Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.
As I neared the end of my university course I had less and less time for playing around on adult personals sites, and spent most of my free time planning my journey I would be going on once I'd finished. Exams out of the way though, I suddenly had a few weeks of free browsing time, but instead of arranging immediate meets I decided I would see if there was anyone in the countries I was going to, as there I thought I would be less nervous with no chance of people I know learning of my meetings, and also because for many years I had fantasized about sex with Asian girls, and China seemed like a good place to find them!
So I paid the minimum I could to be able to contact people and set about searching for people on my route and contacting those who interested me. I was not too blatant in my intentions, as I knew women needed to be approached differently to men, and there was also the thought at the back of my mind that maybe some of these could become more than a brief physical encounter. I even devised a kind of hierarchy of who I contacted, with at the top women under 26 who seemed to be looking for romance and who came across in their profiles as people I might actually fall for, then women who were explicitly just after sex, followed by couples of any age with a bi male, apparently heterosexual couples looking for men, gay couples and finally transgender people.
Apart from the latter who almost all seemed to be escorts, I got a reasonable amount of responses, gaining several pen pals who I still talk to on MSN, and a few prospective meets. All this may sound a bit obsessive, and I guess it was a bit, but I was still very horny most of the time and wanted more experiences with women and couples most of all, and this seemed a good way to raise my chances of getting them while traveling.
A week after I returned to my family home though, I found I had a few days alone with both my sister and parents away for a few days. Normally I would have used this opportunity to dress up in my girlie clothes and play with my toys (a 2 inch thick, 12 inch long jelly dildo, and a ribbed vibrating butt plug that was about 4 inches at it's thickest, though I never managed to get it in that far), but perhaps rather wastefully I had thrown all these in the bin before coming home so they wouldn't be found by parents "tidying" my bedroom while I was out exploring the world.
Instead I had my sister's clothes to satisfy my crossdressing fetish as I had always done before buying my own, and I guess I could have just warmed up a cucumber in the microwave as a dildo, but I realised that I had another option. For quite a few months I had been in touch with a guy in a nearby town called Andy through the personals site who wanted to explore his bi side, but until now we hadn't managed to meet as I had no means of transport when I was at home, he was too far away when I was at university, and neither of us could host.
I had his phone number though, so one morning I sent him a text message along the lines of "hey, r u free today? i wanna suck ur cock and have you fuck my brains out." Luckily he responded positively as he was not far away on a trip for work after which he would be free, so we exchanged a few more messages giving him directions and telling him to bring some condoms and lubricant as I had thrown mine out with everything else.
I had about an hour before he would get here though, so I decided to shave, although only my face as I didn't have the time or patience to do my legs and pubes. From our previous emails and messages I knew he liked crossdressing, so next I went into my sister's room to pick out an outfit. Luckily she isn't much smaller than me, so I wouldn't be noticeably stretching her clothes.
I considered quite a few combinations, but as I turned to leave and try them on, a pile of old clothes in the corner, some of which looked familiar, caught my eye. Going closer, I saw that it was exactly what I should wear: her old school uniform. Just seeing the pink and white stripes of the shirt and the grey skirt had my penis twitching from the memories of my fantasies I'd had at school.
For the next quarter of an hour I enjoyed myself roaming the house dressed as a school girl, wearing one of my sister's bras padded out with rolled up socks to give me a bust, some of her knickers with small pictures of teddy bears on them (that I got out of the dirty clothes pile in case I got any cum on them) and some knee high white socks.
My fun was interrupted by the doorbell, sending my heart racing. Carefully I peeked out the window, and to my relief it was Andy, who I recognised from the photos he'd sent me, and let him in quickly, paranoid that someone I knew would see and tell my parents. Despite being over 6 foot tall, at least eight years older than me, and from what I could tell under his white work shirt, had a pretty toned body, he seemed pretty nervous.
"Would you like a drink?" I offered him, breaking the awkward silence.
"Just some water thanks," he replied, and followed me into the kitchen. My mouth had gone rather dry, despite me being the teacher for this encounter, so I poured two glasses. Once he'd gulped down some water, he smiled, a very good-looking smile I must say, from behind the curtains of his long, shoulder-length blond hair. "You look really sexy by the way. Where did you get the outfit?"
"It's my sister's," I replied. "She doesn't have to wear it anymore, but we still have to be careful not to get it dirty. I'm afraid I don't think we have anything in your size..."
"That's OK." He finished his water.
"Shall we go into the lounge?" I asked when he remained silent, reminding me very much of my first few meets, and I was surprised to find that I'd grown a little more confident.
"Good idea." We went in and stood by the coffee table where I had placed my camera with which he would take photos throughout our encounter, looking at each other for a moment. "You really do look gorgeous, Jack." I smiled, moving closer. "Can I kiss you?"
By way of answer, I tilted my head up and wrapped my arms around him, pulling him towards me. Our tongues met in a long kiss, getting more and more passionate, and eager for some action I began undoing his shirt to touch his chest that was as firmly muscled as I had guessed, then further down to feel his crotch through his trousers. Growing tired of having to look up so much to kiss him, I moved my lips to his tanned chest, and moved down while my fingers fumbled with his fly.
In no time, I was kneeling in front of him, his trousers and underpants around his ankles, his semi-erect cock in my hands, and his shaved balls in my mouth. They felt good in there, my tongue running over them gently, tasting the salt of his sweat while my hand pulled his foreskin back and forth, his penis engorging itself rapidly.
My licking moved up, teasing his shaft, but it was also teasing me as I was hungry for his cock that continued to grow, slightly bigger than mine at over seven inches and looking bigger because of the lack of hair around it. The head was a bit longer in proportion to the rest of it than those I had had so far, so I spent a while exploring the new shape with my tongue before opening my mouth and taking it inside. My own was growing too in the confines of my sister's knickers, gaining an extra jolt when I glanced to the side and realised that I hadn't shut the curtains.
We were set a bit back from the road, and there were plants obscuring the window to an extent, but even so it would be fairly easy for passers-by to see us if they chose to look through, and the thought of what they would see really turned me on: a short-haired school girl giving head to a thirty-year-old. I decided not to tell him in case he wasn't so keen on the idea. Really getting into this role, my thoughts of getting fucked began to slip further to the back of my mind to be replaced by hopes that he would cum in my mouth and all over my face, but it was not to be.
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