Q Here’s my problem: I love women. I love the way they look, I love the way they move, I love the way they sound. I like to see them naked. But the idea of actually interacting with women—trying to engage them in intelligent conversation without coming off as absolutely leotarded—absolutely fucking terrifies me. I’m a virgin at 30. I’ve never had a girlfriend. I’ve never been on a date. I’ve never even had a conversation with a woman that lasted longer than a couple of minutes and wasn’t completely superficial and forced.
First piece: Get your ass to a shrink—maybe a lady shrink—who can help you with your near-crippling social anxiety and maybe toss some meds your way.
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Second piece: Hire a fucking sex worker, AAA, just don’t fuck her. Paid companionship is not a crime—there’s nothing illegal about paying an escort to escort you places. Find a nice woman, pay her for an hour or two of her time, and have a nice, polite conversation. If you like her, make another appointment and have another conversation. Cops—asshole or otherwise—only bust men when they offer money in exchange for sex, AAA, so don’t offer money for sex or accept her offer to have sex for money and you won’t get busted. And cops working undercover to bust johns don’t make follow-up appointments or build ongoing relationships with clients. So if a woman sees you more than once—or twice, to be extra safe—she’s not a cop.
It ends up that he likes to be dominated, spanked, and butt fucked—and to cross-dress. Our sexual encounters are a bit different for me, to say the least, but I thoroughly enjoy them. I like spanking him, humiliating him, tying him up, and watching him try on panties (in which he looks darn good!). It’s all rather exciting!
- Do you find it weird to be turned on by getting fondled and aroused into having sex while sleeping? I have a hard time communicating to partners that I want this! Can you give communication assistance so I don’t sound so freaky? —Freak in Phoenix
If you and your middle-school friends don’t believe me, CTOAATSOP, here’s what you should do: Go get a couple jars of creamy peanut butter or a few tubs of premade chocolate frosting. Refrigerate until firm. Get your dicks hard. Fuck your jars of peanut butter or tubs of premade frosting. Fuck them hard. Fuck them like they’ve been bad. Fuck them like you’re never gonna recycle ’em. Then go take a piss. You will not produce a peanut butter or chocolate frosting noodle, I promise you.
But I cannot tell a lie. While enclosing a nude pic—good nude, bad nude, boy nude, girl nude—can get my attention, it won’t automatically get a letter into the column, 509. Letters with naked pics arrive in my in-box every day. I could run nothing but letters from readers who were kind and/or cruel enough to enclose pics of themselves, their partners, their welts, their rashes, etc, week in, week out, 52 weeks a year. And the letter from the guy in his early 30s who lost his virginity that appeared in last week’s column—the dude who enclosed pics—was the first letter from a pic encloser that I’ve used in ages.
