I Lost My Anal Virginity On A European Family Vacation


One very hungover Sunday morning, my boyfriend and I were watching a Youtube documentary. We were laying on the couch alternating getting water, throwing up, and whining, so when it ended both of us were far too lazy to get up. We decided to just let it skip to the next video and continued watching. The next thing that came on was a documentary about porn. In my pain, I froze, unsure what to do. I weighed my options and decided not change it, partly because I didn’t want to see like a prude, and partly because I knew if I got up there was no doubt I would hurl. In this documentary, everyone was very open and very, uh, free. Topics I had shied away from forever where the basic of the footage and sexual things I didn’t even know existed were highlighted. When the credits rolls and my boyfriend turned to me, I had a feeling what was coming. I mean, there are only so many times that the word ‘anal’ can be said before it starts a conversation.

At this point, my boyfriend and I had only been dating for five months and he seemed more than pleased with our “regular” sex life. As we talked about the documentary, I finally got up the nerve to ask the dreaded question,

“So, would you ever be, um…interested in doing anal?”

And to my surprise, I got the best possible answer, “Oh, no, I think it’s gross! Absolutely no interest!”

With that, my winner of a boyfriend kissed my forehead and handed my hungover ass a bag of Doritos. At that point, I thought that the conversation was over, my asshole was spared, and I officially had the best boyfriend ever.

Fast forward a few months and my boyfriend and I were both set to go on family vacations. Separate family vacations. While we both should have realized what fortunate brats we were to be toted around Europe, we were both focused on our three weeks apart — the longest we had both gone without seeing each other, and sex, since we had first met. One night after a steamy Skype conversation, a series of Snapchat pictures, and quite a few sexts, we ended up on the “what’s your fantasy” conversation. After I described something lame that I thought he would enjoy, he finally let confessed his: anal. I tried to hide my surprise.

“I thought you said that it grossed you out?” I sputtered, trying to hide my panic.

“No…I was just trying to keep you happy, I didn’t want to scare you off,” he admitted sheepishly. You know, the tale of a couple both trying to passively please each other by hiding what they like sexually. Classic.

The next day, I woke up to an eggplant emoji next to a peach emoji. Just the “good morning” text every girl dreams of. After a few messages sent back and forth I realized that he thought that us doing anal was now a done deal. Maybe it was because I missed him. Maybe it was because I thought that my virginity was growing back. Maybe it was because I anxiously thought that he would meet some sexy European girl and forget about me. But in truth, it was probably because he offered to meet me in Venice for a few days and pay for the hotel room. But after much trepidation and Googling, I agreed to give anal a try. When I met him a few days later, I greeted him like I hadn’t seen him in months. He greeted me like a horny guy who was about to get laid in a very special way. After walking around the city until sunset and being wined and dined (mostly wined), we retreated back to the hotel room.

The room itself wasn’t the five-star quality that I had dreamed of when I pictured losing my back door virginity. But since I was in the heart of the most romantic city in the world, fresh off a gondola ride, and full of authentic pizza, I decided to make an exception. The older, family-style furniture seemed endearing until I was lying on my stomach, squeezing the life out a pillow, staring at it. We had previously gone to a local pharmacy to pick up some lube (thanks for the advice, Google), and after an excruciating, language prohibiting conversation with the pharmacist, we were able to finally get some. Fun fact — in Venice, they keep the lube behind the counter, which proves for a fun conversation.

After he used nearly half the bottle of lube, “relaxed” me with a back rub, and consistently told me how beautiful I was, it was finally in. Ten minutes later, it was over. While I didn’t hate it, I would definitely need some Italian air and wine to do it again.

So what it all comes down to is this: if your boyfriend ever tells you that he thinks anal is “gross,” don’t believe him. And if you do decided to have anal, do it in Europe. At least they have bidets over there.

Image via Shutterstock

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Hiding from my mother and standards, both of whom would disown me if they heard most of these stories. Aspiring law school student, with a chihuahua named Bruiser and a head of unnatural blonde hair. Email me your "crazy" stories or any mixed drink recipes that taste like juice, but have copious amounts of vodka in them at [email protected] Watch the bitch behind these stories at:

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