stared at my reflection.  I wasn't hour glass figured, but it sure was
feminine waist.

After some internal deliberation, I got the courage to tip toe back into the
living room to grab another joint.  While I imagined all the horrors of what
my life would be like if Mike were to see his childhood buddy dressed like a
Saloon whore from a western, I savored every step, feeling the tight corset
compressing my middles and the thong notifying me with it's own gentle
pressure against my butt.  Small wonder Helen was always so horny.

Instead of grabbing and running, I sat on the couch and lit up.  As I
finished the joint I got hornier and hornier.  More than a few times had I
watched her getting fucked by guys.  So desperate to keep the relationship
towards the end, but sheer fun at first, I had enjoyed many threesomes with
her.   She was so into it.  So self consumed with her own pleasure as the
"guy of the moment" thrusted his cock into her.

"Could it feel that good?' crossed my mind as visions of her riding my own
cock flashed in my mind.  "I wonder what it's like to be her?" turned to "I
wish I was her?"

By now I was pretending to be Helen, imagining what it would be like to be
fucked two, three, four times  a day. I imagined all these guys buying her
clothes, dinner, booze, drugs in hopes of having sex with her.  I obsessed
with the thoughts of her getting laid by all these guys, savoring the shape
and feeling of each guy's cock and how they used it.  Feeling them cum.

I made my way to the bathroom, choosing to sit to pee, like her.  As I sat
there tinkling, my heart raced as my mind turned to thoughts of Mike sound
asleep in my bed.

"This is crazy!" I thought to myself as I seriously considered the
possibilities.  Mike had been my friend since childhood.  It was no wonder
he always has such hot girlfriends,  his overdeveloped pecs and his
washboard abs.

"I can't do this"  I said softly aloud.  I though of the many time I had
looked at his naked tanned body at the gym.  His massive dark cock earned
him the nick name "the meat".  But even as pulled the thong panties back up
I just couldn't believe I was going to try this.

Not sure what to expect, I grabbed the Vaseline.  I couldn't believe I was
doing this.

"What If I don't have time to get ready?"  I froze at the door to the
bedroom.  What if he likes it and thinks I am a girl.  I tiptoed-ran back to
the bathroom.  I slid Helen's panty down.  I opened the Vaseline and scooped
my finger into the jar.  I gasped as the cool jell touched my anus.  My hole
pulsed around my finger as I tried to push the sticky greasy lubricant up
inside me.  Afraid this would not be enough, I grabbed the bottle of hand
lotion Helen had left behind.  With haste I opened the flip nozzle and
pressed it into me.  The Hard plastic cap scrapped as it entered me.  I
squeezed and rolled the hard plastic bottle, forcing some air and lotion
inside me.

I wiped the excess lubricant off and washed my hands and spent a few moments
to retighten the lacing on the corset.  My waist was even smaller!  Almost
automatically, I reached in the medicine cabinet.  Finding the half empty
bottle of Helen's Perfume I sprayed a puff on my neck, chest, and crotch.  I
had definitely over done it, but was way too drunk and high to care.
Grabbing the Vaseline, I headed to the bedroom door.

My heart was racing as I crept into my bedroom.   My breathing was short and
shallow, not from the confining corset but from the hopes excitement and
fears that ran  simultaneously through my head.  I could see Mikes sleeping
silhouette in the dark room from the minimal light which came through the
window.

"What would he say?"  I thought as I clenched the Vaseline jar in my hand
and just started at Mike.

"What would he do?" I wondered as I looked down at my narrow waist held in
the corset, which was still shiny in the dim bedroom light.

"I am crazy for considering this !! "I decided I would sneak under the
covers

"This could ruin your life !!" was the last panicky thought as I gauged
where his hips ought to be, and pulled the covers at the side of the bed up
over my head.  I waited to see if my movement so far had awaken him.  no
movement other than his regular breathing which made me realize he was
really out.

I crept across the bed.  Pausing after each move.  Trying to get closer and
closer.  Inch by inch.  It took forever.  The garters pressed into my butt
cheek as my snaking movements tugged at the stockings.

"I gotta be getting close !" I thought when my knees were under the covers.
By now I could feel the heat of his body and the electricity of his
presence.  After waiting another moment I pushed another inch forward.  The
smell of his musk was strong, strange yet familiar, natural and good.   I
lunged delicately forward and froze as my nose pressed through his pubic
hair and gently bumped his skin.

"Oh my god !" I thought as my lips probed the hair looking  for a landmark
to guide me under the dark stuffy covers.  I inched my way lower hoping to
get contact with him.  My chin brushed what I instantly knew to be his cock.
I lowered myself down after waiting to see if Mike was still sleeping.  My
nose brushed his soft penis.

"This has been in a lot of girls" crossed my mind as I parted my lips and
engulfed his flaccid member.  It's taste was wild but undescribable.  It
jumped in my mouth as pushed the skin back gently with my lips and my tongue
invaded his piss hole.

His throbs began slowly.  His cock filling.  Getting larger with each pulse.
Filling my mouth with flesh.  By the time it was hard I was reeling from it'
s size.  No longer able to keep even half of the shaft enveloped by my wet
sucking mouth, I began stroking it with my hand.

Suddenly Mike roused. And rolled gently onto his back.  I never let the
bulbous head of his cock out of my mouth.  I rolled with him. His new
position allowed me to take more of him into my eager mouth.  As I drew in
harder on his rigid prong, I would occasionally make sucking sounds.

I pressed him hard  against  the back of my mouth, knowing the dream of any
guy is a girl who can deep throat.   I tried to push it down but couldn't.
Suddenly Mikes hands were caressing my head.  Fondling my ears and hair.   I
took several deep breaths of the musky hot air under the covers.  I pushed
his cock against the back of my mouth.

"Did he know it was me?" I wondered as I felt his hands gently press the
back of my head.  With a smooth thrust of his hips I felt his penis break
the invisible seal on my throat.  Startled I froze as I felt the entire
length of his shaft move by my lips.  Though I was gagging like convulsions,
his ample cock completely blocking my throat, kept me from vomiting.  Before
I panicked for air, his hips relaxed and his cock slid back leaving only the
head and what part of the shaft my mouth covered.

"I did it !" as the tears from the gagging streamed down my face.  Still
frozen, I breathed through my nose.  My mind scrambled to process what had
just happened and calming myself down.  Within a minute or two I began
moving again, sucking away at his cock.

After a calming a bit more, I got my courage up to try doing it again.  I
guided his penis to the back of my throat and pressed.  As if on cue his
hands firmed their grip and his hip moved up.  His head broke through my
tight throat much easier as I felt his shaft race past my lips.

"Be Calm...Relax..Be calm"  I said to myself after the first gag spasm.
"Control it.Control it"

After another gag, his hips relaxed and his shaft receded from my throat.
There was only the briefest delay before I was sucking again on his cock.
Again getting my composure for the third try.

"This time I am going to really relax" I told myself as I hyperventilated as
best I could through my nose.

"Calm down.. breathe deep...Just let it slide in" and with that I put his
cock to the entrance  of my throat, without delay  and little resistance his
cock entered my throat.  My hands reached out and grabbed the firm globes of
his muscular ass

"Relax.relax.." I calmed down a lot and just allowed him push it all in me

"I'm Doing it !!!  I am Doing it !!! I shouted to myself.  Even though I
would gag once or twice with his cock in my throat, it became easier and
easier.  Before long I lost count and began measuring my success on his
moans of pleasure and by how much of his ball I could touch with my lips and
nose.

"Mmmmmm . Oh wait baby" he said in his sexy lust filled voice ".wait, wait,
wait,..you going to make me cum"  His cock spasmed in my mouth.  My mouth
filled with the strong taste of what I instinctively knew was cum.   I was
shocked by the flavor and sensation, wondering what I would do if he really
came.  After he relaxed I sucked again on his cock.
I began thinking about Helen.  She had done this with dozens of guys.

"No wonder she loved it" I thought to my self as I pushed Mikes cock without
his help down my throat.

"Oh baby.Mmmmmm.Oh baby" he moaned as his balls touched my nose.

"If this is good"  I thought to myself " I got to have him in me"

I fumbled around and relocated the vaseline.   It was now warmed to body
temperature. I applied the greasy jelly to his rigid shaft, I couldn't
believe how big he was.  As I smeared the knob I realized this was huge
compared to my puny six inches.

One last scoop of the Vaseline I plastered between my ass cheeks.  The
thought that he may be drunk enough not to know I wasn't some bar slut, made
me opt to keep my own aching cock covered as I lifted my leg over him  and
straddled his torso.

His hands massaged my knees as I pulled the covers back.  The cool fresh air
was what I needed, I was sweating like crazy.  The same cool air made me
feel so naked and exposed.  The anonymity of the covers was gone, but the
room was so dark only silhouettes were visible in the dim light which
filtered in from the window.

After getting my composure and getting into a comfortable position, I
reached back and grabbed his rock hard love club.  I raised myself up on my
knees and positioned the head against my anus.  With a little movement I was
able to move the greasy thong out of the way.  After confirming his position
in my mind I eased myself back onto him.

"AAAaaaaaaaaaaah !  " I gasped as incredible pain shot  though me.  I
instantly raised myself off of him.  My hole puckered in spasm.  I couldn't
believe the pain.  I calmed myself and repositioned for another try.  Slower
this time much slower.  I got to where I was just moments ago, trying to
relax and accommodate him.  I pushed back a centimeter more and monitored
the pain level.  When I was in control, another centimeter.  His cock
throbbed

"Oooh''  I whispered and I sprang off him again.  My body reeling in pain. I
positioned him again and repeated this four or five more times.  Each time I
got him a bit further into me.  Each time I tolerated the burning tearing
pain for seconds longer before hopping back up and forcing his withdrawal.

My breathing was shallow and panicked, I tried to calm myself down.  I
realized I was making progress, but how much would he tolerate?   How much
more could I stand?  I realized that I wanted to do this.  I need to try
this.  Just this once.  As I repositioned him against me for another Mike's
hands fondled the garter straps holding my stockings up.

Slowly I descended back on his cock, quickly reaching the place where I
backed off before.  I panted as I got control of myself.  Mentally preparing
for the next push.  I relaxed my legs for an instant and I felt the bulbous
head of his penis burst into me.  I was in excruciating pain but as I moved
to dislodge him from me the pain skyrocketed when I attempted to pass his
head back out of me.  I froze, wanting to desperately get him out of me but
too afraid to endure any more that I already was experiencing.

As the seconds passed like weeks, the pain subsided to manageable levels.  I
still didn't dare to move.  Just as I was almost ready to try to go down
further Mike cock throbbed.  I gasped as I felt his expanding inside me.

Slowly I proceeded to back down.  A little further each time.  Now Mike was
caressing my ass with his masculine hands as I went lower with each little
bob on his cock.  I had reached bottom, or so I though I thought, by the
time his hands were around my trimmed corseted waist.  I put my hands on his
firm pecs and whimpered as he pushed me down to meet the upward thrust of
his hips.

By the time he had thrust into me five or six times, it didn't hurt.  Soon I
started making some little movements to meet his thrusts.  After a few
minutes I found myself sitting back with my arms and hands supporting me
from behind.  I found myself trying to get every millimeter of him into me.

Soon I was riding him like a rodeo pony. My hips bucking fast and
rhythmically only pausing to occasionally press my ass down onto him and to
grind his hips into me.  Mike was pistoning in and out of me with fury.

It was like a daze, like watching someone else.  Every thought, every nerve,
every fiber in my body was focused on the sensations and feelings and mikes
Cock plunged in and out of me.  In and out, In and out.

I was so consumed with being fucked that I don't remember how my own cock
got free of the panties.  At some point, Mike began pumping my cock with his
huge hand, his other hand cupped the globe of my ass, controlling the pace
and depth on which i bounced up and down on his cock.  Slowing my bucking
down, then speeding my riding upHis hand on my butt would tell me how high
to ride up on his cock.  At some points he would guide my rise up his shaft
up so high that the bulging head of his hard cock was the only part of him
inside me.  Then I would fall back, as the full length of his shaft drove
into me.I noticed a change in Mikes thrusting
rhythm,  He pressed me down onto the full length of his shaft, and jammed
his hips into me even further. I felt the pulsing of his cock inside me.
Then under my belly
button I felt his cum shooting into me.  Spraying and spraying as he moaned
and cried out in ecstasy.

My own  orgasm erupted as Mikes cum filled my insides."Ahhhhhhhhhhh" I I
gasped as my cum sprayed
everywhere, all over his belly chest face.  I couldn't control myself!!   I
couldn't breathe!!  I had never had an orgasm like it before !! It was
amazing. I was
spent.  Exhausted.  Finished !!  I had never had an orgasm that intense in
my life.

As I returned to normal I could now make out Mikes face in the Dawn's light.
His cock was still buried in me.  It crossed my mind that his cum was inside
me too.
We stared at each other, in deathly silence.   I realized again how crazy
this all was!  Here I am in a girls corset with my friends cock inside
me.  I was embarrassed, and feeling more awkward
by the second.  What would I say? How would our friendship survive this?
What if everyone found out?

I was feeling so stupid so awful!  I felt awful but at the same time I had
just had the best
sex of my life.  I had never had an orgasm like that.  As the panic
descended and the tears started, Mike grabbed my waist and in his masculine
way, pulled me down on top of him.  Totally shocked, I was hardly able to
move my tongue as he
kissed me forcefully and passionately.  As our kiss parted he caressed my
face and looked deep into my teary eyes he said "That was so totally
awesome"

-- 
Pursuant to the Berne Convention, this work is copyright with all rights
reserved by its author unless explicitly indicated.
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