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Date: Thu, 30 Nov 2000 22:20:50 -0000
From: Caroline Bradley <carolinejuk@hotmail.com>
Subject: Room Service - a TG story
Room Service
By
Caroline Jane Bradley
"Good evening Mr. Deveraux, here for another week? I'll check you in to
your normal room", Sally the receptionist smiled as she printed out the
form and handed it to Simon Deveraux across the busy check-in desk of the
Stakis Country Court Hotel in Bromsgrove, West Midlands.
The check-in formalities briskly completed, Simon picked up his computer
case and suit carrier and walked quickly through the entrance foyer of the
hotel smiling at the familiar faces of the staff as he made his way to room
224. He had been staying at this hotel for four weeks now, Tuesday though
Thursday, as his new job meant he had to stay away from home. Relocation
was out of the question as his daughter's school was one of the best in the
country and his wife had said that they needed to keep their roots where
they were.
The electronic key opened the door to a well-appointed bedroom with a large
double bed, separate en-suite facilities and a small sitting area with
sofa. He unravelled his suit carrier and hung it up in the wardrobe,
slipped out of his jacket and tie and ran a bath, pouring in the entire
sachet of hotel bubble bath. Dialling "0" on the room 'phone, he ordered a
light salad and a glass of Australian Chardonnay before returning to the
bathroom to check on the temperature of the bath water. He had fallen into
a routine in the last few weeks and knew that he had enough time for a
close shave with his razor followed by a warm wallow in the tempting bath
before the food would be delivered.
Sure enough, glowing from the hot bath and with a towelling dressing gown
wrapped around him, there was a knock at the door and another familiar face
greeted him as the food was delivered and signed for, he remembered to give
the waiter a tip. Sitting on the sofa, he ate the meal and sipped the wine
whilst watching a mind-numbing episode of his wife's favourite soap opera.
Relaxed, fed and warm, he padded quietly to the hanging wardrobe and opened
the suit carrier; from an inside zipped pocket he withdrew a make-up bag
and some fresh underwear.
The next two hours were spent in Simon's favourite activity; the slow,
delicate and very sensuous process of converting from the harassed
businessman to a suave, sophisticated woman. He always kept his legs and
torso hairless, having convinced his wife a number of years ago that the
Andre Agassi look was sexy. His face was not too masculine and, at just
over 5' 8" and 150lbs he had a fair figure. All this helped the
preparations without arousing suspicion.
The regular visits to the hotel had allowed him to build up a small cache
of clothing and make-up from visits to the local shopping area. More
specific items, like wigs and breast forms he had ordered over the Internet
and had delivered to the hotel. This particular evening, he had bought a
smart black business skirt/suit and a white silk blouse from the nearby
Marks & Spencer store. With his preparations complete, he pulled on the
blouse and zipped up the skirt, aligning the back zipper and lifting the
skirt to pull the blouse down into shape. Slipping his black stocking-clad
feet into his best pair of black patent court shoes, he sat in front of the
mirror and applied glue to a set of stick-on nails. Once they were set he
shaped them carefully before applying a single coat of nail varnish to
match the deep burgundy of his favourite lipstick.
A few minutes later, he was admiring the reflection in the full-length room
mirror. The new suit fitted very well, the jacket accentuating the curves
produced by the light waist clincher; the skirt following the contours of
the hip-enhancing girdle. His fingers sparkled from the fresh lacquer and
the four rings adorning his fingers; his throat shone from a heavy gold
necklace, which moved as, shaking his head, the long tresses of his black
wig revealed a sparkle from the gold loop earrings. With a final check of
his carefully-applied but subtle make-up, he spritzed perfume behind his
ears and, seductively, up his skirt.
Walking across the floor of the bedroom, he basked in the delicious feeling
of the nylon stockings as they brushed together at the top of his legs and
the swish of the tight skirt as he walked. This was the climax of his
evening and he felt the insistent pressure from his member as it grew in
response to the feelings of excitement. Walking slowly over to the
bathroom, he watched his painted fingernails search below the material of
the skirt and lift up the leg of the girdle to release his pulsing manhood.
Transferring his gaze to the face of the beautifully made-up dark-haired
woman staring back at him with pursed red lips, he started to stroke his
manhood with the long fingernails. Carefully moving the material of the
new skirt he stretched upright in the black heels as, with a grunt, he shot
his load across the bathroom basin and onto the mirror.
Meticulously, he cleaned the head of his penis with a tissue and
repositioned it into the waiting underwear. Cleaning his hands, he lifted
his skirt and slid the girdle and black lacy knickers down to his ankles,
glancing into the mirror he saw black stockings and suspenders with a
slowly subsiding member and red fingernails holding up a black skirt. The
view entranced him and he swiftly grasped his member giving it a few
powerful strokes before another load of ejaculate shot into the handbasin.
He moved over to the lavatory and sat down, using the toilet tissue to
clean himself. Reaching across to the conveniently- provided dispenser he
removed a sanitary towel, placing in into the crotch of the black knickers
before standing and pulling them up tight, entrapping his member between
his legs.
Washing his hands once more before pulling up the figure-enhancing girdle,
he smoothed down the skirt and looked once again in the mirror. The frank
gaze of a sophisticated woman returned his stare and he smiled, touched up
his lipstick, and returned to the bedroom. The rest of the evening was
spent completing some unfinished work from the previous day; he loved the
thought that no-one would guess that his diligent efforts in the evening
were accomplished dressed like he was now. Work completed, he returned to
the bathroom and stripped down to bra and pants; carefully tissuing off the
make-up and cleansing his skin properly, he applied a night moisturiser and
fresh lipstick before slipping into a full-length peach night- dress.
With the alarm set for 07.00, he slid luxuriously into bed. Glancing
across the room into the mirror, he saw his fantasy of the woman of his
dreams readying herself for bed. The satin feel of the night-dress and the
smell of the perfume heightened his senses, he could feel his member
awakening from its earlier efforts and he slowly slid down into bed,
closing his eyes as his fingers gently stroked the bulge in his black
knickers. As the tension heightened, he rolled onto his front so that, by
moving his body, he could feel the soft movement of the satin on his crotch
and the weight of his breast forms felt comforting. Reaching over to the
bedside table, he deftly removed a condom from his wallet, rolling onto his
back he released his penis from the embrace of the black nylon and swiftly
rolled the sweet-smelling rubber over his erect form.
The final orgasm of the night was a slow, sensuous affair. Rearranging his
underwear and night-dress, he lay on his back on the bed with only the
tell-tale bulge affecting the feminine look. He switched the TV over to
the adult movie channel and selected a programme showing a number of naked
women and men arousing themselves. As the crescendo from the TV increased,
so did the speed and pressure of his hands moving over the growing bulge in
his night-dress. The combination of sounds, sights, smells and feelings
eventually overwhelmed him and, just as the TV showed semen spurting into
mouths and vaginas, so his own erupted into the embrace of the condom.
Exhausted, he slowly got up and went to the bathroom, flushing the used
condom away and cleaning himself before nestling his abused member once
more into the soft material of the underwear. A final straightening of his
night-gown and a refreshing retouch of his lipstick, he returned to bed and
fell sound asleep.
The alarm interrupted a pleasant dream and Simon slipped out of bed,
stretching luxuriously as he caught his reflection in the mirror, the wig,
breast forms and long night-gown giving the continuing illusion of a tall
slim woman. He opened the curtains and, as the daylight flooded into the
room, called out,
"Can you leave it outside please?" as a rap on the door announced the room
service breakfast. Slipping on a matching negligee he carefully opened the
bedroom door and slid the tray into the room, catching the admiring glance
of a passing businessman as he walked down the corridor. Breakfast
completed, Simon reluctantly took off wig, night attire and underwear and
carefully hung the items up in the wardrobe. Removing the sanitary towel
from its place in the crotch of the knickers, he flushed it away and
dropped the soiled underwear into the washbasin. Running in hot water he
gently washed the marks away with soap before hanging the knickers up on a
rail conveniently provided over the bath.
Concentrating on his face, he carefully cleansed and moisturised; paying
particular attention to his eyes by using a cotton bud to remove the last
vestiges of mascara and eyeliner. A shave and shower, the latter in the
hotel's shower foam, followed by a brisk towelling and he was ready to
return to being the efficient businessman. He checked the recently-bought
items and returned the suit to a carrier bag, he would keep the blouse
which he hung in the suit carrier. A swift check of the room to ensure the
cleaners wouldn't find anything too incriminating and he left for the
office.
That evening, he returned to the department store and exchanged the suit
without fuss - that was the great thing about these stores, you could try
the clothes on in private and then return them after having some fun! He
browsed the aisles without success and moved on to another late-opening
women's store where a short dress caught his eye. Ten minutes later he was
back in his car with the new purchase on the back seat, he drove back to
the hotel and began the night's ritual.
This time, after the bath and a snack, he spent some time carefully shaping
his toe-nails before applying two coats of a brilliant red varnish. Whilst
this was drying, he sat at the dressing table and meticulously applied his
make-up, choosing a very light shade to make his skin seem pale.
Subtle frosted greys and blues accentuated his eyes as he applied a vivid
blue mascara and a deft touch of light blue eyeliner; then with practised
ease he wetted a pair of soft blue contact lenses and touched them into
place. Without looking up, he pulled a blonde wig off the stand he had
used to brush it into shape earlier, fitting and pinning it into place he
looked in the mirror as he applied the final dabs of translucent face
powder.
With lips carefully relaxed, he outlined their shape with a natural
coloured liner and gently brushed a vivid pillar-box red lipstick onto
their surface. Admiring the reflection of a pretty, blonde, blue-eyed
woman he finished the preparation with long black earrings and matching
beaded necklace.
Black lacy bra, matching knickers and the inevitable figure-enhancing
girdle followed. Then sheer almost white-coloured tights, the new dress
followed slipping into place and the zipper slid well up to the base of the
back of the neck. The black court shoes were the only choice with this
outfit as he applied the glue to the nails, pausing to carefully apply a
coat of the same vivid red nail varnish. Standing in front of the mirror
Simon admired the view; long blonde tresses framed a pale face with a
perfect complexion highlighted by blue eyeshadow and a pink blusher. Red
lips parted in a smile, blue eyes glinting with black earrings and
necklace. The dress was a superb fit, almost nude in overslip with a black
lace cover hinting at the delights below. Long shapely legs encased in
sheer nylon into black patent court shoes. He reconsidered his shoes,
removed them and zipped on a pair of knee-length black leather boots with
3" heels - the result was excellent and he twirled with delight into the
mirror.
A final touch of lipstick with a gloss of Vaseline to the centre of the
upper lip to enhance the effect, Simon could feel his member growing with
the realisation of his best-ever feminine illusion. The soft rustle of his
dress as he moved to admire the refection in the mirror was heaven, he
pranced around the room revelling in the wonderful feelings and sounds of
being a woman. Then an ear splitting noise hit him like an almost physical
blow, wrenched back to reality he realised that it was the fire alarm - oh
shit! Staring at the wide blue eyes in the mirror he rapidly assessed what
to do, maybe it was a false alarm? No, he could hear other doors opening
up and down the corridor and rushed footsteps went past the door.
A rap on the door was followed by "Fire Alarm, please leave your room
immediately and follow the signs to the safe point".
Simon moved quickly, he grabbed his long overcoat and pulled it over the
dress, remembering to fold it over in the opposite way to normal. Securing
the belt by tying it around his narrowed waist he extracted a handbag and
dropped the room and car keys into the empty bag, followed by his lipstick
(just in case!). Taking a deep breath he opened the room door to see a
number of people walking past, intent on leaving the building. With
pounding heart he followed them, the unworn soles of his boots slipping
slightly on the carpet. He smiled as a man held the fire escape door open
for him and he stepped out into a blustery evening, the wind catching his
coat and lifting it to give the man a glimpse of long nylon-encased legs.
Walking swiftly down the stairs, he joined a crowd of people as they milled
around the car park - Simon was petrified, he had never gone out en femme
before and was absolutely sure he would be recognised. However, the crowd
were generally jovial despite the windy early evening, and the light was
fading fast. He stood quietly in a small group of women, who were chatting
and passing lewd comments as the firemen arrived in their Tender, Simon
forced a smile.
After a few minutes, a receptionist with a bull-horn announced that it was
a minor fire in the kitchens and all was well. She thanked everyone for
their patience and said they could all re-enter the hotel. As the crowd
surged forward, the man who had held open the fire escape door brushed
against Simon and said, "Well, that was exciting, what's next I wonder?"
Simon smiled and shrugged his shoulders in an attempt a non-communication,
but the guy would have none of it. He chatted away without waiting for any
response and, as they entered the glare of the brightly-lit reception area,
he turned and said,
"Would you like a drink to warm up after that cold wind?" Simon could do
with a stiff drink, but not because of the cold. He shook his head as
demurely as possible and, thankfully, the man walked away. Stepping
carefully, Simon set off across the foyer towards the stairway, he
desperately hoped that the strong lighting was not going to give him away,
when he felt a pressure on his let arm,
"I'm sorry about that madam, I know most business women want to be left
alone and that sort of guy can be a nuisance. I'm Anita Ward, the Hotel
Assistant Manager, I'm sorry but I don't know your name". Simon knew full
well whom she was as they had often spoken before when he was checking in
or out, he thought quickly and summoned a husky quiet voice, "Hello, I'm
Stephanie Deveraux, my husband stays with you and I'm using his room - he
went out".
"Well, Mrs. Deveraux, we know your husband well, he is a regular. Here,
please let me get you some coffee or a drink to apologise for the
inconvenience, after all, we don't meet our client's other halves very
often". Without waiting for a reply, Anita guided Simon by the arm to a
small table in the bar and sat down opposite. A waiter appeared promptly
and, when asked what was wanted, Anita ordered two brandies.
"Here, take you coat off, it's quite warm in here", Simon acquiesced
reluctantly and immediately felt eyes swivel to the long legs and shapely
form as the coat fell from his shoulders. "What a lovely dress, where did
you buy it?" Simon shyly mentioned the local store at which point Anita
launched into a long diatribe on the variable nature of the local clothes
shops. Eventually, brandies drunk, Simon breathed a "Thank you" and got
up, feeling the eyes returning to his shapely legs - he enjoyed the feeling
immensely.
"Well, Mrs Deveraux, it was good to meet you. I hope we see you again,
good night". Relieved, Simon walked slowly to the stairs and along the
corridor to his room. Collapsing exhausted but elated on the bed he smiled
to himself. The rest of the evening fell into its normal pattern - a
retouching of hair and make-up brought back the desire and he shot himself
off in front of the mirror. His routine with the condom and the X-rated
film over he fell into a deep slumber and awoke the following morning to
return to plain old Simon and to pack his bags as this was the last night
this week.
Checking out, he saw Anita who came over to him,
"I saw your wife last night, is she here, I would just like to say goodbye"
"No, she left very early this morning, but she asked me to thank you for
the kind hospitality"
Simon thought he saw a glint in Anita's eyes as he walked out of the hotel.
The following Tuesday he checked in uneventfully, but this time was
allocated a different room to the usual.. Opening the door, he smiled - it
was a suite! A huge bedroom, separate en-suite with whirlpool bath and a
large sitting room lead to a small dining area. The decor was clearly
designed to be luxurious and he noticed a bottle of Champagne in an
ice-bucket next to the bed. A note by the bottle read, To Mr & Mrs
Deveraux from Anita, enjoy your stay.
Simon ran a hot bath and ordered from room service, he lay in the bath
enjoying the jets of water from the Jacuzzi when the doorbell rang.
Donning a dressing gown, he opened the door expecting the food delivery.
Instead Anita stood there with his order on her arm,
"I'm sorry, I'd hoped Stephanie was here, but here's your dinner. Enjoy."
Before he could respond, she walked out and pulled the door closed.
Simon ate the meal and then proceeded with the ritual of turning into
Stephanie, as he called he female alter-ego. This evening he wore a new,
long, cream sleeveless cotton dress with a matching over-blouse; tan
stockings and tan ankle-strap shoes. A mid-brown shoulder-length wig and
brown eye make-up with a dark burgundy lipstick finished the preparations.
He walked around the sumptuous apartment, swaying his hips and admiring the
swirl of the fabric as it followed his movements. Standing in front of the
large full- length mirror in the sitting room, he first opened and poured a
glass of Champagne, downing it quickly. Reaching up under the full skirt
of the dress he freed his powerful erection and ran his manicured, painted
nails over the throbbing shaft until his ejaculate poured into the waiting
glass.
Satisfied, he rearranged himself and glanced at the glass in his hand, with
a gesture of toasting himself, he put the glass to his lips and tasted his
own ejaculate as he drank the glass dry with relish. He had just recharged
the glass with Champagne when there was a knock at the door, a quick check
of the spy-hole revealed Anita standing outside. She knocked again and
then, before he could think, the door opened - she had used her pass key.
"Stephanie, I like the change in hair colour. How are you? Your husband
said that you weren't here and the girls on reception haven't seen you come
in." Anita stood there smiling, "Well?"
Simon was like a rabbit caught in powerful headlights "I, I I..he
stammered"
Without responding, Anita walked over to the large television in the
room, turned it on and inserted a video into the player installed beneath.
Simon watched in horror as the screen flickered and then sprang into life,
showing him as he was ten minutes ago, firing his ejaculate into a glass
and then apparently toasting the camera as he drank the glass dry.
"Well, I think you'll have some problem explaining this to your employers."
Anita was grinning broadly, "I must say you make a very passable woman but
your walk needs some work and your voice is a give- away at close
quarters".
"What, what are you going to do? Give me that video, I'll pay you".
Simon's voice quavered. "Stephanie, you don't mind if I call you Stephanie
as you are dressed like Stephanie - by the way, love the dress, we must go
out shopping together. Where was I, oh yes, this is not the only copy of
the video. We've had our suspicions of you and the underwear drying in the
bathroom last week was a bit obvious. Never mind, you're secret's safe
with me - I've always wanted to get to know a cross-dresser."
Simon relaxed a bit and, with great presence of mind, offered Anita a glass
of Champagne. "I'd rather drink it from the other glass," she said with a
smile, "listen, I have a proposal. I've got enough video evidence to
destroy your career here and I know your home address, what would wifey
think?"
"Please don't tell them, or her. What have I done wrong?" Simon pleaded
"Nothing, really. But, to my proposal, you clearly enjoy the dressing up
and I'm willing to help you to store your clothes here and to buy more for
you so you can indulge your little fantasy. I don't want to lose your
custom, nor that of your firm, but I do need to increase the hotel's income
to meet my bonus this year. So, you have this room every time you stay
here, you dress and perform your routine just like you have done this
evening and I will video the entire event to be screened on the hotel's
adult channel at a premium rate for punters. Eventually, they will all get
to hear of the live adult line and our takings will soar"
"But, I'll be recognised," Simon shouted, "Not with the lighting in here
and your make-up's really good. Just make sure that you don't look into
the main mirror until you've completed the transformation. Now, one final
thing, we often have a number of women guests here who ask, discretely, for
introductions. I'm assuming that you are not averse to helping them in
their fantasies - at a price which we will split 50:50?"
Simon stood wide-eyed and started to say something, Anita put a carefully
manicured finger against Simon's lipstick, "Could you handle men as well?"
"Absolutely not!", he recoiled "Shame, you could get a lot from the bored
businessman tired of the cynical whores we get here", Anita seemed
genuinely disappointed.
Before he could utter a response, Anita moved over and kissed him full on
the lips. The effect was electric and they began to caress each other as
their lips remained locked; Anita pushed him away and smiled, "Wait here
and tidy up your lipstick, I'll be back", she quickly primped her hair in
the mirror and walked out of the room.
Simon was in a whirl, he checked his make-up in the mirror, grinning at the
smeared lipstick, which he quickly repaired with a tissue and freshly
applied colour. Moving as if in a trance, he went to the bathroom and
removed the figure-enhancing girdle and rearranged himself, straightening
the knickers and suspenders. Smoothing the dress down, he carefully
brushed his wig and reapplied perfume - paying particular attention to his
groin.
There was a rap at the door and Simon opened it quickly. Anita had changed
out of her manager's "uniform" into a soft cotton dress. They embraced
immediately and Simon felt Anita's hands caress his stocking-clad thighs,
her fingers tracing slow circles as they slid upwards on the nylon lifting
the hem of his dress as they ascended. Simon was in heaven, he had always
fantasised about being made love to whilst dressed - he had tried a few
times in the early days of his marriage, but his wife wouldn't play along.
He remembered a painful moment when he had lured her to bed and she had
discovered that he was wearing her underwear and pantyhose, she laughed at
him and walked away.
Now, he could see his reflection in the mirror as a dark-haired woman was
kissing his ears and neck whilst holding and caressing his breasts. Anita
moved and unzipped the dress, letting it fall to the ground to reveal the
matching underwear, stocking, suspenders and high-heeled shoes. She then
removed her dress, under it she was naked! Taking Simon's hand she pulled
him onto the sofa in the sitting room and sat him down, without talking she
moved her head down to his legs and began to kiss the inside of his exposed
thighs; Simon lay back onto the fabric and began to moan with pleasure.
Anita reached the hem of his underwear and, with a swift movement, released
his straining member from the tight embrace of the nylon; her fingers ran
swiftly and delicately along the shaft of his organ as he shuddered with
passion.
Simon and Anita's eyes locked together as she slid the straining member
into her lipsticked mouth and began, slowly, to slide her lips up and down.
The tension built and Simon grabbed her hair and pulled her more forcefully
onto his now engorged cock, she took the whole length into her mouth as he
felt the pressure rise. Releasing her hair, he pressed his breasts tightly
through the bra fabric and then ran his hands over his long hair as the
passion grew. Suddenly, just when the release was imminent, Anita's mouth
released him and she pulled him upright to stand in front of the mirror,
his cock glistening with pre- ejaculate and her lipstick. Turning him so
that he was side-on to the mirror, she knelt down and took him into her
mouth once again, this time she gripped him firmly and he began to buck and
rock as the waves of passion overtook him. At the point of release she
withdrew just in time for the free cock to fire its contents into the air,
hitting her full on the face with force and volume; she smiled and began
licking her lips, opening her mouth to catch the last few spurts.
Simon collapsed onto his knees and Anita quickly stood right up against
him, her moist pussy inches from his face. He hungrily gobbled the prize
in front of him as the dampness increased to a soaking, she moved and
groaned with increasing power until, with a barely muffled scream, Simon's
face was drenched in her juices as she came.
They collapsed together on the floor, entwined in each other's arms and
swiftly fell asleep. Simon woke up, alone, an hour later. He cleaned
himself up, removed his make-up and moisturised his face before reapplying
lipstick and sliding into his favourite long black satin
night-gown. Settling into bed, he turned on the TV and switched to the
adult movie channel. Sure enough, the video footage of his earlier
exploits with Anita were there for all to see; he noticed that she had
cleverly ensured that her face was never toward the hidden camera, even
when she screamed as she came with him licking her vagina.
He awoke suddenly as he felt someone in the room, it was Anita. She turned
on the bedside light, slid into bed alongside him and he started to become
aroused as she caressed his satin-clad body. Soundlessly, she slid on top
of him and began to kiss and caress him; he felt wonderful, this must be
just how a woman feels as her man takes her.
Anita rolled off and gently slid up the hem of the night-gown pulling off
the tight black knickers which restrained Simon's anxious cock. She then
lifted his knees and, sliding a hand under his back, pushed him up so that
he was well off the bed. Taking a pillow, she pushed it under his arched
back and gently forced him back down. The effect was to have his back up
in the air, legs spread wide and, as he lay his arms out to his side, he
knew he looked and felt tremendously vulnerable. She began to massage his
groin and he felt her fingers begin to probe his virgin asshole, she
reached down for something and he felt a cold sensation as she began to
smear a cream over his raised backside, slowly massaging it around his hole
until the lubrication overcame the resistance and he felt first one finger,
then two enter him from the rear. With a light touch of her lubricated
finger on his lips, she walked out of the room into the bathroom.
A few moments later she reappeared, Simon had not moved, laying there
expectantly for the next instalment. He turned his head towards her as she
stepped out of the bathroom. She was completely naked, her large breasts
pushing forward with dark aureoles and erect nipples. His gaze fell to a
huge pink dildo thrusting out from her, held in place by straps around her
waist and thighs.
He watched in nervous fascination as she seductively stroked the pink
rubber, smoothing the jelly-like lubricant over the shaft.
"Now then, my lovely, it's my turn to take you and make you a complete
woman". Anita purred as she moved to the foot of the bed and straddled
Simon as she kneeled on the bed; carefully she manoeuvred the dildo until
Simon felt a pressure on his lubricated ass.
"Relax, sweetheart, and it won't hurt you. We all have to do this the
first time and, believe me it's worth a little pain for the pleasure
afterwards". Simon tried to relax as the increasing pressure suddenly gave
way to a feeling similar to an incredibly intense need to shit . This was
quickly replaced by pain as his asshole was stretched by the dildo
advancing slowly into his lubricated ass.
"Relax, relax", Anita implored, kissing his knees as she pushed slowly but
deliberately. Simon tried to put the pain out of his head and to
concentrate on the belief that he was being taken by a woman, as a woman.
His mind flashed to the fantasies he had dreamed whilst dressed up and he
felt his groin relax at the same time as the artificial member slid its
full length into his virgin opening. Anita was laying fully on top of him
now, kissing his lips as her dark hair cascaded over his face. She began
to move rhythmically, Simon feeling the alternating pressure in his abdomen
as the dildo slid backwards and forwards . She also started to moan gently
and quickly became more agitated as the tempo increased. Simon also
started to move to the rhythm, but Anita stopped him;
"Lie there and think of England. Let me do the work"; She pulled back and
thrust deeply, the sharp stab of pain causing Simon to gasp. Anita became
ever more aroused and suddenly she started to shudder as Simon felt her
juices flow over his groin, she screamed once, very loudly, and collapsed
on top of him soaked with her own sweat. Simon lay there feeling
wonderful, he had been taken like a woman and had satisfied his mate in a
way only a woman can, he realised that the dildo must be two headed and
that, whilst Anita thrust into him, she was experiencing a huge pink rubber
cock rubbing her clitoris and vagina to orgasm. Anita moaned softly and
slid off Simon, she unstrapped the dildo and pulled it from her still moist
vagina. Smiling, she went into the bathroom and re-emerged a few moments
later wearing a pink baby-doll night-dress and clutching another device
with a cock at least twice the size of the one she had just used
Again, soundlessly, she slid alongside Simon's prostrate form and slowly
pushed the huge cock into his already stretched asshole. He grunted in
some pain, but gazed at her marvelling at the care with which she slid the
huge organ into his waiting hole. Taking the straps that hung from the
device, she quickly attached them around Simon's waist and thighs, she then
slid his discarded black knickers over his bulging cock and pulled the
pillow from beneath his waist. Simon looked at her questioningly, but got
a pursed lip sign for his efforts.
She took his hand and bade him stand in front of the mirror, standing up
was difficult as the huge cock in his asshole severely restricted his
ability to move. He eventually managed to stand and Anita took a hairbrush
and sensuously brushed his long tresses. She touched up his lipstick and
smoothed down the night-gown before reaching up behind and, through the
satin folds, she lightly pressed and area on the belt of the device.
Simon's legs buckled as he felt a wave of heat shoot up his body, he gasped
as it was repeated and he felt as if his ass was on fire.
She reached behind him and pressed the switch once more. This time he felt
a warm pleasurable glow emanate and the device started to vibrate slowly at
first, but with increasing intensity. Anita guided his hands down to his
own cock, which was at bursting point, and she encouraged him to masturbate
himself. The increasing frequency of the vibrating cock in his asshole
matched the speed of his hands as they slid along his cock, but as soon as
he felt himself reaching orgasm the device emitted its previous shocking
jolt. Simon was bucking and jolting as alternate waves of pain and
pleasure coursed through him, but he could not reach release. Anita then
stepped over to a bag on the floor and removed what seemed to be a remote
control device. She smiled and pointed it at Simon; instantly he felt the
cock in his ass begin to grow in length and width, it started to pulsate
and he felt a warm sensation as fluid began to drip out from his panty-
clad asshole. Suddenly there was an electric jolt, of a different nature
to before, Simon's own cock erupted and shot massive loads of ejaculate
across the room, liberally splattering the mirror with a white juice.
Anita pressed another button and Simon felt the device in his ass shrink
and stop. He collapsed, exhausted on the bedroom floor.
"There, that was good, you really enjoyed being fucked up the ass by a
machine, I am sure you can be really helpful to our guests". Anita smiled,
and kissed him full on the lips, "When you check out tomorrow, leave all
your feminine clothes in the room. I'll have them cleaned and ready for
next week, I might even go shopping at the weekend and buy you some more
outfits. Remember, we have the videos, your work colleagues and family may
not understand if they receive them, come back next week and they won't".
Anita opened the door and left.
That was how it all got started. Simon has worked at the Bromsgrove office
for 2 years now, resisting his wife's suggestions that they move closer so
that he doesn't have to stay away so often. Aside from family holidays and
work-related trips, which have to be agreed with Anita in advance, Simon is
regularly available at the Stakis hotel on Tuesday and Wednesday nights.
He has built up a regular clientele of visiting business women, never men;
some of his favourites insist on buying him a romantic dinner and just
talking girl to girl with the added bonus of gentle non-penetrative sex and
a cuddle. Other regulars insist Simon wears the strap-on dildo and they
abuse him whilst wearing an array of leather and bondage gear.
The hotel's bookings increased by over 30% in the first 12 months after
Simon's services became available. Anita is now a director of the company,
but still works from the Bromsgrove hotel. The sales of the videos have
netted almost 100,000 pounds and Simon's wardrobe includes some beautiful
designer outfits, tailored to fit by local seamstresses. Everyone seems
happy with the arrangements and Simon's new-found contentment has helped in
his work and home life. He knows his wife suspects him of having an
affair, she has occasionally called him at the hotel in the evening and has
been suspicious when the well-trained staff have said that he is not in his
room when he is providing room service.