What Was Your Strangest Sexual Encounter?

[deepthroat]

I thought I'd suggest this as a thread topic, and see if it gets any interest.

Tell us about the strangest sexual escapade you can remember. Doesn't have to be about Thailand or ladyboys. Whatever comes to mind, if it's fit to type you can share it here.

Ground rules are easy: it has to be your own story, and keep it to one anecdote per reply. If you've got a dozen stories all competing for the title of "strangest sexual encounter I've ever had" post them in separate replies.

[deepthroat]

The first story that springs to mind was the Friday night back in about 1980 or 1981. It's around 10pm, and I'm buying smokes at a 7-11 out in Lynwood (a northern suburb of Seattle). As I'm walking out of the store, I hear the pay phone in the parking lot ringing. I mosied over and answered it, and it's a teen girl. She asks a few questions - how old am I? Am I cool? She says she lives in the trailer court up the street, she has a friend over spending the night and is bored, and wants to know if I want to come by and get them stoned.

Well, it just so happens I have some hemp burning a hole in my pocket, so I said that might be possible, but wanted to know what's in it for me. "Will you fuck me if I come over and get you stoned?" I believe was the understated and cultured way I phrased the question. She agreed. The kicker though is her Mom is out in the living room watching tv, so I have to quietly sneak around to the back of the trailer, where her bedroom is, and climb in the window. Being 19 or 20 and fit, I figured I could pull this off.

With her detailed directions to her specific trailer home, I head to the trailer court about 1/2 mile up the street. I find her "house" and in moments I've scurried up into the window and, true to her word, it's her and her 17 year old friend in the bedroom in sleeping bags. (I assume 17 for sake of legality only - I was 19 but felt quite a bit older, and I didn't check ID). We burned one, then the girl said to climb in her bag with her. I asked about her friend and she (the friend) said "No, I'm fine... go ahead" and just sorta turned away while the two of us went at it. No foreplay; no protection. The deed was done in minutes, which is fantastic because just as I'm climaxing, there's a pounding at the door. Her mom is bellowing from the hallway that she know's they have a boy in there, blah blah blah.

I shot back out of that trailer window liked I'd been fired from a cannon. Made no pretense of being quiet about it either.

I've wondered many a time whether there's a little Deepthroat Jr. running around as a result of that story.

More to come later - you show me yours, I'll show you mine.

[duke007]

[quote name='deepthroat' timestamp='1320718273' post='1

- you show me yours, I'll show you mine.

That comment brings back memories, I said same thing to a girl in the passage at the back of our house.

I think I was about 7 years old at the time

[pdogg]

Have to think about this one; reply will be forthcoming.

Great topic DT!

[williethepimp]

ditto that....a reply will be eventually forthcoming.....great topic DT

EDIT.....FUCK IT,GOT 5 MINS TO SPARE.....HERE GOES...

I have had a few bizarre sexual encounters....the last one was in pattaya when i ended up getting blown and wanked off in an internet shop,by a ladyboy in the middle of the day.....i was the only customer (obviously)....the story is a little more sordid than that...and i will have to spare the details,but i will gladly relate the whole story to you,should we ever meet...i am a very sick man!

[SiamSam]

Indeed you are!!! I knew that from the first time to smiled at me. :)

[pdogg]

Love your tale about trailer trash tail DT!

I think many of our sexual encounters are planned to some degree?

But for my first entry, I'll tell about my chance encounter.

It was Friday night of Labor Day weekend and was looking forward to a weekend of just being alone, not working, and the city being deserted.

It was about 3AM Saturday morning and decided to go down to the corner to mail a letter. Near the corner a girl in her twenties called out to me and we started chatting. She was shitfaced. Her body language was giving me the green light and we started making out. Then she unzipped my fly and started giving head on a NYC side street.

Then I invited her upstairs. I rember her saying, "what turns you on". And maybe if I had had a few beers I may have said ladyboy cock, but I had been home alone all night so we just had regular sex.

Strange as in unexpected. If I walked down that street every night for the rest of my life I would probably never get head by the mailbox again.

I don't think she had a particular interest in older guys but rather she was pom pui mak mak and just takes what she can get.

[KenW]

I don't know whether this qualifies, for it's the strangest non-sexual encounter.

I first put it up here on the forum in my Love at First Sight adventure from my Vietnam LBs thread - but most FMs won't have read it there, and any who have will have forgotten it, so here goes again.

Around small lanes and alleys in Little India, Singapore, such as Hindoo St, there are brothels (or were anyhow, not sure if they’re still legit as of 2011) populated by LBs (I met a gorgeous one from Malaysia) and by subcontinental hijras (the ones Professor Serena Nanda called “neither man nor woman” in her book of the same title).

My first hitup at one of these was simply an unmarked doorway, plain wooden door open, behind which there was a steep staircase. The action took place upstairs, and I thought well, I wonder what might befall me up there? Stairway to Heaven? I doubt it, especially if one of those 40 year old hijras gets you in a deathlock.

In the doorway lounged two hijras, old, ugly, fat (same as me) with this gorgeous 22 year old Malaysian LB standing a metre apart from them, on the footpath. I chatted and flirted a bit, but it being so early, I told them I needed to eat and have some strong drink, after which I would return.

I hoped my wink to the Malaysian would be interpreted as something like: wait for me.

I walked a couple of blocks to an Indian eatery I wanted to sample, had a superb meal, with a couple of carafes of red, after which I was ready to go wandering again.

In one of the lanes near Hindoo St – a rabbit warren of door to door brothels, ground floor, all open, whores lounging like buxom bunnies on divans and settees, but as far as I could tell, only populated by GG types, many of whom were old hags, literally, like some of those you find in the beer bars on Second Rd, Pattaya, the white roots of their bottle dyed hair showing through at the parting – I bumped into a chap, when I was too busy, like a Jabiru exploring a marsh pond, craning my stickybeaking neck at all these sights. Though he didn’t look all that much like a fellow traveler, it was immediately obvious from his body language he was, and hoping I was, he sent out several unspoken signals, following which I nodded.

He took off, walking quite fast up the alley, looking back over his shoulder, like a scoutmaster with a trailing troop of initiates, presumably leading me to a site for satisfaction. In fact before we got to the end of the alley he had to stop and wait for me to catch up. When I got to within about three metres of him he took off again.

When I reached the footpath of the big drag Serangoon Rd I drew breath. There he was again, pretending to look over the goods of a street vendor. He looked up, making eye contact with me. As soon as I got to within touching distance, he off once more, plunging into the traffic as if determined to die right there and then.

A shaggy dog slipped onto the roadway as though shadowing the scoutmaster.

If I wanted to be part of this I had to do likewise. Perhaps a red light would part the rollercoaster of cars trucks and vans like Moses parted the Red Sea. It didn’t. I held my breath and stepped off the kerb into six lanes of terrifying Formula 1 lunatics going a thousand miles an hour.

I lived. (Vietnam has some redeeming features: at least it’s taught me to cope with serious mayhem on the roads.)

This scoutmaster’s trek went on for several blocks on the other side of Serangoon, down alleys, up alleys, round corners, there he would be waiting me. Then taking off. I kept checking over my shoulder for his accomplices. Be prepared. But there were none in sight.

In each dark spot I stared hard at the small groups of men staring hard at me from behind the glowing tips of cigarettes, their eyes bulging white like Murali about to deliver his doosra.

He had me going for fully 45 minutes this guy, after which I was in a lather of sweat, getting impatient, wondering why he had not led me to any open doors, to any mini hotels, to any house, to the glans of his cock. Then the next leg of following had me suddenly in this crowd of about two thousand subcontinentals all baying and braying, as they sought instructions for, directions about, bus departures. It was like being outside Eden Gardens; I waited for some tout to try to sell me a ticket. This was a huge open block from where long distance buses came and went, a terminal of sorts. Were we bound for Bangladesh?

My sex partner had disappeared. I wandered the parking lot between buses, through throngs, hoping he would find me even if I couldn’t find him. But like an unobserved quantum object he had completely vanished.

I wandered back down Serangoon.

What had that been all about?

It was certainly not about sex. Was he just setting me up for robbery? If so, he had ample chance in various dark alleys we walked. Among the various groups of men hanging about could have been his henchmen. No-one bothered me.

Did he genuinely lose me? I doubt it. He had waited for me at every corner and turn, or when in thick crowds I lagged behind. For most of the time I had the only white skin in sight, so hard to lose.

Was he just taking the piss out of the dumb Caucasian? Being a prick teaser in the real sense of those words. Probably. Silly me. I headed back down to Hindoo singing Ah caint get no.

[deepthroat]

interesting story Ken. I don't think I would have followed, but something apparently piqued your interest!

PD, loved the story. I've got others like that as well - there's nothing quite so fun as the unexpected strange. And when they're into kinky too - WOW!

More to follow.

[SiamSam]

Speaking of interesting and kinky encounters, I met DT in Vancouver not too long ago. Hmmmm, anyone interested in that cliffhanger? :)

[deepthroat]

I hope you at least bought him a drink.