One Handed Tales 4 Surrogate Schoolgirl
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One Handed Tales #8: Library Girl free porn video
This story is pretty much 100% true. The names have been changed to protect the
guilty and the dialogue is probably only close, not entirely accurate (it was
ten years ago - give me a break!). If you're at all interested to know, this was
my first time dressed in public, first time dressed completely and first
girlfriend I ever dressed with. I'd never really worn any female clothes before
then, but had always been intrigued by them and had quickly tried a few items
before meeting 'Michelle'.
One Handed Tales #8: Library Girl
By Sarcastic Slut
I had been going out with Michelle for just over a year. We were both 18 and she
was one of my first girlfriends. Come to think of it, I was one of her first
boyfriends as well.
I was at her house one night. She lived a couple of towns away from me. We'd had
a great dinner, cleared up together and settled to listen to some music, chat
and finish our wine. She suggested a game of Trivial Pursuit. I agreed slightly
unenthusiastically as she wasn't actually all that good at it and I felt bad to
keep beating her. I also wasn't patronising enough to let her win on purpose.
But she was determined to beat me sooner or later so I agreed.
We were planning a trip into the centre of London sometime soon to do some
Christmas shopping and somehow, I don't remember exactly how, I found myself
agreeing to Michelle's bet that if she beat me at Trivial Pursuit I would wear
something stupid when we went shopping as a forfeit. I wish I could remember how
the subject came round to this but I can't as it didn't seem important or Earth
shattering at the time. I agreed as long as she would agree to wear something
stupid if I won.
She managed to a bit better than usual and just about beat me. It was close but
she had definitely done better than usual. She thought for a moment and decided
that I would be wearing lipstick for our shopping trip.
"Do you want to choose the colour you will be wearing, Don or shall I? I know,
we'll go into one of the big department stores and ask one of the saleswomen to
suggest a colour for you. I'm sure that'll be alright if we explain why you want
to buy a lipstick."
"Now wait a minute," I protested.
"Are you trying to wriggle out of the bet already?" She frowned at me. "I
thought you would be reasonable enough to handle being beaten at Trivial
Pursuit by a girl. I never thought you'd get all pissed off about it and welch
on a bet."
"I wasn't trying to welch on the bet. I didn't think you meant lipstick, I
thought you meant I'd have to wear a pair of nasty flares, a stupid shirt or
something."
"Well you should have asked and we should have agreed on the exact terms before
we played. You just assumed you'd win and didn't care about the terms. Serves
you right."
"Now that's not fair! We should play again and agree what the bet is before we
play."
"If I agree to play again, it's double or quits. If I win you wear the lipstick
as well as something extra of my choice for each segment I get more than you do.
If you win, I let you off wearing the lipstick and you can choose one thing for
me to wear."
"But..."
"Or you can just agree to wear the lipstick like you promised."
I thought for a moment. I had agreed to the bet and Michelle was definitely on
the moral high ground here. Also I was rapidly falling in love with her and
really did not want to do anything to annoy her or make her think I was less
wonderful than she had imagined. I sighed.
"Okay. One more game." I grinned, "But I'm going to thrash you and find the most
hideous dress imaginable for you to wear."
She kissed me on the tip of my nose and said, "Don't get too cocky, I'm on form
tonight. I can't wait to see what colour lipstick the woman in the department
store will suggest for you."
We set the game up again and started playing. I was at an immediate disadvantage
as I took several turns to throw a six to start. Michelle was just looking
extremely confident and was putting me off by discussing lipsticks and
theorising about what colours would suit me.
Distracted and worrying about the outcome, I kept second-guessing myself and
getting answers wrong. Michelle on the other hand seemed to get a load of
questions which were really easy. By the time she had gained all 6 segments and
was heading back to the centre I had only three and was struggling to answer a
question for another one.
As it turned out, her final question was remarkably easy and she danced round
the room, gloating and singing about her victory.
"Hah, hah! You're my bitch now!" She carried on dancing and singing and finally
plonked herself on my lap with her arms round me. She stared at my mouth.
"What?" I asked.
"Pink lipstick I think. That would suit you better than red. But I suppose it
depends what colour your blouse, skirt and wig will be."
I nearly threw her off me. "My what?!"
"Your blouse, skirt and wig. I won by three segments, I get to choose three
other things. Again you were too arrogant to agree terms before playing so it's
all my choice."
"You can't do that!"
"I can, you agreed, we shook hands on it. I'm being nice having a top and skirt
as separate items. If you annoy me I'll choose a dress, a wig and long false
fingernails."
"You can't make me wear a skirt!"
She ignored my outburst and looked thoughtful, "Maybe you'd look good with
matching lipstick and nail polish. If I can find a dress in a matching
colour..."
"Michelle!"
She looked round at me. "Are you about to tell me that I have a boyfriend who
would promise something, twice, then go back on his word? I thought I could
trust you." She got off my lap and, looking disappointed, she stalked into the
kitchen to get a drink.
I followed sheepishly and saw her wipe a small tear away as she heard me and
turned to face me.
"Michelle, I'm sorry. Of course I would never break a promise to you."
Basically, I begged to be let off. She gave me one more chance. She would play
one more game. If I won I would only have to wear the lipstick but would
definitely have to buy it in a department store when we went shopping and she
would choose the colour for me. If I lost... I would have to dress completely as
a girl. It wouldn't be for the shopping trip and would only be for a short time
but I would have to prove that I could get away with it in public. This would be
a further bet - If she recognised me she would win the bet and I would still
have to wear what she chose for the shopping trip. If she didn't recognise me, I
would be let off everything including the lipstick.
What was I supposed to do? I usually beat her at Trivial Pursuit. She'd had a
couple of lucky games but surely her winning streak was over now? Wrong! I
foolishly agreed. It was close again but she beat me. As the game got nearer and
nearer then end I was panicking more and more about the thought of dressing as a
girl in public and my game fell to pieces. I sat there stunned as she answered
her final question and gave me a huge, smug grin.
She explained the rules. When the opportunity arose (she'd decide when that was)
I would get dressed as a woman and go to the public library for the town between
the towns where we lived. I would be there at a certain time and would wait
until she arrived. There were six floors to the library. I would choose one and
sit reading a book. If Michelle recognised me and came over to talk to me she
had won. If she looked round and didn't spot me, I would win.
I was to go to a charity shop and select my own clothes so that she wouldn't
know what I was wearing but she insisted that it be a skirt or dress, not
women's trousers.
A couple of weeks later, the opportunity did indeed present itself. I had been
hassled by Michelle to go and buy some clothes ready for the outing. She had
also insisted on giving me lessons in applying makeup. I had seen the wisdom of
this - the better my makeup, the less likely that anyone would spot me as a man
and the less likely Michelle was to recognise me and win the bet. I listened
carefully, blushed furiously but obeyed when she told me to try the makeup on
myself and Michelle seemed very pleased when after one attempt I came downstairs
(her parents were out) to show her. I had basically copied her makeup style, not
knowing any different and it was strange when we stood next to each other in the
mirror looking at ourselves.
We did not look anything alike but it was strange seeing myself with a fairly
feminine face. The eye makeup completely changed the apparent shape of my face.
The addition of lipstick and blusher made me look very odd indeed. Still like me
but not like me if you see what I mean. Like a sort of tomboyish sister perhaps.
Michelle was giggling as she kissed me and we snogged for a while, smearing both
our lips.
When the day came, Michele had to work for the morning so we had arranged to be
in the library for about 2 O'clock. She had made me promise to be there from
1:30 so that there was no chance of her seeing me go in and I would be settled
with a book by the time she arrived.
The chance to do this had occurred because my grandparents were away for a week.
They had a delivery of something booked and I had promised to take it inside for
them so I had been left the keys. I met Michelle there in the morning. She
finished work at 1:30 so I had said I would give her the keys and she could let
herself in to get changed out of her work clothes to come meet me in the
library.
I kissed her and she went off to work. Stalling, I made a cup of coffee, flicked
through a newspaper, listened to the radio but knew that eventually I would have
to get dressed in the women's clothes I had bought.
Embarrassed beyond belief, I had run into a charity shop, bought some women's
clothes quickly and run away again. This meant that I had bought a short skirt
without thinking. It wasn't ridiculously short but it was a few inches above the
knee. It wasn't until later that I'd considered my hairy legs.
Embarrassed again, I had gone into a shop to buy some opaque tights but when I
tried them they were not quite opaque enough to completely hide the hairs from
sight and many of the hairs just stuck straight through the tights anyway. I
also managed to ladder the tights as I removed them.
What should I do? I thought about buying more opaque tights and wearing two or
even three pairs to hide my hairy legs but couldn't face going back into the
shop for more. After biting my nails right down worrying about it, I decided
that I would have to shave my legs.
Then I realised that I would have to wear tights anyway. I went to a different
shop with a smaller selection and was forced to buy a 3 pack of 15 denier
tights. That decided it. I would have to shave my legs. If only I'd thought
about it in advance and made sure I bought an ankle length skirt!
I climbed into my grandparent's shower and got myself clean, using shower gel
lent to me by Michelle for today. After a couple of minutes of dithering I made
the first sweep with the razor and stood open mouthed watching the hair slide
easily off my leg to leave a smooth patch of skin. I felt it and was amazed by
how different it felt.
It took well over half an hour to shave both legs and by the time I'd finished I
was tingling with the new feelings of having completely bare legs and the water
running down my newly smooth skin. I thought about it for a minute more and
decided to shave my chest as well, it would surprise Michelle, maybe even give
her a laugh. When I'd finished, I took a new razor and made sure my face was
free of a beard.
I climbed out of the shower and cleaned up. When I was dry I went through to a
bedroom where I had left the things I would be wearing. I could hardly believe
what I was doing as I pulled a matching bra and panties (another loan from
Michelle) out of my bag.
I took a deep breath and slid the panties up my legs, still in wonder at the
feeling of their smoothness. Next I struggled with the bra. I had seen Michelle
putting hers on and clipped it in front of me, slid it round the right way and
put my arms through the shoulder straps. It felt incredibly weird as the straps
snapped into place on me and the smooth satin material pushed at my smooth
chest.
I pulled a pair of breast pads from the bag and stuffed them in the cups of the
bra, shoving a pair of stockings in behind the pads to give me medium breasts of
a reasonably realistic shape.
I removed a pair of the tights from the packet and rolled them carefully up my
legs, shocked by how nice they felt with no hairs snagging against them. I stood
there for a minute, running my hands up and down my smooth, nylon covered thighs
and blushing as my penis reacted inside the satin panties. That was something
else I hadn't considered. What if the skirt was a bit too tight and showed me if
I got an erection while outside. I was 18 at the time and inexplicable, unwanted
erections were not unusual for me.
I went back into the bathroom and dealt with it, feeling very strange standing
there in bra, tights and panties, touching myself and thinking about Michelle.
When I'd finished I pulled the panties and tights back up round my waist and
went back to the bedroom.
I removed the skirt and a sweater from the bag. It was cold but not freezing at
this time of year so I had bought a white, thick cable-knit women's jumper and a
matching woollen knit skirt.
I stepped into the skirt and tugged it up round my hips. I fastened the button
and zipped the skirt closed, smoothing it down round my things and tugging the
hem down as far as it would go, which was not far enough to make me feel
comfortable. Not that I would have felt comfortable in a longer skirt, just less
exposed.
I pulled the jumper over my head and smoothed it down over my body, looking down
and seeing the padded bra pushing the front of it out. The sweater was tight
enough to be almost described as 'figure hugging' and clearly showed my fake
breasts, making me look more feminine.
I stood there for a few more minutes, staring wonderingly down at my body.
Except it wasn't my body. My body would be wearing jeans and a T-shirt, not a
tight-ish girl's sweater with breasts, a skirt and pretty, nylon encased smooth
legs. It was so odd seeing a girl's body where mine should be that I nearly
forgot how embarrassing this all was (even though nobody else could see me).
I looked at myself in the mirror, turning this way and that. Not quite admiring
myself but still shocked at the sight. Feeling almost voyeuristic at spending so
long staring at a woman's body. I know the woman was me, and my face and hair
gave that away, but it was something completely alien to any experiences so far
in my life.
I tore myself away from the mirror and sat at a dressing table in front of a
mirror. Michelle had given me a makeup bag to use with some of her makeup. I had
been practising so I knew what to do and could even manage to do it fairly well
if I took it slowly and carefully. It was still only half past eleven so I knew
I had an hour and a half to make sure I was properly presented as a young woman.
I took a slightly damp sponge and used it to apply a small amount of foundation
to my face. I had shaved well so didn't need much to feel confident that any
stubble was covered. Next I applied powder. The brush she had given me was huge
and actually felt quite nice on my face. I used the same brush to apply some
blusher, only a small amount, enough to highlight my cheeks and subtly alter the
shape of my face.
Carefully I applied black mascara and eyeliner, careful not to overdo the
eyeliner. Again, it was just to change the apparent shape of my face, not look
like a tart on a night out. When that was done, I applied a bit of light brown
eyeshadow to my upper lids. I made sure it was blended and matched on both eyes.
Next came lipstick. I applied it, blotted, brushed powder over it then applied
and blotted again.
I pulled the wig from the bag. It was past shoulder length, dark brown, almost
the same colour as my own hair and loosely curled so it would bounce as I moved.
I had bought it from a fancy dress shop nearby and Michelle hadn't seen it so
wouldn't be able to recognise me by my hair.
I had a pair of clip on dangly earrings, which I attached to my ears after I'd
brushed the wig out and settled it into place on my head.
Looking in the mirror again, the full length one, not the dressing table one, I
saw that I looked like a woman. I doubted that anybody would realise I was male
just by looking at me. I was not overtly sexy but neither was I ugly or even
plain. I looked kind of cute. I stood there for several more minutes,
scrutinising myself from every possible angle, trying to reassure myself that as
soon as I stepped out the door I wouldn't suddenly be harangued in the street by
every passer by for being a lad in a skirt.
I gave myself a squirt of body spray. I knew that I was going to be nervous and
decided to buy a feminine body spray to hide any sweating through panic.
A pair of low heeled court shoes, bought for me by Michelle, came out of the bag
and I slipped them onto my feet and took a few practice steps round my
grandparents' house. I also put on a pretty woman's watch.
I put the few things I might need, a bit of cash, lipstick and so on in a small
shoulder bag and tried to psyche myself up to go outside. I had purposely left
the keys to the house with Michelle so that I would not be able to leave the
house then come back in a panic and keep trying to leave, making myself more
conspicuous. I would either be here when Michelle arrived and she would have won
the bet because of me chickening out or I would be out dressed as a woman,
waiting for her in the library.
I glanced at my watch. 12:45. It would normally take me about five minutes to
walk to the library but I guessed it would take me longer in the unfamiliar
shoes and because of concentrating on trying to walk like a woman instead of
striding along like a man.
I must have stood just inside the front door for nearly half an hour, debating
with myself whether or not to leave the house. I was so nervous about being
outside trying to pass as a woman, even though I knew I looked feminine enough
to get away with it.
Finally, with a deep breath and not quite believing I was actually doing it, I
opened the door, stepped out into the front garden and pulled the door closed
behind me. I walked quickly up the garden path and on to the street. I turned
towards the library and began to walk, forcing myself to get out in public so
there was nothing I could do about it and to stop myself trying to hide behind
bushes or stay out of sight.
I had been walking for five minutes before I calmed down enough to notice the
new sensations I was experiencing. My legs were so weak I was surprised I could
walk at all. It was only after several people had passed me on the street
without giving me a second glance that I stopped panicking so much and
concentrated on trying to walk like a woman.
I was looking carefully at other women on the high street and trying to copy the
way they moved. I could feel my hairless legs, cold but not unpleasantly so
rubbing against each other through my sheer nylons. I could feel the wintry
breeze blowing up inside my skirt, again not unpleasantly cold and strangely
sensuous.
When I realised that hardly anybody was paying me the slightest attention (and
those that did were mostly looking at my legs) I began to calm down further. I
still felt scared at being exposed as a man and embarrassed at being out in
public in a skirt but it also felt like a disguise (which it was I guess). It
felt like a mask, almost like a shield, something that hid me away from public
view. I had always been fairly insecure and I guess this appealed to me in the
same way that some people do not like being seen without their glasses or
makeup.
My panic had mostly vanished by the time I reached the library but it returned
as soon as I entered. Inside there were less people so I was likely to stand out
more than I did on a crowded high street. Fortunately I was still not attracting
very much attention. I found a book and a seat, which was on its own by a window.
From the seat I could see virtually all of that floor of the library so I sat
down, crossed my legs as I had seen women do, smoothed down my skirt and opened
my book.
I kept an eye on the time and when it went past 1:30 I kept looking about to see
if I could spot Michelle. I noticed that every time I looked up there was a man
in his forties sitting nearby who was looking at me. He turned away every time I
looked up. I began to panic again, sure that he had seen through my disguise and
was about to come over and shout at me for being a freak or something.
I was so relieved when I finally spotted Michelle wandering round the library,
looking around. Grinning to myself I was careful not to look straight at her or
make eye contact, trying to look like a young lady sitting reading her book.
Michelle soon wandered off to check the other floors. Next time she passed she
looked at me with a bit more concentration but I pretended not to notice and she
walked away again.
The third time she came past I made eye contact as she checked me out and blew
her a quick kiss. She looked shocked and came rushing over to me, staring
intently at my face.
"Wow!" she whispered. "I was wondering if that was you but even though I was
looking for a woman who looked like you, I still thought I must have been
mistaken. You look so different."
Nobody was watching so she gave me a quick kiss. She sat down next to me and we
chatted for a short while. She was impressed that I looked so different and I
told her about the man who had been looking at me.
Michelle looked over and saw him staring again. She grinned and told me that he
was obviously checking my legs out. She looked down at them herself and
exclaimed (a bit more loudly than I was comfortable with), "You shaved your
legs! I can't believe you did that for me!"
"Shh!"
I looked around to see if anyone had heard. Michelle clapped her hands
over her mouth, "Sorry, Don... erm... Donna," she apologised.
Michelle reached her hand out then stopped. She looked at me and there was a
twinkle in her eyes as she said, "Your legs look great in short skirt and
tights. I really want to touch them to see how they feel. I'd better not though.
Not in public."
"So I won the bet then?" I asked.
"Oh yes! I didn't recognise you even though I was looking for you and knew you
would be dressed as a woman. If you'd walked past me in the street looking like
that I wouldn't even have noticed you."
"Excellent," I grinned, "I saw just the dress for you to wear when we go out
shopping then." I'd seen a particularly nasty seventies brightly coloured dress
while looking in charity shops for my skirt and sweater. I had bought it just in
case I won this bet.
"Can we go now Michelle?" I asked, "I'm feeling very embarrassed sitting here in
a skirt."
"Not yet, Donna. I brought some college work with me. I need to find a couple of
books here and do a bit of work then we can go. You can sit and keep me company
while I work."
"But... I know. Give me the keys to my grandparents' house and I'll go get
changed while you work and meet you back here."
She rummaged in her bag and looked sheepish. "Sorry. I think I left them on the
telephone table at your grandparents' place."
"What? Oh no! What will they say when they get back and find my clothes there
with a bag of makeup and everything?"
"Don't worry. I took all that with me, it's in the car. There's only your
clothes there and you can tell them you just popped in to get changed and forgot
them."
"But what am I supposed to wear?"
"We can go back to my place. My parents won't be back until tomorrow and you
won't be leaving until late anyway. You'll get back home after your parents have
gone to bed and can sneak in without being seen."
That was true at least. The last bus from her place wouldn't get me home until
after one in the morning. Dammit though, I was stuck in a skirt and really
didn't want to be.
We went to a different section of the library and Michelle found the books she
wanted and began her college work. I sat next to her at the table, reading the
book I had picked up. We were in a much more secluded part of the library and we
risked a passionate kiss which fortunately didn't smudge either of our lipsticks
too much.
Michelle's hand crept onto my thigh as we sat there and she caressed my smooth
skin through the nylon. I gasped slightly at the feeling and began to get hard
in my skirt. Michelle obviously enjoyed how my leg felt as her hand crept
upwards until her fingers were between my legs and under the hem of the skirt.
She looked at me wide eyed as she felt the panties and the erection inside them.
"You like that then!" she giggled and I nodded. "It feels good for me to touch
your legs as well, Donna. When we get home I'll touch them properly."
Eventually we left to go back to her house. As soon as we were inside and the
door was closed, we were in each other's arms. We kissed for minutes, enjoying
the feeling of our painted lips together. Michelle's hand was touching my thighs
and rucking my skirt up as I often did to her. It wasn't long before we were in
bed together, giving each other pleasure. We didn't even stop to undress
properly and were both still wearing our bras.
When we finished, Michelle found something else for me to wear, one of her
dresses. Before selecting it, she convinced me to try on a bridesmaid dress she
had from the year before (it was a gorgeous dark blue, Thai silk dress which
looked incredibly sexy on her. She also talked, me into trying her old school
uniform.
The dress I ended up wearing was a lilac, jersey mini dress, which looked great
on her but less great on me due to the tightness making it obvious that I was
not female!
We sat watching TV, talking, eating until it was nearing the time for me to
leave. I changed back into the skirt and sweater I had worn to the library and
touched up my makeup. We kissed some more before I left to catch my bus.
Fortunately the bus was virtually empty and again, nobody seemed to pay much
attention to me. Even more fortunately, my parents were asleep when I got home.
I got undressed and put a bathrobe on and went to wash the makeup off. It was
only as I was leaving the bathroom that I realised my smooth legs were visible
below the hem of the robe. It made me realise that I would have to be careful
about what I wore for a while until the hair grew back. It didn't make me
realise that Michelle would talk me into shaving my legs fairly often and even
wanting to do it for me in the bath. But that's all a whole different set of
stories.
The End
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