My First Time Having Anal Sex

Dec 20, 2023
Julieta Chiara First Time Anal

Sexual exploration came to me naturally, even at a super young age. Losing my virginity at 14, and getting into a long term relationship by 15, I wanted to try it all. 

If there's anything I miss about those first relationships, it’s just how “new” everything is to you. You have an urge to try it all, to explore it all. It’s the sweet moments of nervously asking a partner for something new, or confronting feelings that aren’t so comfy. 

To me, anal was one of those. I was almost 17 around this time, and had been with my current boyfriend for around 2 years. He was in college, and yes I was still in high school (save the shame game, I really don’t care that I was this young lol).

Our sexual chemistry was out of control- we would fuck everywhere. His parents house, mine, his car, outdoors, on a hike, literally everywhere. He even bought my my first vibrator, which I remember nervously hiding in my bedroom even though my parents didn’t care.

"I want to try anal"

In our topics of conversation, he brought up how he was super into the idea of anal. He had seen it in porn (of course lol), and wanted to give it a try with me. I’m not going to lie and act like I was 100% down for anal right off the get go.

In fact, I felt pretty threatened by it. Threatened in the sense that I was an impressionable 17 year old, one who used to definitely get threatened by other women or thinking I wasn’t enough. 

When he had brought up anal, my first thought was 1. Is what we currently have not good enough and 2. Am I behind or “failing” because others can do this and I haven’t?

We both used to have super porn filled Tumblrs, which only added to that fire since for about a week straight he would repost anal gifs and vids.

Lord, bless my young ass self for being so insecure for no fucking reason- It’s something new and fun. I can totally see why he brought it up, and I’m glad he did. 

I wasn't completely sure how I felt about anal. I mean, I hadn't ever felt or explored the action or idea. Many try anal because they want to satisfy their partners, but not me. I made it clear before trying anything with my ass that this was for me, and not to please him. Being perfectly happy with my vagina, it was a new horizon of pleasure I was soon to embark on.

Embarking on my first anal journey.

In a delicate combo of never having my ass touched before, and being incredibly shy at someone looking at my butthole, any form of anal stimulation was hard. In many ways, we had embarked on an anal mission- and I was determined to be able to do it.

After plenty of research, and exploring myself, I actually realized this would be way pleasurable for me too. I saw all the tips on fingers first, douching, lube, the works. 

When we started playing with fingers, I realized just what a journey we had ahead of us. The only way I can describe it is clenching up automatically. The ass is a muscle, the sphincter, and it’s powerful AF- The biggest hurdle in anal play is simply relaxing it.

With this feeling being so foreign and with my body rejecting it, I found the most success came from when I stimulated myself. 

I started by simply massaging the outside, getting comfortable with the sheer feeling of anything being near my ass. A great help became my vibrator that I would use on the outside, which helped in many ways “desensitize” my ass. Once accustomed to that after about a couple of weeks, I started playing with inserting fingers. 

Anal practice? So much.

My boyfriend’s fingers were fucking huge, so my own were a better option to begin with. This required a bit more patience on my end, learning how to relax my body and not clench my sphincter.

At first, it was incredibly uncomfortable- I’ll be super honest, the insertion process can be a bit ironic. When you aren’t used to anal stimulation or relaxing your ass, the insertion honestly feels like you’re about to go to the bathroom.

Many folks never fully try anal penetration because they can’t get past this feeling that they might shit on themselves or their partner. It’s a completely normal feeling because well... what is the rectum intended for lol.

When you learn how to relax these muscles, it no longer feels like you’re about to head to the bathroom. When I was able to successfully play with my fingers and feel true pleasure from them, I knew it was time to.... attempt the penis. 

First Time Anal Penetration

Trying anal penetration with a penis was not a one time ordeal. It wasn’t that I prepped for months and then suddenly took dick like a champ. On the contrary, this process alone took another couple months: but I was super motivated to do so.

There’s a huge difference between fingers, pleasuring yourself, and then scaling up to a penis and the person moving that penis. While you usually fiddle around with your fingers, I’m sure your partner is looking to thrust. I wanted to experience that bliss, but it proved to be challenging. 

Our first try was a complete flop, and it was my fault. Taking the douching process super seriously, I bought an enema at the grocery store. What my dumb ass wasn’t educated enough for is the following: You’re supposed to douche with water, not the actual enema solution.

The solution basically makes you shit your brains out, and proves to be counter active to anything anally fun. I did the actual enema, and ended up spending 4 hours in my boyfriends college dorm room bathroom.

Hot right? Afterwards, it felt like my ass was on fire since it was a saline solution, so we left my ass alone for a couple of weeks. 

On second attempt, and proper douching, we were ready to fly. Tons of lube, fingers were gliding great, but the another problem came up: Position. I could not find a position where I would relax enough to even attempt taking my partner.

The head of my partner’s penis was incredibly painful. Let me tell you now: You do not know pain until you've experienced anal pain. It's an eye opening, searing pain that makes your eyes water. “Typical” positions like missionary or doggy were not helping me relax.

He had a typical sized penis, but the moment we tried inserting his tip it truly felt like some monster cock, and I was freaked out. Once again, I felt anally defeated. 

Anal mission isn't over!

None the less, we kept trying, and finally one fucking day: IT HAPPENED. This took so long, but if finally worked- I had to prep for LITERALLY 2 FUCKING HOURS. An award to my boyfriend at the time who anally stimulated me with tongue, toys, and fingers for two hours before I was actually able to take him.

Applying so much lube, we tried a different position which helped so much: Laying on my side in fetal position, with my top leg lifted up towards my face. This made it so my body was completely relaxed, but my ass was the star of the show and easily accessible. 

Practicing deep breathes, I would have him push slowly into me as I exhaled. This process alone may have taken 3-5 minutes, and he was so patient with me. Checking in constantly, I kept giving him the go ahead to keep going.


Once the tip of the head was in, the rest was unicorn magic. Suddenly my ass seemed to relax, and felt comfortably full. The first few thrusts weren’t painful, but they felt fucking INTENSE. It’s one of the most intense sensations I could ever describe. They take over your entire body, and you’re almost paralyzed from the mixture of pleasure and thrill. 

We went super slow to ensure my comfort, and stayed in the same position the whole time. Non the less, we were both stoked. 

Behold, your anal queen.

Getting that first time out of the way really changed the following encounters. Suddenly I felt much more relaxed, especially seeing how great it was for me too.

Anal is always way more sensational than vaginal sex, so there were plenty of times I actually preferred it. We probably had anal sex at least 4-5 times a month, and it really didn’t take me so much prep since I knew my body better at this point.

I found a rhythm to clean out, always had my lube, and the positions I loved and trusted. 

The future of anal


Breaking up with him, I went on to another relationship where anal sex also became really prevalent and frequent. It was thrilling, fun, and I’m certain the pleasure was just for me.

Even though it was a lengthy process for myself, I’m so glad I chose to explore it. My first time doing anal was a fucking journey, and I got to know my body like never before.

If there is anything you can gain from my story, it’s to please take your fucking time and don’t rush.