Background:
I have been obsessed with anal for as long as I can remember. The first porn I ever watched with anal was a VHS copy of "Debbie does dallas" that I snuck from my dad's stash when I was about 14, I was blown away (pun intended). I'd say about 90% of the porn I watch is anal related and although I do enjoy vaginal sex I fucking love anal! It's so hot and dirty that I just can't help myself.
Here is my story:
My girlfriend and I were teenagers when we lost our virginity to each other after being together for about 5 months. With the milestone of our virginity gone I was eager to take things to the next step and finally try anal. Problem was I really didn't know how to approach it. We really never spoke about it except in passing one day but really discussing other people, regardless of who we were talking about the sheer thought about discussing it was a massive turn on. I didn't even speak openly about it with my close friends and it felt a bit like too taboo and a hidden desire.
Flash forward a couple months, as much sex, blowjobs, 69's we could have we did. Spring break was here and we were enjoying our freedom from highschool. One day we decided to hang out with another couple and drink a bottle of Southern Comfort that I stole from the restaurant I worked at. We're all having a good time in my buddy's basement playing video games and taking shots and sipping on some mixed drinks when the mood kicks in for our friends and they decide to take it upstairs. As my buddy leaves he casually jokes and says "try not to have sex on my couch" lol. So as our instinct and the alcohol kick in we start making out and heavily caressing each other. I unzip my girlfriends pants and start grabbing her voluptuous ass. By this time my beer confidence is starting to take over and I inch my way closer and close to her asshole. I was a bit apprehensive at first but figured if I had once chance this was IT. So I inch my had in a bit closer and start rubbing her asshole. To my surprise she didn't recoil in disgust and I kept going, getting hotter by the minute. At this time she is sitting on top of me on the couch with her pants and thong at her knees. I pull off my pants and let her rub my semi hard cock as I move her ass closer. At this point my heart is racing and im thinking to myself holy fuck this is really gonna happen I am really going to fuck my girlfriend in the ass! The only downfall was the alcohol in my system I was for all intensive purposes "to drunk to fuck". After a few attempts of sliding my cock into my girlfriends ass we both gave up because my cock wasn't hard enough and we had absolutely no lube.
I was a bit disappointed at this point but didn't give up! Later that same night we headed back to my place and picked up where we left off. Still a bit intoxicated and the beer confidence slowing but dwindling I decided to make another attempt. After a bit of foreplay and eating her juicy wet pussy I quickly began rub her asshole again. Still no knee jerk reaction or a slap in the face so I keep going. I proceed to flip her over onto her stomach, she is still wearing her babydoll but no pants and her orange g-string is on the floor. I lube up my fingers with saliva and start slowing fingering her asshole. At last the time has come I pull my finger out of her ass, spead her cheeks and stare at her asshole which I am about the fuck.
I'm now close to sober and my cock is rock fucking hard. With no lube in sight I grab as much pussy juice as saliva as I can to lube up my cock for her tight asshole. I open her legs while she lays on her stomach a get ready to fuck her in the ass. I struggled to get the head of my cock inside her so in my frustration I devised a plan to use 2 fingers to finger her ass and work my cock in place of my fingers. Finally with enough saliva I slide the tip on my cock in her ass. Now passed the threshold I take my time slowly sliding my cock in and out of her tight ass for every thrust I slide a little bit deeper until I am balls deep. I don't recall exactly how I felt but I think a bit of euphoria came over me. My thoughts focused solely on once thing "Oh my fucking god this is so fucking hot and feels better they I could have imagined". I lasted as long as I could watching my swollen cock be swallowed by that juicy white bubble butt before I came deep inside her ass.
After it was all over I slowly pulled my cock out of her ass as it dripped my load of cum down to her freshly shaved pussy. I got up to get her a towel to clean up then laid down for a minutes basking in the glory and thinking to myself "I just fucked my girlfriend in the ass…". We didn't speak about what just happened until a day or two later. She told me she was caught a bit off guard given that I never expressed the desire to try it. Needless to say she wasn't that into it but still let me fuck, lick and finger her ass 3-4 times a week until we broke up. Apparently she always had an attraction to women and started dating women right after we broke up. She may have been overcompensating during the time we dated, but fuckin a' she didn't mind sucking my cock and swallowing the load I just blew in her mouth.
Since then I have only had anal sex with one other girl – my now wife. She doesn't care for it much but let's me fuck that ass every once in a while. When in the mood she loves when I play with her ass and when I taste it too.
Source: reddit.com/r/sexystories/comments/3adcai/first_time_anal_mf