Share Your Unexpected Sex Stories

Well, not immediate sex, but when I was an overseas student in the UK, my friends and I used to hitchhike all over the place. Once hitchhiking by myself on the M4 from Wales to London, I got picked up by a guy in a convertible. He was a bear, just my type. We hit it off but I was on my way to Canterbury to visit friends for the weekend (caught the train from London). He said he'd pick me up and give me a ride back to Wales, so we decided which train I'd take back so we could meet. He even helped me get a train ticket to Canterbury and upgraded me to First Class (very sweet, I thought).

I wasn't sure if he'd be there when I got back after the weekend, but there he was waiting for me on the platform. He drove me back to Wales, came to my room (luckily a single), and fucked my brains out (four times in an overnighter). I was not that experienced at that point, so having sex with someone I hardly knew was a new experience. We saw each other for a few weeks after that, but ultimately he just liked to fuck around and wasn't looking for anything serious, so we went our separate ways. At first I was hurt, but in the end I was fine with it. His cock wasn't the biggest, and after I got more experience, I realized he wasn't a very good top. Hindsight is 20/20!

I'm a lyft driver and I've fucked a couple of passengers so far

My assistant mngr and I were at his desk in the back room. My raging 19 yr old hard on touched his elbow my mistake.

From then on it was constant sex for two years until I moved to another town to finish school.

Im getting a screamer just thinking about it.

Slut bump!

R2 surprise anal?

Met an older man in a movie palace men's smoking lounge and restroom, in the summer if 1966. He wanted me to come back to his hotel, but I had a friend in the theater. We jerked each other off in a stall. Never did anything like that. He taught me what the word "cum" meant. He had a 3-piece suit and wore an eyepatch. Cock was average but uncut.

I was 17.

I still jerk off thinking about him and what we might have done in his room.

i have two stories...one a hot house painter painting my kitchen. His jeans were ripped in the crotch area and leg and he went commando. Saw me staring, pulled his dick through the hole and asked if I'd like a closer look. I sucked him off on the kitchenfloor; he came like a geyser, thick, syrupy ropes of cum.

i also had a handyman cement worker who was very friendly. He wore tattered short shorts, tight and old. He wore a muscle slut shirt. Admiringly, I said, wow you are really built---you must work out. Hegrinned and laughed and asked me for some cold water. I lead him inside to the kitchen and got him the water. He was rubbing his hard on through the shorts. I asked him if he needed any help. He pulled that nice cock out and flopped it around. I was on my knees quicker than (insert name of 00's pop artist--choose one.)

R7 used to direct videos for Nova and Falcon in the late seventies/early eighties.

I was on a flight from my parents' home to mine in Boston in the middle of winter; there was a storm and the flight was cancelled at the last minute. This big, burly bear and I had been chatting at the gate, and when they said they'd put us up in a local hotel and feed us, he asked if I wanted to share a room. I agreed without hesitation. He wanted to go out for drinks so I had to pick the local bar that I thought he'd like, so I took him to a country/western spot, we danced but he then wanted to leave — early flight, eye wink — and when we got back to our room, he fucked me all night. Good top, nice dick, and he knew what he was doing.

When we got back to Boston, his husband met him at Logan and he introduced me as the trick he spent the night with... I was somewhat surprised, and must have turned three shades of red as his husband thought it was hysterical.

[quote]He had a 3-piece suit and wore an eyepatch.

So it's true what that guy's grandma said!

Picked up a hitch hiker years ago and sucked him off. Nice tasting cum.

I was 16 and very much closeted. I was rollerskating home after a long Summer day skating with friends. A handsome, older guy pulls up alongside me and I panicked at first because he caught me off guard and I thought he was just some horny chicken hawk. Turns out he was the father of a couple of neighbors of mine. He'd gone to prison for tax evasion when his wife set him up to get full custody of the 2 kids, clean out the bank account and assets and move with her kids and sister to California.

Hot Dad was about 35ish, shoulder length brown hair and beard. The late 70's Jesus look. That's why I didn't immediately recognize him because of his longer hair and beard. He offers me a ride the rest of the way home and asks me if I'd like to help him do some construction/remodeling on his house so he could sell it and get on with his life. He was offering to pay me for the work (don't even start :-).

So after dropping me off and coming in to meet my parents and ask their permission, I began assisting him. Everything was on the up and up...at first. After laying the cement for the new patio we had more cement on us than on the ground. Before it dried in our hair, he used the backyard hose but it only made things worse. We had to change and things got interesting.

We were changing with our backs to each other but he caught me checking him out. So he didn't bother trying to be discreet anymore. We were only in our socks and underwear at this point. His loaner clothes weren't going to fit me anyway. He walked up to me and began hugging me close and then kissing me. Underwear and socks quickly came off. He took things slowly because I guess he didn't want to scare me off. But he was so good looking and skilled at what he was doing, that I became the more aggressive one.

We were on the floor 69ing each other. Then he asks me have I ever been rimmed before. I told him the truth...no. He licked me from stem to stern in a masterful, take charge kinda way by now. I wasn't going anywhere. He flipped and maneuvered me in ways I never dreamed of. This hot, older guy was making love to me, not a quick, fumbling fuck that I had only experienced to that point.

He asked me if he could fuck me. After his tongue bath had me spontaneous combustion hot, no never crossed my mind. He had a very nice, cut dick. Long, nice girth. He rimmed me some more to lube and loosen me up, and slowly, inch by inch sank that wanger into my tight ass. It hurt at first, I was on my stomach. He turned me to my side and was able to plunge in without too much discomfort for me. He was slow until he felt me getting used to him inside me...then he went to work. He fucked me while I layed on my back, stomach and then he pulled me on top of him, straddling him.

He plowed me deep, thoroughly, and once again later. His gentle, skilled know-how was the best sex encounter I would experience until I would officially come out 10 years later and meet my first LTR BF. Hot Dad continued fucking my brains out for the next 2 months. The work on his house should've only taken about 2-3 weeks. My friends were pissed at me because they lost a skating buddy for the remaining Summer. He sold the house and started a successful business, later moving to Florida. I'm a top now, but would still spread my whorish legs for him today. .Nobody does it like Daddy.

R12^ - He fucked me as I LAID on my back ^

EST thread

Still some hot stuff on here.

R12 Used to write for Penthouse

I was visiting an elderly relative in Florida. I was flying back at a weird time (like 8PM on a Friday) and the terminal was pretty empty. This one guy was looking at me and I thought he was cruising me, but I wasn't sure. He went to the bathroom. I followed and fucked his brains out in the handicap stall.

Years ago I saw this cute hot guy in the university coffee shop. We had instant reaction, talked about two minutes and went to a more private toilet and had wild moments. I never met him again. Had no name nor phone number.

MORE FUDGE daddy MORE FUDGE !!!

Was walking to my hotel room at a conference. I caught a guy's eye in the elevator. He followed me to my room. I was fucking him within 5 minutes

With Dolly Parton.

I was recently in Taos doing research on a book that I hope to publish about Mexicans, when I was weedling away an afternoon at a local antique shop. I was looking at an old pair of leopard print pajamas that, allegedly, belonged to Sybill Jason (aka the skullery girl in "The Little Princess" 1939) when who should traipse in the door but Miss D herself. She was gorgeous, all cotton candy hair and succulent breasts. I couldn't help but fix my gaze on the bounty that was Dolly. She must have caught me staring at her because she sashayed on over in her red cowboy boots and tight Sergio Valenti's and said, "Hi, I'm Dolly!". I responded that, of course, I knew who she was. I told her that she looked amazing for a woman of her age or any age for that matter and she said, "Well, my granny always told me that it's easier to pick cotton with your teeth than to dance a reel with Marshall McCluhan". I agreed. Dolly asked me what I was doing and I told her about the alleged Sybil Jason socks and she said that she was a huge fan of her work. We continued talking for about a half an hour when finally Dolly asked if I would like her to buy the pajamas for me. I told her that she didn't have to, but she said that it would be her pleasure and that she would love to see me try them on. At that moment, I became very excited. My girl mayo flew out of my HAM faster than you can say "I wanna finger fuck a hick singer".

After purchasing the aforementioned pajamas, Dolly and I hopped on the back of her vespa and cruised on over to her hotel, she was staying at the Sheridan Taos North Shore. As I got off the vespa and walked toward the front entrance, Dolly stopped me and informed me that due to her celebrity we would have to go in the back way, I found out not too much later exactly what she meant.

We walked to the back of the hotel by the restaurant dumpster and Dolly peeled herself out of her jeans though she kept her white sweater with the beaded photo of Fred "Rerun" Berry on the whole time. I just stood there, thinking that we were going to go in the back door, but Dolly told me that she really wanted to see my Typhoid Goldfish. So, shrugging my shoulders I pulled off my jodhpurs and showed the goods. But Dolly didn't have too much interest in my downtown lips. Rather she turned me around and started massaging my good old brown eye with her index finger and a plastic cup with the phrase "You wanna get laid? Stick yer head up a chicken's ass and wait" emblazoned across it. Well the next thing I know I am in ecstasy and Dolly is having a good time too, judging by her grunting and groaning to the tune of "Straight Talk" one of her biggest hits and a personal favorite of mine. Apparently, I was having a little too much fun as I didn't seem to notice the stool that started sliding out of my ghetto pucker and all over Dolly's sweater. Soon, I realized I had no control over my bowels and it wasn't just because of Ms. D (the other Ms. D that is! LOL!!!), those Snackwell crumb cakes with Olestra that tasted so good the night before as I sipped on Harvey's Bristol Creme while watching a Dukes of Hazzard marathon were now coming back to haunt me. "No need to worry" Dolly informed me. "I grew up in Tennessee, where a girl knows what to do with an unexpected handful or mouthful of shit." Boy was I relieved as Dolly proceeded to roll up her sleeves and get to work on my butthole. We spent the next two hours behind the dumpster in pure ecstasy.

[continued]

I found out a lot of fantastic things about Ms. D. She has never had breast implants for starters (those babies are all hers!) and unlike most woman that I have been inside of, her breasts come out of her shoulders. Also, not only does Ms. D shave the HAM, but it is also pierced with a chain hanging from which is a gorilla's fist. Apparently, this was a present from her longtime gal pal Beth Howland.

Needless to say, after I shot my Lady Load for the eighth time that afternoon. Dolly and I collapsed in a heap on top of this large glass tank that contained numerous hard boiled eggs in some sort of green fluid. I looked up at Dolly as she rested and she was so adorable lying there with Fred "Rerun" Berry peering off of her ample bosom, feces smeared all over her hands, face, neck, thighs, and back. She started to snore slightly and that was my cue to amscray. I got up, pulled out an errant soup can lid that was lodged inside of me and got myself together and went back in to town.

I never did get back those pajamas.

I found out a lot of fantastic things about Ms. D. She has never had breast implants for starters (those babies are all hers!) and unlike most woman that I have been inside of, her breasts come out of her shoulders. Also, not only does Ms. D shave the HAM, but it is also pierced with a chain hanging from which is a gorilla's fist. Apparently, this was a present from her longtime gal pal Beth Howland.

Needless to say, after I shot my Lady Load for the eighth time that afternoon. Dolly and I collapsed in a heap on top of this large glass tank that contained numerous hard boiled eggs in some sort of green fluid. I looked up at Dolly as she rested and she was so adorable lying there with Fred "Rerun" Berry peering off of her ample bosom, feces smeared all over her hands, face, neck, thighs, and back. She started to snore slightly and that was my cue to amscray. I got up, pulled out an errant soup can lid that was lodged inside of me and got myself together and went back in to town.

I never did get back those pajamas.

I am weeping over the plight of all the ravaged anuses...

I was in the Midwest, on a driving vacation, just kind of tooling around and stopping wherever I felt like it. I stopped for lunch at a place that was one of those all-in-one kind of back-country resort places. It included a diner, a canoe rental operation for the river nearby, a campground, and a trailer rental. I hung out for a bit after lunch, chatting with the guy who was handling the returning canoe rentals, coming back from their half day float trips. He was a younger cub-type, early 20s, with a sparse beard and mustache. Also, a bit of a gut but fit-fat, in pretty good shape.

I was attracted to him but I was also deeply closeted, painfully introverted, and in Midwestern back country, so I really was just passing time. Or I was until I caught him unmistakably glancing at my crotch. Even that wasn't enough for me until I caught him doing it again (I was in sweatpants).

I'm embarrassed to write the rest because it's just too painfully, "Dear Penthouse...." But that's the thing ... in that time (early 80s), those letters and the occasional porn magazine were my frame of reference as to how to hook up. So I'm afraid the rest of the encounter was terribly cliched, up to and including the old, "Hey, let me massage your back since I know you've been working hard all day!" Suffice to say that I rented a trailer from them for the night, I asked him to point me to a decent local restaurant and invited him to accompany me, and I really did massage his back, which led to a fun evening.

I was on the road again the next day and never did see him again but I jacked off to that encounter quite a few times over the next few years.

Summer after grad school I traveled through the Greek islands before starting my job. Was taking the bus back from the beach in Mykonos, a hot guy kept cruising me. When we got off the bus we immediately started talking, went back to my room, I fucked him for hours. Hot anonymous sex. Great memories.

Train sex. This was before there were cameras everywhere.

A question. Do the bottoms in all these scenarios douche every morning JIC they have a random hookup or... do they have self-cleaning ovens?

[quote]I was on my knees quicker than (insert name of 00's pop artist--choose one.)

Arcade Fire

I have never felt like this

For once I'm lost for words

Your fuck has really thrown me

This is not like me at all

I never thought I'd know

The kind of cock you've shown me

Now, no matter where I am

No matter what I do

I see your dick appearing

Like an unexpected fuck

An unexpected fuck

That only we are doing

I was downtown meeting some friends after work for a drink. ( I was closeted at the time). I was walking to the parking deck and passed a bar that was fairly empty. I went in to have a beer and saw a young guy who was the assistant manager at a sports bar, also downtown that we all frequented. We started talking and he was very drunk. He asked me for a ride home. I said sure, not thinking much of it. He went to the restroom to piss. I followed him to piss as well. He flashed his cock beside me. I looked at it and just said, Nice. He leaned over and kissed me. I was shocked because I had no idea he was into guys. We left and he sucked me all the way back to his apartment. Luckily it was pretty close by. We went in and the place was a filthy dump. We were making out and he asked me to fuck him. Since he had a condom I did. It was great sex, nice guy but I think he was a little freaked out about it afterwards.

I've done it in the Prado, the Rijksmuseum, the Met, the Frick, the (old) Whitney, the American Museum of Natural History, lesser museums, a number of Newport mansions, Vanderbilt mansions. There was a time it was so easy and common to get sex in North African museums and historic sites, as well as every where in Italy.

R28

Not to be too gross, but I used to do enemas everyday. I was afraid if I ever bottomed, it wouldn't be clean otherwise. After 2 years of living with my boyfriend I asked him if he ever cleaned out and he said no. It was always squeaky clean when he bottomed, so I thought I'd try it. For the past 4-5 years I haven't done enemas and there's never been a problem. I don't know how, but there's never any residue.

I eat a lot of fiber and only go once a day, before I shower in the morning. Maybe that's the reason?

It was a rainy night in Boston.

Never happened to me before with any kind of serviceman or utility worker. However, recently a guy from the local electric company came to my house to evaluate my place for energy efficiency. He was very chummy sitting very close to me on the couch. Before long we were both rubbing our cocks through our pants try to be nonchalant about it. Then he stretched out while I massaged him and took his beautiful uncut cock out and started sucking him. Big turn on when he took my uncut cock and began sucking me. Nice guy and hot sex in the afternoon. I got a gay vibe from him early in his visit, I just didn't think it would progress to both of us being naked on my couch. Oh yeah, he was married with kids. Never happened before.

Bump

lies and he lying liars who tell them.

I know there are a lot more whores on here. Spill!

Bump

I think a daily enema is a splendid idea!

R6 is Dennis Quaid in Far From Heaven

I guess paying a rentboy isn't unexpected and folks have nothing to share. A shame.

Driving to Morgantown WV I put into a cheap-looking motel a mile off the old downtown campus. A blowsy size-18 woman was at "reception" sitting with a sorta' scrawny blond mid-20's country bumpkin. Signing in we three had a few laughs, nothing sexual, while I eyed the guy. But I had a hunch about something. The room was a walk off reception to a long wing of rooms, one side facing the highway, the back side facing woods sloping down to the river. I was in the back. The room had been unoccupied for weeks, was stale and hot. Within five minutes there was a knock on the door .... the guy, with extra soap and towels, "making sure the air conditioner works." Not a trace of gay to him. But in his cute hesitant face and haulting voice, I knew. I shut the door, he sat on the edge of the bed. I just walked to him and began rubbing his head, neck and shoulders, pulling him to me. He put his arms around me andI laid him down across the bed and climbed on top of him. There was very mutual quick writhing, I was beginning to really get into it, he stiffened, moaned, went silent, went limp. He had come and we hadn't even gotten our clothes off. He was sorta embarrassed, I said that was ok, things happen, I'd be back after eleven, "bring me some more towels" Now the guy wouldn't have been king of the Beta house, but all night when there for dinner I kept thinking of him back at the motel. The brothers were great, still the top house and all very straight but I got enough of a vibe from three who weren't interacting together. I had a good time, one of the two in my old room was absolutely stunning. Still, I cut the evening short to get back to the motel before eleven. Reception was dark, some Indian guy on night duty. The lighting on my walkway was dim. At my room, no note, no towels. Needless to say, my bumpkin didn't show up in the middle of the night. I never saw him again. The following spring I stayed there again. No blowsy size-18, no bumpkin, all-new Indian management and not a cute one in the bunch.

This happened about 30 years ago and the whole episode is a strange mystery. It was back when I was on the sex lines all the time. I got a sex call from a guy wanting to come over. He said he worked for AT&T. I had never met him before. He came to the door and was a really handsome guy. We had sex, and I remember really enjoying it. He left and I never saw him again. I'm not sure how he even got my number but I suspected he may have listened into my calls, though I'm not even sure that was possible then. It was all so strange. But fun!

A number of years ago I lived in an apartment building and the married couple down the hall knew I was gay. One night there was a knock on my door and it was Mike, the married man. He had been really drinking and was feeling no pain. He said that his wife was gone away for a few days and to come over for a visit, so I did. He made sure that we sat on the sofa together and then after some small talk he whipped out his cock, big and uncut - it was impressive. So I took my pants down, whipped mine out, got hard, and we both started to masturbate together. I eventually came but he was still chugging away. Finally he led me into their bedroom, pulled me down on the bed with him, under the covers, and in a drunken manner he snuggled against me and talked to me in a haze just like you would talk to a woman. After awhile it began to be pointless, snuggling and holding in bed with a drunk - not terribly romantic or even sexual anymore - so I got up and left and went back to my apartment.

He had music on loud and I could still hear it back in my apartment. Someone from the building eventually went to his door and pounded and told him to turn off his music but I think he had either passed out from the booze or fallen asleep. So the music went on. I suspect that when he sobered up the next morning he scarcely remembered anything.

When I was sleeping over at a friend's house and suddenly in the darkness I felt his cock in my face.

High school swim team sleepover in a hotel for finals. two to a bed. Lots of jokes. I for sure thought my favorite teammate wasn't gay. But he insisted that we share a bed, "Cuz you're cool."

Later that night, after some jokes, lights out. Half an hour later, he rolls over wraps an arm around me, and his cock is pointing at my butt. I waited as he sort of humped me quietly, then rolled over. He pulled away, I pulled him back. We ever so quietly jacked each other off through our shorts and kissed a few times. i wanted so much to go down and blow him, but that happened a few days later.

Sweet teen cum! Dean, I miss you!

R44 Back then it was possible to listen to other people's phones. I worked in one of the local companies during summer in junior high and sometimes we listened what people talked.

Bump

Surprise anal in the Princeton University chapel. Summer of 1986. Well that was unexpected!

My first boss, who also hired me when I was a senior in hs, seduced me shortly after I was hired. Hot married blonde w 3 kids. We sucked all summer. He was 29, which seems so young to me now. I wrote about him in a diary and my mother snooped, read it, and had a fit. Damn it, horny teens need lovin' too.

There was this one time, at band camp...

At the Christopher Street sex toy store in Ptown in the late 90s. It's off season and I walk in to wander around. I ask the (very hot, tattooed muscle bear) behind the counter to look at cock rings and ask how they're supposed to be put on. He hands me a rubber one and I go in the changing room to try and get it on. I can't. I have no idea how it's supposed to go. He says "Everything OK in there?" I say, "Not really." He says "Can I come in?" I say "Sure." He comes in, grabs my whole package and expertly slips on the cock ring. I instantly get hard. He strokes me a couple of times, and says "hang on a sec." A minute or so later, I hear the door to the shop close and him clicking the lock on the front door. He comes back and starts sucking me off, then offers up his (beautiful, hairy, muscled) ass.

That was nice.

Horny bump

In the library at my college

In college was at a science exhibition and was talking to an exhibitor about how I had a lot of spiders in my apartment but I just let them be. I feel a guy right next to me, salt and pepper hair mid 50s, he says he's an entomology professor and he's never heard anyone be so open to letting them be. Our arms were touching and it was electric, he took me to his office, he hugged me so tightly, I blew him for maybe 30 seconds max before he came. He returned the favor I maybe lasted 5 mins. He was married but we met a few other times at my apt, he loved body contact and was a great top.

Never happened to me. I guess I don't know, or want to know, how to "cruise."