Sexuality

I went out with my old friend Judd — both of us in open marriages — to a lively cocktail bar with the half-joking aim of flirting. We met a group of women at the bar, including one particularly fun blonde, and I reflected on the rarity of having a true wingman and the ongoing question of whether Sydney will call.

I’m exploring a layered erotic fantasy involving Margot — a woman I know who escorts — structured in three tiers: a private tryst with her directly, a scenario where she procures a companion who meets my specific preferences, and a third fantasy combining both where she participates alongside that companion.

I reflect on a conversation with Margot about her unrealized fantasy of double penetration and a gangbang, realizing what excites me isn’t the act itself but the trust she’d place in me to keep her safe while curating such an evening — and the gratitude that might follow.

I’ve dated several beautiful, intelligent women recently but can’t muster a physical response. With Tina, whose voice is catnip, the problem is she’s not submissive — when I asked her to wear something green and she deflected, every alarm bell went off, and now, shamefully, I want to run.

I’m writing about Isabella, one of two women who taught me the most about my sexuality. She showed me my cock could be an object of desire, while the Secretary taught me my desire itself could be desired. I miss them both — not just for sex, but for the intimacy we shared.

I’m reflecting on how shame has shaped my life and my blog since 2010 — from the radical openness I once had in writing about my most uncomfortable impulses, to the self-judgment and contempt that have crept back in now that I’m less anonymous and less self-accepting.

Yesenia has effortless elegance, always-impeccable style. I wonder what she wears beneath. Everyone should only wear things that make them [feel] hot.

Meeting women has changed dramatically over the last 15 years — from mass-swiping Tinder to the blog attracting partners organically — and now all avenues have dried up.

I’m marking the 15th anniversary of my blog, a few months late. What began as exhibitionistic and therapeutic has become a memoir of my inner life through my fifties.

Every behavior, sexual or otherwise, contains valuable information. Lately my pornographic habits are raising disturbing new questions I’ve been avoiding — ones I plan to explore in a future post.