Ask Allister

Q_I’m really into one of my ex’s best friends, but, anytime I try to talk to him or make a move, he becomes disinterested. Why?

A_You’re off limits to him! Sounds like the best friend doesn’t want to betray his friend—your ex. There’s a huge risk factor if you continue to pursue and potential could end up ruining their friendship. And I’m sure you don’t want to do that.

Q_Is there a sex position where penetration doesn’t hurt at first?

A_In the number of positions I’ve found myself tangled in, not one makes the first penetration hurt less. “This is why you want to be the one controlling the speed and depth of penetration. If something really hurts, stop. Trust your own pain threshold. It’s normal for there to be some pain,” says Joe Kort, PH.D., author of Gay Affirmative Therapy for the Straight Clinician. But, some positions can make it less painful, but remember, lube is your ally. The “cowboy position” where you’re riding your partner may be the best position if you want minimal pain as this gives you ultimate control.

Q_I’ve started to date a trans man, FTM, any pointers you can give so I don’t screw it up?

A_ I have a friend who is FTM, and very happy in his relationship. His wife is a lovely accepting woman and glad they have found each other. What I’ve noticed from that relationship is that she helps him build confidence, validating his identity. Be careful with pronouns. There may be days where you might accidentally call him—her, and your partner may become affected by it. If that happens, be honest that it may take some time to get it right. Nobody’s perfect. Lastly, make sure the both of you are comfortable with intimacy. Causing any form of dysphoria, either from your partner or yourself, isn’t going to make for a good relationship.

Q_Swallowing, not a big fan of it. Are there any other ways of giving my guy a BJ without it?

A_Who said you had to do that?! Swallowing is a by choice action and not a requirement. Let your partner(s) know that you’re not comfortable doing that and prefer fair warning. If anybody—whether you’re dating them or just a casual encounter—doesn’t respect your request, then rethinking who you have or might invite in your bed might be something worth considering. Most sexual cases, men like to announce when climaxing. Use that as your indicator to go from sucking to stroking.

Q_I’ve been seeing this guy for two months and really like him. He’s a stage five clinger. How do I tell him some days I need “me” time?

A_Date nights! This will help you both out. Set up specific days in the week—two or three—where the two of you meet to go out. Make one of those days a sleepover, either at his place or him at yours and those days in between are strictly yours. This way his needs are being met including your “me time.”

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Written by Allister Dean

Allister grew up on a steady diet consisting of Sex and the City, Devil Wears Prada, Jen Lancaster, & Queer as Folk. He has dated, hooked up, and screwed up enough to provide insight on your love and lust dilemmas.

Allister Dean is the author of Deliciously Wicked and Brutally Bitter

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