Q: I’m a relatively inexperienced 26-year-old young lady. I have basically spent the last four years celibate, in a dead-end relationship that I’m finally out of. Recently, I met a much older man, 41, who is extremely experienced and has had a history of being totally freaky (golden showers, porn, etc.). He’s got a pretty healthy sexual appetite, and I’m having fun trying to match it. (Gotta make up for those four years.) We’re talking about moving in together and he’s assured me that he’s still freaky but ready to settle down and commit.
My question is, what sorts of REALLY exceptional things can I surprise an experienced “pro” with? I don’t always want to be on the receiving end, and want to show him I’m committed to keeping it interesting. Unfortunately, I don’t really know any great tricks (I’m talking showstoppers, if you please), and the stuff I’ve read so far seems a little tame. —White Bread Girl No More
A: I could go all Cosmo on your ass, WBGNM, and throw down a list of 101 Sex Tricks That Will Drive Your Man Wild! But I don’t think those lists are particularly helpful. For instance, I remember reading one of those Cosmo lists, and recommendation #67 went like this: “When you’re out on a hike with your man, slip a small, smooth stone into your pocket when he’s not looking. Then when you’re making love in an open field, retrieve the stone and gently press the small, smooth stone into the sensitive spot between his testicles and his anus. Guaranteed to drive him wild!” Guaranteed to drive him off is more like it. Can you imagine what would transpire if someone actually used this trick?
Him: Oh, baby. [Huff, puff, etc.]
Her: Oh, baby. [She retrieves the stone from her pocket.]
Him: Lay still, would you? [Huff.] What are you reaching into your pocket for? [Puff.]
Her: Nothing! Oh, baby. [She presses stone into the spot between his testicles and his anus.]
Him: [Jumping up.] What the fuck was that?! What the hell are you doing?
Her: I’m pressing a small, smooth stone into that sensitive spot between your testicles and your anus!
Him: Why the fuck would you do that?! If I ever want a rock pressed into the sensitive spot between my testicles and my anus, I’ll let you know, okay? Christ!
The moral of this story? There isn’t a list of really great tricks out there that will drive your man wild. In your case, WBGNM, I’ll bet your freaky boyfriend not only loves you for being willing to try new stuff with him (like watersports and porn), but also enjoys taking the lead, corrupting you, and being the instigator of all the freaky shit. For the time being, kiddo, why not relax and enjoy being with someone who’s more experienced?
Q: About a year ago, I accidentally stumbled on some of my father’s Internet porn. It wasn’t tranny or she-male or bondage/SM or gay. It was women who had been digitally altered to have multiple arms, legs, facial features, boobs, etc. I find it really creepy. Since I was 13 (I’m in college now), I had been sneaking into his print/video collection (for my own exploration), and most of it used to be girl-on-girl or straight porn. I assumed that this was going to be his consistent pattern. To further this conundrum, I’m pretty sure that my father can’t really explore this fetish with my mother, since multi-arms is, to my knowledge, impossible.
I’d like to know what this is all about. How can I confront him without things going … weird? —Can’t Reasonably Explain Extreme Perversion
A: One of the odd things about this job is that questions come in waves. For weeks every other letter will be, “What’s a cock ring?” Then it’s all, “What’s up with she-males?” or, “How can I get my girlfriend/boyfriend to piss on me?” For the last few months it seems like half the mail is from people who feel obligated to confront their fathers about their Internet porn collections. What the fuck, people? Why can’t your dads enjoy their Internet porn in peace?
Take your case, CREEP. Your dad’s perversion may be extreme, it may have given you the willies, and exploring this fetish with your mother (or anyone else) may be impossible. But so fucking what? What the fuck does it have to do with you? Why on earth would you even contemplate confronting your father about his freaky porn collection? Your father doesn’t have to answer to you about what he jerks off thinking about! Christ!
Q: My current boyfriend is addicted to watching my ex-boyfriend fuck me. This is all my fault. I wanted to have a girl-boy-boy three-way, partly because I couldn’t resist the idea of seeing my ex (buff, dark, tall) and my current (buff, blond, tall) naked at the same time. (I’m hot, they tell me, but they’re scalding hot.) My current was reluctant at first but decided to be good, giving and game. (Thank you, Mr. Savage, for the three Gs. Throwing down GGG is getting more of your readers’ fantasies fulfilled than anything else you’ve ever written.) My ex tied me up for a little foreplay. My ex and current licking me while I was tied to the bed was pretty awesome. Then my ex untied me and decided to tie up my current. Then my ex proceeded to fuck me. This drove my current nuts. Right after my ex came, I reached over and touched my current’s cock and he came instantly. We’ve repeated this scene four times in four weeks. My ex is coming over tonight.
I’m not going to ask you the usual straight-girl question — I don’t think my current and ex are secretly gay. My current and I still have regular sex and the only time my ex and current touch each other is when they bump heads on the way to my tits or my ex is tying my current up. I do worry, however, that I’ve created a monster. My ex is my ex for a reason. I broke things off with him because, while he’s nice to look at, I don’t enjoy spending time with him. Now to please my current I’m having sex with my ex all the time.
We clearly seem to have stumbled over my current’s ultimate turn-on. I don’t want to be non-GGG, Dan, but I don’t want to fuck my ex once a week. What the hell do I do? —Double Boy Trouble
A: You tell your current that it was fun while it lasted but you’re not going to be fucking your ex anymore. You can soften the blow — and maintain your GGG cred — by reassuring your current that you’re not saying no to getting fucked in front of him by someone else while he’s tied to a chair at the end of the bed. That you’re game for, right? You’re only saying no to doing this with your ex. Promise your current that if and when another guy comes along — a guy you both like and trust — you will ask that guy if he’s GGG. But until that guy comes along, you and your current will have to explore some fantasies together that don’t involve your ex.Send letters to [email protected]
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