#AskPlayboy: Jenny Mollen on Cleavage Optimization

By Jenny Mollen

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Jenny Mollen answers one guys quest to utilize his girlfriend's boobs to their best potential in the sack.


The first fully hardcore porno I ever watched was a copy of a copy a hundred times copied of a jailbait video from the ‘70s, wherein a girl and her high school boyfriend get naked and get it on while her parents think they’re doing homework in her bedroom. They fuck in various positions, but the cumshot happens (predictably) on her chest/face following a vigorous tittyfucking session.

Even as a Fully Grown Adult Male, I have never been able to get that image out of my mind. Neither have I ever had the courage to ask a girl to let me do her boobs. I have so many questions (Do women even like it? Does the novelty make up for the fact that the vagina is an infinitely better-suited place for a penis to go? Who thought of it in the first place?) but what they all amount to is a mental block that has prevented me from ever screw a pair of tits. So, call me naïve, call me a prude, or just call me (maybe) and we can hash it out voice-to-voice, but what I need is a full breakdown of T.F. etiquette: Who, what, when, where and why? What about the finish—does that need to be negotiated or is it a given? Finally, is it necessary to ask first, even if you’re already in the sack together anyway? My breathing has just gotten heavy (panic attack, not arousal). Help.

Rule of thumb: If a woman is sleeping with you, her main objective is typically to turn you on unless of course, you are married to her. Then, she’s probably less concerned with your experience.  But for the most part, women want to feel like they are blowing your mind in the sack. If fucking her tits is going to do that, go right ahead. As a woman, I don’t remember ever being super turned on by being the buns to a guy’s penis hot dog but I also know it’s never felt like a huge demand physically. I’d actually be kind of psyched on a guy whose fetish required zero to no real exertion on my part. So I say, fuck away! As for the finish, cumming on her tits is not only a given, it’s most likely preferred! Especially for those “I’d rather eat my calories than drink them” types. Your mental block is the only thing standing between you and your fantasy. Stop thinking with your head and start thinking with your cock. 

Jenny Mollen is a writer, actress and all-around gorgeous sassy badass who lives in L.A. with her dog Teets and husband Jason Biggs. She writes about her life on TheSmokingJacket.com in her highly popular column What She Said. Follow her on Twitter at @JennyAndTeets and on Instagram at JennyAndTeets2. 


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