How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to email@example.com. Nothing’s too small (or big).
Dear How to Do It,
I’m a 39-year-old woman. When I was 20, I met my first very well-endowed man, who in a way “trained” me to take a large penis. Since then, I’ve been in two monogamous long-term relationships, both with average-size men. I hate to admit this, but I left both those relationships because the length just didn’t cut it for me. I needed more. I’m great at taking it, and it’s the most satisfying way for me to come. Currently I’m involved with two partners who more than measure up, but I don’t see either of them too often, and I’m still out there dating. My question is, how do I put it out there in the online dating world that anything less than a hard 8 inches will only disappoint me? I’ve tried stating in my bio things like “bigger is better,” but ended up with delusional men who were even less than average. (Cue awkward encounters.) I don’t want to come across as too slutty or overexperienced—I’m really quite reserved—so asking straight off “Hey, how big is your dick?” seems a bit off-putting. Any suggestions to help a girl out?
There is no foolproof way of ensuring the dick that is ordered will be the dick that is delivered. For, sure as people have penises, they’re going to lie about them. Give them an inch, and they’ll add two to what they claim they’re packing. If I’m being generous, maybe 50 percent of the dicks I’ve seen in person have matched their owner’s description of them via apps (as I’m sure you well know by now, you cannot rely on a dick pic without some other object to show scale). The rest have been smaller. I’m not such a size queen, so this hasn’t caused any major problems. I’ve never abandoned a hookup over it (and I have shut down sex in the middle of it for a range of reasons), but letting bad behavior pass—especially bad behavior that is predicated on the assumption that I will be polite enough to let it pass—gnaws at me. Guys who exaggerate their size by more than an inch in advance of meeting are small-time scammers, and I hate their deception as much as I respect their hustle.
There are some sites that purport to be devoted to matching hung kings with their size queens, but you don’t hear a lot about them these days, and some reviews I’ve read paint them as teeming with liars as well. I’m not going to refer you to something that I have no experience with and seems otherwise dodgy as hell, but you could Google and see. Another option is to cruise Reddit’s big-dick subreddits, like this one (NSFW, obviously), since there are guys on there who will note that they’re specifically looking for encounters with women. They have galleries of their giant dongs, and while I wouldn’t put it past some people to concoct whole personas using stolen dick pics, that’s a lot of work and hopefully not too common. The downside is you may have to do a lot of searching to find one in your area. May be too big a project for a big dick. The online community of LPSG has similar patrons and a whole forum devoted to personal ads to boot. You could also try Doublelist, the site that aims to replace Craigslist’s personals section.
Those options will allow you to ask for what you want while remaining as discreet as you see fit—you need only to post text, not a pic or full profile. Of course, you may still run into the smalltime scammers that vex and impress me; you can ask dudes to take fresh dick pics with an item of your choice in the frame (a tube of Chapstick, a quarter, a small note that you’ve dictated) to help ensure veracity. I want to also encourage you to continue to openly fish for big dick via your profiles. Why not ask guys if they’ve got what you want? If it’s off-putting, great. You’re filtering out the dick not up to your standards from the jump. Saves everyone time. I believe there’s nothing wrong with coming across as slutty or overexperienced, and anybody cool and/or hung will respect you as a woman who knows what she wants. Be proud of that.
Dear How to Do It,
I am a straight, mid-30s, happily married man with an amazing wife and a young toddler. My wife and I have been together for a little over eight years. Our sex life started out a little slow, worked up to a good pace, then dropped back down after we had our child. We probably average sexual intimacy once (at most twice) per month. I’m fine with taking care of myself the rest of the time and, as far as I know, my wife doesn’t need to take care of herself very often (just not that into it). We’ve had discussions about having more sex, and we always agree that it should happen more often. However, when I try to initiate, I’m fairly often turned away because “It’s too late” (at night) or “I’m tired” or “I’m not in the mood” (during the day). Needless to say, I get a little pent-up.
As a part of exploring options, I recently went to a full-nude strip club. I wanted to just see something different and get a different type of horny. I paid for a lap dance then left. I did not tell my wife about it. I generally feel no regret for going. I got what I needed and left. However, I now know that this particular experience will satisfy my needs (when I feel them). And I know I will want to go back. My concern is making this a habit and continuing to hide it from my wife. I have no feelings for the strippers—they’re just someone different to look at naked. But I feel that this would (in most circumstances) be considered cheating.
Obviously, there is no sex and no physical touching outside of the occasional skin rub from a lap dance. But, again, I’m looking at naked women who aren’t my wife. I’m stuck on how to proceed. Should I just kick out the thought of ever returning to the club? Should I tell my (I’m sure to be) wholly disapproving wife? Should I continue to go and risk my wife finding out? Any input would be greatly appreciated.
—Look, Don’t Touch
I love that you went to a full-nude strip club to “see something different.” You’re referring to the interior decorating, I’m assuming. I’m sure it was fabulous. In my understanding, mostly via Showgirls, lap dances are for getting off: The dancer rubs on you, you come in your pants. That’s not nothing, and if it exists in a gray area between cheating and not cheating on your wife, that’s because you’re keeping it planted there by not discussing it. Right now, you’re not cheating on a technicality, and just barely—you said you’re “sure” your wife will disapprove. (If you aren’t ejaculating during lap dances, well, I think they still count as falling left of faithful unless explicitly discussed.)
Yes, you should talk to your wife about this. It may very well be a good fix for both of you, but it’s just not cool to be doing sexual things behind her back unless she specifically consents to a don’t-ask-don’t-tell arrangement. You stated your case rather reasonably in your opening paragraph; convey this to her with reassurance and compassion. You need release! You’ve got to come! You’ve discovered something that you can be close to absolutely certain will not interfere with your relationship. It could occupy the space of a hobby in your schedule. You owe it to this amazing woman to be amazing back, and keeping secrets with semen running down your leg is not really an amazing way to be.
Dear How to Do It,
I’m a woman who met a man a few months ago on Tinder, and we’ve really hit it off. We’re both single and in our 40s. I’m very attracted to him, and I was initially really excited about having sex with him. But the first time we got down to it, I realized he had a problem. He had an incredibly tight foreskin. He could only achieve like half an erection. When I tried to pull it back it caused him pain, and he lost his erection completely. Also, there was, how do I put it? A hygiene issue as well. I don’t think he’s ever pushed it back, to clean or otherwise. Apparently he once had a girlfriend and they did have sex somehow, but I don’t know see how. One time later he tried to put it in, foreskin and all, and he came immediately. Pretty lame. Normally I would be gone after all that, but I really like this guy.
So I had a delicate talk with him and explained that yes, I have quite a lot of experience in this area and that it’s not normal what’s going on with him down there. He went at my suggestion to a urologist, who agreed. Fast-forward two months later: He got circumcised! He’s healing, but he’s very excited to try things out. Me, too. In a way, it’s really like he’s a virgin. And as much as we like each other, if sex doesn’t work out then, I’m not going to stick around much longer. I know he is suffering from performance anxiety, even now, because he is used to suffering from it his whole life. I want to reassure him, but at the same time I’m tired of foreplay. If he again has some issues, then I don’t know how to deal with it. In a way he has good reason to be anxious because I will be gone if he can’t, after all this, do it. Is that unfair? What should I do? How can I help him?
Wow. You met this guy and 1) within months convinced him to permanently alter his penis and 2) now in even less time are strongly considering leaving him. That is legendary behavior. It’s so legendary, I’d be willing to bet that when uncut guys look into the mirror and say your name three times, their foreskins fall right off.
I want you to get consistent dick because you seem fun and no-nonsense, but I think you owe it to him to see through his hoodless journey a bit further. I have a friend who also had phimosis and was circumcised as an adult, and it’s made all the difference. He was extremely anxious about sex, and now he loves it and is in a satisfying relationship. The snip could prove to be a solution that allows everything to fall into place. Failing that, I urge you to have a little faith and to really exercise patience as he relearns the ropes. If he has performance anxiety already, you’re likely to make it worse by applying pressure to his prowess, at least at first.
Give him time. Take it slow. Explore. You really like this guy (your words!), and you’re still young enough that you can afford to invest a few more months in him (which could turn out to be an investment for yourself). Beyond a few months, I get it, you’ll have to move on. But don’t tell him that. Not yet, anyway.
Dear How to Do It,
I’m a straight male in my 30s. I recently lost my love of several years because I screwed up, again. This is basically the third time that she has caught me being unfaithful and deceitful. Although I have never physically cheated on her and would never want to, I recognize that what I have done was wrong at the time and has hurt her tremendously.
You see, the first time she caught me, I was messaging women on shopping apps about bikinis and generally chatting with them about things. Sometimes I would pretend to be a girl and just act like I’m interested in their bikini, or what they would think of a guy that wanted to wear their underwear or clothes, as if I were a girl and was facing that decision. (I often got blocked.) When she found that on my phone, it changed everything. It came out that I like to wear women’s underwear from time to time, and she questioned my sexuality immediately. Being comfortable with who I am, I explained that I’ve have explored certain aspects of my sexuality, but same-sex encounters never appealed to me.
She began to trust that what I was telling her was the truth, and even took to letting me wear her underwear sometimes. The second time she caught me, after a fight, she had a funny feeling and decided to look at my laptop. I had left an “incognito window” open on my computer. She found a secret email address that I had filled with messages with women from other parts of the country: secret browsers, fake email addresses, alternate names. She was blown away at the lengths I had gone to deceive her and other people. I took my lashings and moved out.
Soon, I begged for her back. She felt sorry for me but told me that the trust was gone. Eventually she began to realize that she still loved me, and we nearly reconnected several times. Then a final reconnection stuck. After many long, honest talks, we decided that she could trust me again. It was good: I wasn’t doing shady things on the internet, and she wasn’t worrying about what I was doing with my phone. But there was something deeper that I could not quite suppress. I am a cross-dresser. My love of the softer girly things does not stop at panties. Sometimes I feel the need to also wear a bra, pull some stockings up my legs. Slip a sexy dress on. Find some heels that fit my awkward feet. I can’t explain it, but it’s my biggest secret.
I can rarely find information on men like me: When I look that sort of thing, it’s dominated with men who want to suck dick, get screwed by a man or a woman with a strap-on. That’s not me. There’s no wishing I could live as a woman forever. No wanting to identify as anything other than myself, and occasionally my feminine side. Privately.
I finally admitted all of this to my girlfriend. Once I was done, I felt an immediate weight lifted off my shoulders. It was surreal. She didn’t say much. I had beaten around the bush on this to her before, and I felt that she would think differently of me. The best I can say is that I feel that now she knows my true self, and I don’t have to hide anything anymore. But of course, it’s over. I’ve lied and deceived for my last time. There is basically no chance of her wanting to take me back a third time. All of that was because I was afraid to tell her that I’m not exactly who she thought. Now that it’s all on the table, am I insane to think that I can’t salvage this trash fire of a relationship? Even during all this, we both acknowledge we have extreme passion for each other, and this breakup is really hard for us.
Your interpretation of this bums me out. While you technically weren’t being honest about your essence, and you were engaging in shady correspondence online, you were effectively in the (fetish) closet! People tell all kinds of lies when they’re suppressing a major part of themselves, and in the most compassionate scenario those lies are forgiven when the full picture is revealed. It’s understandable that she’s wary after feeling her trust was violated, but the lie that killed the relationship—you are a cross-dresser—was told because you were afraid to live your truth. If she’s not going to be there for you, it’s crucial that you are there for yourself. I read a lot of shame in your words, and I think you need to work through it, hopefully with a sex-positive professional.
I’m shocked that you can’t find information about this kink of yours online. I just Googled straight men who cross-dress and got back almost 18 million results. I always thought of it as common enough to be the Wonder Bread of fetishes. It seems quite clear that you need a partner who accepts and enjoys this, which should be achievable. You and your girlfriend have been through a lot, and if she can’t handle your behavior as you fumbled toward self-discovery and the ultimate reveal to her, so be it. She also just may never quite enjoy your cross-dressing as much as you do. But you are who you are, and negotiating non-normative identity with the intolerant world we live in sometimes makes for behavior that is less than ideal.
And actually, your girlfriend’s reaction to your full coming out is the most perplexing thing in your note. How was it a cataclysmic surprise? You’d already been wearing her underwear in front of her. What’s a pair of heels and a wraparound on top of that?
I don’t think you’re insane to attempt to salvage a relationship with someone who has already shown you a modicum of acceptance. But assuming you give coupling another go (and I’m certain you will, given your past pattern), ongoing arguments or tension about your paraphilia should indicate once and for all that this isn’t the right fit. Continuing this pattern of breaking up and getting back together all over your fixed interest in wearing women’s clothing and expecting different results? That would be insane.
More How to Do It
I am a woman seeing a new man. We waited a few dates to sleep together. When we did have sex, he was sheepish to take off his underwear, and it turns out he has a very small penis. I do prefer some size, but he’s eager and good at other things, so I am not too worried about it. He eventually opened up and confirmed the reason he waited to initiate sex is that he wanted to get to know me a little bit so I wouldn’t reject him outright. However, he also told me that his past experiences with women, especially as a teenager, have given him a fetish to be ridiculed for his small penis. Basically, he was really embarrassed to tell me he likes to be embarrassed because of his junk. This just feels wrong to me. I do not think it’s right for me to further pathologize a normal penis variation, even if he wants me to. I feel like he should get therapy for this. What do you think?