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Transgender & Crossdressers
First Times

FIRST TIMES
STORY INFO
His first time with a man.
2.3k words
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MichelleWhoIs
MichelleWhoIs
10 Stories47 Followers

A little background is in order. During my teen years, I became involved
with a woman that helped me discover the pleasures of my female side.
Sue helped me to dress and act in a very feminine manner. We were almost
like sisters in the way we became so close.

She would sometimes describe how good her boyfriend would make her feel
when they would make love. She seemed to think it was funny seeing me
squirm when she would get a little too graphic. I know she was only
giving me a playful hard time.

She did get me to admit that I was just a little curious about what it
would be like to be with a man. Each time she brought up the subject, I
would say "No Way". I couldn't be with a man until I felt more
comfortable being a woman. After she married and moved away, I wasn't
able to dress as often.

I purged myself of all my clothes and jumped into what I hoped would be
manhood. Four months after she left, I joined the military.

For several years after I joined, I act like Joe Macho. I would do just
about anything trying to prove my manhood. But then it happened, I was
in a mall one day with some friends. The wife was in the lingerie
section of the Ladies Department. Her husband and I were like all guys,
in that situation, trying hard to not be there.

As I made my way past several racks of bra and pantie sets, one set in
particular caught my eye. It was a pink lace baby doll set that reminded
me of the first set of lingerie I had tried on.

The old urges to be a woman came flooding back. I tried to convince
myself that it wasn't going to ever happen again. I even had my reason
why I could never do it. I was in the military. If caught, I would be
thrown out with the black mark on my discharge papers. Worst case would
be if some of the guys in the barracks found out. I would be the subject
of a blanket party or worse.

The more conflict I had within me, the stronger the urges got. I even
tried writing to Sue about what was going on with myself. After 3 weeks
and no letter from Sue, my will power caved and I devised a plan to at
least try dressing.

I went back to the mall where I purchased several pairs of panties and
bras that I kept stashed in my locker. I would dress and masterbate,
remembering some of the fantasies I used to have after listening to Sue.
I have to admit, a couple of times my mind would wonder back to her
suggestion of being with a man.

Jim, my roommate at the time was a party animal that would come back to
the room and pass out. After finding him several times on the floor in
the morning, I would make sure Jim made it to the bed. I would help get
him undressed if he couldn't do it himself and set up the trashcan next
to the bed. In the mornings, I would make sure he got up, had his OJ
ready after his shower and made sure he got to work on time.

The first time I did that, I laughed at him saying how easy it was for
me to get a big guy like him into bed and out of his pants. He was 6'1"
and 200 lbs with muscles everywhere. I was still 5'8" and 157 lbs with
no real muscle mass to speak of.

One Sunday night, he came back early. When I heard the key in the door I
threw on my bathrobe. My heart was pounding because I still had my bra
and panties on. As was becoming the custom, Jim would attempt to tell me
about his latest conquest as I helped him get undressed.

He was lying on his back and as I bent over getting his shoes off, he
started running his hand over the backside of my thigh. I couldn't
believe how good it felt but my mind was screaming to run before his
hand reached the panties. I slapped his hand and in my best feminine
voice I said "No fair getting fresh when you're drunk!"

He started talking about how much I resembled a girl and how soft and
smooth my legs felt. I never really had much hair growing on my legs so
I would just shave them. He started talking about how I could give him a
blowjob to help him get to sleep. I jokingly said, "I would rather suck
you off when you're sober so we could both enjoy it". As he drifted off
to sleep he made a comment that I would make some guy a wonderful wife
one day.

As I pulled his pants off, I noticed that he had a hard on poking out of
his boxers. I was amazed at how big Jim was. His cock was at least 7"
and at least 3 inches thick. I wanted to touch it but was afraid that if
I did he would wake up. I got in my bed but I couldn't take my eyes off
his cock.

I slipped my hand in my panties and slowly stroked myself to orgasm. I
exploded faster and harder than I could ever remember. I had to push my
face into the pillow to keep from moaning out loud. I withdrew my hand
and licked the cum from my fingers. I was amazed at how it tasted.

After I was sure he was asleep, I got out of bed, cleaned myself up and
got changed. I had a little trouble getting to sleep with all the
thoughts that I was having. I finally drifted off thinking about his big
cock and what it might be like to have Jim make love to me.

The next morning, things were not normal. It was a little easier than
normal to wake him up. He jumped up and headed for the shower. Normally
he would bring fresh pair of boxers with him to the shower but this
morning he didn't. He came back in the room and dropped his towel with
him facing me. I know he saw me glance down to his cock. He dressed and
before I could give him his OJ, he left. I just shrugged it off as being
a fluke.

He came back from work and took off his uniform. He was sitting in the
chair with just his boxers on. We started talking and I was having
trouble not taking quick peeks at his crotch. He started thanking me for
taking care of him whenever he came home drunk. He also told me that he
hoped that I didn't take offense to his comment about being a girl, the
blowjob and being a good wife.

I laughed it off saying that I didn't mind because I knew he was drunk.
It didn't dawn on me that he might not have been as drunk as I thought
he was since normally he didn't remember much the next day.

The next weekend was a long weekend. He was supposed to be gone till
Monday. I didn't see him after work Friday so I figured he left for the
weekend. Saturday morning, I went to the mall and found a very pretty
lavender and lace baby doll set. I figured that with the long weekend I
could wear it to bed and not have to worry about Jim being home.

On Saturday evening, I dressed in my new baby doll outfit, got in bed
and jacked off thinking about Jim. I came in my hand and I licked it
clean. I was starting to acquire a real taste for cum. Since I didn't
think he would be back, I fell asleep in my nightie. I fell into a deep
sleep dreaming about Jim and what our life would be if we were married.

At around 1 AM, I started getting the sensation of someone playing with
my breasts. At first I thought it was a dream but I realized that Jim
was whispering in my ear that I looked pretty in my nightie. He started
kissing my neck and moving next to me in bed. He was naked and I could
feel his cock again my hip.

I froze in fear but he assured me that I had nothing to worry about. I
was so afraid that he would tell the Shirt and my life would be ruined.
He told me how he remembered what I had said the previous weekend and
was testing the waters. He told me that he found my locker unlocked and
discovered my little stash of undies. He also told me that he watched me
get undressed last Sunday.

He gently turned my face to his and he softly kissed me on the lips. Jim
told me that he hadn't had anything to drink that day so he was fully
aware of what he was doing. I looked into his eyes and saw something
that told me to not to be afraid. He wanted me as his woman. I put my
arms around his neck and pulled him closer. The kissing became so
passionate that I felt dizzy. I held on to him so tight.

I relaxed my hold on him and slipped my arm down between us. I wrapped
my fingers around his cock and started slowly stroking him. He kissed
his way down my neck and slowly worked his way to my nipples. He started
slowly running his tongue around the nipple. It felt like a surge of
electricity pulsed through my body. He slid his hand down over my tummy
and I slightly spread my legs to allow him access. He slowly started
stroking me through my panties.

I pushed him on his back and slowly started kissing my way down his
torso. I kissed the head of his cock and tasted his pre cum. I slowly
opened my mouth and he pushed the head in. He told me to run my tongue
around the head and I did. He pushed himself in further and I reached up
and started playing with his sac. He started pumping in and out as he
was playing with my nipples. His cock reached the back of my throat and
he told me to relax when I started to gag. Soon I was able to take all
of his 7 inches without gagging.