Date: Tue, 12 Dec 2006 15:23:38 -0800 (PST)
From: bill bobber <givingitupgladly@yahoo.com.au>
Subject: Getting Started 4      Trans - YF

This story contains scenes of explicit man/young man in girl's clothing
sex. Do not read any further if your local laws prohibit this kind
of writing. But then ask yourself, why am I living here? If your local
laws do not expressly forbid this kind of harmless fantasy and you are
packing a woody because this kind of story is just your cup of tea, then
please enjoy. Randylad(y)



Here I was. In a car, with a man, who had said he wanted to do things to
me that I had only been able to fantasise about. Things so private that
nobody else had known about them. Things like, taking a long, hard cock,
dripping with pre-cum into the warmth and wetness of my loving mouth.
Things like, dressing up in girl's clothing so I could be the girl that a
horny man could use to find satisfaction with. Like when he pushes me
back onto the bed and mounts me as I wrap my legs tightly around him -
his engorged cock impaling my virgin anus for a long night of loving.
Yeah, that kind of thing.

Jim is my friend Paul's older brother. Where Paul and I are teenagers
approaching manhood, Jim is all man. I'm sure he's at least six feet
tall. I don't know him very well because for the last four years he has
been away at college, but at least I know something about him. I know his
name and where he grew up. I know he seems nice and doesn't look like he
wants to hurt me or trick me into anything. I know he's very handsome.

He's also pretty silent. We've been driving for several minutes and
neither of us has said anything. I'm getting more nervous by the second
and I'm just thinking of maybe starting to panic, when Jim turns the car
onto a side road and then parks under a tree where we can't be seen from
the road.

He turns off the engine and then turns to me. "I'm glad you showed up
Randy. I wasn't really sure if you would or not." His voice is soft and
gentle.
Do I trust him? This would be my chance to say "you've made some kind of
mistake - I'm leaving!" But no, actually my chance to say that was back
in the alley before I got into the car. And I hadn't done that had I? I
had gotten into Jim's car without any hesitation. I decide.
"Yeah, well... I was pretty nervous. I mean, I am pretty nervous. I mean,
I'm super nervous. I've never done anything like this before. Not that
I'm saying you want to do anything cause, you know, I probably don't
and..." I couldn't stop myself from talking.
"That's not true now is it?" said Jim smiling at me. (his smile is sooo
nice!) "You've been having quite the times with my brother."
Okay, I guess with everything else being out in the open here, that
shouldn't have come as a surprise - but it did. "Oh, you know about
that?"
"Yes, I've watched you quite a few times. It's very interesting." He's
still smiling.
"Yeah, well, we, um... I can explain." No I can't. I'm caught.
Jim laughs, but in a nice way, not cruel or mean. "There's no need to
explain. You're just two young men having fun, 'exploring your sexuality'
I think it's called. No harm being done, is there?"
"Uh, no."
"But, there is a few things I've noticed. First of all, whens the last
time Paul did anything to you?" That was a good question. It was true
that over the last few months our little sessions of mutual masturbation
had moved away from the "mutual" part, and more towards the me giving my
friend a hand job and then going home and masturbating while I imagine
being my friend's willing sex slave part. That way I could capture my own
cum and swallow it, imagining that it was Paul's.
"Another thing I noticed is that you have developed a rather unique
wardrobe."
I didn't get it "What do you mean?"
"The panties you would wear. The girls panties."
I swallowed."How do you know about that?" I asked, almost in a whisper.
"When I watch you jerking off Paul, you're on your knees and I guess you
can't tell that the panties show above your jeans."
"So, do you like watching Paul and I?" I'm not sure if I should be mad or
not.
"Yeah, it's been fun. I'm not usually much into voyeurism, but you two
are so hot, especially you, that I really can't help myself."
Jim just said I was hot. Me. I was scared, nervous, and I had to admit,
the way things were going I was getting a little excited too. So I had
to make sure about this.
 "You think I'm hot?"
"Definitely!" said Jim with that damn smile again. Okay, now I really was
lost. Where was this going? What should I or could I say? How much should
I reveal to Jim? It seemed that he already knew a lot more about me than
anyone else knew, but that didn't mean I could trust him. Not by a long
shot.
"Listen Jim, I guess you've got me. I like to jerk your brother off. More
than I like him doing it to me. And I like to do it wearing my sisters
panties. Fine. But I'm really freaked out here cause I don't really know
anything about you or what you think."
To my surprise, Jim answered my little outburst with an apology. "I'm not
doing a very good job of making you feel relaxed am I?'
"Not very!"
"All right," said Jim. "Let me tell you something about me. Okay? Maybe
then you can trust me. I've been away at college for the past four years.
During that time I've had a roommate named Andrew. He's a very nice guy
and is a hard-working student, but what most people don't know about him
is that when we were alone in our room he wore only women's clothing and
went by the name Anna."
"Wow!" I couldn't help myself.
"There's more. Do you want to hear?"
"Yes! Yes!"
"Well, Anna and I were lovers." He said this like he had just said they
ate ice cream together. Like it was normal and okay.
"Wow!! Double wow!! You two... like... she, I mean he was...!?"
"Anna loved to suck on my cock. When I would cum she made sure she
swallowed every drop. But even more than that she loved it when I fucked
her sweet ass all night long."
I was amazed to hear this description of hot sex, but even more amazing
was that Jim was admitting to me that me obviously enjoyed making love to
a man wearing women's clothing. I didn't know how to respond to this.
"Well?" asked Jim. "Do you have anything to say about that?"
"I wish I was Anna."

To be continued


I have really enjoyed the comments received so far. Thank you. Hearing
from you makes writing worth the time and effort. I'd love to hear more.
Randylad(y)