Most unexpected sexual encounter

[HorseHung40's]

I played on my college tennis team. I remember that the team was invited to the home of one of the sponsors. She lived in a very big home in Winnetka, IL.

The team and I were in our whites. For each of us, there was a middle aged woman, who took an interest in us. The one lead me upstairs to show me the rest of the house. She led me into one of the rooms, and, closed the door.

Before knew what she was doing, my shirt was off and my shorts were around my ankles. i was still wearing my jockstrap, although she had that off quickly. I was instantly hard. We fucked for the longest time.

 

[tony decatur]

I played on my college tennis team. I remember that the team was invited to the home of one of the sponsors. She lived in a very big home in Winnetka, IL.

The team and I were in our whites. For each of us, there was a middle aged woman, who took an interest in us. The one lead me upstairs to show me the rest of the house. She led me into one of the rooms, and, closed the door.

Before knew what she was doing, my shirt was off and my shorts were around my ankles. i was still wearing my jockstrap, although she had that off quickly. I was instantly hard. We fucked for the longest time.

Would love to hear more details about this!

 

[HorseHung40's]

After the fuck session, the lady led me downstairs. i was now nude and so were my team mates. The women were clothed.

They liked pulling on our dicks and balls, or, teasing us to get us horny again. It worked! LOL. We then fucked another woman.

This continued for a third time too.

The women were they very generous with money for all of us, and, sent us home in limos.

 

[cedarizzo]

I used to help out a friend of mine with his catering business. My friend was gay and had a lot of gay men and lesbians working for him. I did some part-time work for him. I mainly would help in the kitchen sometimes and I would also help with the big events. One weekend, I was helping at an outdoor wedding reception. There were quite a few new waiters that I hadn't met before. I noticed 2 guys that I thought were really hot. I was busy in the kitchen and didn't have a chance to talk to them. Later that night, I went to the local gay bar with my boyfriend. I noticed those 2 hot waiters were there. It looked like they were together.

The next time I saw them was at the biggest catering event of the year. It was a fundraiser that was held at the catholic high school. The event was held in the cafeteria, gymnasium and hallways of the school. The girls and boys locker rooms were used a temporary storage area and changing area for the catering staff. I was given the job of driving the van and moving large totes of food from the catering kitchen to the catholic high school which was 5 miles away. At one point while we were all caught up, one of the cute waiter couple came up to me and we chatted before the event started. I told him that I didn't realize they were a couple. He said they both played together and separately. I said that was cool. My partner and I were the same way. I thought I noticed a smile on his face.

A little bit later, I had to piss really bad. So I walked across the gymnasium to the locker room. I walked by him and he smiled as I walked by. When I entered the locker room I could tell that somebody had followed me in there. As I turned the corner to where the urinals/stalls were, I turned my head around to notice that it was him that was following me. I was curious to see how far this would go, so I walked into the handicap stall at the end and left the door open. I pulled out my dick and started to piss. Sure enough, he followed me into the stall. He smiled at me and said he needed to take a leak. He pulled his dick out and of course I had to look. Soft, he was probably 5" long and it was thick! My dick started to get hard and when I finished pissing he reached over and started stroking it. I don't remember if he actually pissed, and at that point I don't care. But I reached over and started stroking his dick. When it was fully hard, it was 7" but really thick. He saw the excitement on my face and he grabbed my head and pushed me down. I dropped to my knees and started sucking his dick. It filled up my mouth and I was worried about my teeth scraping his thick dick. I sucked his dick while he kept reaching down to feel my ass. So I knew I wanted that thick dick inside me. I turned around and rubbed some spit on my hole. I felt his dick push against my hole. I took a deep breath as he entered me. He was stretching my hole like it had never been stretched before. It didn't take long before he shot his load.

Later on that night, I had to run back to the catering kitchen to grab some more food. Normally one of the other cooks would go with me, but they were all busy. The hot waiter walked up and said he needed more glasses from the catering kitchen. So the boss sent us both. We got back to the kitchen and immediately went to the bathroom. I started sucking his dick again. I told him I wanted him to fuck me more. So I turned around and he started fucking me for a second time. He came the second time and we grabbed our items and headed back to the high school.

At the end of the event, we were loading the vans. I got the last of the kitchen items that needed to go back. The hot waiter said he needed to go with me to grab more glasses. So we made it back to the catering kitchen and unloaded my stuff and grabbed more glasses for him. As we loaded his glasses, I reached over and grabbed his dick. He asked if I wanted another round. I said of course I did. Since the kitchen was full of people so we got into the back of the van. I dropped my pants and got down on all fours. He got behind me and fucked my loose ass. It took him a little longer, but he shot his 3rd load of the night into me. It was hot! I told him that I was sore and wore out because of him. And I hoped that it would happen again. And we met many times again after that.

 

[1233057]

Very sexy story. Man he sounds like a stud.

 

[puspentit]

Great story.

Reminds me a of an old saying.
View attachment 1150908

Both boobs and cock are hot

 

[niagarachatter]

Love this thread, I am a smoker and stay at hotels for work lots. None of the hotels around allow smoking inside so I go outside in just a t-shirt at night for my smokes and have had the wind uncover me a few times and have had a blow job outside the hotel once when a guy seen me naked under the shirt. My shirt hangs almost to my knees but is loose around me almost looks like a womens dress.

 

[deleted817802]

When I was getting my MBA, one of my classmates asked if I’d do him a favor. For the past couple of years, he had been doing this girl’s taxes but he didn’t have the time to do it this year. Could I do it? I was kind of busy myself, so I started to make up an excuse. He quickly interrupted and said, “I charged her $50... and, she’s a model.”

So that lifted my interest. He gave me her phone number and I called to set up a time and get her address. On the appointed day, I went over. Looking forward to seeing what this model looked like, I was unpleasantly surprised when a surly guy my age answered the door. I told him I was there to do Denise’s taxes. He yelled back into the house, “Are you expecting some guy to do your taxes?” A female voice answered, “Yes, let him in.”

So I go in and meet her, and she introduces me to her obviously live-in boyfriend. A bit of a letdown for me! She was pretty but not spectacular... I found by looking at her pay records that she made 80% of her income as a hostess at a high end restaurant, the modeling consisted of a few photo shoots for newspaper ads for a local retail store. She had me work in the dining room and brought me her records and receipts, then she and her boyfriend hung out in the living room talking and occasionally answering my questions. After a bit the boyfriend said he was going out to meet some friends and told her he was taking some money out of her purse, and left.

I finished after about an hour, then had her come in and quickly went over the return and had her sign it. She thanked me and went to her purse to pay me. Apparently the boyfriend had taken all her money, because I heard her say, “Fuck! He didn’t leave me anything!” So she started explaining how she couldn’t pay me then but could go to the bank or wait until her next pay check. I could see that was going to turn into a hassle for both of us, because then I’d have to arrange another time to come back... so I just said, “That’s ok, let’s just skip it.” She argued a bit but then said, “You’re so sweet!” and went to kiss me, I thought on the cheek, but it ended up being on the lips and turned into a French kiss. Before I knew what was happening, she was undoing my belt and pants, saying we didn’t have much time. She dropped to her knees and started sucking me in a frenzy.

The whole scene had unfolded so quickly and unexpectedly that it couldn’t have been more than a minute or two before I was having a huge knee buckling orgasm, pumping a huge load down her throat...surprisingly she swallowed every drop. As soon as we were done, I pulled my pants up and left, never saw her again or even remember her name.

 

[lapdog2001]

When I was getting my MBA, one of my classmates asked if I’d do him a favor. For the past couple of years, he had been doing this girl’s taxes but he didn’t have the time to do it this year. Could I do it? I was kind of busy myself, so I started to make up an excuse. He quickly interrupted and said, “I charged her $50... and, she’s a model.”

Before I knew what was happening, she was undoing my belt and pants, saying we didn’t have much time. She dropped to her knees and started sucking me in a frenzy.

The whole scene had unfolded so quickly and unexpectedly that it couldn’t have been more than a minute or two before I was having a huge knee buckling orgasm, pumping a huge load down her throat...surprisingly she swallowed every drop. As soon as we were done, I pulled my pants up and left, never saw her again or even remember her name.

I'd say you got payment in full!

 

[4097701]

I was 24 in grad school, would have been late 80s. I was working the summer for a guy who owned a landscape company, who happened to be a horn-dog of a fuckbuddy. Because I spoke a bit of Spanish and he was short of help, he asked me to manage a small crew on a 3-4 day job. By the fourth day I was down to just two guys, one of whom was about 45 and spoke good English (Tony), the other about 35 and not so much English (Manny), both really nice but the one with broken English was very appreciative of the job as he'd been having problems and wanted to move back to Texas. Tony was very average middle age and thick in the middle, Manny was much better shape, had done more physical labor and stripped to the waist everyday to work. By the last day at lunch we'd gotten pretty chummy, I knew all about their families, where they were from, personal lives, girlfriends, wives and ex-wives, etc.

At the end of the day, I offered to buy them a beer for their hard work all week. They didn't want to go to a bar but let me buy them a 12-pack. I offered to drop them at their place, a long-term motel where they were living, they invited me to have a cerveza as thanks for the ride. We were probably on #3, sitting on plastic chairs in the parking lot when the Manny (the Spanish speaking guy) has the other one ask me in English if I knew that Rob (the owner) was gay. Rob was pretty openly gay, but not wanting to appear too knowledgeable on the matter I said I "thought me might be". Tony (the English speaking guy), said "oh yea, he has grande pinga" and they both laughed. Clearly I knew, as we had been off/on fuckbuddies for about a year, but I just stayed neutral. So then Manny asks Tony to ask me in English if I like guys or girls, as he looks at me with a very kind expression and says "its ok, no problem", sort of like it was ok for me to tell them. I just grinned a bit, and said I hadn't had a girlfriend for a couple years, I take whatever I can get. We all laughed, Manny says "panocha, culo, verga, todo Bueno, you like all -- that's good my friend". and laughs again.

Well by now I'm getting toasted and should be outta there, but being 24 I have no good sense. The guys are getting pretty loaded also, Tony whining about his wife in Mexico that the sends money to, Manny carrying on about how much he appreciated me giving him a chance this week, he really needed the money. Then Manny gets kinda serious talking to Tony, sort of pushing him to just translate and tell/ask me something. Now Tony speaks a bit of broken English, and it wasn't that hard for me to communicate with him, but he told me early on he was more confident that he would be accurate if Tony translated. So Tony gets a bit sheepish, says, "Manny is very grateful you letting him work and be good friend, if today you feel like the dick you can, uh, uh, his." as he sort of does a Michael Jackson crotch grab so I get the picture. I look over and Tony has a very serious look on his face, nodding yes. I'm a little shocked, and I guess it showed because Manny starts talking very fast to Tony, who translates, "he says its ok, he has a gay brother and his friends have sucked it, he has a very big dick and guys like it, even it in the ass if you want." I said, "your ex-wife...….?" , and Tony says "its ok, don't worry". I'm still trying to soak this all in and not look so shocked I scare them off, Manny gets up while nodding yes, kind of wide-eyed, and steps inside his motel room about 6 feet and opens his pants to show me how big his cock is, maybe thinking I don't believe it. Well I'd been watching their crotches for several days (cuz its what I do), and I'd never have guessed there was that much in there, it was definitely large and he just stood there rubbing his fingers through his thick black bush. I was rubbing my cock thru my pants as Tony walked up behind me, almost like he knew what I was thinking, says "go have a quick rinse if you want" pointing to the bathroom. I gave my ass and crotch a quick scrub and as I came out of the bathroom the door opened to the parking lot and in walks Manny in nothing but a towel, he had showered next door in Tony's room. Tony never came back or participated but we did have about an hour of really hot sex. He never kissed or sucked my cock, but he jacked me like a big dog, chewed and played with my nipples while I sucked his cock, he eventually grabbed a hold of my asscheek and says "yes?". I instinctively turned around as he rolled a condom on and handed me a jar of Albolene (clearly he was prepared to do this), so I could lube my ass. Turned out he wanted me to lube his cock and guide it in while he just stood here, it wasn't fitting real well, so he laid on the bed and pointed for me to sit on it. After another try or two, he jumped up and went thru a pile of laundry and pulled out what looked like (and smelled like) an old bottle of poppers. Well that was enough to do the trick, it was in and he started pumping, I was running my hands through his chest hair and I guess he could tell I liked it because he says "you cum?" as he points to his furry tits. I was young and didn't have the control I do now, I shot all over his chest in a few minutes, he jacked more on my cock and rubbed the goo into his matted hair. I've always had a taste for hairy guys, and this one made me so hot I never lost my boner after cumming, lol. As he was still fiddling with and pulling on my cock he says "mmmm, duro…….mas?" I thought, I don't be able to walk tomorrow, but what the hell, and as I reached back realized he'd gone to 1/2 hard. So I get off him, pull the rubber off and get ready to suck it some more, when he flips over to all 4s offering me his totally hairy ass. I'm not usually much of an ass eater, but this was so hot and hairy and I thought he might like it, but he made clear that was what we were fucking, no ass eating. I got rubbered up and he put a glob of Albolene on my cock and said something in Spanish that I didn't get. He reach back and held my cock in a death grip and said "slow!". I was in much better control having cum once already, I fucked him long and slow, then faster and rougher, for close to 30 minutes. He never got fully hard again, but jacked himself a little and I stroked him while I pumped away trying to figure out what would make it good for him. He seemed to like it best on all 4s, which was hot for me because I could look at his very hairy asscheeks and it was while pumping away and reaching down and feeling his 1/2 hard big dangling all heavy that I came a second time.

Guess this thread didn’t really call for so much detail, but it was not only “unexpected” but very memorable for me as it is still wank fodder 25+ years later, lol. Also this experience really set my taste for spontaneous stroking with another horney dude.

Jesus this made me horny, this is my fantasy lol
you should write as a story and post it on xhmaster or something!!!

 

[halcyondays]

Another unexpected encounter happened with a young woman who came to my house to demonstrate a product line she was selling. A university art student she was twenty years younger than I. We met by appointment one evening. It was after eight and I was her last. She got paid by the number of demos she did whether or not she sold anything plus commissions on any sales. A friend of hers had recommended me with my permission.

A foot shorter than I she had long light brown hair and big blue eyes. I wouldn't call her stocky but her thighs, hips and belly definitely rocked light chunk under full breasts. Her fashionable skirt showed off the shelf of her ass. A skin tight scoop neck top highlighted her chest without revealing deep cleavage. Most beautiful of all was her face. Angelic best describes it. One of the most beautiful I have ever met.

She spread her wares on the kitchen island and demonstrated them. I ordered a set. After packing up she said yes to wine. I uncorked a bottle of red. We sat at the table talking for a long while then took a tour of the house ending up on the couch. She sat close her thigh against mine. I hadn't noticed her tongue stud until we kissed. I felt it again against my head, shaft and balls when she blew me. Her strong thighs bounced her on my cock sitting right there on the couch until she squealed out her orgasm and collapsed to me. I fucked her all over the couch filling two condoms. She didn't stay that night but would many others.

I saw her off and on over the next three years. She told me that her friend who recommended me had told her about me. I had fucked her friend many times but she had stopped seeing me when she got a new boyfriend.

 

[4097701]

Years ago, I was waiting tables in a restaurant in Hells Kitchen, I'm out and everybody knew I was gay, but I don't act very gay, so people never assume. One day one of the cooks heard about this, and was super interested. He was a young Mexican kid, very sweet and cute, and kept telling me "I don't believe it, you're not gay". A few days later he followed me into the bathroom downstairs and blew me, and then tried to blow me every chance he got.... horny little fucker... I miss the old days when things like that would happen, before they put cameras everywhere etc.
I have a few more I'll post later, but I used to get a lot of random sex like that, not in a while unfortunately

 

[Redheadchi]

I played on my college tennis team. I remember that the team was invited to the home of one of the sponsors. She lived in a very big home in Winnetka, IL.

The team and I were in our whites. For each of us, there was a middle aged woman, who took an interest in us. The one lead me upstairs to show me the rest of the house. She led me into one of the rooms, and, closed the door.

Before knew what she was doing, my shirt was off and my shorts were around my ankles. i was still wearing my jockstrap, although she had that off quickly. I was instantly hard. We fucked for the longest time.

I don't live far from there, I'd love to have one of the upscale housewives as a FB

 

[HorseHung40's]

I don't live far from there, I'd love to have one of the upscale housewives as a FB

I am sure that there are many lonely or bored housewives there with too much time and money on their hands, just waiting to lavish both on a handsome man with a big, swinging dick.

The more things change, the more they stay the same.

 

[Marc Cloutier]

I only had one unexpected sexual encounter, at my gym!

On a saturday afternoon, around 2h, I was in the sauna with two other guys, and one thing led to the other and we started to jerk off together, one guy was even sucking the other guy. Things stopped quickly because we were in public and someone walked by. The two other guys left for the showers (probably did some handy stuff there).

The next afternoon, same time, I saw one of the guys in the sauna so I figured I would go quickly before my work out, to relax and maybe do more Well I started talking with him and realized he was not really my type so I left to take a shower before going to work out. Well two minutes after, the guy took the stall next to mine and made eye contact and touch my foot. He did have a nice large cock so I figured why not. I jerked and sucked him under the stall for a bit. Then I don’t know why but decide to turn around and scrub my ass agains his dick. He took this as an invite and started to finger me and then pushed his cock inside. I’m not really proud of this because I didn’t know him and I don’t usually get fuck bare by strangers, but in the heat of the moment I let it happen. Keep in kind that the showers at my gym are all separated and in a row, and we were at the end (more secluded area) but still if someone just looked down they would have seem him fucking me under the stall. He was very large and I don’t know how he was able to fit without lube.... this lasted 2 mins and then I turned around (I didnt clean there so I was afraid I made a mess) but it was all good and he came like 3 seconds after.

We both washed and went to the sauna after. Talked a bit, asked him if he was cleaned (he said yes) and then I went to work out! 1h after I came back to the sauna to relax and he was still there! I wonder if he did anything else that afternoon lol He left not long after and I never saw him again...

 

[Great Dane]

Years ago I was backpacking in Brazil and went by nightbus to a small coast town. The bus was only half full, but next to me sat a young, good-looking Brazilian guy who didn’t speak a word of English. However, we made some gestures to each other when needed and he seemed very nice. It turned out he didn’t have a blanket for sleeping in the night, and since the busses can be quite could because of the aircon I made a gestture that he was welcome to get covered by my blanket as well which he happily accepted. The seats where slightly reclined and at one point my leg touched his (we were both wearing shorts), and I noticed he didn’t move his legs, but on the contrary moved it even closer to mine! I was pretty horny but thought it was all just a coincidence and my hungover mind playing games with me. But a few minutes later he put his hand on my thigh. I did the same with him, and he quicly moved his hand towards my crotch. From then it went fast: We unbuttoned each others pants and started jerking each other (unfortunately his cock was really small). We both came quickly and he wiped off the jizz in the bus’ curtain. We then looked straight at each other and did one derop French kiss, and that was it, carefully watching that nobody saw us. He then moved to another seat and went to sleep. Looking back at it it was both insanely hot, and I can’t quite understand how we dared to do it in a bus with people around though they were (presumably) sleeping. Nevertheless it’s still one of my hottest memories.

 

[51arledge]

Years ago I was backpacking in Brazil and went by nightbus to a small coast town. The bus was only half full, but next to me sat a young, good-looking Brazilian guy who didn’t speak a word of English. However, we made some gestures to each other when needed and he seemed very nice. It turned out he didn’t have a blanket for sleeping in the night, and since the busses can be quite could because of the aircon I made a gestture that he was welcome to get covered by my blanket as well which he happily accepted. The seats where slightly reclined and at one point my leg touched his (we were both wearing shorts), and I noticed he didn’t move his legs, but on the contrary moved it even closer to mine! I was pretty horny but thought it was all just a coincidence and my hungover mind playing games with me. But a few minutes later he put his hand on my thigh. I did the same with him, and he quicly moved his hand towards my crotch. From then it went fast: We unbuttoned each others pants and started jerking each other (unfortunately his cock was really small). We both came quickly and he wiped off the jizz in the bus’ curtain. We then looked straight at each other and did one derop French kiss, and that was it, carefully watching that nobody saw us. He then moved to another seat and went to sleep. Looking back at it it was both insanely hot, and I can’t quite understand how we dared to do it in a bus with people around though they were (presumably) sleeping. Nevertheless it’s still one of my hottest memories.

This reminded me of events I hadn't thought of in decades...
I was in college about 500 miles from home. Far enough that flying home didn't make sense financially and I didn't have a car either so it was for a few years that I was taking 8-12 hour Trailways bus trips.
I was shocked the first time a guy offered to blow me on a dark bus with few passengers and those few were either asleep or all the way up at the front. After the first time, it wasn't a surprise at all. In fact, it happened so often that it became something to look forward to on those long boring trips.

 

[4237511]

Probably my first time. It was before my ex and I made it official after about a week or so of knowing each other (both above legal age of course). We always had intense make out sessions and groping but never anything more. He had a box condoms and joked about how we should use them. He was coming over to stay at my place and said he’d pack them and didn’t know if that was a joke or not but whatever. It’s New Year’s Eve, my roommates had all left to a party and it was just him and I. We were laying in bed and then we started making out and finally we started to slowly undress, mind you we haven’t seen each other naked yet at this point. So he give me my first blow job and it feels incredible. I return the favor and enjoy it just as much as I did receiving mine. He wasn’t a virgin and had already bottomed before. So he goes into his bag and pulls the condoms out after teasing me from getting on top of me and rubbing my cock against his ass. He slips one on me and puts his fingers in his mouth and puts his spit on the condom. It took a little more spit and then before I knew it I was inside of him. Sure it felt good but it was at best ok, maybe we needed more lube. So he rides me for a little and then finished on my chest.
I thought we would’ve discussed losing my virginity but it kind of just happened therefore making it really unexpected. After that we got better and better at it of course and to this day I jack off to that first time

 

[hotbtminla]

This was a couple years ago but I still remember it pretty vividly, in large part because it was so unexpected. A close friend of mine was dating this girl who is a painter and lives in the Arts District in downtown LA, specifically in a sort of commune type set-up - loft apartments that also serve as workspace and gallery space for artists in what used to be industrial buildings. This particular one is like 3 buildings with a large shared common courtyard (more like a court-park, it was big) and everybody knows each other and they're all artists (i.e. 1/3 truly talented artists, 1/3 weirdos, 1/3 insufferable posers lol). You get the drill.

Her birthday coincided with a big community art showing so there was this big ass party. My friend asked me a 2 other friends to go, and even though it's not my scene I was like fuck it, it's something different and at the very least I'd get some comedic stories out of it.

While I am quite proudly and confidently what one would call "easy" I had zero expectations I'd get laid that night. I wasn't going to the party to find someone to hook up with, I was hanging out with my friends and I'm not really one to vanish or bail on people simply because someone wags their cock at me.

I know I looked good that night. Specifically recall that a couple days before I got the single best haircut of my life (every hair on my head is in a different cowlick so I remember a good haircut like other guys remember baseball stats). I was in a black t-shirt and had been working out a lot, had great shoes on - I looked good and was feeling confident, but again, hooking up was furthest from my mind. I wasn't trying to be sexy or charming (I'm told I tend to be both in general, but the point is I wasn't being flirty with anybody).

The party was fun but just as weird and oddly cold as I expected, but still it was fun to be able to talk to people who have wildly different day to day lives from me. Not long after we got there I was sipping a drink, surveying the huge loft and the crowd, and I saw this guy who was, quite frankly, one of the sexiest guys I've ever seen in my life. He was about my age (early to mid 30s at the time), shorter than me (I'm 6'1) thin but more in a wiry way than skinny. Mediterranean or Hispanic complexion, longish curly/wavy hair, and handsome in an offbeat kind of way. What drew my attention initially was that he laughed at something really loud and he had one of those charming, full bodied laughs. When I saw him I was immediately transfixed - he had that casual ease about him that was super sexy (in retrospect BDE but that wasn't a thing yet). His shirt was unbuttoned just enough to show he's got chest hair, and the way he moved, even when standing still, just screamed sex.

Then he glanced over in my direction and we made eye contact. I realized I was openly staring at him and got kind of bashful. He smiled at me and then went back to talking to his friends.

This routine went on for the next 90 minutes or so. I'd be somewhere talking to people, or getting a drink, or out in the courtyard, I'd look around nonchalantly and BAM we'd make eye contact from a distance, he'd smile at me, and then we'd go back to talking to whoever. The flirting was fun, but I didn't even know if he was gay, bi, or just a horny dude (or potentially a dude who enjoys winding guys up). And also I was. Not. There. To hook. Up. Plus I was a bit intimidated by him. I mean, I felt good about myself that night but was so bowled over by how completely hot he was that I was like "yeah no that isn't happening."

I can't recall how I wound up in the hallway of the loft - I know wasn't leaving yet, but was probably looking to take a leak (this was like one giant party across several lofts so numerous bathrooms were being shared). But I'm walking down the hallway of this industrial building and I hear "hey! hey bud!"

I turn around there is Hottie McHotterson trotting down the hall. He was like "you're not leaving are you?" and I was like "well soon but was just getting some air" and he was like "good because you weren't going to leave until I got to meet you." We introduced each other (I will call him Tony here) and he put his arm around me and said he would get some air with me. I recall being slightly dazed while this was happening.

Tony wasted zero time. In fact he kind of took it from 0 to 60 like an Italian sports car. He kept leaning in and talking quietly, but saying stuff like noticing I couldn't stop checking him out, that made him feel good, that he likes when cute guys make him feel good, that I was the cutest guy at the party, etc. YES I KNOW it sounds like he was laying it on thick, because he was, but also I think everything was expedited by the dozen or so eyeball fuckings we gave each other up to that point. Meanwhile I was being (in retrospect) absurdly bashful, I'd never had a guy this sexy talk to me like that in this setting. Which made him smile even more and say shit like "don't be shy bud, I loved knowing you couldn't get enough of me, and obviously want my bod." And he'd make me say it out loud.

Then he told me to kiss him. And I did. Butterflies galore. Then he quietly said "I've got a really big cock" and nodded while holding eye contact with me. I stammered something like "um" and he just smiled and said he did, and he asked if I like big cocks, made me say it out loud, etc. He asked if I wanted to see it and I was like "HERE?" I mean, we were in the hallway, not the middle of the party, but still there were people everywhere. He kissed me again and grabbed my ass, which pushed me into him, and I could feel it. I moaned or groaned or otherwise made a sound that said it all. He took me by the hand and led me up a couple floors to the top of the stairwell, where it would open to the roof but it was locked. We made out some more than he unbuckled his pants and opened them and said something like "there you go bud" and said I could feel it or see it or do whatever I wanted with it, and that it was my cock tonight.

He was, if anything, being modest when he said he had a big cock. It was magnificent: long, thick, uncut, and his balls were big too. Easily one of the Top 5 cocks ever in my presence, and on a guy who is shorter than me and wiry, so it looked even more like a whopper. And that's when "Mr. I'm Not Hooking Up Tonight" blew Tony at the top of the stairwell. More like I made love to cock with my mouth. The whole time he was talking dirty too, encouraging me to enjoy his cock. I had his shirt unbuttoned and was massaging his hairy pecs and stomach, tweaking his nipples, sucking the hell out of his cock. When he said he was close I just looked up into his eyes and kept sucking, and he smiled and nodded and shot in mouth. I swallowed every drop like it was my favorite meal.

Then we went back to the party and rejoined our respective friends. Continued to make eye contact. When it was pretty late and my friends were getting ready to leave and calling Uber etc, Tony tapped me on the arm and said "let's have a drink before you go." So I made some excuse about getting my own ride, and followed Tony over to his loft, during which he explained he didn't have any wine or booze, but that he was recharged and ready to fuck my hole, and that he wanted to find out how many times I could make him cum. I left about 36 hours later lol.

 

[cedarizzo]

This was a couple years ago but I still remember it pretty vividly, in large part because it was so unexpected. A close friend of mine was dating this girl who is a painter and lives in the Arts District in downtown LA, specifically in a sort of commune type set-up - loft apartments that also serve as workspace and gallery space for artists in what used to be industrial buildings. This particular one is like 3 buildings with a large shared common courtyard (more like a court-park, it was big) and everybody knows each other and they're all artists (i.e. 1/3 truly talented artists, 1/3 weirdos, 1/3 insufferable posers lol). You get the drill.

Her birthday coincided with a big community art showing so there was this big ass party. My friend asked me a 2 other friends to go, and even though it's not my scene I was like fuck it, it's something different and at the very least I'd get some comedic stories out of it.

While I am quite proudly and confidently what one would call "easy" I had zero expectations I'd get laid that night. I wasn't going to the party to find someone to hook up with, I was hanging out with my friends and I'm not really one to vanish or bail on people simply because someone wags their cock at me.

I know I looked good that night. Specifically recall that a couple days before I got the single best haircut of my life (every hair on my head is in a different cowlick so I remember a good haircut like other guys remember baseball stats). I was in a black t-shirt and had been working out a lot, had great shoes on - I looked good and was feeling confident, but again, hooking up was furthest from my mind. I wasn't trying to be sexy or charming (I'm told I tend to be both in general, but the point is I wasn't being flirty with anybody).

The party was fun but just as weird and oddly cold as I expected, but still it was fun to be able to talk to people who have wildly different day to day lives from me. Not long after we got there I was sipping a drink, surveying the huge loft and the crowd, and I saw this guy who was, quite frankly, one of the sexiest guys I've ever seen in my life. He was about my age (early to mid 30s at the time), shorter than me (I'm 6'1) thin but more in a wiry way than skinny. Mediterranean or Hispanic complexion, longish curly/wavy hair, and handsome in an offbeat kind of way. What drew my attention initially was that he laughed at something really loud and he had one of those charming, full bodied laughs. When I saw him I was immediately transfixed - he had that casual ease about him that was super sexy (in retrospect BDE but that wasn't a thing yet). His shirt was unbuttoned just enough to show he's got chest hair, and the way he moved, even when standing still, just screamed sex.

Then he glanced over in my direction and we made eye contact. I realized I was openly staring at him and got kind of bashful. He smiled at me and then went back to talking to his friends.

This routine went on for the next 90 minutes or so. I'd be somewhere talking to people, or getting a drink, or out in the courtyard, I'd look around nonchalantly and BAM we'd make eye contact from a distance, he'd smile at me, and then we'd go back to talking to whoever. The flirting was fun, but I didn't even know if he was gay, bi, or just a horny dude (or potentially a dude who enjoys winding guys up). And also I was. Not. There. To hook. Up. Plus I was a bit intimidated by him. I mean, I felt good about myself that night but was so bowled over by how completely hot he was that I was like "yeah no that isn't happening."

I can't recall how I wound up in the hallway of the loft - I know wasn't leaving yet, but was probably looking to take a leak (this was like one giant party across several lofts so numerous bathrooms were being shared). But I'm walking down the hallway of this industrial building and I hear "hey! hey bud!"

I turn around there is Hottie McHotterson trotting down the hall. He was like "you're not leaving are you?" and I was like "well soon but was just getting some air" and he was like "good because you weren't going to leave until I got to meet you." We introduced each other (I will call him Tony here) and he put his arm around me and said he would get some air with me. I recall being slightly dazed while this was happening.

Tony wasted zero time. In fact he kind of took it from 0 to 60 like an Italian sports car. He kept leaning in and talking quietly, but saying stuff like noticing I couldn't stop checking him out, that made him feel good, that he likes when cute guys make him feel good, that I was the cutest guy at the party, etc. YES I KNOW it sounds like he was laying it on thick, because he was, but also I think everything was expedited by the dozen or so eyeball fuckings we gave each other up to that point. Meanwhile I was being (in retrospect) absurdly bashful, I'd never had a guy this sexy talk to me like that in this setting. Which made him smile even more and say shit like "don't be shy bud, I loved knowing you couldn't get enough of me, and obviously want my bod." And he'd make me say it out loud.

Then he told me to kiss him. And I did. Butterflies galore. Then he quietly said "I've got a really big cock" and nodded while holding eye contact with me. I stammered something like "um" and he just smiled and said he did, and he asked if I like big cocks, made me say it out loud, etc. He asked if I wanted to see it and I was like "HERE?" I mean, we were in the hallway, not the middle of the party, but still there were people everywhere. He kissed me again and grabbed my ass, which pushed me into him, and I could feel it. I moaned or groaned or otherwise made a sound that said it all. He took me by the hand and led me up a couple floors to the top of the stairwell, where it would open to the roof but it was locked. We made out some more than he unbuckled his pants and opened them and said something like "there you go bud" and said I could feel it or see it or do whatever I wanted with it, and that it was my cock tonight.

He was, if anything, being modest when he said he had a big cock. It was magnificent: long, thick, uncut, and his balls were big too. Easily one of the Top 5 cocks ever in my presence, and on a guy who is shorter than me and wiry, so it looked even more like a whopper. And that's when "Mr. I'm Not Hooking Up Tonight" blew Tony at the top of the stairwell. More like I made love to cock with my mouth. The whole time he was talking dirty too, encouraging me to enjoy his cock. I had his shirt unbuttoned and was massaging his hairy pecs and stomach, tweaking his nipples, sucking the hell out of his cock. When he said he was close I just looked up into his eyes and kept sucking, and he smiled and nodded and shot in mouth. I swallowed every drop like it was my favorite meal.

Then we went back to the party and rejoined our respective friends. Continued to make eye contact. When it was pretty late and my friends were getting ready to leave and calling Uber etc, Tony tapped me on the arm and said "let's have a drink before you go." So I made some excuse about getting my own ride, and followed Tony over to his loft, during which he explained he didn't have any wine or booze, but that he was recharged and ready to fuck my hole, and that he wanted to find out how many times I could make him cum. I left about 36 hours later lol.

This reminds me about an encounter I had with a guy when I first came out. I was still living in the small conservative town where I had grown up. But I had a few gay friends and 3 or 4 times a week we would travel an hour to a bigger town that had a gay bar. I didn't have a car at the time, so I relied on my friends for rides to the bigger town. We knew a lot of people in the bigger town, so quite often we would go to after hour parties and would end up spending the night at different friend's houses.

One summer night, a friend was moving to Chicago and they had a big going away party. The guy that gave me a ride to the party had planned on spending the night with his boyfriend. So I had made plans to spend the night at the house where the going away party was being held. It was a great night. Had a blast at the party. A majority of the people went to the going away party. It was a hot balmy night. I remember when the party was going strong it was getting warm inside the house. I went out to the front porch and the breeze felt great. There was already a group on the porch when I noticed a cute guy I had seen at the bar a few times. He was around my age (early 20's at the time), about 6 foot tall and around 150/160 in weight. He had short blond hair and the most amazing green eyes. And when I had seen him smile, he had the cutest dimples. The few times I had seen him at the bar, he was always hanging around the same people and they were always dancing or hanging out right next to the dance floor.

So when I was checking him out, he looked over towards me and got that cute smile with the dimple. Being a bit tipsy, I got up from where I was sitting and walked over towards him. I smiled and introduced myself. He told me his name (which for the life of me I don't remember). There wasn't any place to sit near him, so I motioned out to the front lawn and asked if he wanted to go sit out there and talk. He got up and said sure. We sat on the front lawn for a few hours as we chatted. The only time we got up was to refresh our drinks or to piss. Each time we went back to the front yard to sit down, and we would sit closer to each other. By the end of the night, we were sitting next to each other with our legs and arms touching. I felt really good and tipsy, I reached over and held his hand while we talked. He didn't pull away and leaned his body against mine.

While we were talking, I learned he was from a small town about 45 minutes away (in the opposite direction from me) and the people I had seen him with at the bar were his friends from the same small town he was from. They always car pooled together to the bar and usually they would leave the bar together. (That is why I hadn't seen him at any of the other after hour parties.) He said he was an artist and he did have that artist type of personality. He was cute and I had a great time chatting with him. But the party was winding down and I knew I would be passing out soon. I asked him where his friends were (since they usually car pooled together) and he told me that he went out with his friends but they left without him. He already had a ride home, but they wouldn't be able to pick him up until later in the morning. I told him I was spending the night at the house and he was welcome to share the bed with me. On the way upstairs to the bedroom, we said good nights to everybody. We got into the room and discovered it was a twin size bed. He got a smile on his face and said he was game if I was. I just smiled and said definitely! I started taking my clothes off when he asked how I slept. I told him I slept naked usually. I could keep some clothes on but it was warm and I wouldn't be able to sleep. He agreed that it was too warm to sleep in clothing. He said he was going to strip down to his underwear (which he had already done.) I laughed and said that would be fine but I was going commando that night. So with that, he took off his underwear and was completely naked. His dick was about 6" and not erect but getting bigger. That just made my dick start getting hard. I got in bed and scooted over to one side to give him some room. He got in bed and we pulled the sheet up.I was on my side, and he was laying on his back. I draped my arm over his body and felt his abs and chest. He had a nice hairy chest and I loved running my fingers through the hair. His hand was by his side, right next to my dick. I felt his hand reach up and start stroking my dick. I moved my hand down and grabbed his dick which by now had grown to full 8" size. We started making out while we played with each other's dicks. He was a great kisser and we were really getting into it. He got up and moved my body so I was laying on my back. He got on top of me and we started making out again. He moved down my body and stopped when he reached my dick. He sucked my dick for about 10 minutes before he started to push my legs up and started to rim me (that was a first for me!) He started to kiss me again, which I didn't know what to think about that after he had just rimmed me, but he was such a great kisser that I didn't mind it. While he was kissing me, I felt the head of his dick hitting my hole, I reached down and grabbed his legs and pulled him in, with that, he stopped kissing me, spit on his dick and pushed his dick into me. He felt so amazing as he went in and I was really getting into it. He took it slow at first, and it wasn't until he was all the way in that he slowly started to pull it back out. I put a pillow over my head because I realized I was moaning loudly. He held it with just the head of his dick inside me. I reached for his legs again and pulled him all the way in. When I felt his balls slap against me, I let go of his legs and he started to fuck me. We were making out again while he was busy fucking me. I knew I was getting close and told him I was really close. He stopped kissing me and began fucking me even harder. He was pounding my ass hard. And then I saw his eyes roll back in his head. With that, his rhythm stopped, he held his dick deep inside and I could feel it pulsing. That sent me over the edge and I started to shoot my load all over my chest. He collapsed on top of me and we were both short of breath and covered in sweat. After a few minutes, I got up and found a towel for us to wipe up with. We both fell asleep in each other's arms. The sun shining through the window woke me up about 8am. He was still asleep and I tried my best to get out of bed without waking him up. I almost made it out of bed when he pulled me back down and started kissing me. He looked at his watch and realized his ride would be there soon. We exchanged numbers and said our goodbyes.

I later found out we had been a little bit loud last night, everybody heard us having sex. We talked on the phone a few times, we would meet at the bar on weekends. But I didn't have a car at the time and his van wasn't reliable. A few months later, he moved out west to start a new job. I never saw or talked to him again. It was a very unexpected but fun encounter.