Stories about a hookup that turned out to not be random?

[BurnAfterReading17]

Curious if any of you have gone and had sex with someone that turned out to be closer to your circle than you thought? 

 

An example:

I was in LA for work. I flew in the Friday before so I would have the weekend to hang with friends. That Saturday night I was out with a buddy, had a couple drinks and a gummy that got me going. 

Unlike NYC, LA closes down or starts to around 2am.

My friend went home and I back to my hotel. Curiosity had me on grindr before I was out of the elevator. 

The great thing about traveling is you can have a blank profile (not recommending) and still get a bunch of hits. The algorithm is in your favor. 

I took a quick shower and made sure I was good...just in case. With no real intention to hook up, some times I just like the attention. 

One guy, headless torso, was in the hotel across the street from me. In town for work, not single, insists on playing safe "if it gets there." All the things I like to hear. 

 

He asked if I wanted to come over. I told him I was already in bed, in my underwear and sent him a photo looking down my body to my briefs and my spread legs as a tease. 

He messaged back with a dick Pic, asking what I wanted him to do to me. 

 

"well, may favorite thing is to beat off while hitting poppers with a guy between my legs teasing my hole with his dick" I fired back. 

That got me a double fire reaction. "only teasing or can I push in?" 

"if I take a big hit of poppers and you felt the urge to push the tip in... I wouldn't be mad."

"just the tip?" he asked. 

"well, if you wanted more than the tip you have to wrap it up," I confirmed. 

"of course, I only play safe" he reminded. "what room are you in?" 

I was tipsy and still rolling from the gummy (I know I'm a lightweight). My heart started beating fast and I text him my room number. Then I went to my bag to unpack my sex kit to realize it wasn't in my bag. 

"I don't actually have my stuff, no condoms, poppers or lube" I messaged real quick. 

"no problem," he said. "on my way." 

Within minutes he was at my door with a sexy grin because I answered in just my Aero briefs. 

Not chatting, his hands went to my hips and started kissing me before the door was closed. We stumbled to the queen sized bed and I fell backwards into it, him on top of me, spreading my legs wide as we shuffle to the center of the bed. His clothes flying off quickly, then he yanked my briefs off, tossing them aside and they landed on the weird lamp in the corner of the room.

He resumed kissing me for a minute, then reached back for his sweatpants to grab some poppers out of his pocket. It was a new bottle and he managed to rip that seal off with his teeth and then passed them to me for the first hit. 

It was strong, I just lay there and enjoyed the rush of the new bottle as he positioned himself to close the gap between my ass and his dick. Rubbing the fat, leaking head of his uncut 7.5" rock hard dick up and down my crack, searching for my hole. As soon as he grazed over it I let out a soft moan. 

"yeah, you like that?" 

"yeah," I moaned and started stroking my dick. Rocking my hips on his cock as he jerked himself off on my hole. Both of us moaning and enjoying the feeling of each other's sex parts and all of the touching we don't normally do with strangers. 

Another hit of the poppers and I felt him add spit to his cock and try to push the head in, but I'm too tight and he just keeps teasing. 

A few minutes later he pushed a pillow under my ass drops down and starts running my hole. I moan softly, running my fingers through my hair, jerking off with the other hand as my ass clenches and relaxes around his tongue as it gets a little deeper with every flex. Fuck it felt good, an expert ass eater. 

He pops back up and grinds against me, spreading my legs further apart, letting his cock slip into my now wet hole. I quickly took a deep hit, then another of the poppers and passed it to him to inhale. 

He took a long hit and then passed it back as he added pressure to my hole with his cock head I took another hit and felt the incredible pressure of his head popping into my hole.. 

I the my head back into the pillow and let out a louder moan, flexing my hole on his cock. He moaned with me and started stroking my cock for me as I enjoyed all the pleasure running through my body all at once. 

His one hand stroking my dick slowly, the other massaging my thigh and the space between my balls and hole. It felt amazing! 

As he stroked me he rocked his hips a little, "you like that?" he moaned. 

I nodded my head and let out a gaging "yeah" and placed my palm on his lower abs to remind him not to push all the way in. 

We rocked and moaned in pleasure for a few minutes and then he grabbed the poppers and leaned into me, helping me take another hit and not so subtly getting another inch into my tight hole. I took the hit and then the other side, the rush rolling over me like a wave. Both my hands running throb my hair as I enjoyed more of his big dick, sliding in with ease thanks to his precum. 

"fuck" I breathed out, feeling him spread my legs and deliberately ride that wave with me another inch deeper and then another. 

"fuck you're tight," he whispered as he bottomed out inside me. 

I smiled in bliss, "fuck dude, that feels so good." 

I felt him flex his dick inside me, "yeah real fucking good." 

He learned in, getting even deeper into me as he came in for a passionate kiss and started slowly rocking his hips into me. Moaning with me. 

My arms around his back pulling him in, I felt so good, the muscles in his back flexed as his hips curled his dick deeper into me. "fuuuck", I moaned, bragging the kiss he went straight to sucking my neck and I moaned. "did you bring the condom?" 

"I didn't have any," he whispered, still rocking his dick inside me. 

We both enjoyed a moment of knowing we had two choices, stop our continue. As he continued rocking his hips, deeper and harder with each thrust, his gentle curve hitting that spot inside me. 

" Can I fuck you raw?" he asked and kissed my neck without skipping a thrust. 

"You said you don't have anything right?" I wrapped my legs around his taught waist. 

"yeah," he shifted his weight to shift into a fucking position in the smoothest transition I've ever experienced. 

"fuck, don't stop", I whispered, wrapping my arms around him as he started to fuck me. 

"you sure?" he asked, full on fucking me now. 

"fuck yes, this feels so good," I moaned. 

He kissed me and fucked me firm but sensually, moaning with pleasure. His body in sync with mine, it felt amazing. 

He put sat up, putting my legs on his sculpted shoulders, he took another hit of poppers and passed them to me, starting to fuck me harder before I even had a chance to take another hit, but I did.

He slowed after a minute, deep dicking me, "take another hit."

He let my legs drop as I took a hit, he leaned in and I helped him take a hit as he slowly fucked me. I took one more then caped it and just enjoyed the sensation of his cock sliding in and out of my hole. 

"can I cum in you?" he asked and kissed my neck. 

I hesitated, thinking I should say no. 

"you feel so good, don't make me pull out, it won't feel as good," he kissed my neck, thrusting hard and deep into me. 

I didn't say anything, just enjoying his last few thrusts, "I'm about to nut man," he warned. Thrust, thrust, he lift his head and looked me in the eyes, "I'm going to cum in you" and I saw his face as his orgasm took over, felt his cock swell and spasm as he unloaded inside me. "oh fuuuuck" he grunted as his entire body flexed inside and on me, curling his hips to get his dick as deep as possible while he nut inside me "and then collapsed on me. 

His sweaty body relaxed on me as he caught his breath and his dick slowly went limp and slid out of me. He rolled off of me with a soft," holy shit that felt good ". 

Minutes later he got up and quickly dressed.

"I'll be in town all week for work if you want another round," he smiled, pulling on his shirt. 

"I have a busy week, but maybe," I told him. 

He left and I showered. 

Sunday was a recovery day, chillen by the pool and jerking off a few times thinking about the night before. 

Monday came, I went to work and had a few meetings with producers. Then I was introduced to the crew, the audio guy, who's name is Cole, introduced himself to me with a grin. He had every right to grin, he fucked me like a pro Saturday night and blew his load inside me. Now I'm working with him for a week. 

Edited May 21, 2023 by BurnAfterReading17
Typo

[Nowwhat007]

3 hours ago, BurnAfterReading17 said:

Curious if any of you have gone and had sex with someone that turned out to be closer to your circle than you thought? 

 

An example:

I was in LA for work. I flew in the Friday before so I would have the weekend to hang with friends. That Saturday night I was out with a buddy, had a couple drinks and a gummy that got me going. 

Unlike NYC, LA closes down or starts to around 2am.

My friend went home and I back to my hotel. Curiosity had me on grindr before I was out of the elevator. 

The great thing about traveling is you can have a blank profile (not recommending) and still get a bunch of hits. The algorithm is in your favor. 

I took a quick shower and made sure I was good...just in case. With no real intention to hook up, some times I just like the attention. 

One guy, headless torso, was in the hotel across the street from me. In town for work, not single, insists on playing safe "if it gets there." All the things I like to hear. 

 

He asked if I wanted to come over. I told him I was already in bed, in my underwear and sent him a photo looking down my body to my briefs and my spread legs as a tease. 

He messaged back with a dick Pic, asking what I wanted him to do to me. 

 

"well, may favorite thing is to beat off while hitting poppers with a guy between my legs teasing my hole with his dick" I fired back. 

That got me a double fire reaction. "only teasing or can I push in?" 

"if I take a big hit of poppers and you felt the urge to push the tip in... I wouldn't be mad."

"just the tip?" he asked. 

"well, if you wanted more than the tip you have to wrap it up," I confirmed. 

"of course, I only play safe" he reminded. "what room are you in?" 

I was tipsy and still rolling from the gummy (I know I'm a lightweight). My heart started beating fast and I text him my room number. Then I went to my bag to unpack my sex kit to realize it wasn't in my bag. 

"I don't actually have my stuff, no condoms, poppers or lube" I messaged real quick. 

"no problem," he said. "on my way." 

Within minutes he was at my door with a sexy grin because I answered in just my Aero briefs. 

Not chatting, his hands went to my hips and started kissing me before the door was closed. We stumbled to the queen sized bed and I fell backwards into it, him on top of me, spreading my legs wide as we shuffle to the center of the bed. His clothes flying off quickly, then he yanked my briefs off, tossing them aside and they landed on the weird lamp in the corner of the room.

He resumed kissing me for a minute, then reached back for his sweatpants to grab some poppers out of his pocket. It was a new bottle and he managed to rip that seal off with his teeth and then passed them to me for the first hit. 

It was strong, I just lay there and enjoyed the rush of the new bottle as he positioned himself to close the gap between my ass and his dick. Rubbing the fat, leaking head of his uncut 7.5" rock hard dick up and down my crack, searching for my hole. As soon as he grazed over it I let out a soft moan. 

"yeah, you like that?" 

"yeah," I moaned and started stroking my dick. Rocking my hips on his cock as he jerked himself off on my hole. Both of us moaning and enjoying the feeling of each other's sex parts and all of the touching we don't normally do with strangers. 

Another hit of the poppers and I felt him add spit to his cock and try to push the head in, but I'm too tight and he just keeps teasing. 

A few minutes later he pushed a pillow under my ass drops down and starts running my hole. I moan softly, running my fingers through my hair, jerking off with the other hand as my ass clenches and relaxes around his tongue as it gets a little deeper with every flex. Fuck it felt good, an expert ass eater. 

He pops back up and grinds against me, spreading my legs further apart, letting his cock slip into my now wet hole. I quickly took a deep hit, then another of the poppers and passed it to him to inhale. 

He took a long hit and then passed it back as he added pressure to my hole with his cock head I took another hit and felt the incredible pressure of his head popping into my hole.. 

I the my head back into the pillow and let out a louder moan, flexing my hole on his cock. He moaned with me and started stroking my cock for me as I enjoyed all the pleasure running through my body all at once. 

His one hand stroking my dick slowly, the other massaging my thigh and the space between my balls and hole. It felt amazing! 

As he stroked me he rocked his hips a little, "you like that?" he moaned. 

I nodded my head and let out a gaging "yeah" and placed my palm on his lower abs to remind him not to push all the way in. 

We rocked and moaned in pleasure for a few minutes and then he grabbed the poppers and leaned into me, helping me take another hit and not so subtly getting another inch into my tight hole. I took the hit and then the other side, the rush rolling over me like a wave. Both my hands running throb my hair as I enjoyed more of his big dick, sliding in with ease thanks to his precum. 

"fuck" I breathed out, feeling him spread my legs and deliberately ride that wave with me another inch deeper and then another. 

"fuck you're tight," he whispered as he bottomed out inside me. 

I smiled in bliss, "fuck dude, that feels so good." 

I felt him flex his dick inside me, "yeah real fucking good." 

He learned in, getting even deeper into me as he came in for a passionate kiss and started slowly rocking his hips into me. Moaning with me. 

My arms around his back pulling him in, I felt so good, the muscles in his back flexed as his hips curled his dick deeper into me. "fuuuck", I moaned, bragging the kiss he went straight to sucking my neck and I moaned. "did you bring the condom?" 

"I didn't have any," he whispered, still rocking his dick inside me. 

We both enjoyed a moment of knowing we had two choices, stop our continue. As he continued rocking his hips, deeper and harder with each thrust, his gentle curve hitting that spot inside me. 

" Can I fuck you raw?" he asked and kissed my neck without skipping a thrust. 

"You said you don't have anything right?" I wrapped my legs around his taught waist. 

"yeah," he shifted his weight to shift into a fucking position in the smoothest transition I've ever experienced. 

"fuck, don't stop", I whispered, wrapping my arms around him as he started to fuck me. 

"you sure?" he asked, full on fucking me now. 

"fuck yes, this feels so good," I moaned. 

He kissed me and fucked me firm but sensually, moaning with pleasure. His body in sync with mine, it felt amazing. 

He put sat up, putting my legs on his sculpted shoulders, he took another hit of poppers and passed them to me, starting to fuck me harder before I even had a chance to take another hit, but I did.

He slowed after a minute, deep dicking me, "take another hit."

He let my legs drop as I took a hit, he leaned in and I helped him take a hit as he slowly fucked me. I took one more then caped it and just enjoyed the sensation of his cock sliding in and out of my hole. 

"can I cum in you?" he asked and kissed my neck. 

I hesitated, thinking I should say no. 

"you feel so good, don't make me pull out, it won't feel as good," he kissed my neck, thrusting hard and deep into me. 

I didn't say anything, just enjoying his last few thrusts, "I'm about to nut man," he warned. Thrust, thrust, he lift his head and looked me in the eyes, "I'm going to cum in you" and I saw his face as his orgasm took over, felt his cock swell and spasm as he unloaded inside me. "oh fuuuuck" he grunted as his entire body flexed inside and on me, curling his hips to get his dick as deep as possible while he nut inside me "and then collapsed on me. 

His sweaty body relaxed on me as he caught his breath and his dick slowly went limp and slid out of me. He rolled off of me with a soft," holy shit that felt good ". 

Minutes later he got up and quickly dressed.

"I'll be in town all week for work if you want another round," he smiled, pulling on his shirt. 

"I have a busy week, but maybe," I told him. 

He left and I showered. 

Sunday was a recovery day, chillen by the pool and jerking off a few times thinking about the night before. 

Monday came, I went to work and had a few meetings with producers. Then I was introduced to the crew, the audio guy, who's name is Cole, introduced himself to me with a grin. He had every right to grin, he fucked me like a pro Saturday night and blew his load inside me. Now I'm working with him for a week. 

Please please write more of what happened, if you guys ended up meeting up some more. Went through your posts.. they're 🥵🥵🥵  thank you for spending time and sharing them

[BurnAfterReading17]

20 hours ago, Nowwhat007 said:

Please please write more of what happened, if you guys ended up meeting up some more. Went through your posts.. they're 🥵🥵🥵  thank you for spending time and sharing them

Nothing more happened with him. The entire project was very demanding and we both acted very professional and then he flew out on a red-eye immediately after we wrapped. 

 

I'm really just curious if any one else has run into similar situations of "oh that's the guy I had sex with who's name I don't know" that you had to spend time with and act like you didn't have sex. I've had many situations where people hit me up on grindr with their explicit photos and then I see them in person waiting on the subway the next morning dressed all professional and I think to myself, "I have seen your asshole" and we both act like that's not how we know each other. 

Maybe that's only common to places like NYC. 

[Nowwhat007]

So far, never happened to me. Although, I don't really go out there, as much. I have a small circle and don't really hook up much either 😅 but I always think of this when I see profiles on hook up apps lol

[NWUSHorny]

It happens, luckily I haven't had one that tried to use it against me in any way. The biggest incident happened over 20 years ago, I fucked a guy at the bathhouse, multiple times both Friday and Saturday night, on Monday morning I started a new consulting project and found out he was the IT director I would be working with for the next couple of months. We didn't fuck again, for several years.

[IntoBBvisitor]

Something similar happened to me...

 

 

[Close2MyBro]

Years ago I met a chubby latin guy on Craig's list who just wanted a regular cocksucker to choke on his fat 8" uncut dick and guzzle his cum. He told me he was married and just wanted some action on the side and that it would be great if I was free at the last minute because he couldn't always play ahead. After numerous attempts to meet that didn't work out, we finally managed to hook up and he decided to make me his regular go-to cocksucker. For the next three years or so we'd arrange to meet up every two to three weeks and he'd fuck my face, blow his load and go.

A staff member of mine invited us to a birthday party for her five year old daughter, and all my staff decided to go, so I went. She introduced us to her husband, who happened to be the guy I had been sucking off for the last few years. We pretended that we'd never met before and after the party that night I got an email from him saying that now he knew that I was his wife's boss, it turned him on even more and now he wanted me to suck his dick even more than before. At our next meeting he told me his wife was a terrible cocksucker and after that it became a weekly thing for me to suck his dick and swallow his load. That went on for another two years before they moved across town to a larger house and it became pretty irregular after that and then she quit and took another job and we lost touch.

[Guest]

I posted an ad on CL looking for a cock to suck in my remote corner of WA. Met a sexy AF bald biker about my age at a discrete place in the woods near both our houses. Worshipped his cock and swallowed his load.  Just met that one time until....

My son wants us to meet his new GFs parents at a BBQ they're hosting, and you already guessed who her dad was.  🙂

Just casually introduced ourselves and never talked about it.  (His daughter is an absolute and utter trainwreck of a human being, no joke or exaggeration, but we're stuck with her as they had kids together.)

[Breedingandseeding]

Couple months ago got sucked off by a 20 year old Latino who game amazing head. Great stamina and he milked 3 back to back loads from me. He was kind of annoying though, talked too much before and after (I had to pick him up and bring him to my place because he couldn’t host and didn’t have a car). A few weeks pass and I didn’t meet up with him again because he seemed like the type to get attached. One day my brother, my brother who lives nearby and I are hanging out and go pick up some fast food with me driving. As I pull up to the drive through window, I have a moment of shock when I realize that annoying twink with the heavenly oral skills is the guy at the cash register. I have a moment where I panic and think he might make a not entirely subtle remark or attempt to flirt while my brother is seated next to me. Ends up asking me to pull over into the parking lot because our order will take a few minutes and they don’t want to hold up the line. Eventually he brings out our food and fortunately doesn’t say anything but definitely had a smile on his face.

now that I’m thinking about it I’m tempted to face fuck the guy again…

[polyglutton]

On 5/20/2023 at 10:08 PM, Nowwhat007 said:

Please please write more of what happened, if you guys ended up meeting up some more. Went through your posts.. they're 🥵🥵🥵  thank you for spending time and sharing them

Very hot and well-written. Thank you. 

[pozsewerpig]

This happened when I was a college senior.  I went to an ABS downtown and hit the booths around 6 pm. A guy around 30 years old was in the booth next to me. He was wearing a suit and tie and had his dick out while stroking it. I motioned him over to give a blow job through the gloryhole. His dick was average and he lasted an average amount of time before I received a mouthful of cum as a reward for my efforts. He zipped up and left.

Cut to a few days later when I went for an interview for a real job for my post-graduation life. Of course he was one of the three people on the panel interviewing me. I didn't notice if he was wearing a wedding ring at the ABS, but he definitely was during the interview.  And I didn't get the job.

[Breedingandseeding]

40 minutes ago, pozsewerpig said:

This happened when I was a college senior.  I went to an ABS downtown and hit the booths around 6 pm. A guy around 30 years old was in the booth next to me. He was wearing a suit and tie and had his dick out while stroking it. I motioned him over to give a blow job through the gloryhole. His dick was average and he lasted an average amount of time before I received a mouthful of cum as a reward for my efforts. He zipped up and left.

Cut to a few days later when I went for an interview for a real job for my post-graduation life. Of course he was one of the three people on the panel interviewing me. I didn't notice if he was wearing a wedding ring at the ABS, but he definitely was during the interview.  And I didn't get the job.

Surprised you’d recognize him from meeting once at a gloryhole. I’ve only been to public gloryholes twice but both times I wouldn’t have been able to recognize the guy on the other side if I had seen him a few days later (hole was just large enough for cocks to get through)

[pozsewerpig]

19 minutes ago, Breedingandseeding said:

Surprised you’d recognize him from meeting once at a gloryhole. I’ve only been to public gloryholes twice but both times I wouldn’t have been able to recognize the guy on the other side if I had seen him a few days later (hole was just large enough for cocks to get through)

1. The gloryholes were decent-sized back in the day and you could see plenty of what was going on next door. 2. He put on a show for me while stroking prior to feeding me his dick. 3. He had very distinctive eyes and was one of those going bald early guys. 4. The ABS was about 2 blocks from his office. 5. I stand by my stance that this was the same guy that interviewed me a few days later.

[Breedingandseeding]

42 minutes ago, pozsewerpig said:

1. The gloryholes were decent-sized back in the day and you could see plenty of what was going on next door. 2. He put on a show for me while stroking prior to feeding me his dick. 3. He had very distinctive eyes and was one of those going bald early guys. 4. The ABS was about 2 blocks from his office. 5. I stand by my stance that this was the same guy that interviewed me a few days later.

Cool, wasn’t doubting you, was just curious. Do you think he recognized you too then?

[pozsewerpig]

49 minutes ago, Breedingandseeding said:

Cool, wasn’t doubting you, was just curious. Do you think he recognized you too then?

I think he did. While he was putting on a show for me, my face was probably pretty visible through the hole. The introductory handshake at the interview was pretty awkward as well.