I found myself scrolling through the Craigslist Personals section one Friday or Saturday night when that still existed. My FWB was on a date with someone — I think — and I was feeling a little lonely and horny. There was post which advertised a meetup with a 26 year old woman and her boyfriend of undefined age. I had been party to a MFM threeway once before a few years ago and had enjoyed the experience. I was open to the idea of trying again and reached out.
I got a reply back pretty quickly with some attached photos. She was gorgeous; a truly stunning woman. Latina; dark hair, eyes, and skin; petite but busty with some beautiful natural curves. She wanted to see a few photos of me in return and I jumped at the bait and sent her a few face pics. I got some praise and a few nudes in return along with the request for a few of my nudes. I sent them way too eagerly, but that worked out well. She and her man were on the hunt and fast replies were what they wanted.
We had a few quick messages back and forth and I asked about the guy she was with — I don’t really know why, I doubt it would have mattered, I just wanted to make sure he wasn’t gross I guess. She sent back a few photos of them on vacation somewhere exotic and wasn’t disgusting. He was older for sure, and had kindofa televangelist vibe going on. A little smarmy and slightly untrustworthy. At the time I didn’t know what cuckolding was — probably didn’t learn about it or even hear the word for a few years after this event. That said, I was about to enter into a cuckolding situation for the first time and I was going to be the bull.
They told me they were going to be out drinking at the bars for a while, but would be home around midnight. They gave me their address — I knew exactly where it was downtown. I had lived almost across the street from there only a few short months before. I told them I would be there with bells on at exactly midnight and then I began to panic a little. I had met people online dozens of times. I had met couples before with my FWB — though not with the success we had, had in mind. I was an ‘old hat’ at this sort of thing, but something was making me nervous about it. I rationalized that I had always been the ‘man’ of the situation who was generally in charge. In this situation I was going to be the second fiddle to this other guy. Also… meeting randos on the internet can be a little nerve wracking. You never know if things are legit or not.
Well 11:40 rolled around and I was showered, shaved, dressed, and had a few condoms in my pocket. I walked out into the living room, waved hello to my roommates and told them I was going to do something dumb. Then I drove downtown, parked, waited 3 minutes to make sure my timing was right, then headed to the house and knocked on the door.
She opened the door nude; it was the woman from the photos and she was even sexier in person. She smiled wide and invited me inside with a wave of her hand like a magician on stage. As I stepped in she ran her hands over my chest, abs, and bulge before stopping me and kissing me in the doorway. I stepped inside the main room — it was a studio with a kitchen in one corner, a bed in another, and her boyfriend sitting in a chair in the darkened area of the final corner.
I got my bearings as quickly as I could, waved hello to guy in the corner and probably looked like a complete tourist. She got onto her hands and knees in front of me on the bed and smiled. I realized that I would not be required to make any small talk and just walked up to her as I started to take off my shirt. She reached out for my belt and pants and quickly removed them exposing my raging-hard cock. I had been in the apartment for 45 seconds and was only wearing an A-shirt and had my pants around my ankles. I tried to kick off my shoes and shimmy the rest of the way out of my pants as she started to suck my cock and let out these sexy little moans.
I looked back in the corner at the guy and he was just sitting there — watching us. If I had only known that was what he was into I wouldn’t have said anything and just enjoyed his woman while he watched, but I was paranoid. I kept worrying he was going to attack me or sneak up behind me and try to touch me or something else unwanted. “Are you gonna join us?” I asked. He shook his head ‘no’ and waved me off. “Okay.” I said as I tried to remain cool.
She was doing a fantastic job with my cock in her mouth and had started to pinch her nipples in between two fingers while she blew me. I was still unsure about the old dude in the corner. He was giving me weird vibes and my martial artist brain continued to tell me that something was off; I looked back to him again and gestured for him to join in. He waved me off again. “I want to eat your pussy.” I told her suddenly. She leaned back as she continued to stroke my wet cock with her hand and she looked up at me invitingly.
“Okay… I was hoping you would do that.” She lay back on the bed and spread her legs wide.
“God you have a beautiful pussy.” I finally got rid of my remaining clothes and dropped to my knees on the far side of the bed — my ass pointing away from her man and leaving him in my field of vision. She tasted amazing and her pussy was a delight. I slipped two fingers into and worked my magic as I ate her pussy until she came all over my tongue. “Fuck you are hot.” I whispered as I slipped my fingers out of her and rubbed her wetness onto my erection.
“Oh, please fuck me. I want to feel that big cock inside me.” I looked over at her man — for permission? — I dunno. He was rubbing his bulge through his clothes, but was still completely dressed. I had no idea what he was doing or why. If it had been me with my girl I would have been right in the middle of things.
“Do you have a condom?” I asked. Normally, I would have asked in the hope that they said ‘no’ and let me fuck them raw. However, I was getting the impression that I shouldn’t fuck a woman that invited strangers over to her house at midnight raw and wasn’t trying to risk it. She looked at me quizzically and told me I didn’t need one. Now I was 100% sure I needed a condom. “Don’t worry, I have one.” I scrounged around in my pants pocket and plucked out one of my Magnums. I tore it open and started to put it on and she looked really disappointed.
I got onto the bed — again keeping him in view — and slipped myself into her. She let out a sexy howl and began to gyrate her hips on my cock. I looked over at the dude again and asked, “Aren’t you going to join us?” He waved me off again. I didn’t trust him — again, I didn’t know about cuckolding and I feel so bad that I was ruining his experience now that I do know… now that sometimes I have cuckolding fantasies myself. “Come. Join us.” I was very direct and, him being a cuck, he complied immediately.
She was into it and moved toward him taking him into her mouth as soon as he whipped his cock out through the fly of his pants. I started to relax and continued to fuck this beautiful latina woman. Her moans were muffled by the cock in her mouth, but occasionally she would stop sucking him to tell me how good I was doing and how big my cock was. I got a look at what her boyfriend was packing and it wasn’t anything impressive; I was definitely an inch or two longer than him and much thicker. I looked down at her and wondered why she was even with this guy ‘He must be rich’ I rationalized.
I flipped her over onto her hands and knees and took her from behind. Her ass was fantastic and the view of my fat cock pushing into her over and over again was incredible. I asked her man if he wanted a turn and he declined, then he put his cock away and went and sat back on the chair in the far corner of the room. I didn’t care anymore, he was no threat to me, she was amazing, I was just going to put on a show.
I fucked her for 15 or 20 minutes in a few different positions until her phone started to ring. It was almost 1 am and I had worked up quite a sweat. I took the ringing of the phone as a chance to take a break and asked if they needed to get that. She did, apparently, and hopped up to see what was going on. She took the call while I took a breath. I took the condom off and grabbed a drink of water from the kitchen. It was a little weird to be walking around nude in someone else’s house while I was being watched, but it wasn’t the strangest thing that had happened that night so I was un-phased.
“Hey, we have to finish up.” She said when the call was over.
“Oh, sure, okay.” I wasn’t surprised, the call sounded important.
“Do you want to cum on my face?” She was non-chalant about it. “Or in my pussy?”
“Uh,” I was shocked for a moment, “On your face.”
She grinned, looked at her man, then got on her knees in front of me and took my cock back into her mouth. I got hard again and then, for the sake of expediency, began to jerk myself off while I fantasized about blowing my load onto her pretty lips. She touched her pussy with one hand, pinched one of her nipples with the other, and kept her mouth open and tongue out for me as I pumped my hand over my cock as fast as I could.
Finally, I was ready. “I’m going to fucking cum.” I groaned before unleashing three or four thick ropes of cum onto her tongue and face. She sucked the head of my cock as my spasms slowed down and I put my hand on the back of her head and forced her down my shaft as deep as she could go. My legs shook and I let out a whimper of happiness. The last thing I did was to shake out any remaining cum onto her tits with a few flicks of my wrist. It was hot to see the last remnants of cum glisten on her like glitter.
“Have a great night.” She said from her knees, “I hope you come back again soon.”
I took the hint and got dressed rapid fire. I said goodbye to them and walked toward the door. He still sat there, she was still on her knees. I left with them in the same position not realizing that something even kinkier was probably about to transpire in my absence.
She emailed me a few hours later and asked me to come back again. I knew I needed to run it all by my FWB, Penny, before I responded. Unfortunately, that led to a weird argument with Penny who demanded to be included next time. The couple was not interested — for whatever insane reason — in having Penny join us. So I never saw them again as I tried to keep the sex life going strong with Penny. I was disappointed though, and was starting to get frustrated that Penny wasn’t supportive of my having fun on the side without her. It ended up leading to me taking a break from Penny for a few months as I seriously dated someone else.
A year and a half later I moved back to the city and lived about a block away from that apartment. I would often walk by and try to peek in the window to see if anyone was at home. A few nights, when I was drunk, I considered knocking on the door to see if she was still there but I also didn’t want to be a complete creep. I always figured I’d recognize her if I saw her out and about and strike up a conversation that way. Oh well, such is life.
Source: reddit.com/r/gonewildstories/comments/n1rw99/i_met_a_couple_on_craigslist_and_fucked_her_while