First Anal Sex

Since I first learned about sex I knew I would turn out to be a kinky sumbitch. Like most horny young lads I craved the day when life would present me with pussy. But my first kink was anal sex. I became obsessed with anal sex. The thought of sliding my cock into a woman’s ass became an obsession to me. I had come close on a few occasions but no cigar.

My second gf in high school really wanted to try it albeit unsuccessfully. Both times we tried were in vain. She prepped and cleaned herself with an enema bag I had purchased ( with much embarrassment to my teenage self) and we had an industrial size bottle of baby oil. She was on the pill so there were no latex condoms that could be damaged by the oil. Despite our preparations her back door was too tight to receive my dick.

Another gf Maria (see Jamaican Goddess story) loved having her ass fingered and eaten but same problem. Too tight/too big. I’m not pornstar huge but I am bigger than average. Plus I’ve been blessed and cursed to have had relations with many women whose holes (cunt and ass) were ridiculously tight.

Fast forward to Amy. She was many things. A living breathing Barbie doll with an identical twin sister; an old mutual crush from high school and lastly my good buddy’s younger sister. My buddy was very protective off the twins and always told us to stay away from his sisters. Despite this we had a mutual crush on each other since second year of high school, which he did not appreciate. In fact he caught us making out at a New Year’s party in 1997 and absolutely lost it.

Fast forward to Y2K and a party I hosted at my house. Out of nowhere Amy showed up with a friend of mine and we made out again. This time her brother was living overseas so nothing could stop us. We began dating and within a week we were fucking like rabbits. Another bonus was that Amy was on birth control so we never once needed to use dreaded condoms.

Our sex life was pretty good but I wanted to fuck Amy in the ass. She was somewhat receptive but always joked maybe on my 30th birthday. It became a running joke until one day I told her I couldn’t wait 4 years. She winked and said maybe it will happen sooner. I could only hope she was serious.

The honeymoon phase lasted about 3 months and we got into our first big argument. Even though it was trivial she stormed out got in her car and left. After a half hour I was still fuming and wanted to finish the argument. I called her cell and told her to get her ass back to my house. Instead of telling me to fuck off she knocked on my door an hour later.

No argument ensued no words were spoken. We dove right into the nastiest makeup sex I’ve ever had. I shoved my cock down Amy’s throat and basically skullfucked her until her eyes teared up and she was a wet  sloppy mess. I threw her on the couch and rammed my cock into her cunt as hard and fast as I could. After she came for the third time she said she needed a break. I was not having it.

I pulled her on top of me in 69 position and dove my face into her wet pussy as she licked and sucked her juices from my cock. Without warning or asking I began to lick and tongue her asshole. She went wild and started cumming nonstop. I pushed my luck and stuck my finger in her ass and she had one of her strongest orgasms ever.

As Amy begged to recover I told her I wanted to fuck her ass. She simply smiled and asked if I had any lube. Five minutes later I found an old tube in the back of my drawer and bent her over the back of the couch. I applied the lube threefold. Coated a finger with it then my cock. After fingering her ass for a few minutes I inserted the tip of the lube into her hole and squeezed a generous amount up her rectum.

Getting behind her I slowly sank my big cock into her asshole. The feeling was indescribable and I was afraid to cum too soon so I just held her against me and relished the feeling of the first woman’s asshole engulfing my cock.

Once I had regained my self-control I started to fuck Amy’s ass. She was tight even with all the lube and precum that was inside her. It was when I grabbed her ponytail that she started screaming, ‘Fuck my ass!!!!’  at the top of her lungs. I reached around and began to play with her clit but she pulled my hand away and plunged two fingers into her dripping cunt. 

Amy must have cum four or five times with her holes plugged tight until she begged me to cum on her tits. I pulled out, got her on her knees and stroked my rock-hard cock until I came all over her tits and face. Best makeup sex ever.