This took place back when I was 19 (37M now), and Craigslist was all the rage for casual encounters. However, I had no clue that the casual encounters section of the site even existed then. I was working at a well known hotel in San Diego at the time in the in-room dining department (answered phones, took down food orders). One of my friends shared with me a link one day to a post on Craigslist for a gang bang that was being planned at the hotel I worked at. He thought it was hilarious, given how nice of a hotel it is, and given that the surrounding community leans quite conservative. I was surprised to say the least, but then when I saw there was an entire section of Craigslist dedicated to casual encounters and other debauchery, I was completely shocked. I had no clue this part of Craigslist existed. I was always under the assumption it was the website you went to when you were looking to buy a used car, furniture, etc. Because of the posting my friend shared, a door was opened, and my horny-ass couldn't wait to step through it.

First and foremost, no I did not reply to the gang bang post. The hotel I worked at was very strict about what employees did on the hotel grounds when they were off the clock (we couldn't even visit the bar for a drink), so as exciting as the post was, I declined to pursue it. My friend wasn't encouraging me to or anything, he just thought it was hilarious that such an event was taking place at the hotel. But from then on, I was exploring all the w4m listings.

A little about my sex life before Craigslist: I had been with 5 different girls in high school, all fun and nothing kinky. I wasn't a player or a popular guy to say the least, but I was always told I was handsome and could make people laugh, and that definitely helped with getting laid. None of them were relationships, just one time things (with one or two turning into FWBs).

As soon as I first joined the internet, I was a full fledged porn addict. It was free, and slowly I began to discover what turned me on. MILFs, threesomes, lesbians, etc. So with that in mind, one day on Craigslist I finally found the courage to post on the m4w section looking for a MILF to fulfill my older woman fantasy. I didn't want to waste my time replying to hundreds of w4m ads daily because I assumed women who were posting were getting thousands of replies a day. I figured to approach it like fishing: place my ad and see if I got any bites. After two weeks of primarily spam replies (and a few guys of course), an actual woman replied to my ad. "Would it be okay if my husband joined?" The mere idea of my MILF fantasy suddenly evolving and adding my threesome fantasy got me excited. I replied back that while I had never been with an older woman, or a couple before, I was open minded enough to give it a try. I just wasn't interested in doing anything with her husband. She said that was fine, and we began to exchange emails and pictures back and forth.

Let's call them Cindy and Matt. They were a white couple in their 50s from Nevada, and Matt was retired military. They sent photos and I could tell Cindy was fit and had handsome features, and Matt was shirtless on the beach showing that he was also in shape. One thing I did note was Matt's picture looked a little old and probably wasn't recent like Cindy's were. They were visiting San Diego for a few days and wanted to have some fun while in town. They were swingers, and enjoyed playing with younger guys. So we made a plan to meet up that weekend in my neck of the woods, talk in public to see if we all clicked, then if so, I would head back to the place they were staying at. I was incredibly anxious in the days leading up to our meeting, but we kept in touch via email to make sure each party was still good to meet up.

Saturday afternoon I was waiting by the pier, our agreed upon location, anxiously scanning the crowd. I had three condoms in my pocket that I nervously cradled with one hand, and kept checking my flip phone with the other for any text updates. At one point some family friends of my parents saw me and came over to chat for a few minutes, and I was terrified that Cindy and Matt would pick that moment to come over and introduce themselves. Thankfully I managed to wish my family friends well and they were off to enjoy the rest of their day. But from then on it felt like everyone in the world knew what I was doing there, who I was waiting for, and what depraved shenanigans I was about to get into. A short time later a man and a woman cautiously walked over to me and asked, "Zeke?"

"Cindy and Matt?" We had contact. Cindy looked like her pictures still, very attractive in her black tank top and blue running shorts, and a little over 5'7. Matt on the other hand, was in fact using older photos of himself because he was not that in shape. 5'9, stocky frame, balding, with a big mustache. He was probably early 60s and not still in his 50s. I was just happy that Cindy was attractive (and a total MILF in my book), so we exchanged pleasantries before walking along the beach to get to know each other a bit more.

They were staying on the Naval Base in Point Loma, and because Matt was retired military they were able to stay in Navy housing for a discount when they traveled around the country. They had been swingers for decades together, and always enjoyed playing with younger guys because that was Cindy's fantasy. They asked me a bit about myself and history with women, what I enjoyed, and basically just wanted to make sure I wasn't some kind of psycho. I told them I always had fantasized about being with an older woman, how I loved to eat pussy, and that I was open to whatever they had in mind as long as I felt comfortable. They assured me they would be gentle and help guide me since this would be my first encounter with a couple. They excused themselves to talk it over for a few seconds, then came back to me. "Ready to head back to our place?"

Matt was driving the rental car while Cindy and I sat next to each other in the back seat. We slowly started to explore each others bodies over the clothes, and I was starting to get aroused. I was still feeling anxious, as if this was my first time having sex again. It was a giddy kind of excitement, and Cindy could feel through my pants how excited I was getting as I felt-up her breasts. They were a medium size, and natural. She was giving soft moans and giggling, and Matt was frantically looking at us in the rearview mirror, not wanting to miss any of the action. I was a little nervous when he was driving over the bridge, because I didn't want him to accidentally crash and kill us all. "Oh he is a big boy" she cooed to Matt as she felt my throbbing cock in my pants. I realized the running shorts she chose were strategic, and I was easily able to slip my hand up her shorts and feel her warm wet pussy and little muff. I started to finger her with one, then two fingers, and she tried sitting diagonal to give me more access. The more she moaned, the more excited Matt got. He tried reaching back with one arm to caress her leg, wanting to be a part of the foreplay. He asked if she was enjoying herself, if she wanted my hot cock inside her, just dirty talking with her back and forth. I really wanted to eat her out in the back seat, but we were approaching the Naval Base and he gave us a heads up. I removed my fingers and put them in my mouth, enjoying her taste. She loved that. We all got our IDs out, and I was really nervous that the guard was going to flag me as a civilian, and he too was going to realize what I was doing with this couple that was old enough to be my parents. But alas, he handed back the IDs and lazily waved us through. Didn't he think it was weird that Cindy and I were in the back seat and Matt was our chauffeur in front?

Matt parked the car and I followed him and Cindy to these ugly looking dorm style apartments. We walked down what felt like an endless hallway, my heart beating faster and faster with every step. Finally we got to their room, and went inside. It was a simple hotel style room, with a big bed in the center, bathroom off to the side, a small desk, and chair. A TV was on a dresser opposite of the bed, and their luggage was on luggage stands next to the dresser. Cindy told Matt and I to get comfortable, as she was going to slip into something a bit more sexy. So Matt started to undress, having done this hundreds of times before, and I slowly stripped down to my boxers. He motioned to me to sit on one side of the bed, and he would sit on the other. So there we were, sitting next to each other on the bed. Him fully nude and stroking his flaccid dick, and me in my periwinkle blue boxers with a half-hard chubby. I didn't think he was going to do anything like touch me or offer to get me hard, but it was just such a weird experience waiting for Cindy next to her naked husband. Like, what would any of my friends or family think if they ever found out??

Finally Cindy walked out of the bathroom in nothing but sexy red lingerie and gave a little twirl for us. I was suddenly excited again, and it started to show in my loose boxers. Matt was excited as well, and started complimenting her outfit. I did too, and she walked over to my side of the bed so I could get a better look. She had a small tattoo of a cartoon bomb above her pelvis, and Matt remarked she got that tattoo back in her wild party days. I caressed her body as she stood next to me, and she caressed my leg and crotch, getting a better feel of my dick since the pants we removed. "Let's get a proper look, shall we?" she asked, and I immediately took off my boxers to reveal my almost 8-inch uncut cock. She gripped it in all its glory and slowly started to stroke me to see the head. She liked what she saw. "Goddamn he's big!" Matt commented, with Cindy agreeing. "Scoot over boys, let me get comfortable," she commanded. We made space in the middle of the bed and she crawled into it on her knees, settling between us. She then took my dick in her left hand, and Matt's in her right, and started comparing the two. "See honey, his head is so smooth compared to yours." It was true. Matt's dick was circumcised, average length, and looked dried and a tad worn out. Mine however, was smooth, crimson pink, and young. Cindy then leaned forward and sucked the head of my cock for a few seconds, moaning slightly. "Yup, nice and smooth." She sucked me some more, then shifted to Matt and sucked him. She went back and forth, sucking and stroking us both, and I was getting excited that this was actually happening. I didn't even like getting my dick sucked (that's a story for another time), but seeing this MILF suck me off while stroking her husband simultaneously was burning an image in my mind that would never leave me. A permanent addition to the spank bank.

After pleasing us for several minutes, I then offered to reciprocate the favor. She was most welcoming of my offer, and laid down in my spot on the bed while still stroking Matt. I went to the end of the bed and slowly removed her red lingerie panties and Matt took off her top. Her toned, tan MILF body was incredible, and she could have easily been in her 40s. And the little muff of hair she has was also such a turn on, showing she was in fact an older woman. I kissed her legs from the ankles to where they met, and slowly started fingering her again. She rocked her hips back and forth, loving it. I then saw Matt shift to his knees and Cindy started to blow him some more. I then tasted her as I fingered, sucking her clit and getting a little of her hair in my mouth as well. I was loving it, for eating a girl out was always my favorite part of foreplay. I eventually removed my fingers and just kept going with my mouth and tongue, lapping up all her juices (and she was extremely wet by that point). I was in absolute heaven, and continued to stroke my hard cock with my free hand. Eventually Matt proposed we switch, and we did. Cindy enthusiastically started sucking me again, and Matt gave her pussy a quick lick before repositioning himself and shoving his dick inside her. I was a little disappointed when I saw he started to fuck her, because I was hoping to eat her out some more. But now that his dick was inside her, I didn't necessarily want to taste him. Matt's thrusts caused Cindy to moan, and the vibrations of her moaning felt good on my dick. The bed began to creak a bit, and once again paranoia took over for a brief second: "The neighbors totally know what we're doing. Someone is going to call and complain and I'm going to get escorted off for not being allowed to be here." But no one did call, and Matt told me we should switch and I can enjoy fucking his wife's pussy.

So I went to my pile of clothes on the floor and retrieved the condoms from my pants pocket. I slid a Magnum on, and approached Cindy on the bed. She was on her back, Matt's dick once again in her mouth, and she happily parted her legs for me. I positioned myself, added a little lube to my dick, and entered. Cindy was so tight and warm that I let out a moan of pleasure. I was doing it: I was fucking a MILF. I slowly thrusted into her and she gasped from my size. "Holy shit, he feels so good," she told Matt. "Yeah baby, take that fucking cock," he commanded. I slowly got a rhythm going, and Matt helped pull one of her legs back so I could get deeper. She moaned, she gave muffled little yelps of pleasure (Matt's dick was silencing her), and I excitedly continued to plow away. I made sure not to be a jack-hammer, but I was a little intense. She loved it, and fucked me back with her hips to try and take all of me in. I was inches away from her face as I thrusted, getting a front row view of her sucking off Matt. I was living in my own personal porn video, and they made me feel like a god.

We eventually switched positions, and Cindy got on all fours as Matt fucked her and she took off my condom and sucked me. My first spit roast. I held her head and helped guide her back and forth, feeling a little sorry she had to taste my latexed dick. A couple of minutes later, and Matt huffed and puffed and finally came. We had been playing maybe 30 minutes at that point (15 min foreplay, 15 minutes fucking), and I was a little surprised he had ended quickly. I was a little relieved that I wouldn't possibly be the first one to cum, so after he went to the bathroom to clean his dick, Cindy suggested I get another condom and lay down on the bed. I did so immediately, and she positioned herself on top, grabbing my dick and guided it inside of her as she sat down on me. Again, she felt fucking fantastic, and I quickly matched her rhythm. She rode me nice and steady, while my hands caressed up and down her body and breasts, giving her ass a nice grab as well. She grabbed the headboard for support and continued to fuck me. Matt came back out of the bathroom and enjoyed the show, moving next to us and also caressing Cindy's body.

After 10 minutes of fucking me, I realized she was ready for me to come. I suggested doggystyle (my favorite) since that would make me come probably immediately, and she once again assumed the position while I now fucked her from behind and she continued to play with Matt's dick in her mouth. After another 10 minutes, I realized I was too nervous to come and probably wouldn't be able to. I mentioned that we could stop if they wanted, that nerves weren't allowing me to come, and they both understood. I could tell Cindy was a little disappointed, but mentioned it wasn't the first time a younger guy they had been with couldn't come. "It's better than you not being able to get hard. That's usually the main problem with out meet-ups," Matt remarked. So with out fun officially over, Cindy went to the bathroom to clean-up, and Matt and I got dressed. We sat on the bed and had a little small talk, and he told me how jealous he was of me because Craiglist wasn't a thing when he was my age. "I didn't even lose my virginity until after college! I would have killed for the internet back then!" he complained.

After Cindy was dressed we all got back in the car and Matt drove us off the Naval Base, with Cindy this time in the front seat and me in the back by myself. They dropped me off where we first met, and Cindy gave me a big hug and kiss on the cheek. "Thank you for that, we had a lot of fun." she remarked. Matt shook my hand as if I was doing him a favor fucking his wife, and we parted ways. As soon as I got home I masturbated like three times in a row, reliving the experience I just had that was permanently burned into my brain. While I was disappointed I couldn't come in the moment, I still think back fondly to my first encounter with Cindy and Matt, and I'm forever grateful they took a chance on me and gave me a great first experience.

We stayed in touch over email, and little did I realize that two years later I would have the opportunity to meet with them again.