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Member Article:My first real date with Michael/Michelle Post Your Comment

rhondanorcal1952 72 T
3  Articles

My first real date with Michael/Michelle

1/16/2018

Michelle and I had met through a mutual male friend at a Street
Rod show but I had met her as her male self, Mike and we hit
it off right away. This happened about 10 years ago after
my divorce from my first wife who for most of the marriage
supported and participated in my crossdressing. Mike
was a really good looking guy and I had fantasies of dressing
for him and kissing his body from head to toe one day. I was
still deep in the closet so soon after my divorce so I just
suppressed those thoughts as best I could. <br><br>
One day I was over at his place, he is single, helping him
work on his rod, his car that is, lol. We naturally got to talking about women and how if it wasn’t for their pussies
most men wouldn’t even bother with a good percentage
of them. We are both divorced and kind of bitter towards
the ex’s I suppose, lol. He was holding a part we were bolting
onto the car and I noticed his finger nails were almost perfectly
manicured and polished a sheer color that I thought I had
in my makeup bag at home. I commented on the manicure, he
said thank you and that my fingers looked very nice also
for a mechanic. That is when I started taking closer looks
at him and found that he was shaved smooth everywhere visible
including his arms. We stopped for lunch and took off our
overalls to go and wash up. When I came back from the bathroom
he had removed his overalls and had just washed his hands
in the sink in the kitchen. He was standing there with his
back to me in what appeared to be women’s walking shorts
and a tee shirt. Through his shirt I could barely make out
the outline of a bra. Now I always have worn at the very least
nice silky panties or thongs under my male attire so I walked
up to him at the sink and put my hand on his back right on a strap
and commented to him how I hadn’t even noticed the bra
he was wearing while he was in his overalls. I also asked
him how long he had been wearing lingerie. He looked kind
of startled and answered since high school off and on but
regularly only over the past few years on a daily basis.
<br><br>
He then told me the reason he was divorced was that his wife
just couldn’t deal with him dressing. I thought to myself,
probably because you most likely looked better than she
did, since I had seen a picture of him, his wife, and their
grown in college. He began to explain, at first
she didn’t mind but after a few years she grew tired of
it and he wanted to dress in at least lingerie all the time.
He explained that he couldn’t and wouldn’t stop. She
told him she couldn’t or wouldn’t stay if he didn’t.
Typical impasse. I told him I had experienced the same exact
thing. <br><br>
I then stepped back and unbuttoned my shorts to show him
the pair of pair black hip huggers with a sheer lace front
panel that showed I was totally shaved, smooth. He whistled
when he saw me standing there with my shorts down around
my ankles and moved to me to cup one of my breasts through
my tank top I was wearing. ( I had come over dressed in overalls,
baggy so my breasts wouldn’t show through, with just
tank top, and a pair of cargo shorts. I was braless that day
which was unusual for me. Since I would be welding and grinding
on the hot rod and wearing the overalls I didn’t want to
take a chance of burning through and ruining a perfectly
nice pretty bra, so braless I was).. I am a full C cup with
barely any sag aside from what time has done to me. He rolled
a nipple between his fingers which drew a small moan from
me. He told me he had wondered if I were bi, or a CD, or hopefully
both. Being unsure he decided it was a great time to find
out one way or another, so he wore lingerie today to see if
I would notice. <br><br>
One thing led to another and we sat and talked for hours,
drinking cocktails, and talking about our lives, former
marriages, what went wrong, how long we had been dressing and our sexual bias
as far as what role we preferred taking. Mike went and got
a couple of photo albums and opened them up for me to see a
very beautiful woman obviously a female, posed with a man
and another very sexy woman. The two women were at his feet
with his fully erect cock at their lips, one on each side
of his cock with their tongues out and flicking each side
of it. He explained the photo saying one woman was the man’s
wife and he was the other woman in the picture. I was so turned
on that I decided right there and then that he and I were going to be inseparable gf’s. <br><br>
As the day wore on with us sitting around the kitchen table,
we decided it was no longer a work day for the hot rod. We went
into the entertainment room where she put on one of her favorite
porn DVDs and said she wanted to get a closer look at my clit
inside my pretty panties. The DVD was one of two shemales
meeting at a dinner party, kind of like us for the first time,
neither of them knowing that the other was not genetic female.
They were very beautiful and how they got together and reacted
to each other finding out neither was female was very sensual
to me. From there one I made the first move on Mike, now Michelle.
She had left to get out of her t shirt and shorts and came back
as Michelle. As she sat down I just had to get my lips around
that cock, oops clit of hers. I knelt between her legs she
lifted her hips slightly and I slipped one leg of her tap
panties up a little to expose a beautiful uncut 6.5” clit
with a small pearl drop of precum at the tip. My tongue went
for the tip and I made a show of licking the end of the foreskin
and then lowering my lips to it I gently sucked as my tongue
slipped inside and probed the opening of her very hard clit.
She laid her head back on the couch as I worked my form of magic
on her. Within minutes of one hand milking her and my mouth
massaging the underside and around the head with a gently
sucking she started moaning aloud sounding like a woman
who is close to cumming. She started to buck her hips into
my mouth fucking my throat and then let out a guttural moan
and began shouting thick spurts of her salty sweet cum in
my mouth. It seemed like she shot 6 large squirts and I tried
my best to swallow it all but a little leaked from the corner
of my mouth. I continued to lick around just under the head
because of the sensitivity I know is there after cumming
to clean her up and bring her down from her orgasm nice and
slow. She finally sat up leaned forward and kissed me long
and deep thanking me and wanting to return the favor. I told
her that is not necessary that I wanted to be completely
dressed for her the next time that we were together. She
was so weak she couldn’t even stand. It was late and I had
to work the next day it being Monday so I got up to leave. I
told her to call me, that I definitely wanted to get some
more thoughts on where she buys her very nice wardrobe in
the closet. We said our goodbyes and I left. <br><br>
Michelle and I chatted over the phone during the week after
our last get together and she wanted to help me get dressed
for our next encounter. “So where do you buy your clothes”
I asked, and where do you buy shoes to be sure of the fit and
makeup without raising other people’s attention. Michelle had been living the lifestyle and at that level
for a long time, well at least as long as me but totally had
surpassed me in style, and readily shared her wealth of
information and tips. She gave me the web site addresses
of some suppliers that I didn’t know about that provided
all kinds of sexy clothes and accessories, as well as retailers
that supported the cross dressing community. That part
of my education wasn’t new to me, but I thoroughly enjoyed
browsing through the sites and seeing what was available.
A woman in sexy clothes always turned me on and now I would
have the opportunity to provide that same feeling to another.
I’m rather short with a voluptuous body with very little
natural body hair and the web sites provided me with enough
information to determine what size clothing I needed.
Needless to say, I was like a little in a candy shop. I
started out with a pair of sexy strap on 4-inch stiletto
heels. Shoes are easy for me I know my women’s size is a
9.5 wide. I remember receiving them via UPS and getting
very excited as I tried them on for the first time. At the
same time, I ordered a few pairs of black crotchless panty
hose, some thigh high lacy stockings and a few more pairs
of silk tap panties and thongs. I also found a very beautiful
black sheath dress laced with gold threads, a long red silk
nightgown, with sheer cover-up, as well as a black lace
up corset. Now I started looking for a sexy looking wig.
I found a number of choices and settled for a curly long auburn
one as well as a short perky blonde one. Michelle liked long
dangling earrings so I purchased a pair of 5-inch long rhinestone
earrings and a three-inch wide choker to match the earrings.
Just ordering them got me very hot and I couldn’t wait
for everything to get here to try them all on. To complete
my new look I needed to buy some make-up, and that was really
difficult. I wasn’t sure what to buy or even how to put
it on correctly so that I didn’t look like a guy in drag,
not to mention the cost of good makeup. <br><br>
Our goal was to go out and stay under the radar as just two
middle aged ladies having a night out on the town. Michelle
gave me some advice on what to buy and offered to help me apply
the make-up as well as helping me get dressed. Well the day
finally came when I had all of my new outfits and accessories
and I was ready to see how much sexier I could become. I called
Michelle and he excitedly invited me over, but asked me
to wait about a half-hour before coming over so she could
get ready for me. I arrived with my suitcase in hand and Michelle
met me at the door dressed in a sexy long black gown with a
slit all the way up the center that left little to the imagination.
<br><br>
Her lipstick covered lips were moist and her long stocking
covered legs looked so inviting. We immediately shared
a deep French kiss and Michelle instantly started stroking
my hard throbbing, oozing clit. She wanted to kneel in front
of me and suck all of my manhood down her greedy throat, but
I was eager to get dressed and see if I could look as good as
she was after getting dressed. I had already showered and
cleaned myself out before cumming over. She dragged me
into her bedroom and pushed me back onto the bed. She slowly
removed my shirt, sucking on my nipples the whole time.
Next came the trousers, then she slid of my panties down,
and started stroking my hard shaft and flicking her tongue
deliciously across the head of my clit. The first items
were the lacy stockings. She slowly rolled them up to my
firm thighs, caressing my legs the entire time. When she
arrived at my hard shaft she gently licked the tip with her
tongue. I instantly became rock hard. Michelle then had
me stand and slid on a pair of my new red silk panties and the
feeling was superb. She then had me pull the corset up and
over my hips and then laced it up tightly from behind. I can’t
describe the erotic feelings I had at that moment. <br><br>
Next she strapped on my high heels and told me to get up and
walk around to see if I could walk all right in them. Not surprising,
I easily made my way around the bed and looked at myself in a full length
mirror. From the neck down I looked And felt like a pretty,
very sexy woman with my breasts being pushed up and in forming
very sexy cleavage in that corset. Michelle complimented
me on how sexy and inviting I already looked. <br><br>
She then sat me down on a chair in front of a mirror and started
to apply my make-up. All that time I was excited being in
the same room with her and my hand found the slit in her dress and I
started stroking her already firm clit. She reacted by
kissing me deeply and then pushing my hand away and saying
“Soon my darling”. She applied light foundation,
eye shadow, eyeliner, and powdered my nose and cheeks,
as well as applying the dark red lipstick I had purchased.
She then helped me to put the auburn wig, adjusted and brushed it into place. When I looked in
the mirror I no longer saw a cute man, but a very passable
and sexy woman. The finishing touches were the earrings
and the choker and my new look was complete. I loved what
I saw and I could tell Michelle did as well. We started kissing again and both of our hands started stroking
each others hard shafts. Michelle took some pictures of
me, and I of her. I couldn’t believe it was me in the pictures.
<br><br>
Then she told me she was going to video tape our activities
and that excited me as well. After setting up the video camera
Michelle commenced to perform a seductive dance slowly
removing some of her clothes. When she was down to her stockings
and a pair of skimpy pink silk panties, (that incidentally
was bulging from her hard clit) she came over and lay down
next to me. I quickly started stroking her wonderful silky
legs moving my fingers closer and closer to her throbbing
hard on. I stroked her through her silk panties and she moaned
softly. I slowly licked my way up her leg and planted a wet
lipstick covered kiss on her panties. Her pre-cum made
the silk panties wet and I encircled her still covered clit
with my lips. She started moaning louder and put her hands
on my head and pushed her crotch up against my lips. I almost
tore her panties off in my eagerness to taste her hot shaft.
She wrapped one of her legs over my shoulders as I slowly
licked up and down on her hard glistening shaft. I wrapped
my lips around the head of her clit and slowly flicked my
tongue into her cum hole, tasting her pre-cum and wanting
more. I opened my lips wider and sucked more of her shaft
into my wet mouth. The taste of her clit was very exciting
and the heat from her body was getting me turned on equally.
I slid further and further down her shaft, but then I started
to choke. She said “Relax your throat, take it slowly,
and you’ll be able to take it all”. As excited as I was
it was tough to relax, but I finally did, and she slid further
and further down until I could feel her deep in my throat.
My first deep throat!! I was totally engrossed in my excitement
and her balls were now against my chin and her shaved groin
was against my face. I started to pull out a little and she
attempted to keep my head in place, but when I slid my lips
back down her shaft she knew what I wanted. Soon I was rapidly
moving my head up and down on her shaft and she was moaning
louder and louder. I was eager to taste her cum and I slowly
moved my index finger between her ass cheeks looking for
her nether hole. As soon as I found it and slowly started
probing it, her moans became louder and louder. I wet my
finger with some saliva and slowly slid my finger into her
ass. She came almost instantly! Her hot cum was spewing
down my throat and I felt like I was drowning in it. What a
way to go! As she softened between my lips she reluctantly
withdrew and pulled my face up to her and we kissed long and
deep. <br><br>
She now pushed me back on the bed and started stroking my
legs and thighs. She told me how much she loved the feel of
silk stockings under her fingers as she slowly moved her
fingers to my hard clit. She didn’t waste any time and
she quickly slid off my panties. Her fingers wrapped around
my hard shaft and she started stroking me like there was
no tomorrow. She placed the head of my clit in front of her
lips and slowly twirled her tongue around the knob. She
took my shaft deep into her mouth and started sliding up
and down. She stopped for a moment and reached on a nightstand
for something and the next thing I know I feel a wet slippery
finger exploring my ass cheeks. She found my pussy hole
and slowly, ever so slowly, inserted one of her fingers.
There was a little tightness but little pain and that was
soon washed away with the delightful feelings she was providing.
Soon her finger was stroking in and out and my clit was getting
harder and harder in her mouth. I reached down to touch her
shaft and found it to be getting harder and harder as well.
Her single finger was soon joined by another and I could
feel my hole opening up. She kept them there up for some time---sucking
my clit and probing my ass. Then she said “I want us to become
one.” I knew what she wanted and although I was apprehensive because she wasn’t using a condom, I was
also excited by the feelings her fingers were stirring
in my ass/pussy. She slid away, had me hold my knees up to
my chest, exposing my pink hole to her lustful eyes. She
slowly edged closer and closer to my pulsing pussy hole.
She slicked up my ass/pussy with more and more lubricant
and slowly pushed the head of her cock against my hole. She
was average in length but a lot wider than anyone I had ever
seen before. I just knew it was going to hurt, but it didn’t.
She was gentle with me and she slowly entered my pussy letting
me adjust to her thickness. It took about ten minutes but
I soon felt her cock buried deep inside me. She then started
to slowly move in and out of me and the sensations were unbelievable.
<br><br>
She grabbed my hard clit and started sliding faster and
harder into my ass-pussy. I thought I had died and gone to
heaven. She was pumping me hard and filling me up with every
stroke and it wasn’t too long before I felt her clit get
even harder, then she was emptying her sperm into my ass-pussy,
at that point I lost all control and moaned make a baby in
me Michelle, please! The warmth and wetness were incredible.
She continued stroking in and out of me until her softened clit
slid out. <br><br>
I had just had my first one on one crossdressing experiences,
given my best deep throat blowjob and been fucked by a TG
for the first time. All in the same afternoon! Could anything
be more exciting?? <br><br>
We eventually moved together into my home which was much
larger than hers where we lived together for 4 years. Michelle/Mike
is still a very large part of my life even though we now live
in separate cities. I still watch some of the videos of her
and I from those wonderful times a few years ago. I am still
searching for someone like her to fill the void she left
when she moved out of my home. Rhonda

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