Losing It

John Orcutt

I’m lying on my stomach on the bed with a pillow tucked under my chin. He’s slowly parting my asscheeks and very slowly, very gently lapping at my tight hole. I moan just a little bit. “You like that?” he asks. I nod vigorously and he licks one of his fingers and presses it against the opening until I give way. He slowly fucks me with the one finger and then he spits on a second and pushes them both against my ass. “A good lover will take his time to make you feel comfortable, work up to it,” he instructs. “How does this make you feel?” Just like a therapist. OK, yeah, I’m in bed with my therapist. It’s a long story.

Considering how amazingly rounded my heels are from circling the block for the better part of two decades, I am still what is commonly referred to as vanilla. I try not to couple with anyone who requires paraphernalia or special outfits in order to have sex. I have never understood the lure of leather and am still waiting for the gay community to eroticize cotton. Like most people I have very specific things I like to do, and don’t like to do, sexually. I don’t like to go home with people. Quick and uncomplicated has been a formula that’s worked for me for years. “Do ’em where you find ’em” is my motto. I also hate talkers. Chatter during sex should only consist of directions, updates, and forecasts. I am not your boy and, at a boyish 35, I am certainly not your daddy. Say “daddy” in any context and images of my father mowing the lawn appear instantly, dooming any mood approaching horny. Preferences? I had a tonsillectomy as an adult, which I like to think of as the only gay cosmetic surgery I’ll ever need.

Despite these limitations, I do get plenty of action. I’m a standard 5 foot 11 inches, I have jet black hair and the kind of ice blue eyes one generally finds on Alaskan huskies pulling sleds. I don’t have a gym body but swim and practice yoga on a regular basis. I guess I’m just not that good at fantasy play and role-playing and verbalizing. How many times have I been perfectly happy down on my knees sucking off some hottie when he insists, “You want that dick, doncha,” pulling it out of my mouth and slapping me across the face with it and actually expecting an answer to his ill-timed and highly rhetorical query? “Yes, I want it. That’s why I just sat in a smoky, dark bar through four beers, half a pack of cigarettes, and your boring life story, so that I could wrap my lips around your big fatty despite the fact that I’m going to have to walk home at sunrise while it’s raining out. However, now that you’re caning me with it I’m a little less enthusiastic.”

Despite years of frequenting video booths, parks, sex clubs, bathhouses, warehouse districts, backrooms, and the apartments of numerous strangers, I’m still a virgin. No, it’s true. In the strictest sense of the term I am a virgin. Please keep it under your hat as it could obviously ruin my standing in many social circles. It really is amazing that an attractive, sexually active gay man in his thirties can say this. Even the butchest top men have been fucked at least once.

Why? I’m not sure. Maybe I’m saving it. Maybe it has never truly appealed to me. Maybe I’ve got some sort of hang-up. But it seems like something I should know how to do in a pinch. It’s like working for the AAA and not knowing how to change a tire. I think I figured that when Mr. Right came along, I’d bite the bullet (and pillow) and learn to love being sodomized. However, after hundreds of Mr. Right Nows, Mr. Wrongs, and Mr. What-the-Fucks, I started sizing up my friends like women assessing potential sperm donors. I had chosen a handful of potential candidates on whom to bestow the honor of busting my cherry if I still had it by the age of thirty.

That was half a decade ago. It’s cute and somewhat flirty when you’re a teen or in your twenties to let your curious date know you’ve never been fucked. When you’re thirty-five and you’ve been sexually active for nineteen years, it’s downright creepy. It’s not that I haven’t gotten any offers. I got a lot. And a lot more once they discovered it was untrodden territory, which is why I started to act like a stone-cold top, when I’m not. In fact, I’m the most passive top in the universe. It takes an extremely bossy bottom to launch me into action. Generally, I only fuck tricks when they are screamers. It is the equivalent of stuffing a sock in their mouth. Also, I’m uncut, and I think safe sex is important, and, well...perhaps other uncut guys will understand, but it’s kinda of like trying to put on pantyhose over a pantsuit—just not that comfortable.

So, until this year when asked, “Do you get fucked?” I always said, “No” in such a way that my trick du jour knew it was nonnegotiable. They never pursued the subject.

Rich didn’t do that. On our very first date, six months ago, when he asked if I ever had been, I had to answer honestly. He didn’t seem to care why, and I think he saw a challenge—and I saw salvation from my ass becoming the Miss Havisham of the gay world. Because he used to be a whore (opposites do attract—I’ve always given it away free), I figured he was a trained professional and would be the perfect candidate.

My first task was, of course, to get ready. I’m a regular Girl Scout when it comes to a project. I am also the kind of person who has to clean the entire house before anyone visits. Here’s a question Dear Abby doesn’t get that often: Is it less shaming to buy one personal hygiene item but make several such trips than to buy a whole lot of personal hygiene items at once? I was asking myself this as I sized up the aloof staff at my local drugstore. I was trying to determine the fastest, most unobservant clerk and whether I wanted to save ten cents on a generic brand versus the tried and true. Sidling up to the checkout carrying a half dozen enemas with a line of people behind you including two of New York’s finest is embarrassing. Finding yourself on your elbows with your face pressed against your (very clean) cold tile bathroom floor staring at the underside of your toilet while squeezing a small plastic bottle filled with god-knows-what into your ass like the little man on the box is mortifying.

Assuming everything needed to be clean and trouble free inside and out, I tried to sandwich my butt waxing somewhere among a manicure, a pedicure, and a haircut. If you’re wondering what butt waxing feels like, don’t ask your straight female friends. However, when they tell you to go to a Russian lady, listen to them. Svetlana was a dear. I assumed this would occur on all fours, but she kept me lying face down and the pain was minimal—I mean, I’m not Sasquatch. There was a tricky moment when she asked, “You vant zee eenside, too?” “Ah, um, yeah,” I mumbled, as if the idea had never occurred to me. “Vell, I veell need you to help me,” she instructed. The image of me prone pulling my ass cheeks apart with both hands while a large (yet gentle) Russian women holding a pot of hot wax pulls strips of hair off my ass is not one I’ll soon forget.

These weren’t the only problems. Rich’s was not what one would consider a “starter dick.” If it were a mobile home it would easily be a double-wide. I decided to have several dates with what the package referred to as “The Love Club,” chosen for its tapered effect, allowing one to, well, loosen up, a bit at a time. After all this preparation, both mental and physical, you can imagine how I felt when Rich spit on the head of his dick and rammed it against my lubeless ass. “How’d everything go?” asked my informed and expectant roommates later, much like a group of Third World women waiting for me to produce the bloodied sheet. “Fine,” I answered. “He said, ‘Am I hurting you?’ and I said, ‘duh’ and smacked him.”

After several such failed attempts, Rich dumped me. I can only assume it was because my asshole didn’t slam open after one glass of wine and a Johnny Mathis album. Though my virginity was still intact, my interest in keeping so no longer was. I decided my problem was in my head, and, like any college graduate, I decided to seek therapy. My first therapist, an elderly, myopic Jewish man in a badly frayed cardigan, insisted this was due to my father grabbing me by the scruff of the neck and kicking me in the ass when I was a child. It turns out that my ass will open like “a flower in the springtime” once my father passes away. After using my eighty-eight-year-old living grandfather as a standard, and some quick math, I decided I didn’t want my asshole blooming when I was in my sixties. My second therapist, an environmentally ill lesbian who insisted that I not wear deodorant, concluded I was not just a control queen but the ultimate control queen. Who else could maintain such a “hypervigilance over the barbarians crashing my gates for so long”? My third therapist, a straight woman who had never been told that home perms are never an answer and needed the term “rimming” defined, determined that I was an overprotective mother and my ass was my child, and that I didn’t want to expose it to the harsh realities of life.

Shortly after my final session, my roommate and I were meandering through the meat-packing district on our way to a party. We overheard a shlumpy businessman on his cell phone explaining, “She’s a therapist...a sex surrogate,” to some befuddled friend or family member. Trust me when I tell you that finding a hot gay sex therapist who will actually fuck you isn’t that easy. It took a lot of talking to people and much trial and error. This is like my eighth session with him—the first five were all talk and no play. The sixth was all show and no touch, and the last session was pretty much foreplay and chat about the fact that this one would be the big fuck.

Roger, the therapist, is thin and tight with ropy muscles. His hair is brown and a little too long with a sprinkle of gray here and there. He seemed like a good therapist, but I wasn’t sure he’d be a good lover. After the fifth session where I finally saw him naked, I didn’t really care. He has one of those cocks that inspire porn directors. It’s proportionally too thick for his thin frame, with two veins on either side that run up and down from base to head like the Yangtze and the Volta. When he gets really excited the head turns a dark purple as if it’s going to explode. His balls are chunky and hang low as if he had his ball sac professionally stretched to just the right length. Hair-wise, he has a light sprinkling around his nipples and on his ass and balls, and that perfect V from his navel to his pubic hair.

That’s why I’m lying face down getting ready to give it the old college try while Roger lubes up his third finger. I realize that there really isn’t any reason for me to remain a virgin. I’m not saving myself for anyone in particular, as if there were anyone in particular. I actually am not here anymore to lose my cherry. I’m here because I want Roger to fuck me. I want his fat, veiny cock inside me. He’s fucking me with three fingers and I’m rocking like a crazed three-year-old on a hobby-horse. Jesus, I’m so glad that I’m here and I’m going to get fucked. I want him to ram it in me. I feel him start to place the head against my ass.

“Yeah, stick it in me,” I say.

I can’t believe I’m not only saying it, but meaning it. I want Roger to split me right in two with his donger. I want him to tear me open. I want to sit and spin on that thing Thai style. They could lower me in a basket from the ceiling so that my asshole could swallow his cock whole, and then I’ll pound against his pubic bone until he’s black and blue.

“Yeah, fuck me. Fuck me hard!” I scream.

“I’m afraid our time is up for this week.”