In a previous posting (Younger & Wiser 1-3), I shared an autobiographical story of meeting Josh, a 33 year-old guy from my cross-fit class and how he initiated and introduced me (a closeted, 48 year-old MWM) to sex with another guy. In that story, we both got off using just hands and mouths. This story is about how he taught me to be fucked.

(from the first time Josh and I got together)...Laying on the bed, naked and still a little sticky with cum, Josh asked how I was feeling and I told him that both the intensity of my arousal and orgasm were unlike anything I had experienced since I started beating off around age 12. He smiled a shit-eating grin and said that he has "super sperm containing magical powers and it has that affect on everyone" (such smart ass). I was into the fact that he was being funny and not all sappy and touchy-feely. While I'm much more attracted to guys with some depth and character, I'm not attracted to feminine or dramatic guys and was not into or ready for romantic experience. Josh was on the same page -- our encounter was more like a sport or a workout than it was intimacy. I never identified with other gay guys nor could I ever imagine being in a relationship with another guy where one of us plays a feminine role and the other a masculine one. Early on, I thought that's what happened in a gay relationship, but I know better now. What we had just done was incredibly erotic but never felt like I was compromising my masculinity. As we were still lazily laying there and avoiding a shower, I told Josh I was so envious of his courage to "proposition" me when he hardly knew me yet could clearly tell I was married. "That takes balls, I just don't have," I said. "I did not see it at first," Josh said "but after the 2nd or 3rd time at the gym, the way you glanced at me once caught my eye and I started to watch you." "You are very skilled at averting your eyes but one time when you were behind me, I caught you totally staring from the mirror." He said he "learned early on that the eyes tell no lies" and "while you hid it incredibly well, I knew there was something going on and I took he chance." He also said that there was a hunger and vulnerability that he could also sense (I called bullshit on that one and told him he read too much chick lit -- we both laughed). He kissed me, smiled that Chris Pratt smile and said lets get cleaned up. I took a quick shower and told him that I needed to get home and we agreed that we'd see each other at the gym the next morning. A long bro hug, a grasp of his rocking ass, and I was off.

That night after my wife went to bed, I was fighting the angel and the devil on my shoulder. I was so wracked with guilt for what I'd done, the vows I'd broken, the line I'd crossed ("does this mean I need to check the " gay" box now?") but at the same time feeling a sense of relief and accomplishment. Something I'd thought about for a long time and to meet someone like Josh who was so unbelievably patient, mature, grounded and fucking hot! I finally fell asleep at 2 and my alarm went off at 5 to make it to the gym by 6. When I arrived, Josh was on a mat stretching in downward dog position. ass-in-air stretching his gym shorts -- almost nothing hotter (never realized I was such an ass man). He saw me, we did a quick fist bump and he said "time for a coffee afterward?" and I said "you bet I do." At Starbucks he again asked how I was feeling after I'd "slept on it", and I told him about the mental breakdown the night before but that I'd worked though it. I told him I thought we had a nice friendship going and really look forward to developing it. He seemed to sincerely agree. He told me that he was heading west for business that week, and was going to spend a few days with his folks totaling about a week of travel. He said he'd love to show me what other fun guys can have together when he gets back, if I was up for it." I said in a smart-ass way "look into my eyes to see if you can figure out my answer." after a quick glance he said, "that's a definite yes!" "Can you connect after work next Tuesday?" Without even checking I said "yes."

That was a long, frickin' week. I imagined a dozen different things we'd do and beat my cock raw thinking about it. I think I came 5 out of the 7 days he was gone. I'm honestly not sure where all that semen came from in my body -- each load was big.

I was like a teenager when it came time to head over to Josh's apt. I'd seen him that morning at cross-fit and he seemed as excited as I was. When we left the gym that morning he said, "hope you don't mind but I'm making that ass mine tonight." I was overwhelmed with lust, excitement and anxiety.

I arrived at his house with a bottle of bourbon anticipating the need for a little liquid encouragement. First thing he said when he greeted me at the door is "today's the day you learn to fuck," follow me. He poured me a bourbon, helped me out of my clothes and led me to the bathroom where sitting on the counter was a Fleet disposable enema package. He said read the instructions and use it then I'll be in to jump in the shower in about 15 minutes. I had recently had a colonoscopy so I knew how to use the enema. I inserted, waited and let it all out then I did it again. Super clean water the second time so I called for Josh and told him that I was getting in the shower. Within minutes, his naked, slightly furry body joined me and we started to soap each other up. Once again, that fine hairless, round ass mesmerized me and got me rock hard much more quickly than Josh but nothing a few strokes of my soapy hand could not manage. He asked if I was ready to be fucked and I said "Oh yeah!" he then reached around, started rubbing my ass, then crack then worked his way to me hole. I turned around and bent over, giving him full access. He cleaned rubbed and scrubbed the whole area and finished by sliding a finger up my ass. "This is crazy tight," he said and I responded "that's because it was built as a one-way street (I'm not nearly as funny as he is). Not missing a beat, he responded by saying "officially notifying you that road-widening will commence on your street today" and proceeded to gently add a second finger. I gotta admit, it felt neither good nor bad. It just felt like my but was full. He gently rubbed his fingers in and out and it started to feel better, but quite frankly, the rimming we did the previous week got me much hotter. We rinsed, still with his fingers in my ass and he shut off the shower. He then removed the two fingers then led me back to the bed where I had another drink (I had "inebriate and lubricate" running through my mind).

Josh asked if I was ready and I said "yeah!" and he proceeded to apologize that he was going to be a little clinical in his instructions but said that I'd really appreciate it. He then got serious for a minute and asked if I wanted him to use a rubber. I had a slight panic while he rationally talked through the pros and cons of protection. He talked me through how he was clean and disease free and in my head I had often fantasized about feeling a guy's cum shoot in my ass, so bareback it was. I hoped I was not making a big mistake, but it felt right. Josh explained that he was going to lay on his back and that I was going to squat on top of him, lowering my ass onto his cock. He said that would let me control depth and pace and then we would switch to missionary when I got comfortable and he'd pound the hell out of my prostate. Josh pulled out the lube and proceeded to generously apply it deep in and around my asshole. I then lotioned up his cock. It was like stone it was so hard. While he had a pretty short cock lengthwise, it was super fat and I got a little freaked that it would stretch my hole and make me hurt for several days. With both my ass and his cock literally dripping more lube than I'd ever used, I start to carefully kneel over my bud's dick. First the head, no problem; no pain. Then the shaft started to enter my hole and I could feel my ass walls clamp around his cock like a giant suction tube. His cock was fat! At this point it went from feeling OK to bad -- much more painful than I dreamed, but I was determined to try to block the pain. All the while Josh was describing what was physical going on (the head of my dick is in my anus; the anus is like the lobby for my ass; it roomy and comfortable. Now the tip is entering the sphincter, which is like a set of heavy doors that the air has sucked closed). He saw me grimace and said and said "I know it sounds weird, but push your cock muscles like you are trying to push my cock out of your hole." "It will loosen it up and make it easier for my tip to open those doors." That definitely took away the intensity of the pain and he started to get some movement deeper in my hole. He instructed me to move my hips in circles and slightly move them up and down pushing a bit further which each stroke. After what seemed like a half hour (but in reality, less than :10,) my ass crack was on his pubes and I could feel his cock expanding in my ass. The feeling went from sharp pain to dull pain, to a pleasantly full full feeling to a feeling of intense pleasure. Josh instructed me to really grind my cheeks deep into his pubes to feel his dick on my prostate. I ground my ass in circles counter and clockwise until I felt it. "Holy shit" is all I said and I continued to grind my hairy ass up and down and back and forth on his pelvis. Josh's eyes were closed an his moth was wide open uttering soft, guttural moans with an occasional "your ass is like a vice." Despite that, Josh instructed me to use my ass muscles to squeeze his fatty on the upstroke which I tried and he writhed.

After about another ten minutes, Josh then asked me to roll on my side and we awkwardly got ourselves in missionary position. His cocked pooped itself out (it literally exited my ass -- it was not tired) so I took the opportunity to position my ass at the end of the bed. As cliche as it sounds, my ass felt empty and I really wanted his cock back in there. With his feet on the floor and my legs on his shoulders, Josh entered me again and dove right in. He started a slow rhythm and kept speeding up until he was furiously pistoning in and out of my ass. He slowed down and sped up about 5 times and about :15 minutes. After that last rest he said he could not take it anymore and announced that he was ready to cum. Josh was more verbal than ever (which was hot) when I felt the first and second shot in my ass, but it was more like a trickle. Shot three was the jackpot -- with shots 5-7 almost as large and part of a 5 day load I later learned that he saved up for me. With his dick still in my ass, he grabbed my cock (which got super hard again when we moved to missionary) and started to stroke. There was no "edging" here -- he was going for my load. He leaned in like he was going to kiss me but started playing with my left nipple instead -- light touches at first, then a series of pinch, twist and release during which I had an orgasm that I could feel deep in my prostate all the through to its exit through my pisshole. This orgasm felt different than others due, I assume to the prostate simulation. I think I had those pleasurable, muscle spasm feelings of orgasm for about a full minute. Not as intense as my first time with Josh, but much longer and much more of a whole body orgasm. Still with his dick in me, Josh looked at me and said, "dude, you have no idea how much pleasure this is bringing me." My cock reinflated and said "thanks for the lesson and the boost of confidence, stud" I replied.

After a bit, Josh's small, tired cock plopped out of my ass followed by a combo of lube and sperm. I loved seeing his foreskin quickly cover up the head like it was going back in the garage. I had no idea so much sperm mixed with lube was up there.

A quick shower, then back home and to bed. Before I left I got a great hug and Josh said "I'm really honored to have your virginity, bud." It was said so sincerely that I actually teared up -- Holy Shit. Josh said "if your up for it, I'll teach you how to fuck me next." Of course, I could hardly wait.

No gym the next morning, but when I got up to take a shower, goo was still dripping from my hole.




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