I'm almost 30 and I'm a virgin. When I first saw the movie "The 40-Year-Old Virgin" I was a little terrified because it had an air of prophecy about it. 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 ten 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 I couldn't keep it up and 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 just to 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, not to mention physical deformity are, I would have to imagine, major issues for anyone who 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
Off the top of my head...
Hire a sex worker. It'll allow you to separate your anxieties about finding a 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 with sex workers 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 allows. Even if you have to go alone, go. Even if the thing you want to do doesn't seem like it'll put you in front of many/any women, do that thing. 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, you'll feel less isolated and less alone. Even if you never meet someone (I'm not sugar-coating 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 as yours was, 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 patent, accepting, kind, and similarly willing.
Get over those scars. I had a boyfriend a long time ago—my first serious boyfriend—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 that 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 even 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 scarring that was so obvious to him and made him feel so self-conscious about his genitals? I didn't even notice it until he needlessly apologized to me for it. Genitals are a jumble of flesh and folds and hairs and colors and bits and pieces and 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.