My story is about the start of my transition to a woman, and finding the perfect guy

This story started a couple of years ago, or should I
say it all started 40 years ago when I was young. It seems I have always enjoyed dressing in women’s
clothes. I have been a closet cross dresser for most of
my life, starting with dressing in my mother’s,
sister’s, aunts, friends, etc. underwear then my wife’s
and at any opportunity pinching other women’s underwear
when the opportunity arose, then wearing them under my
regular clothes. Recently I bought a video and a couple
of books on cross-dressing on how to buy clothes, apply
makeup, walk etc. These are my bible as how to act like
a woman.

A couple of years ago I started chatting with other
cross dressers on line and comparing stories and advice
with these guys out there in cyber space. I then joined
a men’s personals chat line and talked with a lot of
guys that were interested in meeting me so they could
see me dressed up. This was scary as no one had ever
seen me dressed in women’s clothes, until I met Jeff.

This is where my story begins:

I meet Jeff on Lavalife. We talked and exchanged
pictures for 2 months or so before we met. We talked
about what we liked, wanted, what we would do the first
time we met. It was very exciting fantasizing with each
other. He would send me pictures of himself nude and
with nice clothes, on he didn’t dress in women’s
clothes he just liked seeing other men dressed up.

I sent him pictures of me dressed in women’s clothes
that I had bought over the years, some with me in nice
underwear, and sexy tops and skirts. I had bought my
self a excellent pair of silicone breasts from an
online store a few months ago, that looked very real,
and by this time I had a not bad collection of clothes,
underwear and shoes.

The few months I talked with Jeff over the net we
became very comfortable with each other. I travel a lot
for my work so I arranged a trip close to the city that
he lived in and we made plans for an afternoon to meet
and get to know each other.

We met in a nice little bar not far from my suite
hotel. I was a little late getting there and when I
walked in their, were about 8 or 9 people around the
place having a drink. I looked around and spotted Jeff
immediately he looked just like his pictures he had
sent me. He is 63 years old 6’2″ about 250 pounds, not
real fat just nice and big a bit of a belly, and a he
is an extraordinarily fine looking man. He has salt and
pepper hair trimmed nice and neat bald on top with just
a wide fringe above his ears. In other words a very
nice looking man that keeps himself well kept. He was
dressed in a black suit, burgundy shirt and tie.

I walked over to him and said “hi Jeff I’m Richard.” We
shook hands and I sat down and ordered a drink. Jeff
already had one going so we started with some small
talk and we BS’ed for 3 or 4 drinks. Finally he said
“we should go to your room and talk, as he couldn’t
wait to see me get dressed up for him.” We finished our
drinks, I went up to the bar paid our tab and Jeff and
I left for my room.

It was busy out on the street and had started to rain
while we were in the bar. Jeff had his umbrella with
him so he put it up put his arm around my waist and
pulled me closer to him so we could share it. as we
walked back to my room he kept his arm around my waist
as we walked, this got my heart racing a bit as it was
extremely exhilarating to be walking down a busy street
being held by another man.

On the way to the hotel we stopped at a liquor store to
get a couple of bottles of wine, as we were looking at
the selection he put his arm around my waist again and
held me close to him while we discussed what we liked
to drink and selected 3 bottles. This was also
stimulating as I had never had another man be so
affectionate to me in public before, he also gave me a
kiss on the cheek when nobody was looking. We paid for
the wine and slowly walked to the hotel holding hands.

When we got to the room I poured us each a glass of
wine and we sat on the couch, making small talk. After
the first glass of wine I leaned over and kissed him on
the cheek, and said “I need a few minutes to go get
ready for you.” He said “hurry, I don’t know if I can
wait much longer.”

I got up and went into the bedroom and closed the door
so he couldn’t watch. I had put all my female underwear
on before I gone to meet Jeff. I had put on my open
butt garter belt and mauve coloured nylons, so all I
had to put on were my bra and silicone breasts, wig and
makeup. I had picked out a nice mauve coloured tight
fitting silk lace mini slip dress that I thought looked
pretty sexy, it came down to just above my knees and
hung off my shoulders exposing some of my chest and all
of my arms, I had gone out and bought it that morning
when I arrived in the city.

My wig which is a shoulder length dirty blonde and my
makeup took a little work to make me look pretty I put
on false eyelashes and delicate small clip on earrings.
After about 30 minutes Jeff knocked on the door and
asked if everything was ok, I replied, “Yes I just need
a few more minutes pour us another glass of wine and I
will be right out.”

I finished fixing myself up put on a pair of low healed
pump shoes and took a look at myself in the mirror and
was satisfied with my looks, before I had left home I
had shaved my entire body all except for a little patch
of closely trimmed hair above my genitals so my whole
body was smooth and felt so sexy with all the silk
clothing I had on. I had also been using a cream on my
entire body for a few months so it is smooth and soft.
I wanted to look and feel really sexy for Jeff so I
took a little more time to get ready then I thought it

I opened the door a crack and told Jeff to close his
eyes, I slowly walked out into the living room and
stood in front of him as sexy as I could. I had done a
lot of reading and studying on line to teach myself how
women walked, stood and acted. I told him to open his
eyes, I was totally petrified point as this was the
first time ever that anyone would see me dressed like a
woman in real life. My tummy was doing flip flops a
hundred miles an hour.

Jeff opened his eyes and just stared at me for what
seemed like hours but was really just a few seconds
then said “oh my, oh my your stunning.”

I leaned over and took his face in my hands and put my
lips on his and we kissed for the first time, we just
kissed with our lips for a minute or two and he slowly
stared working his tongue in my mouth. I put my hand on
his chest a started undoing his shirt buttons one by
one. After I had three or four undone I slipped my hand
onto his bare chest and massaged his hairy chest
running my fingers through his hair and kissing his
neck. We just cuddled and kissed each other for a long
time stopping to have a sip of wine once in awhile and
totally enjoying each others lips and bodies. He was
gently massaging my back and legs through my sexy

After a long time of kissing and licking his nipples
and chest, I took him by the hand pulled him up and led
him into the bedroom. I slowly started taking his shirt
off undid his belt and pants pulled his pants and
underwear down very slowly. When his manhood came into
view I couldn’t believe how beautiful it was. It was
wonderful undressing him and to be able to kiss and
touch his body. Jeff is a very sexy man, not fat just
nice and big, a little bit of a belly, and all hairy.

I was in total awe when I finally saw his member, it
was as hard as a rock about 8 inches long with a
magnificent head when I touched it was so soft and
silky-smooth, I slowly took it in my mouth just kissing
and licking his head and slowly working my way down
this beautiful shaft I took his big balls in my hand
and kissed them all over sucking them one at a time
gently into my mouth, then pushed him down onto the bed
all the while slowly kissed my way down his legs and
back up his body until I was laying on him kissing him
on the mouth again.

I could not believe my luck in finding a man that loved
the way I dressed for him and took pleasure in me and
my body a me kissing him all over his handsome body.

When I was laying on him he was massaging my body now
under my clothes and slowly kissing me on the neck and
shoulders. After a few minutes of this I said “let me
undress for you” he nodded and lay back with his hands
behind his head and watched.

I stood up and slowly pulled my mini slip over my head,
as close to a strip tease as I could, revelling my
garter nylons panties and bra filled breasts. He lay
watching me with his big beautiful manhood standing
straight up just inviting me to take care of it. I
slowly rolled my panties down my smooth legs, kicked
them off and swung my leg over him. I stopped and took
a jar of KY jelly from the night stand and rubbed it
all over his manhood and some on my bum hole then I sat
on his big thing and slowly guided it into my bum ever
so slowly as he was huge.

I gently pushing him into me until I had him completely
buried in me, I never felt so full in all my life. I
must have made love to him this way for 15, 20 or more
minutes I’m really not sure as the feeling was so
wonderful I lost all track of time. Jeff caressed and
touched me all over at least to places he could reach,
and then held me by the hips moving me back and forth
up and down until he came deep inside me. He then
pulled me down on top of him and held me tight kissing
me until his spasms stopped.

After a bit he gently rolled me over and kissed and
licked his way all over my smooth silky body until he
took my member in his mouth kissing and sucking on it
until I was ready to cum, then he stopped and turned me
over on my stomach and did the same to the back of my
body down to my feet and back up to my bottom where he
used his tongue to lick and make love to me with it.

When he rolled me over again and took my member back in
his mouth and sucked me to an orgasm that made me
almost faint with ecstasy, keeping me in his mouth
until I had emptied all of my cum in his mouth. I
pulled him up to me so we could snuggle and cuddle and
bask in the after glow of the best love making I had
ever experienced.

We lay in each others arms until I asked him if he need
another glass of wine and a snack. He said he would
love both. I got up put on a black baby doll thigh
length mesh nightie with an open front and low cut back
that I had also bought that morning, gave him a smile
and went out to the kitchen to make us a snack and get
some more wine. I had always wanted to be a complete
woman and doing this made me feel so sexy and feminine
and it made me horny as hell, to be looking after my
man in the bedroom.

I put every thing on a tray and went back to Jeff who
was sitting up in bed with the sheet covering him to
his waist and a smile on his face. I sat on the edge of
the bed and handed him a glass of wine then took a
cracker with cheese and put it in his mouth. We sat and
talked as I feed him cheese and crackers, strawberries
grapes while caressing his hairy chest. This was so
erotic to me that I was getting to know what a woman
would feel like.

After we had ate our fill and drank more wine I noticed
a little tent starting to grow under the sheet, so I
said “now its time for your desert” and pulled the
sheet down and gave him a blowjob sucking him until he
filled my mouth with his sweet cum I drank all of his
thick juice then licked him clean. I said “now sweet
man would you like to have a bath with me” He said ”
yes that would be great, but I better phone home and
tell my wife that I won’t be home tonight if that’s ok
with you.” “Oh yes” I whispered “please do, there is
nothing I want more then you to spend the night with me
if you can.”

I got up and went to the bathroom to start the bath as
he picked up his cell phone to make his call.

He came in the bathroom a few minutes later and said
“there was no one there but that he left a message that
he had been tied up at a meeting and that he was going
to get a room in town and would call in the morning.”

He helped me get out of my nightie, and gently helped
me take off my undergarments, and then we got into the
nice hot bath. We soaked for the longest time in the
bubbles, cuddling each other and soaping each other
just talking about things and sex and what was going to
happen after tomorrow morning when we had to go our
separate ways, we didn’t want to talk about this to
much as we were in our own little world at the moment.

We dried each other off, I put my falsies and bra back
on as he watched, then put my nightie back on but
nothing else as my legs were shaved then waxed the day
before so I was a smooth and velvety as any woman. We
went and got back into bed and kissed a snuggled until
Jeff put a couple of pillows under my bum to elevate my
bottom then he took the KY jelly and while on his knees
rubbed ,(so I could watch) it on his gorgeous man thing
then put some on his finger and slid it in my bum, he
gently crawled on top of me and kissed me deeply while
I guided him into me, he made love to me real slow and
gentle all the while kissing me and caressing my
breasts and belly, stroking my legs and inner thighs.
Making love to me this way allowed us to kiss each
other and for me to put my arms and legs around him and
experience what a woman would feel. We made love what
seemed like hours this way Jeff just going in and out
of me ever so slow and gentle until I could feel him
building up with desire then he started pumping me
faster and faster and more deliberate thrusts until he
exploded in me, which set me off on the most shattering
orgasm I ever experienced. We were both exhausted and
he lay on top of me while I hugged and held him and he
kissed me long and deep. I didn’t want him to get off
of me it felt so wonderful and I have never felt so

After we lay in each others arms having a sip of wine I
suggested we order a pizza or something as we would be
staying in for the rest of the night. He said “good
idea: so I phoned a local pizza place and ordered one.
They said it would be about 45 minutes so. We snuggled
and played lovers until the door bell rang, I hopped up
straitened my hair put on a bathrobe that was in the
closet and answered the door as a woman.

The pizza delivery guy was a young guy about 25 or so
handed me the pizza and said “that will be $32.50
ma’am.” I went and got the money from my wallet and
gave him a nice tip for calling me ma’am. I was quite
surprised that he didn’t look at me funny or anything.
I put the pizza on the counter in the kitchen and went
in to see if Jeff wanted to eat in bed again or eat out
in the living room.

He suggested that I hop back in bed and we eat later if
it was ok with me, I hopped right in and snuggled up
nice and close. We cuddled and snuggled for a while
then he snuggled up behind me and we drifted off to
sleep. I woke up a couple of times to hear him softly
snoring and backed up closer, in his sleep he would
hold me tighter. His body heat was very nice and felt
sooooo good I didn’t want it to ever come to an end.

I slept some more then had to go to the bathroom so I
carefully slid out form his embrace to go to the
bathroom, he quit snoring and was breathing heavy when
I left.

After going to the bathroom and fixing myself up I went
out to the kitchen for a piece of pizza as I was
starving from all our physical love making, and looked
at the clock it was 8:30 in the morning we had made
love and slept for 18 hours I could hardly believe it
had been that long.

I went back in the bedroom and quietly crawled back in
Jeff’s arms and snuggled my bum in to his manhood area
and reached down and took his semi hard man thing and
pulled it between my legs, he moaned a bit but didn’t
wake up for a few minutes until I had him hard and was
trying to get it back in my bum he was about half awake
when I finally got it started and he took over from
there slowly pushing it in and out until he had it all
the way in.

He had his hands wrapped around me trusting in and out
of me until he came in me again with a powerful load of
cum. I rolled over and faced him gave him a big juicy
kiss and said, “Good morning.” He smiled and said “now
that’s the way to wake up a man beautiful.” I kissed
him again and caressed his manhood and balls and asked
if he would like to join me for a shower.

We showered for a long time just standing under the hot
water kissing and cleaning each other, after I made
some coffee and we had some pizza for breakfast which I
served him as any good woman would. I was dressed in my
silk night clothes for this and he could not keep his
hands off of me he kept touching and caressing me as I
sat beside him eating.

We went back to bed for the rest of the morning and
made love until it was time for Jeff to go, as he left
we promised to see each other again real soon and we
had a long lingering kiss as he was leaving, him in his
suit and tie and me dressed in my beautiful black baby

I had a nap after Jeff left and then showered and got
dressed in my own clothes and went out shopping, I
spent the rest of the day window shopping at women’s
clothing stores just looking at all the nice stuff they
had to offer and thinking about what I would ware the
next time I got together with Jeff.

Jeff and I e-mailed everyday after that. We made plans
to get together again, we would talk about making love
to what we would do when we meet.

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