• Julieta Chiara

First Time Anal Sex: My story time


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.