Date: Mon, 30 May 2011 16:34:02 +0100
From: Lara Porter <laporter12@gmail.com>
Subject: The Lingerie Question (TG)

I was 17 when I met Alan. He'd moved in next door to my
parents and seemed nice enough. We said hello but nothing
else. If I'm honest I never imagined how things would
turn out.

At the time, I was a quiet boy struggling to come to
terms with life. Emotionally I was a late developer and
it had never quite clicked with the girls at school. I'd
become a quiet, reserved figure who kept out of trouble.
Privately I'd started to use the internet to look at
adult sites - mainly sexy girls. Nothing out of the
ordinary mind you, just your average teen boy kind of
thing.

It was a dull April day around Easter. My parents had
gone away on holiday leaving me with the house to myself
for 2 weeks. I'd walked down to the shops for some milk
and bumped into Alan on my way back.

We got talking. Small talk, nothing more when he
suggested if I was on my own I pop round his house for
lunch. Having been on my own for a few days, I was
grateful for the company so thanked him for the offer and
followed him home.

Lunch was fine but the conversation got a bit weird. We
started to talk about girls and how they looked. I
mentioned how I liked girls in sexy lingerie. A few
minutes after I mentioned it, Alan piped up

"So is it the lingerie or the girls you like?"

"Sorry?"

"Is the attraction the lingerie?"

I must admit that got me thinking. I'd never considered
that before and there was something at the back of my
mind about the lingerie. It looked really nice and my
mind drifted to the thought of wearing that sexy red lace
babydoll and thong I'd seen on that cute teen red head.

"So it's the lingerie then?"

My daydream was abruptly interrupted by his words and I
must've gone a thousand shades of red in embarrassment.
It took all my efforts to raise my head to look at Alan -
he was grinning at my discomfort. I tried to speak but
nothing came out of my mouth. Thankfully Alan spoke to
spare me

"It's ok. I'm not going to tell anyone. Besides plenty of
youngsters like you try wearing women's clothes. "

"Really?"

"Yeah. Have a look online when you get home. Some guys
just want to experiment while some go a bit further..."

The conversation mercifully switched after that and not
long after I made my excuses and headed home. I just
couldn't get Alan's words out of my mind though. What did
he mean about taking things further? Needless to say, the
first thing I did on getting home was to head for my
computer. I started to search for boys in lingerie and
was amazed at just how much I found. After a few minutes
of looking, I found one page that really brought
everything into focus. It showed a young boy of my age
with long hair stripping out of his male clothes and
putting on a gorgeous red bra and panties set and then
getting into a flowing evening dress with a floral
pattern. He then applied makeup at a table. Jeez he
looked utterly stunning, as sexy as any girl I'd seen. My
cock by now was rock hard and I couldn't help but jerk
myself off. I was just so aroused at the sight and my
mind was burning with two questions - could I look as hot
a chick as that and if I could, what would I do then?

I didn't get a lot of sleep that night. I was imaging
myself dressed in different girly outfits and strangely
thinking of Alan. The next morning I headed out early to
buy some beauty products as I'd decided that my little
body hair had to go. I picked up the products I needed
and headed for the food aisles but on my way through my
eye was drawn to the women's clothing section. I noticed
a pack of pink girls' panties with a floral trim. They
looked sooo cute I though I just had to have them but I
couldn't could I? By this point though so I was so turned
on by the though that I just had to do it. Putting them
in my basket I quickly got my food and headed for the
self-service checkouts. What can I say? I was still dying
of embarrassment but just couldn't stop myself.

I don't think I've ever got home so quickly as I rushed
back. I got straight in the shower and began to shave my
body from top to toe. Getting out of the shower, I
applied some body lotion I'd bought. God, I felt so
smooth and girly it was untrue. I opened the panties and
put a pair on. They felt wonderful on my smooth skin. I
was in heaven and before I knew it I was shooting a load
on the bathroom floor. I was glad I'd bought a pack of
panties as that was the first pair in the wash!

Once cleaned up, I headed back to my computer and sat in
just my panties and went back to the girlyboy from the
previous night. The page had a link to another site that
I followed. There I found more shots of the same girl in
different outfits. In one she was in a two-piece swimsuit
that barely covered her aroused cock but still showed off
her feminine figure to perfection. If only I could reach
that level. It was at this point I went to the news page
of the site that next week "Gemma" would be filming her
first hardcore session for the site. Wow. That was a
whole new line of thinking for me. Hardcore with whom?
Female or even male? I really was very na‹ve!

Before I had too long to think about it the doorbell
rang. Pulling on my clothes I quickly went downstairs to
find Alan standing there.

"Hi Paul. I was out shopping earlier and I thought of you
when I saw this. Don't open it now, I've got to dash
anyway but maybe I'll see you wearing it sometime. Bye"

Ok now things were getting very strange. I had a strange
feeling I knew what I'd find in the package. Opening it
up sure enough it was a two piece set of a pink lace
babydoll and matching thong. Utterly gorgeous and I
couldn't wait to try it on. If felt even better than it
looked. I felt like a girl and a very sexy one at that.
There was one thought in the back of my mind - what did
Alan mean about seeing me wearing it sometime? As I
considered that question I began to spurt my juices all
over the lace.

Part 2

The next day I decided to head into town to do some
shopping. As I was leaving the house, Alan was in his
front garden.

"Hi Paul. How did you like your present? Have you worn it
yet?"

My reddening face answered for me!

"I suspect it's needed a wash already then?"

Now I was really struggling. I was uncomfortable enough
knowing Alan had interest in me wearing lingerie but for
him to know the effect it was having on my body was a bit
much. I just couldn't being myself to look at him but
when I finally did he was given me a strange almost
lustful look. I don't know why but at that point I
blurted out that I was going shopping in town for more
clothes. I couldn't help myself. I was so caught up in
the desire to become as sexy as Gemma looked online and
Alan's expression was really having an affect on me.

"Tell you what" Alan replied, "if I give you some money
to buy some pretty clothes would you model them for me?
I'm away with work for a few days but I'd love to see you
when I get back. I think you'll make a pretty stunning
woman."

I would? Alan's words made me feel so good and I had to
admit he looked pretty handsome. No hang on, what was I
thinking? I'm a boy not a woman! Yet despite telling
myself this, I knew what I really wanted was to be
wearing a beautiful dress and made up like a million
dollars. A show for Alan really wasn't going to be a
problem. I agreed and Alan very kindly gave me some cash.
He also offered to give me a lift to town, which I
readily accepted. As we drove I could feel his eyes
glancing towards me. I was growing curious. What could
happen between us?

Alan asked me what I though I might buy and I told him
about the evening dress from the internet. He said he
liked the thought of it and suggested stockings and
suspenders would go well with it and make me look a
really sexy woman.

"I wish," I laughed.

"Why not?" He countered, "You've got a great feminine
figure and nice hair. I think you're a lot closer to what
we're looking for than you realise."

With that, the car pulled up at the shops and I headed
off with Alan's words ringing in my ears. I quickly chose
some clothes in the first shop I went into. I really
didn't want to hang around and felt really uncomfortable
looking at the racks. I chose a floral summer dress and
an elegant red evening gown. In the lingerie section I
picked up a white suspender belt and matching stockings,
bra and panties. I was about to move onto the shoe shop
when I caught sight of a stunning blue underwear lace
dress. Wow, it looked lovely and I couldn't resist. I was
growing obsessed with girly clothes!

A pair of heeled shoes followed and then I headed to the
beauty store to look at make up. Now here was where
things were going to get difficult. In all honesty I
didn't have a clue where to start. I took my best guess
of a few things and bought a bottle of perfume I'd seen
advertised on TV. That was all Alan's money and a
significant chunk of mine gone so I headed for home and
the fun of trying everything on.

On arriving home I quickly showered and sat down to try
my make up. I followed directions I found on line and in
fairness for a first attempt it wasn't too bad. I put the
underwear on and plumped for the evening gown first. I
stared at myself in the mirror unable to believe it. I
looked stunning. I actually looked like a girl and a
pretty foxy one at that! It was time to try the shoes and
practice walking in heels; not as easy as I though it
would be but after a few minutes I was getting the hang
of it and started to practice walking in a feminine way.
I don't think I'd ever been as turned on in my life. I
felt so girly and happier than ever before. Of course it
wasn't long until my excitement exploded leaving me with
a bit of a clean up.

The next couple of days were spent at home mainly dressed
as a girl and enjoying the liberation of it all. I was
aware that Alan would be due back from his business trip
and wondered what would happen then. Was I ready to see
my transformation? It was thinking of Alan's return that
I remembered the promise of Gemma's hardcore session. I
headed for my computer and headed to the site to see if
it had been posted. Lo and behold there it was - a
picture showed Gemma in a mini dress and whale-net
stockings with high heels. She was wrapped in the arms of
a muscular man with his hands around her waist as she
turned behind to kiss him. My jaw dropped at the image
and I clicked on the link to watch the video. It started
with Gemma resting on the bed as the man came into the
room. He sat beside her running his hands along the side
of her body, paying attention to that cute butt. Gemma
came to and sat up placing her hands on the man's torso
and giving him a passionate kiss, her hands sliding under
his clothing and feeling the contours of his muscles; the
man's hands moved to Gemma's tiny breasts and began to
massage the small mounds. The groans of pleasure from
Gemma went right through me. This was so hot.

The man then removed his clothes exposing a large and
very erect penis. Gemma's eyes seemed to widen at the
sight and she began to kiss her way down his body. After
what seemed an eternity she kissed the tip of his cock
and then ran her tongue down the length of the shaft. She
then placed the cock in her mouth and began to gently
suck on it. The man placed his hands behind her head and
began to force her to bob up and down on it at an ever-
increasing pace.

By this stage my mind was blown. This was the hottest
thing I'd ever seen. A few days ago I was staring at
Gemma and wishing I could look like her and now I found
myself going further. I wanted to be her. I wanted to be
sucking that cock. She looked the perfect woman and
that's what I truly craved. I began to wonder about Alan
and if he was hoping his kindness would lead to me doing
this to him. Or perhaps even more.

By the time the blowjob had finished I'd shot a load but
was still hard. Now the man placed Gemma on her hands and
knees and began to kiss her buttocks gently separating
them with his hands as he did so. His tongue slowly moved
across and into the gap separating them and began to dart
around her hole. The camera focused on Gemma's face and
the absolute ecstasy she was in. After a few minutes this
tonguing was replaced by a finger as the man began to
ease himself behind her and then finally he moved that
large prick into the hole and began to fuck her. Gemma
cried out in a mixture of pain and pleasure as he entered
her but it was quickly clear that she was loving every
minute of it. They switched positions several time until
finally he removed his cock and shot a large creamy load
all over her face and down the front of her dress.

The video had lasted about 18 minutes and by the end I
was exhausted and in a very sticky mess. My mind raced to
Alan. Is this what he wanted? Oh, I so hoped it was. I
wanted to become a real girl and feel the joy Gemma had
on screen. I'd do anything for him. But what would it
feel like? I'd never had anything pressed up my butt
before and was slightly nervous that Alan could be a big
boy. Searching my room I found a marker pen and decided
to use that as an experiment. Firstly I lubricated my
finger and entered myself. It felt nice and I began to
slowly finger fuck myself. A finger however just wasn't
enough and tried the pen. I fucked myself for as long as
I could until I orgasmed again at which point my body had
reached the point of exhaustion. I feel asleep where I
lay in my sticky cum soaked girl clothes.

Part 3

A day later Alan returned from his trip late evening. I'd
made sure all the clothes were washed and ready for my
display. I'd hoped he would call straight away but it was
late and he must've gone straight to bed. I felt
disappointed but looked forward to the next day.

I was doing some chores when the doorbell went the next
morning. It was Alan.

"Hi gorgeous. Did you miss me?"
"Hi Alan. How as your trip?" I replied, ignoring his
previous question. Hey, I didn't want to seem too keen!

"Good thanks. I brought you a few presents back. Here's
one. I've got more for you later. Why don't you pop round
tonight for supper Lara?"

Lara? So that was to be my girly name was it. I was ok
with that. It sounded dead cute to me. The present he
handed me was a pair of clip-on hoped earrings. That was
part of the look I hadn't thought of!

"Ok. Do you still want your fashion show?"

"That'll be great. I'd like to see you in all the things
I've got you".

I took the hint on the babydoll and that removed any
lingering doubts on Alan's intentions. I was overjoyed. I
was going to spend the night with a handsome man who
would make me the girl of my dreams!

The day dragged on for an eternity until it was time to
get ready. I decided I'd actually leave the house dressed
in my evening gown. I was a bit nervous about being
spotted but was confident that nobody could be sure it
was me if I was spotted. I packed the other clothes in a
bag. My makeup done and the earrings in place, I headed
out for my date with destiny.

Alan opened the door and his eyes bulged at the sight of
me.

"Oh my God. Lara you look stunning. I knew you were a
sexy princess but never that sexy"

He lent forward, kissed my cheek and put his arms around
me. I gave him a gentle hug and thanked him. He poured a
glass of wine for us and we started to talk about my
shopping trip. Alan wanted to know the details of
everything I'd bought. He then got out the next present -
a really gorgeous gold necklace. He insisted on putting
it on for me. He stood behind me and kissed the nape of
my neck as he finished. I clutched his hand and thanked
him for all he'd done for me.

"Ever since I moved in I'd imagined you as Lara. You've
got such a great figure and just thought somebody needed
to show you. I'm so glad it was me."

"I am too Alan. I've never felt so happy."

With that he took me in his arms and hugged me tightly. I
could feel his cock growing and pushing against me. I was
clearly having the right effect. He moved his hands along
my back and pulled away slightly.

"You're so beautiful Lara. Would you mind if I kissed
you?"

I didn't bother to answer as I tilted my head to the side
and invited him with my lips. Our tongues touched and
soon circled in an increasingly hot clinch. I moved my
hands now across his back and under his shirt touching
that manly skin for the first time. His hands moved
downwards to my butt and began to cup the flesh. I moaned
in delight. God I wanted him so badly now.

We broke apart and he took my hand and led me towards the
bedroom. My heart was pounding now as Alan kissed me
again. I felt so turned on but was still a little scared.
He must have sensed that as he lovingly held and stroke
me, telling me how beautiful I was. I began to move my
hands to unbutton his shirt and run my hands over that
chest. I moved my head to kiss him there as I took the
shirt off. As I did so I could feel Alan undoing his
trousers and kicking them to the floor. My hand brushed
down and I felt his erect cock for the first time. My
tongue continued to run along his torso as I began to
stroke that lovely sword. God, I wanted this. Alan
groaned in pleasure.

"Oh Lara, you're better than I had ever dreamed. You
really are the perfect girl. Please darling, kiss my
cock"

I didn't need any persuasion. I first smothered it with
little kisses and then began to roll my tongue along the
shaft just as I had seen Gemma do online. I placed his
balls in my mouth and sucked on them. This was all
proving too much for Alan who put his hands on the sides
of my face and guided me to the tip of his dick. I slowly
gobbled the shaft and began to gently suck on it, moving
it up and down between my lips. Alan's hands kept me
there - not that there was any danger of me moving. I was
loving it. This was a dream.

"Darling, you're amazing, I'm cumming".

I hadn't actually considered that he would actually cum
in my mouth (my only "experience" was the porno after
all) but I'd determined quickly that I'd try to swallow
his seed. It hit the back of my throat hard and fast and
I had to keep swallowing, although plenty still escaped
from the sides of my mouth. As Alan went limp I continued
to clean his cock, swallowing the remaining sperm. He was
wiping my face of the overspill and offered me his hand,
which I also licked clean.

"How was that darling?" I asked.

"You're a very special girl Lara. I hope we'll have a lot
more fun tonight"

"We will darling but I think it's time I got changed
don't you?"

I knew Alan would want to see that babydoll and I was
also conscious of the sticky patch in my panties. I
hadn't touched myself but had still cum. Boy was I horny.

I made my excuses and headed to the bathroom. I cleaned
myself up and re-applied some makeup. I removed the dress
but left the cum stained panties, bra, stockings and
suspender belt on. It was time to put on a show. I went
back into the bedroom and found Alan lying on the bed. He
sat upright as I went over and kissed him on the lips. I
motioned for him to lie still. Slowly I began to strip
out of my remaining clothes until I was totally naked.
Alan was playing with himself and I couldn't resist going
over and giving him a passionate tongue kiss while he lay
there. His hands quickly left his erection and moved
towards my butt and I felt his thumb pressing against my
boipussy. I pulled way and went back to my show. Putting
on the thong and babydoll then dancing seductively in
front of him, squeezing my breasts. Then I turned away to
give him a view of what I knew he really wanted. As I
turned back there was nothing but lust in his eyes. I
knew I wouldn't leave his house a virgin. I would be a
real woman and I couldn't wait.

I made me way onto the bed and snuggled up next to him.
We kissed and cuddled for a short while but I knew it
wouldn't last long. Alan was a man on a mission and he
wouldn't be held up for long. He began to play with my
breasts, gently biting my nipples. I squealed in joy. He
then put me onto my hands and knees and began to kiss my
ass cheeks. I was pleading for him to tongue me; I've
never known such desire. After what seemed an eternity
his tongue touched my hole and began to tease the
entrance. Slowly it began to enter my hole and I could
feel him start to tongue fuck me. While he did this, he
surprised me by placing his hand on my cock and starting
to rub through the material of the thong. I soon cried
out in joy as my orgasm hit. He took his cum stained hand
and began to massage it into my hole, lubricating me for
what was to come.

"Lara I love you. I want to make love to you"

"I love you too Alan. Please, I want you to be the one to
make me a woman"

I gazed lovingly into his eyes as he rolled me onto my
back and placed a pillow to raise my hips. Then he began
to move forward bringing his cock to the tip of my hole.
I felt the pressure grow until he began to penetrate my
ass. Tears began to roll down my face as the pain hit but
it quickly gave way to the most amazing pleasure. Alan
finally rammed the rest of his rod into my boipussy and
lay still for a moment, as I grew used to the feeling.
Then slowly he began to withdraw then thrust forward.
Wave after wave of ecstasy began to rush over me; my arms
ran across Alan's back as I held onto my lover for all I
was worth.

We kissed passionately and I hoped the moment would go on
forever but I could feel that Alan was approaching his
climax. He stiffened and shot his load up my pussy,
collapsing on top of me in exhaustion in the process.
Such was the excitement of his ejaculation, my own orgasm
arrived on cue. We lay entwined in a sticky mess on the
bed, his juice slowly trickling down my thighs.

We fell asleep in each other's arms. I drifted off
wondering where things would go from here. My life was
changed forever.