In 1959 Brian Macklin was in his mid forties and was making just enough money to get along; his dreams of affluence were ruined when his marriage failed. He used to be a sales executive for an affluent London based firm but all of that came to an end when his wife left him; his father-in-law owned the firm where he worked; say no more. To make matters worse his father-in-law was a vengeful bastard and poisoned the well; none of the high profile London firms would touch him with a bargepole. I suppose fucking his sister-in-law in the billiard room at the family's country house wasn't the smartest thing Brian had ever done.
He had fond memories of lifting his plump but pretty sister-in-law up onto the billiard table, hiking up her skirt, pulling aside her knickers and ploughing her like a spring field while her silk stocking encased legs rubbed against him. It would have been the perfect end to a boring family weekend get-together; if his pratt of a mother-in-law hadn't come into the billiard room unexpectedly and started screaming her tits off.
It's not like his sister-in-law was any sort of chastity figure; word around The Club was that she had had more pricks in her than a second hand dart board; but that didn't help Brian at all when it came to his wife's family's family retribution. His sister-in-law had claimed that Brian had forced himself on her, even though she had been trying to seduce Brian for six months: asking him if her seams were straight; if she had any snags or ladders; or if he would clip a loose garter strap onto a stocking welt. She'd figured out Brian's weakness for stockings as soon as she had met him and used his fetish to seduce him; she always got what she wanted. Another story going around The Club was that when she was a young girl; she'd show you her knickers for a bite of your toffee apple.
So, Brian's weakness for stockings had finally bought him undone. He'd been forced to move to the midlands where the best he could do was to land a job as a door to door hosiery salesman. He rented a small bed-sit in Birmingham and made the rounds of local firms offering his sales executive credentials, but nobody wanted him; a salesman job was the best he could do. At first the wages were crap, the hours long and the rewards few. The only reward was that he got to sell his favourite fetish item: stockings. He went door to door lugging his sample case. He sold some socks and those horrible winter tights too; but this was an era before pantyhose, which would not be invented until 1965 when miniskirts became the fashion, and most women wore nylon stockings. He sold nylon stockings, silk stockings, seamed stockings, fully-fashioned stockings, seamless stockings, black stockings, white stockings, flesh-toned stockings, translucent stockings and fishnet stockings. If there was a style of stocking on the market he sold it.
Brian loved stockings; his earliest memory of his fetish was the touch and feel of his mother's stocking encased legs when he was a young boy. There was nothing sexual about it at first; it might just have been an innocent brush against his mother's leg as she hugged him or the feel of her legs when he sat or lay in her lap being cuddled and kissed. He also had memories of watching his mother getting dressed in her lingerie and hosiery when she was getting ready for work or dressing to go out for the evening. The sheen of her stockings fascinated him.
Brian became sexually aroused by nylons when he entered puberty and he had stolen some of his mother's hosiery as an aid to masturbation. This practice ceased abruptly when his mother asked him about some suspicious stains that had mysteriously appeared on a pair of stockings that she had hung up in bathroom to dry overnight. She didn't actually accuse him of masturbating in them but the implication was clear; and after that day he noticed that she never left her hosiery or lingerie in the bathroom at all; not even in the dirty laundry basket. It was an unspoken secret between them that his mother knew of his fetish.
Brian turned to snowdropping, the practice of stealing clothing off the neighbours washing lines. At first he stole only nylon stockings but progressed to stealing knickers and occasionally brassieres if they took his fancy. A few of the neighbours complained to his mother, which bought another lecture from her; again there was no direct accusation, but there was a tacit agreement that he would cease snowdropping. Brian noticed that after this discussion his mother began to openly leave her discarded hosiery in the kitchen tidy, whereas previously he had no idea how she discarded her laddered nylons; he had searched the rubbish for them on numerous occasions but he never found them. The first time he discovered a pair of his mother's discarded stockings, he saw a silken reinforced foot dangling from the kitchen tidy like to attract a lure to a predator. Was this a mother's tacit ruse to prevent her son's fetish getting him into more trouble?
In 1959 Mike was in his late forties; a widower who had never remarried after his wife died almost ten years earlier leaving him childless. He made a modest living as an accountant working from his two bedroom semidetached house in Moseley, just outside of Birmingham. As he ran his business from home he could vary the hours he worked to suit himself. Once a week he collected the accounts from several small businesses in the area and then returned them to the firms when he had completed working on them.
This was a very satisfactory arrangement for Mike who lived alone, had few friends and had deliberately declined to engage socially with his neighbours. They thought he was stuck-up and were happy to avoid the snotty recluse who lived at the bottom of the cul-de-sac at 162 Sovereign Way. Mike's only sister lived all the way down in Plymouth and she seldom visited him. Mike kept to himself and valued his privacy.
Mike did have one interest outside of the house though; he volunteered as a clothing sorter at the local Oxfam twice a week. People donated their used clothing to Oxfam and sometimes businesses would donate excess or out of date clothing stock or factory seconds and it was Mike's job was to sort through it and separate the clothing into various categories. Firstly men's and ladies clothing were separated and then the clothing was further sorted by type, such as: shoes, trousers, shirts, hats, underwear and so forth. But Mike didn't like to sort men's clothing; he made it a point to work on the tables where the ladies' clothing was sorted.
Mike was a secret transvestite and he acquired all of his women's clothing, shoes, cosmetics and wigs from Oxfam. Everyone that worked there knocked off some of the good stuff from the sorting tables; it was an unacknowledged perk of the job, the supervisors even knew about it. There was really nothing they could do about it anyway, because it was hard to get volunteers to work there during the week, so they turned a blind eye. Mike liked to work there on Mondays and Fridays when very few volunteers turned up and he could often work alone picking over the piles of clothing and other donations that the donors dropped off. He once managed to get a complete cosmetics kit that had hardly been touched; he was also quite surprised how many women threw out their old wigs.
Mike soon had quite an extensive wardrobe at home full of women's clothing as well as a large collection of shoes, lingerie, wigs and cosmetics; all provided courtesy of Oxfam. He would gladly have paid for all of it, but in 1959 middle-aged men didn't go shopping for women's clothing; it was almost unheard of. The most difficult item of feminine apparel for Mike to source was good quality stockings. The rule at Oxfam was that donated second-hand underwear was to be disposed of for sanitary reasons, or it was to be thrown in the rag bag; but Mike had stolen some lovely second-hand lingerie from the sorting tables.
The problem was that women never threw out their stockings until they were laddered or holed beyond wearing. On the very rare occasions that hosiery made it onto the sorting tables at Oxfam they were usually inferior high denier 'old lady' stockings or those horrible ribbed tights that women wore during winter. No! Mike's biggest challenge was getting his hands on good quality hosiery.
Mike had had a fetish for wearing women's clothes for as long as he could remember. As a teenager he had tried on various items of his sister's and mother's clothing on the rare occasions that he was left at home on his own. He loved the feel of their lingerie against his body and the smell and taste of their cosmetics. After nearly getting caught dressed in his sister's suspender belt, stockings, knickers, full-slip and heels; his face garishly painted with makeup, he decided he would stop giving into his obsession. He ran and locked himself in the bathroom; scrubbing the makeup from his face and changing out of his sister's clothes and into his own, whilst she knocked incessantly on the door complaining that she had to use the toilet. He realised how close he had come to having his secret discovered just because his sister had returned home early from her friend's house in Acock's Green.
He had to hide the clothing that he had stolen from his sister and then hurriedly sneak it back into her room whilst she was downstairs having dinner that night. Later that night Mike's sister complained to their mother that her best sheers had a ladder in them and accused her mother of borrowing them without asking permission; which their mother of course denied. Mike's sister looked at him quizzically for a few days after this incident but she never said anything to him; however the whole episode scared Mike from ever crossdressing again; besides only homos and noncers would want to wear women's clothing, he rationalised.
Mike was still attracted to women who dressed attractively though; and paid particular attention to girls who wore nylons, high heels and makeup as part of their daily dress convention. He had had a particularly satisfying sex life with his late wife who had shared his penchant for lingerie, quality hosiery and high heels. She would let him play with her legs for hours whilst they cuddled on the lounge as a precursor to sex and she was quite prepared to leave on her makeup and lingerie during sex provided that Mike was willing to keep replacing her stockings when they laddered. Mike had fond memories of wearing lingerie when he was younger; but he never got up the nerve to ask his wife if she would mind if he wore some of her intimate apparel. He thought that she would either laugh at him or leave him, or probably both.
After his wife died things changed for Mike. He moved to the small detached house in Sovereign Way and became more and more reclusive. Reliant on masturbation for sexual gratification it didn't take him long to start fantasising about wearing women's clothing; especially now that he had an opportunity to do so with little chance of being caught. He completely shaved off his body hair and started wearing some of the clothing that his widow had left behind, but most of it was too small. His wife had been petite and Mike was an average built male of about five nine and one sixty-five pounds. The only things that his wife had left him that he could really use was her jewellery (in the nineteen fifties clip-on earrings were still quite popular) her perfumes and her cosmetics. He dieted until he was as thin as he could get at one fifty-five pounds but he soon realised that he would need to get his own collection of women's clothing if he wanted to crossdress properly.
He solved this problem by getting the volunteer job at Oxfam. After a year of crossdressing he was quite adept at adopting a female persona; he mastered the intricacies of makeup and had even developed a husky feminine voice and a sexy walk. When he was dressed he called himself Michele and spent many a long afternoon and evening dressed as Michele, slowly arousing himself until he couldn't take any more simulation and the need to relieve himself became overwhelming. The one thing that eluded him was how to acquire good quality stockings. He'd bought some from a local lingerie shop; but he had nearly died of embarrassment when one of his neighbours walked in and asked him who he was buying them for. He spluttered something unconvincing; like they were a present for his sister, or some such rubbish. In 1959 men rarely bought lingerie for their wives; so why would he be buying stockings for his sister?
Mike tried using mail-order after getting his hands on a hosiery catalogue, but the Royal Mail derailed his plans; packages from retailers required a return address and the contents of the package had to be listed on the collection slip. Mike spent the most uncomfortable fifteen minutes of his life with an over-inquisitive female mailroom clerk discussing why he was ordering nylon stockings through the mail.
Mike's crossdressing fantasies were also becoming increasingly vivid. He imagined himself as Michele, held in the arms of a faceless but undoubtedly handsome stranger who romanced, kissed and caressed her. He didn't allow the fantasy to progress any further than that but he was developing an uncontrollable urge to be in the company of a man whilst he was dressed as Michele. He doubted that he would ever be able to do so because there was no safe and discrete way of doing so.
He was aware that there were some clubs in London where transvestites solicited male partners but there was no way he could do that. The logistics of it alone made it impossible; he would have to find a hotel in Soho where could transform into Michele and then he would have to brave walking the streets dressed as a woman just to get to the club. My god; if he got caught dressed as a woman or even worse, charged with soliciting, his life would not be worth living; no, that idea was far too dangerous. He'd also seen discreet advertisements placed by transvestites in some of the local newspapers and their calling cards posted in telephone call boxes; but there was no way he was going to publicly publish his telephone number. Mike resigned himself to the fact that he would just have to live with his fantasies and leave it at that.
Brian's first sexual encounter involved his Aunty Betty. Brian used to go around to see his Aunty Betty on the weekends and help her around the house and yard. She gave him a shilling pocket money for his efforts and if he worked late into the afternoon he would stay the night rather than take the long bus ride home after dark. Brian loved his Aunty Betty; she was a widow in her forties, a little plump; but attractive and gregarious. She always wore full makeup, her hair was always styled and she wore nice clothes; twin-sets, suits or tight skirts and blouses. But what Brian liked most of all about his Aunty Betty was that she always wore stockings and high heels. He'd overheard his mother talking to one of her friends saying that Betty dressed like a trollop; but Brian put it down to jealousy.
When Brian stayed over, Betty usually went out for the night and he had often heard stifled giggling and hushed conversations coming from her bedroom in the early hours of the morning when she snuck a boyfriend home for the night. The boyfriend was always gone by the next morning, but Aunty Betty had spoken to Brian about keeping it their little secret and she would give him an extra tanner to keep him quiet.
But sometime she would stay at home and they would watch the telly. TV was pretty boring in those days with only the two BBC channels and one commercial channel broadcasting in black and white. Aunty Betty would pour them both a glass of beer and they would sit in the darkened lounge and watch the telly or she would sit and read the newspaper, but Betty often fell asleep on the couch. Brian liked it when Betty stayed at home with him because she always dressed attractively and she would often give him a very nice leg show, especially if she lay down on the couch after falling asleep.
Brian would pretend to watch TV but he spent most of the time surreptitiously staring at his auntie's legs. Brian's Aunty Betty was a shoe dangler; when she sat on the couch and read the newspaper she kept one foot on the floor and would cross her right leg over her left and rock her foot slowly dislodging her shoe from her heel. As she rocked her foot she let her shoe slowly slide down her instep and swing from her toes. Brian would watch intently as she did this. He admired the sheen of her stockings, and those gorgeous little 'creases' that occurred at the bend of her knee and ankle.
One evening Brian became very bold and decided to try to do a little more that just look at his auntie's legs; he wanted to touch them. Thinking she was engrossed in the newspaper, Brian stretched his legs out in front of him, and interlocked his fingers and placed his hands together over his hardening penis, he tried to rub it surreptitiously so as not to attract his auntie's attention or to appear too blatant. Aunty Betty's dangling shoe had fallen off when she uncrossed her legs and she rubbed her stocking foot up and down her other leg and then she slipped off her other shoe and rubbed her stocking feet together. Brian decided to make his move.
"Would you like me to that?" he asked.
"What's that hun?" Betty replied.
"Rub your feet Auntie; would you like a foot massage?"
"Ok Brian but be careful not to ladder my stockings," she smiled.
Brian shifted over to the couch and put his auntie's feet in his lap. He rubbed the soles of her feet and massaged her cute painted toes through the reinforced toes of her nylons. Auntie Betty relaxed and eventually fell asleep. Brian got bolder now that his auntie was sleeping and lowered his head down and pressed his face into the bottoms of her gossamer encased feet her feet and slid his face up and down them. He was enamoured by the feel of her diaphanous nylons and faint smell of her sweaty feet.
He surreptitiously reached down and opened the buttons of his fly and freed his growing erection. Brian took both her nylon-covered feet in his hands and raised both her feet to his face and inhaled her scent. He sighed with pleasure as he kissed the soles of her feet, one after the other then, throwing caution to the wind, he opened his mouth took his auntie's stockinged foot into it. After sucking on her nyloned toes for a minute or two he could contain himself no more and brought her feet down to his groin.
Brian firmly gripped her smooth ankles and pressed both her feet around his cock. He slowly slipped back and forth between them, enjoying the most exquisite sensations that he had ever felt in his life. He let go of one of his auntie's ankles and ran his hand up and down her stockinged legs, tracing the seams with his fingers and caressing the dark material of the welt, the dark band at the top of her stockings. He could contain himself no longer and climaxed; his semen gushed all over his auntie's moist nylons, soaking the material, causing it to appear much darker than it really was. He clasped the tip of his penis to her toes, watching as his semen dampened the reinforced nylon.
Aunty Betty woke with a start and yanked her feet out of Brian's lap and he realised that he had gone too far.
"Brian! What on earth do you think you're doing!" she scolded.
"Oh I'm so sorry aunty; please don't tell mom. I'm so sorry!" Brian pleaded and ran from the room.
He bolted upstairs to the guest bedroom where he stayed when he slept over and slammed the door closed. Throwing his clothes in heap on the floor he jumped into bed and pulled the covers over his head shaking and crying with humiliation. He was absolutely appalled that he had allowed his stocking fetish to get him in this untenable situation. He didn't know how he was ever going to look his Aunty Betty in the face ever again and he was sure that his mother would disown him.
Brian heard the bedroom door open and the click his Aunty Betty's high heels as she approached the bed. Then he felt the bed sag when she sat down on the edge of bed and the whisper of her nylons as Aunty Betty crossed her legs.
"Brian?" she whispered tentatively.
"Go away!" he cried from under the blankets.
"Brian; I'm sorry sweetie," his Aunty Betty cooed.
"Why are you sorry? You didn't do anything wrong; I did!" he sniffled.
"Well honey I've been watching you watching me and I knew that you had a thing for stockings because your mother told me; so I shouldn't have teased and tempted you," Aunty Betty said.
"You knew?" Brian moaned, "Now I'm even more embarrassed."
"Never mind honey; let me make it up to you just this once and then we'll never talk about it again ok?" she said.
"What do you mean; make it up to me?" Brian asked inquisitively lifting his head outside of the blankets.
"Best I just show you sweetie; I used to do this for you uncle sometimes," his aunt smiled mischievously.
To Brian's amazement his Aunty Betty pulled down the blankets down to his groin and exposed his naked body. She looked at his engorged penis and smiled.
"Lovely," she said; almost to herself.
Then she did something that Brian would never forget for the rest of his life. She took a silk stocking out of her pocket and placed the warm diaphanous garment over Brian's now rampant penis.
"Oh Auntie!" he groaned.
She tentatively took hold of Brian's cock and he closed his eyes in pleasure and tilted his head back.
"Look at it Brian," Aunty Betty whispered.
Then he opened his eyes and watched as her red nailpolished fingers slid along Brian's silken encased member and slowly stroked his cock. She gripped him tighter, pulling his foreskin up over the purple glans, then back down to expose it in the dim light of the reading lamp. Then she moved her hand ever so slightly faster, sliding up and down the skin of Brian's cock. She twirled her hand back and forth over the taught stocking, slightly at first and then in greater degrees, as she slowly masturbated her nephew. Brian's hips moved to an involuntarily in tempo with his auntie's ministrations as Betty tightly stroked his penis.
"Oh Auntie; this so naughty, but it's so lovely," Brian moaned.
"Shhh honey, just enjoy it; it's only ever happening this once," she said.
Brian could feel his orgasm approaching quickly and he become bolder and took his enjoyment one step further. He reached out and grabbed his auntie's nyloned thigh and slid his hands up and down her ultra sheer stockings. Her nylons were smooth and slick above her knees and thighs because of the garters pulling the stocking tops so taunt. He got to her stocking tops, and stroked the dark shiny bands of the welts and then felt across the garter tabs hooked to the nylon and up the length of one of the garter straps. His hand slid off the garter strap and stroked her smooth, soft, bare skin just under her knickers. Then his hand brushed against his auntie's nylon knickers.
Aunty Betty gently eased Brian's hand away from her knickers and placed it back on her stockinged thigh.
"No higher up my leg than there Brian, you naughty boy," she instructed him.
Betty's hand was sliding up and down her nephew's silk stocking encased penis. Brian was in heaven just to be holding and feeling her beautiful stocking legs. He moaned and gasped at the feel of his sensitive glans being caressed by her silk stocking as his auntie rubbed his cock slowly up and down and he stroked her nylon encased legs.
Brian looked down at his stocking sheathed penis and saw that the silk around his glans was soaked with pre-seminal fluid. He felt his orgasm erupt through his body; the most intense orgasm he had ever felt. His whole body shuddered and his penis quivered as Aunty Betty, sensing her nephew's climax, gripped his manhood and rapidly pumped it. A glob of milky white semen extruded through the silk stocking; this quickly became a flood as Brian spurted jet after jet of hot seed, it ran down his silken encased shaft and onto his auntie's fingers. She continued to vigorously stroke his shaft, squeezing and milking him until his orgasm subsided.
Brian lay there gasping, his erection slowly subsiding, the stocking flooded with semen wrinkled around his cock. His Aunty Betty removed the semen splattered stocking from his cock and wiped him clean and then pulled up the covers.
"Ok Brian; you've had your reward for apologising for what you did earlier; but this is the last time this is ever going to happen," Betty said quite sternly.
"We will never talk about this ever again and I think I will no longer need you to stay over on the weekends ok?" she said.
Brian nodded and watched as his auntie stood up, adjusted her skirt, and then clattered out of the room on her high heels.
And they never did. Brian never bought up what had happened that evening and neither did his auntie. They sometimes exchanged knowing glances, especially if Aunty Betty caught Brain looking at a woman's legs, and his mother gave him one of her knowingly quizzical looks when he told her he wouldn't be staying at his auntie's on the weekends any longer; but the incident was never spoken of.
Of course Brian replayed the incident over and over in his head and it was his favourite masturbation fantasy. The incident reinforced his nylons fetish and eventually led him to marrying his wife who wore hosiery every day and dressed very similar to his auntie. His auntie had even given him a knowing smirk as stood at the altar on his wedding day.
But that was all ancient history; he was now a lowly door to door hosiery salesman doing the rounds of the suburbs of Birmingham.
Mike planned to have Tuesday afternoon free from the drudgery of books and accounting and to dress as Michele and have some girly fun. He washed himself and shaved very closely. Then he began to make preparations for the transformation. He took two old laddered and unwearable stockings and filled them with rice doubling and tripling the stockings over on themselves and then tied and cut them off to make himself a pair of false breasts.
He sat down at his dresser and applied lashings of foundation and finishing powder to his pale face and then black eyeliner and mascara and finally blue eyeshadow. He rouged his cheeks and applied another coat of finishing powder. He then carefully painted his lips with bright red lipstick, extending the lip-line to make his lips appear fuller. He smacked his lips together, pursed them, and then bit down on a tissue with his lips to set the lipstick and remove the excess.
Mike lit a Woodbine, poured himself a glass of sherry and then sat down to paint his toe and fingernails with plum red nailpolish; it was then that he made the mental transformation from Mike to Michele. Michele looked at the small collection of wigs that she had knocked off from Oxfam and selected a shoulder-length brunette bob and pulled it on, fussing with it until she had it positioned just right with the fringe level with her eyebrows.
She looked quite attractive for her age she thought as she rummaged through her lingerie and selected a white Jacquard knit, two-way stretch, body-shaping bustiere with lace floral motif; it was high waist fronted, with flat sewn seams with attached suspender straps. She loved the way this garment shaped her body. She decided to wear white satin full-cut knickers with the bustiere. She went to her wardrobe and selected a navy blue double-breasted suit; the pencil skirt had a kick pleat and the jacket was very tight at the waist. Finally she picked out a white silk blouse and black high-heeled courts.
Now for the depressing part as she opened her hosiery drawer. There were only a few laddered and holed pairs of stockings in drawer and one unopened packet of smoke-grey, fifteen denier, fully-fashioned stockings. She lamented her dearth of hosiery; she had all the clothes, cosmetics, lingerie, shoes and wigs that she wanted, but she just couldn't get quality hosiery. She pulled on a pair of fine cotton gloves and opened up her last packet of stockings and laid them out carefully on the bed.
Michele removed the gloves and stepped into the bustiere and struggled to get it over her hips and then her chest. It firmed and flattened her stomach and cinched her waist; the inbuilt brassiere cups pointed straight out from her chest like limp cones until she stuffed her homemade breastforms into them. She pulled on the full-cut satin knickers and a little shiver of pleasure ran through her body as the satin whispered against her skin, snug tight around her buttocks and penis. She looked down at the smoke-grey stockings lying on the bed waiting to be carefully donned and reached for the hosiery gloves and then suddenly changed her mind. They were her last pair of pristine stockings and she wanted to save them. She put on the cotton gloves and carefully put them back in the packaging and put them away.
She rummaged through her hosiery drawer and found her next best pair of stockings; black fully-fashioned with a Cuban heel. One stocking had a fine ladder running from the welt to the ankle and the other had a hole the size of a threepenny bit at the knee; the hole had been prevented from spreading by the judicious application of clear nail varnish. Michele sighed and pulled on the dilapidated stockings carefully fitting them to the garter clips. She pulled off the gloves and smoothed the wrinkles out of her stockings and straightened her seams. Another sliver of delight ran through her as the sensual stockings rubbed against her shaven legs.
She pulled on the pencil skirt, fastening the waist and adjusting the hem so it sat just above her knees. The tight pencil skirt hugged her thighs and restricted her gait when she walked. She buttoned the white silk blouse and tucked it into the skirt and then walked back to the dressing table vanity mirror on stockinged feet. She loved the way her pencil skirt forced her to take foreshortened strides which emphasised her legs and buttocks and the way the skirt was stretched tight around her thighs. She clipped on some silver earrings, a matching necklace and bangles on both wrists. Then she liberally sprayed herself with perfume including a spray under her skirt; she had seen her late wife do this and although there wouldn't be anyone to enjoy her scented thighs, she liked the idea of it.
Michele walked back to the bed and sat down to pull on the black high-heeled court shoes and then put on her jacket and buttoned it. She stood up and walked over to the full-length mirror and inspected herself. Lovely, she thought. She went back to the dresser and made some adjustments to her wig and touched up her makeup and then went down the staircase to the lounge to get another packet of cigarettes and a bottle of wine. She would spend the afternoon and evening smoking and drinking and having solitary fun. When she couldn't stand the stimulation any longer she would surrender and masturbate herself to orgasm. Some days she would do this three or four times during the afternoon and into the evening. Other than her own reflection in the mirror, the only other form of stimulation she had was a few fashion magazines and her imagination.
Michele was rummaging around in the hallstand drawer looking for cigarettes when there was a brief knocking at the door and then it suddenly flew open. Standing there was a man in his forties dressed in a suit and topcoat carrying what appeared to be a sample case. He smiled and stepped over the doorway before Michele could say anything.
"Hello Missus. I'm Brian Macklin and I hope I can be of service," he smiled.
Brian Macklin was nothing if not dedicated when it came to his job. As a top sales executive working for his father-in-law he had made thousands of pounds for the firm by studying sales and marketing trends and ensuring that profits were maximised.
Even though the only job available to him now was as a door to door hosiery salesman he applied the same level of dedication and decided to learn all he could about his products. He knew that sheer nylons fascinated men and women because of their luxuriousness, sensuality and because they greatly improved the appearance of the average English woman's lily-white bare legs, but practical knowledge of hosiery? He had none. So he began his education by visiting a hosiery manufacturer.
First he learned about denier: this is the thickness of one thread of nylon used in making hosiery. The lower the number in denier, the lighter and finer the yarn, and thus the sheerer the stocking. A hair from the average human head is about fifty denier. The lowest denier nylon ever produced for stockings was six denier, which was exhibited at the Nylon fair in London in 1956. Most quality stockings are fifteen denier and below.
Stockings were made with reinforced heel and toes using a 'reticulating heel' machine. This machine actually knits the heel pocket into the stockings using a device that knits the foot first, then the heel pocket and finally the leg and welt; this creates the "V" in the heel. Heels and toes are reinforced in fully-fashioned stockings and this gives the consumer the assurance that sharp nails or rough shoes will not cause the stockings to run. After manufacture each stocking is seamed, one at a time. The hole at the top of the seam; called the 'finishing loop', or 'keyhole back', cannot be eliminated, as the seaming machinist has to finish the seam turning the stocking top, otherwise known as the welt, inside out.
Armed with this knowledge he set forth in the suburbs of Birmingham going door to door with his sample case. His easy smile, good looks and disarming personality soon made him an invaluable asset to the company and he began to make a tidy wage considering the humble nature of his employment. The job had the added advantage that some of the women insisted on trying on the samples to see how they looked on their legs. Most of his customers would retire to the privacy of their bedroom to do this, but some of them would come back out and ask him his opinion of how they looked. One or two of the cheeky ones would notice the bulge in his trousers and tease him a little with a leg show. One particularly mischievous woman who had to be at least sixty but still had magnificent legs actually asked him to straighten her seams. He nearly came in his trousers as he smoothed the luscious nylons up her long legs. She invited him to come back in a month and slipped him a wink as he went out the door. He would definitely be going back there!
But mostly the job was boring and women bought his wares relying on the pictures in the catalogues he carried or simply asked for a particular brand and size that they always wore. The other problem was that constantly making sales meant moving further and further out into the suburbs to find new customers. One Tuesday afternoon he found himself walking down a cul-de-sac called Sovereign Way in the suburb of Moseley. He'd not made a sale all afternoon when he knocked on the door of 162.
There was no answer so he knocked again and waited patiently for a minute or two lighting up a Park Drive and enjoying the taste of the tobacco as he waited on the stoop in the afternoon sun. He was about to leave when he heard the unmistakable sound of high heels clacking on a wooden staircase. Brian looked through the sheer net curtains and was impressed with what he saw. An attractive, well-dressed matron in her forties was just stepping off the last rung of the staircase. She wore a navy blue suit cinched at waist with a tight pencil skirt with a hem that came just above her knees. Her white silk blouse, black high heels, silver accessories and heavy makeup finished the ensemble. Her she wore a shoulder-length brunette bob that caresses her shoulders.
Brian purred to himself; she was a big girl but well proportioned. Then he noticed the flaw in her appearance; one stocking was laddered and the other had a hole near the knee. This breach of style in what was an otherwise elegant ensemble was glaring. Brian smiled; he'd definitely make a good sale here he thought. During his short career as a salesman he had learned that getting through the door was half the battle when it came to door to door salesmanship; haggling with a potential customer through the doorway was tantamount to defeat, but once inside a house a sale was pretty much guaranteed. He watched the woman until she approached the hallstand and began rummaging through the drawer and then applied a technique he had devised over the last few months.
He knocked briefly on the door and turned the doorknob at the same time. The door opened easily and he quickly stepped into the hallway and introduced himself before the woman could say anything.
"Hello Missus. I'm Brian Macklin and I hope I can be of service," he smiled.
Michele was shocked! She quickly realised a number of facts simultaneously: the man was a complete stranger, the man didn't realise she was a transvestite, the man was some sort of door to door salesman and the man was quite handsome. She took a deep breath and spoke.
"What do you want?" Michele murmured in her husky feminine voice, hoping that she didn't sound at all masculine.
"I can help you Missus; I can see you have need of my wares," Brian beamed his winning smile.
The woman had a deep smoky voice and was large but well proportioned, Brian thought to himself. He wouldn't mind getting to know her a little better; she was just his type.
"I sell stockings Missus, and if you don't mind me saying so, it looks like you could use some good quality hosiery," Brian nodded down at Michele's laddered nylons.
Michele was very nervous, on one hand she was flattered that this salesman mistook her for a real woman, but on the other, she was scared that he would soon she through her ruse. She desperately needed stockings though, and this could be the opportunity she had been hoping for. Besides, the salesman was quite a dish, she thought.
Brian boldly stepped further inside the house and made his way to the lounge and began to open his sample case. Michele closed the door and followed him into the lounge.
"I suppose I could use some new hosiery," she said.
Brian sat on the couch and mooched around in his sample case which he had placed on the coffee table. He produced a catalogue and patted the vacant space on the couch beside him. Michele nervously sat down beside him. This is the closest she had ever been to another person and she was worried that close up he might see through her disguise. Then she decided 'what the hell!' she was in her own home and she would do as she pleased; if the salesman was putt off by her, he could leave any time it suited him!
"Here Missus; have a look through this and see if you see anything you like," Brian smiled at Michele and handed her the catalogue.
Michele's painted fingernail brushed against Bran's fingers as she took the catalogue from him and a little spark of electricity flew between them. Their eyes locked briefly and then Michele opened the book and began to flick though the pages as Brian nervously cleared his throat and then began to rummage in through his sample case, very aware of the proximity of the sexy woman sitting beside him. Her perfume was delightful and he stole a glance down at her legs to see that her skirt had ridden up considerably when she had sat down and the beginning of her stocking welts was just visible.
Brian felt himself hardening and lifted the sample case onto his lap to cover his growing erection. Michele was also aware of the presence of the man sitting beside her and she could smell a faint whiff of aftershave and tobacco. She smiled inwardly as she saw him sneak a peek at her legs and she adjusted the hem of her skirt to cover her stocking welts. She was becoming quite aroused by the proximity of the salesman and she enjoyed the little mind games they were playing with each other. When he reached for the sample case she was shocked but delighted to see that he had an erection. Her own penis hardened slightly in her satin knickers.
"Size twelve or a D?" Brian asked, clearing his throat again nervously.
"I'm pretty sure; yes," Michele answered.
"You've never been properly sized then?" Brian replied; surprised that this elegantly dressed woman was unsure of her hosiery size.
Brain looked down at Michele's legs and feet and noticed that she had big feet but that her legs were quite shapely and the black high-heeled court shoes she wore looked very nice on her. Her laddered stockings still had a nice sheen to them and he had to force himself to pull his eyes away from her legs and look her in the eye. She was heavily made up and her red lipsticked lips, mascaraed and shadowed eyes were particularly to his taste. He found himself becoming attracted to this generously proportioned, smoky voiced woman.
"No I've never been professionally sized," Michele smiled at the salesman.
She was openly flirting with him now and crossed one leg over the other and swung her foot seductively. Brian felt his erection throb in his underwear as his eyes locked on the legshow that this woman was putting on for him. Was she coming on to him?
Michele grew bolder as she gained confidence.
"Maybe you can size me?" she said seductively.
"My pleasure," Brian eagerly replied.
He rummaged around in his sample case and produced a pair of fine cotton hosiery gloves and put them on and then selected a pair of black, fifteen denier, fully-fashioned, Cuban heeled stockings.
"Shall we try these?" Brian held up one of the diaphanous nylons for Michele to see.
"Let's," Michele responded with a throaty growl.
Brian put the sample case back on the table and stood up, openly displaying the growing erection outlined by the material of his trousers. He was about to intimately touch this woman's feet and legs so she might as well be under no illusion of the effect that she was having on him. If she didn't like what she saw; now was the time her to tell him to get out of her house.
Michele looked at the bulge in the salesman's trousers and then looked him directly in the eyes and gave him a little smile. She knew that she was treading on dangerous ground here; but she was overcome by her feelings of sensuality and was seduced by the raw sexual power that she had over this stranger.
Brian knelt at Michele's feet and gently took one her feet in his hands and removed her shoes. The aroma of her nyloned feet mingled with her perfume and his cock spasmed. He ran his hands up her leg until he came to the hem of her skirt and then he looked quizzically at Michele for permission to proceed. She nodded back at him, her smile evident of her consent.
Brian's hands were shaking as he gently eased the hem of her skirt up her thighs and exposed the garter straps; he was unable to take his eyes off her nylon encased legs that were just inches from him.
Michele lowered her hands to her thighs and began to let her fingers fiddle with one of her garter tabs where the stocking was fastened; playing with the small rubber tab covered in sheer nylon between her fingers, lightly pulling and tugging on it. Letting her fingers go from the garter tab and run across her slick stocking welt in a smoothing motion; her red fingernails contrasting with the smooth dark nylon.
"Let me help you," Brian whispered breathlessly.
Brian unclasped the garter tabs and eased the laddered stocking down Michele's legs delighting in the feel of the nylon on her warm milky white legs. Michele shuddered and a small groan escaped her lips. There was now no pretence of what was happening between them and Brian unclipped the stocking on her other leg and slid it down to her ankle and then pulled the sheer garment over her painted toes.
"Now let's see if these fit shall we?" Brian smiled up at Michele from where he knelt on the carpet before her.
He opened the top of one stocking with his gloved hands and Michele pointed her painted toes and allowed him to ease it over her foot and then to gently smooth the stocking up her calf and thigh until the welt was snug and tight at the top of her thigh, an inch below her knickers. She shuddered with pleasure as the salesman smoothed silken garment along her leg.
"Let me adjust these tabs Missus; these stockings are longer than the ones I took off you," Brian said.
"Of course," Michele whispered her compliance.
Brian fidgeted with garter tabs until he had shortened all four of them and then he carefully snapped them back in place. He then adjusted the garter straps on her other leg and was rewarded with a glimpse of white satin knicker. He wondered briefly if she was married and what would happen if her husband came home and found him kneeling before her with her skirt hiked up and a strange man lipping on her stockings. The thought quickly went away as he slid the other stocking up her leg and fastened it in place. He took hold of Michele's high heels and gently placed them on her feet.
"There; now stand up so I can straighten you seams," Brian said, removing his hosiery gloves.
Both he and Michele were aware that he should leave the gloves on so that he wouldn't snag or ladder her nylons but they also both knew why he had discarded them. He wanted to feel Michele's stocking encased legs with his bare fingers and revel in the sensations of the gossamer nylons on her flesh. Michele stood up in front of Brian and the hem of her skirt fell to her knees causing a gust of perfume to invade Brian's nostrils. Stood in front of his kneeling form; her legs slightly apart.
Brian slid his hands up each of Michele's legs straightening the seams of her stockings. His cock was rock hard in his trousers as he delighted in the feel of the translucent stockings. Michele was visibly shaking with pleasure as the salesman massaged her nylon encased legs as he straightened her seams. Little shocks of pleasure ran up her legs and her penis twinged, uncomfortably trapped in her tight knickers.
"There; all done Missus," Brian sighed with satisfaction.
Michele sat back down on the couch; her skirt riding up again. Brain swallowed hard and extended a shaking hand and took hold of Michele's stocking foot and patent leather pump. Michele placed her stocking encased foot in Brian's lap and watched him begin to squirm and moan. She was enthralled in the power she was exerting over this salesman who had such an obvious fetish for his own wares.
"Oh my!" Brian moaned.
Michele's dark reinforced nylon toes now rubbed against the salesman's hard penis clearly contoured by the material of his trousers. Brain was losing control now and he removed Michele's shoe and began rubbing Michele's other nylon encased foot all over his face. Michele heard his muffled moans.
"Oh my god, I can't believe this is happening! Your foot smells and feels
so good!" Brian sighed
Michele pressed and rubbed her stockinged foot against his erection while Brian worshiped the other foot pressed firmly over his nose and mouth; inhaling her foot odour and licking at her nylon imprisoned toes. Brian stroked his hand over the stocking foot that was pressing on his hard cock. He continued to moan; licking and sucking on Michele's reinforced stocking covered toes, sliding his other hand farther up and down Michele's sleek nyloned leg.
"Take it out," Michele whispered seductively.
Brian fumbled at his lap and unbuttoned his fly and released his engorged penis. Michele worked her stocking foot all around his erect bare cock. Michele focussed on the under side of his shaft, just below his glans. After few strokes from Michele's gauzy reinforced nylon toe, Brian was squirming and groaning. A clear filament of pre-seminal fluid oozed from the tip of Brian's penis stuck to Michele's toes and wet her nylon. Brian ran his hand up and down the full length of Michele's stocking sheathed leg from the tips of her toes to the tops of her hose. Brian moaned with pleasure at the feel of Michele's nylon rubbing against his phallus.
Michele pulled her other foot away from Brian's face and dropped it into his lap. She placed each of her feet together and arched her soles, trapping Brian's engorged manhood between them. She moved her feet back and forth masturbating Brian's cock with her nylon sheathed feet.
Brian's cock was swollen, the glans bright red and almost ready to shoot its load onto Michele's foot. Pre-seminal fluid was flowing freely from the eye of his penis, and the sensation of the wet scratchy-slick nylon sliding up and down his shaft was exquisite. Michele's stockings became soaked with Brian's pre-seminal fluid.
Brian looked down at his lap again and watched as Michele's large but shapely feet slid wetly up and down his straining penis, milking him with her diaphanous encased appendages. The nylon over her toes glistened with pre-seminal fluid and Brian ran his hands up and down Michele's stockinged legs all the way up her thighs to the welt and garter straps. He bucked back and forth fucking Michele's feet and he could sense his orgasm approaching.
Suddenly a giant dollop of sperm erupted from Brain's cock and splashed against Michele's leg, soaking into her stocking and darkening the nylon. Michele gasped but she managed to put a toe over the glans of Brian's penis so that she could massage some of the subsequent spurts into his penis. Brian's cock began to spasm and shoot rope after rope of his hot cum all over her black nylons, leaving the soles of her feet dripping with pearly white puddles of semen. Brain, breathing hard, was wide-eyed as he watched Michele milk his cock with her heavily sperm coated nylon foot.
Michele was experiencing intense feelings of pleasure as she miked Brian with her feet and his hands madly stroked and fondled her stockinged legs. When he orgasmed he gripped her thighs and dug his fingers into the white sensitive skin above her stocking welt and she could feel her panties becoming wet with her own pre-seminal juices. Brian hooked a finger into the keyhole back of her stocking welt and pulled at the nylon tight around her thigh as he gasped and spluttered in the throes of orgasm.
Slowly Brian came down from the high of his climax and he released the tight grip on Michele's thighs. He unhooked one of her stockings and rolled it down her leg, slipping the wispy garment off her foot. He dabbed at the cooling semen on her other foot and then wiped himself dry and pushed his deflating penis back into his flies.
Michele sat demurely on the couch letting Brain clean her feet and legs with the stocking.
"Let me go and get a damp cloth from the kitchen Missus and then I'll clean your feet for you. After that I'll fit you into another pair of nice stockings ok?" Brian said getting to his feet.
"Lovely," Michele replied.
"Help yourself to whatever you want from my sample case in the meantime," Brian said as he strode out of the room.
Michele poked around in the salesman's sample case and selected six pairs of good quality nylon stockings in her size. She placed the treasured items on the lounge beside her as Brain returned with a warm damp cloth with which he cleaned her toes, feet and legs. He then donned the hosiery gloves and unwrapped a package of brown seamless stockings, he carefully rolled them and slipped them up Michele's legs, clipping them to the garters and smoothing them up her legs to remove the wrinkles. Then he slipped her shoes back on her feet.
Brian stood up and closed his sample case and Michele rose from the couch and walked with him down the hallway towards the front door. As he reached for the doorknob Michele put her had on the door and stopped him.
"What? No kiss goodbye?" She teased.
Brain took her in arms and kissed her passionately, squeezing her buttocks and crushing her lips with his whilst slipping his tongue deep into her mouth. Michele pressed against him and felt him begin to stiffen again through the layers of their clothing; his cock hard against her leg. He pushed her gently away and breathed deeply.
"I've got to go Missus; but I would to drop around again," Brian smiled.
"Next Tuesday then?" Michele smiled back.
"You bet; maybe we can spend a little more time getting to know each other better," Brian winked at her cheekily.
"Maybe," Michele smiled back and opened the door and gently manoeuvred him out the door.
"Anyway, like I said you can call me Brian," he said with a grin.
"And you can call me Michele," she smiled.
Michele closed the door and wondered to herself how she was going to break the news to Brian that she was a transvestite.
Michele thought about her first sexual encounter with the door to door stocking salesman; she had certainly enjoyed giving him a footjob and she would like to explore their burgeoning relationship further. She particularly liked it when he had kissed and cuddled her just before he left. Of course the dilemma was how to explain to him that she was a transvestite.
So far nothing more than masturbation had occurred between them, but Michele was fantasising about going a lot further than that. But this was the nineteen fifties and people were not tolerant of any form of sex other than that which occurred between a man and a women; the word gay meant happy not homo. Not that Mike felt like a homo; when he was dressed as Michele he imagined himself as a totally feminine woman. Now; if only Brain felt the same way!
Michele was mulling over a number of options; one: do nothing but refuse to see Brian again, two: tell Brian the truth and hope that he isn't disgusted that she is a transvestite, or three: don't tell Brian that she is a transvestite but continue to have sex with him. She had a week to decide, and she chose not to rush her decision. As the days passed her fantasies became more vivid and she used the memory of the nylon footjob she had given Brian as her main masturbatory aid.
On Friday Mike received a phone call requesting that he come to the head office of the Midlands Lingerie and Fashion Garment Distribution Company located in Birmingham. The company had heard that he was good accountant and bookkeeper who charged a reasonable rate and they had an employment opportunity for him. Mike caught the bus to the head office and arrived on time at 10:00am. He had an interview with the firm's senior accountant, Mr Tilsbury who conveyed that the firm was looking to outsource some of their bookkeeping, particularly the accounts of their travelling salesmen. They had just become the local distributor of Aristoc hosiery and expected to increase their sales significantly as Aristoc was the most popular hosiery brand in the UK.
"We need more accountants and bookkeepers because we are expanding," Mr Tilsbury said.
"We sell quality lingerie and hosiery and we've just acquired the Aristoc distribution rights for the whole of the Midlands," he further explained.
Mr Tilsbury took Mike on quick tour of the offices and warehouse. At the front of the warehouse was a large counter over which the salesman collected their stock and completed paperwork with the stores assistants; behind the counter the warehouse was fitted with floor to ceiling shelving loaded with stock. Leaning nonchalantly on the counter was a handsome man in his mid forties who was giving a plump, mature, female stores assistants his biggest, cheekiest grin. She was halfway up a ladder reaching for some stock and the salesman was getting an eyeful of her legs and knickers. She was obviously well aware that he could see up her skirt but she seemed to enjoy flirting with him.
"We distribute to all of the major retailers in the Midlands and we also have about twenty or so salesmen working door to door." Mr Tilsbury was saying as they approached the counter.
"Actually there's one of them over there; come on over and I'll introduce you."
Mike was somewhat taken aback, he recognised Brain immediately; he actually felt a twinge of jealousy when he saw him looking up the skirt and flirting with the saleswoman.
"That fucking Brian; he spends more time looking at stockings than he does selling the bastards!" the senior accountant said.
"But I'll give him his due; he's our best salesman."
"Come on over and I'll introduce you," he said, leading Mike over to the counter.
"Mike this is Brian, one of best door to door salesmen," the senior accountant introduced them.
Brian snatched his eyes away from the saleswoman's skirt and looked guiltily at them. He then smiled that magnificent smile and held out his hand.
"Hello Mike; I'm Brian; don't believe a word this bastard tells you about me," he grinned.
"Pleased to meet you," Mike answered meekly.
Brian looked at Mike quizzically and asked.
"Have we met before; you seem familiar?"
Mike's face went a deep shade of red, he remembered Brian shooting his load over his stockinged feet and kissing and cuddling him only a couple of days ago.
"No I don't think so; but you can never tell; it's a small world," Mike answered.
"Mike will be doing your books Brian, so it's best to stay on his good side," the senior accountant joked and then led Mike away to continue the tour.
Mike realised that when he was introduced to Brian he immediately adopted Michele's personality in his head. That explained his jealousy and why his thoughts turned to memories their sexual encounter. Mike decided then and there that Michele would be waiting for Mike the next time he knocked on her door and that she would be taking their relationship one step further.
Brian went home from Michele's house very satisfied. He couldn't believe that he could find a mature attractive woman who shared his nylons fetish. Sure, there was something a little odd about her; she was big, but well proportioned, and she had that deep throaty voice; but she was very sexy. He fantasised about her all week and every evening as he lay in his bed with a silk stocking on his cock, masturbating like crazy, he thought of the beautiful silken tunnel that she had made with her feet for him to fuck. He was really looking forward to next Tuesday.
Brian went to the warehouse every Friday morning to restock his sample case and to deliver postal orders. He liked going to the warehouse because there was a cheeky stores assistant there named Alice who liked to tease him. She would find an excuse to bend over or climb a ladder so that he could look up her skirt. Alice was married and he knew it was just flirting around but it stimulated them both and it was harmless enough in the long run.
Today she was halfway up a ladder giving him a great legshow when they were interrupted by the firm's senior accountant and a new bookkeeper who, it was explained, would be working from home. There was something about the bookkeeper that Brian just couldn't put his finger on; he knew him from somewhere but was buggered if he remembered where. When they moved on and left him alone with Alice she resumed her legshow whilst she was perched up the ladder.
She finally came down from the ladder with a box of assorted nylon stockings for him to add to his sample case.
"We've just got the distribution rights for Aristoc here in Birmingham so I'm going to refill your sample case," Alice said.
"Head office wants us to push the product; and to be honest, they're probably the best stockings on the market now anyway."
"I wear them exclusively; look," she said lifting the hem of her skirt to show him her sheer nylon stockings.
"Lovely Alice; I'll bet your husband likes that you wear them too," Brian winked at her mischievously.
"You never mind what my husband likes," she quipped back.
"I always say 'a little of what you fancy does you good' and I make sure he gets a 'little' every now and again."
They both had a good laugh; stopping when they heard the approaching footsteps of the warehouse manager.
"Go on you cheeky bugger; I've filled in the counter book. By the way you were down six pairs of nylons last Friday with no payment recoded." Alice said.
"Shit!" Brian exclaimed, remembering the stockings that he had let Michele take from his sample case free of charge.
"How much am I down luv?" he asked.
"Two pounds, seven and six," Alice replied.
"Do you want me to put it on this week's slate or do you want to pay it off now?"
Brian handed over two pounds and some silver and waited for Alice to make change. A couple of pounds was well worth it for what he had received in return, he smiled to himself.
Brian was looking forward to Tuesday; he would come here to the warehouse to stock up his sample case, make his usual rounds in the morning and then arrive at 162 Sovereign Way in the early afternoon. He wanted to see if the sexy lady who lived there was willing to go a little further. He fantasised about how she had let him fuck her stockinged feet; would she let him do other things to her? Was she married? Did she live alone? Would she even be home when he called? All good questions.
Tuesday morning arrived and Brian had filled his sample case and was ready for the road. He was disappointed that he didn't get a legshow from the plump but pretty stores-assistant. The foreman was at the counter in serious mood and had no intentions of allowing his staff to flirt with the salesmen. As Brian was about to leave, the foreman called him over.
"Brian, Mr Tilsbury wants to see before you go out on your rounds," he said.
"What the fuck does that old codger want?" Brian asked.
"Well as been as I'm in charge the warehouse, and he's in charge of accounts; and as I'm a hard working, callused handed labourer and he's an inky fingered, shiny pants bureaucrat; it's highly un-fucking likely that he would tell me is it?" The foreman answered.
"Fucking wanker," Brian muttered under his breath and headed over to the accounting section.
There was a mature secretary over in the accounting section who insisted on wearing skirts that were far too short for her matronly figure and she often sat far enough away from the edge of her desk for Brian to get an ogle at her fleshy thighs and sometimes even a glimpse of knicker or suspender. When he arrived in the accounts office she was out from behind her desk and bent over at the waist getting a file from the bottom drawer of a filing cabinet. He stood there silently watching her and his erection tented his trousers at the sight of her apple shaped arse stretching her skirt to seam-breaking point, her seamless nylon stockings stretched taut on her shapely legs, they shimmered in the glare of the overhead lights.
She caught him staring and gave him a severe frown and then stared pointedly at his bulging erection.
"You should be ashamed of yourself; I'm old enough to be your mum," she chastised him.
But when she moved back to her desk and sat down she slipped him a wink and made no attempt to pull down the hem of her skirt as it rode up high on her thighs.
"Mr Tilsbury will see you now," she smiled at him.
"You might want to adjust yourself before you go in though," she pointed her chin at Brian's erection and smiled sarcastically.
Brian put his hand in his pocket and adjusted his semi-hard cock so that it was hidden in the pleats of his trousers. He smiled at the secretary.
"If I was a few years older..."
"If you were a few years older, you wouldn't be getting the free show I gave you today luv," she smiled back.
Satisfied that he had held his own bantering with the secretary, Brian knocked on Mr Tilsbury's door and went right in. Tilsbury was pouring over a ledger; another pile of ledgers was stacked on the corner of his desk. Brian didn't know how these desk-bound scribblers could stand their work; cooped up in a dingy office eight hours a day. 'Maybe Mr Tilsbury occasionally got his secretary to come in help take down some particulars?' he smiled to himself but doubted that Tilsbury had it in him. He looked at the photo set on the desk; a mousy little wife and two mousy little daughters. Still you never knew; often in was the quiet ones...
"The warehouse foreman said you wanted to see me Mr Tilsbury," Brian said.
"Oh yes, Brian Macklin; you service the Moseley area don't you?" Tilsbury asked.
"Yes it's on my route," Brian answered.
For a fleeting second he wondered if either the woman who'd given him the footjob last Tuesday or the mischievous older woman who'd asked him to straighten her seams had lodged a complaint.
"Oh good Mr Macklin; would you be so kind as to deliver this ledger to Michael Rodgers, you met him on Friday; he's the new bookkeeper. He lives in Moseley which is on your route today, yes? " Tilsbury finished.
'As if I give a fuck, ' Brian thought to himself, 'now I'm being used as an errand boy. Me! One of their best salesmen!'
"Absolutely, Mr Tilsbury; it will be my pleasure," Brian lied, and picked up the ledger wrapped in brown paper.
Brian put the ledger in his sample case and left the office mumbling to himself.
"Officious little prick!"
"Oh it didn't look that way to me when I saw it," the secretary smiled lasciviously at him.
"Not me; him!" Brian smiled back.
"Well let me tell you something, 'mister hunky smiling salesman'; Mr Tilsbury may be officious, but he ain't little," she smirked and winked at him again.
Brian looked at her with amazement. She got up from behind her desk and bent over to the filing cabinet making a show of returning a file back to the bottom drawer. Brian's eyes locked on her buttocks and legs when she bent over.
"You can stand there all day looking luv; but it'll cost you more than a pork pie and pint of bitter if you want to get your hands on these goods. Call me Friday afternoon and I might let you take me out," she said, turning her head to look at Brian, remaining bent over the drawer.
"I just might," he said, thinking about how cheeky all of the women that worked at this firm seemed to be.
"Then if you treat me nice I might take YOU out; if you know what I mean" she winked lecherously.
Brian sat on the bus heading out of Birmingham City to Moseley. He was thinking about Alice up the ladder in the warehouse letting him look up her skirt, Mr Tilsbury's secretary bent over the drawer of her filing cabinet showing him her ample bottom and shapely nyloned legs, the old lady who'd let him straighten her stocking seams, and of course, about Michele who had let him fuck her stocking encased feet. His cock was so hard that it was almost painful; he hoped that Michele would be home this afternoon and was up for some more fun.
He put his sample case on his knees to hide his erection and he opened it up, attempting to get his mind off sex and back on work. He picked up the brown-paper-wrapped ledger book and looked at the address on the white packing label: Mr Michael Rodgers, 162 Sovereign Way, Moseley.
Fuck! It was addressed to Michele's old man! Jesus! So she was married! But hang on minute; Mr Tilsbury said that Mr Rodgers worked from home. Jesus fucking Christ! The silly tart had given him a footjob and kiss and cuddle session knowing full well that her old man might come home at any time. But hang on? She didn't seem particularly stupid; maybe her old man might have a permanent commitment on Tuesday afternoons. Maybe he was a member of a club, a lawn bowler, a golfer, a bridge aficionado. Who the fuck cared! He would go around to 162 Sovereign Way this afternoon and be a professional salesman. And if Mr Rodgers wasn't home; he might give Mrs Michele Rodgers a good rogering, he laughed to himself.
Monday morning Mike turned up at Oxfam to assist with the donated clothing at the sorting tables. He was very excited, thinking about his meeting with the door to door salesman tomorrow. He was a little perturbed that they had met face to face last Friday at the Midlands Lingerie and Fashion Garment Distribution Company and that Brian thought they might have met before. He was still ruminating about what to do about telling Brian that he, Michele, was a transvestite.
He transformed into Michele in his subconscious. She was ninety nine percent sure that she was going to keep her transvestism a secret from Brian. There were plenty of sexy things that they could do together without Brian having to know any different. She would use Brian's stocking fetish to her advantage and allow him to play with her legs and let him kiss and cuddle her, but she would remain fully dressed and would not allow him to touch the front of her body intimately between her neck and thighs. Besides the thought of anything more than masturbating him and kissing and cuddling was quite abhorrent; after all she was not a homo; was she?
Mike looked around the sorting room and was disappointed to she that Miss McGuire and Mr Billson had volunteered to work today. Miss McGuire was a spinster in her fifties who thought she was the queen of the sorting room and tried to tell the other sorters what to do. On the rare occasion that they were rostered on the same day she barely tolerated Mike working at the ladies clothing sorting tables.
Mr Billson was a pensioner in his late forties who for some reason had a dislike for Mike; they seldom worked together as Mike insisted on working only at the ladies clothing sorting table; Mike's justification for working at the ladies tables was that there was usually more women's clothing than men's clothing donated to Oxfam. Mr Billson sometimes made the odd quip about Mike's penchant for working at the ladies clothing sorting table but Mike ignored them.
Yesterday's sorters had separated the ladies clothing from the men's and the pile of ladies clothing was at least twice as big as the women's. They had just sorted the clothing by gender and removed any torn, damaged or excessively stained clothing. Mike would have no problem justifying working at the women's clothing tables today.
After perfunctory hellos to Mr Billson and Miss McGuire, Mike grabbed a pile of clothed from the pile and dropped them on his sorting table. At the end of the table were bags marked for the various items of clothing: skirts and dresses; blouses and shirts; shoes and boots; hats, gloves and accessories; coats and blazers; lingerie and underwear; and miscellaneous. There was also a large bag marked 'rags' for clothing that was not suitable for resale. Any underwear and lingerie that was not in immaculate condition was thrown in the rag bag as a matter of course.
Mike went to work sorting through the pile of clothing on his table dreaming about his assignation with the door to door stocking salesman tomorrow. He mechanically sorted through the clothing until something special caught his eye. It was a black satin and lace, open-bottom, bustiere with inbuilt waist-cincher and it looked like it would fit him perfectly. It laced up at the back and had four garters on each side of the bodice. The bodice was beautifully detailed black satin with whalebone supports and lace trimming on the top of the brassiere cups and the bottom of the bodice. It would cost a fortune in a West End lingerie shop. Mike held the garment up to inspect it under the overhead lights.
"Oh that's lovely Luv," Miss McGuire cooed, "I'll have that!"
"I don't think so!" Mike snapped.
"Well; why would you want it?" Miss McGuire barked back.
"He's a noncer that's why. I see him nicking women's clothes all the time; it's unnatural it is!" Mr Billson joined the argument.
"It's none of your business! We're not supposed to be nicking anything!" Mike whined at both of them.
"Besides, what I do with the clothing I get from here is none of your business!" he whined.
"Well I never; if I new you was a knicker nicker I wouldn't have had anything to with you! I've seen you nicking women's clothing too; but I thought it was for your mum or a girlfriend." Miss McGuire said.
"Leave me alone! The clothes ARE for my girlfriend," Mike whined at the two of them and went back to sorting the clothing on his table.
"Noncer," Mr Billson whispered under his breath but went back to work.
Miss McGuire was obviously miffed that she couldn't steal the bustiere for herself but she let it go. Mr Billson continued to glance up accusingly at Mike but let the issue drop. Half an hour later one of the other volunteers came into the sorting room with a large pot of tea and a plate of biscuits. Work stopped as tea was poured and biscuits dunked. Miss McGuire wandered off to the loo and Mr Billson looked around and noting that the room was empty, took the opportunity to sidle up to Mike. He muttered softly to Mike.
"You know, I don't really mind what you do with the clothes you get ere' you know. Before the war I lived in London and used to go to some special interest clubs, if you know what I mean," he winked at Mike.
"I have no idea what you mean!" Mike snapped back.
"Yeah, ya do; you're blushing like a virgin on her wedding night," Mr Billson chuckled.
"That's ok though; I just got to thinking, and I could see how a bloke you; dressed properly and with a wig and makeup, could carry it off."
"I have no idea what you're talking about you silly man!" Mike snapped back.
"Sure; well if you ever want to get together over a pint, or something; just remember I'm ok with that sort of thing," Mr Billson winked at Mike again and wondered back to the tea trolley.
Mike was astounded. He might have guessed that some of the volunteers had noticed him knocking off the odd garment here and there but he never dreamt that any of them would confront him. It served him right really, he was too absorbed in the reverie of what he was going to get up to tomorrow. He would normally never hold up a garment for appraisal like he did today; the bustiere would normally surreptitiously disappear off the table and end up in his satchel to be thoroughly inspected in the privacy of his home.
Mrs McGuire returned from the loo and they got back to work. The altercation over the bustiere was not mentioned again, and at knock off time they packed up the tables for the day and got ready to leave. As Mike walked out of the Oxfam and started heading down to the bus stop, he was approached by Mr Billson again.
"Look Mike if I'm wrong about my presumption, well, I'm sorry; but I don't think I am," he said.
"And I meant what I said; I'm ok with that sort of thing and would be willing to talk with you more about it," he said, winked at Mike, and walked away.
Mike was puzzled by exactly what Mr Billson meant. Was he crossdresser too? Was he a man who liked to consort with crossdressers? Mike would have to give this situation some careful thought. He caught the bus and sat down and looked at his watch and had a horrible feeling that he had forgotten to do something important. What had totally slipped Mike's mind was that he was supposed to go to the accounting section of the Midlands Lingerie and Fashion Garment Distribution Company and pick up last weeks sales ledgers.
Mike had a profitable morning and had made some good sales; he was looking forward to some serious fun with Mrs Rodgers this afternoon. He sat in the Moseley Arms public house with the ledger book addressed to Michael Rodgers in front of him, sipping a pint and eating a cheese sandwich and pondered the conundrum regarding Mr and Mrs Rodgers and the house at 162 Sovereign Way. It just didn't make sense that Michele Rodgers would let him fuck her feet and then arrange a meeting for the same time next week if it was at all likely that Mr Rodgers would return home during the afternoon.
He thought back to his meeting with Mike Rodgers at the garment distribution company last Friday. He recalled their conversation:
"Have we met before; you seem familiar?" Brain had asked and Mike had answered, "No I don't think so; but you can never tell; it's a small world."
Something didn't sit right! Mike had blushed and stammered when they were introduced. Did Mike know him? Did Mike know that Brian had been at his house last Tuesday? Did Mike know that Brian had foot-fucked his wife? What the fuck was going on at 162 Sovereign Way? He played it over in his mind.
Suddenly Mike choked and spat out a mouthful of cheese sandwich and bitter ale.
"Fucking hell!!!" he exclaimed.
The punters in the pub looked at him disapprovingly and the publican gave him a stern stare. Mike raised his hands in apology to the lunchtime crowd and went back to his rumination.
Chris; that was it!!! Michele Rodgers was big, but well proportioned, and she had that deep throaty voice. When he compared the images in head of Michael and Michele Rodgers they looked too much alike for coincidence. They were either brother and sister, or, Michael Rodgers was also Michele Rodgers.
"Fucking hell!!!" he exclaimed again and immediately apologised to the patrons and the publican.
Michele Rodgers was a transvestite! Brian Macklin had been given a footjob by and kissed a man! He pondered that for a few minutes and was surprised that he wasn't disgusted with himself. It wasn't as though he'd been with some bloke in suit and tie; he was no homo. He'd been with a sexy woman who just happened to have male genitalia! He rationalised this further. He had a raging stocking and lingerie fetish and had tried on the garments himself occasionally. Brian didn't have the urge to dress up like a woman, but he had to admit that Michele looked sexy hell.
So what to do now? That was the question!
He had a number of options open to him. He could continue on as if he knew nothing; he could confront Michele with the truth; he could just never go back to the house at 162 Sovereign Way; or he could even blackmail Michael Rodgers and threaten him with exposure. It was quite a conundrum. Bugger it! He would keep his appointment with Michele this afternoon and see how it played out. He felt himself begin to thicken down there in anticipation.
Brian finished his pint. Left the pub, after again apologising to the publican for his outburst, and caught the bus that would take him to Sovereign Way. He plotted and schemed and played out various scenarios in his head but he had to admit that the more he thought about the situation the more he became aroused. He'd never given any great thought about what it might be like to have sex with a transvestite; he'd always had plenty of willing women. But he had to admit that Michele was not only sexy, the way she dressed and spoke, she had also demonstrated a particular aptitude when it came to satisfying his fetish.
Brian stopped briefly at a chemist and by the time he knocked on the door of 162 Sovereign Way he was sporting a fierce erection and had formulated a strategy regarding how he was going to deal with Michele Rodgers.
Tuesday morning and Mike had a nagging feeling that he had forgotten something important. Then it dawned on him. Fuck!!! He was supposed to go into the Midlands Lingerie and Fashion Garment Distribution Company yesterday and pick up the sales ledgers. He looked at his watch. Shit!!! Ten o'clock; there was no way he could make it into Birmingham and get home again before his afternoon sware. He decided he would keep his tryst with the salesman and then call Mr Tilsbury later in the afternoon to apologise. If he rang now, Tilsbury was likely to demand that Mike come to the firm and collect the ledger and Mike was anticipating transforming into Michele and having a pleasant afternoon with Brian Macklin. Mike allowed his mind to transform from his male persona to Michele as he prepared for the encounter.
Michele poured herself a bath and shed her male attire and then lowered herself into the hot frothy water. She closely shaved her face using a hand held shaving mirror and a new razorblade. She ran her hands all over her chest, arms, legs and buttocks and shaved away any stubble she found.
She dried herself off and sat at the dresser and applied foundation, finishing powder, blush and lashings of mascara, eyeliner and eyeshadow. She painted her lips with two coats of ruby red lipstick. She pulled on her favourite brunette, shoulder length, wig and adjusted it so that the fringe came to her eyebrows. She stepped into a pair of red satin full-cut panties and pulled them tight around her buttocks and tucked her penis under the gusset. Then she stepped into the black satin and lace, open-bottom, bustiere and laced up at the back with some difficulty. The bustiere cinched her waist and gave her an hourglass figure, accentuating her full hips. She slipped her homemade breastforms into the cups and admired herself in mirror.
Michele opened a package of seamless, flesh-toned, fifteen denier stockings and rolled them up her legs attaching them to the four garters on each side of the bodice of her waist cincher. She had selected a charcoal grey business suit with a knee length pencil skirt with rear kick pleat and a white silk long sleeved blouse. She liked the idea of wearing the risqué bustiere under the conservative suit. She stepped into black, four-inch high heel pumps and accessorised herself with gold earrings, necklace and bangles. She fastened a gold chain anklet around her left ankle.
She sprayed a liberal amount of perfume on her décolletage and under her skirt and picked up her bottle of red nail polish and went downstairs to the lounge. She poured herself a glass of red wine and lit a Woodbine and glanced at the mantle clock. She had half an hour to do her nails before Brian was due to call; providing he was on time of course. Almost exactly thirty minutes later there was a knock on the door. Michele pulled a curtain to one side and peeked out. Brian Macklin, the door to door stocking salesman, stood on her doorstep.
Brian was very impressed with what greeted him at the door of 162 Sovereign Way; this woman (well not really) knew exactly how to dress to get him excited. From her heavily made up face, to her wide hips, to her sexy legs and large but elegant feet, she exuded sex. She didn't say anything, but curled a red painted fingernail at him beckoning him inside.
Brian's eyes locked on her ample bottom, the kick pleat of her pencil skirt inviting his gaze to lock on her shimmering sleek nyloned legs and sexy black high heels. He slammed the door closed behind him and followed Michele into the lounge. Part of the strategy that Brian had fabricated to deal with Michele the transvestite was to think of her only as a woman. If you looked closely at her you could see some of the give away signs: she was large framed, had big feet, a husky voice and an Adam's apple; but dressed the way she was, her feminine charms far outweighed any evidence of masculinity. Besides, regardless of anything else, she was just downright sexy!
Michele reminded herself of her own strategy for dealing with Brian; she would let him do what he liked, to a certain extent, but he was not to touch the front of her body between the neck and thighs.
Brian put his sample case on the coffee table and they sat on the couch, a little nervous and awkward with each other. Brian spoke first.
"Nice stockings Michele; they're Wolford Perlons seamless aren't they?"
"Yes they are; a donation from your sample case last week," Michele answered.
After thirty seconds of uncomfortable silence Brian moved in towards Michele and kissed her gently on the lips, his hands on her shoulders. The kisses became hotter and they were soon mingling tongues and grinding lips; Brian pushed Michele down on the couch and his hand fell to her stocking sheathed legs and he stroked and pawed at them.
"You'll ladder my stockings," Michele panted breathlessly into his mouth.
"It's not like I can't replace them," Brian laughed and pounced on her again, firmly kissing her and snaking his hand under her skirt.
Brian's hand smoothed over the welt of her stocking onto her garter strap and continued up her thigh towards her panties and Michele struggled and tried to push his hand away.
"No Luv; don't do that!" she instructed him.
"Why not luv; I bet you're wearing lovely knickers and I'd love to have a feel of them," Brian begged, knowing full well why Michele didn't want him touching her there.
"Please Brian; you can do what ever you want to my legs and bum but you can't touch me there," Michele replied in her husky breathless voice.
"Ok then; let's get yer skirt and blouse off so I can enjoy what's on offer," Brian pleaded, knowing full well that Michele would not acquiesce.
Michele decided it was time to be more assertive to keep Brian away from the parts of her body that she didn't want him to touch. She hadn't thought it would be this difficult to control him. Michele forced Brian away and pushed him back onto the lounge.
"Here; let me take the lead for a while," she giggled, trying to slow things down.
She straddled his lap, the seams and kick pleat of her skirt stretching to the limit and forcing it to ride up her thighs. She took off Brian's jacket and tie and folded them over the back of the couch. She unbuttoned his shirt and raked her nails across his chest as she leaned into him and kissed him passionately. Brian responded and slid his tongue into Michele's mouth and wrapped his arms around her inhaling her scent and tasting her mouth.
Michele decided that she had better continue to take the lead; rational thinking told her that she shouldn't touch another man's penis, but she was so excited that the very idea of touching Brian's erection for the first was highly exciting. She looked down and saw his cock tenting the front of his trousers just in front of where her thighs straddled his. She lowered a hand and felt the hard bulge of his phallus through the material of his trousers.
Brian was delightfully surprised when Michele took the initiative straddling him and allowing her skirt to ride up high on her thighs. While she removed his jacket and tie he stroked her thighs and then returned her kisses and embraced her. She was so sexy, he could taste her lipstick, and her perfume was driving him heady. He decided to allow her to take the lead for a while; but soon he was going to show her that her ruse was up. When she grasped his erection though his trousers he emitted a low growl from deep down in his throat.
Michele fumbled at Brian's flies, encumbered by his hard cock pushing at the material of his trousers and his fly buttons. She was aware that in a few seconds she would be touching another man's penis for the very first time. She had thought that the act would be repulsive; but in fact the opposite was the case, she was becoming highly aroused at the prospect.
Finally she popped open the buttons on Brian's flies and her hand groped inside his trousers and found the sleek hard shaft and bulbous head of his penis. The musky smell of an aroused male sex organ wafted from his flies and her nostrils flared like a woman in heat. She slid her hand down until she felt his pubic hair, then through the coarse hair to the base of his cock. Michele slid her open hand up one side of his cock and down the other. It felt foreign; hot and hard, but with a soft smooth surface.
She intertwined the fingers of both hands around the base of his cock and then slid them up the length of it, and rubbed her thumbs over the head. Each time she brushed the tip of his cock, Brian gasped a little. Brian's response was highly stimulating and she moaned into his mouth as she kissed him passionately, her lipstick smearing on his mouth. She raked her red painted nails along the smooth shank of his erection and felt his penis pulse and strain, the thick veins bulging prominently along the smooth shaft. Michele started to stroke his cock like that, using both hands on his penis. Brian grunted and started raising his hips to meet her downward strokes. He began to fuck Michele's hands. Michele looked down at Brian's cock moving in and out of her hands when he gently eased her mouth from his and spoke.
"Michele, hold on a minute please; I don't want to come yet" he pleaded
She stopped stroking, but didn't take her hands off his cock. She could feel it pulsing in her hands. Michele decided that she was going to bring on Brian's orgasm, she was very excited by the experience of touching another man's cock, but she was also determined that this was as far as she would ever go with another man. She had drawn a line in the sand in her mind; masturbation was ok, but anything else would be perverted.
Michele held Brian's shaft lightly in her fingers and rubbed his glans across the welt of her stocking. Brain groaned and pulled her face back to his and thrust his tongue inside her hot, wet mouth. Brian was intensely stimulated by Michele's ministrations but he was still in control. He was letting her take the lead for a while but he was determined that this bitch was going to find out who was ultimately in charge; she would soon learn that he knew her all about her secret.
Brian guided one of Michele's hands back to his cock and bought the other to his chest. She needed no more urging and she groaned at her hand came in contact his erection and the fingernails of her other hand scoured his chest. She gently took Brian's cock in her fingers and began to slowly traipse her fingers around it, over its length and then back down the shaft. She then placed the hard flesh of his penis against the soft; nylon encased flesh of her thigh and rolled it against the diaphanous material of her stocking.
Brian humped at Michele's leg, his glans secreting a thin silvery thread of pre-seminal fluid that glistened on the dark welt of Michele's stocking. He was building to his orgasm, not yet close enough that he couldn't control it, but he wanted release, and it would not be against her legs or her feet as much as she thought it might be. Brian had other plans for Michele Rodgers.
Brian continued to kiss and embrace Michele but he snaked one hand away from her and reached for his jacket. He fumbled around until his fingers found one of the pockets; they closed around a small glass jar. Brian extracted the jar from the pocket and with some difficulty, he one-handedly unscrewed the lid. He put his fingers inside the jar and scooped up a dollop of the contents and bought his hand down to his erection, and easing Michele's fingers out of the way, he smeared his shaft with a generous coating of Vaseline jelly.
Michele was initially confused when Brian pushed her had away from his cock; at first she thought he just wanted her to stop stimulating him for a while. Then she felt him take his own shaft in his hand and she broke away from the kiss and looked down at his lap. Brian's fierce erection stood out proud of his trousers, the glans an angry red. It was glistening with a coat of viscous emulsion. Then the odour of the Vaseline wafted up to her and she realised what it was. Did he want more lubrication? Wasn't his pre-seminal fluid lubrication enough? Did he have a fetish for Vaseline as well as nylons?
Brian moved his hands to Michele's thighs and pushed at her skirt until it was rucked around her buttocks and then slid his hands under her buttocks and lifted her up. He pulled her towards him and pushed his groin forward.
Michele suddenly realised what Brain was doing; he was trying to fuck her! My god! What would happen when he found out she was a man! Would he be disgusted? Would he hit her? Would he scream abuse at her? Would he tell everyone her secret? Michele began to panic and tried to squirm free.
"No, no, no, no, no, nooooooooooooo!" she screamed.
"We can't do this. Put me down! Put me down Brian!" she begged.
"Oh don't worry Michele, we can and we are going to do this!" Brian hissed.
Brian's fingers were digging into Michele's buttocks entwined in her satin panties and he pulled the gusset to one side exposing her bare buttocks and sphincter.
"No! Brian! It's not what you think!" Michele beseeched him to stop.
Brian payed no heed and wriggled his hips until his erect penis was positioned directly underneath Michele's soft white buttocks. He lowered her slightly and he felt his cock nestle against Michele's anal bud. Michele wriggled and fought in his lap; she put her feet on the floor and tried to push herself up and away from the greasy weapon snuggled between her buttocks.
Brian let go of Michele's thighs and buttocks and placed his hands on her shoulders. He strained and pushed Michele down into his lap whilst wriggling his groin to keep his penis positioned at the entrance to her anus. Michele fought against him but Brian was too strong for her; she was losing the struggle and slowly being forced down into Brian's lap. She felt the Vaseline covered tip of Brian's glans against her anal opening and she gave one last upward shove to try to escape her fate.
"Please Brian; please don't do this," she begged.
Brian looked into her pretty painted face and smiled evilly.
"I'm sorry luv, but you bought this on yourself," he said.
Brian pushed down on Michele's shoulders with all his strength and slowly impaled her on his phallus. Michele screamed and Brian clamped his mouth over hers and shut off her cries. Brian started to push up hard as his cock slid slowly inside Michele's anus. Michele felt her sphincter stretch as Brian's glans began to invade her, the lubrication of the Vaseline easing the invading member's passage. The initial pain was almost unbearable and tears ran down Michele's cheeks leaving trails of mascara as Brian's cock continued to intrude into her bowels.
Brian was still kissing Michele despite her moans and cries, his he continued to push her down into his groin but he slackened his grip slightly and gradually changed from a vice grip to a hug. He fluttered gentle kisses on Michele's cheeks, eyelids and then kissed her lips.
"Easy Michele, relax, its ok," Brian tried to sooth her.
Michele was now fully violated as Brian's cock forced its way completely inside her and her soft buttocks rested on his groin. She forced herself to relax the muscles of her sphincter and back passage and finally the last inch of Brian's cock was inserted inside her; he was buried in her anus up to the hilt of his shaft.
Michele put her high heels back on the floor and took up some of the weight of her body so that Brian's cock was not jammed so uncomfortably inside her. Her tears and sobs began to stop as she resigned herself to the situation. Brian lifted her slightly and then let her own weight lower her back down. He was slowly fucking her. As Michele felt the gentle thrusting inside her, she forced herself to relax further and Brian's cock was able to thrust in all the way, deep into her bowels causing her very little pain. As her buttocks came down into his groin he released his grip on her shoulders and rubbed his hand along her stockinged thigh, further stimulating himself.
Sensing Michele's compliance Brian dropped his other hand to her buttocks and stroked her slinky satin panties. Michele began to realise that the slow fucking was actually arousing her; she felt pleasantly full; the base of Brian's shaft stimulated her sphincter whilst his glans stimulated her prostate gland deep in her bowel. She never realised that anal sex could actually be pleasant for the recipient.
With her feet firmly planted on the floor Michele could control the rhythm of the fucking and she flexed her knees and slowly moved her lower body up and down letting the tip of Brian's cock come all the way out to the ring of her sphincter and then lowered herself down on him until his entire length was buried inside her and his groin rubbed against her pantied buttocks. She lowered her mouth to Brian's and kissed him fervently thrusting her tongue into his mouth.
"You bastard!" she panted into his mouth, "You knew all along!"
"I didn't figure it out until this morning luv, but let's talk about that later," Brian gasped.
He pulled Michele's lips down to his and thrust up to meet her and slid his tongue into her mouth. They slowly fucked, Brian matching his thrusts to her rhythm; he scrunched her pantied arse and eased his cock in and out of her. He moved his hands to her thighs and rubbed her stocking legs. Michele reached out and locked her arms around him as they kissed passionately.
Brian took hold of Michele's garter straps and leaned back into the lounge to he could look as Michele sitting astride him. She was lovely; her heavily made up face framed by the brunette bob; she looked even sexier now because of her racoon eyes caused by her crying episode and her ruby red lipstick was smeared around her mouth from their the fervour of their kissing.
Her suit jacket was open and her false breasts thrust against her white silk blouse. His eye followed her body down to where her tight skirt rucked around her waist exposing her creamy white thighs above her stocking welts; he entwined his fingers in the garters of her bustiere; her legs shimmered, sheathed in the seamless flesh toned stockings. The smell of her perfume mingled with the musk of their sex assaulted his nostrils, exciting him further.
Brain lay back timing his thrusts as Michele slowly lifted and lowered herself up and down, impaling herself on his rampant cock.
Brian took Michele's buttocks in his hands and squeezed, pulling her down against him and Michele issued a guttural moan. She adjusted her position putting more of her weight on Brian; and putting more direct pressure on her prostrate gland as she writhed, impaled on Brian's cock. Michele leaned forward and rocked against Brian, her hands falling forward, landing on either side of his shoulders, then she pulled back as she braced herself against him. She slid forward and back, and rose up and down, feeling an intense pleasure emanating from her back passage unlike anything she had ever experienced before; she threw her head back and moaned.
"Oh god Brian, I'm going to come!" Michele moaned.
"Oh ... me too; I'm so close." Brian gasped.
Brian leaned forward and let go of her garters and grabbed her hips. Michele bounced up and down on his lap plunging Brian's hard phallus in and out of her, her motion irregular and choppy as she got closer to orgasm. Brian clutched at her hips and thrust up against her, adding his own movements to their sexual frenzy.
Michele's breathing suddenly became laboured and she stopped rocking.
"Oh my god here I go!" Her fingers dug into Brian's shoulders.
Brian continued to push his penis deep into Michele's anus, increasing her stimulation as his cock began to convulse. He thrust into her, slowly, deliberately knowing that he wasn't going to last much longer. Michele arched her back, dug her fingers into his shoulders and bore down against him as she moaned. They were both about to climax.
Michele bore down on Brian, impaling herself on his shaft and wriggled her buttocks as her orgasm shook her body. Her own penis, only semi-erect, but freely leaking pre-seminal fluid suddenly spasmed and she flooded the front of her satin knickers. The hot sticky pool of semen saturated her knickers and soaked through the satin and began to drip down onto her thighs, staining her tan stocking welt a darker shade of brown.
Brian pulled Michele down on to his penis as he shuddered with the paroxysm of pure pleasure radiating from his groin, travelling upward through his body. As he ejaculated streams of hot semen deep into Michele's bowels; he shuddered and groaned. He was experiencing the most intense orgasm of his life as this fully dressed transvestite slut writhed in his lap, milking him of the last of his seed.
They both slowly came down from their orgasms and as their shuddering and moaning subsided Michele leaned forward and kissed Brian gently on the lips and when Brian responded, the kiss became hot and feverish as the last dribble of Brian's issue was deposited deep inside Michele and the last trickle of her semen expelled into her panties.
They kissed for a few minutes, neither of them saying anything until the afterglow of the sex began to slowly dissipate. Brian reached for his jacket again and this time he produced a handkerchief from one of the pockets. He dabbed it on Michele's thighs, cleaning away the sticky mess and then as he eased Michele up and off him and wiped at his semen and Vaseline coated, slowly deflating penis. Michele took the handkerchief from him and wiped between her buttocks and pulled her panty gusset back in place and then adjusted her skirt as she stood up. She could feel the pool of semen in the front of her panties soak into the material of her skirt.
"I think I need to clean myself up a bit and change my underwear and skirt," Michele giggled.
"But that was lovely. You knew my secret you bastard!" she chided Brian.
"Not until this morning; and to be honest I didn't know what I was going to do. I was wondering what it would be like to fuck a transvestite but I was still unsure about whether I would go through with it until I got here. When you met me at the door dressed like that, you took away any reservations I had," he grinned.
"Now; while you get cleaned up and changed, I'll clean myself up in the kitchen and pour us both a drink. I think we need to talk after what's just happened between us," Brian said.
"Yes, I think so," Michele replied.
Brian lit them both a cigarette and Michele took hers and took a heavy drag as she turned to leave room. Brian reached out and slapped her playfully on the buttocks.
"Cheeky cow!" Michele reproached him.
"Wait until you come back down here Michele; I've got some great Aristoc stocking you're going to look fantastic in," Brian smiled, the small creases in the corners of his eyes crinkling.
Michele left the room with self-satisfied smile on her face and walked towards the staircase.
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