Most unexpected sexual encounter

[stretch8888]

I've always been a bit oblivious so there have been a good number of unexpected sexual encounters but i had one yesterday that came right out of no where.

Friend of mine I've known for about six years, average height, petite body, small perky tits and a great ass, blonde hair blue eyes, very cute and shy, I've made a few advances but never got anywhere. She starts texting yesterday saying she was in town visiting family for Easter and was wondering if she could swing by for a break from her family. She came over and we were catching up over a few beers, i get up to grab us another and when i return out of no where she asks "You wanna have sex?" certainly caught me off guard as i didn't have a response and she just smiled as i looked at her, then she tells me the guy shes kind of seeing has been away at work for almost a month so she hasn't had sex in a while and with her family is stressing her out all weekend she was kind of hoping I'd be interested in some friends with benefits action, she didn't have to ask twice and we made our way to the bedroom, practically ripped each others clothes off, given her typically shy quiet personality i was a bit shocked, i don't think she was expecting me to be so big but she didn't waste any time getting it in her mouth, she had skills but i was eager to get inside her so i yanked her up and she was fucking tight but she took it, from there on it was just some hot sweaty straight up fucking, finally got her on her back and was giving her every thing i had, pulling out didn't even cross my mind until I'd unloaded inside her, i apologized for not pulling out but she didn't mind, we laid there for a few minutes before she noticed i was still pretty hard, checked the time and said we could go again if i wanted, she gave me a quick suck then climbed back on and we fucked one more time before she had to head to another family dinner.

 

[FLScubaGuy]

Not long after I was out of college, at a company Christmas party, one of the senior managers invited me back to his room to fuck his wife. It was out of nowhere. Crazy situation.

More details?

 

[halcyondays]

Another happened at a summer party when I was in college. One of my high school buds and his new friends shared a house. I didn't know any of them. After a blowout party on a Saturday night about a dozen of us were passed out on the living room floor (instead of driving home drunk--take note). I woke in the middle of the night to my friend banging his girlfriend in the middle of the floor. Why they hadn't gone to bed in his room escapes me. Maybe another couple had taken his bed.

Without moving too much I looked around to see if anyone else was watching. As far as I could tell no one was except the girl next to me. Her eyes met mine in the dark and she smiled. We listened to their love making until they finished. She moved closer. I felt her hands first on my arms and shoulders then my chest. We started kissing. Our bare legs twined. Her hands felt my hard on through shorts. My hands felt her breasts through her tank then her butt and pussy under her skirt.

It was all super slo-mo trying to avoid attracting attention. Stealth love. Our shirts and undies came off, her tiny skirt stayed on, my shorts didn't, she climbed on top and grinded against me before pushing on. For a long time we were belly to belly and chest to chest her hips making tiny movements taking me deeper and deeper in her wet pussy. When she sat upright and started riding me I stopped her, pulled condom from my wallet and rolled it on. She smiled and bit her lip in surprise then got back on and went crazy. (I got a girl pregnant when I was in high school and didn't want a repeat of that.)

She was tall and slim with long straight black hair, big blue eyes and a big toothy smile. Her face was supermodel beautiful. Her small breasts were easy to suck in my mouth. Her legs had to be 40 inches long. I had talked to her several times during the party and sat next to her on the couch for a while but didn't know anything about her.

She kept me inside for a while after she finished then rolled off and snuggled up. We kissed and felt each other for a long time. It's your turn, she whispered, pulling at me. I rolled on top of her and she wrapped those long legs around me while I pounded her till I filled the condom. I was drunk and self-conscious so it took a long time to come. I think she came again while I banged her.

She was the first woman I had sex with without knowing her name. She didn't know mine either. We learned them the next day. Funny thing is that no one said anything about it. I guess they all really were passed out.

 

[Oralgami15]

I was in my early 20's and three of us (me, another guy and a girl) rented a house that was far enough away from the beach to be affordable but close enough to get there as often as we wanted. Two college students had been living in the finished basement but when the school year ended in May, they left. We placed an ad looking for someone to rent the basement and two girls from Boston came down looking for a weekend place near the beach. They were a little older, had decent jobs and were a bit more "experienced" than we were.

One Saturday, probably their second weekend in the house, "Judy" and I were the only ones home. It was raining and thus Judy wasn't going to the beach. We started drinking beers and smoking and just trying to get better acquainted. My roommates played backgammon a lot and I asked if she played. She said she was pretty good in college and I invited her to play. Pretty soon we were playing strip backgammon. I was kicking her ass at first and when she had to take off either her shirt or pants she didn't hesitate to pull off her shirt revealing a sexy little lacy black bra. I was getting turned on and started making some high risk moves hoping to quickly see what she was wearing under her jeans. However, my bold moves proved foolish and I found myself left with only my tighty-whities on as we began the game I had to win. I lost. I had been to nude beaches many times before, and had my share of girls. This was different. She looked at me with a look of pure delight and she was not going to let me off the hook. "C'mon, stand up, take 'em off and let me see what you've got". I did what I had to do and dropped them and I never felt so naked before as I watched her eyes study my body. "turn around so I can see your ass". After being thoroughly inspected, she stood up and grabbed my dick and said "let's go downstairs" and lead me by my dick down the stairs and to her bed.

 

[AlteredEgo]

My online dating profile is really, really silly. Over the top ridiculous. I think it's very funny, and only someone who gets and enjoys my jokes is really up to the task of hanging out with me. Every few years I dust it off, update some of it, and make it public for a little while. Some of the people I meet that way are destined for friendship. Maybe we really enjoy each other's company, but just have no mutual desire to bang. I've actually been friends for about as long as OKCupid has existed with one such dude, for example. We don't even flirt with each other anymore, but we keep up with each other's lives. If he needed something I had, I would take care of it. Vice versa. That sort of thing.

Anyway, I made such a friend. More recently, about a year and a half ago. We are goody in the same ways, and we just clicked instantly. Around him, I laugh so hard I can't see or breathe. Funniest dude I ever met. We have heaps of silly fun. I was surprised when I picked up on a hint that he was sexually interested, and realized he'd been subtly dropping hints for ages. I really thought he didn't find me attractive. Turns out, he just didn't think I could ever find him attractive, and there was a bit of a preemptive rejection. I'm glad we figured it out. Now he's more fun than ever, and it's easily the best sex I have ever had.

 

[RowanB]

Someone I used to work with. Straight & married but even so still hooked up with a few of the girls at the office. Hot guy, very muscular.

Anyway, we went to another city to visit a client and took the train back to London together at the end of the day. When we got to London he wanted to go for a drink, so we did and then had quite a few.... I was always hot for him, but he's straight so I would never make a move.

To my surprise, he turned the conversation to dick & asked me if I shave. Said that I like it clean and he said that he keeps himself clean too. Few minutes later he "wanted to show me"and get my opinion..... Lol. We hooked up that night and now, a year later, we're still hooking up regularly.

 

[deleted873528]

Mine would have to be with college roommate, I know a lot of us experiment in college but certainly wasn't on my list of things to do.

 

[simbablk]

My most unexpected was my first FMF threesome. It started with us just getting naked and having fun. But in the end, I found myself fucking them both. Yes, FMF sounds fun, but let me tell you it's EXTREMELY exhausting - especially when the women aren't into doing things to each other!

 

[Max_Polo]

My most unexpected was my first FMF threesome. It started with us just getting naked and having fun. But in the end, I found myself fucking them both. Yes, FMF sounds fun, but let me tell you it's EXTREMELY exhausting - especially when the women aren't into doing things to each other!

How horrible!

I feel so sorry for you, I think I might start a GoFundMe campaign.

 

[simbablk]

How horrible!

I feel so sorry for you, I think I might start a GoFundMe campaign.

Oh please do! There needs to be a memorial for men having to fuck more than one woman fund! LOL

 

[deleted300444]

Too many to reference, they used to fall into my lap. Today, not so much and that is ok.

 

[insert_8]

How horrible!

I feel so sorry for you, I think I might start a GoFundMe campaign.

Isn't that the premise of the movie, "Three in the Attic"?

In the swinging sixties three girls discover they have the same boyfriend who has been playing around with them all while vowing fidelity to each. To teach him a lesson he won't forget, the trio contrive to lock him up and continually favour him with their attentions in turn.
​

We wewre supposed to feel sorry for Paxton Quigley. Once you got past the risque' novelty of the basic idea, it wasn't much of a movie.

 

[lightining]

I will preface this by saying that this is the place I go to get tested, so my male nurse gave me a prostate exam and shortly after he started it turned into a fingering of my asshole and then he reached around and stroked my cock to completion.

 

[halcyondays]

We didn't have sex on the spot but a dental assistant who told me she got off at six had me inside by six-thirty.

 

[libralover4u2]

My (then) wife and I lived in a large apartment building. She taught school in an adjacent town. There was a couple living in the apartment above us that we went out to dinner with sometimes. She worked in a bank that closed on Wednesday afternoons. She was absolutely gorgeous. One Wednesday I came home at lunchtime to change into a suit for a briefing I had to give that afternoon. I changed and as I was coming out the door, my gorgeous neighbor was coming home, walking up the stairs. She asked what I was doing home in the middle of the day and I told her. She asked if I have any lunch. I told her that I had not. She invited me upstairs to her apartment to have a bite to eat. I had a little extra time so I told her, "Yes,' and followed her upstairs to her apartment. As soon as we got inside her apartment she turned to me and said, "I am your lunch; eat me." Apparently my wife had told her that I was good at eating pussy.

After some good foreplay I went down in her and over about 30 minutes gave her there orgasms, the first time she every had multiple climaxes. We then has sex. Afterwards she said, "We need to do this every Wednesday;" and we did, for about two years, until we moved away.

 

[Nowyoudont90]

I took a cruise in the South Pacific lots of years ago. I had gone on the cruise to meet females and have fun. I met plenty of females and got nowhere. It was frustrating. One night, after leaving a dance where I got precisely nowhere with anyone, I headed back to my cabin. I had a cabin to myself. The passageways on the ship were quite narrow and I was just about to unlock my cabin door when a guy walking towards me asked, "No luck for you either?" I was surprised at that and he explained that he had seen me sitting alone at the dance and saw me leave, he, apparently, had been sitting close by and was having the same issue as me. He would ask single women if they wanted to dance and was knocked back every time. Exactly the same issue I had.

So... When I left, he decided to leave as well, not with the intention of talking to me, but to go back to his cabin and go to bed. He went one way, I went the other, and it turned out we both had cabins off the same passage. His was a shared cabin, mine was a single occupancy cabin with a queen bed and a view of the ocean. We talked for a few minutes and I unlocked my cabin door when he said he was going to have to go to bed frustrated and sharing with three other guys he didn't know so unable to fix his frustration. I got what he meant and said I was glad I had a cabin to myself. The conversation went on and we talked about the women at the dance and seeing some of them leave with other guys. I ended up asking him if he wanted to come in so we would not be crowding the passageway. Numerous people had to get by us as we talked. One woman said "Take it into your cabin guys!"

The two of us went into my cabin and he surprised me by telling me he wasn't gay. I reminded him I hadn't asked and told him I was not gay either. I did not tell him I was bi for fear he would think I was trying to trap him. We sat in the chairs in the cabin and talked about home, jobs, and a thousand other things. Eventually he asked, "What do you think gay guys do? Do you think they just play with each other or something?" It was obvious he was curious about having sex with another guy and I told him what men do together. He asked, "Have you ever done it with another guy?" I told him I had. He asked if I had enjoyed it and I told him that I really liked it. He asked how I knew which guys would want to do it with other men, and I told him about places to meet, accidental meetings, and other ways men hook up. He asked if I had ever had another man's cock in my mouth and I told him I had. At this point he admitted he had always wondered about what it would be like, so I asked if he wanted to find out.

The next few minutes were really awkward. He sat there silently, then asked what we would do, how we would go about it. I told we would simply undress and go to bed and see what happened from there. He said, simply, "Okay..." and stood up. I could see his erection through his pants easily. I could also see that he was leaking a little pre-seminal fluid through his pants, so I knew whatever we did, it wouldn't take long.

We both undressed facing away from each other. I turned around in time to see his pants coming off and saw he was not wearing any underwear. His bottom was white and round and firm. I was half-erect and looking forward to seeing him turn around. When he did I was pleased to see he was around 8 inches in length and hard as stone. He stared at my groin like he had never seen another man's penis before. I went to the bed and pulled the covers back. He just stood there not moving. He only moved once I got on the bed. He slowly walked over to the bed and sat on the edge. I asked if he was okay and he said he was worried that he would cum too quickly. I told him it didn't matter and that I understood. He turned and lay down on the bed. He was rigid with nervousness, so I took the lead and started stroking his penis. I could tell he was likely to cum very fast, so went down on him, taking him into my mouth very slowly. I did not even get all the way down his shaft before he came.

After he came, things got very awkward. He had no idea what to do with himself and I let him off the hook by telling him he could leave if he was uncomfortable, that I would be okay if he did. He apologized for coming so quickly and I told him it was no big deal, so long as he felt better. A minute later he was gone out of the room.

That night I went to sleep after relieving my own little problem and worried about what could come of it.

The next morning I went to breakfast in the dining room and saw him there. He smiled and said hello as I walked past and I said hello back to him and went to my table to eat. At about eleven am I met him again on deck. He thanked me for putting him out of his misery the night before and said he had to wait for the other people in his room to leave before he could masturbate thinking about the night before. He asked if I had felt alright about it and I told him I thought he was wanting round #2. We ended up back in my cabin and - this time - having a long session with a lot of oral sex, a lot of body exploration, and finishing up better than either of us expected.

The cruise was a two week deal with a lot of island stops along the way. We had sex eight or nine times before the cruise ended and it turned out he like m/m sex as much as I do.

Was a great cruise with even better sex!

Hot

 

[lapdog2001]

Two of the longest relationships of my life started as unexpected surprises.

The first was a female friend with whom I had expressed interest, but she was only interested in me as a friend. After almost a year of platonic friendship where we grew really close, a day spent together ended up with her spending the night on my couch, (which wasn't unusual). While watching TV she was chilly, so I grabbed a blanket,sat right next to her, and covered us both to warm her up. She was surprised I decided to get that close to her, but she was very much okay with it, and even snuggled closer to me to get warm. When it was time to say goodnight I 'tucked her in' on the couch, and gave her a kiss on the cheek goodnight. Her response led me to give her another kiss, and another, and within a few minutes she had pulled up her shirt and bra so I could fondle her breasts and suck on her nipples. She then asked me to finger her, and undid her jeans and shimmied them down along with her panties. While I fingered her, she reached for my crotch caressed my very hard erection through my pants. I stopped for a second to unzip and lower my pants so she could now stroke my rock hard penis while I continued to finger her until she came.

We stopped after that, but went to sleep together, spooned and half naked on the couch. I awoke the next morning with a raging erection and she then went down on me, and with lust in her eyes asked if I had a condom. I said yes, retrieved one from my nightstand and put it on, and proceeded to finish what we had started the evening before, and what I had hoped to happen for the last year. Our friendship turned into something more, and with some ups and downs, and some off periods, continued for 8 years.

The other unexpected sexual situation occurred with the woman who is now my wife. We had met through mutual friends and had spent some time together here and there over a few days of a large group vacation. One night after dinner we were talking over a drink at the bar, and her smile and eyes 'told me' to lean over and give her a kiss. That kiss was very well received and enthusiastically reciprocated. She asked if we could go someplace else, so we ended up in my room, where the kissing turned into our hands exploring each other and unbuttoning and unfastening clothing. I cupped her firm D cups breasts and sucked on her eraser tip nipples, while she caressed my very hard bulge before undoing my belt and pants to release me. When she had me fully out and about to go down on me, she said "Oh my!" and then took me as deep as she could. After a bit, I went down on her and brought her fairly quickly to an orgasm. I put on a condom and then we enjoyed each other in the first of many times making love that week, and then over many years now.

Sometimes an unexpected encounter can turn into an amazing relationship!

 

[halcyondays]

I've mentioned before I attended a catholic university. One night I was invited to a party thrown by a handful of Jesuit novices and aspirants. They lived off-campus in a regular house with a garage on the alley in the back. A fairly large crowd of catholic students packed the place, men and women represented equally.

Amongst the ladies was a slim, big breasted co-ed--easily the prettiest girl there. Every time our eyes met she smiled at me. We chatted a lot, played on the same then opposing charades teams then won at pictonary. At one point we were alone in the kitchen getting drinks when she looked at me and went out the back door. I followed. We sat close on the steps of the back stoop and within a few minutes she pressed in and we were necking. Then her hands were in my lap and mine were brushing her tits.

When our kiss broke she bit her lip. I stood, took her by the hand and led her down the garden path to the garage in back. A car sat inside but so did some extra furniture the Jesuits kept there. We made out on an overstuffed chair. I got her blouse open, her bra off and her big tits out. She got my shirt off and my shorts undone but took off panties herself.

Do you have condom? she gasped between kisses. Yes, I said. Put it on, she said.

We banged right there her big tits bouncing while she rode me in her hot little skirt. One turn each then we dressed and returned to the party.

 

[Oralgami15]

Okay - I'm not real proud of this because I was married at the time and because of the general sleaziness of it.
I'm a lawyer and I had just joined a new firm and was transitioning from commercial work into the more lucrative world of personal injury litigation.

I was having a bad day. I had only been there a month and was overwhelmed from the shear volume of files I had been assigned and the demands imposed by my boss - a very well known and respected litigator. I was wondering if I had made a terrible mistake joining the firm. One of his legal assistants - a very friendly and helpful married woman in her late 20's but totally unattractive and overweight - came into my office and said "boy, he is up your ass today. Is there anything I can do to help?" I expressed my appreciation for her kind words but said that I'd manage. She then shocked the hell out of me when she leaned over my desk and whispered "meet me behind the supermarket up the street and I'll suck your dick." I wasn't sure if I heard correctly but as I looked her in the eye she had a big smile on her face and she confirmed her offer by whispering "you go now and I'll follow in 10 minutes." There were so many reasons why I shouldn't have considered for a second what she was proposing but I heard my voice respond "Okay"

10 minutes later I was sitting in my car parked among the trailers, pallets, dumpsters and other things you find behind supermarkets as she pulled up next to me. She got out of her car and into mine and without saying a word gathered up her long shoulder length hair and wrapped an elastic "scrunchy"around it to hold it behind her head. I looked around to make sure no one was watching and reclined my seat and opened my pants, lifted my ass up and slide them down and leaned back. She leaned over and started sucking away with a will that showed that she loved what she was doing. She wasn't at all concerned when I gave warning and she savored every drop. After she was finished she popped back up with a big smile on her face and commented that she wanted to it all so I wouldn't have a wet spot in my pants. I reached for my pants and as soon as I got myself back together she hopped out. It was absolutely not a big deal to her and she did it many times after.

 

[nailz]

During a really bad storm/power outage with my yoga teacher. I said eww, I don't want to go out in that, and asked him if I could hang around the studio until it stopped.
So we sat around a bunch of candles just talking about silly stuff and eating chips and drinking vodka-OJs and totally out of the blue he asks "Want to fuck?" (So much for romance )
I thought about it for a bit and just said OK, why not..

Don't judge: it's just sex, and it's a great way to pass the time