Q: I’m almost 30 and I’m a virgin. I’m an overweight, straight-ish guy (I’m attracted to a few men, but those cases are exceedingly rare). I’ve also gone through an absolute hell life thus far, losing a testicle to cancer and having an abusive father who threatened a teenage me into celibacy by invoking the phrase “penile lobotomy” should I have sex with any girlfriends. I’ve barely dated in 10 years, and while I’m free from my father and the aforementioned mortal dick terror, I’m also INCREDIBLY scared about putting myself out there. I’m disabled, I’m not conventionally attractive by most standards, my whole zone down there is scarred up from surgeries, and, to top it all off, I’m on the small side. The last time I had the opportunity for sex, I went for it, but I was so terrified that I couldn’t keep it up. The woman I was with said something to the effect of “Well, I can’t do anything with that, now can I?” after which I asked her to leave because, seriously, that’s kind of an asshole thing to say. I’m notionally on Tinder and Bumble, but I really don’t know what I’m doing—and more often than not, I feel like the right thing for any theoretical partners would be for me to just stay in hiding and not inflict my grotesque presence on them. I’m scared of another humiliation, as that’s most definitely not my kink, and I’m at an age where my complete lack of experience and physical deformity are (I would have to imagine) major issues for anyone I might encounter. I truly want romance, sexuality, and companionship in my life. I haven’t fought through poverty, disability, physical and emotional abuse, and my genitalia trying to kill me to stay entombed in my office alone and unloved. I just do not know where to even begin. — The Virgin Who’s Been Fucked A Whole Lot Just Never In The Good Way
A: Off the top of my head… Hire a sex worker. It will allow you to separate your anxieties about finding romance and companionship from your anxieties about being sexually inexperienced. A kind, indulgent, competent sex worker can relieve you of your virginity and help restore—or instill—confidence in your dick’s ability to get and stay hard in the presence of another human being. Be totally honest about your inexperience and your concerns. If you get the sense during negotiations—which should be brief and to the point—that the woman you’re talking to is impatient or uncaring, thank her for her time and start over. There are kind, caring, compassionate sex workers out there. Presumably you’ve got a computer in your office, TVWBFAWLJNITGW. Use it to find one.
Get out of the house. Go places, do things—as much as your disability and budget allow. Even if you have to go alone, go. Even if the things you want to do are unlikely to put you in front of many/any women, do those things. You’re likelier to meet someone if you’re out of the house and moving through the world. Even if you don’t meet someone right away, you’ll feel less isolated and less alone. Even if you never meet someone (I’m not sugarcoating things—some people don’t), going places and doing things means you’ll have a rich and full and active life regardless.
You’re not alone. Okay, you’re alone—but you’re not alone alone. Meaning, there are women (and men) out there who feel just as paralyzed as you do—because they’re 30-year-old-or-older virgins, because they’re not conventionally attractive, because their first/only sexual experiences were just as humiliating, because they had traumatic childhoods and bear emotional scars. You want a woman to come into your life who is patient and accepting and kind and willing to look past your disability and your inexperience and your difficult history. Be patient, accepting, kind, and similarly willing.
Get over those scars. I had a boyfriend a long time ago who had significant scarring on his balls and taint. He was a farm boy (sigh), and he fell on a piece of farm machinery and wound up straddling a scalding-hot pipe. I don’t know how that worked exactly, because I don’t know from farm machinery, but the pipe burned through his jeans and left third-degree burns on his balls, taint, and upper-upper thigh. Ten years later, we started going out—and guess what? I didn’t notice his scars. And not for want of opportunity: He was my first serious boyfriend, and I spent the better part of three months with my face in his crotch. The scars that were so obvious to him and left him feeling self-conscious about his genitals? They were invisible to me until he needlessly apologized for them. Genitals are a jumble of flesh and folds and hairs and colors and bits and pieces and sometimes scars, TVWBFAWLJNITGW. If you’re worried your scarring is noticeable, mention that you’re a cancer survivor and lost a ball but gained a sick (as in cool) scar.
Good luck, TVWBFAWLJNITGW. We’re rooting for you.
Q: I’m a straight woman, and I’ve been dating my boyfriend for about eight months. We have a wonderful relationship and amazing sex. There’s one thing he does in the bedroom, however, that I find off-putting and I was hoping you might be able to provide some insight. About 25 percent of the time after he ejaculates, he briefly licks some of his come off his fingers. This kind of creeps me out. I’ve been with more than a few dudes, so I obviously understand that a woman eating their come is a common turn-on, but this is my first experience with this particular incarnation. At first I was worried my aversion might be rooted in some deeply buried homophobic beliefs, but we’ve discussed the idea of me pegging him, and that I can get behind. I think it’s more that this smacks of a certain egotism I find frivolous. Like, I wouldn’t go around shoving my fingers inside my pussy and rubbing the results all over my face. Typically we’re able to discuss any kind of conflict or confusion that arises between us, but this one seems tough to broach for me. Three questions: How common is this? Do I need to just get over it or should I try to talk to him about it? Would most guys suck their own dick if they were able? — Yearning Understanding Concerning Kink
A: 1) It’s not common, YUCK, but it’s not unheard of, either. Maybe your boyfriend grew up with sex-phobic parents who blew up at the sight of a crusty sock—so he opted to destroy the evidence by eating it and developed a taste for it. Maybe he thinks his semen contains powerful woo-hoo-y masculine energy and wishes to retain some of it. Maybe he had a girlfriend who thought it was hot to see him eat his come and he (wrongly) assumes it’s a turn-on for you, too.
2) Yes, you need to get over it and, yes, you should ask him about it. The former almost certainly requires the latter.
3) Every man on earth tries, a select few succeed, and we all would if we could. Even my new friend WORM.
