The Dildo and the 30-Year-Old Virgin
When sex and education fail to meet, the questions get awkward.
I spent one year of my life selling sex toys. I’d been laid off for the third time before the age of thirty, and the bills needed paying. In a moment of short-sighted desperation, I signed up for a multi-level marketing company.
I took #bossmom to a new level. I skipped the leggings and lashes: no body wraps or nail stickers for me. I jumped straight to selling dildos. There was a certain appeal, selling sexuality, self-exploration, and discovery. I’d make money and help folks get in touch with their bodies, often literally.
Living in the Buckle of the Bible Belt, sex toy parties were a bit of an odd demand. Sex is sometimes challenging to talk about. Here in Oklahoma, some vocal groups downright demonized it. Our sex-ed consists of “Don’t.” Chastity Balls are a thing here. In my high school, at least half the kids wore purity promise rings, myself included.
I knew for a fact a not-insignificant portion of them were just showpieces, but I’m not going to judge. Had my high school crush offered a slap and tickle, I probably would have pitched my thin silver band into the lake.
But promises to “save yourself” for marriage were standard. Upon entering adulthood and the glorious world of sexuality, I realized how dangerous some of the lessons offered up by our Sunday School teachers were.
First, let’s get this disclaimer out of the way. The decision of who to sleep with, when, and for what reason is each individual’s. You want to wait and experience love-making with only your future spouse? Great. Do that. You want to have a new partner every night? Wonderful. Be safe.
But this innocence and purity movement in my neck of the woods was deeper than making sexually responsible, self-aware choices. My generation was led to believe sex outside marriage (hetero, of course) relegated you to terrible sinner status. You couldn’t even ask questions without painting a massive “slut” stigma across your chest. This created a lot of misconceptions and a lack of outlets to find answers to valid questions.
Because I sold sex toys, I ended up fielding a lot of those questions, despite not being an expert in any formal way. I knew how to sex good and had a box of butt plugs and cock rings. That seemed to be enough for most.
The standard for my sex toy parties was a 20 minute-ish presentation of my “top sellers” and “featured products” to the group. I passed around ridiculous toys, told terrible pun-laced jokes, and touted the virtues of the MLM-branded lube. After that, I invited each guest to a private consultation for them to make their selections.
It was in these consultations where people had a chance to ask all the questions they’d been storing for years. Many clients knew what they wanted or needed. The transaction was cut and dry. Others had many, many, many questions.
One girl with some serious questions stood out. We’ll call her Virginia. She attended a party hosted by several of her sorority sisters, their annual reunion weekend. I and my dildos were the guests of honor.
When Virginia came back for her consultation, I had not held high hopes. She’d not been particularly engaged with the raucous presentation. Virginia sat in the back, categorically refusing to make eye-contact with any of the dildos her sisters were giggling maniacally about. I’d seen her stand-offishness and hadn’t expected to see her in the private room (an optional part of the party for every guest.)
But there she was, still as uncomfortable-looking as before.
“So, did you have any questions?” That was my standard opener. Virginia was quiet for longer than necessary.
“I’m thirty and I’m still a virgin,” Virginia said. There was an odd blend of pride and shame dripping from her words. “It’s by choice.”
“Okay. That’s great.” I was at a bit of a loss. I wanted to ask just how much of a virgin she was. Were we talking “no penetration but lots of other things” or straight-up “never even looked at my own vulva” level virgin? But that felt indelicate.
I went with: “What is it you’re looking for today?” That was invitation enough apparently. Virginia took a deep breath and launched into a full-on confession.
“See, I’m engaged. We’re getting married in three months. All my [sorority] sisters are helping me plan the wedding. It’s great. But they don’t know that Tom and I have never…you know. They were all super, um, active in college. I never could tell them that I was waiting. So I can’t ask them anything. I’d never hear the end of it.” She danced around the vocabulary with practiced agility. I glanced at her hands in her lap. Her left ring finger sported with a stunner solitaire, her right, a very familiar plain silver band.
“Tom isn’t a virgin. He had a few girlfriends before me, and they chose to do stuff. But he’s respected my choice to wait. He’s been so great. I don’t know how…” her voice trailed off. “Anyway, I’m concerned about our wedding night. He’s gonna know stuff and want stuff, and I don’t know any of it. I don’t want him to have to try to teach me when he’s supposed to be enjoying himself. He’s waited this long, and I don’t want to disappoint him. But I have no clue how to…anything!”
The last bit of her explanation poured out at top speed. I immediately felt a kinship with her.
I didn’t lose my own virginity until I was twenty. While I hadn’t waited for marriage necessarily, I’d done a bit more waiting than a lot of my peers and friend group. I understood where Virginia was coming from. I’d had the same awkward conversation with a friend shortly before having my first fuck. I gave her the same advice I’d received.
“Tom knows you’re a virgin. He will have a great time with you, no matter your skill level.” Virginia’s expression softened, and she almost cracked a nervous smile.
“But if you want to have just a teeny head start, the first thing to do is ‘Know Thyself,’” Virginia the Virgin looked puzzled. “It’s hard to get to a place if you don’t know the way. It’s harder if the navigator doesn’t know the way either. If you know the types of touches and sensations that feel best, you’ll be able to guide him to those places and motions. You can find those by just exploring your own body. No partner needed. Have you ever owned a vibrator before?”
Virginia shook her head ‘No’ with quick, tight flicks. She blushed but tried to hide it.
“That’s fine. It isn’t necessary at all. You can do all the exploration you want with your fingers. You can even get yourself off with just your index finger once you find your clitoris. But a vibrator or dildo can either make it go a little quicker or intensify the sensations.”
I pulled out my diagrams (yes, I carried diagrams) and pointed out a few important bits. It was just ten minutes of basic sex ed. This is this — that it is that. This plus that equals wow. Had our sex ed not been lacking or sex made a discussable topic for her, she would have gotten much of that at age twelve.
Virginia didn’t lack resources. She had a sorority worth of women who would have chatted with her. The woman knew how to Google. She probably had a doctor who could have answered her questions more thoroughly than a gal who sold silicon dicks. What Virginia lacked was permission to ask.
It was all Virginia was hoping for. Just a brief acknowledgment that sex, as an act, is weird but natural. Virginia got a good start that day. Not for any information I may or may not have served up. She got a good start because she found the courage even to ask. She ended up buying a dildo just to see what penetration felt like. I gave her some resources she might find useful. I also told her to avoid porn. For her, that wouldn’t be useful at all.
It’s okay to not know everything about sex. It’s also okay to be nervous, loathe it, or feel nothing at all about sex. As a species, we are programmed to understand how to do it at its basest level. As a culture, we learned to enjoy it but there’s no instruction manual. Just some general ideas and a lot of experimentation. Now all that’s left is to learn how to talk about it. We don’t (always) need the details. We do need to have safe spaces to ask questions.
I don’t sell sex toys anymore. But I’m always up for a chat.
So, did you have any questions?
*Disclaimer: Names and some details have been changed to protect privacy.
Here’s more about sex and the toys I sold to help.
Gwenna Laithland is an independent journalist, humorist, and freelance writer in Oklahoma. She writes contemporary sci-fi and is working on her debut novel, Beyond the Sky.
