Jack to Jacqui


Redundancy and divorce are two of the most catastrophic things that can occur to anyone. It is not entirely unusual for one to follow the other, but the hurt and feeling of devastating rejection are doubled when it happens.

Jack Larbury went through just that. After 20 years, his job was gone as the company he'd joined as a 16-year old went through a process of "down-sizing". Within three months, as he made strenuous efforts to (a) find himself another job and (b) make the necessary economies at home to eek out his redundancy pay-off, his wife Carole upped and left him, after admitting to an affair with her boss.

Carole had always loved living well, and was clearly uncomfortable to say the least with any suggestion that she should curtail her lifestyle. PA to a recently widowed company director, she had always got on well with her boss and, indeed, had openly bragged to anyone who cared to listen (including her husband) that she knew him even better than his wife. Now that wife was dead, after a sudden illness, and her boss was devastated.

Jack had been understanding when Carole said that she was going to work from his house rather than the office in the immediate aftermath of his bereavement. The house in question was a five-story detached property, set in its own grounds, on the outskirts of the city and Carole later admitted that she had felt immediately at home there, from the minute she walked through the door.

She also admitted that on only her second visit to the house, she had found her boss still in bed and apparently still upset. Her attempts to console him had ended with them "fucking like rabbits", as she told Jack, and they had made love at least once on every visit since.

She walked out on Jack one Monday morning, saying that she would not be back and that someone would call to collect her things. No-one did, and Jack later learnt that Carole quickly decided that her new home would require a new wardrobe and that she wanted no reminders of her old life with him.

They had never had children, despite trying in the first years of their marriage. Tests showed Jack to have a low sperm-count and that, plus his smaller than average penis - no more 5 inches when fully erect, at most - had turned Carole off sex with him anyway. She consented to intercourse with him once every six weeks or so, but always insisted that he finish her of with his hand, as he never satisfied her when they fucked. For his part, Jack resorted to reading porn and watching certain late-night cable TV channels and wanked himself off to secure physical relief. Occasionally he phoned a live 1-2-1 sex service, but when Carole saw the number come up on the phone bill, she would always ridicule him, there was often a row and their next intercourse session was postponed still further.

So now Jack was alone. Quite alone. Only occasional part-time work, an empty house (thankfully mortgage paid) and a wardrobe full of Carole's things.

About three weeks after she'd left, Jack woke feeling very, very horny. He'd allowed himself a rare night out the evening before, just having one drink with an old mate at a pub down the road.

He was only in the pub for an hour at most, but the young women in their skimpy tops, tight jeans and spike-heeled shoes, developed a lust in him that had stayed in his head all night while he tried to sleep.

He was semi-erect when he woke and he looked down, under the sheets at his tiny cock. Even in its nearly hard state, he could only just see the tip of it protruding from his pubic hair.

He went to the bathroom and picked up a pair of nail scissors from a cabinet drawer. Slowly, carefully, he snipped round the bushy, wiry hair until it was almost trimmed away altogether. His erection did not diminish while this was going on; if anything, it got harder with the slight excitement of what Jack was doing.

His cock was now exposed in a way that it never had been before. A pile of tiny black hairs lay on the bathroom mat and Jack brushed all but a small residue into the waste bin.

Stepping back and admiring his work, he made a major decision. He turned on the tap and filled the washbasin with hot water. He opened the cabinet and found the lady shaving gel that Carole used to use when shaving her legs and armpits.

Jack applied it to what was left of his pubic hair and using Carole's old lady razor turned what had been the seat of his bush into totally smooth skin. He didn't stop there, continuing the process for each leg.

He found dealing with the top of the rear of his thighs awkward and he knew that he hadn't been completely successful, so another plan developed in his mind. Before putting that into action, however, he shaved his armpits and was about to do the same to his arms, but stopped when he decided that plan B would deal with that.

He gave himself a regular face shave and went back to his bedroom. Opening Carole's drawer he found, as he knew he would, a selection of panties. He picked out a black pair, silk trimmed with lace, with a thigh-high style. Pulling them on he registered consciously that he had lost a lot of weight in the last few months.

The worry of all that had happened had affected his appetite markedly and he was down to around nine and a half stone. At 5'10", he had never weighed much more than eleven stone, but the weight had dropped off him just lately.

It also occurred to him that, as a result, he was now pretty close to Carole's size and build and his mind was now racing. Contenting himself just with her panties for now, Jack dressed in his own clothes - shirt, a pair of jeans, socks and loafers and almost ran downstairs to his study where he reached for the Yellow Pages.

He quickly found what he was looking for and dialled the number. It was answered promptly and, within a few minutes the arrangements were made. The lady on the phone had been more than helpful and sounded very understanding and sympathetic, as though she dealt with such requests every day. "Maybe she does," thought Jack, and he felt his erection grow again against his now hairless body.

The drive took no more than twenty minutes. He parked at the rear of the premises for privacy, as the lady had suggested and he almost ran to the rear fire escape type staircase she had told him to use.

He pushed on the doorbell and waited no more than a few seconds before being greeted with a gentle smile and genuinely warm welcome by the lady who introduced herself as Shirley. She showed him through the back of the salon, away from other customers and into a small white consulting room. There was a small desk with a chair on one wall while a work surface, including a washbasin, hot water system and a row of white plastic bottles ran the length of another. In the middle of the room was a table, covered with two white towels.

"Get undressed, my love, and make yourself comfortable on the table," cooed Shirley. "I'll be right back."

She closed the door and left him to it. He did as she instructed and he had hardly sat on the table, when Shirley returned, locking the door to the consulting room behind her.

They talked and Jack explained what he wanted, repeating what he had told her on the phone.

She cautioned him that doing all that he wanted in one go was unusual, simply because it could be fairly painful, but he insisted. They agreed that they would go on for as long as he could take it.

Two hours later, Jack emerged, hot and stinging in places, but with a totally smooth, shiny, waxed body and an appointment to return to Shirley in a couple of weeks. His face was also immaculately made-up, with a soft shade of green eye shadow and satin pink lips, a bonus treatment that Shirley only provided for special customers.

Back home, he made himself a cup of coffee and sipped it carefully, not wanting to smudge the lipstick.

He picked out just what he wanted from Carole's wardrobe and swapped his own clothes for hers. His choice was a cream skinny rib top and navy mini skirt, and a pair of black patent high-heels. The shoes were half-a-size out and pinched at the toes; he resolved that he would have to buy his own.

Looking in the mirror, he combed his hair forward and sprayed it to hold it in place. He looked at the full effect and caught his breath. He looked well, fantastic - if he did say so himself. There were just two areas of concern. No tits, and the skinny rib needed tits for full effect and his cock, tiny though it was, made an outline in the skirt.

Hitching the skirt up, he tried something he had read about only recently in a porn magi, where a transvestite comedian had explained the intricacies of dressing as a woman. Reaching inside the panties he pushed his balls back into himself and pushed his penis so it lay back against where his ball sac had been. It was a quite painless process, but it took him three goes to get it right. When he did, he pulled the panties tight against him and brushed the skirt down.

Checking in the mirror again, he knew he looked good. The tits were something he would have to sort out, but he could get away with it for now, by wearing a jacket.

Twenty-five minutes later, "Jacqui", as he decided he must now call himself in such instances, was driving into the countryside with one destination in mind - a lay-by where he knew that men went to meet with men. What he was going to do when he got there, he had no idea, but his heart was beating faster and faster as he got closer to it.

There were five other cars and a lorry parked there when he arrived. All the cars were empty, with the occasional movement in the adjacent woods the clue as to where their occupants were.

Jacqui sat and waited, though he didn't really know what for. No one returned to their car, no other car arrived.

"What the hell," he said to himself and, checking his face in his rear-view mirror, he got out of the car.

The path alongside the lay-by was narrow but he walked on it, feeling perfectly at home in the skirt and heels. He walked along the line of cars and past the lorry. He saw no one and turned to walk back. As he did, he looked up into the cab of the lorry and saw the driver peering at him over the top of a newspaper.

As he walked back alongside the lorry he heard its door open.

"Jump up," said the driver. "Here, let me help you."

A big, hairy hand reached out and without thinking, Jacqui grabbed it and was hauled into the cab.

The driver was middle-aged, unshaven, but ruggedly good-looking. He appeared to be quite fit and obviously muscular, happy to wear just a razorback vest to show off his pecs and biceps.

"And what's your name then sweetheart?" he asked, stroking his hand on Jacqui's thigh as he spoke.

"Jacqui. What's yours?"

"My friends call me Hub."

By now Hub's hand was under Jacqui's skirt and making its way rapidly to her knickers. Jacqui's heart pounded.

Hub stopped when he felt the base of Jacqui's tiny cock tucked underneath her.

"Ah," he said with a smile. "What have I found here? Is this for me?"

"I - I guess," Jacqui replied nervously.

"Let's go in the back," said Hub and he pulled back the curtain behind the seats and ushered Jacqui into a an area where a sleeping bag was laid out and the walls decorated with pictures of page three girls and a couple of boy bands.

Hub unzipped his jeans and dropped them to his ankles in one movement as he lay down on the sleeping bag. He pulled Jacqui down alongside him and held her firmly in his arms. He looked in her eyes and kissed her strongly on the mouth.

Jacqui tried to respond as she thought was right and their tongues met.

Hub's hand reached for Jacqui's knickers and pulled them down. He sat up, shuffled down so that his face was alongside Jacqui's now erect cock and took it in his mouth. As he sucked it, Jacqui closed her eyes and for just a second thought "what the hell am I doing?", but the thought was shelved when she felt herself being turned on her side, her ass facing Hub.

His left arm reached for her shoulder, while his right hand guided what felt like a massive rock against Jacqui's ass. Sensing it would need help, Hub reached out for a jar in the corner of his unit. Daubing two fingers with the jar's contents he pushed them into Jacqui's ass, slowly at first, then further and further in.

Jacqui squealed and moaned - but not with pain. It felt like nothing he had ever experienced before - but then he hadn't experienced it before.

Hub's massive cock soon replaced his fingers and felt even better, specially when he reached his arm round Jacqui's waist and started to wank her baby cock.

Hub fucked and fondled Jacqui firmly but gently, squeezing the base of her lady-cock whenever he thought she might not be able to hold on. Then, when he knew he was going to cum himself, he fucked harder and faster, moving in, out, in, out, in, out of Jacqui's ass, and wanking her faster too.

As the cum shot out of her little prick, Jacqui felt Hub's hot creamy cum pumping up inside her. He went on and on, cumming till she thought he was going to fill her whole body with his spunk.

After they uncoupled, they lay together for a while, Hub confessing to a fantasy that he had his own lady-boy to visit. They swapped mobile numbers and promised that they would meet again.

Back home, Jack showered and cleaned out his ass and removed Jacqui's face with cold cream that Carole had left behind. He knew his life would never be the same again and that some big decisions lay ahead.

For now though, he was content to put Jacqui back in the wardrobe, until..., well, maybe that night...

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