The Game Ch. 02

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Transvestite is blackmailed and forced to have sex.
6.5k words
4.76
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11

Part 2 of the 6 part series

Updated 06/09/2023
Created 01/17/2019
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MicheleNylons
MicheleNylons
3,961 Followers

Chapter Two - Petra Returns

21 September 2007

David had showered and dressed while his daughter Rachael lay sleeping and then waited impatiently for the nanny to arrive. He'd drank too much coffee and stole another two elicit cigarettes and was feeling a little high as well as anxious and preoccupied.

Who was the Quizmaster and why were they blackmailing him? Surely it had to be either Rachael, Timothy, Sandra, or Bethany; there were other students who knew about The Game but only the group of six had played it. But why wait twenty years? What did they want?

The nanny arrived promptly at ten; she was one of the many English speaking foreign students who paid to attend university in the UK, she supplemented her income nannying for Marie and David three days a week, making up any missed classes in the evening. David handed over custody of Rachael, snatched up his mobile phone and car keys and drove his Honda Civic to the address he had been directed to in the blackmail letter.

Parking was terrible in the small streets close to the university, without a resident's permit on-street parking was not permitted anyway. This suited David; he didn't want to park too close to his old digs. He didn't know if the Quizmaster was watching him but more importantly he didn't want to have to explain to Marie why he was there if some nosy-Parker told her that David had been seen near his old flat.

He found metered parking in a lot around the corner and used a shortcut through the back alleys to get to his old flat. When he arrived out from of the big Victorian house he was unsure what to do; the letter had instructed him to come to this address to find his dare but didn't provide any further clarification. Then he saw the corner of a lavender envelope protruding from the mailbox slot for flat 12C, his old address. He looked around carefully and saw that the street around him was empty and he carefully extracted the envelope. David had trouble squeezing the envelope though the slot; it was bulky and heavy. Inside was a set of keys.

David opened the door to the bedsit that had been his home throughout his time at university. He entered the diminutive one-room bedsit comprising of a combined kitchen, lounge, and bedroom; fitted with a kitchen sink, gas burner cooktop and tiny refrigerator. A tiny ensuite bathroom had somehow been fabricated when the existing residence had been subdivided into boarding rooms; an even smaller closet-come-wardrobe beside it. It was like stepping into the past; the room was decorated exactly as it had been when David lived there. Or more correctly, when Petra lived there.

There was a small wooden dining table with two chairs set against the window, an overstuffed lounge chair and scarred, cigarette burned, coffee table in front of a TV and a CD player sitting on a small cabinet, a double bed with pink satin duvet and half a dozen throw pillows. An attempt had been made to cover the baby-shit coloured wall with iconic posters: The Bangles, Heart, Cindy Lauper, Madonna, Kate Bush, Michelle Pfeiffer, Molly Ringwald. When Petra was not 'in residence', the posters would be replaced by posters of Huey Lewis and the News, Prince, Tom Cruise, Sly Stallone, Arnold Schwarzennger, the Rolling Stones, and English football heroes. The duvet would be a plain black cotton coverlet; there would be no throw pillows.

For two years David had lived a double-life. To his university fellows, to his friends, to his family, to the outside world he was David: boozer, doper, struggling student, and Game player. Most evenings and on weekends, except when he was gaming, David transformed into Petra: an attractive, leggy, young woman with a penchant to dress immodestly at times.

Petra was also William's secret lover.

The room smelled vaguely of Christian Dior's Poison; Petra's favourite perfume, undercut with cigarette smoke and marijuana.

David made his way over to the closet. It was filled with Petra's clothing: some dresses, but mainly skirts and blouses and a couple of jackets. He squeezed the padded shoulders of a dark blue fitted jacket with gold buttons and smiled wanly. He opened the drawers and found an accumulation of lingerie and hosiery, the second drawer held costume jewellery and accessories, a small collection of high heels was laid out on the shoe rack. There was no male clothing. In the two years that Petra existed alongside David, David had kept his male clothing in the closet; Petra's clothes had been secreted in two hanging clothes bags, the shoes, underwear and accessories locked in a suitcase under the bed.

He was not surprised to see Petra's makeup laid out on the vanity in the bathroom. This too would be secreted away in the suitcase whenever David was in residence.

At first it was difficult living a double life but he soon got into a routine. Most of the time the flat looked exactly like a bachelor flat, everything unkempt, clothes tossed here and there, empty beer bottles, pizza boxes and Indian food containers piled next to the sink. When Petra was in residence the place was immaculate and feminine.

Being a loner, except for his group of game-playing friends, he didn't have to worry about unexpected visitors. On the rare occasions that he hosted his friends or family the place looked very blokey. Most evenings Petra was in residence and the only visitor she had was William. Sweet William.

David closed the bathroom door and sat on the bed and put his head in hands.

Someone had recreated his life from twenty years ago and whoever it was seemed to know everything about his past. He suddenly felt very tired; almost exhausted. He kicked off his loafers and lay down on the bed.

He could smell Petra on the pillows; Poison perfume, her finishing powder, her shampoo. He stared at the cracked and stained ceiling and recalled what had happened when Petra and William had left The Head Office.

September 1985

Petra and William walked home like lovers; never really talking, just happy to be together. At one point William pulled Petra into an alley and kissed her passionately, holding her tight, exploring her mouth with his tongue. She had rubbed against him like a cat, lifting a leg and curling it around him. His hand found her leg and stroked her stockinged thigh.

They broke the kiss and continued home, Petra was so infatuated that she hadn't even thought about what might happen if one of the neighbours saw her. It was unlikely anyway as it was after midnight and in any event no one would have recognised her as David.

"Well this is it. Are you sure?" Petra tuned to face William; her pretty eyes searched his.

William kissed her nose affectionately.

"Lets go up; it's cold," he smiled at her and then squeezed her buttock.

"Cheeky," she smiled back at him.

Petra didn't know what had come over her; she was behaving like a ditzy teenage girl rather than a twenty-year-old man. But David was gone; there was no David, only Petra.

She panicked a little when she realised that her keys were still at Bethany's flat but she knew that a spare key to the front door was hidden under a flowerpot. She opened the door to the terrace house and put a finger to her lips indicating for William to be quiet. He had to help her up the stairs, not so much because of the booze and the dope, but because she was still learning to walk in her high heels.

David often left the door to his flat unlocked; after all what was there to steal? He had done so tonight and Petra opened the door and stepped inside. As soon as William came inside she closed the door, spun the lock and pulled William to her. They kissed all the way to the bed in the dark.

William shucked out of his clothes while Petra turned on the bedside lamp and threw a sheer red scarf over it. It gave the room a rosy intimate glow. She lay down on the bed and watched William take off the last of clothes; his penis was erect again and stood out proudly from his thin frame.

Petra had never been with a man before; how could she? She hadn't existed until tonight. But David knew how his girlfriends behaved and what they did to please him and that knowledge now resided inside Petra.

She held out her arms and William lay on the bed on top of her. She wrapped her arms around him and kissed him, relishing the feel of his hard manhood pressing against her lower belly.

Petra reached between their bodies; she wanted to feel the girth of William's penis; it was hard and sleek in her grasp. She became tumescent herself, her own erection pushed against her skirt through her panties. She gasped when William touched her there, under her skirt.

They kissed and fondled each other languidly; in the safety of the flat there was no rush. Petra manoeuvred herself so that she was astride William; sitting on him as he lay prone. She kissed his lips, worked her way down his neck to his chest, his belly and found his penis with her mouth. She licked his turgid phallus, exploring the flesh with her tongue; the veiny shaft, the bulbous purple glans, she tickled his fraenulum knowing that it would drive him wild with desire, which it did. She took his member into her mouth and slowly sucked on it; relishing the little globules of pre-seminal fluid that she licked away and swallowed.

William moaned and held her face; gently guiding her tongue and her mouth to the sensitive places on his manhood and his scrotum. Petra took his testes in her mouth and suckled them until William lifted her face out of his groin.

"Stop or I'll come," he whispered.

"I want you to come darling," Petra smiled up at him as she stroked his shaft.

William pulled her up beside him and kissed her.

"I want to come inside you," he whispered in her ear.

Petra looked at him lovingly and nodded.

She knew what this would mean and although she had never done anything like it before, the fundamentals of the act that he wanted her to perform were obvious to her. In the dresser drawer was a tube of lubricant that David used sometimes when he bought women home. Petra took the tube of KY jelly and smeared a gobbet of it on William's penis, working the cool viscous lubricant into his fleshy manhood with her fingers. He reached down to stop her.

"Careful of I'll misfire," he smiled.

Petra kissed him and while doing so she reached behind herself, inside her knickers, and placed a globule of the viscous lubricant between her buttocks on her sphincter.

Still kissing William she straddled him, her knees on the bed and her buttocks poised above his groin. William embraced her as his tongue searched her mouth. Petra hiked up her skirt and deftly reached behind herself to pull the gusset of her panties aside, exposing her sphincter.

She positioned William's penis at the entrance to her anus and slowly, ever so slowly, lowered herself on his engorged organ until she was impaled on William's hard cock.

Petra threw back her head and moaned like a harlot as she slowly began to ride him.

She was expecting some pain as she slid William's hard phallus inside her sphincter and pain she got; but she bit her lip and tried to relax. As more of him entered her the pain receded and metamorphosed to a feeling of fullness and then a delightful perception of tingling pleasure radiated from the tight ring of her sphincter. A deep pulsing delectable sensuality disseminated from her prostate and she positioned herself so as to guide William's organ onto the sensitive gland.

William held her by the hips and helped guide her as she slowly started to ride him; lifting herself so that the tip of William's penis was just inside her and then lowering herself and grinding her buttocks as she was fully impaled.

William smiled up her and she smiled down at him.

"Nice?" she asked as she rode him with slow deliberate thrusts.

He smiled up at her and nodded. She fell on him so that they could kiss while they fucked. William adjusted his hips so that she remained fully impaled on his cock as they kissed passionately.

Petra began to drive herself more vigorously up and down as the delightful feelings of rapture increased. She felt so feminine, so womanly, so wanton, and so downright lewd as she fucked her lover. She could feel the fullness of him inside her and it just felt so right, so perfect.

She wriggled her buttocks and bucked against him, driving his penis deep inside her, the deeper he probed the more wonderful it felt. They pawed at each other as they kissed and fucked; William raked her thighs, laddering her stockings with his enthusiasm and then returned his hands to her hips so that he could drive himself upward and deep inside her.

The front of Petra's panties was soaked with pre-ejaculate; she was close to orgasm and sensed that William was too.

She broke the kiss and threw back her head; pushing down on William's chest with her palms and rutted on top of him and then pressed her buttocks down hard into his groin as she ejaculated into her knickers. William squeezed her hips and pushed her down on him as he emptied himself deep in her anus; his cock pulsing as jets of hot semen filled her tight passage.

They both howled with pleasure and Petra fell forward smashing her lips against his as she writhed and wriggled astride him, impaled by his erupting manhood. They clung to each other and rode their orgasms to a precipice and then slowly came down together.

She lay on top of him panting, trying to regulate her breathing. William held her close as his penis slowly drained the last of his issue and deflated inside Petra. When she felt him fall out of her anus, Petra slid her panties back into place, feeling a little of him leak from her as she did.

They lay side by side, not speaking, just kissing and touching until William once again became engorged and this time she lay underneath him, just like a woman, as he made love to her, kissing and caressing her throughout. They climaxed together again and then fell asleep in each other's arms.

When Petra awoke the next morning William was gone and she had to deal with the awful practicalities of the previous night. Her knickers were soaked with semen and other bodily fluids that made her look away and wrinkle her nose; she would soon come to realise the importance of douching. Her stockings were laddered beyond repair and the clothes she had borrowed from Bethany were rumpled, stained and smelled of sex.

She was hungover and morose; she couldn't believe that she had given herself over to such wonton lasciviousness simply because she was dressed as girl. And with her best friend; who she no idea how she could ever face again.

She put all of the blame, guilt and regret on herself, laying no blame on William, as she stripped off her clothes, washed off her makeup and showered away all evidence of ever being Petra. But when David looked at himself in the mirror he could see the bite marks on his neck, the scratches on his hips and shoulders, and the imprints of Williams fingers on his thighs and buttocks.

He washed out the knickers in the sink and hung them to dry alongside the bra and suspender belt and then dressed in jeans and a shirt and stook the blouse and skirt to the dry cleaner on the corner, paying in advance for a same day service.

Later that afternoon he went around to Bethany's hoping that she would be out and he could just leave the clothing on her door but she was home and insisted on hearing how the evening had panned out.

"More of the same really; guys kept coming onto me and I kept repelling them. It got boring and repetitive," David lied.

"Well I have to say you looked absolutely gorgeous as Petra; so feminie and downright sexy. I'm a little jealous," Bethany kidded him.

"Anyway thinks for bringing back my clothes and stuff, you didn't have to do so straight away. Can I offer you a bevy?" Bethany made her way over to the sideboard where a few cans of lager a cask of wine sat.

David felt his gore rise at the prospect of drinking.

"No thanks Rache; I'll just take my clothes and keys and fuck off," David got up out of the armchair.

"Well at least let me fix that for you," Bethany looked down at David's hands.

He was so preoccupied and hungover that he didn't realise that he was still wearing nailpolish. Bethany sat him back down and went to work with nailpolish remover while David tried not to gag on the acetone fumes.

21 September 2007

David's phone beeped bringing him out of reverie. It was a text from Marie reminding him that she wouldn't be home for dinner and that he would need to feed their baby Rachael prior to putting her down for the night. David texted a response and put his flip-phone down on the nightstand and was about to get up off the bed when he saw the envelope tucked under the pillow beside him.

He tore it open and read the typed black text on the lavender paper.

'Petra,

I much prefer the conventions of our time at university, conversing by letter, but modern technology is wonderful and essential to your first dare.

However might I suggest you practice your makeup skills, you are undoubtedly rusty after such a long absence. Maybe slip into some of Petra's clothes and practice that sexy Bonnie Tyler voice and walk around in high heels until you are comfortable in them again.

Anyway to business... In the corner are a few contrivances that our out of place in this memorial to your past life. One is the Toshiba laptop next to the TV and beside it a mobile phone. The computer is unlocked as is the phone. You will need them for this and future challenges.

Your dare begins at seven PM and finishes at midnight tonight as per the rules of The Game. I hope that is not too inconvenient for you Petra but I really don't care if it is; you know the consequences if you don't play or don't see the dare through to completion. Your first challenge is simple and is designed to make you comfortable being back in your own persona and you have plenty of time to prepare.

I have arranged a date for you, an assignation really, on a dating site. You are to let the man into your apartment at 7PM and entertain him until midnight; you know what I mean by entertain right?

Failure to complete the dare means I win The Game and the kitty and as a consequence all of your friends, family and business associates will get to meet Petra and be entertained no doubt by the details of her sordid past.

Don't be too shocked Petra; admit that you are a little intrigued and excited to be resurrected and put back to good use doing what you do best. You fucking whore!

The Quizmaster'

"What the Fuck!" David shouted to the empty room.

There was no way that he could undertake this dare. Who would look after the baby? What would he tell Marie? And who makes dates with strangers on hook-up sites?

David got up off the bed leaving the letter on the pink duvet and went over to TV stand where an eighties-vintage color TV sat and incongruently beside it a Toshiba laptop with a telephone jack inserted in the modem port at the rear. The telephone cable was long enough to reach the coffee table and David set it down there and sat in the lounge chair. He leaned forward and pressed the Windows login icon for 'Petra Pantsdown'; the Quizmaster had a sense of humour.

As David was advised no password was required and the welcome screen opened to reveal that the dialup internet connection was functioning and the web browser was operating with a number of windows open. The first was a hotmail email inbox for Ms Petra Pantsdown, the second the profile page on the Adult Friend Finder dating site for a Ms Petra Pantsdown. Her profile was adequately populated with pictures of her, mostly demure but a few compromising pictures of her and William but William's face had been obscured. To summarise the profile it was basically was a plea from a promiscuous transvestite looking for casual encounters with men.

MicheleNylons
MicheleNylons
3,961 Followers
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