Sex + Dating

What It's Like to Lose Your Virginity at 35

losing your virginity at 35
Daniel Fishel/Thrillist

I lost my virginity when I was 35.

People find this startling. Then, they calculate. She's fat, they think. Maybe that's how that happens. They have the basic idea, if not all the relevant facts. These days (nine years later and counting) I sometimes forget to share the backstory. I'm fat now, in a way that I see as "Midwestern" or "Torrid catalog." But I used to be fat in more of a way that suggested "Discovery Channel" or "freak show."

​​​​​​I weighed nearly 600lbs once. Then I had gastric bypass surgery at 33, a large amount of leftover skin removed at 34. When I hit 35, I started to date. And that's when things got interesting.

When I started dating, love interests became friends instead

John, the first man I went out with, ran a local poetry reading. We never got more romantic than coffee, but our friendship lasted almost five years. He was a good guy; the kind who crocheted scarves and wrote moving poetry about love. John lost toes to diabetes, then lost weight and did the "right" things. He had a fatal heart attack at 44.

I met Brandon after John. We also became friends. I have a way of collecting straight guys who won't sleep with me.

I've grown close to these men; and they have advised and tended my interests in ways my female friends don't (and perhaps shouldn't). Another friend, Paul, tells me when I'm being a dating idiot.

"I was becoming an Adele song there," I admitted after one breakup.

"You were the whole album," he said. He wasn't wrong: I was 44; Adele's albums 21 and 25 combined, minus two for the actual happy songs in those collections.

There was no template for talking about my virginity… so I didn't

The man I eventually lost my virginity to lent me his Sex and the City boxed set. After that, my friend Bill referred to him as "that gay guy you're dating."

Stephen was actually quite straight. The DVDs had belonged to his ex-wife, and he lent them out on first dates to ensure a second.

I didn't tell Stephen I was a virgin. There was just no script for me to use at 35.

Then one night, he and I tried to achieve penetration for a good 10 minutes.

"Uh, how long has it been?" he asked.

"Thirty-five years… seven months… and, um, what's the date?"
       
We finally managed. Hymens have a shelf life, if you believe the fiction (and I did -- I loved Judy Blume as a tween). Actually, most hymens really do go the way of a bad horseback ride or a fall off a bike. But mine had tenacity. The sex with Stephen hurt a lot more than I thought it would.

My doctor, a tall French-Canadian from Montreal (and Jewish, like my dad and William Shatner), explained that some hymens actually require surgical intervention. And a few weeks after Stephen and I had sex, mine had to be removed. My mother and her best friend drove me for the outpatient procedure. We had catfish at Cracker Barrel on the way home.

Meanwhile, Stephen wasn't good, or giving, or game at all. When I asked if he might go down on me, or do anything to help me achieve orgasm, he said, "Well, we all want that," and then didn't. He also wanted to move into my house, because it was nice and he couldn't manage his roommate situation. I broke up with him.

Weeks later, Stephen stalked me at the coffee house I liked writing in. I gave him his DVDs back. They'd never left the trunk of my car.

After losing my virginity, I got a taste of (almost) every kind of relationship

Loren arrived a few months later at a Starbucks in Toledo. I found him on Plenty of Fish. Given some of the men provided by POF -- one who'd faked his own death, a guy who lived in his mother's basement, a man who saw his kids two days a year but dedicated weeks and weeks to Godzilla conventions -- I started calling it "Plenty Offish." Still, Loren seemed better than all that.

He worked as an IT engineer and had lived abroad. He was 6'6", slightly younger than me, took me to dinner, and wore a suit. He also wanted me to watch him jerk off. He'd never had sex, but had developed lots of ideas from BDSM porn.

I tried the GGG thing, but am more versatile than a true top. I make jokes. I dislike being called "mistress." When Loren first called to ask me what to do with his morning wood, I joked that I needed to have a red phone installed for this, like the one used for managing nukes.

I had a long-term relationship after Loren and I parted ways. I felt like I needed to try all the conventional forms of bad dating before I could really say I'd not only bought my ticket, but stayed the socially acceptable time at the fair.

I learned a lot in those two years... some of which I wish I hadn't. I got to know what it felt like to have someone I love call me names, cringe when a man yelled at me, and call a suicide hotline. The guy on the other end assured me I'd date again. I let him know I didn't care about dating at all. Not then.

It was three years before I experienced enjoyable, fun sex

While I lost my virginity at 35, I didn't have sex I found particularly loving, fun, or exciting until I was 38. And actually, I feel lucky there. Many women tell me that it took far longer for them, even though most of my friends started having sex at a "normal" age. My first poly boyfriend, a married man in an open relationship, knew where the G-spot was. He knew a lot of amazing things.

He still knows, in fact, five years later.

He knows more about me every time we sleep together; but he also knows that I like thrift shops and baking elaborate apple pies. He knows how much I treasure every single holiday. He feeds my cat when I'm away taking care of my family.

My sexuality is evolving, just like everyone else's

I've discovered that I like nerdy, introverted guys who inspire me, by their unique mental wiring, to communicate directly. I've appeared on game shows and have 30-plus years of quiz tournaments and bar trivia matches under my belt. Smart men excite me.

I also lack game. I'd rather just say what I want or need and have the other person explain why those things work... or don't. I love the poly man, but I keep dating. I'd like someone who lives in my house and goes on vacations with me.

But maybe not now. Now, I'm working on a second book and considering other cities I might live in. I travel. I dine out and tell readers about the best places to have arepas or what it's like to watch the setup of Detroit's most beautiful and elaborate masquerade. I gather information. I look for meaning in everything. And I date, but not as a way to create identity.

I've had sex for nine years, but I've known my own mind forever.

A decade later, I now know what I want in a relationship

Last night, I spent two special hours with a man who, as he carefully notes, is not my boyfriend.

We did things I will remember for a very long time. We also held each other and sang "Mack the Knife." We aren't any manner of couple, but I know I will see old movies with him and he will help me decorate gingerbread drag queens this year. Not that everything in life is perfect.

When one recent relationship hit the rocks, I found myself in my mother's room at a nursing home, where she was recovering at 70 from a broken leg. My mother remains formidable; and her decades as a social worker made her a great person to go to for insight.
       
"Sex and intimacy are not the same thing," she said as I cried in her room like a child. "You need to wait, so that you know which you're being offered."
       
Nine years in, this advice governs my attempts at relationships. Sex remains joyful, mysterious, and strange. I like it and do it. Intimacy continues to elude me, though not universally. When I spend a rare night with my poly guy, and he holds me with his whole body, draping one long leg over my hip, I see that these things sometimes happen together; and when they do, it's beautiful and good.

I almost never think about my first time anymore. But I do think about a future with love, where there's intimacy and sex and a shared life. "We all want that," Stephen told me. Maybe not all of us, I suspect. But me? Yes, please.

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Rebecca Golden lives in Michigan, where she’s at work on her second book, Welcome to Detroit. Her first book, Butterbabe: The True Adventures of a 20-Stone Outsider, was published by Random House UK. Follow Rebecca on Twitter @GoldenReb and check out her stories at RebeccaGolden.contently.com.