Sex with an Ex?

[Acechaser]

Ex sex can be great and familiar. Once you've been inside me, you kinda always have a pass to get back in. I've had a lot of sex with exes

[tighthole64]

I was with my first boyfriend for 3 years before he decided party drugs were more of a priority.  It really hurt as was my first true love.

He later got a new BF and moved to Georgia.   We still remained friends, and also became friends with his new partner.  They invited me up to join them on their boat to which I accepted.  Had no idea it would become a 3 way.  His new partner coyly said I know how you missed each other, and suggested we go below deck and have some fun.  I was suprised, but we both did.  Shortly after we started, his new partner came down completely naked, and joined in!

His partner also got us some Club Seats for a football game around Christmas.   My X And I fooled around in car before, and even had some restroom fun.  Afterwards we went to a bar, and sadly got totally shit faced.  Had to call his partner to come get us!  If we hadn't got drunk, sure we would have had another 3 way!

[BurnAfterReading17]

 

So this guy wasn’t an ex-boyfriend per se. In my “blank profile” days on Grindr, I was still very much in denial about my sexuality and so far in the closet you could’ve turned on a light and you wouldn’t find me. But this guy was a sort of regular hookup back in those days.

I wouldn’t say “regular” in that we fucked often, but since literally all of my previous m/m sexual encounters had been a one-and-done situation, I would say more than once at this point was regular.

Russell had a weird chip on his shoulder about me claiming to be straight and just horny. Today, I get it, but at the time it was annoying that he couldn’t just accept it. It was frustrating to me and clearly frustrating to him. He would ask me every time we met up if I had come out yet. I would tell him the same story I told him every time, no.

Again, I want to stress that we only had sex maybe 4 times, and one backseat blow job where he nut in my mouth and it really freaked me out. I didn’t reach out to him again after that.

Four years later Facebook actually recommended we be friends, so I clicked. He was about 5 years older than me, probably closing in on 30 at this point, and had clearly been hitting the gym since I last saw him.

He popped up on messenger, asking what I was up to and why I asked to be friends. I told him it was the algorithm and curiosity. He then jumped right into, “Did you come out yet?” and I was instantly not interested anymore. I told him no and then pretended to be busy and bounced out of that conversation.

About 2 years after that, I had started coming out as bi to my close friends, but only the gay ones. Mostly because I had gotten drunk at a gay bachelor party and hooked up with one of the guests who just assumed I was gay if I was there and one of the bachelors walked in on the sex and naturally had questions the next morning (but that’s a different story).

So here we are, I’m about 27 at this point and out at a bar not far from my place celebrating the birthday of one of my closest gay friends' boyfriend. He had invited a bunch of people I didn’t know from his office. To my surprise, one of them is my Grindr friend Russell. From the look on his face, he’s equally surprised to see me. When introduced we smile and do the “nice to meet you,” without telling anyone we know each other.

Throughout the night we all get pretty drunk and Russell is always catching my eye. I’m not sure if he’s looking at me or if I’m looking at him, but we didn’t really talk at all.

The birthday boy leaves, along with his boyfriend (my friend), leaving me with a couple people I kind of know and a few people I don’t really know at all.

The group squeezes into the empty seats, Russell now seated right next to me. He man spreads and his leg is flush against mine. We are all talking, getting to know one another, the “well how do you know the birthday boy” question goes around like herpes. “Where do you live,” was another popular one. Turns out Russell has moved to Staten Island, which is a hike from where I’m at in Manhattan only a few blocks from the bar. When the question comes to me I casually mention I’m only a few blocks from here and make a point of *not* making eye contact with Russell, but I feel his stare burning a hole in me.

A round of shots and drinks later, I’m pretty wasted. I go take a piss, then to the bar to cash out. Russell is already signing his receipt.

“Heading out?” he asked.

“Yeah, ready for bed,” I joked.

“You asking me to join you?” He half joked.

I signed my receipt and looked up to meet his eyes, he was as drunk as I was.

“You didn’t drive did you?” I asked.

“I did,” he said.

“Well, you can’t drive home. You want to crash at my place? I asked.

He looked around, “do you want me to come over?”

I laughed, “I’m offering you my couch.”

“Boo,” he joked.

“I’m heading out now, are you staying?” I asked.

“I’m going with you,” he said.

We walked the few blocks to my place, riding the elevator in awkward silence. 

I let him in, the apartment was dark and quiet. It was a one-bedroom, but small, and shaped weirdly. The bedroom barely had room for a queen-sized bed and you couldn’t get the door to fully close because of it. You could only access the bathroom through the bedroom, and because of the bed you had to barrel roll over it to get the the bathroom. The living room/kitchen was all of 20’x7’, with just enough room for the couch and a coffee table and nothing else.

“You can crash on the couch or cuddle with me, up to you,” I told him. “I’m going to hop in the shower real quick.

I took a quick shower just to wash off NYC before getting in bed. Russell took the shower next.

I put on a pair of army-green briefs and face-planted in the bed.

A few minutes later I heard the water turn off. Russell came out. I half rolled onto my side and turned my head to see him, toweling off but otherwise naked. His body was much more cut than it was years ago when we hooked up. He smiled when he noticed me checking him out.

“Like what you see?” he asked.

 I got a little embarrassed and put my head back in the pillow. I mumbled something like, “sort of.”

I felt him climb onto the bed, then he climbed on top of me. I felt his naked body flush against mine, he’s bigger than I am in every way so he fully covered me. His weight felt nice and comforting, his hardening dick rubbing between my ass cheeks got my heart beating. The only thing between us was the thin layer of fabric of my briefs.

“What are you doing?” I mumbled into the pillow.

He felt up my body and dry humped me, “mmm, you going to give me this ass again?”

“I’m too tired,” I mumbled.

I felt him sit up, straddling my ass, massaging it with his hands. It felt good, I let out a little moan.

“Come on man, old time sake and all that,” he said, massaging my lower back down to my ass, letting his hands slide under my briefs so he could continue his massage.

“uh ah,” I groaned but didn’t push him off.

He tried to tug my briefs down but my hard dick kept them in place and I wasn’t trying to help him on this quest. I really was tired and drunk, not to mention I wasn’t really into him after our last hookup.

He had freed my butt cheeks and was boldly feeling them up, spreading them apart and breathing heavily as he enjoyed the view.

I felt his weight shift and he leaned down, his tongue suddenly lapping at my hole. I couldn’t help but moan. I wasn’t trying to get fucked, but I’d certainly let him eat my hole. He had never eaten my hole back in Brooklyn, this must be a new skill he picked up over the years, damn it felt good. I couldn’t help but let my hole loosen enough to let his tongue really get inside my hole.

“mmm, fuck,” I moaned into the pillow that I was now hugging.

“Your hole is still so tight,” he said and then continued eating.

A few more minutes of getting my hole eaten and he shifted his weight again, suddenly his dick was sliding across my spit-covered hole.

“What are you doing?” I asked, muffled by the pillow.

“I really want to fuck you,” he humped gently across my hole.

“Mmm, nah man,” I groaned.

“Come on dude, I’ll be quick,” he pleaded.

I laughed, “so not much has changed,” I joked.

“Fuck you dude, let me get inside, I’m so horny I really will cum in a few pumps,” he said, spreading my ass and letting his dick head push on my hole.

“ugh…” I groaned, annoyed and horny. “Fine,” was all I said, resigned to the fact that this was not going to be for me but to get him to go to sleep.

“Where are your condoms?” he asked.

I vaguely pointed behind him, “on the dresser with the lube.”

He leaned over, “There’s lube, but I don’t see any condoms.”

“Try the drawer?” I shrugged.

He pulled open the top drawer, “underwear, tic tacs, poppers, and socks, but I don’t see any condoms.”

“Give me the poppers,” I said, sitting up on my elbows.

He handed them to me and I quickly took a hit, then another, then tried to offer him some.

“Nah, thanks. Do you have any in your bathroom?” He asked.

“No, if there are none in the drawer then I’m out, you don’t keep one in your wallet?” I asked.

“I’m not fifteen,” he laughed, climbing back on the bed, sliding his hard dick across my hole again while holding himself up in a pushup position.

“What are you doing?” I asked.

“I could fuck you raw,” he suggested, with a tone that made it sound like he was doing me a favor.

I laughed, turned my head to look at him over my shoulders, “have you been tested recently?”

“Yeah, all good,” he quickly answered.

I dramatically plopped my head into the pillow, “fine, but be gentle, it’s been a while.”

He reached for the lube and started pooling it in my hole. I took another hit of poppers, then another. I felt him smearing the lube on his cock and then his cock searching for my hole. He pushed hard.

“Ow, fuck man, geeze,” I nearly bucked him off. “Take it easy.”

“Sorry, just relax, you’re really tight,” he told me. Then started to gently push and my hole started to give in and the head popped in. “mmm,” he moaned.

“Ungh,” I groaned.

“Just breathe, let me in,” he whispered, still slowly pushing in.

Thankfully he was not huge, a solid 6” cut, and average thickness, felt like a baseball bat though.

He bottomed out and held it there. “Fuck you’re so tight, feels so good.”

I didn’t say anything, just tried to relax. Another hit of the poppers and he started to slowly pull out and push back in. It only took a minute for him to get a slow but good rhythm going. He wasn’t trying to pound me, but he was aggressively trying to get as deep as possible.

He lay flat on my back, kissing my neck and nibbling my ears. Holding tight to my hips as he rocked his dick in and out of my hole. It was starting to feel better, his precum was lubing me enough that I could enjoy the sliding across my prostate. I couldn’t help but let out a small moan.

With every thrust into me I felt his grip tighten, his trimmed chest hair gently scratching my back as his dick pleasured my insides. This was way better sex than when we hooked up years ago. I felt my hole letting him in deeper and my ass flexing up to meet his thrusts.

“mmm,” I moaned.

“Yeah, fuck, I’m not going to last long,” he warned.

Picking up the pace, really getting deep, I felt him start to swell inside me, more with each thrust.

“Fuck, I’m about to cum,” he warned.

“mmm,” I moaned, flexing my ass as best I could to increase his pleasure.

“Oh shit,” he nearly yelled, “I’m humming,” he whispered, thrusting deep inside me. His dick spasmed and twitched, the heat from his load radiating inside me as he thrust a few more times, smearing his cum as deep as he could.

“Fuck,” he gasped and suddenly stopped thrusting and his grip loosened. He lay on top of me, trying to catch his breath as his dick went limp inside me.

Our bodies were sticking together, he moaned one last time and then rolled off of me, his dick sliding out as he went.

I pulled my briefs back up and passed out.

I woke up a few hours later to his loud snoring and sunlight streaming in the open widow. I had a wicked hangover, very much regretting letting him fuck me again. I got up and took a long hot shower to kill the hangover and wash away the sex.

I heard a knock on the door, “hey I have to head out,” he yelled through the door.

“Ok,” I yelled back.

“I’ll hit you up, let's hang out soon,” he said.

“Ok,” I yelled back again.

I heard the outside door shut and I finished up my shower. Toweled off and noticed a condom wrapper in the bathroom trash. It hit me, I did use the last condom last weekend. Oh well.

[badjujuboy]

I have to say that I’ve had sex with most of my exes after our “relationship” ended. I learned a long time ago to separate a purely sexual encounter from sex with emotional attachment. The “relationship” ended for a good reason… one of us wasn’t getting what we needed out of it but the sexual connection was still there so we continued to enjoy that aspect. Hell… I’ve even had sex with a pair of exes who were seeing each other.

[PigBoyDallas]

I briefly kind of was in a relationship with a bud in HS but we drifted apart. He said he was bi, but hell, everyone said that in HS. Flash forward a few years and he has a GF and I'm still doing my thing. He hits me up to see how I'm doing, wants to get together and catch up. Winds up with us both fucking each other just like the old days. And its one of those love/hate things with him. The sex is super hot but he's kind of an asshole. And now we fuck regularly and its the whole "my GF can't know BS" just like in HS, yet we're rawdogging each other like crazy. He has no idea I have a vibrant active sex life and he's bored and frustrated as he's not getting a lot of sex. We spiced it up by having a third join us and it was hot as fuck to see the other guy pound and breed my buds ass, but afterwards he was all "that can't happen again". Sexually he is hot as shit, but also boring and vanilla as shit as well. I don't want to be his constant side piece that he hits up when he needs release but I'm all too happy to take his loads and give him mine.

[PozTalkAuthor]

On 8/4/2023 at 2:32 PM, PozTalkAuthor said:

Definitely NOT with my latest ex, I feel disgust just remembering his touch, smell, the warmth of his body or even thinking of his voice. He has psychologically abused of me in many ways. 

But my first ex? The one who made me grow up sexually, the first to load me, the first man I loaded... We're still very confident after 28 years and we see each other regularly. Not yet for sex, but, with my current (monogamous) boyfriend we are discussing it, like a sort of "second generation". I have been my current guy's first and only male partner, I'd find it very sensual to see him have sex with his second, who's been my first! 

And then? What about the man who gave me HIV? Not at all, no bond between us, lost contacts and no interest in recovering them. 

Now, my current bf and I, have our vacation near my very first man's holiday place. Let's see if a thing leads to another, I'd not force anything though, not feeling "the urge" to open our couple, I want to let things go. For now we're all 3 having nice talk and board games. 

With days going, we'll see if the game "the loser strips naked" can be played LOL 

Quoting myself but it needs an update: 

vacation is over (in advance for family trouble) but, no sex with former boyfriend at all! 

We didn't do much; all 3 of us half naked, the guy between me and my bf, commanding us to "use him". We just licked his neck and nipples, some make out, but we both felt discomfort to be treated like toys! 

In the end we gave it up, it's not appropriate to lose a good friendship because of physical pleasure!