Date: Sun, 26 Aug 2007 12:05:52 EDT
From: R
Subject: Park loo 3

I was concerned about Jason's future welfare - especially
his education. His mother clearly had no interest in him
at all. He'd managed to pass 10 GCSEs - 9 of them at
Grade A. There was a sixth form college locally, and I
gave them a tentative phone call, telling them that his
parents were divorced and both abroad, and that I was his
uncle. They were very receptive, and said they would in
all probability - subject to production of his
certificates - accept him to study A-level Maths, Physics
and Chemistry.

I phoned the flat and told him. He asked me if I could
call around. Naturally, I did!

We sat on the sofa, and he said, "Look, you are doing too
much for me. Don't think I don't appreciate it. I don't
know what I would have done without you. But I'd love to
do something special for you."

I had no idea what he meant. He continued, "You say
you've been straight all your life till now, so before me
you'd only screwed women or girls. Yes?" I had to agree.

"Well, then: I've always wanted to dress as a girl. Would
you like me to?" I didn't know what to say - apart from
"A blouse and tight jeans wouldn't hide your boner!" He
said, "No - I mean dress up properly, with a dress, bra,
panties, suspenders, stockings, and high heels - the lot.
And lipstick and mascara.  Christ! The prospect was
amazing. He was just so pretty that he'd pass for a girl
anywhere. Jokingly, I said, "Yes, Jason: very interesting
- but you have short hair." "OK" he replied - "I forgot
to mention the wig!"

I couldn't really argue. But I said, "If I agree, will
you let me take you out for dinner dressed like that -
and maybe book us into a hotel for the night?" The answer
was hardly a surprise: "Oh, please . . ."

By now, we were both so horny that we just had to strip
and do a 69. It was brilliant. I kept seeing him in my
mind's eye with his stockings and dress! And his cock
seemed so much larger: he put it so far into my mouth I
nearly gagged. But his cum tasted so sweet. And the way
he ran his tongue over my cock head was almost
unbearable.
The problem now was how to go about getting his clothes.
I had no idea of ladies' sizes. He said he would go and
buy them, telling the shops that he was going to a drag
ball. Great idea! I gave him œ200.

The following day, he called me on my mobile.
Coincidentally, I'd just been to Tesco and was in the
same park. But I had no intention of entering the loo!

H asked me if I could come to the flat that evening after
6 o'clock. Of course I could!

I arrived at a minute after six and let myself in. Jason
was sitting on the sofa. What a vision! He was wearing a
pale blue mid-calf length dress, and matching blue court
shoes. His legs were crossed, showing just a hint of
thigh, clad in stockings that made his legs looked
lightly tanned. A blonde wig framed his face, and his
makeup was gorgeous, with lipstick and mascara tastefully
applied. His smile sent my cock flying to attention. He
looked as beautiful as any young woman I have ever seen.

I had a suit, shirt and underwear in the wardrobe. So I
suggested that if we were going out or dinner, I ought to
shower and change - alone. I didn't want to interfere
with his appearance!

I showered, changed and ordered a taxi to a restaurant a
few miles away where there was a not very good dance
floor; but at least I knew the resident musicians would
play smoochy music on request. There was also a hotel
practically next door.

It wasn't a brilliant dinner. In fact the food was pretty
poor. But I was highly amused at the way the waiters
ogled Jason. It was fairly obvious that they thought I'd
hired an escort girl. He didn't notice a thing. At every
opportunity, he put his hand under the table and fondled
my cock and balls.

On the dance floor, I asked for a few old favourites by
Sinatra. There were never more than two other couples,
and they didn't mind. Dancing with Jason was such a
sensuous experience. He was so light on his feet, and
moved as well as any girl I'd ever danced with. The aroma
of his perfume, his face nestling into my neck, and his
cock being constantly pressed against me transported me
back forty years or so - except that this was so much
better!

After about twenty minutes, he gently put his tongue into
my ear, caressed my crotch and murmured, "Can we go now,
please?

I paid the bill and we left. The hotel was a five minute
walk away. We checked in as husband and wife, and the
receptionist didn't bat an eyelid. I sensed though, that
he was thinking, "Dirty old sod with a young call girl!"
I ordered a couple of bottles of white wine and we took
the lift to our room.

Before we'd had chance to look at our surroundings, the
bell rang. There was a waiter with the wine, an ice
bucket, corkscrew, two glasses and a red rose! He opened
one bottle and poured a little into one of the glasses.
"Would Sir care to taste it? He asked. "No thanks" I
replied. He bowed slightly and said, "Very well sir. If
there is anything else you require, please just phone
reception." I could see by his expression that what he
was thinking was "Randy old bastard just wants to get his
end away!" He couldn't have been more right.

But we still had a couple of glasses of wine. The Jason
drew my attention to a large plasma screen on the wall.
"I wonder if we can get blue movies" he said. I looked at
the various brochures on the desk, and sure enough, there
was a pay-view adult channel. The selection was
excellent. To my surprise, he didn't want a gay movie. He
said, "I'm your girl tonight. I want to see what they
do!"

We chose one featuring some slim Scandinavian beauties -
who looked amazingly like Jason.

He lay on the bed, on his back, pulled up his dress and
looked as though he was about to remove his panties.
"Hold on!" I said, "I want to do this properly." He
smiled, and we had a lingering kiss. God, he just smelled
and tasted so good. I put my hand on his left knee and
moved it slowly upwards. The feel of the nylon of his
stocking was fantastic. I came to his suspender, slowly
unfastened it and gently began to ease the stocking down.
Then I moved my hand further and encountered his smooth,
soft warm thigh. He shuddered, undid my belt and pulled
my trousers and underpants down, moaning gently.
Suddenly, he sat up and practically tore my shirt off.
"Hold on, baby", I murmured. I was now naked apart from
my socks! We got back into the same position, and I
continued my progress up his soft, silky thigh. I came to
his panties. They were damp - not from girlie pussy juice
but from his pre-cum. I took his ball sac in my hand and
gently squeezed through the thin material. Then I ran my
finger along his crack, before pulling the panties down
and taking hold of his cock. I'd never known it so hard.
"Strip me, and do my tits!" he suddenly said. His dress
was quickly off, as were both stockings. But I left the
suspender belt. It looked so fucking sexy!

He was wearing a bra that matched the colour of his
dress. It looked as though it was covering a pair of real
breasts. Of course I knew it wasn't; but when I unhooked
it, his nipples were huge. I took them in my mouth, one
at a time, and tongued and sucked them for all I was
worth. Then he suddenly shuddered, screamed "HEY, HEY!"
and came all over my chest and stomach. I thought I'd
ruined our evening with his release of so much pent-up
cum so soon. I was wrong.

We had another glass of wine each. My balls were really
aching. I felt I could shoot a gallon! But he didn't even
touch me. Instead, he said, "You couldn't watch the movie
because the screen was behind you. All the time I was
watching it and it was great. I think that's why I came
so quickly. Do you want a look now?"

He put it back on, and there was a gorgeous blonde being
pumped furiously. She had her legs over the stud's
shoulders. Jason said, "How about we try that? It must go
a long way into her!"

He straight away lay on the bed and pulled me to him,
then put his legs over my shoulders and guided my cock
into his hole. I could feel his suspender belt against my
nipples, tickling them and making them hard; and he still
looked so beautiful with that wig. The perfume still
lingered, too; and when he stuck his tongue down my
throat and his finger up my arse, I was in heaven. I
don't think I managed more than a dozen thrusts - but
they were so deep! We screamed and creamed together, and
I must have shot enough to fill my lover's arse and
entire body!

Afterwards, we just went to sleep. Nothing could really
compare with what had just happened. My next mission has
to be to sort out his education.