My first time with a man

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My first time with a man
I had been dressing privately for a number of years and never
been with anyone while dressed up. That is, until I discovered
this support group for other CD/TV and TS girls. I joined
the group, which held meetings once a month about 40 miles
from where I lived. I quickly made some friends and after
the first meeting Emily asked if I wanted to go to the local
gay bar and hang out. I had never been to a gay bar before,
or even out dressed other than the meeting site. There were
about 12-15 of us “girls” at the bar and we had
taken over 2 or 3 tables and just talked and got acquainted.
I quickly became friends with Terri, and we always talked
at the meetings. One night she asked if I wanted to come back
to her room at a local motel, and to my surprise I did. I was
shocked when she kissed me as we sat on the bed, I had played
with a guy once in high school, just mutual masturbation,
but had never kissed another person of the same sex before.
Anyway, she introduced me into the bisex lifestyle that
night and I found it to be amazingly erotic and sensual.
But Im getting ahead of myself here, this story is about
meeting a guy, not another girl.

About 2 months later, I was back at the bar with all the girls,
just hanging out. I was dressed to the nines as usual, I wore
a tight pink sweater that accented my 38 D silicone falsies,
a tight black mini skirt, black thigh high stockings with
lace at the top, a red garter belt, and pink lacy bra and matching
thong, along with my 4″ open toe pumps. My makeup looked
great also, with false eyelashes and of course bright red
lipstick. All of this over a completely shaved body. I also
wore my long blonde wig, which was a favorite of mine. A splash
of femmy perfume completed me. And if I could, I would’ve
picked myself up. I was feeling so very feminine.

Terri wasn’t there this month as she had to be out of
town, but I was well liked by everyone and just hung out with
everyone and loved sharing girl talk. We were taking turns
buying drinks and when it came my turn to buy, I got up and
tugged at my tight mini skirt so as to not show my lacy stocking
tops, walked up to the bar and hearing my heels click on the
hardwood floor was a turn on. I stood at the bar and tried
to get the bartenders attention in my most feminine voice,
which doesnt quite cut it. Just then I felt a hand on the back
of my waist, just barely above my ass and turned to see a nice
looking gentleman standing beside me.

He said his name was Jim and I gave him my long nailed hand
and said, “I’m Lisa”. “So nice to
meet you Lisa, can I buy you a drink?” I explained that
I was buying a round for my friends, and he offered to buy
the round. I accepted and he helped me deliver the drinks
to the table, just as a slow song was being played by the DJ.
I was about to sit down, when Jim put his hand around my waist
and asked me to dance. I grabbed his hand and we walked to
the dance floor. It felt so great to feel his arms wrapped
around me, holding me tight. I stand 6′ tall in heels
and he was taller than me, made me feel so much more like a
woman. I felt so at ease as he pressed tightly against me,
with his hands cupping my ass, feeling his manhood press
against my tummy. I wanted to drop to my knees in front of
him right there on the dance floor. I wanted a real man that
night, a masculine man to make me feel like the woman I wished
I was. Then he kissed my neck and told me how incredibly sexy
I looked and how glad he was that I was wrapped in his arms.
I replied with, “what a wonderful thing to say”,
as I looked into his eyes and smiled and then he kissed me,
his tongue finding mine and swirling around in my mouth.

Jim suggested we get out of there and I was more than happy
to agree. I explained that I lived 40 miles away and had a
wife at home so that wasnt an option. He said he lived alone,
about 10 miles from the club. I said goodbye to the girls,
who wished me a good night and walked arm in arm with Jim to
my car, knowing it would be a great night. Jim kissed me at
my car and told me to follow him. My clitty was getting hard
as I drove, knowing the night ahead would be awesome.

We arrived at Jim’s apartment and walked into his home
with his hand planted firmly on my ass. He kicked off his
shoes, turned the fireplace on and told me to make myself
comfortable. I asked where the powder room was, and I excused
myself to freshen up, applying more lipstick and checking
myself out. I returned and Jim was sitting on the couch with
2 glasses of wine. He caressed my legs and up the inside of
my skirt as I sat beside him. Then he kissed me as he explored
up my skirt, finding my lacy thong and my now hard clit. I
reached over and squeezed his bulge and discovered he was
equally as hard, and from what I could determine bigger
than me. Much bigger. We made out like teenagers there on
the couch and I fumbled as I tried to undress him. His chest
was hairy and I ran my long fingernails thru his hair, and
then undid his jeans. I slid my hand inside his jeans and
was pleasantly surprised to feel his hard cock, which had
to be close to 9 inches, not too thick, but not thin either.
I ever so gently slid my hand up and down his shaft with a light
feather touch, this made him moan loudly, which only encouraged
me more. He was so much bigger and harder than my friend Terri,
and I wanted to taste him as I had done with Terri just twice
before. I looked into his eyes as I leaned over and my lips
met the tip of his cock. I heard him moan as I licked the tip
and was rewarded with a sweet taste of pre cum. “Oh,
Lisa, that feels so good” he said. His fingers were
in my hair as I parted my lips and let his cock slide into my
warm, waiting mouth. My tongue was pressed firmly against
his shaft as I slowly took more and more of his cock into my
mouth until I was about an inch from the base. His manly aroma
wafted into my head and I knew then and there that this was
the person I was meant to be. He put his hands on my head and
began thrusting upwards into my mouth. “oh yes, suck
my cock Lisa”. Feeling him fuck my mouth and hearing
him moan and talk to me only turned me on more and my hard clitty
was now dripping pre cum on its own. I continued to stroke
his cock with my bright red lips as I cupped and teased his
balls. I had never tasted Terri’s cum, but I really
wanted it from Jim. After a few minutes of enjoying his cock,
his body began to tighten up, his cock was pulsating on my
tongue, he was grunting and I knew I had brought him to the
point of no return. And then it happened, he exploded with
what seemed like a gusher of warm creamy man cum into my mouth
and down my throat. I squeezed his balls gently wanting
it all. Some of it dripped from the corner of my mouth and
I quickly sucked it back in, enjoying the taste and texture
of this hot man. When I had swallowed it all and felt him go
limp I came off and sat up and smiled at him. Jim smiled back
at me and placed a hand behind my neck, pulled me to him and
kissed me deeply and passionately. Then he went down on
me and returned the favor until I too was drained and limp.

We sat there and talked into the wee hours of the morning.
I explained how my marriage was stale, how my wife knew I
dressed, but she hated me doing it, and how I was still new
to the bisexual lifestyle with Terri, and my wife was unaware
of that about me, but seeing as the marriage was practically
over, it didnt matter. He said he was divorced and bisexual,
had always been attracted to girls like me and how its been
the best sex of his life. I said I would have to agree, so far.
He asked if I like to bottom, and I explained that I never
have, but I feel very comfortable with you and would like
to explore. Then he asked me if I would like to spend the night
with him. I agreed and went to the car to get my boy clothes
for when I leave the next day. I went back in, asked to use
his phone (this was before cell phones) and called my wife,
told her I wouldnt be home that night. Her response was to
not come home at all, that she had met a guy while out at the
club with her girlfriends. I then told her I had done the
same and he is great. I explained I would be back the next
day for my things. I asked Jim if I could stay with him for
a couple of days just until I find an apartment of my own.
He said that would be just fine, and we climbed into bed together,
where he proceeded to introduce me to anal sex and fucked
my brains out.

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