The summer before I went to university was hot. Really hot. It barely rained for weeks and when it did, it came down in torrential downpours. The air would get heavy during the course of the hot humid mornings and by lunchtime the clouds would darken and you could feel that it was going to be getting very wet, very soon.
The day I first met Jenny and James I’d been into town in the morning, had a look in the record shops (this was when you’d still find the big chains on the high street, along with a couple of independents), and just wandered about doing a bit of window shopping. Obviously, that meant slowing down to stare in the windows of the women’s clothes and shoe shops and taking the circuitous route through the make-up counters in the department stores.
I had turned nineteen in early summer and by then I’d already experimented a bit with dressing up. It had started, like many other CDs seem to do, by getting access to my sisters’ underwear a couple of years earlier. I was young and horny. All the time. I couldn’t watch TV without getting hard, let alone think about girls in my class or ones I saw in magazines. All I could think about was having sex, which was a joke, because I couldn’t bring myself to say anything to most girls my age, let alone try to chat them up. That left me spending a lot of time masturbating and reading porn.
As I read and wanked more, the more I started to think about what it would be like to not just fuck the girls, but be the one being fucked. From that point my ‘personal time’ fantasies evolved quickly. Not only would I read porn and wank, but I started to use moisturiser to make the long slow strokes I loved more pleasurable.
From there I progressed to baby oil, and I’d adore coating my cock and balls making them smooth and slippy. As I fantasised about whichever gorgeous beauty was that month’s playmate, my oily fingers would start to wander and before long they were dipping in and around my anus, imagining what it would be like for me to be penetrated like the girls in the stories. My god! What a sensation.
I still remember the first time I massaged my hole, before slipping one, then two fingers in. It didn't take me long to cum from this new feeling. Or to get hard again and go another round. I was a horny teenager after all.
Once I’d started to penetrate myself with my fingers, I was soon douching as part of my daily routine. From there it was only a matter of time before I started using handy objects to pleasure myself with. A bar from a weights set was always cool to the touch, but had some delicious contouring that I could feel as it eased inside. The handle of my cricket bat was long and had a good girth and the rubberised texture was lovely as I sucked it into my tight, puckered, lubed hole.
The orgasms I had with those, when I was freshly showered, cleansed inside and out and all slicked up were just the best. Sometimes I’d kneel down and put the handle at the entrance to my arsehole. As I sat backwards, it would first meet resistance from my star, but that would soon give way as I pushed harder, sliding down on it and imagining it to be a real cock inside me. I loved this position because I could control the pace, sliding up and down, putting more or less pressure on my prostate as I held the bat in place with one hand and wanked myself senseless with the other. Sometimes I barely needed to touch my own cock, the shaft being in just the right place to massage my prostrate and tip me over the edge, sending my spunk spurting through the air.
Or I’d lie on my back, knees up on my chest, feeding the length into me, imagining I was being pounded by some faceless man. In this position it was harder to use my hands to bring me off, but the feeling of being spread wide open was fantastic. When I did cum, it would be so forceful that I’d give myself a facial, my straining cock covering me in my own spunk.
That’s when I first tasted spunk, having inadvertently delivered a load into my own mouth. Although shocked, I still managed to swirl that first dose round my mouth, getting used to the taste and eventually swallowing it down. From that day onward, I’d rarely waste my load, taking it down or massaging it into my body and anus as part of my post-coital come down.
With all this self-pleasuring bum fun going on and the fantasy of being the girl in the mag developing nicely, the next step was to start dressing the part. My sister had already gone away to uni and had landed a summer job down there, but had left some clothes behind, and I would raid her wardrobe.
I’m much taller than her, but back then I was quite slender and could just about squeeze into some of her outfits. Knickers were the first thing to go on – the elastic being forgiving as they eased over my calves, thighs and finally my buns. I loved the g-strings the most. The lace thong tickling my hole, while offering just enough at the front to hide my package. Of course I could barely contain myself most of the time, with my erect penis standing proudly above the panty line. But when I was flaccid I used to love the shape they gave me.
Stockings and suspenders were a must. I still can’t think of anything more erotic. I love the way they feel, the sheer silk encasing my legs, and the framing effect makes sure that the eyes are drawn to the crotch. Which is kind of the point, after all!
Shoes were a problem. My sisters’ were two sizes too small for me, but for some reason she did have one pair of heels which I could just about squeeze into. They were black patent, with a three-inch heel which I could barely stand in, let along walk in, but I tried all the same and gradually got better at it. I loved the look of my legs and how the extra height from the heels made my butt stick out a little more curvaceously. I’m five foot ten inches, so with the heels on, I was an Amazon.
Knickers, stockings, heels were great, but my sister’s bras, no matter how hard I tried, never quite fit. She was just too slim. But I could get away with some of her baggier blouses and stretch skirts. Because I was taller and bigger than her, the fit was snug to say the least. My sister was fairly flat chested, being a B cup, so most of the clothes didn’t gape too much. The skirts especially were smaller, turning minis into micros and showing off the tops of my stockings. Not that I minded – seeing those lacey high tops reflected back to me in the mirror just made me hornier.
And of course there were a couple of dresses I could wear. My favourite was a black cocktail dress with a high lycra mix and a plunging neckline, so it stretched beautifully over my body.
Finishing off the look obviously needed a little make up and over the course of a year or so I practiced enough to be able to look a bit better than a typical man in drag. Actually, to be honest, when I’d gone to work on myself, I thought I looked pretty damned hot.
This had all developed over about two years. I was maybe seventeen the first time I sneaked into my sisters clothes and no older than eighteen when I first started fucking my arse.
By that summer then, with both my parents working full time and my sister away from home, I could spend most of the days during the week pampering and pleasuring myself without fear of getting caught, and by god did I go to work on myself. I don’t know what it is about being a teenager but my sex drive was through the roof. After I’d finished my A-Levels I was pretty much just waiting to go off to uni. I had no summer job and a lot of my friends had gone off traveling. So it was just me, my porn collection and my filthy mind keeping me occupied.
I was careful never to get too careless. My parents left the house by 8AM, so I wouldn’t start any monkey business until 09:30 at the earliest. And I always made sure I was done by 1500. The last thing I wanted was a parental unexpectedly coming in whilst I was licking cum off my heels with a cucumber sliding out of my arse. That would be a hard one to explain away.
I did however, start to get a bit cockier about wearing my sister’s clothes in public. I’d regularly sunbathe in our sunny, but private back garden wearing heels, bikini bottoms and broad rimmed sun hat. A couple of times I even brought myself off, using the sun lotion as a lube on my cock and hole. The first time I’d taken an ice pop from the freezer and some of the ice had dripped down my chin onto my chest. I found the freezing sensation really erotic and used the rest of the pop on my nipples, making them rock hard to the touch. After that I had to finish the job off, with the warm jets of spunk splashing on to my tummy a really contrast to my frosty nipples!
And it also became the norm for me to wander into town dressed in my boy clothes, but wearing lingerie under my jeans.
Which brings me back to that hot, hot, humid summers day when I’d been into town, secretly lusted after the latest girl’s fashions, got drenched in a full-on torrential summer storm and found that I’d managed to lock myself out of the house.
