Rendezvous with My First Couple

So it had been a few years since I first hooked up with my first couple Matt and Cindy. Since starting me on my journey playing with couples on craigslist, I had since acquired a body count and experienced several different scenarios. I knew what I was comfortable with, and what I wasn't comfortable with.

One day out of the blue Matt emails me that he and Cindy are coming back to San Diego for another little vacation, and instead of the harrowing task of trying to find a decent guy on craigslist, he wanted to know if I would be willing to meet up and play with them both again. Loving the idea of a rendezvous with the couple that first broke me in, I replied an enthusiastic "yes please!"

It was going to be a similar set-up to last time: they were staying at naval housing, and would drive me onto the property where we could all play. This time it was naval housing in Chula Vista (last time it was in Point Loma) at these giant apartment looking towers. There was a Burger King across the street, and we decided that would be the most convenient place to meet.

While the playdate approached I shared my adventures with other couples with them to show that I had been a busy boy since they first introduced me to the lifestyle. Matt was especially excited, and shared with me photos of the adventures they had been up to with other young men.

One photo they sent was of Cindy on her knees wearing black velvet gloves and stroking a giant 10-inch cock of a seated young guy. There were white pearls of cum all over her velvet gloves and his toned stomach. While hot, I reminded them that I wasn't that big. Matt assured me they remembered how big I was from the last time we played, and how Cindy was looking forward to playing with me again.

The Saturday night date finally arrived and I took the bus down to the Burger King across from their lodgings. We agreed to meet at 7pm, and I arrived at the Burger King a few minutes before. They hadn't arrived yet, so I sat at a table facing the entrance and waited. The restaurant was practically empty, and the two workers on shift didn't give me a second look. 10 minutes later and a car drove into the parking lot, and out stepped Matt and Cindy.

Matt looked like the same stocky gentleman I remembered, now wearing khaki shorts, a peach polo, and a Navy Veterans hat. Cindy on the other hand didn't look any different; still in shape, handsome features, and wearing a light white Adidas jacket and black pants. I flagged them down as soon as they entered, and I gave Cindy a hug and Matt a handshake.

"Ready to go?" Matt asked, and we headed out to the car for the short trip across the street. Cindy stayed in the front seat this time since we'd be all over each other in mere minutes after parking, and I sat in the back with my ID out and ready.

I was incredibly anxious the first time with them driving through the checkpoint in Point Loma, and even though nothing happened last time, I was still a little nervous going through this checkpoint. Of course nothing happened, and the guard waved us through after giving a brief glance at the IDs.

The property seemed like a maze, and after a few minutes Matt found a decent parking spot. Under the cover of night and a few dim lamps, we made our way to the tower they were staying at.

A short elevator ride later and we had arrived at the living quarters they were staying at. It was a much nicer layout from last time, a lot more spacious and resembled a decent hotel. There was a nice looking couch with a big dresser and TV across from it, a comfy looking reading chair next to the large bed, and a decent size bathroom as well.

Matt had left the television on and Bill O'Reilly was blaring, shouting about immigrants or something. I hoped that the TV would be turned off, because having him as background noise didn't seem like the appropriate choice.

Thankfully, Matt turned the TV off. "You both get comfy, I'm going to change into something sexy," Cindy said, giving me deja vu from the first time she told us almost the exact same thing. Matt and I started to undress, and I made a pile of clothes next to the couch. To be extra prepared, I took the condoms out of my pocket and placed them on the nightstand.

Matt and I then sat naked next to each other on the couch, and I noticed that he looked like he had gotten a little grayer since the last time I saw him. Still a bit portly, he stroked himself hard getting ready for Cindy. I joined him, stroking myself as well.

A few moments later Cindy emerged from the bathroom in white lingerie, radiating in the dim lighting of the space. "Oh good! You're both ready for me!" she noted. "Goddamn you look smoking, Cindy!" Matt commented. "Love the choice of lingerie," I added, making her feel sexy.

Cindy seductively walked over to us on the couch and dropped to her knees in front of me. "Ah yes, I definitely remember you," she whispered to my now hard cock, feeling its thickness with her hands. I started to feel the anxious tingles again, but this time they were from excitement. I had always hoped to play with Matt and Cindy again, and it actually was happening.

After stroking me to her preferred hardness, she then leaned over my lap and slowly sucked my cock. Her warm inviting mouth caused me to rest my head back against the top of the couch. My fingers glided through her hair and held steady, enjoying her bobbing motion. She took my dick out of her mouth and slowly licked it from the base to the head, giving it little kisses as well. It was a welcomed reunion to be sure.

As she began sucking and bobbing again, Matt reached over and placed his hand on the back of her head to help with the motion. Not forgetting about him, she reached over to stroke his cock, getting him ready for the eventual switch. "Yeah baby, suck his big dick," Matt cooed. Cindy was enjoying herself, as was I, letting out low moans as she continued to suck.

Eventually she leaned over to Matt and started sucking him, while leaving one hand on my dick to keep me in the mix. This back-and-forth went on for a little while before Cindy said that her knees were starting to feel a little tender. I offered her my seat on the couch, and asked if I could please her next. She smiled and agreed.

I got on my knees while she stood over me, and I slowly kissed up her legs until I got to her white panties. I removed them slowly while still kissing her legs. I was pleasantly surprised to find that she still kept a little trimmed muff, and I kissed it before kissing and licking her pussy. She moaned, and with her hands rested them on the sides of my head, keeping me nice and centered and I continued to refamiliarize myself with her taste and scent. She was still as delicious as ever.

My hands wandered, first cupping her ass, then slowly gliding them up her slender torso and over her white bra. Matt had gotten up from the couch and appeared behind her, kissing her neck while unhooking her bra for me. With her breasts now exposed, I was rubbing one while Matt rubbed the other, and Cindy was in pure bliss.

"You know, we have a big bed right there we can play on. We don't need to stay here on the floor!" Matt reminded us. We all laughed and made our way to the big bed a few steps away.

"Can I continue to eat her out before anything else happens?" I asked. "I kinda wanted to enjoy her more last time." Matt gave me a hearty thumbs up, and Cindy got comfortable on the bed. I slid-up the middle of the bed and she parted her legs for me, welcoming me back to her warm nirvana.

I enthusiastically picked up where I had left off moments ago, and eagerly ate as she grabbed my hair in pleasure. I soon added a few fingers, and she was getting more wet by the minute. Matt had slid up next to her on the bed and kissed her neck while playing with her breasts, tweaking her nipples and helping get her completely aroused.

Her breathing started to get a little shallow, her legs began to quiver. "Oh god, keep doing that," she whispered. Her grip on my hair tightened, and I knew she was going to come soon.

"Oh god, I'm almost there," and I kept rhythmically fingering while simultaneously sucking on her clit. Seconds later and she came hard, giving a soft scream of pleasure. My head was suddenly in a vice, and I rode out her bucking. I intensified the fingering to help her continue coming, and her head remained bent back and deep in the pillows.

Slowly her grip lessened, and she was panting from exhaustion. "Good job, honey! You were so fucking sexy!" congratulated Matt. "And good job to you as well! She loved it!" he told me.

When Matt and I had started planning this second rendezvous, he had mentioned to me that he was starting to explore his light-bi side, and was wondering if I felt comfortable at any point during our meet-up, that maybe he could suck my dick. While I had a very uncomfortable experience with one couple in the past, I wasn't going to let it limit my exploration of what I was into with other couples.

And since Matt and Cindy had introduced me to playing with couples and made me feel comfortable the entire time, I told Matt that as long as I felt comfortable with the situation, that I would be open to the idea of being blown by him. I was not interested in returning the favor, or anything more. He completely understood and assured me that it would be oral only, and only if I was comfortable.

"Hey Jason, while we let Cindy catch her breath, how would you feel about me blowing you?" Matt asked. The time had come, and I could tell he had definitely been looking for the right opportunity to ask. I had grown rock hard by making Cindy come, and I stood next to them on the bed with all (almost) 8-inches exposed and ready for whatever was next.

I didn't feel creeped out or pressured, so I decided 'fuck it' and agreed. "Can I position this chair facing Cindy so I can watch her play with herself?" I asked. "Yeah sure, whatever helps you feel a bit more comfortable."

So I moved the comfy reading chair to the side of the bed and sat down with Cindy in full view. Matt got on his knees in front of me and assured me, "I'm not gay, I just think it's okay for a guy to be a little curious is all, you know?" trying to act like this was the most normal thing in the world.

I nodded my head in agreement to try and make him feel more comfortable about it, but he continued. "I don't normally do this, but when in Rome, you know?" I had the feeling that this wasn't Matt's first rodeo, but he had to convince himself that he was still 100% a masculine hetero dude, and that enjoying sucking dick wasn't gay in the slightest.

And with that, he took my dick in his hand, and went down on me. He lacked the skill Cindy had, but he seemed quite happy sucking my dick while stroking me. His mustache threw me off, and I could feel my erection begin to waver.

Looking to Cindy for help, she leaned back against the pillows and headboard and started playing with herself in front of me, biting her lip and getting into touching herself. That was the key, and soon I was getting hard again watching her enjoy herself.

I wanted to plunge right back into her pussy mouth-first, and the thought of doing so made me grow. Matt stopped sucking me for a second to comment, "He's getting hard! He likes it!" oblivious to the fact that it was 100% Cindy who was causing the erection.

Both Cindy and I gave each other a silent glance that said, "Sure Matt, sure." Matt continued for a few minutes, then stopped because his jaw was starting to get a little sore. "Thanks for letting me do that," he told me. "I don't do it often."

With Matt's fantasy fulfilled, Cindy beckoned me over to the bed to claim my prize. I grabbed a Magnum from the nightstand and slipped it on before getting on the bed with her and laying down.

She positioned herself on her knees over me, took my cock and aimed it under her, and sat down. We both let out a moan, and she took a second to adjust to me. I was ready to fuck her so bad that I had to restrain myself from completely letting loose.

She bent over to me and whispered in my ear, "Thank you for letting Matt do that. You made his night," and I whispered back, "No problem." Matt now sat in the comfy reading chair and stroked himself as he watch me and Cindy fuck, with her riding me as I grabbed hold of her tits and hips. She got into a prefered bouncing rhythm, and I did my best to match her.

In the heat of the moment she leaned forward again, but this time to kiss me passionately. I returned the kiss while our fucking continued. Our tongues danced in our mouths, and I was fully aware I was probably tasting some part of her husband, but I didn't care. I was fucking a sexy again MILF, having the absolute time of my life, and nothing was going to ruin that moment in time for me.

I eventually had her rollover on her back, and I proceeded to continue fucking her and showing her what I had learned since we last met. Her tits bounced up and down while she writhed in pleasure, clawing at my arms and back, wanting all of me. My erection was harder than diamonds, but I did want to cum for them this time since I robbed them of it last time because I was too nervous.

I then positioned her on all fours, and Matt took the opportunity to get up on the bed and sit against the headboard and have Cindy suck him while I fucked her from behind. Each thrust from me caused her to moan, and she went back and forth between us like a tennis match.

Finally, I felt the familiar sensation of needing to come soon. I warned them as I started picking up the pace behind Cindy, and she instructed me to come to the side of the bed and come on her face when I was seconds away.

I waited almost too late, and quickly jumped off the bed, ripped the condom off, got right next to her while standing on the side of the bed, and stroked/aimed at her face. At the last second Matt's face appeared at her level, and they both had their mouths opened. I wasn't expecting it, but it was too late.

Globs of come shot out of me, and splashed against their faces making an absolute mess. "Oh no! Friendly fire!" Matt said, with a little of my come on his mustache. I had let out a grunt of ecstacy from the intensity of the blast, and soon after Cindy and Matt leaned over the side of the bed to both suck me, recovering every drop.

They kissed while licking me, savoring the moment. I felt more comfortable with both of them sucking me than just Matt, so I let them enjoy it while I recovered.

While I went to rest in the comfy reading chair, Matt and Cindy proceeded to have reclamation sex on the bed, my come still drenched on their faces. Matt thrusted into Cindy in missionary, and only lasted five minutes before coming inside her. It was a big night for him, so he was probably excited to come as soon as possible.

As I got dressed, Matt switched the TV back on and a new FOX host was yelling through the TV. Matt and Cindy washed-up, and Cindy hugged me goodbye. Matt gave me another hearty handshake, and said I was at the top of their list the next time they were in San Diego. I was so grateful for the opportunity to play with them again, and told them I would be ready for next time as well.

I took the elevator down to the ground floor, walked through the maze to the front gate, and passed the checkpoint without any hassle, even giving the guard stationed there a head-nod as I passed. As soon as I got home, I masturbated at least two more times as I replayed the encounter in my head, Cindy the main star.

I continued to keep in touch with Matt via email, but we never had the opportunity to meet-up again and eventually lost touch. In some of our final messages, he had told me he was flying out solo to San Diego for work, and pitched that I post ads on craigslist for any women who might have a father/son fetish. I was doubtful anyone would be interested, but still played along.

When I asked him for a photo to include, he sent me the same one of him shirtless on the beach from 30 years ago, looking nothing like he did now. I had myself a chuckle, thinking that he'll never update that photo as long as he continued playing online. And no, no one responded to my ads about a father/son duo. Probably for the best.