Title: My first male Sexual Encounter in 40 years


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  • My first male Sexual Encounter in 40 years
  • Published: Apr 7, 2008
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  • Category: Gay erotic stories
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About: "I have masturbated all through my life but now jacking off was a regular almost daily occurrence"
About 3 months ago I was on the phone to my friend Bob. We're both in our early sixties and our families have been friends for almost 30 years. During the call I mentioned that my wife was going to stay with her family for a few days. Bob suggested that he might visit for a few days and bring some wine down. His wife couldn't make it because she was still working at that stage.

On the arranged day I picked Bob up at the train station and we did some shopping before heading back to my place. We spent the rest of the afternoon preparing the evening BBQ and catching up on news.

At around 7pm we did the BBQ thing and opened a couple of beautiful red wines. It was terrific, good food, good wine and a good friend for company.

We cleaned up after dinner and retired to the family room. I put some music on and we relaxed whilst finishing our second bottle of wine. Our conversation chopped and changed (as it does after 2 bottles of wine) and later in the evening the subject turned to our sex lives. I'd suspected for a while, but now had it confirmed that Bob's sex life at home, like mine, was virtually nonexistent. I was amazed we were even discussing this because it's not the sort of thing we'd talked about before except for the occasional joke. I put it down to the relaxing effect of the music and wine.

I wondered how he managed without sex. I handled it (pardon the pun) by regular masturbation. I have masturbated all through my life but now jacking-off was a regular, almost daily occurrence. I loved it. It must have been that my inhibitions were dulled by the alcohol because I told him openly that "If it wasn't for masturbation I'd go crazy". I had no idea how he would respond to this because he's a conservative type and we'd never discussed anything like this before. Bob smiled and I asked "do you masturbate" He nodded in agreement. I was amazed; the fact that the discussion had gone this far began to get me aroused and I began to feel my penis hardening. Light heartedly, I placed my hand on my now almost erect penis and gave it a bit of a rub through my shorts saying "talking about this is making me very horny Bob".

Now here was the moment of truth. The fact that our friendship could have disintegrated by persuing this now was overridden by my growing excitement. I turned to him and asked "would you mind if I masturbated now" He replied "Here... now" I replied "Why not" He said "I guess If you want to".

I got up and grabbed a box of tissues from the kitchen bench, before returning to the sofa and pulling my shorts and undies down. My cock was as hard as it's ever been and pre-cum was already starting to bead at the eye. I slowly started to rub my cock up and down. The sexual tension was so great at this point I knew I wasn't going to last long so I began squeezing the pre-cum from the eye of my cock and massaging it over the head. Then it began, waves of orgasmic pleasure engulfed me and with the first contraction I ejaculated a huge wad of semen onto my upper chest. My head was spinning as the second, third, fourth and fifth spurts of semen landed on my tummy. It was one of the most intense orgasm's I'd experienced in ages because at 62 years of age my orgasms are usually more ooze than squirt.

After wiping up I looked over at Bob and I could see he was both amazed and extremely aroused. His erection was clearly visible under his shorts so I reached over and placed my hand on his cock and squeezed it through his shorts. Bob put his head back and closed his eyes while I slid his shorts and undies down. I took hold of his penis and began gently rubbing it. His cock was longer than mine by at least an inch but not as thick. I'd guess it was about 6" long and god it was hard. I started to rub the pre-cum over the head of his cock as he sat there with his eyes closed. I circled the base of the head of his cock with my fingers until I saw his stomach muscles tensing indicating he was about to cum. With a huge moan his body stiffened and his hard cock began pulsing in my hand. Almost immediately his semen started spurting everywhere. It was beautiful to watch as stream after stream of cum leapt from the hole in the end of his dick. This truly was a magic moment for me because I find the male ejaculation to be one of the most beautiful sights on earth. I have spent hours on the web jacking off to videos of men and women masturbating. Also the knowledge that I hadn't had this kind of encounter since my late teens added to the thrill.

I asked "How was that" and he replied "Good" but I sensed he was embarrassed about what had happened. We began to discuss the experience and after a few minutes of uneasiness we agreed that if both partners enjoyed it, it was OK. After more chit chat and music I suggested we call it a day and hit the sack. I really didn't want it all to end there so as soon as he got into the shower, I slipped my clothes off and stepped in with him. At first he was surprised but once we began washing and fondling each other he relaxed and we caressed each other's cock to erection once more. We could have easily masturbated again there and then but I suggested we dry off and hop into bed.

Bob was at first hesitant about sleeping in my bed that night but I jokingly suggested it would save all the extra work of making up the bed in the spare room. Once into bed we resumed stroking each other's cocks until we were erect once more. While Bob kept caressing my cock and balls I worked my way down and placed my lips over the head of his cock. After a minute or so of tickling his cock head with my tongue I slowly I took the length of his penis into my mouth. I could taste the saltiness of his pre-cum and I began to gently move up and down his penis with my teeth just lightly touching it. After a few minutes I returned to the head of his cock and worked away with my tongue at his frenulum which is the Y shaped web of skin that connects the foreskin to the underside of the head of the penis. Pretty soon Bob began the short breaths and pelvic contractions indicating his orgasm was imminent. Then he moaned very loudly and I felt his penis pulse as he began shooting stream after stream of semen into my mouth. I couldn't believe I was doing this. The excitement of having a man's penis in my mouth was just too much for me and I couldn't hold back. The orgasm was on me in seconds and I began ejaculating as waves of pure pleasure engulfed me. After cleaning up once more we drifted off to sleep.

Very early the next morning, whilst still half asleep, I felt Bob move over and reach for my cock. This was unbelievable... I rolled onto my back to give him better access and he went down on me sucking my cock to erection. He must have sucked me for half an hour and I thought that I wasn't going to be able to cum so I suggested we try something different. He agreed so I got some Aloe Vera from the en-suite and covered the head of my cock with it. I asked him to roll over and I placed my penis at his ass and slowly began pushing it in. My cock went in fairly easily being small and I began to slowly pump his ass. My wife and I had had anal sex on occasions when we were first married and even though she didn't enjoy it, I remember it being much tighter than any vagina. It seemed like a matter of seconds when the total sensuality of the moment overcame me and once more I went into an unbelievably powerful orgasm ejaculating what seemed pints of semen into him. I rolled over and let Bob return the favour and whilst it was uncomfortable at first, I soon began to enjoy the thrusting deep inside me and the contractions and pulsing of his cock as he enjoyed a huge orgasm.

Needless to say the next 3 days were spent enjoying each other in a variety of ways and whilst it hasn't affected our friendship, I'm sad to say that when leaving to return home, Bob said that he didn't want to repeat the episode. I was very disappointed to say the least. We'll see!

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