Date: Sat, 08 Dec 2007 15:48:37 -0500
From: ptrwales@aol.com
Subject: Paula's Adventures: Sam, My First

Hiya, I'm Paula and here are some of my cross-dressing adventures. Some of
the names and places have been adjusted to protect the real identities of
those involved, but apart from that, all of what you are about to read
actually happened.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Sam, My First.

Okay, earliest experience I remember is wearing my mum's black tights and
red satin panties -- was too young to get too excited. I dabbled into her
clothes whenever I could, usually tights or pop-socks, usually tan,
sometimes black.

When I was about 12 I discovered a pair of suspenders & black stockings in
my mother's wardrobe; I was hooked (`scuse the pun!!). This was the dawn of
the late-eighties and soon my mother's underwear draw was full of different
coloured underwear and stockings. My absolute fave were black lacy
suspenders and nearly black seamed stockings!! As always I dabbled whenever
I could and even managed to steal the odd pair of plain black tights for my
own use; I had no suspender belt of my own so it was pointless taking the
stockings!!

Things turned better in 1992; my elder sister, Michelle went off to
University, she was 3 years older than me, I was 16 at this point. Lucky
for me she left some of her underwear back at home (she had quite a good
collection too), and being roughly the same size, I helped myself to some
of her underwear and outer clothes for my own personal use. As always, I
dressed whenever I could, I looked relatively woman-like as I was quite
small framed and had shoulder length hair (thanks to my music taste).

My first sexual encounter happened just before my 17th birthday. My best
friend (Sam) was due to head over my house one evening to do some work on a
joint science project we were doing, but wasn't expected until 7pm. After
college that day I went home and dressed up in some white underwear I had
taken from Michelle, dark-tan stockings, black knee-length skirt and white
blouse, of course I put my hair in pigtails as always. I was conscious of
time as I knew Sam would be up at 7pm, and, as Mum would not be home from
work until gone 9pm I thought I was pretty cool until about 630pm, maybe
645pm!! Not so.

Whilst parading round the house dressed as an absolute cutie I wandered
into the kitchen, as I always do, slipped on my trainers and snuck out into
the back garden, it wasn't even 530pm so I thought I'd be okay especially
as we are not overlooked by any neighbours!! As usual I stepped out of the
back door and strolled towards the back fence, pretending to chat up a guy,
etc. You know, the stuff we all used to do when we first started!! Anyway I
was just heading back towards the house when through the side gate came
Sam, over an hour early!! I felt absolutely hopeless and just froze, as did
he!! Sam paused for a moment and said "Paul?", as if he was making sure. I
just stood there almost in shock. After what felt like an eternity I made
my way to the back door, blabbering to Sam, pleading for him not to tell
anyone or to understand or something, I was physically shaking -- I'd never
considered what I'd do if I was caught!! Sam followed me in and gently
grabbed my arm, I turned to face him and he just seemed to stare back at me
with such an understanding face I was immediately calmed. Eventually we sat
down in the lounge, I was still dressed as Paula and basically told Sam
everything. My biggest shock came when I paused to look at him, looking for
some sort of response, when he calmly came out and simply told me that I
looked amazing and that he'd like to see me like this more often!! I just
burst out laughing or was it crying, or both -- but the relief just flooded
over me, my secret would be safe... for now.

I thanked Sam and suggested that we go upstairs to my room and get on with
our science project, as that was the reason he'd come over in the first
place, so off we went. I suggested to Sam that I get changed into my normal
clothes but he was having none of it, telling me that he preferred me like
that and my mum wouldn't be home for ages yet anyway, so why the rush.

Anyway, we got on with the science project and did pretty well (we still
had 3 weeks in which to complete it, so plenty of time) it was nearly eight
o'clock so we paused and Sam nipped downstairs to get a drink; of course I
was still dressed as Paula, but decided that I'd start getting back to
being Paul again. Sam must have sprinted downstairs and back up again
because by the time he walked back into my bedroom I'd only just removed my
blouse. Sam stood in the doorway, a big smile on his face! I told him that
I wanted to get dressed back into my normal clothes now in case my mum came
home early, to which he simply agreed. As I started to pull down my skirt I
gave Sam a really cute smile,

"Bet you didn't know I was wearing these" I said, to which Sam gave me a
questioning look. I pulled the skirt down a little to slowly reveal my
white lace panties and then down a little bit more to reveal the tops of my
suspender straps. Sam's eyes lit up.

"Stockings and suspenders!!" he cried.

"Oh yes, I usually do. These are mine now, I knicked them off Michelle" I
told him. With that I let the skirt drop to the floor and sauntered over to
where Sam was sitting at the edge of the bed. I turned my bum towards him
and felt him run his hand up and down my left stockinged leg.

"these are very nice" he said, I do like you in these.

"Good" I said, "enough to be naughty for 10 minutes?" I asked

Sam stood up and pulled me closer and kissed me -- full on, French kiss; I
melted.

I looked him straight in the eye and told him what I wanted to do, with
that I dropped to my knees, undid his jeans and pulled his rock-hard cock
out of his boxers. Immediately I popped it into my mouth and started to
suck on it. To be frank I'm not actually sure I was even doing a good job,
but Sam seemed to enjoy it immensely. Sam pulled himself out and climbed
onto the bed, I followed suit and took his cock right back into my mouth
again. I was being such a slut, but I knew exactly what I wanted. In next
to no time Sam moaned heavily, bucked and shot wads of hot cum into my
mouth. I tried to swallow it but gagged and let the rest drop out onto
Sam's cock and balls. I managed to gather myself and cleaned up the
overspill, swallowing every last drop -- Sam just lay there in amazement. I
looked at the clock, it was now half past eight! Time was running out. I
told Sam that we had to get cleaned up and get changed, he agreed but asked
if I'd keep the underwear on, I agreed, as long as I could take the bra off
as it would be too obvious under my t-shirt.  I dressed in a shabby running
top & jogging bottoms.

We decided that it would be best if we carried on doing some of the science
project as it would look pretty reasonable when mum came home, which she
did, just before 9pm. She walked into my bedroom and just came over to see
what we were doing. I was conscious that I had not put socks on and was
still wearing the dark tan stockings, but despite this I kind of kept my
feet hidden as we explained to mum what we were doing and what the project
was all about. She seemed vaguely interested but soon left and went down
stairs to chill out and watch telly.

It was then that Sam asked me what other stuff I had so I went to my secret
hiding place (I'd just unscrewed the false bottom of the fitted wardrobes
in my bedroom) and pulled out a few things -- other items I just grabbed
from Michelle or Mum's draws or wardrobes whenever I wanted something
different. Sam pulled out a new pack of black lace top stockings and
suggested that he'd like to see me in these so I told him that I would wear
them next time he came up, thankfully he agreed, so he pulled out a pair of
plain black stockings that weren't new and smiled at me, asking me to
change into them now, if I would. I said I would but only if I could go to
the bathroom to which he disagreed so I slipped off my tracksuit bottoms
and slipped off the dark tan stockings. As I'd just finished clipping on
the black stockings I heard my mum coming up the stairs and knelt down the
other side of the bed. Mum opened the door and I peeked over the top of the
bed as if I'd been looking for something, she asked if we wanted anything
for supper, to which we replied no and that Sam would have to be heading
home shortly anyway as it was now nearly 9.30pm. Mum went back downstairs
and I slipped my jogging pants back on. That was too close!! I put my
hiding place back together, it was time for Sam to go then anyway. I
slipped on my trainers and followed him downstairs.

I told mum that I was just walking back some of the way with Sam as we
wanted to call in and see Jayne (one of our friends on the way -- I knew
full well that Jayne would not be there tonight as she was out on a date
with Darren, one of our other friends, but it gave me an excuse!!). She
asked me not to be late as she wanted an early night.

En-route to Sam's place we passed a small area of rough ground and wooded
area so I suggested that we sneak in there quickly for one last kiss. Sam
agreed so we found a secluded spot, I stripped off my male-clothes and
stood there in just my suspenders, stockings and panties -- Sam pulled my
white bra out of his jacket pocket and smiled, I slipped it on the put my
hair in pigtails again. Sam then backed off a few yards and told me to
crawl towards him on my hand and knees, which I did, though the ground was
a bit hard, I pulled up in front of him, and, on my knees again, took his
cock deep into my mouth. Again I sucked and sucked, licking his shaft and
balls until a few minutes later Sam's cock once again exploded into my
mouth, this time I managed to keep it all in and swallowed every last
drop. I smiled up at Sam then stood up, noticing a small ladder in the knee
of my left stocking, I just giggled and walked over to my own clothes and
got dressed again. Five minutes later we were at Sam's, 15 minutes later I
walked back through my front door. Mum was just about to head off to bed, I
did likewise and slipped under my covers in just my stockings and
suspenders. My final act of pleasure that night was to masturbate and come
all over my stockings!! Wow what a night!!

If you like this, then please keep an eye out for more of Paula's
Adventures coming soon, or e-mail me at ptrwales@aol.com

Lots of love

Paula

xxx