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.

But...

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.