Date: Thu, 12 Aug 2010 18:32:37 -0700 (PDT)
From: Jenette LaSalle <jenettelasalle@yahoo.com>
Subject: Another Night Out

      I know what you're going to say - not another Halloween
cross-dressing story.  But Halloween is a classic time for those of us who
like to garb ourselves in the accoutrements of the opposite sex, and my
last outing during that time was quite an adventure.
	As I've mentioned in my previous postings, I'm a pretty typical
example of the cross-dressing guy: tall, slim, professional, and for all
outward appearances a regular everyday straight laced "Joe".  But since I
was just a kid I've always had a hankering to don a skirt and heels for fun
and excitement.  I only dress up and go out a few times a year, but when I
do it I really enjoy it!
      I consider myself to be "straight" - but over the last few years I
found myself occasionally enjoying the company of men while I was dressed
as a woman.  The first time was really nothing more than a drunken tryst in
a dark parking lot.  A few too many cocktails at the local TG bar, a few
hot dances with a persistent tranny chaser, and before I knew it I found
myself bent over the hood of an SUV with my skirt pushed up, panties pushed
aside, legs spread wide, and a cock stroking in and out of my virgin ass.
Much to my amazement I found I enjoyed the experience.
      The next time was a bit more deliberate.  I had enjoyed my first time
letting a man have his way with me while I was dressed in a skirt and heels
so I wondered if I would enjoy it a second time.  Curiosity led me to an
ardent internet admirer who wanted a last "fling" with a t-girl before he
tied the knot.  We had conversed online for several weeks until I finally
relented to his requests for a meeting.  I invited him over and let him
seduce me - sucking him off for my first taste of cum and then letting him
lay me on my bed, spread my legs and ride me.  I still vividly remember the
feeling of my stocking covered legs wrapped around him, my nails digging
into his bare ass, and the sensation of his cock pulsing as he shot his
load deep in my ass.
      Unfortunately, since those two encounters I've had little time to
indulge my alternative wardrobe activities and have only managed to dress
up and go out a small number of times.  Grad school, work, and family
responsibilities kept me pretty busy. Then I met a woman named Rita - a
fiery raven haired Latina with medium brown skin, perfect 36C breasts, a
tiny waist, round full hips, shapely legs, and a full set of kissable lips.
Her hair is glossy and tumbles down in great curls past her shoulders and
she is rarely seen without perfect makeup, impeccable clothes, and 4 inch
heels.  We started dating and I knew beyond a shadow of a doubt that she
could be the one for me.  But before things went too far I needed to
confess my penchant for putting on a dress.  I was nervous, but she had
exhibited an open mind to erotic deviations - confessing her occasional
fondness for other women and a love of light bondage.  So I figured if
anyone would be accepting of a cross-dressing guy she would be.  Much to my
amazement and joy she was completely cool with the concept.
      We'd been dating for about a month when I owned up to my alternative
wardrobe activities.  After I confessed to her she smiled slyly and asked
if I had any pictures.  When I showed her the rather large collection of
images of myself in drag she was speechless.  She said I looked amazing.
She had expected to see "a guy in a dress" and not some tall blonde hottie
- adding that she was definitely jealous of my legs.  I was flattered and
stunned at her level of acceptance.  I guess her being "bi" helped.  She
quickly urged me to dress again for her sometime.  I didn't wait long.  A
couple of weeks later I got all dolled up and we went out - both in short
skirts and heels.  After leaving the bar we had a great time back at my
place.
      That was about a year ago.  Rita and I continued to date and rapidly
became a "couple".  But the demands of everyday life seemed to leave us
little time to explore any erotic adventures.  We managed to hit a "swing"
club a couple times and I even let her pick up another guy at a bar and
bring him home so she could have a mind blowing session of double
penetration.  But the opportunity for me to dress and play just didn't seem
to surface.
      Finally, as fall approached we decided that I should don a dress
again for Halloween - perhaps in some theme costume we could both enjoy.
After looking online for about a week we settled on a fun little combo of
the cop/prisoner combo.
      Finding an outfit for her was easy - a spandex prisoner costume dress
in bright orange with appropriate numbers stenciled on the front.  It was
short, coming to just below her crotch, made form fitting spandex to show
her curves, and low cut to allow ample cleavage.  She accessorized the
outfit with a wide leather corset belt, thigh high leather boots with four
inch heels, black fishnet thigh highs, and a black lace push up bra which
was clearly visible.
      My outfit was a bit more difficult to find.  I looked online at many
different "law enforcement" style outfits but none of them looked like they
would flatter my form.  They just didn't screamed "buy me!"  Finally I
found an outfit that would work.  It was a khaki colored "sheriff" mini
dress with short sleeves and a short pleated bottom which rode a good seven
inches above the knee.  I accessorized the dress with a wide black leather
belt with silver buckles, black knee high boots with three and a half inch
heels, requisite badge and patches, and of course a sturdy pair of
handcuffs.  For under the dress I chose a black lace bra, black lace cami
top, matching corset with six garters, tan stockings, black satin thong,
and a black lacy petticoat to fill out the pleated bottom of the dress.
      Halloween quickly came and we rented a suite that was near the bar we
were planning on visiting.  It was a nice set of rooms consisting of a
small kitchen area, living area with couch, chairs, and a fireplace.  It
had a large bathroom and a spacious separate bedroom with two queen
beds. We quickly got settled in, stocked the kitchen with some drinks and
snacks, and started to get ready.
      Rita's preparations were done in a short amount of time.  She has a
natural beauty so a bit of makeup, fluffing the hair, and donning her
outfit was done with relative speed.  That left her time to help me with my
preparations.
      My transformation from "average joe" to hot tranny is a bit time
consuming and it takes a full two hours to shave everything (and I mean
everything), apply makeup, don the blonde wig, and get dressed.  Rita
helped lace me into my black corset, assisted with my chest tape to make
convincing cleavage, and with snapping the garters onto stockings at the
back of my thighs.  Next, I pulled the satin thong on and tucked my cock
back between my legs before pulling the thong all the way on.
      For me the dressing process has a strong sensual aspect.  The smell
of the makeup, sound and feel of the lacy clothing, and most of all the
sensation of sliding silky stockings up my freshly shaven legs is an
incredible turn on.  I can't really say why - just that it is an amazing
feeling that I never tire of.
      The rest of the outfit went on quickly - bra with breast forms,
camisole, petticoat, and dress all slid into place with ease.  The final
step was pressing on the press on nails with a French manicure look.
      Once I was fully dressed I pulled on my high heeled boots, tossed a
few things into my small shoulder purse, and we were ready to go.  But
before we headed out, I naturally wanted a few pictures.  I, like many of
the cross-dressing clan, are true camera whores.  I love posing for
pictures while dressed so Rita snapped a dozen shots of me on the bed and
standing in front of the door.  Then I popped the camera into my purse and
we headed out the door.
      It was a short drive to the bar.  The parking lot was full but we
managed to find a place to park near the back.  As we exited the car and
started to head inside I snuck a furtive glance toward the dimly lit back
of the parking lot, remembering fondly and with some chagrin how not that
long ago in this same parking lot I had let a perfect stranger bend me over
the hood of his truck, push my skirt up around my waist, and pound his meat
up my ass.  I'd never told Rita about that little adventure and had decided
to keep that gem of a memory just for me.  Focusing once again, I
straighten my dress and we headed inside the bar.
      As expected the bar was packed with a variety of folks in all kinds
of costumes.  There were plenty of transgender folks and a good mix of gay
and straight - and the costumes were a smorgasbord for the visual senses.
Everything from complex lighted costumes to funny outfits to slutty attire
- it was amazingly fun to look at.
      Rita and I blended in and quickly made our way to the bar.  We were
lucky and found two unoccupied seats at bar and ordered drinks.  The music
was loud, but not so loud you couldn't talk.  As we chatted we marveled at
the range of costumes.  And while we talked I scanned the room for
potential playmates for the evening.  There were several attractive cross
dressers in attendance and I had a hankering to play with another like
myself.  As I ogled the crowd Rita downed her drink, grabbed my hand and
dragged me out to the dance floor.
      Dancing in drag is always fun.  The feel of the clothing while
getting lost in the pounding rhythm of the music adds to the feeling of
femininity.  While we danced I could glimpse myself in the mirrors
surrounding the dance floor.  When I looked at myself I could see a tall,
fit, sexy blonde dancing with a hot little Latina.  It was intoxicating.
And there's just something about wearing four inch heels that makes it easy
to shake your ass!  Rita was getting her share of attention - she looked
incredibly hot in her form fitting outfit and several times a random guy
would try to cut in on us or sneak a grope of her ass.  But she's well
versed in fending off unwanted attention and deftly maneuvered away from
the superfluous suitors.  We danced a few numbers and after some minor
protests I finally convinced Rita that I needed another drink.  She smiled
and nodded and I led her off the floor and out onto the bar's outside patio
to get some cool air and another cocktail.
      The bar at the outside patio was less busy than inside and we quickly
found a spot at a nearby table.  Rita went up to the bar to order drinks
and while she was gone I noticed a rather tall guy dressed like a baseball
player sitting at the next table checking me out.  When he realized that I
had caught him looking at me he quickly looked away, but when he glanced
back again I gave him a sly flirty smile and was rewarded with a smile in
return.  Just then Rita returned bearing a couple drinks.  As we chatted I
continued to catch Mr. Baseball looking over at me from his position behind
Rita.  I noticed that he was with a petite Asian woman.  She was pretty
with a round figure but not fat. She had black straight hair down to her
shoulders and was dressed in a French maid outfit with fishnets and black
patent spike heels.  As Rita and I chatted about random topics I furtively
watched my baseball playing fan and he continued to sneak glances my way.
I wasn't sure where this was going but I was rather intrigued at the
possibilities.  I decided to take things into hand, got up from the table
and told Rita to follow me.
      We walked up to Mr. Baseball and his hot little French Maid friend
and all I could manage to come up with was an incredibly lame, "Have I seen
you two here before?"  He looked rather taken aback but quickly recovered
and said it was their first time at that bar.  Rita quickly jumped in
complimenting the woman on her outfit and we all started exchanging
compliments all around.  We introduced ourselves and they quickly followed
suit - his name was Ken and his wife was named Amy.  They were both
professionals, had lived in the area for several years, and had been
married for about five years.  Within minutes the four of us were chatting
like old friends.
      As the night progressed we learned more about each other. Amy, like
Rita, was bi (and they definitely seemed to be hitting it off).  Ken
confessed he had some bi experiences in the past and was open to almost
anything.  After chatting for awhile we all got up and headed for the dance
floor.
      We started out in typical couple fashion with me dancing with Rita
and Ken dancing with Amy.  Before long Rita and Amy started dancing with
each other and as the drinks flowed the two of them began to get closer and
closer to each other on the dance floor, running their hands over each
other and grinding into one another. Needless to say it was an unbelievably
hot show that they were putting on.  As they danced Ken moved out of the
way, stood awkwardly for a moment, and then he started dancing with me.  He
had a goofy look - sort of embarrassed - when he started to dance with me.
At one point I leaned in close and asked him if he liked how I looked.
"You look very hot!" he replied in a breathy whisper.
      The girls continued to dance together, lost in their own sexual
tension and oblivious to the rest of the world for the moment.  Ken and I
continued to dance together exchanging looks and occasionally brushing up
against each other.  At one point I leaned in close, put my face in towards
his neck, and slowly breathed warm air along his throat. As I did this I
felt him tense slightly and noticed what was obviously a growing erection
move against my thigh.  As we continued to dance he moved in closer and I
felt him press more of his crotch against me. Slowly turning, I wrapped his
arms around me and pressed my bottom against his crotch and let him slowly
grind his hard cock against my ass. Feeling a flush of sexual excitement I
turned back to him and suggested we move to the bar for another drink.
      As we sat next to each other we watched our women continue to dance
and grind with each other.  I looked over at him and with a smile I said,
"Looks like the girls have their evening planned...so what do you think we
should do?"
      He gave me a quick smile and I felt his hand move on my thigh under
the bar.  His hand slid up my stocking covered leg and under my dress as he
replied, "I think we'll find something to do."  I smiled back and suggested
we head back to our hotel.
      We finished our drinks and headed out to the dance floor to get the
girls.  We got no argument from them. We left the bar and Rita and I piled
into our car and Ken and Amy followed in theirs.
      Once we got back to the suite I quickly lit a few candles that we had
brought and placed around the room.  Rita offered up some drinks.  I wasn't
sure where all this was going next - but there was no need for me to worry.
Rita, not being one to waste time, grabbed Amy by the hand and led her into
the bedroom.  They stopped at the edge of the bed and started kissing each
other with surprising zeal.  They held each other, hands roaming over each
other's bodies with an intensity born of their building passion.  Rita,
being a bit dominant, pushed Amy onto the bed. Amy kicked off her heels and
Rita pulled off her own thigh high leather boots and climbed onto the bed
with Amy where the two of them started to kiss and fondle each other.
      Ken and I were stunned into silence and inaction.  I knew Rita was bi
but had never seen her with another woman before.  I glanced at Ken and he
just grinned, watching the show the two women were putting on for us.  I
looked back toward the bed and Rita had pushed Amy's skirt up, pulled her
thong to the side, and was beginning to slurp noisily at her neatly trimmed
pussy.  Amy moaned loudly and arched her back.  I immediately felt my cock
start to strain at the front of my own panties.  The sights and sounds were
surreal.  Two incredibly beautiful woman were going down on each other like
there was no tomorrow.  My first thought was to climb up behind Rita, push
her dress up and plunge my cock into her.  I trembled in my high heeled
boots slightly at the thought.  But before I could react Ken placed a hand
on my shoulder and turned me to face him.  He bent toward me, circled his
arms around my waist, and started to kiss me.
      Again, I don't consider myself to be gay or even bi, but there is
something that happens when I wear a dress.  So after a fleeting moment of
resistance I opened my mouth and let him kiss me fully.  As he held me I
could feel his hand play across my back and down to my ass.  One hand
slipped deftly under my skirt and started to massage my ass and tugged on
my garter strap.
      We broke the kiss and I looked over to see if Rita had noticed.  She
was oblivious - gone now in her own world of pleasure as she and Amy
continued to lick and suck and finger each other.  Their clothing was
slowly being peeled away and now they were both clad only in bras and
stockings.  The site was entrancing and erotic, and as much as I wanted to
stay and watch I had some needs of my own that demanded filling.  I took
Ken by the hand and led him into the living area of the suite.
      My new friend didn't waste any time.  He quickly stripped off his
shirt, shoes, and pants and stood before me in nothing but his boxers.  His
cock - which measured something around six inches - stuck out noticeably
from the front.  I moved toward him intent on dropping to my knees to suck
him off but he seemed to have other ideas.  Before I could move he stepped
toward me, dropped to his knees, and pushed my dress and petticoats up.
With a quick motion he jerked my thong to the side and released my stiff
prick from its satin prison.  Then he leaned in and took me fully into his
mouth.
      I leaned back against a chair as his warm mouth engulfed me.  It felt
so good I almost shot a load right there.  I gasped as his tongue circled
the head and he slid down along the shaft until I could feel his tonsils
pushing against my swollen head. I lifted my dress up a bit more so I could
watch him sucking my cock. His warm mouth and quick tongue movements felt
unbelievable and as he slowly slurped and sucked he moved his hands up and
down my stocking covered legs, occasionally stopping on my ass under my
skirt.  As he sucked he slowly started fingering my ass and then used his
other hand to stroke and fondle my smooth shaved balls.
      I looked down to watch and visually take in the moment.  I saw his
head bobbing slowly on my stiff cock, his face disappearing under my
bunched up dress, the tops of my garters holding up my stockings, my legs
spread wide with high heeled boots planted on either side of his kneeling
figure.  I was almost overwhelmed with the sexual environment - the soft
candle light, the feel of his hands roaming on my stocking covered legs and
exploring my ass, the sounds of the girls in the next room moaning in their
own self contained world of pleasure.  All of this combined to bring me to
a quick and amazingly powerful climax.  I gripped the chair and cried out
as I shot my load into his greedy mouth.  He slurped it all - not spilling
a drop. The intensity of my orgasm left me weak and slightly dizzy and I
almost slumped to the floor.  Before my head cleared from the intensity of
the orgasm Ken stood up and wrapped his arms about me and drew me in for a
kiss.  Our tongues met again and I could taste my own seed. The texture of
his lips and tongue mingled with my cum was an incredible turn on and my
softening cock twitched again in growing excitement.
      The sounds from the next room were growing in volume and intensity
and I moved on wobbly legs to take a peek into the bedroom.  The girls were
lying side by side in a slow sensual sixty nine, each licking the other
with languid movements.  The air was thick with the smell of their sex and
they moaned and cooed softly as they continued to pleasure each other.
Again I was filled with an urge to climb up onto the bed and join in.  But
once again Ken, who had joined me in the doorway to watch, had other ideas.
      He gently placed a hand on my shoulder and turned me to face him.  We
kissed again and he fumbled to unbutton my khaki costume dress.  I helped
him along with his quest by undoing the belt and shrugging out of the
outfit.  He stepped back and looked me up and down again as I stood before
him in my bra, camisole, petticoat, garter, stockings and boots.  He moved
forward again and wrapped his arms around me for another kiss.  As our
mouths met and tongues intertwined I felt him exploring my body.  His hands
moved down to my waist and then up and under my petticoat.  He then
proceeded to tug on my thong - pulling it down toward my knees with a swift
strong tug.  I got the hint, stepping away briefly to slide the panties
down to the floor where I stepped quickly out of them and moved toward
small table in the suite where various bottles were sitting including a
rather conspicuous container of lube.
      Ken came up behind me, lifted my petticoat slip, and pressed himself
against my back.  I could feel his throbbing meat against the crack of my
ass.  He took me by the shoulder again, turned me around, and pushed me
back until I was sitting on the table edge.  He then lifted my legs until I
had to lean back and balance myself with my hands on the top of the table.
He gently grasped each leg and unzipped and removed my high heeled boots in
turn.  Then I watched as he poured lube onto his fingers and stiff cock.
He lifted my legs higher and placed my ankles onto his shoulders and I had
to surrender my position and lay down on top of the table.  He then started
working his fingers into my ass.  First one and then two of his digits
moved quickly and smoothly into my tight hole and I trembled at the intense
sensation.  After a few moments of this he moved forward slightly and
positioned his cock to enter me.
      Now in the past I had always required my male paramours to sheath
themselves in protection.  But the heat of the moment (probably combined
with the copious amount of alcohol I had consumed) pushed the thought from
my mind.  All I wanted at that moment was to feel his stiff cock deep
inside me.  He was more than willing to oblige.
      He entered me slowly, my legs raised high, ankles on his shoulders,
and his hands on my hips and he pulled me toward him.  I gripped the edge
of the table hard as he started to slide in and out of my tight ass.  There
was a bit of pain this time but it quickly passed leaving a feeling of
fullness and excitement.  I looked up to see him standing before me.  His
face, framed by my stocking covered feet resting on his shoulders, intense
in concentration and excitement. His strokes were slow and steady - pulling
almost all of the way out before plunging back inside me. It felt
incredible.
      After a few minutes he paused and reached over for the lube bottle
again.  Then, after pouring another copious amount into his palm, he
started stroking my reawakened cock with his right hand while he continued
to slide his meat into me.  A few seconds after he started this the sounds
from the next room picked up in intensity as Rita, who I recognized by her
voice, had what must have been an earth shattering orgasm as she cried out
in sheer erotic delight.  This, combined with Ken's manual manipulation and
anal plundering, pushed me over the edge again into an intense wave of
orgasmic bliss.  I gripped the table and shouted as I shot my load for the
second time that night - a jet of hot sticky cum shooting into the air and
landing on my petticoats and stocking tops.
      Ken, much to my surprise and enjoyment, was still going strong.  He
slid his cock out of me and pulled me up into a sitting position.  He then
led me over to the center of the room and told me to get down on my hands
and knees.  Being a people pleaser at heart I quickly acquiesced to request
and assumed the doggie position.
      Ken knelt behind me and soon had his cock buried in my ass again.  He
kept up his slow and steady pace, sliding in and out with a regular rhythm.
His hands grasped my hips and he fucked me long and hard, occasionally
shifting position to grab the garter straps that ran down my ass and tug
when he pulled me toward him.  After a few minutes of this he picked up his
pace and I could sense that he was getting ready to cum.  He moved faster,
sliding deep into my ass.  Then with a cry he pulled me hard toward him,
burying his cock deep in my ass and holding me there as he came.  I felt
warmth deep inside me as he shot his load.  His hands held my hips tightly
and he continued to hold my against him as his orgasm passed.  Sweating
exhausted, and happy, we both collapsed into a heap on the floor.
      When I finally started to emerge from my post sex glow I slowly
untangled myself from Ken and got up from the floor.  The room was quiet
and I peeked in through the bedroom door to see both Rita and Amy passed
out on the bed, still tangled in each other's arms and sleeping with the
peace that only comes after intense sexual pleasure. As I stood there
admiring their beauty I noticed an unfamiliar sensation as Ken's seed
leaked out of my ass and ran down the back of my thigh.  I smiled at the
feeling and looked back into the living area of the suite where Ken was
rousing himself from the floor. He saw me and smiled back as he moved into
the kitchen area to get a drink.
      I plopped down on the couch, my clothing disheveled, a run in my
stocking, and my makeup a mess.  Ken joined me on the couch a few moments
later he offered me a beer from the fridge. We both sat and chatted a bit
like two old friends, talking about how hot it was to watch the girls and
how we would all have to get together again soon.  I asked him how long
he'd been into t-girls and he told me a few years. I asked if he dressed
and he told me no. He asked how long I'd been dressing and I told him about
how I'd started seriously doing it a few years before - but didn't get to
do it as often as I would like.  As we sat there drinking our beers and
chatting I noticed breaks in the conversation and that Ken's eyes were
starting to droop.  It wasn't long until he started to drift off to sleep.
Figuring we were done for the night I got quietly up from the couch,
crawled onto the second bed in the bedroom, and soon fell into an exhausted
but happy sleep.
      When I awoke in the morning Ken and Amy were gone, having slipped out
sometime during the night. As I stretched and yawned, sore from wearing a
corset all night, I looked over at Rita who was starting to wake up
herself.  As we talked a bit I asked her how she had enjoyed the evening.
With a sheepish grin she said he had a good time.  She admitted that much
of the evening from the time we left the bar was a bit of a blur, but she
remembered some intense orgasms due to the talent of Amy's tongue.  Then,
with a puzzled look, she asked me what Ken and I had done while she and Amy
had played.  I paused for a moment, glancing out the door of the bedroom
into the living area of the suite where I could see my satin panties
crumpled up on the floor where I had left them.  Then, I simply smiled and
answered "Not much.  We just watched."