Mathew Mats Rogers SeriesChapter 3 Back on the Road Again
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The Road To Today free porn video
I was from a small town in Vermont. I went to a small liberal arts
college in Maine. I was athletic, slim, but all guy, with one small
exception. I loved to wear ladies panties. I had even tried make up and
a wig once or twice. The wigs were Halloween wigs and the make up, left
over stuff in the family bathroom. Other than that I just figured I was
a normal over achieving heterosexual, who took on far too many
commitments and far too many problems belonging to my family. You may
have one of these in your family, but I was the person everyone came
too with their crisis and I mean everyone. You develop your inner self
in isolation when you play that role and when you are from a small town
and a big family with lots of problems, it is a role you learn to hate.
Here I found myself, 24 years old, in NYC for 4 months, on assignment
for the accounting firm I worked for. I was alone. No one from my town
or for that matter my college was in NYC. I worked long hours and spent
lots of time exploring all sorts of bars and clubs. I found myself
drawn to the time square books stores, the J channel and the personal
ads in the Village Voice. They fascinated me, especially the
transvestite/she male advertisements. I found myself fantasizing non
stop about dressing and being with another transvestite. It began to
consume me. One issue of the Village Voice contained an ad for a party
on the back page. "Party for Transvestites and their Admirers,
Wednesdays. For details call ..." To date my fantasies were just that,
ideas and my club observations, just that as well, observations. I was
shocked at myself when I called. I was soon invited to attend a party,
somewhere down in Chelsea. I found the idea intoxicating. It stirred my
mind into a hazy dream world of meeting a young, trim, fit and clean
girl/boy my age to explore this fantasy.
The day of the party was a busy day on the project. The party was early
in evening, over by 9:00. I ended up working until 7:00, despite my
best efforts. I ran all the way to the apartment. I showered and found
myself shaving, my face extra fine. I then shaved my legs and then my
arm pits and even, my pubic area. I did it quickly, as if I was scared
if I stopped, I would stop the whole thing. I put on a new pair of
panties, blue second skin satin from Victoria Secrets. I had bought
them the weekend before and I loved the way they felt. I put on a pair
of white light cotton pants which fit tightly, knowing the panties
would show through. I couldn't help myself. I was intoxicated by the
idea of going to this party. I wore a long blue satin shirt that when
untucked covered my ass. I never would have worn this type of clothing
at home. It was iffeminent. I did not know anyone in the building I was
staying in but hoped no one would see me. This was not my image. I
snuck out with a light jacket and my new shoulder length hair in it's a
pony tail.
I arrived by taxi, because I was late. I jumped out on the corner of a
cross Street and stopped in a bar order a quick double shot of Vodka.
Downing that I ordered a second and then, quickly left. I found the
building. The entrance was through a mettle door with a clouded window.
Inside I found myself in a short narrow hallway, with various mail
boxes and buzzers for the apartments in the building on my right. The
elevator for the building was at the end of the entrance hall. The
lighting was bright. I was nervous. For the first time I hesitated,
while looking for Ms. Sinclair's buzzer, Apartment 4D. Before I could
push it the elevator opened. It was 8:15.
Out from the elevator walked three transvestites. They were all
incredibly convincing as women, but I knew. I felt my heart race and my
now constant hard on, tighten. They were happy and drunk, I think. A
tall thin Hispanic girl, in bright red skin tight shiny leggings was in
front. She had a black corset top and beautiful skin. To her left stood
a white girl, wearing a red vinyl or patent leather mini skirt, a white
silk blouse, which contrasted her olive skin and jet black shoulder
length hair about my new hair length. Finally there was a small
Pilipino looking girl in leather pants and a white lace corset. It was
funny but right away, I wished I could be part of the group. My
fantasies raged in that first instant and then, I got really nervous
and embarrassed, as I always did around woman.
They laughed when they saw me and the white girl whistled at me. She
was hot and it made me almost wiggle. I asked in a horse voice if they
had come from the Sinclair party. I wanted to be cool so badly and let
them know I was there to meet or be with transvestites. I didn't know
how to do it of course. The effort was not smooth. They laughed at me
and hung on each other. Then, the white girl, as she passed me nodding,
leaned over and kissed me. I let her do it. I felt like I would
explode. She took my right hand with both of her hands and placed it on
her nylon covered leg. She then quickly slid it up under her crotch,
letting me feel a small but distinct and hard bulge in her panties. I
literally gasped. She laughed.
She broke away from me and said, "You go see Ms. Sinclair, she will
help you out and she will like you too. When you are done, however,
come find us at Sally's on 42nd in Time Square. We will be there until
closing probably. She left. My back was hard against the mail boxes. My
mind was buzzing. No big picture of life, I just wanted to find this
creature. I wanted to act out my newly found fantasies with her. I
wanted to have her hands run over my ass while I was wearing a skirt
like she was. I wanted to feel her cock again and explore it with my
mouth, to pleasure her, as a girl.
I did what she said. I pushed the button for 4D. A husky but iffeminent
voice came over the intercom inviting me up. For the first time I
noticed a small camera. The apartments must be able to see you, when
you buzz them I thought. I pushed 4. I had no idea what to expect but I
knew at this point I was in for a wild night.
Ms. Sinclair was a middle aged transvestite. She was not sexy like the
girls who had left. She was on the heavy side and wore a tight gold
blouse showing off large breast. She had a white secretary type skirt
and bright red shoes. As she opened the door she was laughing into a
cell phone. She agreed with someone about something, smiled at me in a
devilish way and hung up the phone. I got an unexpected hug and a
squeeze on the ass. The room had 4 or 5 people in it. All but one man
were in drag. The transvestites were all older than the girls who had
just left. There was a tall black TV with a red sequin dress and big
red lips, topped off by huge eyelashes and a large round ass. Two other
middle aged and not overly convincing transvestites sat on the couch.
Suddenly the door to another room opened. Out stepped a white man, with
his fly undone and a shit eating grin on his face. He was followed by a
thin dark skinned TV wearing a black shiny cat suit, with a whip in one
hand. She made me swallow hard.
Ms Sinclair talked with me and the others a bit. I could feel my vodka
shots hit home, topped off by a vodka tonic somebody handed me. Soon I
was explaining my fantasy. I wanted to learn to dress and wanted to
meet other transvestites. No I had no clothing of my own. Ms. Sinclair
came in big on this point. She worked at a TV Boutique and had lots of
clothing that would drop men in their tracks for me. The deal was I had
to agree to let them take a few photos of me, dressed of course. No one
would know. I was way too far out at this point to flinch at this idea.
Of course I would do that. How incredibly generous of her.
I followed Ms. Sinclair into a large bathroom/dressing room. Behind her
came the tall think black TV in the cat suit. I swallowed hard again.
They had my pants off in no time and laughed to see my panties and my
small but hard 51/2 inch cock outlined in blue satin. The black TV ran
her hand across the outline of my pennies. It jumped and a wet spot
appeared through the panties. I was drooling.
When they noticed my shaving job, the two ladies became even more
enthusiastic about my transformation. No wig would be necessary; I had
such a light beard, only a light base would be needed. Ms. Sinclair
worked on my face and hair. Sheneka, the black TV began to bring
clothing in. Soon I was standing fully made up by the two of them, in a
black and red corset, which somewhere I knew was worth a lot of money.
Crotchless panties, for now. The gaff would come latter they told me. A
pair of fishnet nylons showing off my hairless legs and a black vinyl
mini skirt. My penis was dripping. I was staring at myself in the
mirror and just so in awe of it all. A flash startled me. Ms. Sinclair
had snapped a picture of me with my cock out, twirling around looking
at myself. A second picture followed and then Sheneka moved in. She
took her smooth hand and caressed my cock. She rubbed my ass. More
pictures. She knelled down and kissed my legs and my stomach. I
convulsed, I almost came without being touched. She pinched my cock
hard. It settled down. She licked her lips, more pictures followed. She
took me in her mouth. I arched my back. Her hands were on my ass and
her finger pressing my asshole. I came, like I had never cum before.
Huge jets of cum shot across the room. They landed in Sheneka hair and
on her outfit. More flashes. I collapsed into a pile of clothing
slipping in my new shoes.
They helped me clean up and put on the skirt. I walked out. The two
non-TV men in the room clapped and looked way too interested in me. I
had no interest in middle aged fat white guys. I wanted to find the she
males from the front hall. I told Ms. Sinclair about wanting to go out
to Sally's to find the other girls who had asked me to meet them. She
agreed to let me go but that if I was going dressed Sheneka would have
to take me, to make sure I made it there OK. I left with her clothing,
never thinking about the clothing I had worn there.
The cab ride was short. Sheneka let me stroke her cock through her
outfit. I asked her about giving head. She laughed and said in good
time. She told me to watch my teeth and advised me to work from the
start on relaxing my throat. I was so ready to find the girls. When we
arrived at the bar, I was let in free. I did not know what had happened
to my wallet or money. Sheneka told me I would not need to worry about
money dressed like I was. I would have plenty if I wanted it at the end
of the night. I was not sure what she meant but, it turned me on to
think I might turn a trick as a TV, just no middle aged fat white guys.
We found the girls I had seen earlier. Missy was the girl who had
kissed me. She came up immediately and kissed me again, winking at me
and saying I told you Ms. Sinclair would take care of you. Sheneka
hugged Missy and introduced me to the other two girls, Tanya was the
Pilipino girl and Hallie was the tall Hispanic girl. They all had to be
about my age I thought. Each of them hugged me and ran their hands
across my ass. I swear I almost came again, despite the gaff now in
place.
The girls had men all around them. Business men, middle aged white and
black men dressed nicely and some small Japanese men in suits. I was
introduced around as Michelle, a derivative of my real name. A Japanese
man bought me a drink and Sheneka told me I should go talk to him for a
bit. I did, looking over his shoulder at Missy the whole time. He
rubbed his hands on my leg and that made me tingle. He asked me if I
would go back to a booth with him for private chat. I said I would. He
led me back. As I walked by Missy, she said, make sure you get $50 from
him for this. I was into it. I was going to do this, I decided right
there. I walked back with the Japanese man. I whispered to him in my
best girl voice that I would need $50. He peeled off $100 and said,
that was not enough for me. He then pulled me into a small round both
in the back of the already dark room. He ran his hands up the inside of
my leg. With surprising dexterity, he found the tie to the gaff and
released it. I smiled thinking of all the times trying to get girls
brassieres off over the years.
He fondled my hard cock and then he went down on me right there in the
bar. I did not last long. His hands on my ass and his head in my lap
were too much. I came for the second time that night and my cock stayed
hard as a rock. He sat back up and kissed me on the lips. I tasted my
own cum. It did not gross me out a bit. I was shocked.
He took my hand and ran it across his silky suit pants. I felt his
bulge. I did not need further prodding; I ran my hands from the head to
the base and back. I then unzipped his fly, much easier than a
brassier. I was so surprised how smooth another man's cock is. It was
like feeling silk or satin. I took the same position he had with me.
Missy came up, however and lean over speaking into my ear. "No matter
how hot you get, you make him wear this. She stuck a condom in my
hand." It was a sobering moment. I realized what I was about to do. No
condom. How stupid. I put it on him quickly and I am not sure he even
knew. I then began my first blow job I ever gave. I gagged a bit. No
teeth though, I was working hard when I felt him tense, he jerked a bit
and I could feel the warmth of his semen through the condom. I felt
proud and once again horny. I had never come more than once in a night.
I was ready to go again.
The night passed quickly after that. I did not meet any more guys, but
I watched Missy go off with a young white man who came in. He looked to
be barely in college and very clean cut. I wondered if he was secretly
hoping he was in my shoes.
Around 1:00 a.m., early for NYC, Missy and I began to chat alone. I
told her what a mind blowing night I was having. She squeezed my hand.
She had been dressing for about a year. She was a senior at NYU. She
was in drama and was never going back to her little town in Texas where
she was from. He parents did not know she was a TV or anything but a
good Texas Republican. I confided that this was all new to me. Two
months ago, I had been in Burlington Vermont, a definite heterosexual.
She said to take it easy and warned me I would go through some rough
times dealing with what had happened. She said she would love to help
me through it though and within the hour we were fast friends.
I learned she had gone to a Sinclair party much like I. So had Hallie
and Tanya. It is how they all had become friends. They met on their own
a lot but still went to Ms. Sinclair's parties because Ms. Sinclair
loved to look at them. Missy explained that Ms. Sinclair and Sheneka
both got off on watching the innocent boy become hot she males. They
were like a team facilitating the transitions for anyone they could.
We talked to Tanya and Hallie and decided all to go back to Hallie's
apartment for the rest of the night. As we left, Missy ran her hands
over my ass again. I was latterly falling for this she male. In the
cab, we took turns trying to feel each others cocks without the cab
driver knowing what we were doing. It was such a weird but wild ride.
We walked into a small but clean apartment on the upper west side.
Hallie told us her neighbors knew about her and left her alone.
The night was awesome. I was in 7th grade again, at my first house
party, making out with Missy in the corner and holding hands. Hallie
undressed in front of us, down to her panties and I found she had real
breast. Tanya followed and she too had real breast. They looked at each
other and then kissed. In front of me I watched two beautiful TV's
going at it. Missy pulled my skirt off and then my shirt. I did the
same to her. We rolled about on the leather couch. The room was full of
sex.
I looked up from time to time, finally seeing what I found incredibly
exciting. Hallie was fucking Tanya from behind and caressing Tanya's
cock at the same time. Missy and I stopped our explorations and
watched. The two collapsed in a pool of sperm and sweat. I leaned over
and said to Missy, I wanted to do that to her sometime soon. She would
not let me this first night, saying it was a big step. She then leaned
down and took my cock in her mouth, sucking me to my third orgasm of
the night in about 3 seconds. I kissed her and ran my hands across her
ass in appreciation. I rubbed my body against hers and began to kiss my
way down her chest. I stopped on each nipple and while licking and
sucking began to explore the rim of her anus. I then moved my mouth
down to her lower stomach, a rock hard one at that. Then to her cock.
It was so nice with no condom. So smooth and silky. I licked and sucked
it, taking the whole thing in my mouth. She was like me, about 51/2
inches. It fit in my mouth and down my throat. My finger penetrated her
anus just slightly and before I could react she was cuming in my mouth.
I swallowed all I could and continued to lick and suck as her spasms
weakened.
She then kissed me and took me into her arms. I fell asleep like that.
My first night as a she male. We still live in NYC together. I have
small breast and beautiful long black hair today. Missy gave me
collagen lip implants last year for Christmas. She also saved and got
some great breast implants. No one today would ever know we were once
biologically men and in my case heterosexual (or so I thought). No one
suspects we are anything but hot lesbians. We both work in an S&M club
down on the east side and run a hotel booking business from the house.
We have continued to remain friends with Tanya and Hallie, both her
perform as female impersonators and work at a TV bar right above the
S&M bar Missy and I work at. This is, or was at the time it was first
written a true story. Sally's has moved. Ms Sinclair has left town.
But, life is good.
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