After my first successful hook-up with a couple, I was hooked. I was never a big consumer of alcohol or recreational drugs, but this lifestyle was my new high. Craigslist was my dealer. Newly confident thanks to my experience with Matt and Cindy, I started posting more and more on m4w and m4wm, and replying to posts on mw4m and w4mm (just in case I was that lucky).

At first it was spam and single guys again, but eventually women and couples started responding. Almost all of them ended up not working out because I was too young, too inexperienced, or the timing was off (I sometimes had a night shift at work or night classes). I even passed on a few couples because there wasn't a mutual attraction, or some of the couples wanted me to play with their husbands, which I was not interested in and said so. After several months of no results, I decided to change things up. Instead of wanting to have another threesome with a couple, I posted an ad offering to be a cameraman for a couple. I knew how to work a camera, and did have experience filming with a camcorder. After a few weeks with that ad, finally a guy reached out to me with a proposition.

"Are you interested in taking pics of my wife, and then fucking her while I take pics of you both?" Immediately my dick got hard at the thought, and we started chatting and exchanging information. His name was Andy and her name was Betsy. He was 36, and she was 31. He was a Navy mechanic and was buff, in shape, and a bit of a bro. Betsy was a redhead, pale with freckles, petite, and wore chic dark-framed glasses. They had an exhibitionist fetish, only had a handful of threesomes at that point, and she wanted a younger guy this time. I gladly volunteered as tribute after they sent over a few photos. They lived in Point Loma and had a 2-year-old, so we tried to plan for a weekend where they could leave their kid at their mother's in case everything went well after the public meet-up.

The meeting place? Hooters in Mission Valley next to the mall. Not my first choice, but apparently they enjoyed going there with Betsy wearing revealing clothing to try and compete with the servers. I personally had only been in a Hooters one other time, years earlier after a friend wanted to get chicken tenders after a concert. I just didn't see the appeal of women highlighting their tits and ass when they clearly only worked there as a last resort. I arrived outside and waited, dressed in a pair of jeans and a Ramones t-shirt. Once again I had a wad of condoms in my pocket in preparation, and I nervously cradled them in one of my hands. I then saw Andy and Betsy walk towards me from the parking lot, Andy with a tight-fitting shirt over his muscular body, and Betsy wearing a giant XL black graphic t-shirt, and nothing else underneath. I discovered there was nothing underneath because as soon as Andy called my name in recognition, Betsy quickly flashed me her shaved pussy. I was in complete shock, and they both laughed at my reaction. It was early evening so it was already a little darker, but her pale white skin drew my attention like a lighthouse, and her bald pussy the shiny bulb. No one else was around to see it, and if they were, they just weren't paying attention.

We shook hands, said hello, and went inside to grab a bite to eat and chat. The restaurant was packed, and we were seated at a table in the middle of the room. They ordered drinks and appetizers, and I ordered a basket of fried pickles because I had no idea what to order and was a little nervous. Betsy was swimming in the oversized black shirt, and I kept nervously looking around to see if anyone else had clocked her outfit. They were loving the situation, having this secret while being surrounded by strangers. We talked a little about our lives, keeping things PG (I was worried someone would overhear us), and then the most bizarre thing happened. I recognized one of the servers as a girl I went to high school with but hadn't talked to or thought about since graduation. I looked at her straight in the eyes, and she didn't give any indication that she recognized me. I then started to quietly freak out. What if she told mutual friends she saw me with a couple, the woman wearing nothing but a giant t-shirt? Clearly they were SWINGERS and Zeke was a PERVERT. But again, she didn't seem to recognize me. That threw me off for the rest of the meal, and I suggested we walk and talk around the surrounding area after they were done. They loved it because it would mean walking around more, and more potential flashing.

We finally were able to talk about kinks, what they were into, and what they were expecting from me. They thought it was hot that I had only been with one couple, an older one, and Andy made a similar remark that Matt made: "Man, I wish Craigslist was around when I was younger! I would have been fucking so many MILFs!" And Betsy laughed at that. When I asked about how they wanted me to frame shots of them fucking, Andy then informed me of what they actually had in mind. "I actually get off watching Betsy fuck other men. She enjoys it too. Yeah, I'll join at the beginning probably, but I'll actually be the one taking pictures of you both. You just focus all your attention on her. Think you can manage?" And with that, Betsy flashed her pussy again at me from under the t-shirt. I was more than happy to oblige.

I didn't drive at the time, so I took the bus and metro everywhere. When we were ready to head back to their place, I hopped in the backseat of their truck and Andy drove us all home. I was hoping Betsy would join me in the backseat, but the longing for her became part of the foreplay. A short time later and we arrived at their apartment complex. It looked a little sketchy as we walked through the endless hallways, and finally arrived at their place. Inside, the place was small, and pictures of them and their baby were plastered all over the walls. The kitchen was by the entrance, as was a bed in the middle of the living room next to a sofa and TV stand. Apparently the baby's room took up the only master room in the unit, and they slept on the bed in the living room. There was a big pink fuzzy blanket on the bed, and a bottle of scented lube on the nightstand. They invited me to sit on the couch and Betsy was going to give me a show.

Andy and I sat on the couch, and Betsy immediately took off her giant shirt, revealing her heavenly thin body. Small perky tits, beautiful bald pussy, and a smattering of freckles all over. My jaw was on the floor. Could I really be this lucky? She began to sway and dance a little, before coming over to me and sitting on my lap, grinding on me slightly. She leaned over and kissed Andy as she did it, making sure he was enjoying the show. I slowly rubbed my hands all over her smooth body, and made sure to get a nice handful of her breasts. She also smelled amazing as I kissed her back and neck. She gave a soft moan, enjoying my exploring hands, and started to grind a bit harder. My cock began to throb instantaneously. I was worried I was going to wake-up at any second.

"Mmm, he's getting hard," she teased Andy.

"Well babe, you better take care of that, huh?"

"Mmm I will!"

And just like that, she turned around to face me, getting on her knees. She went to unbutton my pants but I was already unzipping as quickly as possible. The jeans came off, then the boxers, and my hard cock was ready for its close-up. She gleefully grabbed me with both hands and stroked, feeling my girth and excitement. "Damn, he's big! Are you sure you're going to be able to fit all that in your mouth?" asked Andy. "Let's find out," Betsy replied.

She licked up and down my shaft a few times to gauge the size, then took me in her mouth, almost reaching the base of me before choking. Andy reached over and helped hold her head down, making sure she was being a good hostess for her guest. She came up for air, laughed, and continued to suck. And it felt great, she knew what she was doing. After enjoying the view for a few minutes, Andy got up to retrieve his digital camera. He came back and started taking pictures, making comments to Betsy as he snapped away. "Yeah take his whole dick, you like that don't you?" Her replies were muffled, and the vibrations added to the pleasure I was feeling. After receiving a wonderful welcome for several minutes, I asked if I could eat her amazing looking pussy and return the favor. She was happy to be offered, and got up and walked over to the bed a few steps away. She laid down on her back, spread her legs, and called me over with her fingers. I quickly got my shirt and socks off and almost dove head-first into her crotch. I got up nice and close to it, admiring her beautiful bald pussy. I noticed the slight visible C-section scar a few inches above, and it somehow made it hotter, knowing she was a certified redheaded MILF. She was about to be my personal redheaded MILF for the rest of the night. I entered a few fingers to feel how tight she was, and she was already dripping wet at that point. I could hear her husband taking pictures behind us, and the flash was going off every other time because of how dim/dark it was. She moaned as I started to finger with one hand, and sensually grab her ass/hip with the other to steady myself. I leaned forward and started licking her clit and pussy, and she tasted amazing. I was rock hard, face-first in a delicious bald pussy, and having the entire experience documented by her husband.

A rhythm was found, and soon Betsy had placed both of her hands on my head, steadily thrusting her pelvis into my face to intensify the groove. I had to remove my fingers to get a better placement with my mouth, and within minutes the build-up became too much for her and she came. It was short and quick, but still left her quaking. "Oh fuck!" she whispered, riding it out. I became immensely pleased that my performance got her there, and Andy also was thrilled. "Fuck yeah, babe!" he crowed. When I looked back to show him my thankful smile, I discovered he was stripped down to nothing, and semi-hard. I had been so focused eating out Betsy that I didn't even hear him get undressed. He gave me a high five while Betsy caught her breath, then mentioned maybe I should give Betsy a ride. "It's her specialty," he said proudly. I was so ready to fuck her brains out at that point that I quickly exchanged places with her on the bed, stroking my hard cock. "Let me get a condom really quick," I said, suddenly remembering. "It's no problem, dude. We're clean, you're clean, we can just skip them. She likes it bare anyway." I'll admit I was already too caught up in the moment to care, and decided to let it happen and worry about any possible consequences later.

Betsy giggled as she got in position, and straddled me. She was so tiny, and I rubbed her pale white legs in preparation as she stroked me a few times, got the scented lube from the side table, applied a little on me, and slowly lifted up to place my head at the entrance of her pussy. She slid me in, and slowly sat down to fully take me. She was so unbelievably tight, and I grabbed onto her hips and moaned. Andy frantically continued taking pictures, sharing encouragement throughout. Betsy began to slowly bounce and grind, massaging her small breasts as she did. We were moaning with pleasure as we got to know each other with every thrust. Andy was true to his word, she knew how to ride and all I could do was hold-on tight.

Betsy continued to ride for a good twenty minutes, and I'm proud to say I kept up and was able to prevent myself from coming too soon. We were both glistening with a mist of sweat, and she finally asked if we could change positions. I agreed, and she positioned herself at the end of the bed, on her back and legs fully spread. I stood before her in a bit of a hunch, entered her again, and leaned forward to kiss her neck as I fucked her, tasting her sweat. Andy quickly got every angle of the fucking, and at one point when I got a look at his back, I noticed he had a giant "JESUS CHRIST" tramp stamp in a bold old timey font. "How odd," I thought as I continued to fuck his wife. It was discussed beforehand in our email chats that when I would need to cum, aim for her face. Andy got immense pleasure from seeing guys cum on Betsy's face and glasses, and for her to wear it around as a trophy for a few minutes. I had started to speed up with the fucking, and every thrust was eliciting a vocal response from her. I was starting to get overstimulated and realized I was about to cum. "I'm about to cum!" I announced as I quickly exited her. "The face! The face, dude!" Andy commanded, and Betsy got into position to receive my load, eyes closed and mouth open. I aimed and fired, ropes of my cum plastering her dark-framed glasses, cheek, forehead, and even a little in her hair. I let out a massive grunt and continued to stroke out the remaining drops, and Andy let out a celebratory "Whoo!" as he snapped several photos. Another high-five occurred, and Betsy laughed at how happy Andy was. "Now get me a towel! It's all over my glasses!" she demanded. Andy quickly went to the kitchen and got paper towels for both myself and Betsy, and I noticed all the excitement got him a little harder. He was average size, but his buff muscles and body type made him look smaller amongst all the muscles.

I cleaned up and got dressed again, as did Andy, but Betsy remained on the bed in all her naked glory. Andy was thanking me profusely for fucking Betsy, and I was thanking him for the opportunity. "If you maybe want to come over again sometime, that would be great! I'll even join next time, I promise!" I gladly accepted the invitation. Andy drove me back to the nearest metro station and dropped me off, again thanking me and promised to share some photos with me within the next few days. I took the metro back home exhausted with the biggest smile on my face.

For the next year I would meet up with Betsy and Andy at their place, with Andy picking me up from the metro station, taking me to their place, where a naked Betsy would greet me. Andy did join in on the action as promised, and we spit-roasted her, swapping between her pussy and mouth, have her take us both in her mouth, and then play one-on-one with her while the other took pictures. It was pure bliss every encounter, and the pictures were always wild. He did attempt to film us with their camcorder at one point, but the file was corrupted when he tried uploading it to his computer so we could never see it on a screen, just the tiny viewfinder screen on the camera. They eventually got busy with life, work, and their young child, so the visits slowly became less frequent. It was around that time that Andy suggested I maybe start looking to play with other couples so I could still get some action (we both promised not to see other people while playing together over the course of the year. Less messy, less chances of getting STDs). They were officially going to take a break for a while, but that wasn't the last time I would play with them. That opportunity came several months later, when Andy arranged for a gangbang to happen for Betsy. And I was one of the invited guys.

That's a story for a future post.