My First Blowjob from a Male

This is a bit of cheating on my part - this includes two First Times - one in my youth and one as an adult. The first is so short that it did not make sense to have it as a separate story.

I actually had three sexualized encounters with friends when I was growing up. The first two I chalked up as normal exploration as neither lasted more than a few minutes and I don't really recall anything more than just mutual touching.

The one that had the biggest impact on me was a little later and unfolded differently.

I was friends with Bill and Dave - brothers who lived up the street from me. The three of us played together frequently, though Dave was a year or so younger than I was, and his younger brother Bill perhaps several years my junior.

One night we had pitched a small tent in their front yard and were 'camping' overnight in it. As an adult I cannot remember anything we did nor talked about that evening. What I do recall now is the three of us laying side by side on top of our sleeping bags. The summer night was warm and it would have been far too hot to sleep inside the bags.

Dave fell asleep before his younger brother and I did. We had turned off flashlights but a dim light remained inside the thin nylon tent, perhaps ambient moonlight or a porch light from the house.

I would love to know how the next part unfolded - if there was any whispered talk of sex -- or at least whatever passed for sex talk at that age of the woefully un- or even mis- informed.

What I do remember is that Bill had rolled over onto his left side to face me. I was laying on my back, with him to my right and his sleeping brother on my left. He lifted his leg as he faced me and placed it on my cock. I don't remember being shocked or worried about it, which makes me think there may have been some sexual banter prior to him rolling over. I have no idea if it was his idea or mine, but given my history and my personality, I strongly suspect he was the initiator.

I don't know if I was naked prior to his bare leg being placed on my dick, or if I removed my underwear afterwards, but however it unfolded, his inner thigh was resting atop my naked member and it felt amazing. It is the first time in my life that I can remember how good it felt to have someone else touch my penis - warm soft skin resting against it, the pressure from the weight of his leg, and simply having someone else interested in giving me pleasure.

Bill began making sort of a slow bicycling motion with his leg, such that it rolled my dick around against my body. That is how I remember it anyway, though I suspect it was likely more of a gentle back and forth, rolling my cock between his thigh and my stomach, rather than in some sort of circle. The sensations were exquisite and the first time in my young life that I had ever experienced dedicated, intentional, sexual pleasure.

I loved how it felt to be the target of his sensual pleasure giving - to have someone else showing that interest, taking the initiative to make my cock feel good. I also loved feeling his warm skin pressing down, sandwiching my dick between his leg and my own body. I wonder now as I reflect on the situation if he had ever done something similar? In retrospect it seems improbable that he would be able to naturally deliver such pleasure without some previous experience. Or perhaps he was simply doing to me what he wished someone would do for him? At the time I suspect I was thinking only of hoping that he wouldn't stop!

I'm not sure how long Bill rubbed against my cock with his leg, but what eventually stopped us was something sticky and wet. We knew it wasn't blood or urine but clueless otherwise. As you have undoubtedly already guessed, I had experienced my first orgasm ever, but at that time neither of us knew what it was. I don't remember feeling it as a release -- I think it sort of leaked out rather than shooting hard or locking up my body like it does now.

Now I wish there was a video of the event so that I could see for myself all the things I am curious about -- the conversation before hand, how long it lasted, and if I had gotten hard at his touch. I wonder how it ended -- if we had continued talking or drifted off to sleep.

I do not remember any awkwardness nor even mention of it after that night. I do remember that it was the event that began masturbation for me as I tried to recreate that wonderful feeling again. I have memories of laying on the floor in the bathroom at home during the winter, pressing my cock up against the forced hot air heat vent, using my hand to roll my dick back and forth across the warm metal like he had done with his leg against my body.

I don't know if I discovered orgasm right away or if it took some time, but I do remember experimenting to discover what gave me the best feelings - rubbing my penis with different materials, trying different levels of pressure, that sort of thing.

Some time after that initial camping adventure, I slept over at Bill's house again, this time indoors. I had brought my sleeping bag and asked to sleep on the floor in Bill's room instead of Dave's, hoping for some sort of repeat of our last sleepover.

I was a bit reserved and shy by nature, and especially when asking for something sexual, taboo, and where I was the receiver. As the lights went out I held my breath, listening intently for any movement from him, hoping to hear the sounds of him slipping out of bed. No such sound came from his side of the room so I tried noisily jerking myself in the sleeping bag to let him know I was interested but he was either asleep or not wanting to engage.

I don't remember exactly how I felt about those scenarios as I got older, I assume I was ashamed of them since it was during a time where being gay was not at all socially acceptable, and I grew up in a house where same sex relationships were considered morally wrong. Probably I chalked them up to being normal childhood experimentation and I don't remember being overly worried about it (other than the embarrassment or shame I might have felt with those I had played with). I definitely remember wanting to repeat the pleasure I felt in that tent, but don't remember specifically wanting it to be a guy. In other words, this may have been exactly what I feel today -- that the gender of the giver is not as important as the pleasure of it.

Fast forward to my late twenties. I was fresh out of the Army, on my first professional job in Cambridge. I had been married for 4 years and it was a nightmare of a marriage. She was controlling and non-sexual and I was completely miserable. I began reading personals online, trying to find a female friend with benefits. Unfortunately I could not find a woman who was interested in a married guy, much less one who wanted sex without any kind of relationship.

One day I found an online post where she described in glorious detail the kind of blowjob that I crave -- very slow and sensual, essentially cock worship. At the end of the long post "she" admitted to being a guy and that he was posting in that section of the personals to get the attention of straight men.

Over the next few weeks I kept thinking about that post, wondering what that would be like to receive something so awesome but from a guy. I was very conflicted about it because I was not at all attracted to guys and couldn't imagine what it would be like to have one sucking my dick. I worried that perhaps it was some sort of trap, where someone homophobic would attempt to blackmail me or even get violent. And yet it was also strangely exciting thinking about it. Not so strange from the perspective of receiving pleasure, but strange in that I seemed able to separate attraction from sexual pleasure, and that I could seriously consider allowing a male to give me a blowjob. I could easily chalk up childhood experiences to just experimentation and curiosity, but as an adult and fully understanding what I would be visiting for was a whole different story.

I finally worked up the courage to reply and we emailed back and forth for a bit, primarily me explaining what I was seeking. We set up a date and time for me to come to his house on a lunch break and I was a nervous wreck. When I showed up at his house I think my knees were actually shaking and my heart was in my throat. I was nervous about meeting someone for the first time, terrified this was some sort of scam, and not at all certain how things like this typically unfold.

Fortunately he was very welcoming, friendly, and easy to talk to. He was perhaps 30 years older than I, putting him in his late 50's with short graying hair. He was much shorter than I and of average build, putting me a little more at ease about potential violence. We chatted for a few minutes, covering all the standard small talk, and then he said something like "well, we both know why you are here, want to get started?"

I agreed and he led me into his cellar. In spite of his welcoming demeanor many thoughts flashed through my mind, imagining trying to explain to my wife how I was bruised if he attacked me or something. Nothing bad happened as he brought me to a small bedroom in the basement, bare except for a single low height bed. He suggested I strip down and get comfortable on the bed and he watched as I slipped my jeans and underwear off. I lay back on the bed, asking if that was where he wanted me. He told me to get comfortable in whatever position I wanted, and then lowered himself to the bed, positioning himself between my legs.

I wish I could explain everything he did for me, but those memories have been lost to time. What I do remember is how I felt. After several years in a house with an emotionally abusive wife and precious little sex, it was mind blowing to have someone of any gender taking such an intense interest in my cock and eagerly sucking it for me.

It was heaven having his mouth on me from a physical perspective too. He knew from our exchange of emails how I preferred being sucked in slow motion and he did a wonderful job of making love to my cock with his mouth. He had a knack for being able to apply a lot of pressure with his mouth and to this day I don't understand how he could keep that up for so long without his lower jaw falling off! To this day I have not had someone be able to close their mouth so tightly around my dick, and especially for such a long time. That first time in his bed he sucked me for nearly an hour before I came. I had no difficulty in getting nor staying hard for him with all that glorious sucking he was doing, but I was having a really tough time crossing the finish line. It certainly was not for lack of pleasure, but rather there was no mental stimulus to accompany it. It was strange feeling such sexual pleasure but having no visual stimulation from a female form, no chemistry or attraction, no thrill of being with the opposite sex. I closed my eyes and fantasized about a woman being between my legs instead and eventually was able to cum. That marked one of the few times someone sucking me swallowed my cum, and the first time someone had ever continued sucking me afterwards. I loved the tenderness of it, almost as if he was thanking me for my load. I was hooked!

I visited him a number of times after that, perhaps once a month or so for a year. I missed that visual stimulation and the attraction of being with a woman, but I absolutely loved the physical pleasure he delivered, and even more so I loved feeling like someone desired my cock -- something that I was desperately missing at home. His record was close to two hours sucking me and I truly thought he broke my dick! I wasn't able to get hard after that nor did I experience any of the normal sexual thoughts and fantasies for at least several hours afterwards - long enough for me to notice how unusual that was for me.