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Losing It free porn video
Losing It
By Kelly Brown
It's Sunday night. I can't sleep. Last night... I not only
appeared in public as a girl for the first time... I also
lost my virginity! I'm on a total high... as a result. In
the absence of sleep, I'm going to detail it, so I don't
forget anything. I'm changing a few names... I don't want
to embarrass anyone... but this is what happened, last
night... August 17th 2002.
***
My name is Peter... and I work for an IT company here in
London. I'm 25, and I've been crossdressing as long as I
can remember. I moved out when I was 18, after college, and
found my own place in North London. It was wonderful... I
was able to dress whenever I chose, and I went overboard. I
got catalogues, and ordered loads of outfits...
experimented... got better... got into debt!! Then I got
the job I'm in now... the money is good, and I was able to
afford better wigs and such. I'm single, it's not a
problem... I have a room for ... Kelly... and I let her off
the hook maybe once a week. (As you get able to dress
more... you get the urge less...)
I've been out a couple of times as Kelly... we all know the
score... midnight dash to the post box... heart hammering
as cars pass... desperate not to be seen... hoping we ARE
seen!! I was no exception. I do a pretty good job on the
whole... but I'm five ten, and I don't believe in all
honesty that I could pass close up.
***
Three weeks ago... our company won a contract that will pay
a VERY hefty sum over the next five years, and guarantees
all our jobs for that time. We were all over the moon. The
CEO asked me to organise a party as a reward... big... he
suggested. I hired most of the rooms at a country hotel,
just off the M25... for last night, and organised a
disco... and buffet. One of the girls at work suggested a
themed fancy dress party... everyone was up for it... and
the consensus was Pop Idols. A few people were
disgruntled... said they had no imagination, and wouldn't
be able to think up characters. I suggested we put the
names of thirty (the number in the company) stars names in
a hat... and I would draw them out and we would go as that.
There are 18 men, and 12 girls work here... I basically put
down all the guy stars on blue paper... all the girl stars
on pink... then put them into a hat and drew them out for
each.
While I was doing it... i had a wild notion... and decided
on a whim to go with it. If it came off... it would be
fun... if it got dismissed... nothing lost. I called out
the names as per... until I had two papers left... one
blue... one pink... and myself and a secretary called Dawn,
left to be given characters. Shaking a little... I
announced very authoritatively (and hoping that someone
would jump in) I shall be coming as... I dug into the bin
and drew out the pink paper... making sure it looked as
though I hadn't paid enough attention... Britney Spears!
Huge laugh... then sure enough, Jack my so-called buddy
called out... Yeah!!! Do it!!!! I laughed... and muttered
come on... you wouldn't make me do that for a simple
mistake?! Now everyone joined in Yes!!! Dawn pulled out the
last blue slip and chimed in... and I'm coming as Michael
Jackson!! Lots more laughter. Looking pained... I nodded
okay... okay... anything for a laugh! Deep down... I was
almost about to pass out... it had worked. Better than I
could have hoped for... yes I could fiddle the paper... but
I hadn't known who I'd draw... and I'd gotten Britney!!! I
was over the moon.
The rest of the day was a blur... people making comments
about what a sport I was etc, etc... if only they knew!!
The next few days passed in a whirl... and I spent time
working out my costume.
I really fancied trying Britney's red PVC catsuit look, but
realised I would have trouble finding one... and also it
would be red hot. So I settled for the schoolgirl 'Hit Me
Baby' look. Hair was no prob... I had a medium length
blonde\brown wig... and I managed to find some pink furry
hair bands at the local chemist. I had a white shirt that
had shrunk a little in the wash... and tied up under my
breasts would do fine... the skirt was fairly easy... I got
a short black kilt ordered from the Catalogue... the grey
cardigan, I ended up going to a school supplier for my
sister, and got one a couple of sizes too small... it
worked perfectly. Stockings, I improvised... got a thickish
pair of black hold ups, and cut them down, and re-sewed the
tops... this way, they held up fine, and came to just below
the level of my kilt, about an inch of bare flesh.
Underwear was a black lace push up bra, and matching
panties. Shoes, I had to hit a specialist TV shop in
London, and got a pair of black Mary Janes... I was a
little worried about flashing my belly... normally I wear a
corset, and can achieve a decent 27 inch waist... without,
I was going to be just under 30... but I had to go with
it...
I put it all together one evening... savouring the look...
okay... no way I looked like Britney... but it was obvious
who I was MEANT to be, and most importantly... I looked
like a GIRL going fancy dress... I was elated.
I couldn't wait for the party... each day dragged by...
everyone at work talking about getting their costumes
together... my friend Jack, was doing Bowie... and couldn't
decide which look to go for. In the end, he decided on the
Thin White Duke look, and set about getting it together.
Yesterday finally arrived... and as I set off for the hotel
at around 1pm... I was as nervous as hell. I suddenly
started to get cold feet, and when I checked in, began to
think I might pull out. I carried my suitcase up to my
room... ran a bath, and then popped down to check on
everything. The function room was looking great... very
festive... buffet tables laid out... and the DJ had already
set up his sound system... We chatted, and he asked who I
was going to be that evening, as he'd been told it was
fancy dress. I groaned... Britney Spears... he laughed... I
think he thought I was joking. I went back upstairs...
saying hi to people as they arrived. I had my bath... and
took the opportunity to shave again... I enjoy those
languid baths, running the razor along my legs... keeping
them smooth... I'm lucky. I'm not too hairy... legs and
underarms... and I also keep my bush trimmed.
I checked the clock... 6pm... we were due down at 7... I
couldn't put it off much longer... so I laid my clothes out
on the bed, and started on my makeup...
Base foundation first... a little darker than normal, for
that Californian tan look... Then more eye makeup than I
would normally wear... smoky greys... eyebrows brushed into
place and drawn in... mascara coated... there was a knock
on the door... I answered it... it was Jack. He chortled
when he saw my makeup... we had a quick chat, he explained
that he might have to rush away, as his wife wasn't well,
and he possibly had to go back to London. Did I mind if he
didn't wear his costume... Seemed reasonable, and I was
pleased he'd thought to ask. He left.
I went back to my makeup... eyes were ready... blusher...
and deep ruby lipstick. Then I carefully pulled my wig into
place, and got my pigtails ready with the pink furry
scrunchies, took a while as my hands were trembling... I
sat back to see how I looked... good. As I said... not
Britney... but I looked pretty. If I was to see myself in a
bar... I wouldn't automatically think "man"... and for
that, I was grateful.
I went to the bed, and took off my robe. I pulled on a
tight, flesh coloured G-string, and pushed my balls back
between my legs... it's gotten easier, and isn't as painful
as it used to be... still smarts though!! Then I pulled my
black lace panties into place, enjoying the flat front they
gave me... I slipped my bra around my waist and fastened
the strap, pulling it up and putting my arms through, and
settling it in, feeling the underwiring, biting into my
chest. My breast fillers were next, and though they were
obvious now... they'd be hidden when my blouse was on. I
slowly put my foot into one of the stockings and drew it up
my leg... and followed with the second one. I was starting
to relax... blouse next... unbuttoned a little, and the
tails tied under my bust. Over that the tight grey
cardigan... sleeves pushed halfway up my forearms... then I
stepped into the skirt, and adjusted it to get just the
right amount of bare skin above my stocking tops on show.
Then I stepped into my shoes, and checked in the mirror. To
say I was pleased was an understatement. I looked... good!
As I said before... I looked like a girl... pretending to
be Britney... okay... get close, or hear me speak, and the
illusion wasn't so good... but overall... :))
I checked my watch... it was time to go down... I started
for the door... then panicked. Stopped... opened the fridge
and had a coke. Suddenly I started to think I was making a
huge mistake, and should get changed again. I sat on my
bed... sipped my coke. I could hear people in the corridor
going down... laughing. I checked through the spyhole...
first past was Cher... (Karen)... looking pretty good...
she was accompanied by Jackie as a not so slim Kylie...
Behind them was Hugo from the office next to mine as Robbie
Williams... he'd gone for the Let Me Entertain You look...
tight black catsuit and makeup... I started to feel a
little better... it was only a party after all.
I checked my mirror again... pouted a bit... then realised
I had to go. I was starting to sweat a little... that "cold
trickle" that most cross dressers will remember!!
I breathed deeply, got my key card and slipped it along
with some cash into a little hand purse, and opened the
door... no going back. I closed the door... and headed for
the lift. The corridor was empty... I walked along... aware
of the deadening effect of the carpet... and a slight chill
on my bare legs above the stockings. Nice... :)
I pressed the button to call the lift... and watched as it
came from the floor above. The doors opened... ooops...
people inside. Two youngish guys... and behind them...
Phil... our accountant. Older than most of us... late
thirties... and pretty shy. He was done up as... well he
was SUPPOSED to be Mick Jagger... but he was wearing a
double-breasted grey suit and a trilby. I stepped into the
lift... worried about the reaction from the two guys I
didn't know... they moved aside, Phil waved... Peter...
looking good... okay... so I didn't REALLY think the two
guys would be fooled, but I 'm allowed to dream... :) Not
any more. They were quiet all the way down... my heart was
still thumping... and I remember making some loutish
comment about how it was the last time I screwed up and had
to pay the consequences...
The lift stopped in the lobby, and we walked across to
where the function room was... I was aware of stares from
the girls on reception, but was beginning to relax... a
little. I asked Phil about his costume, and he said he felt
too old to do Jagger... so he's come as Sinatra... I took
his word for it. At least he'd tried!
The function room was heaving... almost everybody was
there... along with friends or partners... probably 60 or
70 people. Most of those who didn't work at the office, had
had a go at fancy dress too... and I spotted one other
Britney... she'd gone for the same look... but at the risk
of vanity... I looked better... :)
Pete!! I looked over... it was Jack... sure enough... no
costume... he came over... hey... you look... he stopped...
I raised an eyebrow. He didn't say any more... just looked
a little quizzical, and asked what I wanted to drink... I
said vodka and tonic, and he wandered off.
It suddenly hit me... like a hammer... I was in a room full
of people, and I was dressed as a girl!! I was elated... I
walked across to find a stool to sit on... exchanging hi's
with various friends, and getting generally good comments,
including my favourite... from our receptionist Hels...
you've got GREAT legs! I found a stool, and sat... aware of
my skirt riding up over my thighs... exposing flesh... Jack
brought me my drink... and we chatted a little... though it
was hard to hear really.
Over the next couple of hours... I had a few more drinks
than I normally do... and really got into the swing. I
remember that I danced with the girls a lot more... and
that my style of dancing was very different... I used my
arms a lot more, as well as my hips.
I was having a ball... and it was late when I realised that
a lot of people had drifted away... I really didn't want it
to end... I was more than a little "merry"... and sat down
to stop my head spinning. The DJ was announcing the end of
the evening, and I was chatting to Hels... Careless Whisper
started up... the last slow dance. Hels' boyfriend
wandered... well... staggered across and dragged her onto
the floor. I watched... then heard a voice say Come on
Britney...
I turned... it was a guy called Rob... we'd chatted earlier
in the evening... he was a friend of one of the buyers... I
remembered because he was tall... easily six four. I
realised he was asking me to dance... I giggled... and
muttered something... can't remember what... but he was
laughing and pulling my arm... and I gave in and wandered
onto the floor... everyone there was swaying to the number,
and I let him put his arms around my waist, and swayed
along... laughing... it was all a joke... right...
He pulled me a little tighter, and it was hard not to put
my head into his shoulder owing to his height... after a
second or two... I realised what was happening and pulled
away... here I was dressed as a girl... slow dancing with a
man! I went back to my stool as the DJ was saying good
night, and the lights were starting to come back on... I
realised the night was over... and I'd have to go back to
my room, and get changed. I was gutted... I wanted it to
last forever. I lingered as long as I could... chatting to
the DJ... making sure he knew where to get paid etc... then
sighed... no choice now... back to my room.
As I crossed the floor, I spotted Robert waiting. He
waved... we chatted a little, and he told me he wasn't
looking forward to the drive back to London, and really
needed to sober up a little. I suggested 9and I SWEAR this
was literally ALL I meant) that he come to my room and we
could have coffee... he nodded, and I led him to the lift
and up to my floor.
I've thought it over a lot in the last few hours, and I
suppose deep down I WAS leading him on. Firstly... when we
went into my room... I didn't put the main light on... and
put the radio station on the TV.
Then I rang room service and asked for a large pot of
coffee. When I hung up, I slipped my shoes off... and
curled my legs under me on the bed. Robert was sat in the
easy chair by the television. Watching me. We talked
generally... and I asked him to get the coffee when the
waiter knocked. As we were drinking it...
I saw him smiling at me. I asked what's up? He said how
often do you dress up? I was gobsmacked... I flustered
laughing saying I don't... it's a party he nodded and said
yes... but you do it a bit too well... all the girls at the
party were saying so Now I was worried... I could feel
myself shaking. What an idiot I'd been. I shook my head...
he smiled again...
Then he said I noticed when you were dancing... you bent
over at one point, and I saw your knickers... Costume ... I
said. Nah... a guy would just wear Y fronts... no one would
be seeing them... I had no answer. He shrugged. It's not a
problem... really... its cool... I nodded. Besides... you
look pretty good... Now I smiled.
We carried on sipping coffee... chatting generally. He was
a nice guy. Looking back I realise that all the time... I
was taking a girls role though I didn't really notice it at
the time. Later Robert said... you could have changed out
of the clothes you know... Then he smiled again. I just
shrugged... I checked the clock... it was 3 am... just
after. Robert stood up and said, he ought to get back to
London... I asked if he was sober yet, and he said probably
not. I said he should book a room... but he said he was
skint. So... I suggested he stayed in my room. We made the
usual joke about a line of pillows down the middle of the
bed... and I said he could use the bathroom first.
As I stood to get the bed ready, Robert stood too... and I
remember exactly how he said it... I've gone over it so
many times in my head... every guy's fantasy to sleep with
Britney... any chance? I just stared at him... my tummy was
doing summersaults... he was coming on to me... okay sop
we'd had a lot to drink... but... he approached me, and put
his arms around my waist again... then he leant forward and
kissed me.
First time I'd ever been kissed by a man. I was stunned. He
was stubbly... and I kept my mouth shut... but I didn't
pull away. He looked into my eyes... pulled me tighter, and
kissed me again... I gasped a little, then felt him
pressing more, and I opened my mouth and kissed him back...
feeling a mans tongue in my mouth... it felt HUGE in
relation to a girl's.
His hands were moving over my back and I felt him cup my
bottom... stroking through my skirt... I tried to do what a
girl would do... stroking his neck as we kissed... then his
hand was under my skirt, stroking my bottom through my
panties... one finger pressing against my hole... I pulled
away... frightened...
Robert stopped and held his hands up... he apologised... I
explained I'd NEVER kissed a man before... and we talked a
little... Rob said that he'd had a few experiences with
men... and it was fine if I didn't want to go any further.
God I was all over the place... I truly didn't know what I
wanted.
At Rob's suggestion, we turned the light off... he stripped
down to his shorts, and I kept my clothes on. We lay down
on the bed in the darkness and chatted... then we went
silent. I began to think he'd gone to sleep. At that point
I realised that I DIDN'T WANT him to go to sleep... so I
started sighing as I couldn't sleep... eventually he
giggled in the dark, and I punched him... he rolled over,
and was on top of me... this time, I responded to his
kisses... passionately...
I felt his hand under my skirt again, and I adjusted my
position to accommodate him... as he stroked the front of
my panties, my insides were on fire, and I let my hand slip
down to his shorts. He was erect... I swallowed hard, and
started to rub him through his shorts... I don't think I
was very good... but he was groaning... and whispering
encouragement in my ear... he undid the buttons on my
cardigan, and then my blouse, and sat me up... I slipped
them off... I remember he was behind me, and sneezed from
my pink scrunchies...
We laughed then he had me slide my skirt off... we lay back
again, and I felt him taking off his shorts. As we kissed
again, I now took hold of his cock... it was weird... I'd
only ever felt my own before... i wanked him slowly... he
whispered if I wanted him to free mine, but I said no... at
that moment, I wanted to be a girl. He kissed my neck,
sending tingles down my spine... and I carried on wanking
him...
We carried on like this for a while, then I felt him shift,
and sit up, then he was sat on top of me... stroking my
"breasts" and kissing me deeply. In the dim light, I saw
him sit upright... and lean forward... and I could just
make out his cock... I knew what he wanted me to do... I'd
done exactly the same thing to girls myself. I paused... I
said I'm not sure I can do that... He laughed and said that
was okay... and slipped off me... I could tell he was
disappointed. We broke off for a while and had a coke...
then we climbed back onto the bed, and he stroked my
legs... I was in heaven...
I started to play with him again... then thought sod it...
I need to try... and I slid down his body... he adjusted
himself, and in the darkness, I took his cock in my hand
and slowly put it to my lips. The smell was unusual to say
the least... I flicked my tongue at it... salty... not
unpleasant... I put the tip into my mouth, and held it
there. Robert went very still... I sucked a little and he
groaned... I carried on sucking... he was groaning away...
and I was pleased that I was pleasing him...
I felt him grab my pigtails and start to fuck my face, and
we had to stop a few times while I got used to it...
eventually, I felt him begin to tense, and I knew he was
going to cum... he kept hold of my pigtails, and I started
to pull back... he said something about ... in your
mouth... but I panicked and pulled back, as he started to
cum... he exploded... and I felt him spattering my
"breasts" and neck... part of me was disgusted with
myself... another part over the moon... as he finished...
he pulled me to him, and kissed me passionately.
He lay me on my back, and lay on top of me again... he said
he really wanted to fuck me, but we had no rubbers... so we
kissed more and as he got harder... he lay on top of me,
and I wrapped my legs around him as he humped me... it felt
like all the worlds as though I was being screwed, and the
friction as my cock was pushed back beneath me was too
much... eventually I felt myself cumming... moaning and
nuzzling his neck as I did.
We got cleaned up... and eventually fell asleep wrapped
together... him naked, me in my bra and panties.
This morning, I think we were both very embarrassed, and
didn't say much as he dressed and left. When I looked in
the mirror, I was a state... make up smeared all over...
and the remains of his explosion still on my bra.
Tonight... back at home... i STILL cant believe I went to a
party as Britney... and ended up giving a guy a blow job.
Will I do it again? God knows... I was excited as all
hell... I don't think I'll go looking, but I also doubt I
would turn it down if it arose again.
***
Any comments... please email me at [email protected]
xxxx
Virginia
- 16.06.2020
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