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.
"Can I try?" Andy asked, pushing my head gently but firmly away.
"Yes, if you like," I said, trying to hide my disappointment, and stood up as he took his turn on his knees.
"You'll have to give me directions," he said, lifting my skirt and pulling my cock and balls out through one of the leg holes of the panties. "I've never done this before."
"OK, just kind of lick it a bit first and then suck it while rolling your tongue around the head, careful not to use your teeth... Just do what comes naturally really."
He followed my instructions, and proved a good student, soon bringing my semi-erection to a full one, and from the sounds he made, enjoying it a great deal. Once more I imagined what any nosey neighbours would make of what they would see through the window: a thirty-year-old guy with his head up the skirt of a rather masculine-featured school girl. Or more likely: a thirty-year-old guy sucking the cock of a hairy-legged, clean-shaven 22-year-old dressed in a school girl uniform. However, the theoretical voyeurs would not have long to watch this, as I soon realised that not having a wank that morning had been a mistake, for now after only two minutes of having my cock sucked I was on the verge of ejaculation, far earlier than I wanted. Reacting swiftly, I pushed him away.
"Shall we go upstairs?" I suggested, hoping the pressure would subside. To my relief, he consented, and taking the camera he had put aside when giving me a blowjob, we went up to my room. Immediately, he began stripping off, but I was reluctant to get out of clothes that made me feel so sexy, so I just took off the knickers and unbuttoned the shirt.
"Can we try a sixty-nine?" Andy asked, standing before me completely naked.
"Sure," I replied, at once eager to try this as I had only done it once before with the first guy I ever slept with, and nervous that this might bring me over the edge too soon.
He lay down on the bed, his head on the pillow, and I mounted him, my skirt hanging down so I couldn't see his face then got down on my elbows, facing the full-length mirror on my wardrobe opposite the foot of the bed. This way I could watch myself take his cock in my mouth, the shaft disappearing between my lips until I could feel the tip on the back of my throat, then out it came again, sliding over my tongue, shiny and wet from my saliva. Concentrating on watching my own head suck cock between his long legs and dribble down on to his shaven balls distracted me for a while from the hot wet tongue swirling around my own dick, but this effect didn't last for long, and I had to really strain myself so as not to cum. It became too much, so I knelt up and got off as fast as I could without ripping my cock out of his mouth.
"Did you bring condoms and lube?" I asked in a rush. "I need to you to fuck me, now!"
"Oh, yes," Andy scrambled for his trousers, pulling out a condom and small container, handing the latter to me.
While he got the rubber on, I bunched my skirt up in my left hand to keep it off my arse and used the other hand to scoop liberal amounts of lubricant from the container to spread first around my sphincter, allowing my fingers to slip in a little, then over his throbbing, latex coated erection. Placing the container on the floor, I turned my back on Andy, who was now sat on the edge of the bed, and reversed between his legs, still holding the skirt up and my right hand still on his cock as, looking in the wardrobe mirror as I did so, I lowered myself down on to his shaft.
I was no virgin to anal sex, but neither had I ever had it on a regular enough basis to loosen me up significantly, particularly in the few weeks preceding this session, so although he entered smoothly the first time, it was nevertheless a very tight fit, particularly as he seemed a little thicker than what I was used to. To begin with it was even a little painful, but it felt so good to be filled up there that I could ignore it, and after lifting up and down a few times it soon subsided completely.
I released both his cock and the skirt so as to steady myself on his knees either side of me, with the added bonus of hiding my erect cock from view in the mirror that now showed a school girl clearly enjoying impaling her arse on a big throbbing cock. As always, though I felt I was getting better and lasting longer, this position used muscles that did not often get used, tiring sooner than I would have wanted as a result.
Not even bothering to explain this time, I simply stood up slowly, letting him slide out of me, then got on the bed on hands and knees, facing the mirror to satisfy my voyeuristic-exhibitionist streak. Cottoning on immediately, Andy got up behind me, positioning his cock at my arse hole and pushing in, pulling me towards him with his hands on my hips as he did so, entering me easily. I simply left him to fuck me, pushing back to meet his thrusts but otherwise doing nothing other than enjoying the feeling of a dick pushing in a out of my sphincter, pressing against my prostate so that my own cock leaked precum all over the underside of my skirt each time it swung and came into contact with it.
My mind was also treated to the delightful view I had of, depending on how I wanted to view it, either me or a short haired schoolgirl, her shirt open to show her bra, being sodomised. Both our faces were becoming flushed and contorted, he was grunting with each thrust while I was breathing heavily and letting out little, slightly feminine moans to play the part of the school girl. It felt so good that I thought if he continued for another five or ten minutes I might actually get an orgasm just from the anal stimulation, so I resisted the urge to do as I often did and turn over on to my back to wank at the same time.
However, it seemed that I was not the only one ready to cum, as just as I was thinking this Andy announced he was cumming, slamming his cock deep inside me one last time and keeping it there, his reflection showing his eyes closed and mouth wide open, gasping. Doing my best not to show my disappointment once again, I let him finish inside me, resting my head on the bed as he withdrew and pulled off the condom, then rolled on to my back, undoing the skirt and removing it before spreading myself out before him, hoping that the sight of my hard cock, sticky with precum, would tempt him, or that he was at least a gentleman and would get me off as I had let him fuck me.
It seemed he was, for once he had dealt with the used rubber he didn't hesitate but settled himself on his front between my legs, cramming my dick in his mouth and practicing his new found cock-sucking skills. For a few moments I was disappointed that he didn't stick a couple of fingers up my butt to replace his cock, but watching his face bob hungrily up and down, framed by his long blond hair, I soon forgot this detail, lying back to moan as I felt my long delayed climax finally burst forth, pumping load after load of semen into his eager mouth. Eventually he had sucked me dry, and pulled back smiling.
"Fuck that was good!" was all I could think to say. Once we'd gathered some energy, we began getting dressed, and I asked him: "So, how was your first time with a guy?"
"Great!" he answered, grinning, but slightly embarrassed. "Maybe we could meet again sometime, I want to know what it's like to be fucked in the arse too!"
"Oh, it's fantastic! But I'm going traveling for a while and this is probably the only day I'll have the house to myself, so unless you want to stay this afternoon...?"
"I can't, I have to get back to work."
"I'm sure you can find some other guy, I've met a few from that site."
"Really? I've met quite a few people on there too."
"Who have you met?"
"Oh, I had some great fun a couple of weeks back with a girl off there. What about you?"
"I've met with a few guys, and one couple. I had a few other possible meets that fell through... And hopefully I'll be meeting some people on my trip!"
"It's a great site isn't it?" We had wandered down through the house by now and were at the front door. "Well, I'd better be going. Thanks for this, it was great! And have a good trip, and lots of sex!"
"Hee hee, thanks!" I replied, opening the door for him. "You too, and maybe we can meet up again when I get back."
"Yeah, definitely. OK, bye then!"
"Bye!" I closed the door and leaned against it smiling. Gingerly I reached behind myself and touched my still slight open, aching and sticky arse hole, and sighed, wondering when I would next be able to have a guy fuck me, not knowing how many of my possible meets along my route would be any good. Then with another sigh I set about cleaning up, as the skirt at the very least was going to need a good scrub before my sister got back...
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<a href="https://www.lushstories.com/stories/crossdressing/webmeets-diary-ch-04.aspx">Webmeets Diary Ch. 04</a>