#13 HOW I LOST MY VIRGINITY TO MY HIGH SCHOOL SWEETHEART

A little NSFW, title self-explanatory, and the backstory of my wonderful friends my freshman year of uni

I’d been dating HSS for over a year and I’m not sure why I decided that it was time to lose my virginity, but I remember planning the exact day. 

I was still living with my mother and Hannah at the apartments in Ray City, Georgia and my friend Ferron – whom I’d actually met very briefly when we attended the same middle school in Tifton, Georgia but then ran into each other again in uni – was taking me home that day in her Jeep. 

She was always an overly kind and generous friend and there was a point during my freshman year of uni where my friends, including Ferron, would come back to my apartment in Ray City and they’d all hang out with Hannah and my Mum too. No idea why looking back but we’d all have a laugh and talk away the hours.

Ferron took me home that day but we got into a minor fender bender. It wasn’t her fault and I don’t remember if it damaged the front of her Jeep or how long we waited for the police to come in the multi-car pileup. No one had been going all that fast but I do remember Ferron slamming on the brakes and I hit my shins hard against the glove box.

Ferron was beautiful, charming, and full of life – and drama. She was smart and funny and she had a magnetic attraction for men and women alike. She was Korean-American, petite, oh-so-pretty, and had a beautiful white smile (as do many Americans). 

Photo by Simon Maage on Unsplash

She had this other friend – who we’ll call Adam – who was a year younger than me. I think they’d known each other from high school. She’d introduced me to him and I found them both beautiful and fascinating and we formed a morning trio. 

Adam, who looked a little German/Swedish (kind of like a smaller version of Alexander Skarsgård), lived in the most exclusive neighbourhood in our uni town yet he was hardworking and enterprising. He’d started a gardening business when young, buying his own ride-on lawnmower and trailer to haul away the garden waste, and he’d been earning money in his neighbourhood ever since, saving his money and being financially careful. 

I harboured a long-time secret crush on Adam but it was unrequited especially as he observed my messy years with HSS and my later “hot mess” years (where I didn’t want to settle or be caged). He was interesting in that he’d spent one of his high school years in Germany, learning German, and later interning at the German Parliament one summer. He always had a knack for languages as now he also speaks fluent French. 

We had a deep friendship which I loved and appreciated. I loved being in his company, whether it was riding shotgun on our way to Atlanta when he had to run errands, going to his parents’ parties, or attending an International Dinner with him – or simply chatting in my room platonically curled up together. 

We talked about everything. He told me about his travels. We introduced each other to friends, later our amazing Kenyan-Indian friend Naila, who I met in a theatre class. I remember her loving to work out and keep her body fit (and it showed). 

He was there for my Bachelor’s graduation dinner with HSS, his German friend, my Grammy, Mum, and Hannah, all at a Mexican restaurant in town. Our friendship spanned from 2005 when we met to 2011 before I moved to Columbus, Georgia with the whole One Day vibe minus him falling in love with me (except I was the messy Dex character and he was the more practical Em but with a bigger, more exciting life). We’d meet up for lunch or he’d show up on my doorstep at my house and we’d hang out – and then he’d disappear again off to his latest adventure.

Adam later attended Berkley Law and launched a successful career in Washington D.C. and now lives in Paris with his French wife, working on money laundering and tax fraud cases.

Photo by Giammarco Boscaro on Unsplash

He and Ferron were wonderful friends to have. I was lucky to have them. I was lucky they chose me – and stuck with me – especially with the ups and downs of my relationship with HSS.

Adam, Ferron, and I would meet in the rotunda most mornings at VSU’s West Hall, sitting on one of the tables set out for students to use, and Ferron would always approach us with another tale of “You’ll never guess what happened to me?” 

We were sucked into her orbit, her animated way of telling stories by gesturing with her hands – her easy laugh that captivated everyone. I think Adam, like so many of our male friends, had a secret crush on Ferron, but she only had a small handful of close boyfriends and she wasn’t “promiscuous” like me. She was a butterfly no one could catch.

Photo by Michele Bergami on Unsplash

She worked as a bartender at one of “the bars” in Remerton, which was a town encircled by Valdosta that had different liquor laws and licensing. I think she made a small fortune in tips when she worked because she was kind and beautiful.

This phase was during my “innocent years” when I didn’t drink and felt I was distinctively boring like I had to hold myself back because of the boyfriend, HSS, tethered to my ankle.

But when I was planning to lose my virginity I didn’t feel that way. I was still madly in love with HSS and probably thought we’d be together forever, despite the fact I was starting to have crushes on the boys I encountered in uni classes or around campus, including Adam.

As a side note, I kept seeing this hot guy, say, every Tuesday exiting the library as I’d go into the library but when I actually went on a date with him or kissed him years later, there was a reason I should’ve kept admiring him from afar. I’m sure many men I encountered felt that way about me when they got me up close. Like, “whoa, shoulda stayed away from that one!”

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The chosen day: losing our virginity

When I got home, post-accident drama, I invited HSS over to my apartment since my mother was at work. 

I was nervous my first time but HSS was gentle and we held each other afterwards. It’s a miracle (really, truly a miracle) that I never got pregnant because our idea of birth control was the good old “pull out” method plus spermicide gel and I think that went on for years (or maybe I’m infertile, who knows?).

Photo by We-Vibe Toys on Unsplash – unlike this man’s classic 70s chest hair, HSS was fairly hair-free!

Our sex, I’d learn later, was fantastic. He was well-endowed (was I a size whore?). His mathematician/physicist brain approached things like a science. He researched how to go down on me, what would feel good, how to make the best of it. I had zero comparisons so I didn’t know just how good it was until I started moving on to other pastures. 

Losing our virginity together bonded us in a way that couldn’t compete with anyone else at first. He was my safe space. The person who could make my body feel like no other. And despite what dramas happened later, I’m forever grateful my first time or my first five hundred times (because young people can go one to five times per day) was with someone I loved. I hear so many awful, disappointing, traumatic first-time stories and I’m thankful mine wasn’t any of those things.

He knew my deep self (or however deep you can be from aged seventeen to your early twenties). He knew my dark sides, my fears, my anger, and my frustration. My unkind thoughts I kept hidden from others. He knew my longing to be loved and to belong and he used that ammunition for arguments later saying, “No one will love you the way I do. No one cares like I do. No one will like you when they know the real you.”

And those words stick at that age. At eighteen, at twenty, you believe those words. You’re tied to the first boy who makes you come. 

I didn’t realise he spoke through his fear, from the desperation of losing me, of seeing me slipping from his fingers as I longed more and more to be free.

Falling out of love

In high school, he’d been the most intriguing person I’d met but when I started studying literature, my world was open to other boys who studied literature (or other subjects), who could analyse poetry and philosophy and who seemed deep and cool in ways that he no longer did.

Photo by Anthony Tran on Unsplash

And in those intervening undergrad years when we were still together, I remember being cruel to him, getting snappy and angry for goodness knows what. For not being what I wanted and needed. For still being together when the relationship ceased to be fun.

As I had classroom flirtations with other boys, I longed to have that feeling of first dating and first falling in love again. With someone else. I was in love and I was codependent on this boy I’d loved since I was young but I was maturing and I was feeling frustrated by that. By him. 

Long before I discovered vibrators and before I knew how to make myself come, I’d make him reach around and massage my clit and enter me from behind, contorting his hand and arm until it ached, so I could come. He did it because he loved me and loved fucking me, but also because he was young, virile, and horny and this is what you did to have sex with your girlfriend even if she was a bitch and the girls you made friends with told you so. 

I hated how I’d snap at him if he didn’t make me come and I never sucked his cock, thinking it was unfeminist to give a blow job. I’d let him go down on me, giving me waves of pleasure.

Until I was married for the second time, he’d probably been among the top five lovers I’d ever had. 

The good sex was something in the relationship that was never wrong, at least not for me. But it was tinged with the toxicity of first love, of that longing, and growing together and growing apart – of seeing the ugliest sides of another person.

Photo by Sydney Sims on Unsplash

I hadn’t realised how well endowed he was until I was sleeping with the married forty-something professor (I’ll write about later), who was only the third man I’d slept with. He’d said how women usually remarked how big he was but he was no bigger than HSS, maybe even smaller. I’d said they were similar sizes which deflated the professor’s ego. 

The professor told me I fucked like an older woman, which at twenty-two I’d been hurt by, by which he just meant that I enjoyed the sex. I lay back as he went down on me. I let him fuck me. I didn’t have any of that usual performative, pornographic edge of young twenty-somethings – maybe part of the reason he enjoyed the allure of sleeping with his students. 

The young impressionable women who watched porn to please future partners to see what men wanted, a fantasy, and who performed sex as a show. Women who were not in the moment with sex, not able to learn what they liked and didn’t like for themselves. They didn’t know or understand their bodies, unable to let themselves go in the moment. This type of sex, I was convinced, would lead to the kind of mid-life crisis “stay-at-home suburban housewife mom syndrome” where they go all Lady Chatterley's Lover and fuck the help.

Photo by CRYSTALWEED cannabis on Unsplash - I needed this model’s DGAF-kind attitude to life. Sunglasses…in the bath? A towel on your head…in the bath? A necklace…in the bath? Don’t get me started on the makeup!

Hooking up, tethered together

When HSS and I still hooked up after we’d “broken it off,” HSS had told me some of the women he slept with later in uni put him off with their loud moaning and performance but he had loved getting his cock sucked (obviously) which I never did – so good for him that he got something good later, especially for putting up with me.

But now I didn’t belong to him. He was just one of a handful, invited over at 3 am when I was trying to figure myself out. I never wanted to fall asleep alone and I judged the men I slept with by if they took me to breakfast the next morning (usually they did), falling in love or lust over and over again, with all the possibilities of choice, but without the commitment. 

I fell in love with male friends I’d never sleep with – like Adam and Landon – because I was worried the ones I liked would tie me down, cage me like HSS did. I had felt trapped by HSS’s twelve phone calls after every class, always checking up on me, driving by my house, the elephant on my shoulders, his possessiveness.

The thought of marrying him felt like an extension of this caged feeling, disappearing into the yellow wallpaper with all the other madwomen in the attic.

Photo by Liza Polyanskaya on Unsplash

I often felt broken for feeling this way. Why couldn’t I fall in love with my high school sweetheart and be happy and stay in love? Why couldn’t I be the person who only needed one true love? I loved him deeply but I was a horse who wanted to bolt.

His possessiveness and jealousy pushed me away but it wasn’t him really. I had the magic and splendour of falling in love and losing my virginity to that love, of having mind-blowingly good sex as we learned each other’s bodies inside out, the way good long-term partners often do – which sometimes translates to, as Nick Horby writes in How to Be Good, “push button sex” where you know how to push all the buttons to get each other off in record time.

When he asked another girl to senior prom

We broke up once when he was a senior in high school and I was in uni and he asked a girl I was jealous of to the prom instead of me. When we got back together, I insisted he take me and not her because I knew he was into her.

My jealousy and insecurity couldn’t handle him having what would have been a much better time with a group of friends even if he had ended up sleeping with her or liking her or kissing her in the end. At the time, I knew I was being unreasonable but I wouldn’t back down. He did take me to the prom that year and we proceeded to have an absolutely miserable time.

But the bigger question is why did he want me still when I mistreated him? When we argued? When I was a toxic horrible bitch to him? Why do men love those women who are awful to them?

I’ve never ever ever treated anyone as badly as I treated him. I never wanted to feel like that, to crush someone in that way again. I didn’t want him to accept that from me. I wanted him to tell me to fuck off, but no matter what I did, cheating, trying to move on, he wouldn’t let me go.

I regret the way I hurt him so deeply but I was wrapped up in my own emotions and he was the unlucky fallout. But, thankfully, he turned out okay.

Photo by Jakob Owens on Unsplash - none of these men is SAA btw!

How the drama stretched out

In future posts, I’ll talk about how I met the Stella Adler Actor (Dorian) and how he and HSS had gone from enemies to housemates to besties who formed the unofficial “I hate Elaine” club which definitely made parties and going to the bars awkward AF – and how later HSS married Stella Adler Actor’s girlfriend after me, Olivia. Oh, and that time I had a threesome with HSS and HSS’s cousin’s beautiful ex-girlfriend.

List-making

As a random P.S., I’m meticulous about lists and organising (despite the fact I used to have a messy room). I have dug out an only half-remembered Word document on a hard drive, where I’ve written down the names (creepy) of all the people I’ve slept with (maybe that’s semi-normal-ish?), which now I discover is twenty-four.

But also all the names of the eighty people I’ve kissed (only one woman), which proves I was not a rare commodity – some of which (hopefully not all) were the lucky recipients of a hand job – or I let them go down on me (happily), which I somehow did not count as “sex.” To my mind, only v-penetration counted as sex. TMI despite my whole thing being TMI. Maybe I should rename my Substack to “things that are TMI.” Wink.

There will be those who read my accounts and think I was broken and damaged and that’s why I acted like this or allowed myself to have “so many” sexual partners, but to me, I was enjoying my life and doing what I wanted – or at least figuring myself out. I did have some level of restraint or most likely I’d have slept with a whole lot more people. Maybe I should have.

Next time, I’ll talk about the guy who ranted about his ex-wife on our date.

Don’t forget to check out the other twelve posts I’ve written, including the one on why I’m writing this newsletter/blog in the first place.