My First Time Anal Although I Never Thought I Would Like It So Much

I am not sure in which category I should put this, so I will put it here.

I was 18 years old and until then I was absolutely 100% sure, certain, convinced and determined not to have anal sex, ever. With my best girlfriend I talked about this subject before and we both thought it was gross, probably felt extremely painful and is exists only to please men. Regular girls like us would never do something like this. We did see this sexual act in porn magazines and we were both grossed out by it. On a side note, ever since I was maybe 15 or so I regularly fingered my butthole while masturbating. It was just with selfplay and just to spice things up for myself. That could be kinda hot, if I was in the mood for that.

When I was 18 I already was in a 1+ year committed relationship with my boyfriend who was just a few months older than me. I loved him very much and we were compatible in many ways. The sex was wonderful as well, open and honest, always with total respect for each other. One night, while performing oral on me, he suddenly gave my butthole a little lick. I immediately responded with a moan as I found that sensation very interesting! Fed by my response he continued to lick me there and after a while slid his index finger in my butt and slowly fingered me there, while he now focused on my clitoris. Within minutes I reached an intense orgasm while he still had his index finger down there.

We had regular vaginal sex right after that and it felt awesome as I just came really hard. Afterwards he was kinda shy but still spoke his mind, if I would be okay that we try anal penetrative sex at least once. He promised he would be super careful with me. The thought now suddenly did not turn me off but sounded somewhat like 'hmmm, maybe?' The following days I gave it some more thought as I thought it still could be super painful. A penis is bigger than a finger. But I don't want to be seen like a dirty girl. Should I? Maybe just give it a try?

I discussed this with my best girlfriend. She was blushing and admitted she and her boyfriend already tried it! What the fuck? She said she was too afraid to admit it to me. We both laughed about it. They only tried it a couple of times and it wasn't as horrible as she first thought it would be. I was very surprised with the fact that she already had anal sex. But hearing her response was now also another pro for me to maybe try it as well.

While talking with my boyfriend on the phone I told him that we could maybe try it this weekend, but I told him to go super super careful on me. When the weekend finally arrived and we were in his bedroom when his parents weren't home we got naked and did our foreplay which was always a turnon to me. He then whispered that he bought lubricant. My heart started racing and I knew I definitely wanted to try this, at least try, maybe more. We discussed positions and were totally clueless. He then suggested that maybe I can be on the edge of the bed with my legs pulled up high (which I always love to do), so he can see both openings clearly, to see what he was doing. I agreed.

Nervous as hell I layed back, spread my legs and pulled them up. He also did this often with regular sex, so he could have a good look at my pussy. But now it was for him to look at my butthole. He kneeled down in front of the bed and started to lick my butthole again. Then he took the lubricant and fingerfucked my ass for a while, using his index finger. I was totally turned on. He switched from his index finger to his middle finger and now tried to slide those two fingers inside. After a while it worked and he gently, super gently used those two fingers. After a bit I moaned "try it with your dick now".

I looked up and I saw him lubing up his fully erect penis. He came closer to the bed and tried aiming it at my butthole. Since everything was very slippery, the first 4-5 attempts all ended up in my pussy. It didn't seem that easy to put it in my butthole since those holes are so close to each other. After some more tries the tip of his penis finally ended up in the opening of my butt. Ok, I immediately felt this was bigger than the 1-2 fingers from before. He was super sweet and kept checking me if it was okay, and that he didn't want to hurt me. OK, the tip was in completely and he tried to go further. That felt slightly weird and just a bit, just a bit painful, not too much. I told him to use more lube, so he pulled back and lubed it all up even more. And with the next attempt he slid his tip and a good part of his penis inside. I moaned and switched up "Auh!" with "Oh!" as it was slightly painful but with every move it felt better and better.

I closed my eyes and I almost could not believe I was being assfucked! A thing that I promised myself not to ever do. I felt dirty, I felt hot, and yes, I was even somewhat enjoying it. I moaned to my boyfriend how it was and he said it was hot, amazing and tight. He was not rough but he sure was penetrating my virgin ass in a pretty good way.

He always had quite good stamina but after not too long he orgasmed deep inside my tight little wrong hole. All in all I can say that my first time anal was pretty good. No horror, no extreme pain and definitely something worth trying again. And with that very same boyfriend we did it quite regularly. I'd say maybe 3-4 times a month, all depending on the mood. And the older I got (after we broke up) I enjoyed it more and more, with different boyfriends and now still with my husband. We do it on a regular.