My First Time Anal Sex Experience: Our Author Tells All

For so many years our author had gotten by with average sex. The only penetration from a penis she had experienced was vaginal – no clitoral stimulation, no toys and most definitely no anal sex. It was only once she had a new partner, a new level of comfort and new self-confidence that she discovered a new way of enjoying sex…and it was her first time having anal sex!

So. First things first. No, I don’t only have anal sex now. After my first time anal sex attempt, I now enjoy being anally stimulated every now and then. Furthermore, enjoying it as a “taboo” from time to time really turns me on. Nevertheless, close, intimate vaginal sex with my boyfriend is still my preferred type of sex. A friend of mine sees it very differently though. She’s even trying anal sex with one-night stands, which is unimaginable to me. This is because, for me, anal sex needs one thing above all: trust.

My first time anal sex attempt? Terrible!

My need for trust is probably due to the fact my first time anal play was terrible! At the time I had no trust in my boyfriend and he was too rough. Above all, we weren’t prepared. And believe me, you NEED to know how to prepare for first time anal. It is important to start everything by discussing your desires and wishes together, as well as having enough lubricant and a condom on hand. Finally, it can also depend on how long you and your partner have been together or if you have a few partners. If you aren’t prepared and you don’t look after each other, it can be a really painful affair. As was the case with me. I had to stop straight away because my partner was too pushy and didn’t use any lubricant. After that, we only had vaginal sex as I didn’t want to try anal with him again, which in turn frustrated him further…

“But then I met my current partner, who was a totally different type of person.”

To his core my boyfriend is sensitive, open and a great communicator. So after a few months of being together and enjoying wonderful sex, he let me know that he wanted to try anal sex with me. He explained to me that it was a huge turn on for him it is. And I understood. Even when we were only talking about it, I was turned on – and curious. Still it took a few more days until we had anal sex for the first time.

How to do anal for the first time: a little wine and a lot of lube

It was a Friday night when we came home from a party and were a bit tipsy, if not drunk. In retrospect, having a little alcohol in my bloodstream was helpful when trying anal for the first time. At least that was the case for me, because I was especially relaxed that night. That is actually an important requirement for anal sex. When your mind isn’t calm, your whole body will feel tighter. This includes the already tight sphincter muscle, which can pull together and make penetration painful. So we were tipsy, in the right mood and feeling into each other. We first jumped quickly into the shower, which is especially recommended for first time anal sex as it creates a more comfortable atmosphere. We warmed things up again under the water and then climbed into bed with the lubricant. Slowly, slowly my boyfriend entered me from behind.

“As the penetration continued, I began to get used to this pressure – and even began to enjoy it!”

The unfamiliar sensation felt a little strange, almost as if I had to go to the bathroom. But I didn’t, I knew that for sure. By the way, this is also an important tip: only have anal sex after you’ve been to the bathroom. Otherwise, it can get a little “dirty.”

As the penetration continued, I began to get used to this pressure – and even began to enjoy it. Also, my sphincter had widened and my boyfriend could move faster. What really turned me on was the fact that my boyfriend was so hard. And apparently really enjoying himself – it only took a few minutes for him to come. Then came another unfamiliar feeling. I’ve never had semen in my rectum before. Another tip: even if it isn’t very romantic, go straight to the bathroom and clean yourself up so you don’t make any more mess on the bed.

My first time having anal sex with my current partner was definitely not the last time. These days, we have anal sex every now and then if we feel like it. The only thing I haven’t experienced yet is an anal orgasm (yes, that exists!). But we have all the time in the world to try… and in case you want to be more experimentive check out our vibrating anal plugs.