Simones Abenteuer
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Simone's First Time free porn video
Simone's First Time
By Simone Clark
By day, you wouldn't think that I am a crossdresser. I have a "manly"
job and give no indication that by night I long to be in a dress and
high heels acting as feminine as possible.
I have dipped my toe in the trans community, and even made a friend in
Ada, a girl like me that I met while getting a makeover in the suburbs
of Chicago a few years ago. Ada and I have met in both male and female
mode quite a few times over the years but this weekend will be
different.......I am finally stepping out to a transgender club nearby
Ada's home as Simone.
As the day approached, I made sure that I was prepared. I was planning
on wearing my favorite knee length bottle green chengosam, black seamed
hose and a garter belt; black patent d'orsay cut heels with an ankle
strap and my favorite auburn bob length wig. I even packed a daytime
outfit consisting of a knee length leather skirt, black pantyhose, a
blue satin blouse and a pair of 3 inch heeled knee high boots. I also
made sure that I had the needed cosmetics and a few other accoutrements
that are essential to a truly feminine appearance.
On the fateful day, I kissed my wife goodbye, as she was going to Europe
with her aunt, and began my preparations in earnest.....First I
adjourned to my computer room and opened up my feminization hypnosis
software. I listened to "female for a day", and "train crossdress sex",
which merely deepened the effects of the first program.
I then moved to the bathroom and covered my body (except my pubic patch)
with Nair and waited for the hair to fall from my body. After a
freshening shower, I covered my body with a lightly scented moisturizer
and dressed in boy mode for my travel to Ada's house. I ensured I had
everything I needed and went to my car.
As I made the hour plus journey, I began to feel the effects of the
hypnosis, I noticed the sensitivity of my smooth skin under my clothes
and the light, feminine scent coming from my body and I felt a shudder
of pleasure. The trip passed quickly, and I found myself on Ada's
doorstep.
After some catching up, we began to discuss the evening's preparations.
Ada told me her female friend Sally was going to come over and give us
both manicures and help us with our makeup. I was shown my room and
began to unpack Simone's things in the dresser and closet provided.
Before I knew it Sally was ringing the doorbell, and the preparations
began. Sally was wonderful and understanding, she saw what I was going
to be dressed in and co-ordinated my makeup to flatter my face. My false
nails were attached and painted a luscious deep red, when they were dry,
I retired to the bedroom to change.
I first placed by silicone c-cup breasts in my bra and buckled it on my
back. I then carefully removed my sheer seamed stockings from the
package and put on my garter belt. I rolled the stockings up my smooth
legs and attached the 4 metal garters to each leg. I then put on my butt
and hip enhancers to give me the ultra feminine shape I craved. I
stepped into my green satin dress and it whispered against my hose, and
then buttoned it in place. I then sat on the bed and put my patent
leather heels on, buckling the ankle straps securely. I was now 4 inches
taller and feeling ultra feminine. I then placed my wig on my head,
affixed my matching green and gold earrings to my ears, and dabbed a bit
of perfume to my wrist and back of my left knee, and exited the room as
my alter ego Simone.
Ada had also been preparing for our evening out, and she emerged from
her room in a stunning blue jersey dress that clung tightly to her frame
and, black hose along with simple pair of black patent pumps with 4 inch
heels. We complimented each other on our fine fashion sense and went to
the garage and got in Ada's car. We were going to a very TG friendly
club. It was Friday night so many of her friends were going to be there,
as well as many gentlemen admirers.
As for me, I consider myself heterosexual, but as I looked at my nylon
clad legs and dress, I felt that that hard and fast line was begin to
blur....
We arrived at the club and it appeared that the party was in full swing.
Girls, guys, and everything in between were interacting happily with
each other and the booze was flowing. We chose a booth and I began to
meet some of Ada's friends. They all seemed very nice, the one thing
that surprised me is that they were from all walks of life, and the
thing that brought this diverse group together was their desire to be
women, at least for a while. I found myself carried away with my role; I
was speaking as a woman, moving as a woman, and generally behaving as a
woman. I idly wondered if the hypnosis was helping me be the woman I was
projecting to this crowd. After a few drinks, a man approached the table
and asked Ada to dance. Ada appeared to know the gentleman, and
introduced him as Mark. Mark appeared to be a perfect gentleman, and
treated Ada as a girlfriend. I watched them dance a few slow numbers,
and I could swear that Ada was a total woman for this man. I felt a pang
of jealousy at the way Ada was being treated, which both surprised me
and worried me at the same time. Ada came back over with Mark and
another man who was introduced as Jeff. Jeff was handsome, with a nice
fit frame and an easy manner. Jeff sat next to me, and Mark sat next to
Ada and we began talking and generally having a good time. After about
an hour, Mark suggested that we all head back to his place for a
nightcap, and the next thing I knew we were in Ada's car heading into
Chicago to Mark's townhouse.
Mark had a very expensive townhouse overlooking the Gold Coast facing
the lake. It was very well appointed and nicely furnished. I noticed
that Ada, had taken Mark's hand before we left the club, and now as we
entered his home they were arm and arm like a boyfriend and girlfriend
would be after a night out on the town. Jeff followed closely behind me,
I felt the heat from his body as he ushered me into the townhouse. Mark
poured us all drinks and we were having light conversation when I saw
Ada kiss Mark on the lips. I was a bit shocked, I did not know Ada was
like this, but at the same time that pang of jealousy returned and I
felt myself wishing for a moment that Jeff had kissed me! Mark stood up
and led Ada to what I believed to be his bedroom. I felt very awkward,
here I was dressed as a sexy woman sitting with a man and I was
beginning to wonder what was happening between my friend and Mark.
Curiosity got the better of me, and I got up and peeked in the room that
they had retired to. I left Jeff sitting on the couch and saw that the
door was cracked a bit so I peeked, and was shocked to find my friend
Ada on her knees sucking on Mark's cock. She was going to town, making
high feminine squeals and sucking noises as her lips moved up and down
on Marks saliva covered shaft.
I was so absorbed with the spectacle before me that I did not notice
Jeff come up behind me. Jeff bent close to my ear and whispered
"enjoying the show"?
I could barely contain my startle reflex and fell into Jeff who caught
me by the shoulders.
I tried to come up with an excuse, but Jeff waved them all aside, he
said "would you like to do to me what Ada is doing to Mark"?
I found myself whispering "yes Jeff I would".
He led me into the other bedroom and told me to get on my knees, which I
did. I felt my nylon clad knees sink into the rich carpet and he took
his place in front of me. My red tipped fingers gently unclasped his
belt and pants and unzipped his zipper, which dropped his pants to the
floor. I reached for the waistband of his jockey shorts and was greeted
by his thick cock flopping out. As I stared at his cock, a passage from
one of my hypnosis programs sprung into my head "if you choose to suck
on another man's penis, you will find it very enjoyable". I kissed the
head of his penis and sucked tentatively at the very tip, finding it
salty but not unpleasant. Jeff praised me and encouraged me to do more,
so I found myself opening my mouth and engulfing his penis, and working
it with lips and tongue. He moaned with pleasure, and I began to move up
and down his shaft, staining his bare cock with my lipstick, and making
the same sucking noises I heard my friend Ada making only moments
before. After about 5 minutes, Jeff said "Simone, I'm going to cum". I
locked on to his shaft and buried as deep as I could in my mouth. I felt
a hot, salty substance fill my mouth and Jeff grunt with pleasure and
satisfaction. I swallowed the whole load, idly wondering why women found
this to be so unpleasant. I then released Jeff's cock from my mouth and
took a drink of the brandy I brought into the room with us. He then
brought me to my feet and kissed me deeply. We then went back out to the
living room to snuggle and touch each other. Ada then emerged from the
room fresh as a daisy and announced that it was time to go home. I
freshened my lipstick, and we left the townhouse after making a date for
lunch with them the next day.
As we got in the car Ada said "so, how was it"?
I tried to deny that anything happened, but Ada was not having it. She
said "it's ok if you enjoyed it, that's the reason I introduced you to
Jeff".
I was quiet on the ride home, but as we got closer to Ada's house we
started talking about what we were going to do about lunch the next day.
As I prepared for bed, I began to process all that happened to me that
evening. I actually went into a place dressed as a woman, met a man, and
then sucked his cock and swallowed his cum?!?!?! I could hardly believe
it, but there was no denying the pleasure I felt as I was doing
it.....and I began to realize that I wanted more. I went to bed and
listened to my female for a day hypnosis program, and drifted off to a
sleep full of feminine thoughts and feelings.
When I woke up, I went to the bathroom and cleaned myself up, took a
shower, applied my day makeup and returned to my bedroom to change. I
put on my bra, panties and pantyhose on, stepped into my leather skirt,
tucked in my satin blouse and sat on the bed to put on my boots. I
slipped my nyloned feet into the boots and zipped them closed along my
inner calves and stood up and walked to the mirror to check my look. I
looked like a slightly sexy secretary, which was the look I was going
for.
I made my way into the kitchen and was greeted by Ada, who was dressed
in a woman's navy pinstriped skirt suit, complete with black hose and 3
inch sensible pumps. We had coffee and a danish and it was explained to
me that we were meeting the boys at a nice place for lunch in the
business part of town by the commerce exchange. She said that we would
both fit in and not be read....her as the smart career woman, and me as
the sexy assistant. We got in the car again and met the boys for lunch.
As we were walking down the sidewalk, I began to believe Ada, we did in
fact look like every other woman on the street. I saw several women
turned out in smart skirt suits and heels, and even a few women in
leather skirts and knee high boots. Upon arriving at the restaurant,
Jeff kissed me on the cheek as we greeted one another. I returned his
kiss and we sat down across from Ada and Mark and ordered lunch and a
bottle of wine. Jeff was really attentive and I felt like the only woman
in the room. The boys then announced a surprise, they were taking the
rest of the day off, and wanted us to come with them back to Mark's
townhouse. They promised dinner and a movie if we decided to go with
them.
I was feeling slightly buzzed from the wine and both of us readily
agreed. We met them back at the townhouse, where they opened another
bottle of wine and we all sat down to talk. Jeff complimented me on my
outfit and said he always loved it when a woman wore boots and a leather
skirt....it made her both powerful and sexy. I felt a bit giddy when Ada
and Mark left the room and in hand again, knowing full well that I would
be doing the same momentarily.
Jeff wasted no time. He kissed me on the lips and slid his tongue in my
mouth, I willingly accepted it and we both stood and made our way into
the spare bedroom. I began to remove Jeff's clothes, noticing his cock
hardening as I did so. I dropped to my knees and sucked at the head of
his cock, but Jeff had other plans.
Jeff removed my leather skirt, exposing my pantyhose, and told me to
bend over on the bed. I willingly complied and he pulled down my hose
exposing my boy pussy. I felt one of his fingers slather a cold
substance on my rosebud, and I heard a condom package being ripped open.
I turned and helped Jeff on with the ribbed condom, then assumed my bent
over position once again. I heard the bed slamming against the wall in
the other room, and could only assume that Ada was receiving the same
treatment as I was about to.
I had never done anything like this before, up to this point I
considered myself hetero sexual, I now knew that that was no longer a
fact......I was excited, scared, and full of anticipation. My reverie
was interrupted by Jeff's cock being pushed into me. It hurt at first,
but after the first few strokes I was meeting his thrusts and moaning in
pleasure. The sex seemed to last forever, I was so enraptured I barely
noticed when Jeff came in me. He collapsed on my back and we lay on the
bed in satisfaction. After a few moments I made my way to the bathroom,
cleaned myself up and returned to the bed fully dressed. Jeff Kissed my
nyloned legs and the toes of my boots complementing me on my sexy ways
and clothes. I was still burning, so I pinned him to the bed, cleaned
his cock, and gave him a porn star style blowjob. The moment he came in
my mouth I was filled with pleasure.
We then regrouped and had dinner in the townhouse after a short trip to
a market for supplies. After dinner, we repeated our afternoon
performance, leaving two satisfied men in our wake.
The next morning I had to leave and return home. So much had happened
in the space of two days, I was questioning my very existence as a man.
I finally understood after years of struggle with Simone that she was a
part of me, and she was not going away. I thanked Ada for her
hospitality and vowed to return as Simone for more adventures.
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