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Date: Fri, 09 Aug 2002 12:54:20 -0400
From: John Clark <jcwaim@hotmail.com>
Subject: My Secret TS Wish
I have always known that I had different urges than other males my age.
When I was a teen, my best orgasms always came when I was wearing my
sister's silky panties, bra, and nylons, and ramming whatever object I could
find up my horny ass. I was especially excited by the transexuals in the
tabloid magazines, and often fantasized about what it would be like to have
sex with one.
Here it is, now many years later, happily married and a decent enough sex
life. Some of my most powerful orgasms are still "solo" though, and happen
while I'm dressed in black silky control top pantyhose, with a buttplug
buried in my ass and a dildo in my mouth. My favorite position is kneeling
in front of our computer, while looking at images of a shemale being sucked,
and then ass-fucking a kneeling submissive male. I imagine myself
submitting to my TS's desires, and being thoroughly fucked by her. A few
minutes of good dildo sucking and ass-reaming and I'm blowing a big load in
my hand. Sometimes I also imagine I'm the very womanly TS, having my way
with a formerly straight male, blowing my load up his tight, willing ass.
Which brings me back to the present. I have frequent fantasies about a
chance encounter with a TS while on an out of town trip. It usually goes
something like this...
It's been awhile, but here I am back in Oklahoma City on an extended
business trip. Had to fly in on a Friday, but don't have anything going on
until Monday morning. I check into the Residence Inn, and unpack my things
for my stay. As usual I've packed some of my special clothes and my "toys"
to help relieve the "tension" while I'm on the road. I did some afternoon
shopping to stock up the fridge and relaxed in the apartment until dinner.
After a nice steak at the Outback I decided to head out for a few drinks and
shoot some pool. Went back and took a quick shower to get the road grime
off, and decided to be daring tonight and wear some of my accessories for my
evening out.
I got out a pair of nude, crotchless pantyhose and slid them up my legs
slowly, savoring the feel of the silkiness against my legs. I then took out
my buttplug and greased it up thoroughly and slowly teased it past my tight
sphincter. I didn't seat it right away, but slowly worked it in and out of
my hole, getting used to the sensation. When I was thoroughly loosened up,
I pushed it in the last couple of inches and it popped in, seating 5" of
rubber cock in my ass. I squirmed around, making the plug move around and
stimulate all the right places. I then pulled out my favorite pair of black
silky panties and eased them up my legs, and tucked my hardening cock into
the glorious fabric. I then strutted around the apartment and checked out
my reflection in the mirror, excited at the prospect of going out in my
hidden finery. I finished dressing in some comfortable Levi's and a sport
shirt, with socks and shoes to hide my nylon clad feet. I then set out for
an evening of fun.
During the drive I continually adjusted myself in the driver's seat,
stirring around the plug around in my horny ass. I was already thinking
about how good it would feel when I got back to the apartment and would jack
off a big load. I had already decided to get out my 9" dildo and give
myself a good reaming when I got back. For now though, I picked a small
local bar, which I knew to be fairly dark and intimate for my evening's
drinking. I checked the buttplug one last time before heading in, then took
a set at a remote corner of the bar where I could watch everyone.
I had three bourbon and cokes before I got up the nerve to put 50 cents onto
the pool table. It was a slow night due to a Sooners home game, so my game
came up quickly. I wasn't paying attention to the table, and was startled
when a good looking woman came up to me asked me if I wanted to play. I
quickly regained my composure and followed her to the pool table. While I
was racking the balls I had a chance to look her over a little more closely,
and was impressed with what I saw. She had to be mid thirties, about 5' 8",
shoulder length auburn hair, and the prettiest green eyes I had ever seen.
She had nicely shaped boobs that peeked out of her low-cut top, a very sexy
ass, and a body that was very trim and well proportioned. Her deep tan and
gold jewelry completed the package. I was already forming a mental image
of stripping her down to her own panties and hose, and rubbing my body
against hers. I had to readjust my cock before I straightened up, as it was
straining against the silky fabric.
I introduced myself to my opponent and she told me her name was Shawna. I
was surprised when she asked if I wanted to play for anything. Being a
fairly competent pool shooter, I agreed to play for a drink. Shawna broke
the rack well, sending the balls scattering over the table. The game was
close, but I ended up sinking the eight ball after she missed. She ordered
us both another drink while I waited for the next player to challenge the
table. Shawna and I talked for a couple of minutes, during which I found
she was currently unattached. When no one else showed up to challenge the
table, Shawna asked if I'd like to play another one. We again played a
close one, with Shawna running her last two balls and then the eight. I
bought her a margarita and another bourbon and coke for myself.
We sat and drank and talked for awhile until suddenly she jumps up and grabs
my hand and leads me to the small dance floor, "this is my favorite song"
she squeals. We dance slowly, not too close at first, then gradually our
hands start to roam over each others' bodies, and our tongues explore each
others' mouth. In a moment of panic I feel Shawn's fingers probe my
asscheeks and nudge against the probe buried between them. I start to push
away from her but she holds me tight and says "don't worry baby, I really
enjoy having my butt filled sometimes, it's not a problem with me". I look
at her closely and decide "what the hell", she already knows and it doesn't
bother her. So I relax back into her arms and we continue fondling each
other as we dance. She definitely enjoys wiggling the probe around in my
butt causing my dick to swell in its silken prison. We finish our dance and
head back to the bar, holding hands as we walk.
Shawna orders us both a shooter of Cuervo Gold and we both down them
quickly. By now I'm pretty hammered, and really into kissing and fondling
Shawna's body. She looks at me coyly and asks if I'd like to play one more
game of pool for different stakes. I am definitely interested and ask her
what the terms are. "If you win, I'll give you the best blowjob of your
life, and if I win, you have to let me ream you out good". I couldn't see a
losing side to this proposition so I quickly agreed to her terms. This game
turned out to be no contest. I let Shawna break and watched as she ran the
table out on me. I smiled at the implications of my loss, thinking how much
of a turn on it would be to have Shawna playing with my ass.
As we sat back down she handed me two little blue pills and took two
herself. "What are these" I asked suspiciously, and was surprised when she
replied "Viagra, great for an all night hardon and it even helps the female
libido". I immediately popped them in my mouth and took a chug from my
drink. I was amazed at my good fortune this evening, and could only imagine
the awesome sex that was waiting for us.
As the Viagra started taking effect I started noticing blue halos around the
bar lights. I asked Shawna about this and she told me it was a good way to
tell that the drug was taking effect. That and the rock hard boner she was
stroking through my jeans and panties. We finished our drinks and headed
for the door, with Shawna playing with the buttplug as we walked. "We'll go
back to your place if that's okay with you" she asked, which I quickly
agreed to. She followed me back in her car and we quickly made it up to my
apartment.
"Remember our bet" she said with a smile and asked me to strip for her. I
hesitated briefly but then thought "what the hell, she already knows and is
cool with it" so I kicked off my shoes, peeled off my socks, and pulled off
my jeans and shirt. I stood in front of her and blushed and she told me
"you have such a nice butt, I can see why it really turns you on to have
something in it". With that she drew me to her and we kissed very
passionately while she worked the rubber cock around in my ass and caressed
my steely rod. I was so turned on I almost came on the spot. "I usually
like to use a dildo on my ass when I'm really horny" she smiled, "you
wouldn't happen to have one of those handy would you?" she asked. My
immediate blush gave her all of the answer she needed. I reached into the
bottom of my drawer and pulled out the stiff 9" dildo and showed it to her.
"I have one just like it at home" she laughed, putting me at ease.
Shawna took the dildo from my hand and slowly worked it around in her mouth,
until she was ultimately taking the whole thing down her throat. She
removed it sensuously, licking it repeatedly before placing the tip against
my lips. "Show me how you suck on it" she said, "I know you've done it
before". I eased my mouth onto it and started bobbing up and down on it,
trying to imitate what Shawna had done. She started ramming the dildo into
my mouth while working the buttplug furiously around in my ass. I had never
been as hard or turned on before in my life as with Shawna. I was humping
back against the plug and plunging my head as far as I could onto the dildo.
I was delirious with pleasure and very close to cumming. Shawna slowed
things down and told me I had earned the best blowjob in the world even
though I had lost the pool game.
Shawn told me to take off my panties, which I immediately did, and was
surprised, when she popped out the buttplug and pushed me back on to the
bed. "You need something bigger in there" she smiled and pushed my legs up
and slowly started working the big dildo into my already stretched ass. I
pulled my legs back toward my chest to give her better access to my chute,
and she definitely knew what to do. She purposefully slid the whole length
in, twisting and making me writhe with pleasure. Once she had it seated
firmly she took hold of my rigid cock and started working her magic on it.
Her tongue danced over the head of my cock, which was already straining from
the Viagra and her extremely pleasurable action in my rear. Her mouth
slowly descended the length of my shaft, while her tongue massaged the
sensitive underside. She began to pump the dildo in and out of my ass very
deliberately, while bobbing her head up and down, taking my whole length
down her throat.
The pleasure I felt was indescribable. Shawna had me so turned on I knew it
was going to be the best orgasm of my life. Sensing my impending climax,
she started jacking me real hard, while ramming the dildo in as far as it
would go. "Give it to me baby" she commanded and I responded immediately.
The cum seemed to start in the depths of my ass, coursing up through my
straining cock, and exploded into her warm waiting mouth. I was moaning
loudly as the jism boiled out of my body, gush after gush of love juice, all
greedily lapped up by Shawna.
She smiled at the intensity of my experience, and moved her body alongside
me on the bed. She placed her hands on either side of my head and locked me
in a passionate kiss. I realized with a start that she had kept most of my
huge load in her mouth, and was now forcing it into mine. I struggled
briefly, but she maintained her grip and continued passing my slimy ooze
onto my now curious tongue. I had tasted a little of my own come before,
but this time I was being forced to take a whole load. The taste was
somewhat salty, with a slightly bitter aftertaste. Not gourmet fare, but
definitely not the worst thing I had ever tasted. When she had emptied the
contents of her mouth into mine, she drew back and stared into my eyes "was
it everything I promised?" she asked with a grin. ""That is the most
intense orgasm I have ever had in my life" I exclaimed, still trying to
catch my breath from the very pleasurable workout. "Remember our bet
though" she replied impishly, "now you have to do what I want!" My cock
spasmed at the thought of what else she had planned for me.
Shawna stood up from the bed and slowly started to undress, first removing
her top, and revealing very nice breasts, barely contained by a black
see-through bra. She then slid her form fitting jeans down, revealing a
pair of black slimming panties, much like a pair I had. "First I want you
to worship my breasts" she revealed, and unhooked her bra and let it drop to
the floor. I sat up on the edge of the bed, and she immediately thrust her
horny nipples at my face. My tongue traced circles around each nipple,
teasing each to rock hard firmness. I massaged and kneaded each breast,
causing Shawna to moan with delight. I was pleased to know she was really
getting off on my tonguing. "You need to move that mouth lower" Shawna
moaned lustily", and reached down to slip off her panties and show me my
treat.
As I moved in towards her mound I was startled by the sudden appearance of a
very swollen and purple cock staring me in the face. "You don't know how
good it feels to finally let it free" Shawna said suddenly and grabbed my
head before I could react. She rammed her cock into my startled face and
pushed me back on the bed, straddling my chest and forcing her cock deeper
into my mouth. I struggled to repel the invader but her grip was strong,
and her thighs had my arms pinned to the bed. "Come on baby, you know you
really wanted this" Shawna said teasingly as she worked her very large cock
in and out of my mouth. "If you do a good job I'll even let you taste my
come" she said with a laugh as she pounded away at my face.
Having overcome my initial shock, and somewhat inebriated state, my mind
struggled to comprehend what was happening to me. I obviously had a very
large cock pumping in and out of my mouth, and it was attached to what was
otherwise a very beautiful woman. My mind struggled with how to deal with
this situation, but it was my "other" head that ultimately made the decision
for us. My somewhat deflating cock had sprung to life and was throbbing
almost painfully while my face was being fucked. This same fact had not
escaped Shawna, and she reached down and grabbed hold of my steely rod.
"That's it baby, get with the program, you know you've wanted this for a
long time", she observed quite correctly. With the matter finally settled,
I decided to make the best of an unusual situation.
I had practiced giving head to my dildo many times but this was my first
attempt on the real thing. I tightened my mouth into a ring around her cock
and moved my tongue around the glans underneath, stimulating her in the same
way she had just brought me such pleasure. Shawna eased up off the bed
allowing me to slide my arms out and wrap them around her waist, pulling her
hips and cock closer to my face. She immediately responded to my change in
attitude by stroking my cock harder, increasing the urgency of my sucking.
"Here baby, work this into my ass" Shawna said, handing me the big dildo
that until recently had been buried in my own chute. She must have greased
her ass up earlier, because the dildo slipped in without resistance, until
almost the full length was buried in her. "OOOOOH YEAH!!" Shawna moaned as
she increased the vigor of her mouth fucking, causing my throat to stretch
and accept the very head of her cock. "Oh fuck that feels good!" Shawna
exclaimed as I hoped I was giving as good a blowjob as I had received only a
short time ago.
I worked the dildo around mercilessly in her ass, making her squirm and pump
my face with wild abandon. "Get ready baby" she moaned, "you're about to
receive your reward for being such a good cocksucker". With that
encouragement, I plunged the dildo as deep as I could, and suctioned her
cock as deep as I could down my throat. A deep guttural moan escaped her
lips as I felt her swell menacingly in my mouth and the first shot of a very
large load gushed into my waiting mouth. Shawna pounded my face brutally as
she pumped what seemed like gallons of come into my already full mouth.
Each successive spurt bubbled out down my chin and onto my chest where it
pooled in globs. I gasped at the volume of come I was swallowing, and the
amount that I just could not gulp down.
Shawna fucked my face for what seemed like hours, as her body drained it's
love juice into my face and down onto my chest. Shawna gave one final gasp
and collapsed down onto my body, with her cock slipping out with an audible
pop as her come drooled out of my thoroughly fucked mouth. "Oh yeah baby!"
she sighed, "it's been a long time since I had a blowjob that good, you may
have just earned the right to experience a good ass-fucking tonight". I
squirmed under her, anticipating what I knew would be a very new and
exciting experience for me.
Shawna made me clean up all of the come smeared all over our bodies, either
by licking it off of her, or scooping it up with her fingers and feeding it
to my lips. "That's it baby, get us all nice and clean so we can have even
more fun!" she playfully said as I finished cleaning up the last of her
voluminous load. Shawna slid the dildo out of her ass and grinned at me "we
better get you loosened back up for your initiation" she smiled, as I noted
her own cock favorably compared with the dimensions of my favorite toy.
The Viagra was continuing its effect, as both of us were rock hard, even
after our intense orgasms. My cock twitched as Shawna worked the dildo in
and out of my already greasy hole, while her other hand stroked slowly up
and down my manhood. The feeling was utterly incredible, especially with
the knowledge that her "womanhood" would be replacing the imitation cock now
filling my ass. "Ooh, you're good and loose now" Shawna cooed, "I'll bet
you can't wait for me to fuck your virgin ass". She had me nailed both
figuratively and for real.
I reached up and began stroking her throbbing cock, knowing it would soon
fill the need in my horny ass. "That's it baby, get it good and hard for
your ass" she encouraged, as she continued plunging the dildo deeply into
me. "I want you on your knees when I shoot my load into you" she explained,
"but first I want you on your back so I can watch your face when I pop your
cherry" she ordered. She suddenly popped the dildo out of me, threw it on
the bed, and positioned her body between my thighs, with her cock pointing
menacingly at my gaping hole. "Get ready baby, here it comes" she cooed as
she eased herself into my comfortably stretched ass. There wasn't any pain
as the head popped past my sphincter, the good reaming I had already
received made sure of that. Then her length thoroughly filled me as she
seated her cock deeply in my gut.
Shawna stared intently at me, her eyes peering deeply into my soul. "I wish
you could see yourself right now" she said seriously, "the look on your face
is one of pure joy". It was then I knew what I had been missing all of
those years, denying what was truly a part of me, hiding it away and
ignoring it's existence. With that realization, I began to really enjoy
what I was experiencing, grinding my ass back against Shawna's cock, driving
it as deep as possible into me. Shawna grunted pleasurably as my ass gripped
her cock and squeezed it as she pumped it in and out of me. "Put your legs
up over my shoulders" Shawna moaned as she continued pounding deep into me.
Rolling my hips back seemed to open me up even more as her cock explored
ever deeper into me. She crushed her body down on mine, mashing her tits
into my chest and dove her tongue deep into my mouth.
The feeling was almost overwhelming, my cock was iron hard, rubbing between
our sweaty bodies as she continued my initiation into womanhood. My hands
were all over her body, twisting her nipples, squeezing her ass cheeks, and
pulling her deeply into me. Shawna humped me like this for close to a
half-hour, easing off each time she got close to cumming. "It's about time
you experienced your first load up your ass" Shawna commanded, "get on your
knees so I can really fuck you!". With that she popped her dick out, and I
quickly rolled over to comply and allow her to fill my emptiness.
I was now kneeling face down on my bed, my ass filled to the brim with her
cock, when she wiped off the dildo on the sheets and handed it to me.
"It'll feel even better if both holes are filled" she urged as she continued
filling my ass with her hot cock. The dildo tasted funky, but I eagerly
sucked it in, imitating the technique I had used earlier to coax a huge load
from her. My other hand sneaked down to my own throbbing cock and began
stroking it quickly. "That's it baby , suck it!" Shawna urged as her
pounding increased in intensity. Each thrust of her hips drove me down on
the imitation manhood, making me feel as if I was being fucked by two cocks
at once. Shawna was rapidly approaching orgasm as I felt her cock grow to
ever larger dimensions. "Stroke your little clitty" Shawna urged as I
pounded my own cock as hard as I could in time to her plunging deep into my
ass.
Shawna had me to the edge of reality, I was no longer in control of myself,
it was not my voice telling her "fuck my ass mistress, fill me with your
cock, come in my ass!" Not that she needed any encouragement, but it had
the desired effect. She was slamming me hard with each thrust, driving her
cock deeper than I could believe possible. . With a strained groan, Shawna
began pumping her hot seed deep into me. The first hot blast triggered a
response from my overstimulated prostate, and my come boiled out with such
heat and force I thought I would surely pass out. Each shot from Shawna
brought forth a new surge from my own cock, as if her come was passing
directly through me.
We both climaxed continuously for what seemed like several minutes, as my
ass milked every last drop from her, and my hand coaxed every last drop of
come from my body. We both must have actually passed out, as the next thing
I remember is waking up flat on the bed, Shawna sprawled across my back, and
her still firm cock planted solidly in my ass. It was a good thing as I
could feel the huge load of jism filling me and dribbling down my ass
cheeks. Shawna moaned into my back and spoke between deep breaths "that was
one of the most intense orgasms of my life" she wheezed still out of breath.
I could only groan in agreement, as my own breath was coming in gasps.
Once we had both recovered sufficiently, Shawna rolled over and smiled
mischievously at me, "I'm not finished with you yet baby" as she reached for
my painfully erect cock. "I need a good fucking tonight too, and you have
the right tool for the job." With that she rolled me onto my back and
positioned herself over me. She squatted slowly, easing my cock into her
ass inch by inch until she was fully impaled on me. Next she picked up the
lonely dildo, and plugged the gushing torrent from my hole. She then began
a slow up and down motion, while fondling her breasts very sensuously. My
hand found her cock and began stroking up and down, squeezing her balls, and
pinching her piss slit, making her increase her tempo on my cock. She
responded by working the dildo ever deeper into my thoroughly stretched ass.
It was truly an incredible sight, her incredible femininity bouncing up and
down on me, her fingers roaming her nipples, and her 8" cock pointed
directly at my face. "Cmon baby hit my mouth" I playfully teased as she
groaned and squeezed my cock tightly in her chute. I could only groan in
reply as my load worked it's way from deep inside me. We were deeply in
tune as her cock began to pulsate menacingly, my own cock getting ready to
deposit it's own load. It was as if we both climaxed as one, our cocks
spurting hot juice together, with mine spurting into her guts, and hers not
surprisingly landing on my outstretched tongue. "Give me all of your come
baby, right on my face" I urged her, as my own boiled up out of my body and
filled her to overflowing. My come was running down her thighs and onto the
bed, while hers landed on my hair, face, tongue, and chest. I could not
believe the amount of come she was able to produce, even after her very
large load earlier. I greedily licked up all I could find, and milked the
remainder out of her, causing her to moan and shudder.
Shawna sprawled across me, our tongues intertwined as we enjoyed the
afterglow of our experience. While the Viagra had worked for quite awhile,
its effect was beginning to finally diminish, allowing my cock to soften up.
With a pop it pulled free from her and immediately my warm come began
gushing out of her gaping ass. I caught as much as I could and rubbed it
all over her ass, making it sticky with my juice. Shawna laughed playfully
and told me "you know you're going to have clean that up don't you?" I
smiled and told her "with pleasure ma'am".
We laid in bed and talked for awhile, and Shawna told me of her
transformation, and her problems with finding open-minded men in Oklahoma.
"My last boyfriend didn't mind fucking me" she explained, but would never
suck her cock or allow himself to be fucked. I held my breath for what I
hoped was next, "would you be my boyfriend?" Shawna asked tentatively,
making my heart leap with joy. "I don't know what it is, but I feel so
wonderful with you". I could only reply in kind, "Shawna, you have opened a
whole new world to me, and I sure don't intend to turn my back on it now!" I
replied, finally accepting what I knew to be true my whole life. "I'd be
proud to have you as my girlfriend and make all of the other guys jealous!".
Shawna and I embraced passionately, tears streaking down our faces as we
held each other for a long time. "Why don't you pack your things?" Shawna
told me, "I have a very large house with plenty of room. "And don't forget
your special clothes and your toys" she added coyly. I could see that I was
in for the experience of my life, and I knew I was finally ready for it...