So here’s my dilemma. My boyfriend is a solid 9. Not a Grindr 9, but like a real 9. I love being on bottom.
And I always thought I was a good one until I met him. Now he has me questioning my whole sexuality. Just kidding, but not really. I really adore him, but I just don’t see how my ass can handle this, especially until death do we part. Is there any hope at all?
-Hopeless Bottom in Oakland Park
Trust and believe, you absolutely can handle your boyfriend’s gift. Lean into foreplay and give your body time to warm up and prepare. Using smaller dildos or butt plugs during foreplay can help you relax and get ready but still have intimate fun while you wait for the literal big event. You can also try Anal Ease, but apply it and wait 5-10 minutes for it to dry and absorb; otherwise, your partner’s pickle might go numb, and neither of you will have fun. A clean hole is a happy hole, so also make sure you’re doing your prep work before you’re going to impale yourself. All things are possible with a bit of patience. Pro tip: before he makes his grand entrance, take a deep breath, and when he’s ready to dive in, slowly release your breath. It will naturally help you to open up and welcome him home.
I am a bisexual woman in a heterosexual marriage. A few years ago, my husband and I decided to explore an open marriage so I could feel fulfilled in the full spectrum of my sexuality. This was exciting, new, fulfilling, and fun for a while, but connecting physically with a woman in his presence has started to feel very performative and as a result, inauthentic to me. I know when he comments on how “hot” it was he isn’t intending to downplay the experience for me by making it seem as if it’s for his benefit, but that’s how I end up feeling as I’m interested in connecting on a more private, emotional level also. Should I ask my husband whether we can play separately, or just accept the “girls gone wild” nature of the status quo and be grateful?
A marriage is only as successful as the honesty of the people in it. The most important thing you’ll ever say to your husband is what you want and what you need. It is not selfish to do what is best for you. You have to tell your husband where you are in the experience and honestly discuss what comes next. You both started this journey together, and like all things, this journey will evolve, and now it has. There is never a good time to do a hard thing, but you must. You also need to ask yourself if you’ll be able to handle your husband playing solo. All of this is really about boundaries and communication, but the most important thing is that you be your whole self. Have the hard talk. Get uncomfortable and get honest. It’s the only path forward.
Have a question for John Porter? Fill it out HERE.
John Porter is an entrepreneur and founding partner at Oasis Asset Management. He has served as a political organizer and strategist within the Democratic Party, as well as serving as an executive board member for the Miami Yacht Club.