© Copyright 2017 - Rubric_Charm - Used by permission
Storycodes: Solo-M; MM; cd; silk; camisole; nylons; dancewear; mast; climax; cons; X
This is a fantasy fiction that I ran over in my mind when I was a younger guy (and still to this day) - it is based in a core of true experiences, but most of the best stuff never happened to me... This is what I consider may have happened had I made some different choices, or life had taken a different turn. To be posted in parts: this section is mostly introductory, and the best parts come a little later (two more are currently written). I hope you enjoy!
* * *
A series of poor choices had bought me here.
Door canvassing... I couldn't imagine a worse job to be doing in that moment. School hadn't worked out for me, and here I was, just turned eighteen, trying desperately to find a job that I could cope with.
At first, this has sounded like it might be okay... I wasn't (technically) selling anything, and the pitch we'd been taught made it sound like we were doing the homeowner a favour. But it was horrible: horrible in that way that could only be understood by trying it out.
I had always been awkward around people at the best of times. When those people were clearly annoyed by you encroaching on their time, that was even worse. Most of them were polite on the surface, but it never went well. Most of the time I simply hoped that no one would answer.
But Martin was different... He seemed interested. He'd offered for me to come in. We weren't supposed to do that, and I told him as much, stuttering out the phrase.
He lingered with me... I found it hard to believe that he'd wanted to have his house looked over for cracks so that the company that had sent me out could one day sell him a special weatherproof coating. My thoughts started to drift.
This was only my second day trying to do this, and I knew that it would never work for me. I found my supervisor, out making the same rounds in another street and handed back my clipboard. I couldn't do this, and made my way home.
But Martin stuck with me. And I knew where he lived.
The following day, I was, of course, unemployed again. I lived within walking distance of Martin's house, and walked nervously back there.
I wasn't gay. I'd convinced myself firmly of that. I was just enjoying some things that, at the time, I assumed only gay men would enjoy.
Being the shy sort, I'd not had a lot of luck with girls, and had never had a relationship get to the point where anything sexual might have happened. But I had some specific interests: it had started a few years earlier. Finding a lingerie catalogue at home had fascinated me: the different shapes, styles, materials... and the women wearing them, being models, all looked amazing. I was hooked: not so much on the women, but on what they were wearing. I wanted to know they felt: how wearing such amazing underwear would sit against my skin; looking as incredible as they did; being dressed in clothes designed, purely and specifically, to arouse men. I had to try some.
My mum and her partner were out at least two evenings a week. They didn't leave me in the house alone at that age, and, beside my two sisters, we'd have another relative sit in with us. They knew my introverted ways though, and left me to my own space. I had a chance one of these nights: I was upstairs alone, and snuck into my mum's room, finding her underwear drawers.
I couldn't stop myself from shaking, and hadn't dared to turn the light on. I grabbed at something that felt both silky and lacy, and crept back out and into my own room; safe behind the closed door.
I breathed deeply, and glanced at what I’d swiped: a white silk cami with lace trim. I was hard - I had been for a couple of minutes, as it happened, but had been so nervous that I’d not really noticed until now. I was naked in seconds, and pulling it over my head, laying back on my bed.
It felt wonderful: I ran my hands over my body, savouring the sensation. I hadn’t masturbated before this moment, and didn’t really know what I was doing. I grasped my cock firmly and shook it. It didn’t take long before, breathlessly, I experienced my first ever orgasm, squirting seed all over myself.
More-or-less immediately, I felt the guilt that would become familiar over the coming years. But that was just the first of many times I did that sort of thing: mostly my mum’s underwear, but eventually dresses and, if I could fit myself in them, shoes too. Hosiery of any kind was a favourite: I loved the way that my legs looked and felt in them. Stockings were obviously sexier, but I loved the enclosed feeling of a pair of tights.
As my sisters got older, they became another source, especially as they began to get their own sexy clothes. One of them had a pair of PVC trousers… the other had that Union Jack dress that Geri Halliwell once wore at the Brit Awards (a formative image for pretty much every boy of my generation)... They also had dancewear, and the spandex and lycra leotards and catsuits gave me a similar, yet quite different sensation to the tights that I’d been adoring. I lapped up all the experiences of this stuff that I could.
But, to underline; it was wearing this stuff, and particularly with it being how I began to masturbate, that really formed my early sexuality: Crossdressing would be forever linked to sexual experience for me now.
So, I was confused… Standing near Martin’s house, where I’d lingered for about quarter of an hour trying to sum up the courage to approach his door. I didn’t even know his name at the time. I had no idea what he would or wouldn’t be interested in doing with me: all I knew was that he paid me far more attention than he should have, and was far friendlier than he should have been the previous day.
My mind had raced, and I’d struggled to sleep the night in between. I wasn’t attracted to this guy: we was probably about 50, balding, wore glasses and was slightly larger than average build. I was convinced that I wasn’t interested in men at all, but had spent the past few years secretly sneaking my mum’s and sisters’ clothing out to wear and masturbate with, thinking about how appealing I’d be to men, eventually getting some clothing of my own. I loved how I looked when I dressed up. I was slim, but with nice, shapely legs, and a rounded bum. I’d grown my hair out long, and often shaved my legs, groin and chest in an attempt to look more feminine.
I’d wondered several times about what this meant about my sexuality. I’ve learned in the years since that men of all sexualities like to dress: but at that time, it was a dirty, taboo thing, that I was convinced only gay men would do. I was confused, and rode a constant cycle of pleasure and guilt.
I didn’t think I wanted him… I think I wanted him to want me: he’d shown interest, and I wanted to know what it was.
I knocked. He answered.
“Err…” I began, gently shaking.
“You were here yesterday, is that right?” he asked. He smiled a friendly smile: the same one as yesterday that made me think there was more.
“That’s right…” I answered. “I don’t have that job any more though; I couldn’t do it,” I explained.
“Want to come in and tell me about it?” he offered. I smiled with acceptance, followed him inside, and gratefully accepted his offer of tea.
Martin was lonely, it turned out. He had friends, and he had family, but he was living alone, and missed others in the house.
“My wife died about four years ago,” he explained. I adopted a sympathetic face, but in truth, I’m not very good in this sort of situation. “I feel like I’ve been coming to terms with it…” he continued, “but we were married for twenty three years; would have been twenty seven last month. It’s a lot to adjust to.”
“I’m sure it must be,” I replied sadly. I really had no idea what I was doing here, or where this was going.
“My daughter has been wonderful since her mother died,” he continued. “She was fifteen at the time, but faced it with amazing maturity. She helped me through a time where… I don’t know… perhaps I should have been there more for her?”
“We…” I began, “we all deal with things differently, I imagine.” He nodded and smiled.
“I think you’re right,” he answered.
“So, where is your daughter now?” I asked. I was beginning to relax, and was finding it easier to talk to this man, who was simply being friendly and enjoying the company.
“Cardiff,” he answered. “She started university there this year, moved up there two weeks ago.”
“Oh… and she’s your only child?” I asked.
“Yes… we never really wanted more than one,” he chuckled. “She was quite a handful when she was younger; I think that’s why I was so surprised with how well she dealt with Barbara’s death… It changed her,” he shrugged.
“She’d be about your age,” he added suddenly after a short pause. “I don’t suppose you know a Hannah Turner?”
“No, I don’t,” I answered. I didn’t. There were several schools in our town, and the only girls I’d ever known were at mine.
“She’s…” he began, shifting uncomfortably. “Well… she’s wonderful. Very beautiful; looks a lot like her mother at that age.” I probably blushed or something at that point. He laughed gently and told me not to worry. I really had no idea what he was getting at.
“Do you have a girlfriend?” he asked. I filled him in on the situation with my shyness, and how difficult I’d found it to get to know girls, or make my feelings known. He understood.
“Exactly how I was until I was about twenty,” he explained. “In the end, I just got to know Barbara as a really good friend… I wanted more from the start though. When I eventually told her, I was a nervous wreck... but it turned out that we’d both felt the same the whole time!” I smiled and laughed with him.
“So... “ he continued. “You haven’t yet… you know,” he said with a wink. I shook my head shyly. “You have something to look forward to there…” he grinned.
I wasn’t feeling like this was going the way I’d hoped. Martin was a very nice bloke, who’d simply been feeling a bit lonely and wanted a chat. Perhaps nothing to it afterall…
But I popped in a couple more times over the next week or so. We’d got to know each other a bit more each time, and the third time I visited him, something more did happen…
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