Back in the glory days of Craigslist I met this couple in their 50s. I was 20 and still very new to exploring my gay side. I had made a post with a few pictures saying what I was looking for, an experienced man to help me explore more discreetly. They answered saying they could help me explore as well as help me financially. I wasn’t expecting that and of course I was skeptical. But we talked back and forth for a few weeks before I finally agreed to meet them at a gay bar about an hour away from campus.

As we talked I told them I wasn’t interested in getting off or fucking them, I just wanted to explore my submissiveness to older men, servicing them when they needed it. After having a few drinks and hanging out for awhile, they asked me if I would like to go back to their place. I was nervous but I agreed. I felt comfortable enough to go with them.

When we got to their place they didn’t try to rush me into the bedroom or anything, we just sat in the living room with some drinks and chatted. After what felt like an hour, I reached over to the one sitting next to me on the couch, we’ll call him Mark, and started rubbing his cock through his jeans. I was feeling really horny and wanted to show my appreciation to these men for not being too pushy.

I looked up at Mark and asked him if I could suck his cock. He smiled and said “you don’t have to ask boy.” I slid off the couch and positioned myself on my knees in front of him. I got his cock out of his pants and immediately dove in mouth first. I licked and kissed his cock until he was fully hard, and I slowly slid as much of him into my mouth as I could. He moaned in approval. I wanted to make sure I did a good job for him so he would want more after that night. After blowing him for awhile I heard the other man, Scott, move over and sit on the couch next to Mark. He already had his cock out rubbing it. I reached out and grabbed his hard cock and stroked him a few times before focusing all my attention back on Mark.

After another few minutes Mark told me he was going to cum. I started sucking and stroking him faster until I felt his legs tense up and he flooded my mouth with cum. I quickly swallowed and swallowed again trying not to lose any but some still leaked out. I was still pretty new after all. I don’t let that happen anymore. I licked the rest of his cum off his cock and licked his balls once more before quickly shuffling to the right and looking up at Scott.

I had never had two cocks in one day before let alone two at the same time and the thought had me hornier than ever. I didn’t waste any time putting the full length of Scott’s cock in my mouth. He was a little smaller than Mark but I didn’t mind at all. I went to town sucking him while he moaned. I looked up and he was staring straight down at me with a look of lust in his eyes. His breathing picked up and soon after he said he was about to cum too. I greedily picked up my pace even more and not long after felt his cum hit the roof of my mouth. I swallowed every drop I could before licking the rest off his cock. I kissed his balls once more before sitting back on the floor.

We were all exhausted and didn’t really talk much. I asked them if they cared if I slept at their house that night so I didn’t have to drive all the way home and they agreed. Scott grabbed me an extra pillow and a blanket and it wasn’t long before I was passed out on the couch.

When I woke up in the morning there was a glass of water and much to my surprise, $200 sitting on the table next to the couch. There was a note that said something like “we are at the grocery store, last night was great. Please lock the door if you leave before we get back.” At first I wasn’t going to take the money but I thought fuck it and grabbed it. I locked their front door and hopped in my car and made the drive home. The whole way thinking to myself I couldn’t believe what had just happened last night. As soon as I got home I jerked off and shot the biggest load I ever had. I showered and got myself ready for the day.

More to come if you’re interested!