Dear Ty

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Dear Di,

My girlfriend has a dildo she likes to use during her alone time. I’m curious as to what it would feel like in my asshole. My girlfriend will think I’m gay if I ask to borrow her dildo, so I’m planning on grabbing it when she’s not looking. I know you encourage experimentation, so you’re down with this—right, Di?

 —Wanting it in the Ass

Dear WA,

Mission abort!

While I commend your desire to explore your anal cavity, I most definitely do not think you should steal your lady’s dildo with the intent of using it on yourself. You clearly have not thought this one through, have you? If your girlfriend is anything like me, she keeps tabs on her sex toys and will not be happy to discover one is missing. Imagine trying to explain yourself should she catch you mid-penetration.

Snatching your woman’s dildo would not only be deceitful, but could also put her sexual health at risk. For most people, cleaning sex toys is like flossing teeth—we know we should, and we do occasionally, but not nearly often enough. If you were to insert her joystick into your asshole and put it back in her drawer without telling her, she might unwittingly wind up with a lot of unhealthy bacteria in her lady cave.

In an ideal world, you would square your shoulders, look your woman in the eye, and say, “Baby, the feeling of your fingers in and around my asshole would really get me off.” Sadly, it seems you, like so many other unfortunate souls, are not comfortable asking for what you want in the sack. You’re afraid your girlfriend

will think your anal interest means you bat for the other team; however, I really hope your fears are unfounded and you simply aren’t giving your girl enough credit. The anus can be an extremely erogenous zone for anyone—regardless of whether they love the pussy, the cock, or both.

I hope you will work up the courage to talk this over with your partner. What fun is a relationship unless you can be completely uninhibited in bed together?  I suggest you ask your girlfriend to share one of her unfulfilled fantasies with you. You may feel significantly more comfortable spilling your secret desires if she’s revealed something too.

In the meantime, why not buy your own dildo and experiment in the privacy of your own room? Don’t forget to use lots of lube and take it slow!




Dear Di,

I was pleasantly surprised when my girlfriend suggested we spice up our sex life by bringing a third party into our bedroom, which has always been a dream of mine. I immediately started naming off some of her hot friends, hoping she’d be down to invite one of them, but my girlfriend became really defensive and angry. She said she never intended to ask a girl to join us, but instead was hoping we’d include another guy. Now I feel like an inadequate loser and my girlfriend and I are in a huge fight.

—Two Girls, Please


Dear TGP,

I’m shaking my head with disappointment. You came so close to scratching something off of your sexual bucket list, but I fear you really blew it by making such an amateur mistake. You say you feel like an “inadequate loser” because your girlfriend wants to play with someone else’s penis, but did you stop to think about how she must have felt when you “immediately started naming off some of her hot friends”? Not only is it pretty close-minded of you to automatically assume that a threesome involves one dick and two chicks, but it’s downright insulting that you didn’t consider your girlfriend’s needs at all in the matter. Lucky girl, she now knows exactly which of her friends her darling boyfriend is dying to bone!

If you’d like to move out of the doghouse and back to doing it doggie-style, I suggest you start by apologizing to your lady. Tell her—and show her—just how sexy you find her. Your woman is likely feeling pretty inadequate herself right now, so prove to her how hot she makes you. Explain that your thoughtless outburst came from a place of excitement, not insensitivity. You two need to reconnect before you can even think of broaching the topic of threesomes again.

I love a threeway as much as the next sex columnist does, but I have to admit they are very difficult for couples to pull off successfully. It’s all fun and games when body parts are flying every which way, but for couples, the aftermath of a threesome is rarely pretty. I suggest those with serious sweeties think long and hard before they invite someone else to their sack sessions. If you and your significant other simply can’t resist the allure of a third person, I advise you pick someone neither of you are close with. It’s much easier to write off a wild night with someone anonymous than it is with a good friend. Come armed with protection, ideas of naughty sex positions for three, and the knowledge that your threesome just might adversely affect your relationship.




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