Transvestite Slut Caught and Punished

By Kelly Maitland

Holly accidentally catches her boyfriend wearing one of her dresses and takes cruel advantage of his weakness for her clothing.

'That’s good. I like my whores to be obedient and docile. Get your filthy tongue in all the nooks and crannies. You can lick my toe. In fact, I demand you do. That’s right. Lavish it with your misplaced love and devotion. Be a pervert, Rebecca. Love those shoes like the shoe slut fetishist you are. You don’t have to pretend you’re normal anymore. Those days are behind you. You can now be the shoe slut you always were. This is your place in the world, Rebecca. This is it. You belong down there. You belong down at my feet licking my shoes. Don’t you? Don’t you?'

Chapter headings:

My Mother’s Shoes
Caught Wearing Holly’s Yellow Dress
Holly Dresses Me Up for Her Amusement
Spit Roasting Rebecca
Holly and Sophie Urinate On Rebecca

• Language: English
• Publisher: Kelly Maitland
• Release date: Nov 16, 2017
• ISBN: 9781370816774

Kelly Maitland

AN OFFICE OVERRUN WITH PERVERTS [NOVELLA]A new office employee discovers his place of work is under the control of a perverted cabal of women. They want him to do unsavoury things of a sexual nature.THE THERAPEUTIC BENEFITS OF SADOMASOCHISM [NOVELLA]A female psychology student undergoes training at the hands of a controversial psychiatrist who uses sadomasochism as part of her methodology.FETISH SEX ROLE-PLAYING WITH HANNAH [NOVELLA]A woman indulges in her kinky sexual fantasies and tries to introduce a reluctant man to the pleasures of BDSM.STUDENT SASHA HAS KINKY SEX FOR MONEY [NOVELLA]Sasha French is the archetypal ‘girl next door’ with good bourgeois standards of conformist moral behaviour. Her student debts are piling up when she is offered money in exchange for kinky sex. Those morals don’t last long and she agrees to participate in a foursome with two guys and another woman.CRUEL SABRINA WANTS TO PISS ON MY FACE [NOVELLA]An office worker with a fetish for stockings thinks he’s got lucky with a pretty co-worker, but events take a weird turn after she’s handcuffed him to the hotel bed.TEACHING THE LATEX SISSY MAID TO BE OBEDIENT [NOVELLA]A man joins a strict household as a latex maid and is given the feminine identity of Samantha by his cruel mistress.SOLD AT AUCTION TO DEVIANT S&M PERVERTS [NOVEL]A brothel madam auctions Erica’s sexually inexperienced mind and body to the five highest bidders.TRANSVESTITE SLUT CAUGHT AND PUNISHED [NOVELLA]Holly accidentally catches her boyfriend wearing one of her dresses and takes cruel advantage of his weakness for her clothing.TURNED INTO A BISEXUAL PORN STAR BY A DOMINATRIX [NOVEL]A seemingly heterosexual chambermaid stumbles upon a professional dominatrix working in her hotel. The dominatrix cruelly enslaves the chambermaid and turns her into a bisexual porn actress.UNRELENTING SADOMASOCHISTIC FEMINISATION: TRANSFORMING MY HUSBAND INTO A PATHETIC CROSSDRESSING SISSY [NOVEL]Sarah’s husband talks her into trying sadomasochism to spice up their sex life. He quickly loses control of the games they play when she develops into a far more inventive and malicious dominatrix than he expected. Finding himself in a dress kneeling before a group of strange men was not what he had in mind.DRINKING KATE’S PEE FROM A DOG BOWL [NOVELLA]Keith has a sexual fantasy of a depraved dominatrix making him drink her freshly urinated piss from a stainless steel dog bowl. Five experts in femdom humiliation have already played out his perverted dream but none as inventively as his next hire: Mistress Judy AKA Kate, his very angry wife who has just discovered that he’s been sleeping with her sister.MISTRESS MIA’S FEMDOM SISSY SESSIONS: TURNING JAMES INTO TRANSVESTITE LATEX SLUT NATALIE [NOVELLA]James soon learns to regret picking up Mia from a bar when she enslaves him as her submissive plaything. From there things go from bad to worse as she takes a fancy to the idea of feminising him. She doesn’t want to stop at dressing him up, she wants her girl to be a real heterosexual c*******r.HEADMISTRESS MISS GULLIVER USES HER CANE TO TEACH AND PUNISH A PERVERTED SCHOOLBOY [SHORT STORY]Head teacher Miss Gulliver uses corporal punishment to educate Alan to respect his female classmates after he is caught looking up their skirts during English class. [Published as THREE KINKY TALES OF MATURE FEMDOM PERVERSION]YOUR WISHES AND DESIRES ARE LESS THAN NOTHING: A LATEX HANDJOB SESSION [SHORT STORY]A man in a gimp suit hires a fifty-six-year-old prostitute to dress up in latex and perform a handjob on his disappointingly small penis. [Published as THREE KINKY TALES OF MATURE FEMDOM PERVERSION]WEAK MEN ARE SUCH EASY PREY FOR DEBAUCHED PSYCHIATRIST DR CHLOE RICHARDSON [SHORT STORY]A psychiatrist abuses her position of trust and power over a weak-willed patient to fulfil her heartless sadomasochistic desires. [Published as THREE KINKY TALES OF MATURE FEMDOM PERVERSION]PLUGGED LINGERIE SISSY LOCKED IN CHASTITY AT THE PHOTO SHOOT [NOVELLA]A transvestite arranges a fetish photo shoot in a hotel room and tries to seduce the straight male photographer.RELUCTANT SISSY AUDREY MADE TO PLEASURE MEN FOR THE FIRST TIME [NOVELETTE]A heterosexual man is made to service two gentlemen while wearing a dress, stockings and high heels after unintentionally initiating a feminisation session with a dominatrix.INSTRUCTED TO J**K OFF BY CRUEL NATALIA FORREST: HUMILIATING HER NEW RELUCTANT LATEX SISSY MAID [SCREENPLAY AND VIDEO]Natalia Forrest’s boyfriend disappointed her for the last time. So she put him in a latex dress and changed his name to Miranda. Then she explained that Miranda was going to get intimate with her other boyfriend. The 22 minute movie was based upon a chapter from the book PLUGGED LINGERIE SISSY LOCKED IN CHASTITY AT THE PHOTO SHOOT.NATALIA FORREST’S FIRST-TIME KINKY BDSM LESBIAN EXPERIENCE [SCREENPLAY AND VIDEO]Natalia Forrest graphically recounts the kinky tale behind how she acquired her sexy black patent leather boots. Her perverted story involves boot licking, pee drinking, bondage and first-time lesbian sex. She becomes so turned on describing her degradation under the cruel but sensual tyranny of Mistress Molly that she has to retire to the bedroom to masturbate. The 38 minute movie was written by Kelly Maitland.NATALIA FORREST GRAPHICALLY DESCRIBES HER IMMINENT TRIPLE PENETRATION TO HER SOON TO BE CUCKOLDED HUSBAND [SCREENPLAY AND VIDEO]Kinky Natalia Forrest explains to her husband that he is going to have to impotently watch her have group sex with his despised boss, his best friend, and his brother. The 36 minute movie was written by Kelly Maitland.A FEMINIZED HUSBAND EXPLORES HER NEW SUBMISSIVE SEXUALITY WITH DOMINANT MEN AND WOMEN [NOVELLA WRITTEN BY FIVE GHOSTWRITERS AND EDITED BY KELLY MAITLAND]A husband reveals to his wife that he’s been harboring fantasies of being feminized and made to pleasure men while pretending to be a woman. Instead of being appalled by his confession, his wife agrees to help him make his perverted fantasy a reality. She sets in motion a course of crossdressing, d**k sucking and anal for Stephanie AKA Steven.NATALIA FORREST WANTS TO SHARE A TEN MAN BLOWBANG WITH A SISSY [SCREENPLAY AND VIDEO]Natalia Forrest has a flash of kinky inspiration when she is offered the chance to film a ten man oral orgy. She compels a man with no history of feminisation to put on a dress and get on his knees to share the experience alongside her. The 38 minute movie was written by Kelly Maitland.ON THE ORDERS OF SISTER BERNADETTE: NATALIA FORREST SUFFERS BONDAGE AND ANAL [SCREENPLAY AND VIDEO]Natalia Forrest complains bitterly about a domination session with Sister Bernadette that was more extreme than she anticipated. Being tied to a bed and abused by a latex nun was one thing, but to be used anally by four male strangers was not what she had expected. The 37 minute movie was written by Kelly Maitland.A GIRLY CHAT WITH HEARTLESS NATALIA FORREST [SCREENPLAY AND VIDEO]A woman finds ample reason to regret booking Natalia Forrest for a BDSM couples session with her husband. The 54 minute movie was written by Kelly Maitland.PORN STAR NATALIA FORREST INTERVIEWED (SHE’S NOT BAD, SHE’S JUST EVIL) PARTS 1-4 [VIDEO]Adult actress and glamour model Natalia Forrest talks candidly about her career in the adult industry. The 130 minute documentary features Natalia answering questions written by Kelly Maitland.Video previews: youtube.com/channel/UCLlbMb22OesDW6ijx4istGwContact address: [e-mail]

Book preview

Transvestite Slut

Caught and Punished

Kelly Maitland

© 2016 Kelly Maitland

Contents

My Mother’s Shoes

Caught Wearing Holly’s Yellow Dress

Holly Dresses Me Up for Her Amusement

Spit Roasting Rebecca

Holly and Sophie Urinate On Rebecca

My Mother’s Shoes

I like to wear women’s clothes. I’m not proud of it. It’s not like I’m in any rush to admit it to the world. It’s just a fact. I get turned on by the thought of wearing clothes that aren’t meant for me.

I’ve no idea why my mother’s high heels exerted such a strong pull on my young sexual imagination. I can’t recall any specific moment when they became so interesting. They were just always there, tantalising me with a yearning that I couldn’t understand, never mind articulate. They held a promise of something...obscure and interesting.

Then one day, years later, I watched a movie and for one brief scene a man was seen in women’s underwear. Black bra, panties, stockings, suspenders and black high heels. He wasn’t made to look ugly or stupid. He was made to look exotic and attractive. Luckily no homosexual desires stirred in me. I was not attracted to him. What it did though was open my impressionable mind to the idea that men could wear clothing that was not meant for them. Before seeing this image, the idea of wearing a dress or panties hadn’t even occurred to me. It wasn’t like anyone watched Monty Python and found themselves inspired to dress up like unattractive old ladies. Unless they were planning to do comedy skits.

Annoyingly I have no idea what that film was. I’ve since searched high and low but without any luck. I think it was a spy movie mixed in with some gangster stuff. I remember a few scenes. Or at least the locations if not the actual contents of the scenes. There was a graveyard, a train station and a brothel, which is where the transvestite scene took place. I’m sure someone got shot while taking a bath. Anyway, I saw it and the idea was planted in my mind.

I was smart enough to hesitate before doing anything about this new concept. I knew if I put on my mother’s clothes I would have crossed a line and I’d be a pervert. Even worse, I might like it and want to do it again and again.

After what seemed like a month of procrastinating, but in all probability was no more than one week, I did it. Somehow I got up the gumption to try it for myself. When the house was quiet I sneaked into my mum’s bedroom and put on a pair of her high heels. They were closed-toed court shoes in black patent leather. They had a four inch heel on them. At that age my feet fit her shoe size with only a slight tightness. I trotted about in them for a few minutes, and then I took them off and put them away.

It didn’t really do anything for me, except make me feel silly.

A week later, when the house was empty again, I went back into her closet. This time I put on a pair of her white lace panties. Then I rolled a pair of black low denier tights over my legs. Then I put on a pair of red open-toed three inch heels. They had a strap across the ankle that I remember struggling for several minutes to buckle. I only planned to wear the stuff for five minutes, but once in the red heels I had to go further and put on a matching red dress. It was too good an opportunity to miss.

I found a red dress with a tight pencil skirt. I put it on. It fitted me surprisingly well.

I walked awkwardly back and forth in the heels and admired myself in the mirror. Sure, I felt stupid but I was also aroused. I pulled my dick out the panties and masturbated.

Disaster struck when I took off the dress. I didn’t pull the zip all the way down and I ripped the dress. There was a one inch tear at the small of the back beside the central zip. There was nothing I could do. I just had to put everything back how I found it and hope she wouldn’t discover it for months. Hopefully when she did notice the rip, she’d assume she must have done it and just hadn’t noticed it at the time. It would have been a big leap to suspect her son had worn the dress. Right?

I never heard a word from her about it. If she noticed it then she said nothing to me about it.

I was too scared to touch her dresses again after that. I was also paranoid that I’d stretched out her tights too much so I didn’t try them on again. I confined myself to putting on her panties and shoes.

In total I doubt I did it more than ten times all together, including the time with the red dress. I wasn’t a hardcore transvestite. I didn’t need to wear feminine clothes. It wasn’t a compulsion or an obsession. It was just something I liked the idea of doing; and on the few occasions I did it, I mostly enjoyed it. I’ll put it this way: it was worth the risk of getting caught. There was enough pleasure that I’d take a small amount of peril to chase that gratification. Wearing shoes and panties were an acceptable amount of risk. Tights and dresses I was too scared to touch. They weren’t worth the peril of discovery.

Sadly in time I grew out of my mother’s shoe size. The only reason why I stopped my transvestite activities was because my feet no longer fitted. Panties on their own seemed pointless. In the end I think it was all about the shoes more than it was about anything else. The rest of the items of clothing were just an addition to the shoes.

It was no great hardship not wearing women’s clothing. The years without dressing up were fine. I may have fantasised a few times about dressing up as a woman, but it wasn’t my only sexual fantasy. It was an itch that didn’t bother me that much over the years as it went unscratched.

When I eventually got a girlfriend I was content to adore her while she wore her own clothes. I felt no need to climb into them myself when she wasn’t around. Nor did I have a desire to share my fetish with her. It was my dirty little secret.

Serious girlfriend number five was different. By pure chance Holly’s dress size and taste in clothing coincided with my own. Only her shoe size was too small. She’d also leave me alone in her house for many hours when she was sometimes working late at night. She worked in an office by day but sometimes she filled in at a bar at nights when they were slammed. She used to work there as a student and remained friends with the owner.

So I was intermittently left alone in a house filled with excellent ladies clothes that fitted