I've been reading all these great stories and wanted to add my own true story.
I was a somewhat late bloomer and didn't have my first GF until late in college. We were both virgins and the sex was pretty good, at least I thought it was for two people with zero experience. I had always been interested in anal sex and would occasionally ask but never got anywhere, not even a finger in her butt.
We were coming up on a year into our relationship and the week before our anniversary, we were hanging out in her apartment and having a some afternoon sex. Out of the blue, she asks me if I want to put it in her butt, as a sort of early anniversary present. Of course I said yes and my cock was super stiff at this point. We went back to her room and she started off with a nice wet blowjob. She wasn't a fan of receiving oral (never really understood this) so it was straight to pussy for some fucking in missionary. After we both got worked up, she turned around and got on all fours with her butt in the air. She asked if I was ready and the only confirmation she needed was seeing how hard my dick was. I couldn't believe this was going to happen, I just nodded yes.
She grabbed some lube that she had on the bedside table and slathered my cock to make it super slick. This was such a long time ago that I don't remember if she put any lube on her butt. The thing that really stands out in my mind and I will never forget is how easily my cock slipped into her butt. At the time, I had no idea if she did any prep before but in hindsight, I'm pretty sure she did. The reason this stands out so much is because when we had sex for the very first time, her pussy was so tight and not lubricated enough that we didn't actually end up getting my dick inside her. We actually did not end up having sex for the first time until two nights and two tries later.
Once I was in her butt and I got over the shock of how easy this was, I slowly started pumping in and out of her tight ass. I checked with her to see if she was ok and she nodded yes. The view was great, I loved see her ass gripping my cock and the tightness was incredible. I'm not big, only 5.5 inches, so I was able to get balls deep into her ass and just hold it there for awhile. I wish it could have lasted forever but in reality, it was probably no more than 5 minutes. Near the end I couldn't hold back anymore and asked her if I could come inside her ass. After a few more pumps, I shot my load deep in her butt and slowly pulled out. She quickly got up and ran to the bathroom to clean up the cum leaking out of her ass. This was an awesome anniversary present!
Sadly we only had anal sex one more time after that, I was able to convince her to let me cum inside her ass because we didn't have a condom, and we broke up a few months later.
I am thankful for her showing me how awesome anal sex can be and it's only fueled my passion for butt sex with future partners. My next GF was also a virgin and didn't want to give up the pussy but was more than willing to let me fuck her ass instead to keep her "virgin" status.
Source: reddit.com/r/gonewildstories/comments/3row3b/my_first_anal_experience_and_definitely_not_my
Ha! That do-me-in-the-butt-instead girls. I will always have a special place in my heart for those ones.
The good ole "Poop hole loop hole"
She was a bit of an odd duck – master of the "toothy" BJ (did not like this at all), she lived in a house with her brother but the entire time we dated, I never met or saw him even though we were having sex with literally just a wall separating us. But I never had more anal than I ever had in my life, maybe I’ll post stories about our hook ups later.
I’ve always wanted to try anal but keep backing out! Great read!
Back it in the backdoor, it’s amazing!
Ha yes do type more, good read.