Dear Bearded Confidant,

I am 23 years old and about to get married to the love of my life (female). I have a curious side but I don't want to mess around with guys. I want to feel anal penetration performed on myself, and I know they have strap-ons for women to use on men, and I would love for her to use it on me. She has fingered my ass once, and I really enjoyed it. But she has since stopped that. I move her hand down when she's performing oral on me but she always stops right before the asshole. What can I do in bed to set the mood for her to fuck/finger me? I am up for any suggestions!

Dear Straight Anal,

Reading between the lines of your question, there are two issues that need to be addressed.  First, your fiancée isn't especially into finger sex, or she'd be volunteering to do it.  Second, for whatever reason you're not comfortable asking to be fingered or probed with a strap-on, or you'd ask for it and already be enjoying the action.  Now don't assume I'm being critical of you in any way -- to be a straight man is much tougher than people typically realize, because heterosexuality can never be taken for granted and must be re-established and reinforced constantly.  Any sort of anal penetration instantly calls a man's sexual orientation into question.  If I may be so bold, that's why you're shy about boldly telling your fiancée to stick her finger up your ass -- it would be the manly thing to do to state your desires, but being penetrated goes against societal definitions of masculinity and male heterosexualty.  So you're left hoping that your fiancée will read your mind, and meanwhile your fuckhole gets blueballs (so to speak).  But never fear -- I have a suggestion!  Don't talk about getting fingered like you're suddenly a pussy bottom (not that there's anything wrong with that), but rather tell your fiancée that you want her to feel your prostate as you pump your load.  In other words, make it about her experiencing your masculinity from the inside.  Make it about how stimulating your prostate makes you cum harder and ejaculate more.  Make it about being more of a man and less of a pussy.  When you look online together for sex toys, don't look for strap-ons, because those tend to be penis-shaped and this isn't about you getting buttfucked by another man.  Instead, search directly for "prostate toys."  (TLA has an entire line of non-penis-shaped prostate toys.)  Let me know how it goes, buddy!