Jan and John s Sexual Exploration
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Evening Of Exploration 2 free porn video
As Karen and I walked hand in hand to the hotel, I smiled thinking back
on what had already passed tonight. It was the first time I had ever
gone out of my house fully dressed as a woman. I had chosen some of my
sexiest lingerie for the milestone and my favorite purple sleeveless
cowl neck dress, which I'd paired with my long wool powder blue coat to
keep warm and a matching pair of strappy heels.
I had come to a bar to meet my friend Karen, who up until now, I had
only spoken to online. After chatting for a bit, a pair of handsome
young gentlemen had come over to buy us a drink, and we discovered that
they too were crossdressers, and that they were wearing lingerie under
their boy clothes. Suffice it to say that after a few more drinks,
things became amorous, and we all paired up, with Karen and I each
making out with one of the boys, my first time kissing another man.
And after they man, Joseph, had made me come by rubbing and pressing
against my panty clad cock, I had on the spur of the moment decided to
go down to my knees and give my first ever blowjob. It had been
fantastic and intensely erotic. I had pleased a man sexually, but it
seemed perfectly natural dressed as I was. But unfortunately we had
finally taken our leave of the boys because right now the only thing on
my mind was Karen, how we had shared our first kiss, and how we were
about to explore our dressing, our bodies, and our sexuality further at
the hotel.
We walked into the lobby of a simple hotel and straight to the elevator.
Once we got on the elevator car, Karen positioned herself behind me and
began pressing her body to mine. I had put my coat on while we were
outside, but I could feel her noticeable bulge even through the wool
material. She whispered into my ear how horny I was making her by
looking so cute, and how much she had enjoyed the show I'd put on,
sucking a cock in a public place. She began licking my ear lobe and with
her hands, pulled apart the front of my coat. They slid up the silky
material of my dress, and she started to rub my breast with one hand,
and my crotch with the other. I had cum once already, and the wet pad
seemed to only further heighten my awareness of my penis. I reached back
with my hands and firmly grasped her ass, massaging the cheeks and
telling her that I couldn't wait to be on the other side of her,
grabbing those cheeks and fucking her silly. She laughed at this and
replied with a simple, not if I do you first.
The elevator finally arrived at our floor, and she led me down the hall
to our room. Opening the door, she showed me a tastefully decorated
suite with a living room and the bedroom just beyond it. There was
champagne set out in the living room, and Karen poured each of us a
glass.
"To an evening of exploration," she toasted.
Our glasses clinked and after a sip of champagne we put down our glasses
and fell into each others' arms, kissing and groping. I undid the bun
which held the mass of hair that was her wig up, and the red locks came
flowing down around her shoulders. I unbuttoned her silk blouse and
pulled it off her to reveal a wonderful lacy white bra beneath her ivory
slip. I massaged her breasts as our lips melted together and she let out
a moan. Next came her skirt, which I unzipped and allowed to fall to the
floor, showing off the rest of her slip, delicately hemmed in ivory
lace.
Karen in turn had worked my dress all the way up to my waist and took
the moment where I was admiring her lingerie to pull it the rest of the
way up my body and over my head, somehow managing to keep my wig in
place. She told me how pretty and sexy my slip made me look, and I
returned the compliment, adding that if she liked the slip, she would
love my bra and panties. With that, we each pulled off our slips, and
stood checking out the other's lingerie. She had on a white thong with
scalloped pink lace edges around the leg holes, and a pink flower right
at the center of the waist. The thin material barely restrained her
bulge and was all the sexier for being so completely erotic looking. She
was also wearing a matching garter belt which held up her black seamed
stockings.
I told her how much I loved her lingerie, and she replied that maybe I
could borrow it sometime. At this point Karen reached out and began to
run her hands along my body. Starting with the dark purple bra I was
wearing she traced the underwire of the bra, ran her fingers down to the
top of my matching waist cincher/garter belt, which held up my own smoke
grey stockings and gave me my feminine shape. Next her hand cupped the
bulge in my purple high waist control panty and began massaging me
through the satin and nylon. We were both still standing in our heels,
me in my purple strappy sandals, and her in a pair of black pumps, and
now my hand reached over and began to touch the edges of Karen's
undergarments. Our lips locked again, and now with both of us unclothed,
but in sexy lingerie, we made our way to the bedroom.
I laid Karen down on the bed, and worked my way down her body, sliding
my hands to the inside of her breast forms so that I could rub her
nipples and running my hands down the side of her body. I kissed her
stomach, and licked around the lace edges of her garter, and then
stopped to slowly pull her panties over the top of her penis. I slid
them down her legs, at the same time rubbing the nylon wrapped around
her legs, and became entranced by the feel of so much femininity wrapped
around a manly body.
I dropped her panties to the floor and returned to her cock, which was
now fully erect and dripping pre-cum. I licked off the tip, eliciting a
moan, just as I had earlier with Joseph when I'd given my first blowjob,
and then started to lick around her six inches. I gave a kiss to her
balls, and then began massaging them with one hand while grasping the
base of her cock with the other. I pursed my lips slightly and then
slowly sucked her full length into my mouth, savoring every inch of her
manhood. She twitched slightly as I began to move my lips up and down
her penis, and I heard Karen start to really moan and tell me how good
it felt and how much she loved having me suck her.
She called me her pretty bitch and a cock sucking boy-girl, and the
erotic talk only excited me further and I sucked even harder. She pulled
her legs up over my shoulders and dug her heels into my back, urging me
forward. I felt her whole body begin to tense and knew that her orgasm
was near. I pulled off her penis for a second and looking into her eyes,
I licked my fingers and put them in my mouth, wetting them. She knew
instantly what was about to happen, and slid further down the bed
towards me, and as I took her cock back into my mouth I began to rub my
wet fingers against her ass opening.
I continued my dutiful sucking and stroking of her penis and then begin
working my index finger into her ass, finally plunging it in, one
knuckle at a time. She let out a yelp as I penetrated her, and another
when my first finger was joined by a second. I started to loosen her up
and when I worked my third finger in, it was all she could take. Her
whole body began spasming and while screaming out my name, she came with
a flood of semen into my mouth. I swallowed her seed as quickly as I
could, but a bit leaked out the side of my mouth.
It felt so sexy to feel cum dribbling down the side of my face and
realizing that I'd just pleased my second man that evening with a great
blowjob. Karen's body post-orgasm was now totally limp, and as I cleaned
off her cock, I removed my fingers and then moved up next to her face.
She had an angelic smile on her face, and as our eyes met, I kissed her,
parting her lips, and giving her back some of the cum she had shot into
my mouth. Her eyes opened, surprised for a second by the fluid, but
then she smiled, swallowed, and pulling away for a second told me I was
naughty for giving her such a surprise.
I asked her what she wanted to do next, and she said that it was only
fair that she return the favor. With that, she now slid down the bed,
and pulled my panties down with her, releasing my cock. I had cum once
already into the maxi pad I'd placed in my panties, so my penis was wet
with my own cum. Karen licked it clean before sliding my panties the
rest of the way down my legs. Her hands rubbing my stockings sent
shivers up my spine and turned me on to no end.
She began pleasuring me much the same way I'd done her earlier, kissing
all around my crotch area before finally taking my cock into her mouth.
I knew it was the first time she'd ever done this, but she seemed like a
pro. Her lips around my penis were soft without being limp. Firmly she
sucked on it, and she used her hands to alternately massage my ass
cheeks and also wrap them around my penis and slowly masturbate me. I
could feel my orgasm start to build, and my hands found the back of her
head, urging her on.
As I looked down, I caught her glance, and seeing a sexy girl/boy in
beautiful lingerie giving me a blowjob turned me on even further. My
eyes moved from her high heels to her stocking clad legs, up her legs to
the garters which were two taut stripes that moved up her sumptuous ass,
to the bra strap that was holding in her "breasts", and the fabulous red
mane of hair that fell about her shoulders now. I ran my finger through
her hair, and glanced over my body. I admired my own legs, also in heels
and stockings, with a garter holding them up.
My "breasts", bouncing to the rhythm of Karen's motion up and down my
cock. The strands of my wig, brushing against my cheeks. The whole scene
was incredibly erotic, and then when Karen suddenly moved her fingers
right to the entrance of my ass and started to slide her fingers in, it
was too much for me, and I came in an explosion of semen into her mouth,
one of the most intense orgasms I had ever experienced up until that
point. It seemed like my entire body poured into her mouth as I came,
and I let out a slow soft whimper as I felt my orgasm reach its height
and then begin to subside. It was amazing.
Karen slid back up next to me and pulled me close to her, spooning me
from behind. She kissed my shoulder, stroked my hair, and whispered to
me how much she had enjoyed sucking on my cock. I felt incredibly
relaxed having come twice already tonight. Laying there with her strong
arms wrapped around me, our stockinged legs tangled together, and the
scent of sex all over the room, I knew that we weren't done. I could
feel her erection pressing into my ass. She had gotten hard while giving
me a blowjob, and I wasn't about to leave her unsatisfied.
I knew that to make this night complete, one more thing had to happen
for each of us. We both needed to be fucked. I started to wiggle my rear
end and rub it up against her cock, and she could tell that what I
wanted next was to be treated like a woman. I turned to face her, and
kissed her passionately on the lips, giving plenty of tongue. As I
pulled off her sexy lips, I told her what I wanted. I wanted her to put
me on my hands and knees, to slide her hot cock into my virgin ass, and
to fuck me and fill me up like the pretty bitch that I am.
And then after that, I would take her virginity too, however she wanted
it. Our eyes met once again and she simply smiled before flipping me
onto my belly, and then starting to lick my ass. She tongued my asshole
and got me really wet, and then I rose to my hands and knees and pushed
my ass out to her. I heard her opening a condom package, and then felt
something cool being applied to my ass. Apparently she'd brought
lubricant with her. First one finger went in, and then another. She slid
them in and out of my ass while I got used to their size.
As she pulled them out, I whimpered and begged her for more. That was
when I felt the tip of her cock at my ass, and she started pushing it
in. I had never had anything this large in me before, and I felt some
pain as she stretched out my rectum. But the pleasure of being filled up
started to overtake any other feelings, and soon I was pushing back to
her as she slid in. Finally she was all the way inside of me, and once
her balls hit mine, she pulled back out so that just her tip was in me.
"Ready?" Karen asked.
And without waiting for an answer, she thrust her cock back into me. She
began a steady pumping motion, in and out of my ass pussy. And I met her
every thrust by pushing my ass back towards her. It was incredible. I
was being fucked. I felt like a woman. Like a girl giving it up for the
first time. Getting pounded by some sexy boy. Except that when I looked
back, it was a beautiful woman giving me my fucking. I moaned in time to
her grunts, and she asked whether I liked being her bitch, her fuck-toy.
I cried back that I loved taking it in the ass and that I couldn't get
enough as her bitch. I told her I wanted more, that I wanted her to fill
me with her cum. She told me to be patient, and slapped my butt cheeks.
Then she put both of her hands on my hips, and began pulling me onto
her. My head was being pushed into the pillow, and I became lost in the
sensation of getting fucked. Then I felt Karen's hand come around to my
front and begin massaging my tits. She played with them, and I felt the
silicone rub my nipples. Her hand then slid down to my cock and began
pumping me in unison with her thrusts. My orgasm started to build, but I
pulled her hands away from my penis, and put them back on my breast. I
wanted to come, but not yet, and not here. There was a very specific
place I wanted to have my last orgasm of the night.
I felt Karen start to increase her speed, and then she started to shout
out that she was close. This only egged me on, and I pushed back against
her even harder, telling her that I was her slut, and that I needed her
cum inside my pussy. I could feel her erection get bigger in my ass, and
then I hear her start to scream in ecstasy that she was coming. I felt
her cock twitch over and over, and she gave one final hard thrust, which
almost made me spill my seed as well all over the bed. I almost
convinced myself that I felt her shooting her cum into my ass, but knew
that it was all safely in the condom she'd slid on before entering me.
Karen collapsed on top of me, and I fell to the bed as well, falling
from my hands and knees. Her cock was still inside of me, although
shrinking and no longer filling me as it had while she was pumping into
me. She laid on top of me, and whispered to me that it was one of the
most amazing orgasms she had ever had. We stayed in that position for
what seemed like hours, the tip of her cock still in my ass, and our
bodies relaxed and our warmth shared between them.
Slowly Karen rolled off of me and her cock came out of my ass with a
slight pop. She unrolled the condom and dropped it onto the nightstand
table. Then she pulled me over close to her and began to kiss me
tenderly. She said that she had enjoyed every moment of the evening, and
that there was one more thing she wanted us to share. With that she
reached down and began to stroke my cock to a full erection again. I
slid above her and spread her legs apart.
The bottle of lubricant she had used on me lay open on the ground next
to the bed, and I poured some onto my fingers and then began rubbing it
onto the entrance to her ass. I slid one of my fingers into her opening,
and she gave a little gasp, as she had earlier. I added a second finger
to it, and slowly massaged her opening to relax her anus before pulling
out. She reached over to the nightstand and handed me a condom as well,
and I opened the package, poured a little lubricant onto my cock, and
then slid the condom onto my penis, being sure to pinch the tip to leave
space for the semen that was soon to fill it.
I took her legs and pulled them up over my shoulders to get a better
angle at her ass pussy, and then positioned the tip of my cock at her
opening. With a smile on my face, I looked her in the eyes and told her
to prepare to get fucked, and then I pushed hard into her ass. She
yelped as I entered her all the way so that my groin pushed right up to
her butt cheeks, and as I pulled back out, she let out a breath and
asked to be fucked like a whore, to pump my cock hard into her. I
replied without words and began to fuck her.
The tightness of her ass was incredible, holding me more firmly than any
woman's vagina I had ever fucked. It seemed to grip my cock and with
every stroke, hold onto me just a bit more strongly. I leaned forward
and began first stroking Karen's breasts, then holding her hands down on
the bed, and also kissing her hard on the lips. Every time I pulled off
of her mouth she would moan for me to fuck her harder and I would
respond by thrusting deeper into her ass, feeling my orgasm building to
the brink. I continued pumping into her for what seemed like forever.
I became lost in the sensations again. Fucking another man. Wearing
lingerie. Feeling like a freshly fucked woman. I moved my hands down to
her cock and began stroking her penis, which had become erect again. I
started jacking her off in rhythm to my thrusts, and felt her start to
stiffen. She reached up with her hands to grab hold of my head, and
pulled me onto her lips hard and as I felt her cock start to spasm with
another orgasm, my own penis could no longer hold back, and I started
cumming into her ass.
Wave after wave of cum shot out of my cock and I was racked with another
incredible orgasm, shouting out how amazing it was fucking her. Karen
screamed out as well as she came between us, onto both of our stomachs
and her chest, releasing whatever sexual energy still remained in her
after our night of exploration. I fell onto her, feeling the stickiness
of her cum rub between us. I kissed her on the lips and held her to me.
Her legs had fallen off my shoulders during our mutual orgasms, and I
laid now between her splayed thighs. My shrinking cock slipped out of
her anus as I got up, and rolled over next to her on the bed. Karen
looked over and our eyes met once more.
"Did you imagine it would be like this?" I asked her.
"I hoped, but nothing more," she replied.
I kissed her again, and our lips opened up to each other, tongues
sparring, and mouths locked together. Our passion wasn't man to man,
woman to woman, or anything like that. We kissed as two individuals
sharing an incredible night of sexual exploration, centered around a
shared love of femininity. I pulled off her and began licking the cum
from her chest and stomach, and she likewise cleaned me off and then we
snuggled up in each other's arms, enjoying the afterglow of multiple
orgasms. In an hour or so I would get up, and get dressed again and head
home, trying to hold onto my final moments as a woman, but for now I
savored the warm sexy body cuddled up against mine, and experiencing the
wonderful feeling of a man who loved to dress in lingerie and dresses
and who had gotten to experience sexuality as a woman.
Jane
- 16.08.2020
- 10
- 0
