Chapter 1

Introductions

Sunday 5th August, 2007

Dumfries

Scotland

A brief look out of the bedroom window told me it was a glorious day; blue skies and not too hot. Of course, it was only seven o’clock in the morning, but I knew the weather was going to be pleasant all day.

My attic flat was so high above the road I felt I could touch the sky. Sadly, it was the only sense of exhilaration I was feeling. My latest girlfriend had dumped me and though at twenty-seven I should have been happy to go out and hook up with somebody else, I had issues—and I so desperately wanted to deal with them.

I left the bedroom window open before I sauntered into the bathroom to wake my body up for the day ahead. I’d shaved with my electric razor, and was about to step into the shower, but stopped.

‘Go on, Darren,’ I said aloud. ‘You know you want to.’ I lifted out a twin-blade disposable razor and the gel. Ten minutes later, I’d carefully removed all the tiny bristles and light hairs from my chest to my ankles. On a whim, I applied gel on and under my arms and gave them a close shave.

The sensation of the shower gel was incredible as I spread it over the smooth skin of my body, arms, and legs. I felt sexy and couldn’t stop grinning. It was my habit of a regular all-over shave which had first alerted Corinne, but she’d accepted whatever weak excuse I’d given. She let it go and said I wasn’t like other guys she’d dated. Corinne had been my third girlfriend and until she discovered my dark secret I thought she was the most understanding person I’d ever met.

I pulled on my short, silk dressing gown and enjoyed cereal and coffee as I pondered the day ahead. I had two days off work, no girlfriend to think about and I could do what I wanted.

I sat at the small table in the living room, and stared at the screen, willing myself to type the words into the search window, but just like the last few times—it was as if I had no control over my fingers. I sat back and placed my hands on my silky-smooth thighs. I looked at the throbbing bulge between my legs and smiled.

‘This is all your fault,’ I said. The glistening head of my aroused cock stared up at me. It was during that strange moment of talking to my erection that an idea came to mind. I left my desk and took a while to prepare myself.

It took me half an hour to get ready. My long fair hair was neatly centre-parted and hung over the front of my shoulders, held in two pigtails with red ribbons. I’d applied mascara, eye-liner, and lipstick, but I knew it wasn’t great so I wouldn’t be looking too closely at my face. I needed a lot more practise at makeup. I was pleased Corinne had left behind so many cosmetics and some of her nail varnish because I still wasn’t brave enough to go out and buy any.

I’d taken the precaution of ‘borrowing’ a few items of sexy underwear over a period of a few weeks, so that if Corinne did go, I’d have more choices in my secret stash. I had a small collection but now there was a choice of more than one colour or fabric. Okay, I only had one pair of shoes, but at least they were high heels, so I could practise walking in them.

I stood well back and gave myself a sideways glance in the full-length wardrobe mirror. If I didn’t stare, I didn’t look too bad—it was only for my pleasure anyway. As I eyed my reflection up and down I placed my hands on the black lace bra and then ran my fingers down my body to play over the matching panties, before gently caressing the fishnet hold-ups.

If I didn’t move too quickly I wouldn’t fall over, but more disturbing was the bulge in my underwear—it took away the feminine look. I’d read a few short articles on the internet about how to deal with reducing or hiding the bulge, but I still hadn’t got it right. Besides, when I was dressed-up I was too aroused to try to do anything except take myself in hand—the whole point of dressing-up in the first place.

I sashayed through to my small living room and sat at the table again, knees pressed together, as best I could. I reached down and smoothed my hands over my stockinged-thighs and felt a tremor of excitement. I caressed the throbbing bulge in my firm but soft panties and wondered how the hell I was supposed to tuck my shaft anywhere when it was in such a condition.

I checked the clock on my laptop screen and smiled—forty-five minutes to get myself completely ready, but I was already feeling that I could continue beyond the search window this time.

‘Why didn’t I think of it before—doing this when feminised, which would make it feel right?’

I took a deep breath and placed my fingertips on the keyboard. For a moment I had to pause as I straightened my fingers to admire my bright red nails. With a smile on my ruby lips I proceeded to hit the keys.

My trembling hands were making up words which meant nothing. I had to slow down and concentrate. I typed in one key word after another and each time I got long lists of possible links. There had to be a way to get close to what I wanted to try. I didn’t want a ‘contact’ website for gay men—I’d have to be more specific. I sipped my coffee and then played my fingertips over my thighs as I let my mind wander.

‘Crossdressing novice—that might work.’ I typed it into the box and lo and behold a short list of sites dropped down. I read the opening lines for each and then went back to read them again. The fourth one sounded good. I clicked on the link.

‘You must be at least eighteen years … and you agree, blah, blah, blah … prior to any contact.’ I’d taken the precaution of organising a secret email address, just in case I ever had the guts to try this sort of thing. I entered my email and age, and then got a box asking for my username. Damn, I couldn’t use my real name. I looked at the author names of the books on my shelf unit.

‘That’ll do for me—Loretta.’ I typed in my new feminine name. It struck me that as I’d progressed from trying on panties and gradually moved on to wearing several items, I’d never considered giving myself an alias for when I was dressed-up. Of course nobody else was involved, so I didn’t need a name.

‘Oh my God.’ I stared at the topics in the forum. I couldn’t believe I’d finally done it and got myself registered into a site like this one. I spent a few minutes reading comments in each of the topics. There were men of all ages looking to get in touch with other men who shared their interest in crossdressing, and some were quite specific about their wishes. I went off and fixed myself a fresh coffee before settling down to read every comment from the topics which interested me.

‘Still on your own and dressing in secret?’ I stared at the question and saw that there were only four comments. A ‘live chat’ speech bubble opened.

“Hi there—I’m Ramona.”

“Hi, I’m Loretta.” I typed.

Ramona was straight to the point and after the innocent introduction of her name it took about five exchanges and simple questions before she was asking if I wanted to join her and her big friend who had a ‘bit extra’, for a night of discovery and fun. I ditched the chat and stared at the screen as I sipped my coffee. I’d have to be careful.

I scrolled through a few more profiles. Alongside some exotic and pretty ‘girly’ names I was seeing names like Roberta, Phillipa, Denise, Paula, and Nicki. They were nice names, and if I’d met a girl called any of those I’d have been quick to say that it was lovely. However, being on this site, it struck me that some of the members had failed to use much imagination—probably adding a letter  or two to feminise their regular name.

Surely these were just nice adaptations of Robert, Philip, Denis, Paul, and Nick?

Another bubble opened and flashed a few times before steadying. Like my username, the age appeared in brackets after the name. I clicked on the new comment window to accept.

“Hi there—my name is Kirsten. Are you new here, Loretta?”

“Yes.” After my experience with Ramona, the forty-year-old, I was taking this much slower.

“You’ll have to be wary on here. There are a few unscrupulous types who use sites like this to prey on the new members or the naive.”

“Thank you, Kirsten. I’ve only been a member for a few minutes and I think I’ve already met somebody I should avoid.”

Kirsten said she didn’t want to affect my opinion of other members so didn’t offer any names. She said she was still new to the idea of going online in this way, but she’d be happy to chat and help me relax into using the forum. Kirsten said she’d been a member of the site for three weeks, but had yet to find that one person with whom she could open up, or feel at ease.

I explained that I was new to the idea of talking about my secret indulgence and asked why she’d decided to go online the way we were doing—to chat to somebody else. She told me she was looking for a genuine person in a similar situation to talk to, ‘girl to girl’, so to speak. 

By the time I’d chatted with Kirsten for fifteen minutes I was feeling comfortable. Unlike Ramona, Kirsten wasn’t pushy. In the brackets beside her username it said she was thirty-two, so I was pleased to see he/she was only a few years older than me. We discussed what we were wearing as we sat typing our messages to each other and though it felt strange, it felt good to be in touch with somebody who made me feel that I wasn’t doing anything wrong. We ended the chat and agreed to get back on at six in the evening.

Before I left the site I flicked to a few of the short bio pages and the accompanying photos. A few of them looked a bit rough and ready, even dressed in pretty clothes, and wearing makeup, but there were a couple of people who fooled me until I zoomed in on the picture. There was hope for me yet.

When I stood up to leave my laptop I was reminded that my cock was throbbing. I didn’t want to relieve my symptoms yet because I wanted to be in my costume for a while. I had nowhere special to go, so I figured I’d stay dressed all day and see how long I could put off taking myself in hand. Would I make it right through until the evening—I was going to try.

*

I logged in and at one minute past six, Kirsten appeared online.

“Hi, Loretta—how are you?”

“Hello again, Kirsten. I’m good, thank you.”

We chatted casually like we had earlier and discussed what we were wearing and which fabrics we liked. It was nice to see satin, silk, nylon, and lace being mentioned by somebody else, and gave me the impression we had similar taste. I admitted I didn’t have much of a secret stash, or ‘wardrobe’ as she referred to her collection.

Kirsten admitted that for her it wasn’t about wanting to be a woman—it was a fetish thing, and being dressed turned her on. I was happy to say that I was the same and had no interest in changing my body. I wasn’t dysmorphic or whatever the condition was called. I felt so at ease, when the question came I simply responded.

“So, Loretta, if you’ve been dressed all day as you’ve said, have you been able to avoid playing with yourself?”

“I have, but it’s been difficult.”

“I’d like to ask something, but you don’t have to answer.”

“Go ahead. I don’t think we can do each other any harm on here.”

“Do you tuck, or use a gaffe?”

“I’ve read about using a gaffe. I don’t think I’d like the idea because it would feel like an extra piece of clothing to remind me who I really am. Apart from that, I don’t fancy using tape to hold myself in place.”

“What about tucking?”

 “I tried the tucking thing but find it difficult.”

“Maybe sometime I’ll give you a few tips if you’re happy to stay in touch.”

“Thank you, Kirsten. I’d appreciate any advice, because as I said earlier, I really am a bit of a novice.”

“I’ll be signing-off now, and I’ll meet you on here in two days if you like—same time in the evening if that’s okay?”

“Okay, that sounds good. I know we don’t owe each other any explanations or promises, but though I’ve only chatted to you a couple of times, it’s been nice.”

“It might give your confidence a boost to know that you’re the first person to whom I’ve actually enjoyed chatting, and I’ve tried quite a few—I almost gave up the online friend idea.”

 “Thank you, and that does help my confidence.”

“Goodnight. Kirsten. xx”

“Goodnight, Loretta. xx” I’d added the two kisses without thinking.

I left the site and switched off my laptop. When I stood up I didn’t have a throbbing hard-on—this was my chance. I quickly squatted and reached inside my underwear to push my bits down and back between my thighs. As soon as I’d managed it I clamped my thighs together before I became aroused. While I had some control, I eased my panties up and tugged them tight to hold my cock in place, forced back toward my buttocks. My balls were prominent but squashed at the front.

‘I’ve done it—I’ve finally tucked myself back. Wow.’ Even as I said the words and stood up straight I could feel my cock begin to throb and there was a warmth as my shaft was squeezed between my thighs. It was a very pleasant warmth. I had the urge to jerk my hips back and forward. ‘Mmm.’ I went for a slow stroll around my flat, wondering what Kirsten might look like.

***