Jillian

Credit: https://www.nifty.org/nifty/transgender/she-male/jillian by Jillian

This is all true, something that happened last week. Names and minor
details have been changed to protect the guilty.


I'm certainly no angel, and working girls have been a guilty pleasure of
mine for all of my adult life. I also have a passion for TVs, CDs, and
shemales, but I've usually lived in places they're not readily available.
My first TV hookup was many years ago in San Francisco. One night in St.
Louis I picked up a couple of streetwalkers, and I was overjoyed to find
that one of them was a TV. I fucked them both before the night was out.


For the past ten years I've been unable to hook up for one reason or
another. I keep track of who and what is available locally on one of the
escort websites. There's one T-girl who's attracted my attention. I've
watched as she's grown from a twink CD into a full-fledged shemale, and
been interested, but never made a date for one reason or another. My
desire comes and goes, and she was just never available when I was in the
mood. We'll call her Jillian. She doesn't advertise very often. She
prefers a regular clientele, and only goes looking for more when she
needs to add to that list.


Jillian is now about 30. She has long black hair and green eyes. She's
not slender, more what you would describe as curvy, without being
anywhere near BBW territory. You can tell a lot about an escort from the
pictures and what's expressed between the lines of an ad, and she seemed
like a pleasant and relatively sane individual. I've been feeling a
little lonely lately, and I finally decided I was going to make an effort
to meet her. I wanted a weekday daytime date. I'm retired, and available,
and I didn't want a rush visit during her peak hours -- drive time and
weekends.


The first time I texted her number, I introduced myself and said I had
been seeing her ads for some time, but although we'd talked once or twice
we'd never met. I asked if she was available that day. After about a half
hour she replied, saying she was spending the day with friends, but would
be available the next few days. Unfortunately I was busy with one thing
and another, so we put it off to the following week. That following week
something similar happened, but we did spend some time texting back and
forth, and I got a better idea of the girl. Smart and funny are things I
like, and she was both. We finally chatted on Friday, and made an
afternoon appointment for the following Monday.


I spent the weekend in a state of raw excitement, viewing shemale videos
online, reading shemale porn, looking forward to a great adventure but
trying not to get my hopes up too high. Would she look as good as her
photos? Would she be into the pleasure, or just bored and wanting the
bucks? Sometimes it's dangerous to try to live a fantasy. I spent some
time that morning cleaning up -- shower, shave (face and genitals) and
multiple enemas to completely clean the inside.


She




Date a Transsexual



 texted me about 10 a.m. to make sure we were still on, and I replied
enthusiastically. She said that she thought we'd really enjoy ourselves.
She had sent me the address, and I'd checked it out in Google maps -- It
was a little clapboard 1-story in an area of old millworker housing, not
a mansion, but it appeared to be reasonably well-kept. I let her know
when I was on my way, and she said she'd be ready for me. I found it
easily, and parked on the street a few houses down so as not to be too
conspicuous.


I walked up on the front porch and knocked in the door. There was no
immediate response, but then I heard a dog barking. A few seconds later a
feminine voice laughed and said, "Just a minute, let me take care of the
dog." "Okay," I responded, and it grew quiet again. I guess the dog
went to the back yard, because I never heard or saw it again.


A minute later the door opened, and I was pleased with what I found
there. She had a big smile, even, white teeth, understated but well-done
makeup, and the long black hair I'd seen in the pictures was clean and
well-brushed. She was wearing a red and black corset, black lace bra and
panties, and heels that made her slightly taller than my 5'7". She
invited me in and we stepped into a living room full of eclectic
decoration, cluttered but not messy or dirty. We were only there a minute
or so before she led me to her bedroom. She asked that I excuse the messy
house, and I told her not to mind.


Her bed was a queen size in one corner of the room, piled with pillows
and stuffed animals. We hadn't discussed what her donation would be, so I
asked. She responded almost shyly with a very reasonable number, and I
peeled off some bills from my wallet and put them on the nightstand. Then
she pulled me against her body and kissed me, and I damn near fell in
love. She kicked off her heels, making us about the same height, put her
arms around me, and pressed her body completely against mine. Her eyes
closed, her head tilted, her mouth opened, and our tongues wrapped around
each other. She sighed and I sighed. This wasn't going to be a
well-controlled commercial sex. She was into it.


I ran my hands up and down her back, to her ass then back to her hair. We
made out like that for a few minutes, then broke apart. Her eyes sought
my own, and she smiled brightly. I undressed and lay down on the bed
while she stripped off her bra and panties, leaving the corset on. She
joined me on the bed, where we lay on our sides facing each other. I told
her I wanted to take my time and explore, that at some point I wanted to
be inside her, and I wanted her inside me. She said that sounded
wonderful, but not to expect too much from her topping. She said she'd
been taking hormones for the last few months, and was starting to lose
the ability to hold an erection. I told her not to worry about it, that
we'd see what happened, and we went back to making out.


We kissed and kissed, deeply, mouths open, tongues exploring. I nibbled
gently at her upper lip, then turned her head to kiss my way around her
neck. Her free hand roamed my body, grasping my hardening cock and
stroking me, then caressing my balls, then reaching to take hold of my
ass and pull me against her. I cupped her small breasts, probably a
healthy A cup, maybe a B. Her skin was so nice -- soft and unblemished --
and I kissed my way down to her nipples. I took each one into my mouth in
turn, sucking hard on it, then biting and pulling gently with my teeth. I
told her they were beautiful and perfect, and that I loved her soft skin.
I licked my way around each one, then sucked again. She began softly
moaning, with actual passion, nothing faked. While I pleasured her
nipples I reached down and held her cock and balls in my hand, gently
caressing her there with my palm and fingertips. It was small, not more
than an inch or so soft, completely free of hair, as was the rest of her
body with the exception of her head. She spread her legs to give me
complete access. I held her balls in the palm of my hand and extended my
fingertips to stroke her perineum, and tease my way up between the globes
of her ass to her back entrance.


High on sex, I wanted more. I gently eased her onto her back and crawled
naked between her legs. I kissed and licked her balls, then settled my
mouth over her, taking the whole package into my mouth. Backing off a
little, I started sucking her cock hard, pulling on it with my mouth, and
it started to grow. I kept one hand on her thigh for balance. With the
other I moved around, holding her balls, teasing her perineum with my
fingertips, then spreading her cheeks and running a fingertip around her
asshole, then starting all over. I sucked her for about 15 minutes as she
grew harder and harder. Fully raised, her cock was about 4" long, uncut
and slender. I told her that I loved her cock, that it was the perfect
size to fuck me, that I couldn't wait for that to happen. I pushed her
foreskin back with my tongue and licked my way around the head, then took
almost all of her back into my mouth. I held her shaft against the roof
of my mouth and ran my tongue up and down along its length, drawing a
moan from her, and a tremble of her hips. Then I wet one of my fingers in
my mouth and slid it into her asshole, fingerfucking her as I sucked. I'm
not going to say I'm some expert, I just make it up as I go along, but
she was clearly enjoying my performance. I kept my hand and mouth dancing
around her genitals, and it was all having a great affect on her.


Then I wanted to go farther again. Gently pressing against her hip, I
told her I wanted her up on all fours. I knelt behind her and pulled her
cheeks apart with my hands. Her hole was small and appeared very tight. I
took her cock in one hand and stroked it like I was milking a cow. I held
her cheeks open with the other, and with one long lick I went from the
base of her shaft to her asshole. Rimming has never been a thing that
excited me, but I was certain she was absolutely clean inside and out,
and I wanted to take advantage of this opportunity. I ran my tongue
around the periphery of her hole, than stiffened my tongue and pressed
into the opening. It slid open more easily than I expected, and my tongue
slid inside her ass. She moaned again, telling me how good it all felt,
telling me she loved my mouth on her cock and ass. Her hips pushed back
against my mouth, forcing my tongue deeper inside her. I stayed there for
a while, kissing and licking everything in sight. I ran my tongue up and
down the backs of her thighs, sucked her cock into my mouth, then worked
my way back to eating her ass, licking the hole and pressing my tongue
inside her. Once again I wet a finger in my mouth and pushed it deep
inside her while licking her cock and balls. I fingerfucked her while
sucking her balls into my mouth, running my tongue around them. I added
another finger and fucked harder into her ass.


Getting a little sore from the contorted position, I moved up alongside
her on the bed again. She rolled onto her side and pressed her body
against mine, and we kissed for a long time. She seemed completely
comfortable with taking into her mouth a tongue that had just been in her
ass. In between breaths I told her I loved her body, and she told me she
loved what I did to it. I complimented her again on her skin, so perfect
and soft, while pulling on her ass to bring our cocks together between
our bellies. We kissed some more, moaning our pleasure into each others'
mouths as we pressed our bodies together.


Then Jillian pushed gently away, and said, smiling, "Your turn!"
Separating my legs, she climbed between them. I lay on my back as she
grabbed hold of my cock and buried it in her mouth. She was good at this,
and she used all her skills. I looked down at her face and our eyes
locked. She smiled at me as she dived back onto my cock. She wrapped one
hand around my cock and used the other to tease my balls and my asshole.
I lay back and closed my eyes, concentrating on the feelings in my groin.
I told her she was amazing, her mouth felt incredible. Then I said, "Do
you want me to talk dirty to you?" She moaned slightly, and I could hear
a smile in her voice. "Yes, I love that," she said, "It turns me on."


"Suck my cock, baby doll," I said. "I like the feel of your mouth
going up and down on me. I like the way you tease my asshole with your
fingers. Blow me good, get me nice and hard. I want your cock in my
ass."


Then she guided me up onto my knees and knelt behind me. Separating my
ass cheeks with her hands, she pressed her mouth to my asshole, licking
and sucking, then pushing her tongue inside me. Just as I had done, she
stroked my hard cock while eating out my asshole. God, it felt amazing.
"Baby, fuck my ass with your tongue," I told her. "That feels so
fantastic." She stayed there a while, alternating between sucking my
cock and licking my asshole.


"Fuck me," I told her, "I want that dick of yours in my ass."


"Yesss, baby," she hissed. Getting to her knees, she reached over to
grab a bottle of lube from the nightstand. Opening it, she greased up two
fingers. Rubbing them around the edge of my hole, she lubricated the
outside. Adding more lube to her fingers, she plunged them into my ass,
pressing deep, then beginning an in-and-out motion, fucking my hole while
lubricating and stretching it.


She was still hard from my blowjob, and she applied lube to her rod and
leaned into me. I was a bit surprised she didn't put a condom on, but I
was too far into lust to care very much. She slid all the way in in a
single long stroke, and I felt her balls hit mine. Grabbing my hips, she
began a slow fucking motion, allowing me to get used to the penetration,
speeding up bit by bit.


"Fuck me," I said again, "Feel my ass squeezing your cock. Drive that
thing deep into me!"


"Yes, sweetie," she replied, "I'm going to fuck you good and hard."


It wasn't working as good as I would have liked. As she'd said earlier,
her erection was undependable. It softened and fell out a few times.
Still, I loved every minute of it. I reached behind me to grab her hips
and pull her hard against me. I forced my hips up and back against her,
saying "I'm gonna fuck your cock with my ass." I reached under both of
us to squeeze her balls as she fucked.


I pulled a big stuffed elephant from the pile next to us and put it under
my hips, then slowly lay down on my belly, my legs wide apart. Reaching
back, I pulled the cheeks of my ass apart, opening myself wide to her. I
flexed my anal muscles, winking the hole at her. She finger-fucked me
again while she stroked herself back to hardness, telling me she wanted
my ass, that it was so beautiful and felt so good on her cock.


She fucked me on and off like that for 20 minutes or so. She lay on my
back, pushing her hips to thrust into me. I turned my head and we kissed
as I told her how good she felt inside me. "Ohhhh, Jill, it's so nice.
Your cock pushing in and out feels so fantastic. You can do that all
night if you like."


Finally she had enough. She wasn't going to cum, and gave up the effort.
Sliding off, she came to lay alongside me, and we pressed against each
other and kissed some more. Our hands rambled over each others' bodies,
groping and caressing. Between kisses, I told her that this felt much
more like making love than fucking, and she smiled and nodded. "I'm
enjoying every minute," she said. "You're staying on my client list
with a star next to your name for priority. You've got a big cock and a
great body." We kissed a little longer, then she said she wanted me
inside her. She rolled me onto my back and went down on my cock, sucking
and licking everywhere until she'd restored it to full hardness. "How do
you want me?" she asked. "On your back," I replied. I want to look at
you while I fuck your hole."


Smiling, she rolled onto her back, pulling her knees up and spreading
them wide. I grabbed the trusty elephant and slid it under her hips,
raising them to the right height. Then I grabbed the lube. I spread some
on her asshole, then used a finger to spread it inside, I poured some on
my pole and stroked it for a minute, making sure it was up to the task.
Then I slid forward with my thighs outside her ass cheeks and pressed the
tip against her hole. "Push it hard," she said, "I love it that way,
and I really want your big cock inside me."


Holding the base of my cock in my hand, I pressed forward, and sure
enough, the head slid right through all barriers, and I kept sliding
until all seven inches were buried inside her. Both of us moaned in
pleasure. The tightness of her hole was incredible. Leaning forward I
took one of her nipples in my mouth and began fucking her. I sucked and
pulled on that nipple, then repeated on the other. Flexing my hips as I
fucked her, I looked down at her pretty face. Our eyes locked, then
closed as I pressed my lips against her, our tongues moving and
penetrating each others' mouths as my cock penetrated her ass again and
again. I'd love to say I fucked her in 47 different positions for hours,
but I'm not a young man -- when the feeling of impending orgasm begins, I
have to strike while the iron is hot. I felt it starting, and went to
work. Rising up in my arms, I looked into her eyes and told her I was
going to cum soon. "Yesssssss," she said, "fuck me hard, cum deep in
my pussy!"


I jackhammered her hole, pulling out til only the head remained, then
slamming my hips against her ass as I pounded deep inside her. It didn't
take too long, maybe a dozen strokes, before I felt my load rising up in
my balls. I mumbled obscenities, "Fuck, fuck, I'm coming in your ass!
You're so fucking tight! Squeeze my cock with your asshole!" She did,
and my orgasm arrived. I slammed all the way into her and fell against
her breasts. She held me against her as my cock spasmed and pushed its
load deep inside. We lay like that for several minutes, regaining our
breath, then I rolled off to her side, again pulling her against me.


"I'm the kind of girl who likes to cuddle afterwards," she breathed
into my face. "Hope you don't mind."


"No, baby, I'm very happy here. I'll stay just like this as long as you
like." We kissed for a while, then she nestled down against my neck. I
rolled onto my back, her head on my chest, her leg thrown across my
thighs. Her hand played idly with my softened cock.


We talked and laughed. I wish I could remember that conversation word for
word. We held hands, talked about how good it had been, what we liked,
what we might like to do some other time. It felt like time spent with a
longtime lover, and I enjoyed every moment. I'm not sure how long we lay
like that, at least half an hour. Finally we both began to get restless.
Rising, I put my clothes back on. She went through a drawer looking for
fresh underwear, saying something about a date later who liked her in a
thong.


We finally edged towards the door, but it took a long time to get there.
I commented on some of the antiques in her living room, and we talked for
a few minutes about old photographs. We edged towards the door again, but
she leaned in and kissed me, and we locked into a tight embrace with
wrestling tongues and roving hands for another few minutes. She told me
that she felt a great connection with me, and looked forward to seeing me
again. She said that, as I had mentioned, being with me felt like making
love. Eventually she saw me out the door.  I was mildly surprised when I
saw the car clock and found we had spent two hours together.  I hadn't
spent that long in bed with anybody since my divorce.  I drove home with
a giant smile on my face.


We're already texting about our next meeting.

If you want to comment, my email is up there in the header.