Q&A - Anal Sex

<Redacted> asks: "I want to fuck my girlfriend in the ass, but she had a bad anal experience with an ex boyfriend of hers (like so many women) and thinks she's turned off from it forever. How can she get comfortable having anal sex again?"


This definitely happened to me. I tried anal sex for the first time when I was fifteen years old with my first boyfriend. I let him do all the research on how to go about it and then we tried it together -- he managed to wiggle his way inside, but after that it just felt like pooping. Pretty awful. I thought I'd never do it again.

Speed up to five years later (now), and I freaking love anal sex!  I can usually get pounded as hard and as fast as in most porn. I even think that after all this time, I'm finally ready for DP (which will happen in January!)

So how did I get to this point?

 Well with my first ever boyfriend, we tried it a few times. We did everything right (so we thought). We used lots of lube, did some finger-play first, and then he moved his penis very, very slowly in until I was quite relaxed. Because of that, it didn't really hurt so much, but it felt super gross. After maybe three attempts, we gave it up forever.

So then two years later, when I was 17, I started having wet dreams about getting fucked in the ass. It has been the only time that I have ever experienced a wet dream (though I would wake up right before the orgasm). I started to crave anal sex and became immensely turned on at the thought of it. Eventually I couldn't even orgasm watching porn unless the porn featured anal sex. 

So finally one night... I asked my at-the-time boyfriend to try it with me. Right before he was about to insert...I chickened out. We had vaginal instead.

Weeks or maybe months later, we were sleeping... then, like so many nights, he woke up in the middle of the night with a raging sex drive and started touching me to wake me up. (Yes, I lived with my at-the-time boyfriend when I was 17.) 

He told me he wanted to fuck me in the ass, and I said, in my near slumber, that he could. I laid on my stomach touching my clitoris while he moved in and out of my vagina, making me incredibly wet. He kept pulling out, rubbing his dick over my asshole, spreading the wetness. Finally, he just started to push in a bit. We didn't use any lube (though lots of saliva) or any fingerplay, and it hurt a bit. He got maybe an inch inside, and that's all I could handle. I vigorously masturbated myself while he moved ridiculously slowly in and out of that one inch of my asshole. It was painful but felt unbelievably good while I touched myself. I experienced one of the most intense clitoral orgasms of my life. 

The novelty of being an inch in my ass was enough to make him come moments later. 

So then we started doing late night anal fucking once every few weeks. We did it the same every time -- I'd lay on my stomach and stimulate my clitoris, and he'd push himself in just a tiny amount at a time. We slowly worked with each other to let him in a little more each time. Finally after a year, he was able to push his entire self inside me. However, he still couldn't move quickly at all because it hurt too much. 

After another year of this, he was able to move in and out a little bit faster. Eventually he was able to push all the way in and pull all the way out within two seconds. That's the fastest he and I ever got.

After a three year relationship, we finally broke up.

Then I moved on! Seeing as that guy was only the third person I ever had sex with, and that I didn't see another penis the whole time I dated him, I didn't realize how huge he was. He was actually quite larger than average. 

The next person I had sex with was just about average in length and thickness. I told that guy he could fuck me in the ass -- and he took the full liberty of doing so without taking any precautions except using lube. He fucked me hard and fast, and my ass was able to take it! I think it was because of his size that it was so easy for me! Years of warming up with a huge penis helped this guy really have a fantastic time with my ass. 

After that, I started fingering my ass regularly. I started using toys (or... fresh produce) to work on relaxing myself. I always did this in front of a partner to make it a whole sexy event. 

I've asked almost every partner I've had since if they like or are interested in anal sex. Almost all of them say yes, so I get to try it out with everybody. If they're really large, we just start out slow and use a lot of saliva or lube. 

The fact that I've been so mentally comfortable with the strange idea of letting people put their penises inside my butthole I think was a huge part of the battle. After I just mentally became comfortable with letting them inside me, my body became more relaxed and it became easier.

And finally now I can take all sizes that I've seen in person, and I can take them as fast and as hard as they want to go (with some rare days as exceptions).

So to conclude, here are my key pieces of advice:

1. Don't get discouraged if it doesn't feel good or if it hurts at first. Keep trying, and try different techniques and positions.
2. Work on playing with your anus without a penis entering it. Use your fingers or toys.
3. When you put a penis in your anus, don't push it in to the point of it hurting. Go VERY slowly.
4. Touch your clitoris or finger yourself! Even if it hurts your anus, it will intensify greatly any stimulation elsewhere!
5. Use lots of lube or saliva (I really always prefer saliva over lube).
6. And again... keep trying! It has taken me five years to get to this point -- persevere!