Date: Wed, 28 Sep 2005 15:03:29 EDT
From: TexLee29@aol.com
Subject: Uncle Len

 This is a true story of my sexual adventures beginning in
my teens.

    Growing up Uncle Len was my best pal. My dad passed away
when I was a baby and I lived with my mom, but between her
working and dating, I spent a lot more time with Len than
mom.  Len is younger that mom, and where this story begins,
I was 17 and Uncle Len was probably about 29 or 30.

   One night after I went to bed at Lens place I awoke
around midnight and couldn't fall back to sleep. I heard the
television playing in den so I got up to see what Len was
watching. To my surprise I saw there was woman sitting on
the couch drinking a glass of wine. I startled her when I
spoke and asked where Uncle Len was.

   "It's me, Jimmy, I suppose it's about time you met the
other me" she said.

   I was confused. The voice sounded like Len, but this was
one sexy babe sitting here, and I didn't know what to say.

   "I'm still the same Uncle Len, but I like to dress up as
a girl sometimes and I really hope this doesn't change how
you feel about me" she/he said. "I am actually relieved to
get it out in the open"

   "I suppose its OK with me" I replied, but I'm not sure I
understand"

   Uncle Len then proceeded to explain that from an early
age he has always felt most comfortable when he dressed this
way, and it was a tension reliever of sorts for him.
He was concerned that I would hate him for this but I
assured him it was fine, and in fact  I thought he made a
really great looking woman, although at the time it really
was strange to see him this way.

  "Here, let me show you some things" he said, and he got up
and went into his bedroom to get something. I watched as he
walked away. High heels, black stockings and garter, mini
skirt and satin blouse, long blond wig.I swear he looked
like about the sexiest woman I had ever seen!

   I heard Len come out of the bedroom and his high heels
clicking on the tile of the kitchen floor.

"I am pouring another glass of wine, Jimmy, care for a
little glass?"

"Sure, thanks" I replied.

"Now don't tell your Mom" said Len, "Don't tell her about
any of this"

"I wont, Uncle Len"

"Call me Vicky when I'm dressed, OK?

"OK, sure, Vicky." I said.
   Vicky sat next to me with some magazines that he
retrieved from his bedroom and opened them to pictures of
other guys dressed as girls. She (I guess she?)showed me
that it's quite common and lots of guys do it and I suppose
somehow that made me feel better about the whole thing, and
I am afraid to admit, maybe a little turned on by it.
I asked her if I could see the other magazines but she said
they were not for young boys to see. After a little pleading
she handed one to me and I opened it. It was full of
pictures of these T-girls (as I now know them to be called)
having sex with guys.

"Wow, do you do this too?" I asked.

"Yes, on occasion I do" she replied.

"Looks hot" I said.

"I can tell you like it" she said pointing to my crotch.

I looked down and there was my dick pointed straight up thru
the slit in my pajamas. I am sure I turned beet red and
tried to tuck it away, to no avail.

"Don't worry honey, its OK" she said. "I have one too"

"I suppose you do" I said, and we both laughed.

   We sat and talked for a long time and I asked her lots of
questions that she happily answered for me. We had another
glass of wine or two and I now felt real comfortable with my
Uncle Len as Vicky.  I was fascinated by this whole new
world by this point and as Vicky (Uncle Vicky?) pulled a
tube of red lipstick from her purse and touched up her lips,
I told her that her make-up was sexy. She had on a smoky
brown eye shadow, black eyeliner and long false lashes and a
deep red lipstick. She thanked me and playfully dabbed some
lipstick in my lip and I made no attempt to pull away.

"You know I always thought you would look great a dolled
up." She said.

"I don't think I am ready for that" I said, but not
protesting all that hard.

   It was getting late and Vicky suggested we turn in for
the night but I didn't want the evening to end. I was really
enjoying myself and trying to sort out my feelings. Sitting
next to this sexy girl, and being a horny 17 year old I
really wasn't sure what I should do. After all this was my
uncle and for the first time I wish he wasn't.

   Vicky stood up and reached for my hand as I stood.
She hugged me tight and said how she was so relieved this
was out in the open and that she was happy I understood.

"Quite a boner you have there." She said as I am sure she
felt it press against her as we hugged.
"Yes, I'm sorry" I said.

"Don't be, I like it" she said.

Now that really confused me, but she broke our hug and said
goodnight.

   I guess I was disappointed but headed to my bedroom. I
closed the door behind me and lay down. All alone and
thinking of this new Vicky, I instinctively begin stroking
my hard dick. All kinds of crazy thought went through my
head which was already spinning from the wine. I fantasized
that she would come into my room and suck me off with those
juicy red lips.

   It wasn't but a few minutes when I heard my bedroom door
open. By the light in the hallway I saw it was her. She had
removed her skirt and blouse and still wore her high heels,
garter, stockings and bra. Without saying a word she
replaced my hand with hers and gently kissed the tip of my
dick. I heard her soft moans mixing with mine as she slowly
worked her lipsticked lips down my entire shaft, pausing
when she reached the base, and then slowly worked her way
back up. I wanted it to last forever but I am sure it was
less than a minute when I felt it start deep inside me. I
stiffened and felt all tingly all over then begin shooting
my cum into her mouth. She sucked it all and kept squeezing
my cock and sucking to get it all.  I've jacked off a
million times but cumming never felt like this before. I was
still panting when she gave the tip a soft little suck and
put her tongue in the hole at the end, and then kissed it.
She leaned up and gave me a peck on my lips, whispered
goodnight, and left my room.

   As I fell asleep I knew the relationship with my Uncle
Len was different from here on out, and I really hoped there
would be more to follow. Damn, I thought, this is so cool.