Ask TSJ: How to Keep Lovin’ Up On Strange

LIFE IS HARD. It seems like every new day brings a new question that, try as you might, you’re just unable to find an answer for. The Smoking Jacket understands this, and we’re here to help. TSJ’s editor, Melissa Bull, and Headshots columnist, Mike Spry, set aside some time in their busy schedules to answer your questions in a feature we’ve cleverly named “Ask TSJ.”

This week’s incredible question comes from a TSJ reader in Boston.

Dear TSJ,

Please, please, PLEASE answer this. I read so many advice columns online, and yours is the only one that tends to cut through the BS and not try and turn us all into Jesus freaks. (Fuck that righteous fundamentalist Dear Abby broad, amirite?) Anyway, so here’s my deal: I’m 22 and I just finished my degree at Boston U. I’m originally from New York, and my family wants me to move back there now that I’ve graduated. Problem is, that’s also where my high school girlfriend is, waiting anxiously for me to return. What she doesn’t know is that since I’ve been in Boston, I’ve been banging everything with a pulse. Boys, girls, women, men, trannies. I’d like to keep up the double life, riding the Acela and getting ridden by some fella, but I fear that I’ll get found out. I really do love my girl, I just love lovin’ up on strange, too, you know? What do I do?

- Seth, Boston


Dear Seth,

For a moment, and for your personal growth, I’ll ignore that you live in racist, homophobic, Bruin loving Boston. You’re making the mistake that a lot of men make: You’re underestimating your female partner. How do you know that she’s not taking more cocks than my ex-wife in a mens room while you’re away? You think she’s just waiting there for your to come home and enter her once a month? And more importantly, why do you assume that she wouldn’t be open to getting taking from behind by one of your trannies while watching you get horse whipped the girl who lives in the apartment next door?

Dude, women love a good go as much as men, probably more if they can find a man or woman who can get them to scream more while being taken to the absolute heights of sexual ecstasy. You should see what your lady is in to, and if she loves you as much as you love her, there’s a way for you both to stay together while exploring your sexual freedom.

Get. It. On.



Dear Seth,

You’re 22, which makes you the perfect candidate for the open relationship conversation. You say, “Baby, I love you, but I don’t wanna cheat on you. Let’s open up our sexy boundaries. I don’t want to own you, and you don’t want to own me, we live in a post-suburban future of sexual bliss. Let us troll trannies ensemble.”

Caveat: She might not go for it.



Got a question for Melissa and Mike? CLICK HERE and fire away. If we use it… your life will improve immediately. 

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