The Art of Head

I was a virgin until a few weeks after my twenty-fifth birthday - mostly due to anxiety; that anxiety wasn't strictly isolated to penetrative sex - it also included oral sex.

Although I'd gotten a few blowjobs - some good, some bad - by the time I lost virginity, I hadn't given my first blowjob until a few months later. It wasn't that I hadn't wanted to do it, but I was worried that I wouldn't be good at it, that I would gag - or worse - throw up. Then there was the issue of my teeth; my canine teeth were long and came to sharp points, basically vampire teeth - the last thing I wanted to do while giving head was to draw blood. My friend Bree offered to teach me how to suck a dick, but she would have to show me on myself, and I wasn't entirely comfortable with that; besides, how could I learn what to do if I could actually see it? Sure, I could have felt the sensations. but that wasn't enough for me, I could have learned that from the blowjobs I'd already gotten, after all. Someone was already slandering my name on Grindr, telling guys that I was an acholic and addicted to xanax - neither of which was true - I did not want to get a reputation for giving bad head.

When my friends Chelsea and Charlotte visited me for my twenty-third birthday, Chelsea mentioned a book she'd read called Tickle His Pickle; I immediately bought a copy, but after perusing it, I was disappointed. I scoured the internet for tutorials but always came away feeling like the only way I'd really learn is to just do it; no amount of reading was going to give me the experience I needed to know whether I was going to be good at it or not.

A few months after I finally lost my virginity, I started talking to a guy named Julian on Grindr. He was very sweet and gentle, the sort of guy I could see myself falling for; he was overweight, but not incredibly so. We flirted for a while before we finally decided to meet up. There was no way that I could sneak him over to my place, and his roommate and I had beef, so the only place we could think of was the backseat of my car in the parking lot of my work.

I was driving my mom's old Lincoln Continental then, which had a spacious back seat. When he pulled up next to me, I got out of the front seat, and we both got into the back. The conversation was a little awkward at first - I'm always awkward around new people, even if I've talked to them online already, but thankfully Julian knew how to make me feel relaxed. I wasn't sure if he was boyfriend material, but I certainly enjoyed him as a friend and the benefits that he was about to bestow upon me.

Sex was out of the question - we were both - preferrably - tops - but that didn't mean that we couldn't do other things. Kissing Julian was nice - he had fresh breath, which I definitely appreciated - though I didn't feel much of anything when we kissed. I had never made out with a guy with facial hair before, but thankfully, Julian's moustache and beard were neatly trimmed and surprisingly caused no issue whatsoever. When he scootched down in the seat to suck my dick I sat there, grateful that my back windows were tinted - even though it was past midnight. The head was good, but not mind-blowing - mind-blowing head is still a rarity to me today. I was flattered when he allowed me to cum in his mouth and then swallowed. That was another thing I wasn't sure about; I knew that even if you didn't swallow the cum you could get an STD, but I felt that the chances were lower if I didn't allow it at all.

Julian blew me the first time we hung out and was okay with just getting a hand job in return. He understood my fears and reservations but said that he really wanted to see what my mouth could do. I told myself if we kept hanging out that I would probably try with him, after all, while not a micropenis, Julian's member was only about five inches - hard. I told myself that a smaller penis would be a great learning tool, literally and figuratively.

The next time we hung out, Julian had just finished sucking me off when he sat up and said, "Would you be willing to try sucking mine this time?"

"Oh...." I felt my heart plummet down to my stomach. I'd been hoping that he wouldn't ask for more than a hand job again. I wasn't sure when I would be comfortable giving oral, but I also knew it wasn't fair to keep expecting him to give it to me without getting it in return. I wanted to make him happy, but I was terrified of actually doing what would make him happy; he had driven twenty-five minutes to come see me again - in the middle of a snowstorm - didn't he deserve a blowjob?

"I know you're scared," he continued, his voice gentle, "but I think it would be hot if you tried. I promise you aren't going to be as bad as you think, it's really easy."

"I don't know..."

"You don't have to," Julian reiterated, ever the gentleman, "but I think you should at least try it. You'll never know until you do it."

He had a point. What was I waiting for? Wasn't it better to take the training wheels off so to speak with someone kind, someone I trusted? If I was terrible at head, Julian wasn't going to run around and tell everyone; he would try to help me get better, with no judgment or ill-will. Maybe I should just give it a try with him, I thought as my hand worked on his hard cock. He didn't smell like he didn't bathe - his hygeine was good - and I believed in my heart of hearts that Julian was the kind of guy that would be honest about any STDs he might have; he swore he was clean.

I could feel my heart hammering in my chest as I took his dick in my hand, and leaned down, wrapping my lips around it. My first thought was that I was grateful that his dick didn't have a taste. Because it was on the smaller side, it fit in my mouth with plenty of room to spare. I tightened my mouth around it, creating suction, and began moving up and down on the shaft. Julian moaned in delight as I wrapped my tongue around the shaft as well and flicked it on the underside of the head, something I had always assumed would feel great. His salty precum leaked onto my tongue as I continued to suck and lick, increasing my speed as his moans grew faster.

Within a matter of a minute or two, Julian tensed up and said, "I'm gonna cum!"

I quickly stopping sucking him and used my hand to finish him off. His hot, wet seed spurted out onto my hand, thick and creamy.

"How was it?" I asked, trying not to sound too desperate, too inexperienced, but I had to know.

"Really good!" he panted, licking his lips.

"Really?"

I couldn't quite believe my ears, but, then again, he had moaned a lot and finished a lot sooner than I ever had from head. Was it possible that I was actually good at something? That I'd been afraid for so long for no reason at all?

"You're a natural."

I couldn't help beaming with pride as Julian pulled his pajama pants up and cuddled up against me in the seat. It was the dead of winter and with the car off, we had to rely heavily on each other's body heat to stay warm. Julian asked me if I'd ever gotten a rimjob - I hadn't - but as spacious as my backseat was, it wasn't conducive to eating ass, not unless I was going to lean up into the front of the car and have him go at it. In the end, we ended up cuddling and kissing for an hour or so more before we decided to call it quits for the night.

Soon after that, Julian met a guy in Wisconsin named Brandon and they started dating; it didn't take long for Julian to move there. They're now married and seem to be happy; they have an open relationship, and although I've been invited to be part of it when they're in town visiting Julian's family, it hasn't happened yet.

Although he and I have mostly lost touch, I'll forever appreciate how kind and patient Julian was with me, and how honest he was when I finally did try sucking his dick. It's funny to me that I was afraid to do it for so long - now I enjoy giving head more than anything. I'd rather give head than have sex most of the time - there's no pressure, no stress. I know I'm good at it and I enjoy unravelling a guy with my mouth alone. Now that I'm experienced in the art of head, I cannot understand how people can be bad at it - it's so simple! I suspect it had more to do with not wanting to do it - especially all the time.

Now, in my mid-thirties, I've performed oral sex on more guys than I have slept with; I've blown at least half a dozen "straight" guys, most of them several times - and a few of them have become obsessed with me because of my oral skills. It's nice to know that I'm naturally skilled at something so vital to life as a gay man; there are a whole community of guys who actually prefer oral over penetrative sex, called sides - I think I've found my niche. I often joke about charging for oral but haven't quite gotten up the gumption to do it; I can't help but think that I could have a nice little side hustle going on if I could build up the courage to do it - and if it wasn't illegal, of course.