Just Do What The Nice Man Says Honey

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Julie Cashmore followed her gentleman caller downstairs and escorted him to the front door. She opened the door and looked both ways up and down Clifton Road and seeing that the street was deserted she nodded to her gentleman caller who bustled past her most ungraciously and quickly strode away. He did not want to be seen leaving 32 Clifton Road; none of her gentlemen callers did.

She saw the curtain twitch in the window in the house across the street. Nosey Mrs Tanner was watching of course. Julie stuck out her tongue and gave her the forked fingers and the curtains slammed shut.

Julie closed the door and climbed the stairs to her bedroom. It stunk of cheap perfume, cigarettes and sex. Her ‘gentleman caller’ had left the money on the nightstand and Julie counted out the wrinkled notes. The man had left the exact amount; no tip. Arsehole!

Julie stood in her stocking feet and nylon full-slip and drank the dregs of her scotch and coke. She scratched her bottom and pulled her knickers out of her buttocks where they had ridden up. The gusset was soaked with clotting semen and vaginal juices. She took the tin cashbox from the second drawer of her dresser where she kept it under her knickers and lingerie. She unlocked it and added the money she had just earned to the small bundle of notes and counted them.

“Fuck!” she sighed.

There was just enough to pay this month’s rent and to buy groceries. Julie was living just above the poverty line.

It didn’t help that the eighteen-year-old in the adjacent bedroom ate like a wolf and spent his days fruitlessly looking for work (or so he said anyway) and his evenings locked in his room getting up to who knew what. She had implored Alex to take any job he was offered but so far her pleas had fallen on deaf ears. She didn’t know what was wrong with the boy. He didn’t seem to have any friends and he spent all of his spare time sequestered in his room.

What was more than a little disturbing was that Julie had noticed that someone had been ‘borrowing’ her underwear and hosiery and she also suspected that the same ‘someone’ was accessing her wardrobe. At first she thought she was imagining it. She would empty the washing basket out on the sorting table before she started her twice-weekly wash and she’d swear that a pair of her knickers were missing, sometimes a pair of tights and maybe a slip or negligee. There was only one ‘someone’ who that could have been, wasn’t there?

Julie sometimes came home from work and went to her wardrobe to dress for her ‘evening employment’ and was sure that her clothing had been rearranged and her shoes had been tampered with. At first she thought it was just her imagination but then she noticed that some of her makeup had gone missing too.

Then, about a month ago the snowdropping had suddenly stopped. Her laundry was no longer being tampered with, her wardrobe was as she left it and all of her makeup was accounted for. She had breathed a sigh of relief.

Her day job was managing the self-service Laundromat two streets over from the council house where she lived. The wages were shit and she had to throw the owner a free fuck once a week but it was the only job she could get. Julie had left school before attaining her GCE to marry a man with whom she was besotted. He’d joined the army and for a while Julie enjoyed the benefits that came with being married to a serviceman. That was until he absconded from the army and left Julie with a young son and disappeared without as much as a goodbye. She had no employment prospects and nowhere to live.

Julie had done what she had to do to survive. She’d cadged a council flat and sought employment as a seamstress which paid well until the company went broke and then she took work where she could get it. Being an attractive woman who liked to dress to show off her best attributes being her large breasts, tidy bottom and long legs she had managed to find poorly paid positions in offices and factories performing office work but she was preyed upon; mainly by older married men who promised her much and invariably delivered very little.

It wasn’t long before Julie realised that she was giving away what she could charge for so she started tomming. She’d earned a decent wage selling her body until the ravages of the work and her age took their toll. The better class of clientele who were willing to shell out a pretty penny for her company dwindled away. The champagne dinners, classy hotels and high-rolling businessmen eventually gave way to take-away dinners in cheap motels with travelling salesmen and then the downward spiral continued until she was eating fish and chips on the streets and performing knee-tremblers in back alleys or lying on the backseat of a car with her knickers in her hand and her legs in the air.

The constabulary were under pressure to clean up the streets of Balsall Heath, Birmingham, which was probably just as well because Julie was too old to be streetwalking so eventually she found herself in the predicament she was in now: prostituting herself from home for men who were too stingy to pay for motel rooms but were prepared to pay less for, shall we say, more mature ladies like herself.

Mrs Tanner had reported Julie to the rent board stating that she believed that the tenant of number 32 Clifton Road was living off immoral earnings and they had sent around a skinny balding gentleman in his fifties to investigate. Julie answered the door in full makeup, silky black fully fashioned stockings, high heels and her shortest miniskirt and the gentleman had left the house thirty minutes later with lipstick on his penis and reported to his superiors that Julie Cashmore appeared to be a hardworking mother who was just scraping by but did not appear to be involved in any unsavoury shenanigans. Of course the skinny balding gentleman from the rent board would drop by now and then just to confirm that it remained the case, always leaving with Julie’s lipstick or her cunny juices on his cock.

In dire straits financially, supporting herself and her lazy son, Julie was at wits end. Then one evening she noticed something that set her mind to thinking there may be a way to change her circumstances for the better.

It was just after dinner and she was sitting in a lounge chair watching the news dressed only in a house coat and her underwear and Alex was lying on the sofa reading an old magazine when she noticed something. Was he wearing tights under his baggy stonewash denim jeans? Yes he was!

There was no mistaking the shimmery nylons encasing his ankles above his white ankle socks.

Alex was using the magazine as a ruse so he could look over it at his mother’s long legs, still clad in the cheap tan nylon tights she wore to work and the white granny-knickers she wore over them. He was sporting a stiffy which was rubbing quite pleasantly against the soft silky tights he was wearing under jeans.

Julie was tempted to confront her son then and there but she really didn’t know how to start the conversation. This seemed to confirm what she had suspected. Her son had been borrowing her undergarments and hosiery and possibly trying on her clothes.

“Go to your room Alex I have a gentleman calling,” Julie lifted herself wearily out of her seat and headed upstairs to change into her ‘entertaining’ clothes.

Alex knew all about his mother prostituting herself and frankly didn’t care. She let him lodge with her without paying rent and he kept himself to himself. Alex had his own secrets and was more than happy with the arrangement. He didn’t get out of bed until after nine in the morning and spent most of the day lounging. He would scoff whatever offering his mother put in front of him for dinner and retire to his room before the ‘gentlemen callers’ arrived. Alex sometimes listened to the sounds coming from his mother’s bedroom and at those times he’d take out one his mother’s nylons and slip it over his cock.

The next day at the Laundromat Julie contemplated what she had the night before. Alex was definitely wearing tights under his jeans, of this she was sure. She left work at midday and went home knowing that Alex had an interview to sign on for his unemployment benefits. He’d tell them the usual story that he couldn’t find anything suitable although Julie knew that he’d turned down a few jobs that Alex thought were beneath him.

She went upstairs to Alex’s room which he considered his sanctuary and kept locked at all times when he wasn’t at home. But Alex had used a cheap hasp and staple and a padlock and it took Julie two minutes with a Philip's-head screwdriver to remove the lock.

Her son’s room surprisingly didn’t have the funk and junk usually associated with teenage boys, in fact it smelled quite fresh with a hint of cheap perfume and everything was neat and tidy. She hadn't been in Alex’s room for years; he cleaned it himself and insisted on privacy. Julie expected that the walls would be covered with pinups from Razzle, Club, Escort and other soft porn magazines and there was indeed a few, the women all dressed in sexy lingerie and stockings. There were also posters of women dressed in fetish fashion such as business suits, nurses and that old favourite… French maids.

Anyone entering the room could well imagine that an eighteen-year-old boy lived in it but would be surprised with the fastidiousness of the place; Julie certainly was.

A perfunctory look around didn’t produce anything incriminating but as Julie explored deeper, what she found surprised her. One side of Alex’s wardrobe held a small collection of women’s clothing hidden behind his own. It was mismatched op-shop stuff; a little shabby and all in a size that she guessed would fit Alex.

In two unmarked shoeboxes were two pairs of lightly scuffed high heels, one white pair and one black pair, also likely purchased at Oxfam. Holding the soles of the high heels against a pair of Alex’s trainers revealed them to be the same size. One of the drawers was filled with lingerie: knickers, bras, slips and negligees and of course there was an assortment of stockings and tights. A small valise at the back of the wardrobe was filled with cheap makeup.

Julie wasn’t stupid. This explained why her lingerie had been ‘borrowed’, her own clothing tampered with and some of her makeup stolen. It also explained why this was no longer the case and also why her son was wearing flesh-coloured tights under his jeans. He was crossdressing and had acquired his own collection of ladies attire and accessories.

What was she to make of this? Was it a fad? Was he a homo? Did he want to be a woman? Many celebrities that were popular with young people these days were presenting as androgynous such as Boy George, David Bowie, Prince, the list went on and don’t even mention Lily Savage and Edna Everage who they both watched on the telly. Some men’s fashion bordered on being feminine and male celebrities were wearing makeup and there was little difference between men’s and women’s hairstyles. This was the nineteen eighties after all.

But a discovery deep in the back of the wardrobe revealed that this was nothing to do with Alex trying to look fashionable. In another shoebox right at the back of the top shelf she found the second-hand Polaroid camera she given Alex for Christmas and a cluster of Polaroid photographs held together with a rubber band. She took it down and laid the photographs out on Alex’s desk.

Julie couldn’t help but burst out laughing. The photographs were of Alex dressed in his female clothing, wearing makeup with his shoulder-length hair teased out.

He looked ludicrous.

The makeup was all wrong and clown-like. The clothing fitted him but he wasn’t wearing it right and the seductive poses he affected were far from it. He looked like a comedy drag queen. She took four of the photographs and put them in her apron pocket.


There was no doubt the boy had potential. With his slim figure, statuesque form, long legs and handsome face, in some of the pictures he did look quite feminine. Alex was a rough diamond that could be fashioned into a beautiful jewel. He was an ugly duckling that could manifest as a swan. All Alex needed was some help.

The germ of an idea began to grow in Julie’s brain. It was audacious, it was cunning and it was more than a little evil but her son had sponged off her ever since he had left school prematurely and failed to find meaningful employment and he hadn't given her a penny of his dole money. She smiled evilly to herself as she put everything back how she had found it and screwed the hasp back onto the doorframe.

Julie was waiting for Alex when he came home from the dole office.

“You're home early,” he quipped as he brushed past her heading for the stairs.

“Did they find you a job?” Julie called after him.

“Of course not mom. Thatcher has buggered this country,” Alex retorted as he started to climb the staircase.

“Don’t suppose you have any rent or food money for me?” Julie leaned on the newel post and called up the stairs.

She heard his bedroom door close and the bolt on the inside being shot. That was his answer.

“Fuck this,” Julie followed him upstairs.

She tapped softly on the door.

“Alex?” she called out.

“Go away mom. Make my tea and get ready for your gentlemen callers,” Alex called out.

She heard the contempt in his voice and it angered her.

“I know about your crossdressing you little fairy!” she yelled through the door.

This was greeted by silence.

Then she heard the rattle of wardrobe doors being flung wide and drawers being yanked open.

“Don’t worry I didn’t take any of it. It’s all there. Of course I kept a few pictures as souvenirs,” she couldn’t help but feel a little self-satisfied.

There was more silence then the bolt slid across and the door opened a crack.

She entered the room and found Alex sitting at his desk looking forlorn.

“How long have you known?” he whispered.

“I knew something was up when you started rummaging in my wardrobe and nicking my nylons and knickers. Then some of my makeup disappeared. Then you stopped and I thought it was just a fad. Your uncle Albert still wanks into my knickers in the bathroom when he comes around to visit. Men do funny things,” Julie said by way of an explanation.

“Then I found your clothes and the pictures and put two and two together. You're a crossdresser or what my generation call a transvestite,” Julie made her way over to her son.

Alex leapt from his chair and confronted his mother.

“Where are the pictures!” his face was inches from hers.

“No need to get angry Alex. They're somewhere safe where no one will ever find them. Let’s just call them insurance shall we?” Julie stared him down and Alex slid back into his chair.

“I tried stopping but I can’t. First it was just knickers and tights, then maybe a slip or a petticoat. I stopped for a while but the compulsion got stronger. I went to Oxfam and got some clothes and shoes… well you’ve seen them. I liked to dress up and just sit around but soon that wasn’t enough so I bought some makeup,” Alex let out a huge sigh.

“Well you’ve seen the results. I look ridiculous but I can’t stop. I’m addicted,” Alex sighed again.

“Is it sexual?” Julie asked plainly.

Alex looked up at his mother’s world-weary but still attractive face and thought he saw compassion and understanding.

“Some of it is. I usually get a… a stiffy and I have to… well you know what men do,” Alex gave her a guilty smile.

“Yes I do. Sometimes into my best sheers,” she reproached him.

“Not anymore! I have my own stockings!” Alex barked back and then realised how ridiculous he sounded and he blushed.

“But it’s not just sex. I feel like a different person when I’m dressed. I really do feel like a girl,” Alex admitted.

“Who else knows? Have you been… you know… have you been with anyone?” Julie asked delicately.

“Fuck no mom! What? Do you think I’m some kind of perv or a nonce?” Alex sounded genuinely distressed.

This is what Julie thought and it was perfect. She was going to make the little skiver pay his way.

“All right, all right Alex. I get it. I don’t have a problem with it so long as it stays here in the house. At least for now. At least until we find out if it’s just a phase that you're going through or if you genuinely want to become a woman,” Julie sidled up to her son and stroked his hair.

“I’ve thought about it. I’ve really thought about what it would be like to live like a woman,” Alex whispered.

“Maybe I can help you. It would be our little secret,” Julie continued to stroke her son’s hair.

“Hardly a little secret is it mom?” Alex smiled up at her wanly.

Julie smiled back.

“Would you really help me?” Alex seemed to have brightened up considerably.

“Yes. I’ll show you how to dress properly and how to apply your makeup. I can give you advice on how to present feminine. You can transform here in the house and practice until you are confident enough to go out and present your new self to the world,” Julie hugged her son and he hugged her in return.

“I’ll go down and make dinner and then we’ll come back up here and have our first training session. I don’t have any gentleman callers this evening,” Julie said regretfully.

She really needed the money.

After dinner Julie and Alex retired to his bedroom.

“Ok Alex, I want you to go into the bathroom, shower and wash and dry your hair and then shave your face and then your body,” Julie said.

Alex didn’t really have any body hair except for his pubis. Even his facial skin was smooth; he only shaved once a week to remove a random hair from his chin but he didn’t argue.

When he returned Alex found that his mother had arranged his makeup on his dresser and laid out articles of female clothing on his bed. He was getting excited.

“Ok sweetie, we really need to work on your makeup skills but first I’m going to work on your hair. Put this on and sit down,” Alex’s transformation was about to begin.

Julie had brought one of her satin robes which she held out to Alex who was naked except for a towel. Alex took the robe and put it on, marvelling at the luxurious feel of the sensuous satin on his freshly shaved flesh. His mother had turned her back on him while he did so.

Alex sat down in front of the mirror. Seeing the hair brush, the cosmetics, the makeup sponges and brushes and the perfume excited him. His mother had brought in her own perfume: Dior Poison, her favourite and his. She had also brought in her own hairstyling accoutrements. She’d also brought in her hairdryer.

Julie moved in behind him and he could smell his mother’s perfume. It was exotic. She ran her fingers through his hair and Alex remembered how she done this when he was younger and she would fix his hair before sending him off to school. He’d always had long hair and it was often unruly. Julie blow-dried Alex’s hair working the dryer to tease his hair out. Then she snipped at it with her sharp scissors to give it the desired shape and then she went to work styling it.

Julie picked up a comb and took small section of Alex’s hair from his crown and sprayed it with VO5 hairspray to give it grip and texture, then she combed the hair from the mid-lengths down towards the roots pushing firmly as she did so. She divided Alex’s hair into sections and repeated the process backcombing and teasing until his hair was sleek and frizz-free.

Alex could not believe the metamorphosis that he was witnessing. His lank blonde hair had been styled into a feathered bob with the fringe just above his eyes with the nap resting on his shoulders. Alex was already thinking of himself in the feminine now that the transformation had commenced. Julie brushed away the cut hair and went straight to work with the makeup. The process took a little while because Julie explained everything that she was doing so that Alex could practice on himself later.

When she had finished Alex looked totally feminine, beautiful and sexy with striking features framed by the blonde teased out bob. Even Julie was amazed. Alex was speechless.

Alex stood and studied his reflexion in the mirror and saw a gorgeous young woman dressed in a red satin robe staring back at him.

Julie lay out a few of the pictures that Alex had taken of himself in drag and began to explain the errors he had made.

“Ok, the hair and makeup are atrocious but we’ve fixed that. Now let’s look at the clothes. You don’t have much of a collection here Alex and you’re wearing them all wrong,” Julie explained.

“Your tights in this picture are the wrong colour for the shoes and skirt and they are wrinkled around the knees. That skirt does not go with that blouse. Your attempts at presenting with breasts are awful. They're too big and they are too low on your chest. Those heels don’t go with the outfit,” she continued, pointing out the errors in the photographs.

Alex began to become agitated with his mother’s criticism and Julie could see it.

“I’m not paying out on you Alex I’m showing you the errors of your ways. I’m going to put you in a simple skirt and blouse ensemble and show you how to do it right,” Julie explained and Alex was once again excited.

Alex couldn’t believe that his mother was doing this. He had always thought that his mother was resentful of him and thought of him as a lazy dole-bludger. Now here she was helping Alex to become the girl that he had always thought was locked away inside him.

“Come over to the bed Alex,” Julie said.

“I’ve laid out what I want you to wear and I’ll go through how to wear it step by step,” Julie explained.

Laid out on the bed was a navy blue A-line miniskirt, a mauve satin blouse, a pair of flesh-toned, sheer-to-the-waist, glossy tights, a pair of black satin full-cut knickers and a matching brassiere and finally a pair of black high heels.

“I bought that skirt and blouse for you at Debenhams so make sure you look after them,” Julie said reproachfully and Alex was both grateful and astounded that his mother had bought them for him.

“Ok, first the practicalities. You have a penis, a scrotum and no tits. In a lot of these pictures the bulge in your crotch is quite noticeable. I’ve already told you what’s wrong with your tits. We need to get the fundamentals right first. Drop the robe Alex,” Julie ordered and Alex blanched.

The thought of standing naked in front of his mother suddenly broke the daydream that Alex was a girl.

“Don’t be shy. You're eighteen years old and you haven’t got anything that I haven’t seen before; I’m your mother for heaven’s sake!” Julie unknotted the sash on Alex’s satin robe and eased it off his shoulders.

Alex looked like a young girl yet to sprout her breasts. His skin was like alabaster and flawless, his body smooth with slim hips, a flat belly and trim waist. Perfect except for the long appendage and scrotum dangling between his legs.

“We will need to tuck this,” Alex blanched when his mother gently tapped his cock with her fingertips.

“Ok sit on the bed and let’s put your tights on first so we can tuck this away,” Julie tapped her son’s cock a second time.

It had been quite some time since Julie had seen her son naked and he had certainly developed in the genital area. His equipment was quite impressive.

Alex sat on the bed and Julie took the flesh-toned, sheer-to-the-waist, glossy tights and carefully rolled up one leg.

“Watch how I do this so you can do it yourself. It’s important to put them on properly so there are no wrinkles,” Julie said as she slipped the reinforced toe of the stocking onto his foot.

She slid the toe of the other stocking onto his other foot.

“Put your legs out straight,” Julie said and when he did she began to roll the nylons up his legs, smoothing out the silky fabric as she did so.

When she had the tights around his knees she got Alex to stand and eased the pantyhose up his thighs until she had the panty part of the hose around his hips.

Alex was overcome with a delicious feeling of delight as his mother smoothed the gossamer hose along his flesh. Her fingers felt like butterflies fluttering in his skin and he had to think unpleasant thoughts to prevent an erection but his cock twitched a little and had become semi-erect.

“Now pull them up tight so that the waistband is high up on your waist,” Julie said.

Alex did as he was told and the diaphanous fabric pressing on his scrotum felt delightful, his cock lay flat along his belly shrouded in the sheer fabric. It was still flaccid but he could sense a burgeoning erection and he felt very embarrassed.

“Now, push your testes up into your inguinal canals. That’s the little cavities in your crotch where your balls go when you are cold and from where they descended when you were younger,” Alex’s mother explained.

She alarmed him by taking his hand and putting it between his legs so that he could feel the spot she was telling him about. It was little uncomfortable at first but Alex managed to push his testes inside his body.

“Now you do this,” Alex became very concerned when his mother reached into his tights and wrapped his penis in his empty scrotum and pushed the package between his legs and then pulled the gusset of his tights up until the waistband was snug around his waist.

“There. That’s perfect. Go look in the mirror,” Alex’s mother patted his groin and then turned him to face the mirror.

Alex was amazed. He once again felt like a girl, looking at the perfect Vee of his pubis under the shimmery tights.

“That’s amazing mom; how do you know how to do this?” Alex asked.

When Julie had worked the streets she had worked alongside a couple of transsexual prostitutes and was always amazed at how they presented perfect V-shaped pubis in their hotpants or leggings. Curiosity got the better of her and she had asked one of them with whom she was friendly and the tranny explained to Julie how she tucked.

“I just know Alex, now step into these knickers,” Julie held open the waistband of the black satin knickers for Alex to step into.

Alex did as he was told and Julie shimmied the slinky garment up her son’s legs and she heard him sigh. She pulled the knickers up tight around his crotch and buttocks and smoothed them out with her long fingers, her red fingernail polish contrasting nicely with colour of Alex’s knickers.

Alex nearly fainted at the wonderful sensation of the silky satin gliding along his nylon-sheathed thighs. When he was alone in his room dressing, this was when he usually became sexually aroused and tonight was no different. He could feel his cock thickening and once again had to think of dead kittens to stave off a full blown erection.

It wasn’t just the exquisite feel of the silky tights on his legs and genitals and the scrumptious feel of the satin knickers gliding over them. Alex’s mother was quite a good looking woman for her age. She always wore makeup, tight clothing, short skirts, heels and hose. She was the kind of woman that Alex would like to look like when he matured and she also represented the type of woman he was attracted to sexually.

And here she was inches from him while he was presenting femme with his hair teased out, wearing full makeup and tights and she was smoothing out his satin knickers over his tights. She was hunched down and her legs, clad in gossamer hose, were opened slightly and her skirt had ridden up and the Vee of her pink nylon knickers was in full view. He could smell her perfume and her attractive face was looking up at him quizzically.

Julie understood that Alex was going through some mental queasiness which would explain the pained look on his face. It must be difficult for her son to comprehend that his mother was helping him to transform into a girl. Dealing with that must be very challenging indeed.

Then she realised that he was staring at her stocking-clad thighs and that her legs were open and her knickers were on display, the tight gusset moulded to the shape of her vulva. She had no issue with this. She sold her body for money to strangers and had done some things that she would rather not tell anyone about. One of her regulars just liked to stick his head under her skirt and sniff her crotch while he masturbated, then when he was ready he would come out from under her skirt and while she held her skirt up out the way he would spatter her tights and knickers with his hot spunk.

But this was her son and it just wasn’t right to be giving him an unobstructed view of her stocking-tops and knickers. She slammed her legs shut and gave Alex a reproachful grimace as she rose to her feet.

“Let’s put this bra on you,” Julie said gruffly, saying nothing about what had happened between them.

She picked up the brassiere and had Alex hold it against his chest while she adjusted the straps. Once again his mother was very close to him, her satin blouse rubbing on his sensitive freshly-shaved flesh, her perfume invading his nostrils. He could hear the swish of her nylons rubbing together as she fussed around him. And here he was he dressed in pantyhose and silky knickers wearing makeup with his hair styled in a bouffant. It was a little overwhelming and Alex felt his cock become a little stiffer.

“There. See how that sits? That’s how you wear a bra,” Julie turned Alex to the mirror again and Alex could see how he hadn't been wearing his brassiere properly before.

Julie scrunched up a few pairs of tights and stuffed the cups with them.

“Not ideal but at least it will give you some shape,” She said as she adjusted the bra a final time.

“Right. We’re nearly there. We just need to get you into the skirt and blouse,” Julie snatched up the navy blue A-line miniskirt.

She bent at her knees again and held open the waistband of the skirt for Alex to step into and Alex couldn’t help looking. He was rewarded with a glimpse of black opalescent stocking welt at the top of his mother’s thighs and the tight pink knickers clinging to the cleft of her pudendum and once again his penis, tightly held against his perineum, pulsed and became a little harder.

Julie eased the skirt up Alex’s legs, the lining rubbing sensuously on his nylon-sheathed legs and he couldn’t help but let out another little sigh. Julie looked at him quizzically but said nothing.

“Hold the waist open while I get your blouse,” Julie said, sounding a little annoyed.

Julie got Alex to put his arms into the blouse one at a time while he held up his skirt then Julie buttoned the blouse. Alex always struggled buttoning blouses because the buttons were on the other side to his men’s shirts. The soft satin felt cool and sensuous against his flesh and his mother tucked the tails of the blouse into the top of his skirt and closed the zip.

She fussed with the blouse and skirt until she was happy with the result, the hem of his skirt and the fabric of his blouse tickling him delightfully. He loved the flutter of the hem of his skirt on his nylons.

Alex was now sporting a semi-hard erection between his legs.

“Ok, we’re nearly there,” Julie said, snatching up the black high heeled court shoes.

One again she crouched down and this time Julie’s skirt rode all the way to the top of thighs and Alex stared, mesmerised, while his mother put first one foot then the other into the high heels. Julie’s fleshy but delicious thighs, clad in glistening fifteen denier black nylon stockings, the dark welts clipped to glittering garter snaps, were fully displayed. Alex could see the shape of her mound through her almost transparent knickers, the cleft of her pubis clearly visible.

His mother’s beautiful mature face was staring up at him, those full red lips, her rouged cheeks, her blue eyes highlighted by black eyeliner and mascara and purple and pink eyeshadow, all framed by her bottle-blonde fringe. Alex realised how sexy his mother actually was and why men paid to have sex with her.

His cock was now fully rampant.

“There. Now let’s get a couple of pictures so you can see how beautiful you look and so you can look at them when you practice your makeup and dressing skills,” Julie said enthusiastically, unaware of the effect her presence was having on her son.

Julie reached for the Polaroid Land camera that was sitting on Alex’s desk, a full cartridge of film inserted, ready to go.

She looked at Alex and was amazed at how pretty, sensuous and feminine her son looked. Alex was almost unclockable.

Then she saw that Alex had tented his skirt.

Alex’s erection had burst free of the confines of his perineum and his testes had descended and filled his scrotum. A hard proud erection was pushing against his tights and knickers, making his skirt bulge outward.

“Oh, for fuck sake Alex,” Julie sounded more disheartened than anything else.

“You’ve ruined the look. We’ll have to get rid of that before we can take any pictures,” she said disappointedly.

“I told you mom. When I dress up I usually get a… a stiffy and I have to… well you know what men do,” Alex repeated what he had told his mother earlier.

“Well you can’t wank yourself off wearing those clothes. You’ll get spunk on them and ruin them,” Julie sounded really piqued.

“Oh I know what’ll do the trick,” Julie snatched up a stocking off the bed and began to roll it up.

Alex just stood there dumbfounded.

“Don’t just stand there like a ditz Alex, lift your skirt up out of the way,” Julie grunted, sounding annoyed.

Alex couldn’t believe this was happening but he did as he was told and lifted the hem of his skirt all the way up.

Julie dropped to her knees in front of her son and pulled down his knickers.

His long thick cock was tenting the front of his tights; droplets of pre-ejaculate had already darkened the gusset. Julie dabbed at the droplets with the stocking and Alex shuddered as the most intense feeling he had ever felt rippled along the shaft of his penis shrouded in the sheer silky pantyhose being dabbed at by the nylon stocking which was held by his mom.

“Ok. Let’s get this over with,” Julie said matter-of-factly as if she was about to peel the spuds.

She whipped Alex’s long appendage out of his tights and rolled the stocking over it.

“The stocking will catch your load,” Julie said as plainly as if she was explaining how to put on socks.

She rolled the stocking along Alex’s throbbing member, once again impressed by how big her son’s cock was. Julie liked her cocks long and thick and for a fleeting second she wondered what it would be like to have this monster inside her.

Then she was all business.

At first the stocking was wrinkled and bagged, gathered around the shaft and flange of his phallus. Then his smother smoothed it out so that it was tightly swathed around his cock. She began to slide her fingers up and down her son’s big cock and Alex became weak at the knees. A gentle tingling began to bloom in his groin. His mother ruched the rest of the stocking around his scrotum and slowly squeezed and caressed the freshly-shaven sack.

Alex looked down and at his mother’s attractive face, her eyes glued to his bloated appendage. Her red lipsticked mouth had unconsciously formed a perfect circle, her long delicate fingers with those perfectly manicured red fingernails wrapped around his throbbing cock, stroking it sensuously, the diaphanous nylon eliciting a localised tingling in his penis that spread through his groin and centred in his lower belly.

The feel of the slippery, delicate fabric being buffed against his shaft, fraenulum and sensitive glans drove Alex to sensory overload and a climax ripped through him and his organ exploded.

Julie had put the stocking over her son’s cock to catch the semen not to enhance his pleasure but as Alex’s testes roiled and he ejaculated, the first eruption of scalding semen spewed from his cock and burst through the nylon and spattered on her cheek and in her hair. The second deluge of spunk splattered along her wrist and arm, then the stocking did its job and the rest of her son’s issue expelled itself into a glutinous puddle stuck to the stocking.

“There; that’s done it,” Julie said, seemingly proud of herself.

She ripped the stocking off her son’s cock and dabbed at the droplets of semen still dribbling from the eye.

“Keep your skirt out of the way Alex. If you get it on the fabric it hardly ever comes out,” Julie commented and got to her feet.

Julie held the semen soaked stocking in front of her at arm’s length and walked over to his desk and dropped it into the bin. She snatched a wad of tissues out of the dispenser on his dresser and wiped away the semen on her wrist and arm and dabbed at the spunk on her cheek and in her hair. She brushed her hair and applied foundation and powder to her face where she had wiped it away.

Alex just stood there dumbfounded holding his skirt up, his flaccid penis hanging over the waistband of his pantyhose; his knickers puddled around his ankles.

“What did you just do mother?” Alex whispered, sounding awestruck.

“I did what was necessary Alex. Don’t be obtuse honey; you know what I do for a living. What I just did, I do almost every day except it would cost you a few quid,” she walked back over to him and tucked him and pulled the waistband of his pantyhose back up.

She patted his false pudenda and smiled at him.

“Pull up you knickers, smooth out your skirt and let’s get these pictures taken,” she lit a cigarette and picked up the camera.

Julie got Alex to pose. At first they were just plain old portrait shots then she got him to pose a little provocatively and finally had him lie on the bed and she took some more seductive pictures. She handed Alex the pictures to look at and he had to admit that he was impressed. He looked amazing. Like a beautiful young woman dressed suggestively and posing erotically. The close-ups were perfect and he could use them as a template to practice his makeup skills.

But he still couldn’t get over the fact that he had been masturbated by his own mother. Not only that but she had invoked the most earth-shattering orgasm that he had ever felt.

“Now I want you to make your way carefully downstairs, holding onto the bannister and I’ll teach you how to walk in those heels and to ensure that your gestures are feminine.

They did just that, his mother sipping scotch and coke and smoking cigarettes while she trained him. She encouraged him, rewarding him with a break now and then to smoke a cigarette and have a drink with her. She made him sit with his legs crossed, dangling one foot seductively while he did so, with his shoulders back and tits thrust forward.

They were both amazed at how feminine Alex looked and how quickly he assumed a feminine persona. In her opinion he was almost passable.

While this was happening Julie secreted away a couple of the polaroids she had taken. She had taken so many that there was no way that Alex would know.

Over the next few evenings, between Julie servicing her gentleman callers, they spent their time doing the same thing over and over until Alex was passing perfectly. Alex also practiced his hair and makeup skills and deportment during the day.

In fact inside the house Alex had dropped his male persona entirely and presented only femme. Julie had even bought Alex a pair of rayon babydoll pyjamas to sleep in. Alex only thought of herself as HER not HE and Julie went along with it. Alex was first surprised and then delighted that her mother was so supportive.

There was no repeat performance of the sex. Alex kept fantasising about her mother masturbating her; she couldn’t forget it but despite some tacit encouragement Julie had not shown any further inclination to indulge Alex’s fantasies that way.

What Alex didn’t know about was Julie’s growing resentment towards her. Julie had resented her son Alex for being a lazy bludger and Julie had an ulterior motive for helping Alex become the girl that she wanted to be and the resentment and the ulterior motive had briefly been forgotten but it quickly returned.

Nothing had really changed. Alex still lazed around the house and made no effort to find employment or to compensate her mother for room and board. The only significant change was that Julie now thought of Alex in the feminine gender too. There was also an element of jealousy added to her resentment towards Alex.

Julie began to daydream about what it would be like if Alex had been born a girl rather than a boy and Alex personified what her daughter would look like if she had one. She was pretty, just like Julie had been when she was younger: long legs, nice tits (albeit false), a slim waist and rounded bottom. Alex exuded sensuality without realising it and if she went out she would be well aware of the effect that Alex would have on men.

Julie's daydreams became more embellished. The female Alex would be just like male Alex: no job, no prospects and no ambition; lazing away the days. But then female Alex would be different to male Alex because she would have lots of friends. A girl as pretty and vivacious as Alex would be very popular. She would be on the phone all day, chatting with her girlfriends about the latest celebrity hunk and which pop song on the charts was the best. Alex would be lusted after by boys in her same social class but she would turn her nose up at them. Her daughter Alex would be giving it up to upper-class boys with lots of money who had no intention of ever taking her home to meet their parents or heaven forbid marry.

Julie would have had to put Alex on ‘the pill’ as soon as she hit adolescence otherwise there would be another mouth to feed in the household when she got inevitably got knocked up.

Julie realised that her feelings of anger and jealousy were unfounded and it was just an elaborate fantasy that justified her envy and fuelled her illicit plans for Alex.

Julie took the polaroids she had taken of Alex posing seductively to the printers she used make her tart cards. Tart cards are cards advertising the services of prostitutes. The cards are placed in locations such as newsagents' windows and telephone boxes or alternatively they are handed out or dropped in the street in red light districts. The man who owned the shop printed tart cards for most of the ‘working girls’ in Birmingham. He insisted on being paid cash but he did a good job and his prices were reasonable.

Julie was on a break from the laundrette when she went to the printers and told the man who owned the shop what she wanted. Colour cards were twice as expensive as black and white and embedding an actual photographic image into the card instead of just a drawing also cost more money because of the skills involved. Julie paid half and then went out back of the shop and dropped her knickers and lifted her skirt and let the printer fuck her as payment for the remainder of the money she owed.

She’d let him shag her again when she came back to the shop to pick up the cards the next day.

Julie distributed the cards in telephone boxes, public house lavatories, newsagents and seedy hotel foyers around Balsall Heath. The picture on the card was of Alex posed seductively on the bed smiling salaciously. It read: Young and Exotic Transvestite. Discreet services for generous gentlemen. All of your fantasies come to life with this special young lady. At the bottom of the card was the phone number that Julie used on her own tart cards.

Julie’s home phone started ringing that night and she sorted out the genuine prospects from the weirdoes and prank callers. Some of the men baulked at the price that Julie was asking and she assured the potential clients that Alex was worth it. Julie whittled the prospective customers down to three men who would arrive at 32 Clifton Road at one hour intervals.

Julie would have her revenge on Alex and Alex would start paying her way.

“Let me help you dress tonight honey; I’ve bought you some special clothing,” Julie smiled at Alex who was dressed in her babydoll pyjamas and tights, curled up on the sofa reading a fashion magazine.

Alex liked that her mother was now referring to her as honey because it validated her gender and was a motherly term of endearment.

Julie led Alex up to her bedroom. She sensed that something was different. Her mother wasn’t being furtive but she seemed nervous and the phone had been ringing incessantly over the last two days but her mother didn’t seem to have any gentlemen callers.

“Ok honey. Tonight is going to be different. I’m going to help you dress again but tonight you will be entertaining. You will be showing off your femininity for the first time,” Julie smiled and the smile seemed a little evil.

Alex became alarmed and angry. She spied the tube of KY jelly on the bedside table and she shuddered at the very thought of what that implied.

“I don’t want to show off my femininity! I’m not stupid mom. You’re going to turn me out aren’t you? Well I’m not doing it!” Alex crossed her arms defiantly.

“Oh honey. You really think you have a choice? I have pictures of you dressed as a girl. Some of them are the awful ones of you took yourself and some of them are more recent,” Julie smiled at Alex evilly.

“You don’t have many friends but I know the few that you have and I know where they live. It would be so easy to push the pictures through their letterboxes. Then of course there is uncle Albert, aunt Doris, uncle Sid and aunt Mary not to mention your grandmother and granddad,” Julie continued.

“I’ll tell them how distraught and concerned I am about your crossdressing and when I show them the pictures they will recognise you. It doesn’t matter where you go I’ll follow you and show everyone the pictures,” Julie smirked.

Alex was speechless. She didn’t know if her mother was bluffing but the consequences would be awful if she did. Alex was not ready to share her secret and she knew that her family and the few friends she had would not understand. They would think she was some kind of pervert and likely disown her. Before she could answer Julie produced what looked like a little bottle with a tube attached to it.

“Go and poo Alex, then use this,” Julie held out a douche.

“I don’t wanna poo Mom,” Alex whined.

“Just do it honey. It will be better than what happens if you don’t,” Alex’s mother used her ‘don’t argue with me tone’ and Alex reached for the douche.

Alex wasn’t the sharpest tool in the shed but she knew what the thing with the red bulb and the white tube sticking out of it was used for. She felt trapped and subdued and she took the implement from her mother and retired to the bathroom and returned after a little while looking a little forlorn.

“Don’t worry honey. I think you might like what is going to happen to you tonight. You will finally become the woman that you always wanted to be,” Julie smiled at Alex who was not convinced.

Alex dutifully sat at the dresser while Julie helped her with her makeup. It was a lot more slutty than usual; dark eyes with lots of thick eyeliner and mascara and gaudy eyeshadow, rouged cheeks and bright red lipstick. Julie did her hair, fussing with it and using lots of hairspray.

Julie showed Alex a red satin basque with black lace trim and suspenders, a pair of red satin knickers and a pair of brand new red spiky high-heeled pumps and black fully-fashioned stockings. Ordinarily Alex would have been thrilled with the presents but tonight she was filled with dread as her mother helped her tuck and dress in the sexy lingerie, stockings and heels. When her mother fastened the clasps of her garters to the welts of her stockings then smoothed the stockings along her legs and straightened the seams the feelings of lasciviousness returned briefly.

Alex looked in the mirror and saw a whore staring back at her. A beautiful, sexy, deliciously feminine whore; but a whore none the less. Even the strong scotch and coke her mother had given her to drink could not take away the feelings of anxiety and when the doorbell rang Alex was filled with fear. Julie sprayed Alex with Dior Poison perfume and was about to go downstairs to answer the door when Alex caught her arm.

“What do I do mom?” Alex whispered.

“Oh that’s easy Alex,” Julie gently removed Alex’s grip from her arm.

“Just do what the nice man says honey,” Julie leaned in and kissed Alex’s cheek and went downstairs to answer the door.

Julie turned off the overhead light on her way out leaving the bedroom swathed in the seductive lighting of the bedlamps. Alex sat on her bed full of apprehension and alarm. She heard the click-clack of her mother’s high heels on the stairs and the clump of heavy boots behind her.

The door opened and her mother entered the room followed by a heavy-set man in his forties still dressed in his work clothes. Alex stared down at her shoes after looking up furtively at the man who without any encouragement sat down and began to undress.

“I’ll leave you to it. Alex this is Robert; be nice to him. Robert; you’ve got an hour,” Julie said sternly and quietly closed the door and left them alone.

Alex was shaking with fear when Robert approached her fully naked and sporting a healthy erection. He smelled of heavy industry, dried sweat, cigarettes and Ansells best bitter. He was also wearing aftershave which Alex thought he might have splashed on after work to try to hide the other odours. Alex thought that Robert smelled very manly and somehow that made her feel more feminine and vulnerable.

“Let’s see your pretty face then sweetie,” Robert put his big paw under her chin and lifted it so that the lamp illuminated her face.

“My god you are stunning,” Robert sighed.

He lowered his face to hers and for the first time in her life Alex kissed a man. Robert’s thick lips pressed against hers and Alex froze. She didn’t back away but she didn’t respond either. It was strange to feel Robert’s full lips on her lipsticked lips, to feel his breathing, to smell his manly body, to feel the presence of this older, bigger man. She was still scared but the fear was manageable. She was in her own house in her own bedroom and her mother was downstairs.

Robert pressed his lips harder against hers and Alex opened her mouth a tiny little bit to breathe and Robert took advantage and pushed his tongue into her mouth and eased her back on the bed and lay on top of her, kissing her. Alex allowed herself to be lowered onto the bed; she knew that fighting this brute was out of the question. Also, somewhere deep in her psyche where she seldom went, Alex had a feeling that she deserved what was happening to her. Her mother was right; she was a bludger who needed to pay her share.

Robert rolled Alex onto her side and lay beside her, holding her close, kissing her, his hands meandering over her body, fondling her, caressing her, squeezing her.

“I want a bit of kiss and cuddle before we get down to it,” Robert stopped kissing her long enough to speak.

‘Get down to what?’ Alex thought.

He pulled her close and kissed her again, his fingers squeezing Alex’s buttocks, then sliding along her thighs and stroking the welts of her stockings. Robert seemed infatuated with her silky stockings and stroked her legs for quite some time, tracing the seams of her stockings, kissing her and holding her close. If anything, Alex was confused. This brute of a man was holding her close but he wasn’t hurting her. On the contrary he was softly fondling and caressing her. His kisses were gentle and he was whispering little compliments in her ear.

It was strange being cuddled by this older, bigger man and Alex was still fearful about what might come next but for now the experience was not too unpleasant. Robert made her feel like the girl she imagined she was and she felt comforted and cosseted. She opened her lips a little wider and let Robert put his tongue all the way into her mouth and she reciprocated, putting her own tongue into Robert’s.

He tasted of beer and cigarettes but she didn’t find it that unpleasant. Robert tasted like a man should. On the other hand Alex tasted sweet and smelled delicious, drenched as she was in the musky stench of Poison perfume. She felt soft and the feel of the satin corset and silky stockings against his flesh were driving Robert wild with lust.

It was then that Alex became aware that something was pressed into her stomach. Something hard and fleshy and warm.

Robert took her hand and guided it down his body, past his protruding belly into his hairy crotch. Alex’s fingers glided past a fleshy appendage that she realised was Robert’s erect penis. Robert pulled her hand back near the inflamed organ and her fingers brushed it again.

“Take it!” Robert hissed into her ear.

It was the first time that Robert had shown any anger but she figured that it was more frustration than ire in his voice. In any event it stirred Alex out of her reverie and she took Robert’s hard, pulsing phallus in her hand. It felt warm, fleshy and hard and Alex traced a throbbing vein with a manicured, red-nailpolished fingernail and then she squeezed it and she felt Robert shudder and he moaned.

“Oh god yes!” he whispered into her ear.

It was now that Alex realised that she was the one with the power. Robert was the one begging her for release. Alex knew what it was like to be like one of those pretty girls who shunned him and thought they were too good for him and refused to even return his stare. Alex was now the one who was admired, lusted after, cherished. She began to slowly stroke Robert’s cock to see what would happen next.

He writhed against her and kissed her harder and lustfully drove his tongue into her mouth. His hands were everywhere, stoking her stocking-sheathed legs, scrunching her satin-encased buttocks, even inside her bra tweaking her nipples. Julie hadn't padded Alex’s brassiere because she suspected the customers might want to play with her meagre little titties and she was right.

Alex’s breathing began to become ragged as feelings of lustfulness replaced the feelings of trepidation. The sensation of Robert’s rough hands stroking her gossamer-clad legs was wonderful and when he squeezed her knicker-clad bottom she squealed a little and giggled like a girl. She was suddenly aware that she was erect; her cock had sprung free from between her legs and was pushing against the front of her knickers.

Robert rolled Alex on her back and mounted her and for a few seconds Alex was terrified that he was going to try to fuck her but he continued to kiss her passionately and began to grind his cock against her knickers, thrusting his phallus against hers with the only the slippery satin knicker fabric between their engorged members.

Instinctively, Alex wrapped her nylon-sheathed legs around Robert’s flanks and rubbed her stockings on his bare flesh and scraped her heels along his back and she felt him buck and shudder. He whimpered like a braying animal at the pleasure he was experiencing from the feel of Alex’s legs and heels on his sensitive skin, her lips on his mouth and her tongue inside it, her fingernails raking his back as she writhed beneath him, thrusting her satin-swathed cock against his hard, pulsing member.

Pleasure was everywhere and Alex was roiling in it. Her cock was throbbing with delight as she felt Robert’s penis rubbing and pulsing against it, her body was alight with delightful sensations as Robert kissed and caressed her. Alex had never felt so sexually energised and so womanly.

Robert suddenly drove Alex into the mattress and held her there with the weight of his body pressing down on her. He ground his cock against hers forcefully and drove his tongue into her mouth as he cried out.

Alex felt the sudden warmth and wetness as Robert ejaculated on her. Robert’s semen soaked her knickers and ran down between her legs. Her own cock erupted and she clung to him and ground against him as both of their phalluses throbbed and spewed forth their scalding issue. Wave after wave of pleasure enveloped Alex as Robert continued to kiss her, caress her and grind against her. She crossed her ankles behind his back and held him close, returning his kisses as the last of her orgasm washed over her.

Alex was overcome with post-coital regret once she came down from her orgasmic high. There was an old fat man lying on top of her, rubbing his cock on her semen-drenched knickers and slobbering at her with his thick rubbery lips. The fantasy of the young girl being taken by the older man had vanished as the reality of the situation dawned upon her.

Alex lay under Robert and let him finish and then he climbed off her and smiled down at her, his once proud erection slowly subsiding like a snail retreating into its shell.

“That was awesome kid. I’ll pay your mom on the way out,” Robert leaned down and kissed her cheek and then began to dress hurriedly.

Alex just lay on the bed with puddles of semen soaking into her knickers and between her buttocks, slowly cooling and coagulating. She felt like a used whore. She silently berated herself for enjoying and actively participating in the sex. How easily she had succumbed. She was a harlot just like her mother!

She listened to the clomp, clomp, clomp of Donald’s boots descending the staircase and the hushed conversation between her mother and the man who had defiled her. Then the squeaking of the front door opening and closing followed by the click-clack of her mother’s high heels on the stairs.

“Get up and clean yourself up you floozy,” Julie hissed at her daughter when she saw the mess.

“Your next gentleman caller will be here soon and you need to be ready.” Julie put down the scotch and coke she had carried upstairs and rummaged in the drawers for a fresh pair of knickers for Alex to wear.

Alex pulled down her knickers careful not to get any spunk on her stockings or her basque. She wiped between her legs and dabbed at her genitalia until they were sufficiently dry enough for her to walk to the bathroom. She went to the basin and filled it with warm water and took a flannel and washed and dried her genitals and buttocks. Alex came back into her bedroom and tucked and stepped into the full-cut black nylon knickers that she snatched from her mother’s hand. She pulled them tight and sat down.

“Here drink this,” Julie handed Alex the scotch and coke and Alex drank most of it one gulp.

Julie lit cigarettes for them both and handed one to Alex who sucked the menthol smoke deep into her lungs.

“I won’t ask you how it went because I saw the results. Regardless of your attitude I think you quite enjoyed it; Robert certainly did. I’m charging the punters three-times as much as I charge for myself because you are so young and inexperienced but Donald didn’t complain, in fact he left a tip and told me he’s coming back next week,” Julie seemed proud of herself but Alex just sulked.

“Ok stop behaving like a baby! You wanted to know what it feels to be a woman, well now you know - you spend a lot of time on your back with men you don’t really like pawing at you,” Julie snatched the glass out of Alex’s hand.

“Fix your makeup; your next punter will here in five minutes,” Julie snapped and left the room.

Alex did as she was told; there was no time for crying or self-pity.

The next man to arrive was named Andrew and he a lot younger than Donald and Alex had to admit that he was quite handsome. He kissed Alex affectionately and she willingly let her hand drift to his flies and extract his long slim member. Her intention was to do exactly what she done with Donald: kiss, cuddle, fondle and dry-hump. It was pretty easy work when she thought about it and this man was quite nice.

But the best laid plans of mice and men often go awry and so did Alex’s. When she tried to get him to lie down on the bed Andrew had other plans. He forced Alex to her knees and jabbed at her mouth with his cock.

It was over quickly.

“Come on luv; give it a bit of a suck before I fuck you,” Andrew laughed almost manically.

Despite his younger age and handsomeness, Andrew was a brute compared to Donald.

Alex was on her knees with her pretty blue eyes looking up into Andrew’s handsome but merciless face. He put his hand on her jaw and forced her mouth open. He grinned as his long slim cock slid over her lips, her lipstick leaving a red smear on the smooth translucent flesh.

Alex had heard Andrew say the words ‘before I fuck you’ and knew what she had to do. She looked up into Andrew’s cruel eyes with her own wide big blue eyes that were full of fear. Alex guessed that Andrew would get off on this. She tentatively suckled his cock, using her lips on the shaft, slipping her tongue under the glans, licking his fraenulum.

Andrew gasped and entwined his fingers in her blonde locks and began to fuck her face. Once Alex learned to breathe in and out through her nose the task became simple. All she had to do was suck on Andrew’s appendage. It was long but not thick and she could easily accommodate him in her mouth.

Within minutes Alex had become an accomplished fellatrix. She suckled his bloated phallus, stopping frequently to pop it out of her mouth and kiss and caress it and then when she felt him become insistent she slipped him back into her mouth and went back to work with her lips and tongue. She slathered her tongue around the underside of his glans, swallowing the sweet nectar of his precum and worked her lips up and down the shaft.

She used one hand to lightly caress his scrotum, alternatively tickling it with her fingertips and then slightly scratching it with her fingernails. Her other hand snaked up his body and tweaked a nipple.

The desired result took quite a while to be realised because as soon as Andrew felt he was about to climax he would rip his cock from Alex’s mouth, drag her to her feet and kiss her and fondle her and begin the process all over again. If Alex was honest with herself she would admit that she was beginning to enjoy being treated a little roughly and enjoying the ongoing tension of bringing Andrew close to release and then backing off.

In fact she began to do just that without further encouragement. She sucked his bloated organ, swallowing the bitter-sweet pre-ejaculate and then she immediately stopped when she felt it begin to pulse prior to extremis. Then she would leap to her feet and press her body against him like wanton whore, kissing him with her lipstick-smeared mouth, her fingers raking his flesh, her stockinged leg snaked around him, grinding her pubis into his.

Then she would drop to her knees and start sucking him all over again.

Andrew moaned and groaned and whined and whinnied until he couldn’t take it any longer. This slattern’s mouth was driving him insane.

He clamped one hand either side of her face and fucked Alex’s mouth until his scrotum roiled and his cock exploded.

Alex tried to swallow all of the musky issue as it spewed from his cock but she couldn’t and a runnel of creamy white spunk ran down her chin. Alex looked down at her pretty face: her eyes filled with trepidation and shock, her pretty mouth stained with smeared lipstick, her eye makeup smudged, eyeliner and mascara running down her cheeks as tears filled her eyes.

Andrew ripped his cock from Alex’s mouth and spattered that last of his issue on her face. Clumps of hot semen splattered across her cheeks onto her eyelashes. A second smattering of his essence spurted onto her lips and her chin. A third rope of scalding sperm fell onto her platinum locks, a string of semen dangled from her fringe like an accusatory stalactite. Her face was a mask of ruined makeup and spattered semen. Despite the mess she was still beautiful to look at.

Andrew’s breathing was deep and erratic. It was one of the most forceful orgasms he had ever experienced. His only regret was that he hadn't fucked her.

He guessed that it might have been her plan all along: suck him to climax so that he wouldn't fuck her. Well he was definitely going to fuck her the next time he came to 32 Clifton Road and that would be soon. The gorgeous young tranny was eminently fuckable!

Andrew wiped his cock on Alex’s face, comingling his semen with her makeup; a last act of defiance and punishment.

Alex fell to the floor and hugged herself. She felt sorry for herself but also disgusted with herself. Despite her feigned indignation she was sporting an erection. Her cock was pressing against her flimsy nylon knickers and it was rampant. Although she felt used and debased she also felt powerful and in control. She had made Andrew act the way she wanted him to act; to become angry and impatient and fuck her mouth and surrender his seed so that he was spent and unable to fuck her.

Alex lay silently on the floor until Andrew left the room then she leapt to her feet and scampered to the bathroom on tottering high heels. She looked at her face in the mirror: still pretty but her makeup smeared and ruined and comingled with Andrew's drying semen. She looked disgusting. She looked like a slattern. But she desperately wanted to take her penis out of her knickers and stroke it furiously while she looked at herself but she resisted the urge.

Instead she washed the semen off her face and wiped it out of her hair and went back to her room and redid her makeup: heavy and slutty just like it was before and she coiffed and sprayed her hair.

“You must have done a really good job on Andrew. He’s booked you for an hour next Friday and he left you a generous tip,” Julie chuckled and handed Alex another scotch and coke; this time it was a double.

“It was awful! It was debasing and disgusting,” Alex whined.

“If there was any way to stop this I would,” Alex huffed.

“Methinks the lady doth protest too much,” Julie chuckled.

“What am I to do mother? Where am I to go? Who am I going to tell?” Alex snapped at Julie and gulped at her drink.

“Oh don’t be so dramatic. It’s only sex! You’ve only got one punter left to go and you're finished for the night. You will have earned more in one night than I earn in a fortnight so stop your whinging,” Julie snapped.

They both smoked in silence and Julie helped Alex properly adjust her clothing and fix her makeup. For a few seconds it felt to Alex like they were mother and daughter. They had both just finished their second cigarette and third scotch and coke when the doorbell rang and the ritual continued.

Dennis was in his early thirties, handsome, virile and eager.

He eyed Alex up and down and smiled at her.

“You are the most beautiful thing that I have ever seen,” Dennis whispered as he began to undress.

Alex was over it by now. Two men had used her for their pleasure and she had submitted to both but she felt guilty about it after. She lay on the bed and watched Dennis undress. He turned towards her and he looked even more handsome naked. Dennis’s limbs were muscled, his pectoral muscles well-defined and his stomach flat as a washboard. His cock was long and thick and swung from side to side, semi-erect already as he approached the bed.

“What do you want to do?” Alex just wanted to get it over with.

“I want to fuck you of course,” Dennis smiled down at her and he reached out and stroked her blonde hair.

Alex shuddered. Dennis’s cock was inches from her eyes and the very thought or that monstrous thing going anywhere near her anus made her baulk.

“Let’s do something else,” Alex reached out and took Dennis’s massive cock in her hand began to stroke it.

It was sleek and warm, the veins defined and pulsing, the pink glans exposed and glistening with dewy pre-ejaculate. Alex felt the appendage grow in her hand as she caressed it. It seemed to throb with tantric energy. She felt both terrified and powerful and also a little ashamed.

The thought of having to suckle this monster cock or even worse, allowing it to enter her was terrifying but the power she held over this man was thrilling. Dennis was mewing and groaning; encouraging Alex to stroke his phallus; almost begging her.

“Oh yes honey, oh that is so wonderful, please don’t stop, yes… that’s it… right there… oh my god!” Dennis moaned; his knees trembling as Alex caressed his cock.

She cupped his large scrotum and gently squeezed and stroked it whilst the fingers of her other hand featherlightly ran up down Dennis’s engorged penis, her fingernails gently scouring the velvety flesh, the pad of a finger circling his fraenulum. His cock was rock hard a runnel or clear pre-ejaculate hung from the glans in a silver thread.

It was this that made Alex feel powerful. She could feel her own cock awakening inside her knickers.

And this is what also made Alex feel ashamed.

Alex had only been with two men and already she was behaving like a slattern but even worse she was enjoying the power of it; the sexual energy, the need that the men had for her; their lust for her; their craving. She was scared that it might become addictive.

The bedsprings creaked as Dennis climbed onto it and lay down beside her. Her hand was still on his cock, stroking and caressing the sleek appendage and when Dennis put his lips on hers she kneaded it a little quicker and squeezed it a little harder. She willingly opened her mouth and her tongue met Dennis’s and they intertwined as Dennis pulled her close and pressed her body to his.

They kissed languidly; their passion bubbling away just below the surface. Dennis stroked her hair and told her that she was beautiful and sexy and delightful, between bouts of kissing. His hands began to explore her body, stroking her stocking-tops, softly caressing her bottom, circling her nipples on her flat chest.

His handsome face began a journey. His mouth suckled her earlobes and he nipped them gently, he softly kissed her neck and the hollows of her shoulders, down her décolletage to her tiny breasts. She hadn't padded her breasts exactly for this reason; although she didn’t have any real heft to her breasts she did have very sensitive nipples and Dennis’s lips and teeth found them.

He peeled down the top of her basque and his mouth fell on her little breasts, his lips sucking on the tiny teats, his teeth nipping her nipples gently. Her nipples hardened and she growled deep down in her throat. At the same time Dennis’s fingers squeezed her plump buttocks a little harder and it felt heavenly.

Alex’s cock had sprung free of the confines of her perineum and tented the front of her knickers and when Dennis’s hand drifted across her stocking-sheathed thighs and brushed the engorged organ she shuddered. It was the first time a man had ever touched her there and she liked it.

She gripped Dennis's cock even harder and began to stroke it vigorously. She wanted him to climax quickly, not because he was hurting her but because she was enjoying it and she felt that she shouldn’t.

“Please don’t,” Alex tried to push Dennis’s hand away from her groin.

This only made Dennis more insistent and he caressed her throbbing organ through her knickers and put his mouth on hers. Alex shuddered with the ecstasy of it. The taste of Dennis’s mouth, his lips crushing hers, his tongue exploring her mouth, her nipples still burning from where Dennis had lapped and nipped at them, her thighs tingling from the ghost of his caresses and her cock radiating circlets of intense pleasure as Alex stroked it.

Alex rolled over on her back like a slattern and opened her legs so that Dennis could climb on her; his cock pressing against hers, the silky gossamer of her knickers intensifying their pleasure. They kissed fervidly, her heart beating faster, her breathing ragged. She locked her legs around him and pulled him tight, her lips crushing his, their tongues deep in each other’s mouth.

The circlets of pleasure radiating from her crotch intensified as Dennis ground his cock against her, rubbing it, pressing it, humping her. Dennis could feel Alex’s cock, fully engorged inside her silky-soft knickers. He liked the feel of it pressing on his organ; the slippery knicker-fabric enhancing the sensation.

Alex was no longer reticent and Dennis decided it was time to strike while the iron was hot.

He’d spied the lube of lubricant on the bedside table and his fingers scrambled for it, clumsily unscrewing the cap with one hand. He squeezed a dollop of the viscous gel onto his hand and smiled at his ingenuity. Alex had no idea what he doing.

She first became aware of it when Dennis slipped a hand inside her knickers and pushed the viscous gel between her buttocks, onto her puckered sphincter. The gel was slippery and cold and shouldn’t be there and Alex began to panic.

She unhooked her legs from around Dennis’s body and beat her hands on his chest, trying to drive him off her but Dennis just persisted and eased the gusset of knickers aside and pushed his cock into the crevice between her buttocks.

“Stop! Don’t!” Alex screamed.

“Ready?” Dennis smiled down at her as if he hadn't heard a word she’d said.

He covered her mouth with his to stifle her screams as he slowly impaled her on his enormous, engorged phallus.

Alex felt like she was being ripped open by a red hot poker. Her sphincter stretched until Dennis’s glands were able to pierce it and then the full length of his shaft slowly distended her virgin anus. Dennis pushed until it was fully inside her and his scrotum bounced on her perineum.

The pain was unimaginable. It almost felt like he was tearing her apart. But at least Dennis stopped when his penis was fully inside her and Alex’s screams became gentle sobs

“I’m sorry; I didn't know this was your first time. You’re a brass; I thought you’d had hundreds of cocks up you,” Dennis whispered trying not to orgasm because Alex’s anus was gripping his cock like a tight sheath.

“I'm not a brass!” Alex was able to whisper indignantly through the pain.

She realised how phoney this sounded. Hadn't she just had sex with two men for money?

“Well I wasn’t but I am now,” Alex pouted.

She realised how silly this sounded coming from a transvestite lying on her back wearing full makeup, dressed in a sexy basque, fully-fashioned stockings, slinky knickers and high heels, with a man lying between her legs with his cock buried up to the hilt inside her.

“I suppose you are. But you are still beautiful and adorable,” Dennis kissed the tip of her nose.

“This coming from a man who has his cock stuck up my arse,” Alex whined.

It was then that she realised that the pain had gone away. Not only had it gone away, something wonderfully decadent had replaced it. A deep perception of delectability was radiating from her prostate and as Dennis’s cock continued to press on it the feeling intensified into a sphere of sexual bliss. Her stretched sphincter was no longer aching; it was emitting little sparklets on intense pleasure. Her anus felt full and bloated but in a good way. She was accommodating Dennis’s engorged phallus quite comfortably now.

“Well come on then. Do what you said you were going to do. Fuck me,” Alex said sulkily and looked up at Dennis with a challenging grimace on her face.

Just hearing her say ‘fuck me’ was enough to send Dennis over the top.

He gripped Alex by the shoulders and thrust once, twice three times and then he ejaculated deep in her bowel.

Alex grimaced and grunted each time Dennis’s cock thrust in and out of tight channel. As he did so his hard belly pressed on her engorged cock, still trapped inside her knickers. It was heaven.

She felt Dennis ejaculate deep inside her. His cock shuddered and she could feel his scalding semen filling her anus. His whole body shook with a paroxysm of pleasure and his mouth fell on hers and he kissed her passionately as he voided his essence inside her.

Instinctively Alex wrapped her diaphanous-sheer-stocking-clad legs around him, her high heels raked his flesh as they drummed on his muscled black. Her nails tore at his skin and she raised her hips to grind against him as she filled her knickers with her issue. Her sphincter palpitated and clung to the shaft of Dennis’s cock as he rammed it in and out of her tight channel, the spongy mass of her anus clutched his throbbing cock, milking him of his seed and his glans spewed forth the viscous profusion of his semen and pressed on Alex’s prostate, intensifying her orgasm into a mind-blowing blissful explosion of pleasure.

The two lovers clutched at each other, reluctant to relinquish the satiety that they felt in each other’s arms.

Alex’s big blue eyes gazed up at Dennis’s handsome face.

“Do that again,” she whispered and she pulled him close, her ankles locked behind his back as he wriggled her body under him.

Dennis smiled down at her and kissed her and then he granted her wish and he did it to her all over again. This time it was slower and more loving, each of them extracting every scintilla of pleasure from the other.

When Dennis was sated and could no longer perform and Alex’s anus was numb, but in a wonderfully decadent way, they said their goodbyes. Alex escorted Dennis to the landing at the top of the staircase and kissed him farewell with a long lingering kiss.

Julie stood at the bottom of the staircase and smiled up at them.

Dennis paid Julie the agreed stipend and added a generous tip and told Julie that he would be back soon to see Alex. Julie closed the door to 32 Clifton Road and looked up at Alex who leaning on the newel post smoking a cigarette and drinking the remaining dregs of her scotch and coke.

“I’ll take four gentleman callers tomorrow night mother. Bring me up a fresh drink please,” Alex smiled smugly at her mother then turned away.

The End

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joannebarbarella's picture

A Michele Nylons story, pushing all those pornographic buttons which are your trademark. I wish Julie had been my mother, not for the introduction to her profession but for the acceptance and assistance in promoting my internal girl.

Definitely not

One of grandma's stories. I gave up smoking 8.5 years ago and I find myself severely tempted. Another powerful work from Michele Nylons
Steamy keyboard.

Thanks. I needed that.


Well crafted

And the cautions are all there, so while this is certainly no Hallmark-style ending, it most definitely a Michele Nylons story. Very good.

>>> Kay