Despite the last encounter starting strong and ending terribly, I took a break from Craigslist for a while. I was dating a coworker for a few months before she ended up cheating on me, which is a shame because she was open to playing with other couples. She had just come out of a high school sweetheart relationship that had lasted 6-years, and wanted to explore the many other dicks she had missed while monogamous. I was one of her hook-ups, and the hook-up evolved into a relationship, but turns out she was still exploring other dicks on the side without my knowledge. After we broke up, I decided I wanted to maybe try Craigslist again and swear off dating for a while.

After searching again on mw4m over the course of a few weeks, a post with a very familiar face caught my eye. While the face was blurred, I could definitely tell it was Betsy from the red hair and pale petite body. But the guy railing her in the pic wasn't Andy! The post itself was written by the guy railing Betsy in the picture, mentioning he was looking for several guys to help bang this redhead milf he was hooking up with. I immediately replied to the post, mentioning I knew exactly who Betsy was and I was totally down to help please her in a group situation. The guy, Gary, eventually responded and told me to slow down, there was a vetting process, he was in charge of assembling the guys. Feeling a little annoyed I was being brushed-off, I emailed Andy on the side and told him I saw and replied to the post, was thrilled they were swinging again, and told them I was down to join in on the fun especially since I just came out of a relationship where I was cheated on. Andy replied back stoked that I was down, apologized for Gary, and told me I was definitely on the VIP list for whenever they were going to host it. After I was cheated on, I had a full panel STD test to make sure my ex didn't give me anything, and wound up being clean. Andy was happy to hear it, because Betsy hates condoms.

A few weeks passed and Gary emails me the date of the meet-up. Andy and Betsy are hosting at their apartment, and it's going to be 5 guys total (me, Gary, Andy, and two other guys). Andy even starts texting me photos of Betsy in the nude throughout the week to get me excited (on a flip phone, with like a 3-inch screen and pixely. I still managed to jerk-off to it). The weekend arrives and Andy once again picks me up at the metro station and drives me back to the apartment. Betsy is walking around nude in nothing but her glasses and knee-high socks (which is what started my kink that night), and is a little tipy from the liquid courage she consumed before everyone arrived. We hug, I'm starting to get excited, and then there's a knock at the door. 

Gary has arrived, and it's a bit surprising seeing him in person. He's in his early 50s, looks a bit haggard, losing hair, overly tan, and has a bit of a beer gut going on. Compared to me (20, in shape) and Andy (buff, in shape), he looks like shit. Why did Andy and Betsy even hook up with him in the first place?! It seems like this is all that he has going on in his life, otherwise he would be found at some dive bar getting wasted and going home with whoever would take him at last call. I was surprised, but thought maybe he fucks well. Immediately he tells us the bad news: on his way over, the other two guys he had lined-up flaked within 15-minutes of each other. Andy's annoyed, and Betsy seems a little let down. I too was hoping for a larger group, but hey! More playtime for me!

Betsy suggests we all get undressed, mentioning, "It's not like I've already fucked everyone here or anything!" and we all laugh. Sure enough, Gary looks even worse fully naked. He's got a pierced nipple, an ugly green tattoo of a dragon on his shoulder, and his tan is patchy all over his body. Betsy puts a towel down on the floor and gets on her knees as the three of us stand around her with me front and center. We're all stroking ourselves to get nice and hard, and I'm still the biggest one of the group at nearly 8-inches. Andy and Gary are the same size of 6-inches. Betsy soon takes over stroking Andy and Gary while she starts sucking me since I'm at eye-level. I miss her mouth, and it's a wonderful reunion. She sucks on me for a few minutes, then starts going around the circle, always stroking two and sucking on one. Andy brings the camera out and starts snapping pictures of the blowbang, with the flash lighting up the room every few minutes. Betsy at one point asks for him to take a break with the camera since she's starting to become blind from all the flashing. The mood becomes a lot more fun and relaxed, and Betsy is slapping our dicks on her face in a playful manner, and even sucking playfully on our balls.

A little while later and she demands to get fucked. I'm fully erect and ready to penetrate, but when I look over at Gary he's still stroking his half-hard dick. He was hard during the blowing portion of the evening, but now it appears he's having trouble staying hard. He suggests Betsy keep blowing him on the bed while someone fucks her from behind. I volunteer to fuck her from behind, and Andy gleefully continues stroking with one hand and taking photos with the other. Betsy gets on all fours on the bed and continues to suck Gary. I kiss her pussy from behind, lightly fingering her to get her prepared. I wish I could eat her out, but she demanded to get fucked so what the woman wants the woman gets! I position myself behind her, apply some of the scented lube, and enter. She groans from my size, but is muffled on Gary's dick. I start slow, refamiliarizing myself with her beautiful tight pussy, and then I started to pick up the pace while tightly gripping her hips. She's loving it, and pushing back onto my dick with every thrust. She takes Gary's dick out of her mouth to get some air, while moaning and telling me how great I feel. Andy too is shouting words of encouragement to her, getting every angle with the camera.

Gary is still not getting hard, and is now embarrassed by it. He apologies and moves off the bed and sits down on the couch next to it and keeps stroking, mentioning he'll watch for a little bit to try to regain composure. I'm a little frustrated on Andy and Betsy's behalf, because what was supposed to be a big group gangbang has now turned into a threesome. Andy tags in for Gary, and we place Betsy on the end of the bed on her back, and I fuck her missionairy while holding her legs up and open. Andy bends over her head to allow her to suck him. Her petite tits are getting a work out as I've fucking her with passion, and she attempts to hold on to Andy to stay put, groaning on his cock. "Dude, her moaning on my cock feels so good!" he tells me. "Fuck her harder, dude!" And so I do. It gets to a point where Andy gets up again to continue snapping pictures, and Betsy is holding onto dear life to the bed. Watching Gary stroke his sad penis on the couch makes me feel like a young stallion to his old mare, and for whatever reason causes me to show-off. I take Betsy's hips and lift them up as I step-up onto the bed and remain standing. I'm holding her body vertically, and in a slightly crouched formation I start fucking her in a piledriver position. "DUDE! YES! HOLY FUCK, DUDE!" Andy yells and starts taking pictures to prove it happened. Betsy is also shocked by the change-up, and starts gasping in shock and surprise. I can only last in the position for a few minutes before I start getting a little uncomfortable, and I place her back down and continue to fuck her in missionairy again. Her hair is a mess, her glasses crooked, and I'm feeling like a god.

Gary saunters back up to the bed next to her, a little harder, and offers her his dick to suck on once again. Betsy's full attention is on me, so she only strokes him before committing, to see if he's actually going to stay hard before she wastes anymore time on him. Andy joins on the other side and Betsy continues stroking them both while getting fucked by me. At one point she tells us she wants to change positions, and tells Gary and I to sit on the couch and she'll ride us both. "My turn, I want to ride some dicks." Gary and I sit next to each other on the couch, and Gary is still stroking, clearly trying to remain hard. Betsy notices, and decides to start with me. She wraps her arms around my neck, places her legs on either side of me, and starts to grind her wet pussy on my shaft, teasing me. She eventually sits on me without using her hands to guide me, and starts thrusting her hips back and forth to get me deep inside her. She moans in my face, and I remember her having cock breath. I quickly nibbled on her neck to avoid any kissing. She rode me up and down, and I grabbed onto her tight ass to increase each thrust. Gary kept stroking with one hand and fondled her breasts with the other, wanting a piece of the action. She looked over and saw he was still soft, and took that as a green light to keep her attention on me. She eventually got up, turned around, and sat back down in a standing crouch. Andy appeared in front of her to take more pictures before positioning her head to suck his dick. She sucked him at an awkward angle, making it a standing spitroast almost. After she was done sucking him, I pulled her back to me and hugged her body, grabbing her tits and nibbling on her neck while I thrusted deep inside of her. Andy went in close to get a picture of her stuffed pussy. All the riding got us both nice and sweaty, so she soon dismounted and flopped back on the bed for a quick breather.

"Can I eat you out while you catch your breath?" I asked. Since I had been the only one penetrating her for the past hour, I had no problem tasting my own dick in her. She agreed and opened her legs for me. Her pussy was warm and smelled a bit like me, but the taste was definitely still all her. I got to eat her out after all! Andy resumed taking pictures, and slowly saddled up to her and she continued to suck him. I added some fingers into the mix, and eventually got in sync with her thrusts. I could feel her tightening and knew she was going to cum soon. I kept the licking and fingering steady, and she soon was gripping my hair with her hands and announcing she was going to cum soon. She got tighter and tighter, then suddenly quivered all over and came screaming. It was so hot, and I was instantly hard again as I didn't slow down with the fingering, letting her ride it out. 

After that she was exhausted, and asked if we were going to cum soon. Andy once again directed us to aim for the face, and had Gary and I kneel on either side of her to pose stroking over her face pre-cuming. Gary looked miserable, and I flashed a victorious smile. Betsy played with her pussy during the staging. After Andy got what he needed, he told us to let loose when we could. It took me a few minutes, and I fondled Betsy's breasts as I stroked. Soon I was ready and let Andy know. Betsy closed her eyes, opened her mouth, and a majority of my cum splashed in her mouth and cheek. She then lifted her head to suck the rest out of me unexpectedly, and she completely drained me. It was like pop rocks went off in my brain, it felt so good. Andy handed her a towel to wipe off the rest, and asked her to finish him off next. Gary had started getting dressed at this point, and I grabbed a cup of water and sat down to watch Betsy and Andy on the bed. Andy laid down on the bed and Betsy bobbed her head over him, sucking him the way he enjoyed. I picked-up Andy's camera and started taking pictures for him. He high-fived me and kept on hand on the back of her head to help guide. A few minutes later and he too came down her throat, and she cleaned him up like a pro.

Betsy got into a t-shirt while getting hydrated in the kitchen. Her cute little ass and pussy were still out on display, as were the knee-high socks. I wanted a round two with her, she was so fucking sexy. Andy thanked us both for fucking her, and mentioned to me the reason they wanted this gangbang in the first place was because they were moving to the East Coast soon, and wanted to go out with a bang. I was devastated to hear it. After feeling depressed about my ex, this night with Andy and Betsy once again brought my spirits up and made me believe in the power of craigslist once again.

Andy asked Gary if he could give me a ride back to the metro station, and Gary reluctantly agreed (probably because he felt like he let everyone down). He drove a jeep, and halfway to the metro station it broke down. I had to get out and help him push it to the side of the road. I was already exhausted from the workout with Betsy, so pushing a car after sapped my last remaining strength. He was able to start it again (something about the battery), and dropped me off soon after. He apologized for the performance anxiety, but congratulated me on being a porn star and keeping the mood up. He said he'd keep in touch over email if there was another gangbang he was putting together and he needed guys he could trust, and I said I looked forward to it.

I never heard from Gary again. Even if he did invite me to another gangbang, it was clear he himself wouldn't rise to the occasion. I did hear back from Betsy and Andy after that night, for they missed me so much that they were hoping to see me at least one more time before they left for good. We met up two more times after the foursome, and happily traded Betsy back and forth just like old times. I wish this tale had a happy end, but unfortunately they divorced a year later. I found out after hitting up Andy and asking how the scene was where they ended up. Apparently their relationship had been wanning for years, and the swinging reignited their passion for only a short time.

After the excitement of the foursome, I soon after kept an eye out for all mw4mm posts, hoping for a redemption or a bigger group. A few months later, that dream would also come true.

To be continued.