My Best Orgasm Ever

I just found this sub and love the true stories shared by people and thought I’d share a few of my own. Back when Craigslist personals existed and was the place to find like minded people seeking to expand their sexual experiences, I was able to connect with many people and have some incredible experiences. One that comes to mind, is the time I had what was probably the most rewarding orgasm of my life, which I’ll share now. I was in my mid 30’s at the time and was a very attractive guy. While perusing CL at work one day, I came across a post made by a local couple who were seeking “single men for good times.” The thing that set them apart from the other ads and caught my eye, was the pic of the female half of the couple they’d included with their post. It was a shot of her in a doggystyle position with her ass high in the air, and what an ass she had! She was curvy with a full, voluptuous ass that immediately made me hard. By that point I’d gained enough experience on the site to know that for any legit posting involving a female, both solo or with her man, there was a horde of twisted male perverts just waiting to drown them with responses. I’d learned of this phenomenon from my conversations with the people I’d occasionally connected with, and they’d revealed to me that the majority of replies they’d receive were either really gross, or really weak , with the only text being “wanna fuck?” accompanied by a stolen cock pic. Because I actually spent the 60 seconds it took to write a personal note to the posters I contacted, and because I was generally attractive; I knew that I would always have a shot of they actually read my reply. The difficulty that I faced was that they may never even get to my reply, because they’d either gotten so turned off by the dozens of lazy or sick responses that they just gave up the idea altogether; or, that they were just too overwhelmed by responses, and mine came in too late and went unseen. On that day, it appeared that they’d posted a few hours earlier and I would probably be too late. Figuring that my chances of actually hooking up with them were minimal, I wrote to them anyways because I was just so taken by the ass in that pic. In my reply to them I gave my stats and all of the usual stuff, but I made a point to tell them of the attentive state which the vision of her ass I’d spied had left my cock in, and told them I was available to party.

To my surprise they responded and appeared to be legit. They invited me to come over ASAP, but were located about 30 minutes from my work. Fortunately, I had a job where I could disappear for hours at a time and my boss would just assume I was in meetings. I headed out and made the drive to their place, getting hornier with each mile at the thought that I would soon be pounding my cock into that that chick’s amazing ass. I pulled up to the house cautiously and surveyed the scene. The house was older and a bit run down, but not enough to cause suspicion. I’d heard enough CL horror stories to know when to be on the lookout for getting jumped. I knocked on the door and a dark haired, taller guy with tan skin answered and invited me in. I didn’t see the chick at first and got suspicious. The girl then walked out of a bedroom, and while she wasn’t a 10, she was still cute. She was a bit short and curvy, so I knew she owned the ass that had me so turned on. Then the guy says “shit…sorry man, we just got done with a threesome.”
Now I’m totally confused as to what the fuck is going on, and if this is a scam or not. I was kind of speechless for a moment and a bit pissed because I’d gotten all worked up and thought I was getting blown off. The guy then says to the chick “he’s the guy that wrote about how gorgeous your ass is.”
She approached me and said “can I see what you have? For next time maybe?”
Fortunately, I didn’t let my frustration at thinking I’d been fucked with get in the way, and I agreed. “Right here?” I asked, as we were still standing in the entryway.
“Come back here” she said, gesturing me to follow her to the bedroom.
I did as instructed and was followed by the guy. We got in the bedroom and she asked me to show her. I still wasn’t sure what to think because it had all been so odd up to this point. I didn’t want to be standing there with my pants around my ankles and sporting a hard cock, only to have three thugs jump out of closet. So, I threw it back to her and said “you first,” to see how she’d respond. She didn’t hesitate for a second, and she stripped her bottom half and laid on the bed, legs spread to show me her pussy. My dick quickly reawakened. The guy said “show that ass he liked so much,” and she obliged, getting on fours and sticking her ass high. It was fucking fantastic! She shook it back and forth and said “you can touch me if you want to.”
Given that her boyfriend was standing right next to me, I didn’t think that jumping straight to finger fucking her would go over well, so I knelt down and placed my hands on each cheek and spread her ass.
She was turned on by this, and she began pressing her ass back into my crotch and dry humping me. I was so hard and so turned on right then, looking down at the luscious ass of this girl I’d met only minutes ago, pressing up against the bulge in my pants. I was so jacked up that I would have been happy to have pulled my dick out right then, and stroked until I painted her cute little asshole with cum.
She turned around then and said “your turn.”
I had no problem with that now, so I stood up, unzipped and pulled my cock out. I have an average to slightly above cock size, but I was so hard in that moment that it looked way larger than usual. She made an “oooh” sound and took me in her hand. God it felt good! She moved her mouth towards it and looked up at me, and said “can I?”
I gave the fastest “Yes” that I’ve ever given in my life, and she started sucking me. I don’t know if it was that she was that good, or because I was so jacked up, or a combination, but it was a sexual ecstasy like I’d never felt before. She sucked on me for about 30 seconds, then suddenly stopped and let go.
I looked at her as if to say “are you fucking kidding me?”
The boyfriend caught on and said “do you want to cum?”
“Uh, yeah,” I replied, and he gave her a nod of approval and she went back to work. It was so good as she worked it faster and harder. I then looked to my left and saw the guy had pulled his massive dick out and was stroking it furiously. I don’t dig dudes and never have, but seeing him getting himself off while watching me get sucked off by his girlfriend, it somehow raised the eroticism of the moment to an incredible level. The pleasure was unreal, and soon I did the gentlemanly thing and told her I was going to cum, and all she said was “it’s okay.” Her boyfriend’s cock had grown to a massive length as he continued to stroke, and I felt the hardest orgasm of my life coming. I threw my head back as I peaked, and I felt blast after blast of cum filling her mouth. As I began to come back to reality, I knew that I had shot an unusually large amount of cum into her mouth, and I almost felt bad. She choked a bit as I was pulling away and then suddenly, the guy was at my side. I stepped back and he jumped right in my place, entering his cock into her mouth. As I zipped up, I saw that he had a handful of her hair and was pumping his cock in her mouth that was still filled with my cum. She was choking a bit and struggling to take it all, but was apparently digging it. Then, he looked back at me and said “hey man, close the door in your way out.” And I did.

That was probably 15 years ago, and I don’t think I’ve had an orgasm that intense since. I did have some great experiences with other people back then, but with the loss of Craigslist personals, it feels like the world went frigid. I later returned to have my way with her and that gorgeous ass, but that’s another story. I don’t know if anyone will dig this story or will find it hot, but if so, that’s awesome. I’ve never written about any of my erotic experiences, so I don’t know how they’ll be perceived. Let me know. Thanks.

Source: reddit.com/r/sexystories/comments/um5py6/my_best_orgasm_ever