Webmeets Diary : Chapter 04
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Note to the reader: The content of these diary entries is as varied as my
sexuality - if you don't like this one, you might like others, and vice versa.
Read also chapter 1,
chapter 2 and
chapter 3 of this story.
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!"
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"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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