...back to sleep. You can and should tell her over breakfast—with a loving and supportive smile on your face—that you sometimes wake up when she’s masturbating, and that you’re happy to help her out. But if all your wife wants and/or needs at 3 AM is a quick orgasm, she may not be interested in a full-blown sex session. And if “helping her out” means she’s obligated to get you off before she can go back to sleep, NITENITE, don’t be surprised if she passes (and slips out of bed the next time she needs to have a wank).

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Gay man here with a question about topping. I was a top with my college boyfriend but switched to being mostly a bottom in my early 20s. I'm in my late 30s now, and recently got out of a decade-long relationship, so I've been doing a lot of exploring and rediscovering what I want in bed. While I'm very experienced as a bottom, I feel a bit like a fish out of water when I'm topping. The guys I've fucked have all been very complimentary, so it doesn't seem to be a problem with my technique, but it’s just not as intense for me. Also, I'm uncut and I find that if I'm pushing deep inside someone then my foreskin pulls all the way back while I'm inside to the point that it hurts. (This is especially a problem when a guy rides me.) I'm with a new boyfriend who has enjoyed bottoming for me, but all of this is kind of playing with my head so I can't just relax and enjoy myself when topping. Should I just accept that topping isn't for me?

Subpar Orgasms From Topping

You could accept that topping isn’t for you and swear off topping forever… but that seems a little dramatic, SOFT, and a whole lot drastic. How about accepting this instead: while you prefer bottoming to topping and your orgasms are better when you bottom, you also enjoy topping occasionally, so long as you don’t push too far in and/or get ridden too hard. You might also wanna accept the compliments you’ve been getting about your topping skills/style. Instead of assuming the guys you’ve topped are lying to you, give them the benefit of the doubt and assume they’re telling the truth: you’re a good top and bottoming for you is a good time. And with more experience, SOFT, you’re likelier to get even better at it, earn more praise, and grow to enjoy topping more.

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I am a 60-year-old woman who has had a lot of lovers. My current lover does not enjoy cunnilingus, which happens to be the only reliable way to get me off. How can I make cunnilingus more enjoyable for him? I thought about getting a can of whipped cream to “sweeten the deal,” but will that work?

Exciting Additives That Make Eating Pussy A Lark

It won’t work.

First, putting whipped cream on your clit and labia isn’t good for pussy—and since whipped cream rapidly melts after being applied to the body, EATMEPAL, it’s not going to look sexy or taste good for long. Minutes after emptying that can of whipped cream, you’re gonna look and smell like a newborn puked on your lap. Chocolate sauce, flavored lubes, whipped cream—none of those things have the power to turn someone who doesn’t like eating pussy or sucking dick into someone who does. Pussy is not a sundae, dick is not a candy bar. If cunnilingus is the only thing that reliably gets you off, it’s a new lover you need, EATMEPAL, not a dairy product.

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I’m a male who is curious about wearing a male chastity cage. I’m on blood-thinning medications and I very rarely get erections due to my health issues, but I want to experience the feeling of wearing a cage. Are there any long-term effects from wearing a cock cage for short periods of time that I need to know about? I am just curious how it would feel wearing one.

Looking Into Mysterious Pleasures

You’ll be fine, LIMP. I’ve spoken to a few urologists over the years about the risks of chastity cages for men, and their only concern was potential damage to the erectile tissues when a dick gets hard (or tries to) in the confines of a cage. If you rarely get hard—or don’t get hard randomly—there’s no danger in wearing one even for extended periods of time, so long as it’s not too tight, LIMP, and you keep it clean.

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I’m a 20-year-old woman who just started a new job. One of my new coworkers is a 20-something man who doesn’t speak much English, but he’s made it very clear that he’s attracted to me. I found him on Facebook and realized he has a girlfriend in another country. So, as it turns out, he’s in a three-year-long relationship, but he can’t be with her currently. I’ve always considered men in relationships to be strictly “off limits,” but I’ve got an intense crush on this man and wanna get with him. I’m only interested in hooking up. I’m not looking for a commitment from him at all. Should I let him know I am attracted to him too and possibly ruin his relationship?

Possible Wrecking Ball

Unless you’re planning to post to Facebook about fucking this guy and tag his girlfriend back home, I don’t see how fucking you—even if he’s not supposed to be fucking anyone while they’re apart—will automatically ruin his relationship. Here’s hoping he’s allowed to fuck other women while they’re separated like this, PWB, and here’s hoping she’s allowed to fuck other guys. But even if he were to break the rules to get with you, PWB, it doesn’t mean that he would break her heart… so long as you’re capable of being discreet.

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I learned that you helped pegging get its name. But is there a name for a man using a strap-on on a woman?

Strapped On Dude

In 2001 my readers decided—in a free and fair election—to give the name “pegging” to the act of a woman fucking a man in the ass with a strap-on dildo. Some pegging purists have argued that the word should continue to mean that and only that, but language evolves and changes. These days women peg men, men peg women, women peg women, men peg men, and enbys peg all comers.

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Is it okay to get a quick “happy-ending” massage once a month if you are getting almost no sex in the marriage?

Reevaluating Understood Boundaries

It’s okay with me.

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