So far thanks to Craigslist I was two-for-two when it came to hooking up with couples. Matt and Cindy helped introduce me to the lifestyle, and Andy and Betsy showed me what an ongoing sensual experience was like. After they decided to take a break and recommended I get back out there looking for new couples to play with, I confidently resumed posting and replying to ads. What still helped me stand out from the rest of the single guys at the time was how young I was (20), and now having experience being with two different couples and eager to please.

Enter Pablo and Roxy, both in their mid-40s. Pablo initiated the conversation by sending me a sexy photo of his wife bent over the bathroom sink, nude, and seductively looking over her shoulder. She was short and stout, tanned, a warm smile, and had blonde frizzy hair. Pablo was taller, also tan, had thinning black hair, and kind of had crazy eyes going on. I should have taken that as a red flag. They both were originally from Brazil, and now lived in Santee. They had been swinging for years, and loved playing with single guys. Because I was 20, that caught Roxy's eye, and she insisted Pablo reach out and see if I was interested.

We exchanged emails for a week, with Pablo sending very graphic photos of what he wanted to see me do to his wife. He wanted me fucking her every which way, spitroasting, DP, DVP, and then ending it with a giant creampie inside her. I definitely had the impression that he saw his wife as his own personal porn star, and wanted to have his own private show while also joining. I had never done a DVP or DP before, but told him I would be open to it, realizing our swords would be crossing a few times in the acts. "It's such an amazing feeling, we do it all the time. You won't regret it," he assured me. We made plans for the following weekend, and they would meet me at Horton Plaza so we could exchange a few brief words, make sure everyone was who they said they were, and then they would drive me back to their place.

Saturday came and we met on the first floor by the escalators. I had no condoms to fiddle with in my pocket this time, so I just scanned the crowds anxiously looking for a couple that hopefully resembled their photos. Eventually a short woman of 5'3 and a tall man of 6'2 made a beeline to me. "Zeke?" "Pablo? Roxy?" We had contact. We shook hands, and I noticed that Pablo's big blue crazy eyes were even more intense in person, while Roxy's sweet smile helped put me at ease. They had Portuguese accents, which made it somehow more erotic to me. We didn't stay long walking around Horton, and quickly made our way to their car in the parking lot. I remember it felt like a long drive to their place, and to show how hip they were, Pablo put in a Cage The Elephant CD while we discussed our experiences in detail. They had been playing ever since they were first married in Brazil, and missed the scene terribly. When they eventually moved to the United States, they quickly discovered Craigslist and SwingLifeStyle were their best options to meet new people. "What's SwingLifeStyle?" I asked. "It's like Myspace, but for swingers to find each other and hook-up. If you join, let us know and we'll verify you."

We finally arrived at their apartment complex and quickly made our way inside. It was scorching in Santee, and there were almost no trees to provide cover at their complex. We made our way up some stairs, they opened the door, and to everyone's surprise their roommate was just leaving. "Oh, hey Ted! We thought you were already gone!" Ted looked at me, and immediately knew what was happening. I'm sure he was 100% aware of Pablo and Roxy's activities, and it probably took him aback how young their latest toy was. It looked like he was trying to send me a message telepathically saying simply, "Run, you have no idea what you're getting into," and I should have taken his advice. Red flag number two. "I was just leaving," he quickly mumbled and made his way down the stairs in a hurry. Once we were inside they apologized about the awkwardness with the roommate. "We thought he'd be gone by the time we got back. Oh well!" They laughed, and I laughed nervously.

After we removed our shoes we made our way to the bedroom. They had the master bedroom and Ted seemed to have the spare. Their bed was a king size, and had a cushioned chair at the end of the bed facing it. Pablo had mentioned in our emails that one of the things he wanted to watch was me sitting in a chair while his wife rode me. They had everything prepped and ready to go it seemed. To make me feel more comfortable, Roxy started removing her clothes and doing a sexy little striptease for us. While short and a little plus sized, Roxy was still a sexy little cougar, with lovely breasts and a nice big ass. She had a little hair patch still, which turned me on even more. She came over and went up on her tippy toes to kiss me, and I bent down to enjoy it. She then helped me remove my t-shirt, unbutton my pants, and remove my boxers. Out of the corner of my eye I saw Pablo quickly get undressed as well, making sure he was ready for anything. He was already hard, and looked to be around 7-inches, still a little smaller than me. He instructed Roxy to continue the kissing on the bed, and Roxy obeyed by playfully pushing me backwards so I would fall on the bed. She crawled on top of me, grinding on my half-erect dick while continuing to make out with me passionately. I grabbed the back of her frizzy hair at the base of her skull and held her steady, our lips and tongues exploring each other. With one hand she started stroking me, helping me get fully hard, which didn't take long. Pablo had positioned himself at the end of the bed, a crouched seated position, and was stroking himself hard and fast. "Let's take this under the covers," Roxy suggested, teasing Pablo by preventing him from seeing what was going to happen next.

Under the covers, Roxy pulled the sheets completely over our heads and giggled as if we were children. The kissing continued as we lay side by side facing each other. She was still stroking my dick, while making comments so Pablo could hear. "Mmm, he's so big! What a sexy young cock!" I had started to finger her, rubbing her clit and poking a few fingers in. She was getting wet, and after stroking and prodding each other for a few minutes, I asked in a whisper if I could go down on her. She smiled and said yes. I made my way down to her pussy under the covers, and started licking her clit and tonguing her passionately. She moaned and moaned, squirming as she held my head tightly between her legs. I managed to add a few fingers into the mix, and soon she was gyrating and humping wildly. I could hear Pablo still stroking frantically, which surprised me how loud he was doing it. It was as if he discovered the act for the first time. After a short time enjoying Roxy's pussy with my mouth, I wanted to enjoy her pussy with my dick.

Still under the covers, I crawled back up to her and positioned myself on top of her tiny body. She reached for my dick, and guided me to the entrance of her pussy. I slowly entered, and she gave a big moan of approval. She was tight, warm, and heavenly. After adjusting for a few seconds, I slowly began to thrust into her until a rhythm was established. "Is he in you? Is he fucking you?" Pablo inquired. "Oh yes, he's fucking me and it feels soo good!" "Let me see!" "Not yet!" she teased. She clawed at my back, encouraging me to fuck her harder and deeper and I did. We then shifted to our sides again, still connected and face to face. She started passionately kissing me again as I continued to fuck her. Suddenly, the covers were yanked off and Pablo stood at the side of the bed, erect and victorious. "That's what I wanted to see!" he said, and started to stroke himself again. Roxy laughed as if we had just been caught in the act, and she soon shifted to her other side to face Pablo at the side of the bed and offer me her backside. I entered from behind, and resumed fucking her as she now started sucking Pablo's dick. He held her head steady and thrusted his dick down her throat, forcing her to choke several times. I reached over and grabbed her breasts with one hand and her hips with the other. We had a nice little spitroast going, and I was really enjoying myself.

"Let's have you ride him," Pablo suggested and Roxy obeyed. I laid on my back and Roxy squatted over me. I entered her again, and she started to ride me like a secret cowgirl. I all felt amazing and I felt like I was getting deeper and deeper inside her with every thrust. And then I felt Pablo's tongue licking my balls and Roxy's ass. "Woah!" I yelled, and stopped fucking to see what was going on behind Roxy. "What's wrong?" asked Roxy, and I explained I felt a tongue on my balls. "Sorry, I was aiming for her asshole!" Pablo said. "It's okay, it just felt like you really got a good taste of me there. Like I mentioned in our emails, I'm not into that kind of stuff." I said. Roxy tried rectifying the situation by telling Pablo to stand on the bed so she could continue to suck him while riding me. He did, and from my perspective I saw this giant being sucked above me, and I tried focusing my vision on Roxy's bouncing tits instead. Soon after we changed positions again, this time Pablo laid back while Roxy blew him while on all fours, and I continued fucking her doggystyle. After Pablo got his fill of being sucked on, he suggested I sit on the chair and have Roxy ride me like we talked about. I agreed and went to go sit down on the cushioned chair at the end of the bed.

It was comfortable on my bare ass, and soon Roxy straddled me once again on my hard cock. There were no armrests to support her knees, so she clung to me, balancing on my dick for support. The angle and me supporting her weight made it hotter, and she continued kissing me while I fucked her. We had started working up a sweat at this point, and I felt like her personal fuck machine. As we were in the groove, once again I felt Pablo on my balls behind Roxy. This time, he was sucking on them. "Dude, what the fuck?!" I yelled, carefully helping Roxy off me. "Sorry, sorry, I got caught up in the moment," Pablo apologized as he got up from his knees. "I told you I wasn't into that, and you just did it again. I don't feel comfortable anymore, I want you to take me back to Downtown." Roxy again tried to settle tensions by taking Pablo into their bathroom to have a talk with him. I could still overhear parts of the conversation, they switched from English to Portuguese. Roxy was scolding him and Pablo sounded timid as if he just had his hand caught in the cookie jar. A few minutes later they both came out, both apologizing profusely. They offered to keep things going, just a straight MFM threesome, but I told them I was uncomfortable by the deception and wanted to go home. Roxy asked if they could finish their playing first, and I could just watch and stroke and finish myself, and I agreed just so we could end this bad experience and go home.

I sat back down in the seat and started lightly playing with myself to get hard again (I went soft after Pablo's last assault). Roxy laid on her side, facing me, and Pablo entered her from behind and started fucking her like a jack hammer. She moaned, trying to make it sexy, but then Pablo started reaching around to her breasts and started grabbing them hard, followed by slapping the shit out of them. I was horrified watching them fuck, and stopped touching myself in case they saw this as encouragment. I started getting dressed, and seconds later Pablo finished, grunting and sounding like a disgusting creature. He was sweating profusely, and slapped Roxy hard on the ass for a job well done. We all got dressed and went out to the car for the long awkward ride back to Downtown.

Pablo acted like nothing was wrong, we were all great friends, and fondly described his favorite parts of watching me fuck Roxy. Roxy smiled and chatted with us both while the same Cage The Elephant CD played from the beginning once more. They parked at the Horton Plaza parking structure again, planning on getting some dinner someplace nearby. Pablo shook my hand again, apologized once more, and mentioned maybe we could try it again in the future. Roxy gave me a warm hug on her tiptoes, whispered how much fun she had, and also mentioned we should stay in touch. I thanked them for the ride back, and quickly got the hell out of there.

So that was my first bad experience with a couple. Despite the red flags, I was still young and thinking with my dick and it got me sexually assaulted. I'm serious about that, too. Pablo took advantage of the situation, and despite us talking about ground rules when we were emailing back and forth, still attempted to force giving me pleasure when I didn't want it. It seemed this wasn't new to Roxy, and he had done this before with other guys. While I did have a very fun time with her up until that point, she was still an accomplice in a way. Not letting her off the hook for what Pablo was doing / planned on doing. My advice for any guys reading this is to watch for red flags, and if you're not comfortable, remove yourself from the situation. Believe it or not, this experience was one that made me seriously consider getting my driver's license so I wouldn't be caught in a similar situation again.

It took me a few weeks to decompress from the encounter, but soon after I was back on Craigslist, and now also setting up an account on this SLS website I had heard about.