Lifestyle Sharing the Struggle

Sharing the Struggle: Not Your Average Pillow Talk

Dear June,

I don’t masturbate a lot. But since I started dating my boyfriend, I’ve found myself masturbating more frequently. I love it! But sometimes, I have to imagine sex with my ex because he was, for a lack of a better word, bigger, and I like to imagine rough, doggy-style sex. I have no feelings for my ex, but I do admit that I feel guilty for having to think of him when I feel like I should be thinking of my current boyfriend. (Especially because my current boyfriend helps me to orgasm in bed whereas my ex never considered pleasuring me.) Should I feel guilty? Or is this more along the lines of something innocent?

–Guilty So Please Offer Thoughts



Congratulations! You have discovered the secret to a satisfying sex life. Reaching orgasm through penetration alone is something many women’s bodies just can’t do. That is why it is so important to learn what turns you on and how you like to get off. Should you feel guilty? Absolutely not. So you like to think about your ex? I’ll let you in on a little known secret… everyone thinks of someone other than their partner from time to time too. If no one needed to imagine someone other than their partner, then porn even wouldn’t be a thing!


I do suggest you use your mouth in a way you are probably not expecting. Talk to him (the current boyfriend, not the ex). It is not unusual to desire a larger dick. When we care about someone, we don’t want to hurt their feelings so we avoid talking about things like penis size and skill in bed. Make a vow to put an end to that right now. Tell him how you feel and ask for the sex you want.  The man that is meant for you will have an open mind when it comes to direct requests.

Every man can have a big dick so long as he is willing to strap on. If a man said he would be really turned on if you wore heels into the bedroom to make you a bit taller, would that be offensive? Not necessarily. You can control your height about as much as he can control his penis size. So why do we shy away from the topic? Because men are very sensitive about their penis size. They feel that if we start making suggestions on how to add a little variety to our sex life that they aren’t enough. It’s simply not true and we have to talk more and worry less to get rid of this stigma.


There is nothing hotter to me than a man that wants to see me get off multiple times. If your current boyfriend enjoys getting you off, you may be in luck! He might love the idea of making you orgasm using an extended penis size. Either way, he is still in control. Using a strap on instead of a handheld dildo allows for intimacy that would otherwise be eliminated. It’s also pretty hard to think about someone else when the man you love is close enough to make eye contact. Let’s say he is still hesitant. Find something he loves and make that the last thing y’all do. If he is willing to strap on a dildo and bring you to climax several times, pay that pleasure forward with something he loves.


Strapping on doesn’t mean he is not adequate. It means you have to be creative to get all the things you desire. Sexual compatibility is very important in the long term. If your current isn’t on board or doesn’t care to try, I suggest making him an ex.

Best of luck, GSPOT.

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About June

June was born and raised in the south where “bless your heart” is an insult. Self professed serial dater and an expert in all matters of the heart. June also enjoys volunteering, dancing and sewing.

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