Hereās a story about the time I almost lost my virginity. This is of course a social construct and by a broader understanding had already been lost years earlier at a sleepover with my best friend. But I digress.
I was dating a boy in high school. I shall call him Drama Boy. DB was big into theater, he made home movies and did stage performances at his high school.
Now. I must make this notation here, because the ending to this story will be savage otherwise, but DB put entirely too much of his mental well-being on my shoulders. He was often depressed and it was my job to constantly be helping him to regulate that.
The night our story took place we had been dating for eight months. During those months had been a ludicrous amount of making out and groping, even one lusty fumble that almost ended in penetration I vetoed on the grounds of not having a condom. Itās worth noting the first time we made out I felt physically sick to my stomach but I assumed that was normal.
But our parents didnāt give us much opportunity to really do anything like we imagined real sex to be. Until he came over for a movie night and my parents left on a date.
Scandalous, some might say, of my parents to leave us unchaperoned. But my parents were very blasƩ about sexual topics. They knew I was well educated and careful. Their leaving was possibly a gift of privacy rather than carelessness.
So when DB arrived for our movie night, we both knew This Was The Night. The night weād lose our virginity.
We were both nervous and excited. The weight of societal pressure blanketed both of us, convincing us that this was the most momentous night of sex either of us could ever have.
DB chose a wretched movie. We sat through the first part dutifully before we started making out sloppy style. As Iād said previously, weād done plenty of making out and hand stuff. Which is why I noticed that DB did not seem to be as⦠rigid as he had on other occasions.
A kinder more mature lens has softened my perspective. He was so nervous. But at the time I was a bit offended that I wasnāt arousing enough to have him standing at full mast. Still, we forged ahead.
I sat patiently while he tried to unhook my bra, boredly watching the terrible movie in the background as he soldiered manfully toward defeating the two clasps containing the bounty of my bosom while insisting he didnāt need my help. It took about five minutes.
That out of the way we made out some more. Then DB pulled out his pièce de résistance. A condom. This was a big get for him. His family, unlike mine, were horribly conservative and of the opinion that marriage was worth waiting for. So his opportunity to secure this vital piece of equipment had been slim.
In fact, it had been so slim, that what he pulled out was an:
I wasnāt terribly enthused about any of those qualifiers, but I held my tongue.
Then came the worst part. DB couldnāt admit that the stress of performance had unmanned him. He continued to pretend his wobbly erection could facilitate the rigorous activity of putting on a condom. He attempted to force the dry clinging rubber down his dick as it softened like pudding under his fumbling hands.
I butted in and made with more kissing, certain that seeing me naked had been such a let down that he was going limp because of me. Surely the sight of my boobies should have been enough! Because they werenāt, I was convinced he wasnāt really into this deflowering at all.
It didnāt help that my enthusiasm for this activity was fueled purely by teen hormones rather than actual sexual attraction. Perhaps he felt the same. It was one thing to watch his penis with clinical curiosity but another to think that my young boobs didnāt excite the same lust I felt toward boobs.
Nevertheless. The condom was more or less on. With momentous energy he tried to jam our anatomy together and rolled a critical failure. His penis lost all rigidity and oozed away from insertion.
Panicking and embarrassed he exclaimed, āI think I put this on wrong!ā
To my horror he began trying to remove the condom and put it back on the other way. Health instructors of ages past screamed in my head that the condom had now been stretched and unrolled.
Trying to jam it back on was certainly not safe, especially given the slackness of the anatomy in question. It would certainly tear- if he could even get it back on.
I broke out in a sweat watching him attempt the magic trick of convincing a flaccid penis that it really wanted to get better acquainted with a desiccated rubber tube prison.
āI just remembered!ā I exclaimed.
He looked up at me, wretched with despair.
āI promised my parents I wouldnāt have sex tonight. I just remembered! Sorry!ā
This could go down in history as one of the most bold faced and terrible lies ever told, a blatant falsehood on par with declaring the sky was green. But his face broke out in a terrible relief.
He disposed of the abused condom and I resecured my bra and we resumed watching the horrible movie, both of us relieved in our own way to set down the burden of Losing Virginity.
The next day I broke up with him.
This remains to this day one of the most savage things Iāve ever done, breaking up with someone the night after impotence.
But remember, dear reader! It wasnāt just the sex! His depression had already worn away my patience and our communication. The foibles of the night before had just illuminated the gaps where we couldnāt talk to each other properly. I was constantly comforting him over something, shoring up his brain chemistry with my relentless positivity.
Iād like to say thatās all it was, and look more charitably on my young self. But truthfully my tender pride had also been badly stung that I wasnāt worth rising to the occasion for. Comforting him over this latest mishap when my feelings were hurt was more than I could swallow.
DB took the breakup very poorly. About two weeks later he lost his virginity with the new girl he was dating. He called me to brag, sniffing through the airwaves for hints that heād hurt me back.
When I congratulated him with utter sincerity and not a whiff of jealousy he was furious.
We stopped speaking for years, except on our mutual birthday when weād wish each other a cordial āHappy birthday.ā
He messaged me out of the blue one day years later to catch up. He was working in food service now. Was it true I was a lesbian? Yes, I assured him, that was true. He thought that was pretty cool.
Then he told me about this bisexual girl he worked with who was interested in a threesome. Did I want to have a threesome with him and his bisexual coworker?
The audacity. I couldnāt believe it. My mind filled with savage retorts like, if you understand Iām a lesbian why do you think Iād want you to be part of that? Why wouldnāt I just sleep with her without you?
But I remembered the utterly ruthless way Iād dumped him and as penance I swallowed all of the things I wanted to say and instead politely told him I was seeing someone, but thanks for the offer.
And that was it. Heād managed to shoot his shot not once, not twice, but three times, and never managed a home run. He struck out that last time, and we never spoke again.