From Jilling to Jacking

Bruce always knew he was gay. “I don’t want to downplay the difficulties of growing up gay today, but it really was harder back then,” he says. Following a marriage he describes as “really, mostly happy despite the situation” and raising two kids, he at last became the man he always was, decades too late.

“Masturbation wasn’t just important, it was more or less my entire sex life,” he says candidly, “save one or two anonymous extramarital one-nighters that caused me more grief and guilt than the thrill and joy of being a gay man for a couple of hours was even worth.”

Early on, however, Bruce discovered he could really spice things up by adding anal penetration to his routine. “I was thinking about it all the time, anyway, so it came naturally to me. I became quite a contortionist early on, using my fingers with a bit of Vaseline to help while I was drilling for oil up front, so to speak.” He laughs at his own silliness. “I moved to inserting objects, and eventually to the purpose-built hardware—which was by far the safest and most satisfying—but it took me a long time because I was terrified my stash would be discovered.”

“I was probably 12 or 13 when I discovered that rubbing the hell out of my cock could bring me to the ecstasy of orgasm, which was purely instinctual,” says Florentino, 40. “I had no clue why I needed to rub my dick, I just had to.”

Florentino, recently divorced, grew up enjoying masturbation, but feeling guilty and dirty about it. “I was mired with shame over my sexuality, both self-exploratory and partner-related, until my mid-20s,” he chuckles. “Oh, Catholicism!”

Currently partnerless, Florentino reports self-exploration is both on the rise and very satisfying. And he’s no stranger to knocking on his own back door. “I used to use an anal vibrator with great pleasure!” he says enthusiastically. “It made orgasms super-intense.” Florentino back-burned his pleasure while married, but now that he’s on his own, the flame has been rekindled. If trends continue, the vibe could be making a comeback.

Hunter is 35, happily married and reports a satisfying sex life. The only child of divorced parents, he was afforded a leg-up toward healthy sexuality from an open-minded mom. “I started reading Playboy—yes, actually reading it—in ninth grade. I honestly think my mom got me the subscription because she thought the magazine could stand in for my dad when it came to ‘the discussion,’” he laughs. “As a result, I knew about clits and G-spots and erogenous zones at 14.”

Not the worst trade-off.

“Having regular sex with a partner certainly makes my self-exploration less frequent,” he says, “but not non-existent.” It’s not regular, he reports, but rather prompted by inspiration. As for visual aids, he keeps a few magazines at the ready. “Internet porn is always quick and easy, or sometimes I’ll use erotic pictures of my wife that I’ve accumulated over the years. Otherwise, I’ll hit the shower and it’ll be all imagination.”

Toys, he says, play a role as well. “I tried a fake vagina sleeve once. It felt pretty good, but it was a hassle to deal with afterward. I still, on occasion, use an anal toy. It adds some intensity—it’s just a different dimension to the entire experience.”

Hunter laments—lightheartedly—that his pubescent sexual awakening lacked the compulsory, clichéd wet dreams so many boys endure. Perhaps that’s what led him to the showers at his college swimming pool where, for lack of a better term, he invented the hit-and-run sport of adventure whacking. “It was an open shower room, probably eight or 10 showers and totally exposed at both ends,” he says. “I was the only one there, but if somebody had walked in from the pool or the main building, I would have had to do some quick maneuvering not to be discovered.”

What prompted such behavior?

“I did it for the thrill. Totally.”

Ross, 18, and headed to a state school on a baseball scholarship in the fall, is one of those dream kids you might remember from high school: star athlete, the homecoming king—and he still dates the prettiest cheerleader.

“We were each other’s firsts this year,” he says. “Before that, it was just me and…[wiggling his fingers]…you know.” He laughs. “You see all this stuff in the movies about how the popular jock is getting all the girls—and I guess that might be a little true—but [girls are] actually giving it up less than you think. Or else I was in a prudey high school.”

He admits to regularly waxing his own surfboard “a lot, probably every day—or close to it—since I was 12 or 13. And still, even now that I am actually having sex.” The confession comes easily—with little-to-no-embarrassment. I can’t imagine my male peers in the John Hughes high school era giving up the ghost so easily.

So how does an 18-year-old find P-spot enlightenment? “It was an article I read while waiting at Supercuts,” he laughs. “My mom was sitting right next to me. I moved so she wouldn’t see it. It had a whole diagram of a guy’s ass, balls—like a science book.”

Ross’ experimentation started digitally—both kinds. “I tried touching it while I jerked off, but I couldn’t really reach,” he laughs. Undaunted, he went online to investigate. “At first, I was sort of turned off. I’m not gay, but most of the pictures were on gay sites. I have no problem with [homosexuality] but seeing two guys together… I don’t care who does it, but I don’t need to see it,” he laughs.

But that’s where he got the idea to use a toy. “There was no way I was buying one. I was too young at the time anyway, but I was also too much of a chicken-shit. I still am.” He stole a taper candle from his mother’s china closet instead. “I had nightmares it was going to break and I’d have to call an ambulance.” But he tried it anyway. “And now I pretty much use something every time,” he says, though he’s since moved on to small, pliable vegetables. “Why come when you can come?”

For his part, Bruce says butt play is moving into the realm of the mainstream with a vengeance, and thinks all men deserve to up their orgasm ante. “I could easily teach a Learning Annex course on summoning the old genie,” he says. “And lesson two—right after ‘Find your dick and grab it’—would be a nice, friendly introduction to Mr. Prostate.”

He laughs, imagining the outpouring of gratitude. “My office would be overflowing with dildo bouquets.”