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

[PigBoyDallas]

Had a hook up with this really cute chubby but twinky blonde kid last week. He's 18, but has a 20 y/o BF who goes to SMU and they are pretty open. He's super hot and we did raw, he didn't ask my status, wasn't about to ask his and we swapped loads. He said he and his BF sometimes do three ways but his BF doesn't bottom but does BF likes Latino guys. He wanted to see if I'd be interested in a three way. I had to stifle shock and laughing when he showed me his BF's pictures as I've been playing with his BF off and on and he's a raw pig like me and his boy. His BF is NOT all top as I've bred his ass raw plenty. I said sure...kinda want to see the shock on his BF's face when he sees I've been pounding his boy's ass raw.

[faggot4play]

7 minutes ago, PigBoyDallas said:

Had a hook up with this really cute chubby but twinky blonde kid last week. He's 18, but has a 20 y/o BF who goes to SMU and they are pretty open. He's super hot and we did raw, he didn't ask my status, wasn't about to ask his and we swapped loads. He said he and his BF sometimes do three ways but his BF doesn't bottom but does BF likes Latino guys. He wanted to see if I'd be interested in a three way. I had to stifle shock and laughing when he showed me his BF's pictures as I've been playing with his BF off and on and he's a raw pig like me and his boy. His BF is NOT all top as I've bred his ass raw plenty. I said sure...kinda want to see the shock on his BF's face when he sees I've been pounding his boy's ass raw.

hot story........

[SamCummyCunt]

Happened to me.  Hot sex w/me getting to eat the hottest ass I've eaten in years turned even hotter when he whimpered and slid my cock into his ass raw and let me do him to my heart's content.  He said I smelled rank (I had just come from working out) and it turned him on.  In the afterglow I made a comment about a hat with a logo I recognized and soon we were discussing our mutual friendship w/someone very close to our friend group in a city hundreds of miles away.  Oh, and this dude was from my hometown as well. Small, small world.

[Staples]

Closest to getting "caught" was going over to this guys house off of Craigslist. He had a swing and all this leather stuff and I was like 20, and he invited this other guy and didn't tell me. I couldn't take his cock and wasn't interested in the other guy so I just kinda third wheeled it and left.

Like within a week I saw the other guy at a gym and ran out and never went back. 😁

[versamarried]

I mentioned this recently in another thread. I had met up with a top who had hyperspermia, though he just referred to it as shooting big loads. Neither of us had not heard the term hyperspermia at that time. Anyway, first couple of times we met it was always under the pretense that I was just going to suck him off, but instead I always seduced him to fucking me and shooting his massive load deep in me. Then I would run to the bathroom and jerk off with his load just pouring out of me, using it as more lube for my cock before I would shoot into the toilet (where my bottom ass cum belongs). After about the third meetup cue both our massive surprise looks as my wife and I brought our dog in for grooming and he was the head groomer of the location. We silently acknowledged one another. Afterward at our next meetup he asked if my wife was aware I fuck guys bareback. I said no I am dirty cheater. He came so much in me that it was leaking out of me as he was shooting. He said he was worked up thinking about how he and my wife saw each other and she had no idea that I carry his baby makers deep in my guts. Unfortunately he moved away and stopped managing that location. But he was the one top that made me shift from versatile to full time cheating bareback bottom.

[Cumjunky215]

Years ago in a relationship my bf belonged to a local gay basketball team. They practised at a local Y  convenient having shower and lockers there.  I went a few times to watch and remember a new member playing but he kept to a tight small circle of players. Sometimes most of the players went out for something to eat or drink, this guy rarely joined in.  He was easily the handsomest guy.  BF and I break up after a few years. I go online to a cruise site and a blank profile--like mine-- he texted for a blind fuck, walk in find me blindfolded ass-up to take his dick.  We did this a few times, almost total silence, he enters strips and uses my mouth to get hard then breeds me.  Fit body, not a quicky, few words. I asked if I could feel his balls when he's inside me and I held them all the time feeling his babies cum into me.  After about 6th fuck we both mentioned that it was great and want to keep meeting. He said I could remove the blindfold. I immediately recognized him, he knew nothing about me.  He fucked me for months after but he never knew I knew him from before.

[Njn0mc]

I have on occasion meet up with someone at a new location and when he answers the door we recognize each other.

A while back i went to a parTy and there was a few guys there. I didn't realize untill one of them was fucking me when I was on my back and saw his face that we played before. Has he was pumping he stopped and laughed and said hey I know you then pumped even harder.

 

[inmyass262]

When I was in my early 20’s I went to one of the adult book store gloryholes near my hometown while visiting family. An older guy stuck a fairly large uncut cock through the massive square gloryhole. I was nude and started sucking him off and offered my ass to him. He slid in my ass and started to fuck me but he had to stop because it was hurting his back. We agreed to go to the buddy booth so I picked up my clothes and followed him nude to the booth. I went in and locked the door and when I turned around it was the guy who owned the hobby shop I used to frequent all the time as a kid. He recognized me and got all nervous but I sat on his lap and rode his cock until he pumped his load in my ass. We made out some before we went outside and sat in his van and he sucked me off. 

[Aidsbait]

one time i was in a porntheatre fully naked on my hands and knees getting throatfucked and assfucked by a series of horny straight guys, regulars, random pigs and homeless men. i had started that visit by sucking off several men in the booths while nude before going into the wideopen theatre. i didnt bother putting on any clothing or wiping the cum off my face between the booth and the theatre so severeal guys actually saw the cum all over my face. one guy actually asked what was on my face and when i said cum, he asked whos and i told him i have no idea but it was several loads. so while i was down onmy hands and knees on in the dirty porntheatre getting my ass repeatedly fucked and bred i still had cum on my face. i stayed for couple hours and got fucked by about a dozen strangers (i went at a busy time). the third last guy turned out to be my boyfriend. he fucked me then said “take my load you fucking whore” and i recognized his voice and turned around. he just pulled out and left while the next guy mounted me. i stayed and took loads from the last few guys. turns out he went in to get a quick blowjob and found me in there getting used and decided to watch 7 men fuck me before he couldnt resist. he said he knew i was a slut but had no idea i go places like that and let strangers run a train on me. he was pissed at first but admitted it turned him on. so the next week he started taking me to bathhouses and porntheatres regularly to watch randoms breed me. soon after he started posting dirty ads and whoring me out online on a regular basis.

[Guest]

I blocked a guy on dating app because he was annoying and his profile was blank, and only dick picture as his profile avatar, 2 days later he contacted me from another account and offered $ for a blowjob, so I invited him in, I didn't know he was the same guy, he told me just after finishing in my mouth. 

[austin_submale]

1 hour ago, Tsjul said:

I blocked a guy on dating app because he was annoying and his profile was blank, and only dick picture as his profile avatar, 2 days later he contacted me from another account and offered $ for a blowjob, so I invited him in, I didn't know he was the same guy, he told me just after finishing in my mouth. 

Did that end up badly or was he OK after that?

[Guest]

13 minutes ago, austin_submale said:

Did that end up badly or was he OK after that?

I actually hated the guy, but business is business. 

[partying.hard]

I was traveling on business.  I was in town several nights.  Hooked up on an app.  He came to my hotel.  We slammed, and I had my fist up his ass.  Suddenly, his eyes got huge and his whole clamped down on my wrist. He gasped, and said “are you the guy who presented over at the university yesterday?“  I leaned down, kissed him, winked, and told him this was going to be better!

[YayForMe]

On 5/20/2023 at 9:15 PM, 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. 

So hot!

[Warmnsalty]

My only story was when I was regularly sucking and getting fucked by a college guy in my town. Met on Grindr, He was a senior lived with his gf off campus. He'd hit me up once or twice a month to suck him off or fuck me. After several months of me being his on call cum slut, wife and I and kids were at a popular pizza place, in walks in my guy and his girl. He and I made eye contact, nothing more. LOVED watching his cute gf and knowing that I was getting some of the loads she should have been getting.