Chapter 1 – Influences

Monday 30th March 2015

Knightswood

Glasgow

I had turned fifty on Sunday, and apart from brief phone calls from my grown-up son and daughter, I went out for a meal with Emma, my wife. We got home, enjoyed a bottle of wine, and after the late evening news, we went to bed. She kissed me, murmured something about an early start, rolled over and slept, but I didn’t doze off until my arousal calmed.

Life was good, although the sex had ended early in our relationship. Emma had always been unadventurous in bed, so for years we had indulged regularly in vanilla sex. Before it fizzled out completely, our love life had become a ritual instead of a pleasure, and I knew that it would fade.

Here I was, at the start of another week, and the one thing to cheer me up was my new working arrangement. I was qualified in design and illustration, but I had moved regularly from one job to another and gained valuable experience. Among my successes in the past, I’d created adverts for billboards, designed official documents, magazine covers, book covers, and much more. However, this was my first day working as a freelance designer.

I pulled on a T-shirt and jeans before going downstairs for breakfast.

Emma was gulping coffee. “It’s easy to see that you’re working from home now, Peter.”

I grinned. “I’ve done my share of commuting, and if I can earn a living freelance, I intend to savour every aspect of the lifestyle.” I drank a glass of juice and fixed myself a bowl of cereal.

“You’re right, of course, and I’m jealous.” She laughed and buttered a piece of toast. “Here I am, going in early to deal with a stocktake, and you’re up because you have the choice.” She nibbled her toast. “Do you have any projects as you begin this new phase?”

“Yes, and strangely, my first job is for the studio I left last Friday. I have a set of book covers to work on, and the time frame is loose, so I’m not under any pressure.”

“I’m pleased for you.” She finished her toast and took another mouthful of coffee.

“Are you working in the usual department?”

“Yes, so I’ll be up to my neck in bras, knickers, nighties and so on.” She grabbed her bag and coat. “There are some positive aspects in my day. Kathryn is in charge of the department, and apart from being my friend, she knows how to get the best out of people.”

“What else is positive?”

“I ought to be home earlier than usual because I’m going in at this time.”

“Are you sure you don’t want me to take you in?”

“Good heavens, no. Kathryn is giving me a lift, and she’ll be here any minute.”

“Does she have to go out of her way to pick you up?”

“No, she lives in Clydebank, so it’s not far. It’s only a slight change to her route into Glasgow.”

I went out to the front door, and after kissing Emma on the cheek, I waved at Kathryn, who’d just parked at the end of our driveway. When my wife opened the front passenger door, it allowed a glance at Kathryn’s curvaceous figure and a glimpse of her legs.

“Oh shit,” I murmured. “Kathryn smiled back at me, so she must have known I could see her.” I hoped my lecherous gaze wouldn’t be part of their early morning conversation.

*

Suitably equipped with a fresh coffee, I went upstairs to my study; a converted bedroom. The room wasn’t big, but it had a south-facing window which offered me a lot of natural light and a pleasant view of a large public park. I switched on my laptop and slowly turned my swivel chair to appreciate my new work environment.

I had an email from my old boss which supported an earlier message.

Subject: Book Cover Project

‘Hi, Peter, and congratulations on leaving the rat race. As promised, I’m sending your first freelance project on behalf of one of our clients. It’s the cover design for the first in a series of books. I didn’t give you any details in my previous message because the author had second thoughts about the series title.

I’m now enclosing the first book’s manuscript, as supplied by the author. I told her that you preferred to read the story before working on any cover design, so I hope you enjoy it.

The author writes erotica and is called, Miss Tress Rools. She appreciates you reading the tale first, and has added notes for you at the end.

Best regards,

Graham.’

Five minutes later, I’d sent the document to my Kindle and opened it. I read the title aloud. “All Dressed Up – Book One.” I sipped my coffee and also read the blurb aloud.

“I caught my husband watching girls who were walking to the local sixth-form college, and I told him to stop acting like a pervert. I mistakenly thought he was fantasising about the teenage girls. One day I borrowed his computer and discovered the truth was more bizarre. Our relationship has gone through a few changes since that day.”

I liked the sound of the plot and grinned as I considered that my first new project was to be designing covers for erotica. I finished my coffee and set up a blank document for notes before I started reading the story.

The author was good, and I was aroused before the first chapter’s end. Although it had no relevance to the cover, I liked the idea of short chapters, and I consumed them like squares of a luscious chocolate bar. I didn’t stop reading for two hours, and I was over halfway through.

“Time for a mid-morning coffee, although another five minutes of that and I’d be having a mid-morning wank.”

*

At ten minutes to one, I finished reading the story and went on to read the author’s endnotes.

‘This is a true story, so whether you’re a man or a woman, if it made you feel good, maybe you should check out my pages on the Kinks and Queens website. The link is below, and I use my author’s name on the site.

Regards,

Miss Tress Rools.’

Knowing that I’d just read a true story, I felt a strong urge to click on the link. I occasionally viewed porn when I wanted to enjoy a wank, but Kinks and Queens was sure to be a website with real people, and not actors.

I scrolled to the next screen on the Kindle. ‘Notes for the cover designer.’ I read on.

‘Hi, Peter.

I hope you enjoyed this naughty tale, and it has provided inspiration. You come highly recommended by Graham, so I’m sure the job will be done well.

As you’ll know, the eBook version can be slightly more risqué, so it will be up to you if you create a different solution for the paperback version.

Thank you,

Tress.’

I reread the endnotes for readers and the notes for me, and while they impressed me, I loved the author’s name, Miss Tress Rools. My head was full of creative thoughts, but something lingered in my mind, and I was hesitant about following up on it.

“Lunch time, Peter,” I announced and tried to ignore the hoarse tone in my voice. I was panting as I went downstairs to organise a bite to eat and a hot drink.

As I sat at the breakfast bar enjoying beans on toast and a large mug of tea, my thoughts continually drifted to the story I’d just read.

*

The main character in All Dressed Up, was Alan, a husband who went to work every day and appeared to live a normal life, but he’d become addicted to viewing porn. One of his favourite categories was transgenders, especially girls with extra, sometimes unkindly referred to as shemales. Another favourite was crossdressing, but mainly featuring men in a girl’s school uniform.

If Alan had kept to that naughty habit, he could have continued to browse the websites and play with his cock as much as he wanted, but he made a mistake. Alan’s wife, Theresa aka Tress, being an author, worked from home. When Theresa had told Alan to stop acting like a pervert, he was duly embarrassed and told her he wouldn’t do it again.

A few days later, while Alan was at work, Theresa had an important file to send but had a problem with her laptop. She borrowed Alan’s computer to deal with the message. Out of curiosity, she looked at the browsing history on the machine, and discovered three links to a porn website. Intrigued by the name of the site, she investigated each of the links.

One link went to a scene where a crossdressed man in a girl’s school uniform was being spanked and made to suck another man’s cock. Another link went to a crossdressing scene in which a man in lingerie and stilettos was bent over sucking another man’s cock. In the third link, while giving a blowjob, the crossdresser was being taken from behind by a third man; also crossdressed.

Theresa noted the three links but said nothing when Alan got home from work. She knew that her husband would be easy to catch out if she planned with care. She waited until Alan’s next scheduled day off and told him that she’d be attending a meeting until late in the afternoon. 

The ploy worked, and Theresa arrived home early to find Alan in a nightie and knickers, spreadeagled on their bed. He was pumping his engorged cock with one hand while caressing the nightie and knickers with the other.

Theresa hesitated about what to do next. She was a stronger individual than Alan and allowed him to think that his indiscretions would be forgotten because he’d apologised. She didn’t bring the subject up for two weeks, but, by then, she had collated evidence to prove that her husband had continued to crossdress.

Unknown to Alan, his wife had set a trap by putting away her underwear, other clothes, and shoes in a certain way. When done, she used her phone to take pictures of the contents in the dresser drawers and her wardrobe. Whenever Alan had been alone in the house, Theresa compared the drawer and wardrobe contents to the earlier pictures.

 Satisfied that she’d caught him, Theresa confronted Alan with the pictures on her phone. She saw that his confidence had been knocked, although he denied touching her clothes or shoes. She asked him to power up his computer and open the browsing history, which he did, but the links were all innocent websites. Alan smiled and asked why she wanted to look at the browsing history. He was dumbstruck when she handed him the list of three links and told him to bring them up on the screen individually. He broke down, apologising for lying about borrowing her clothes.

The following day, after Theresa had explained Alan’s options, she became his mistress and began feminising him. She said that Alan’s occasional alter-ego was to be called Allison, and her favourite costume on him was a girl’s sixth-form uniform. By the time Theresa had applied Allison’s makeup and fixed her hair in pigtails, nobody would have recognised the real person.

Alan thought he’d been given a kind of reprieve for a month because he’d not been kicked out. His wife had him crossdressing most nights to become Allison, sometimes bent over Theresa’s legs for a spanking.

On a Sunday morning as he was heading to the bathroom, his wife stopped him and told him he was to shave off all his body hair. When he tried suggesting that he didn’t have much, Theresa told him to have his normal shave and call her when he was done. Alan did as asked, and stood patiently while his wife performed the extended hair removal. She shaved his chest, arms, underarms, pubes, legs, and between his buttocks.

Before Alan climbed into the shower, Theresa told him that she expected him to shave to that extent every day, and he was to use moisturiser all over afterwards. Alan secretly enjoyed going that extra step with the feminisation, and he’d become accustomed to the changes to his life. It had become routine for him to get home and change into Allison after his shower, and most Sundays, he spent the entire day en femme.

The next stage of feminisation wasn’t as welcome. Theresa caught Alan en femme and wanking while viewing porn on the internet. The following day Alan was to discover the true meaning of chastity, when a small acrylic cage was fitted around his shrunken cock and balls. In the weeks ahead he learned about milking, pegging, rimming, and other terms that had previously only existed in the world of porn that he viewed.

*

Having spent my lunch break thinking about the story, I returned upstairs, with a burning desire to see the pictures on Miss Tress’s pages.

I had been thirty when the internet became a part of everyday life, so like other people with a family and a full-time job, I’d only dabbled in surfing the web. In more recent times as my sex life faded, I’d gone online to view porn sites to help arouse me, and I loved to watch other people doing things while I wanked and imagined taking part.

I sat facing my laptop, trying to convince myself that I was performing research. I typed the link for the Kinks and Queens site into my browser. There was a selection of gender symbols but no pictures. The message was straightforward:

‘If you’d like to join our kinky community,

you need your real name to register,

but membership is FREE and confidential.’

I stared at the screen, remembering a promise I’d made myself, never to register on a porn site, even if it were free. I thought again about the woman who had feminised her husband. According to the story and the author’s endnotes, there were pictures of them both on the website.

“I hope I don’t live to regret this.” I reread the message on the screen, typed in my name and created a simple password. Another screen appeared with a column of empty text boxes. I typed my age and gender into the first two. The other boxes became active and required a username, a home location, and sexual inclination. There were boxes which could be left blank or completed later.

As I sat back in my chair, staring at the screen, I slowly caressed the throbbing bulge in my jeans, and imagined scenes from the porn sites I’d visited. I wanted to remain anonymous, so Peter, the heterosexual fifty-year-old man from Glasgow, was no good.

“I know what to use,” I said aloud, remembering Corinne, a favourite teacher from my school days. I looked at the name for a few seconds and added, is Curious. “Corinne is Curious” I said aloud. “Now, that’s a good username.”

I continued with my profile, saying that I was a bi-curious crossdresser from Clydebank, which wasn’t far from where I lived. I bit my lip, and trembling with excitement, tapped the enter key. The page refreshed, and my homepage came up with a small box at the top left.

Inside the box, it said, ‘Upload my pic’, or, ‘I’m coming soon’.

I didn’t have a picture to pretend it was me presenting as a woman, so I selected the second option and looked around the homepage. Apart from an image and username, there were headings for My Gallery and My Thoughts. At the top right, more headings read, Contacts, Notifications, and Help. The final menu included Log out.

I felt my face warming, and all I’d done was register.

“I’ll look at the Miss Tress Rools page and her pictures, and afterwards, I’ll unsubscribe.”

I typed the username into the search window and hit the return key. The picture was an attractive woman, and the profile stated:

‘Hi, guys. I’m a mature woman who has always enjoyed sucking cock, and in recent months, I’ve had my husband do it too. I discovered by accident that he liked to dress up and watch naughty boys presenting as naughty girls. I feminised him, and you’ll see the results in my gallery.

I taught him how to behave like a girl so that, as a she, my girl looked and acted properly when dressed. I followed that with humiliation of various types. When I was confident that my man was feminised, I started to invite men of different ages to visit and play with my naughty girl.

Allison is my naughty girl’s name. She sucks cock, and swallows cum, but I haven’t made her take it in her pussy—yet. This whole situation started when my husband viewed porn, borrowed my lingerie, lied about it … and got caught.’

I selected Miss Tress’s picture gallery and slowly went from one picture, to another, zooming in on the detail, and becoming more aroused as I continued. I’d studied at least ten pictures before I paused, panting, and realised that after viewing a picture of Miss Tress, I had concentrated on images of Allison. She looked amazing, dressed in lingerie and heels, and in a school uniform among other costumes.

I murmured, “I can’t believe that a man would become a fetishist, or addicted simply by trying on sexy lingerie a couple of times?”

Five minutes later, I had undressed and was getting into one of Emma’s short nighties and a pair of lace knickers. My cock was throbbing as I sat at my laptop again. I looked down at the bulge in the knickers to see a growing damp stain. I lifted the waistband of the delicate garment, and the glistening, circumcised head of my cock stared back at me.

I slowly stroked my cock with my right hand while caressing the nightie with my left, and I spent a lot of time looking at a picture of Allison in school uniform, with her stiff cock in her hand.

My face was getting warmer, and I was embarrassed, beginning to realise how Alan started his journey. I’d be okay though because this was simply to prove a point to myself. I would enjoy a wank dressed like this, looking at the picture of Allison, and that would be the end of my experiment. I was a normal guy, so this would be a one-time thing, with no long-term effect.

I compelled myself to ignore one simple fact. The true story of Alan becoming Allison had captured my imagination, because many times over recent months, I’d fantasised about wearing something feminine. I had wrapped my cock in knickers or tights a few times in the past to have a wank, but I’d only dreamt of dressing in delicate lingerie to fuck my fist.

***