first time MM | 2016

Although I have always considered myself a totally straight male, I have had fantasies about guy-on-guy sex since I was very young. Aside from some aborted pre-teen experiences with a friend though, nothing really came of these feelings. Now I am in my late-forties and the thoughts are as strong as ever. Oddly I am not attracted to specific guys. I just had a general feeling that I wanted to suck a cock, I wanted to fuck a guy, and more than anything I wanted to be fucked by a guy. Recently I decided to act on these feelings finally.

As a long-married guy who has never cheated, the first thing I did was got permission from my wife. Hard to believe, yeah, but she was OK with it but did not want to know anymore about it. She really just said to take care of this need. Because of my position -- monogamous and with a wife -- safety was my primary concern. This pretty much ruled out most of craigslist as the ads there are for "cum dumps" and other scary sounding options. I finally decided what I would do is post for a newby -- I know its cliche -- and I would insist on someone age 18-19 only. In addition I would insist on recent medical testing for HIV and would provide the same. I made a post on CL describing exactly what I am decribing here -- a plan for a one-time (or more) meeting with all the trimmings, to take place in a hotel. As I live in Orange County and work in San Diego, I posted my ad in both CL versions. My ad really was different from the typical CL ad and I did not know what the response would be. The guy-on-guy section of CL in the OC area is really a cesspool.

As it turned out I got many responses, but most were from guys who did not match my criteria at all. Lots of scary types. I did get responses from four different guys who sounded pretty ideal though. I exchanged e-mails with all of them, and while all four seemed legit, I finally settled on Shane.

Shane claimed to be 18 and a virgin. He said that he too thought he was straight but had always wanted to try a guy, but could never bring it up with any of his friends. We exchanged several notes before meeting, as I really wanted to make sure that this was not going to be a case of a young guy getting taken advantage of. He stuck with it though and we agreed to meet at a hotel in Carlsbad. We had exchanged photos and HIV test data in advance. He was a pretty average looking white guy, a little nerdy looking but also healthy looking. Average weight and build.

I got the room a little early and took a shower. I had purchased some disposable enemas as I had read that a cleanout was good before anal. I used one myself and it seemed to do the job. I had been relaxing for about 20 minutes when Shane arrived. I was really nervous.

We said a strained hello while checking each other out. We talked for a bit and kind of talked about our past thoughts about having sex with a guy. I had no doubt his story was accurate as he looked a little awkward. A very nice guy but not that social really. I suggested he might want to take a shower and then I could give him a back rub. He went and washed up.

He came out wearing a towel and an obvious boner. I knew from our photo exhange that, like me, he had an average or smaller-than-average cut cock. That seemed fine to me. I had stripped to my boxers and honestly I was ready to blow already. I asked him to lay on the bed face down, and when he did I began to give him a nice slow massage of the back and legs. I brushed against his toweled ass cheeks a few times and then finally unwrapped him -- awesome view! I continued to massage, working on his ass cheeks and slowly moving a finger toward his visible nut sack. I touched his nuts and the skin was very soft, probably like my own but it felt so different to touch someone else. I asked him if he wanted an enema and explained why, and he agreed. I was really excited about that and took another Fleet enema and lubed it up. These things have small tapered tips, and come with lube which I smeared on the tip. So far I had not touched his asshole. I asked him to get up on his knees and press his chest to the bed. I put the tip to his asshole and very slowly pushed it in. He seemed to really enjoy this and so did I. His asshole was hairless and tight and puckered. I pushed the enema tip in 2-3 inches and then slowly squeezed in the liquid. I then pulled it out -- he moaned -- and I told him to go in the bathroom, hold it a few minutes before going, and then take a second shower/rinse.

He was back in about 10 minutes, still rock hard. I asked him to lie on his back and I would give him a front massage. I started on his chest and covered every spot except his privates, then finally I started to touch his balls and cock. It was electrifying for both of us. I massaged his balls and stroked his cock. I was ready to suck it. Now came a decision though. I had planned on us both using condoms even for oral, unless he looked totally clean. He did look clean and I really wanted to suck him wihtout the protection. I decided it was OK, and I took the cock in my mouth. This was a defining moment for me. The warmth filled my entire head and it felt very natural with his cock on my lips and mouth. I moved slowly up and down and he began to squirm and moan. Time for another hard decision -- do I finish him off? I really wanted him to fuck me later, but I decided he could come up with two loads at his young age, so I continued to suck him. Just a few minutes later he blew a huge load into my mouth. His cum was much thicker and richer than mine is these days. It tasted delicious and I enjoyed letting it run over my tongue and down my throat. His orgasm was unreal in its intensity. When he seemed done I lay down next to him.

I was worried that after coming so hard he would lose interest or feel guilty, but he stayed in position. I suggested he roll over for some more massage and he did so readily. He seemed to really like being directed. Once he was on his front, I did not waste any time. I started to lick the rounds of his butt, moving in closer and closer to his puckery bit. When I finally got to his pink little target, he was back to 100% horny again. I licked him for several minutes, poking my tongue right into his hole, and then got some lube (I had brought lube and condoms) and put it on his pucker hole. I had trimmed my fingernails really close and tried to push in a pinky. It went in as the anus gave way slowly. Inside was incredible warmth. I pulled out the pinky and tried the same with an index finger and it too slid in. I could feel his prostate and gave him a massage there too. Finally I pulled it out and prepared to fuck him. After blowing him I had chatted with Shane about the condom issue. We agreed we were both willing to go without condoms as we both seemed clean. This surprised me as I did not think I would be as safe a bet for him, but he was OK with it. I put a lot of lube on my cut cock and pressed it against his asshole. It did not yield easily. I had to push and kind of rotate it to make any progress, and he had to flex his sphincter also. It started to go in and the feeling was incredible. Finally it went in the full length and I was inside. Wow! I began to slowly move out and in. The feeling was not at all what I had expected. I figured anal would feel like a super-tight band right at the anus and then be looser once inside. Instead it was really just very tight all the way. Honestly I think vaginal sex is better by comparison, but this experience had the incredible guy on guy aspect and so it was amazing in its own way.

After a few minutes of pumping I pulled out -- what a rush -- and had Shane flip over. He was not fully hard but looked really happy. I lay down on top of him and pushed back inside of him. This time it was a lot easier. This front approach was totally different feeling. Being able to see and touch his cock, and see his face, added a new dimension. I kept pumping and after just a few more minutes had an explosive orgasm. He was activeley fucking me the entire time, bucking and pushing wildly.

I rolled off and took a few minutes to reflect, and he did the same. After a few minutes he reached over to check my cock, which amazingly still had some life to it. He tentatively felt it, then all at once put his mouth around it. It felt incredible, but after just ejaculating there was no way it was going to happpen again. Maybe he just wanted to tast the jism that remained.

He asked me if I wanted to roll over and of course I did so. Now was the final event! He gave me a brief massage but I could tell he was excited and he quickly got some lube for my asshole and his cock. He pressed against my hole and at first I did not feel any give at all -- total resistance. I tried to relax, and then he decided to try a finger first, which was a great idea. He worked in one finger and the feeling was great. He then worked in a second finger and I was feeling a sense of euphoria. Finally he pulled these out and tried to fuck me again. This time, it started to work. I tried to bear down -- like taking a crap -- and suddenly my ass seemed to pull him in. Incredible! He made a moaning sound and slowly began to pump in and out. I could actually feel his cock in some detail inside me, and really I liked it a lot. He did not change positions but instead came in just a few minutes. I could not feel the sperm inside me like some people say they have, but I could feel his cock throbbing it out. He pulled out and collapsed next to me. I reached back and could feel a small amount of his ejacualate leaking out.

At this point we were basicaly done and it had been great. I could not resist though, in such a post-sex glow, pulling him over next to me. Cuddling I guess you could call it, but it just seemed right. Weird I know. We stayed that way for 30 minutes or so, then we each took a shower and departed. This was just last week and we have not talked about whether to get together again. It was incredible sex so I would like to, but I have to accept that he is at a very different place in life. I would be happy to make this a monthly event or more. If there is more I will share it here. He introduced me to reddit and asked me to post this -- hey Shane!