Willin’: Size Really Does Matter. By Ida Clare

Willin’: Size Really Does Matter. By Ida Clare

. 4 min read

A new series from an adventurous writer out of Charleston, South Carolina that begins with the painful tale of how she learned that size does matter—and too big can be a painful discovery.

I've been single a long time, a really loooooong time. And in my singleness, I've had long dry spells…loooong. When this particular event occurred, I was well into, but not through, menopause. I met this man online. He was hot, intelligent….and foreign...yum.

We had lunch, then he asked to see my house because he…ready?...restored historic homes in Charleston. He began that vocation by restoring historic homes in Europe. Listen, I’m an educated, progressive woman who lives in rural South Carolina. Any man who can use the English language correctly, with an accent no less, and form cohesive thoughts, turns the “you might want to think about this” part of my brain to mush. Long gray hair, olive skin, white teeth, hazel eyes…a dad bod (I love that)…great hands…hot.

When I unlocked my front door, the first thing he did was brush past me and walk straight into my home looking at the ceiling while explaining what the house looked like originally. He walked me around my house and showed me where the hallways were and where the parlor used to be. My day job is as a theatre historian…I’m all about it. He told me my house had good bones, “like you, dear…” (Holy shitballs). After much kissing, which was uh, freaking amazing (imagine a hot Jacques Clouseau from The Pink Panther, only Chilean, and hot) and then heavy petting, we moved upstairs to the bedroom. “(Kiss!) You know dat dese stairs (Kiss!) are no original? (Long kiss, shirt flies off…) Dis was merely de attick (Kiss!).” I thought, “thank you…finally…a hot, intelligent, Latin (bonus)…Oh MY GOD…Hooray….”

Except, suddenly…

Spinning red lights. Alarms bells. Slap in the face. Full STOP!

He had THE BIGGEST DICK I HAVE/HAD/PROBABLY WILL EVER see EVER! It was otherworldly, alien, colossal, uncircumcised…and terrifying! What was I supposed to do with that? Let me digress for a moment, you know how you have that other person inside of you that we actors call the “observer” commenting on the action, but objective and distant? She totally kicked in. I had seen an uncircumcised penis before, but I had never handled one. And this one was…vast! I handed him a condom, which he had problems wrestling onto that massive thing...no shit… After more hot action, when he slid it in, it hurt like a mofo…a gigantic uncircumcised mofo! Then the whole thing turned…awkward.  Again, that observer: Pain had never happened during sex. What. The. Fuck. Per my observer, as a side note, in my limited experience, it seems the bigger they are, the less they know about pleasure. It’s like a jack hammer…But this guy, thankfully, not so much… I really felt like he felt as uncomfortable as I did.

Regardless of the awkwardness, he stayed the night, held my hand while we slept, made me breakfast, then had to drive back to Charleston for work. After that he called daily, wanted to know when he could see me again. I left for an extended summer trip three days after our encounter. He continued to call.

Do you know that if you don’t use it, it closes up? I didn’t either. Vaginal Atrophy. I felt as confused and self-conscious as I did my first time. At my in-the-middle-of-menopausal age, he was my first one-night stand… See, I can count the number of men I've slept with on two hands. I'm a Scorpio sun/Cancer moon/sex has to be a spiritual experience. Plus, being raised in the rural South, it has taken me a long time to manage, and I say manage not conquer, that whole guilt about sex bullshit. For a split second, I thought maybe I deserved it because it was a one-night stand. I thought and thought and obsessed and then…I got angry. My various fucking GYNs never mentioned this possibility. It’s not like they don’t ask you at every appointment if you are sexually active. You would think vaginal atrophy would be something of interest to an aging, single, sexually active-in-spurts woman! So, I had to educate myself. I didn’t know about lube (never needed it). There are even dildos, for lack of a better word, to help expand what has contracted…didn’t know that. “Back in my day” we were worried about “stretching out.”

Oh, and hot Chilean, Jacques Clouseau? Never saw him again. Absence does not make the heart or the big dick grow…fonder…or more comfortable.

The Crush Letter
The Crush Letter is a weekly newsletter from the Dish curating intelligence & stories on all things love & connection - friendship, romance, self-love, sex. If you’d like to take a look at some of our best stories go to Read Us. Want to get some?


"Don't Touch My Hat.*" Midlife Men & Loneliness 5 Things That Turn Me On: Ali Waks Adams 5 Things That Turn Me On: Bob Guccione, Jr 5 Things That Turn Me On: Craig J 5 Things That Turn Me On: Dish Stanley 5 Things That Turn Me On: Jane Boon 5 Things That Turn Me On: Lady Verity 5 Things That Turn Me On: Liza Lentini A Turntable and a Candle: F-ing Classics About Face: Skincare Essentials for Men An Upbeat Playlist for the Divorce-curious And I Wondered ... Do We Really Need A SATC Reboot? Bisexually Anxious Among the Noodges. Review: shiva Baby Book Review: A Certain Hunger by Chelsea G. Summers Book Review: Norma Kamali: I Am Invincible Book Review: The Lover. By Marguerite Duras. Book Review: The Story of O CRUSH Summer Reading List! From CRUSH Reader Sharon Weinberg, Owner of The Chatham Bookstore Dear Dish Dear Dish. About those summer orgies ... DEVOUR {things to do, have & know about} Dish Gets A Kink Assessment. Doing Nothing With Friends French Kiss: French Girls Do It Better, Right? Grief. By Lauren D. Weinstein Hefner. By Bob Guccione, Jr Hide A Love Note In Their Pocket. Hook Ups: Hilary Harley, Astrologer Hook Ups: Meet Barrie Rosencrans, Spa Director & Dharma Yoga Teacher Hook Ups: Meet Heather Fink, Founder & CEO of the Sexiest Beauty Hot Thots I'm Dish, the Master of Ceremonies Let's Reconsider, with Adam Grant Love & Mike's "Bad Girl Pasta" Love / Sex / Moon Magick. Mercury Retrograde fucks sex. Not in a good way. Love/Sex/Magick. Hey There, Lover! By Lynn Eaton Love/Sex/Moon Magick: Endings, Happy and Otherwise. By Lynn Eaton Nice to Meet You. How Are You Crazy? Oasis in the Desert. One woman's honest journey through vaginal rejuvenation. OMG Yes. Podcast Review: Dying for Sex. Why You Need to Listen to Molly's Journey. PrimeCrush & Chill: Movies Worth a Re-Watch Quiver. Sexual Debut Stories: Violet Reports from the Edge: Skirt Club. By Jane Boon. Reports from the Edge: Solo at the Sex Party Six Ways to Get the Friends Who Count Snapshot Rec: Get Yourself Sexify-ed on Netflix. Snapshot Rec: Read Liza Lentini on the Indigo Girls in SPIN Songs That Make You Wanna F*ck Stanley Tucci Is Paradise Stories & Conversations The 3 Things You're Really Fighting About The 4 Most Common Skincare Issues for Men (But Were Afraid to Ask). By Lauren D. Weinstein The Dynamics of Friendhip By Lauren D. Weinstein To get all of us, subscribe. Willin'. Size Really Does Matter. You're My Medicine You're Wearing A Turtleneck, Again? Your Love Is King & Queen, GQ