Dear MJ,

I have been dating my girlfriend for six months now. Everything has been running smooth with no significant speed bumps. 

We recently went out in the city and happened to run into her old boyfriend. I didn’t make a big deal of it. Shit like that is bound to happen. 

The next night I was at her place and we were having sex. Everything was going as well as it always did, until she started to play with my anus. To be honest with you, it felt pretty good. My concerns go a little deeper than that. 

Was this something she did with her old boyfriend or was it a matter of circumstance? I highly doubt the latter, but I am trying to find a better way to approach this than saying “Eh Hun. Did your ex like it when you shoved a finger in his ass?” 

My Hershey Highway

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Dear Hershey, 

I thought you were going to say she called you the ex’s name in bed! Now, THAT is something to get upset about. Your girlfriend trying to spice your sex life up a little, is not.  

I seriously doubt seeing said ex provided inspiration for the act in question. Humour me for a just second: do you actually think after running into her ex unexpectedly, that your girlfriend spent the entire next day remembering with fondness how she probed his anus, then, with the thought still fresh in her mind, got into bed with you and boom!, instinctively began fingering your asshole?  

Highly unlikely.  

I can pretty much guarantee your girl did said act because she thought you would enjoy it, not because she was dying to insert her finger in an anus- any anus… and there you were. 

In fact, knowing girls the way I do, here’s how I think the scenario actually played out: the two of you unexpectedly bump into her ex. She walks away from the encounter feeling slightly shaken up but mostly happy thinking: “what a TOTAL LOSER, thank heaven I now have this wonderful guy in my life instead of that lying, cheating dip-shit. I hope he noticed how happy we are- sucker! I can’t wait to run home and get naked and because I love my gorgeous new boyfriend sooo much, I’ll even shove my finger up his ass because that’s what I heard guys are into these days”.  

You said your relationship was otherwise perfect so why create problems where there aren’t any? If you really like this girl and have any desire to keep her in your life, my advice to you is this: stop being so paranoid. Women are attracted to confidence.  

It’s not going to suit anybody (least of all you) to sit around obsessing about why your lady suddenly wanted try out this new thing in the bedroom. Just be happy! She’s trying to find new ways to please you!! If you’re not a fan of the ass game, tell her. I can say with absolute certainty that she’ll be just fine with leaving the proctology exam out of the equation if it’s not your thing.  

Yours in love,

MJ