• Sex

Dealbreaker: His Penis Made Me Cry

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At the tender age of 19, I had only seen a total of four penises: the guy who got into my bed naked after a rave in high school; my boyfriend who I lost my virginity to senior year; the balding dorm mate who I gave an unfortunate blow job to while a James Bond movie played in the background; the older dude I had casual sex with my entire freshman year and most of my sophomore year of college. I had only slept with two of these penises, but this I assure you, all four were of modest size. (I can say this with confidence now that I’m older and have seen many a dick.)

This is where I was at in my sexual evolution when I started dating William*. He lived in my dorm sophomore year and came over sometimes to hang out and wanted to listen to, of all things, Tori Amos. I know! A 19-year-old boy who likes Tori Amos? William’s admission of Tori Amos fandom made him instantaneously more attractive to me. Not that he wasn’t already attractive. With his bleached-blond hair, piercings and post-punk style, when he leaned over and kissed me as “Pretty Good Year” played on my stereo then leaned over and whispered, “I want to fuck you on my balcony,” I felt something I had never experienced before: raging desire.

But I was still fairly young and naive when it came to sex, and I had this rubric I’d devised. I promised myself I’d wait one month for penis or vagina touching, including oral sex. If possible, I would wait three months for sex. So I kept my action to William to kissing, dirty talk and over the clothes groping.

My willpower was no match for William’s dirty talking skills and it wasn’t long before I was willing to push my sex timeline way forward, which was convenient because I was about to leave to study abroad in Europe for four months. So, when William invited me over to his Brooklyn apartment after two weeks of dating to “eat pizza and drink beer” I knew that was code for time to fuck.

When I arrived, there was actually pizza and Corona there! And a mix tape that William had made for me as a going away present. It had Tori Amos, The Rolling Stones, Beastie Boys and more of my favorites. There was also, to my surprise, a balcony. All this time, I thought, “I want to go down on you on my balcony and bend you over the side and fuck you from behind while you hang on for dear life” was part of his elaborate dirty talk fantasy because, um, no 19-year-old in New York has a balcony.

After we ate pizza and I chugged a Corona, William took me out on the balcony, well, it was really more like a fire escape, and lifted my skirt up and put his face between my legs, just like he said he would. This was also the moment that I discovered that sometimes fantasy is better than reality when it comes to sex. While he was doing things that he had whispered into my ear so many times, I wasn’t enjoying it nearly as much as I had anticipated I would. The wind was blowing my hair into my face. I was full from having eaten so much pizza. I kept burping from the Corona. And what about the neighbors? Was anyone watching? I was so paranoid. I pulled his face out from under my skirt and asked if we could continue this back in his apartment. Being the sensitive punk rocker that he was, he obliged.

We crawled back into his window and proceed to dry hump on the couch. Now, I had felt William’s hard dick though his pants before during our dirty talk sessions and thought, That feels sizable. But even with my relative lack of experience, I understood that you never know what you’re dealing with penis-wise until the full package has been unwrapped, so to speak.

After being patient for weeks, William wanted his package unwrapped.

“Fuck me, please. I want you so bad,” he begged.

The boy had put in the time: listening to Tori Amos with me in my dorm room, taking me on dates, talking dirty to me until I practically came in my pants, making me a mix tape. I was about to leave the country for four months and I thought, Fuck the sex rubric, let’s do it!

I unbuttoned William’s Dickies, undid his studded belt and stripped off his Union Jack boxers.

That’s when I saw it: the longest, thickest penis I have ever encountered in my life. This thing puts most porn stars to shame. I’m talking, it was the length of my arm from elbow to wrist. First, I gasped. Then I whimpered. Then I started to cry … really hard.

“I can’t,” I eeked out through tears.

There was no way that mighty python was going anywhere near my frightened vagina. I stopped crying long enough to see the pained look on William’s face. I felt awful. I was a penis slayer. I had to remedy the situation and fast. Just because my vagina wasn’t ready for a 15-incher doesn’t mean there wasn’t some other vagina out there who would be happy to take William’s dick.

“I just … don’t want to get attached before I leave. If we have sex, I’ll miss you so much,” I lied, putting on my most compassionate face.

William nodded, disappointed, and wrapped his arms around me, his python still pressing up against my thigh and finally retreating back into his boxer garden as we spooned on the couch.

William and I wrote letters to each other while I was away. Soon, his letters became more and more scarce. When I returned to New York, he informed me that he had met someone else, presumably a woman whose vagina was far braver than mine.

*Name has been changed.

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