I Tried Anal For All The Wrong Reasons


We all have something that we are ashamed of. For me, it’s the fact that I still hook up with my high school ex-boyfriend when I go back home. Oh, and the fact that I’m still hopelessly in love with him. Let’s call him James. James and I started talking again when I still technically had a boyfriend (I know, I’m that girl). At first, it was very platonic. But after a few months, it seemed like a little more. We would talk about how much more compatible we were now that we were older and in college and how it would be when we were both single again, blah blah blah.

Before I knew it I had caught feelings. I broke up with my boyfriend for reasons unrelated to James, and I thought this was finally our chance. Our do-over. Spoiler alert: it wasn’t. We didn’t get back together because life isn’t a fucking fairytale. I knew deep down that he didn’t want to get back together. But I thought I could make him want it. I tried my best, but nothing changed. He would invite me over to “hang out” and we would just end up having sex. I thought if we hung out enough, those feelings from high school would flood back and he would realize how much he missed me and how perfect we were together. But they didn’t. He was using me, I just didn’t realize it.

The healthy thing for me to do would be to walk away. But I didn’t because a) I’m a masochist who loves psychological torture and b) it was literally the best sex I had ever had. Earth shattering, mind blowing, you name it. I didn’t even want to think about how he got so good.

Soon I shamelessly began making the two-hour drive back to my hometown just to see him. And I lived for it. I lived for the hours of conversation we had while lying in his bed before we got around to any penetration. I lived for the sound of his deep voice and how he smelled the same as he did six years ago when we dated in high school. I was hooked. But he wasn’t.

One day, word got out in my sorority that my best friend does anal with her boyfriend. The topic came up while we were on the bus to our chapter retreat. I was shocked.

“You do anal?!” I asked her, shocked.

“You don’t?!” she replied.

Her response was spot on. I had always thought of myself as the most sexually experienced in our friend group, being the oldest, and clearly she was taken aback that she had something on me. And so was I. I knew it was time to up my game.

Many guys before had propositioned me but it didn’t feel right to let some rando bury himself in my ass. Maybe it’s just what I needed to move out of the lower ranks of being a fuck buddy. If I could give him something no one else could, he obviously has to love me back, right?


Thanksgiving break rolled around and I was back home for a whole week. I had asked James if he was down and he was. Of course, he didn’t believe I would actually follow through, so there was no way I could back out now.

As per usual he texted me around 1:30 a.m. telling me he was leaving the bars. And then I got the “Don’t hate me but…” text. His friend had locked them out of his apartment. Thirty minutes later I was picking him and his friends up from downtown. Even his friends were the same as I remembered, talking shit in the back seat. I dropped them off at their building. Forty minutes after that, James and I were quietly sneaking into his parent’s house. His yapping dogs greeted us at the door.

“You owe me big time for this,” I said. “You could be sleeping on your frat house floor right now if it wasn’t for me.” He rolled his eyes and told me he’d make it up to me.

I casually tried to play it off like I was doing him a favor when in reality I just wanted to get laid.

When it came time for the anal, I had to do it. And if there is anyone out there that says it isn’t the worst, they’re lying. Okay, maybe it wasn’t the worst but I couldn’t wrap my head around it. I wanted it to stop but at the same time, I didn’t. So naturally, I just stared at the wall until I couldn’t handle it anymore. And then it was over.

The next morning I woke up to a dog licking my foot. We were both naked in his bed and I heard his mother’s voice say “Hey James, I’m leaving for work. Your father and sister went to the shooting range.” He grunted. I lay as still as possible. “Hey Lauren,” she said. I said hi back but kept facing the wall until I heard the door close behind her.

Did his mom really just say hi to the naked girl in her son’s bed?

I stayed in bed for a few more hours until he woke up. We talked for a while and eventually we did it again. And again, well into the afternoon. I left with a new spring in my step. I finally felt like a big girl.

Until he didn’t text me for weeks.

I don’t know who’s more of an idiot: him or me. Throughout this whole stupid experience, I learned a few things. First and foremost: if you’re going to try anal, lube is a MUST. It would’ve been nice if my anal-loving sorority sister had mentioned that before. Secondly: anal won’t buy you love.

You’ll just be left wanting more.

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