Escapades of an Anal-holic

After spending so much time reading the stories of other people talking about assfucking, I decided to write my own. All of what you are about to read is true, only the names have been changed to protect the innocent. Dummmm, Dee, Dum. Dummmm, Dee, Dum, Dum, Dummmmmmmmm.

I love anal. I get an incredible rush out of pushing my cock into a woman’s beautiful asshole. But, it wasn’t always that way. First, a little about myself. My name is John. I am a 45 year old African-America male, 6’3”, 195 pounds, chocolate complected skin, clean-shaven head with a moustache. I have an 8 ½ inch thick uncircumcised cock.

I was born in the south, where we are taught early to respect women and girls. I had quite a few girlfriends growing up and was exposed to sex at a very early age. Five years old to be exact. I was raised by a single mother with my other siblings, 2 brothers and 2 sisters. I was the second oldest.

My family was and is very closed knit, even today. I lived in the typical extended-family household of that day. It was a big house my grandparents owned in the country. My grandfather died before I was born and my grandmother moved to the closest town to us. My oldest aunt and her husband lived with us. My other aunts would always visit since they lived in town, too. They had teenage sons. My Aunt Vivian’s sons were Billy and J.W. My Aunt Ida’s son was named James. They would baby-sit us when my mother and aunts went out.

These cousins were more like older brothers and they are the people who provided my early sex education. They were my heroes. They always had girls over to the house. They would send my sisters and youngest brother next door to play with the neighbor’s kids and ask my older brother and I to keep watch for the adults.

Afterwards they would tell us what happened and what we should do with girls when we get them. Quite often, J.W. would tell me to sit in the closet and watch while he fucked some of the girls. He would position them around so I could see his cock going in and out of their tight young pussies. So by five, I knew exactly how to fuck.

Back then, in the Black community; homosexuality, oral sex, anal sex, and anything not involving just plain pussy fucking were taboo. So I grew up knowing only how to fuck pussy. My cousins said “Never put your mouth on that nasty pussy”. Because of that I grew up not having oral sex of any kind. The Reciprocity Theory (will explain that later) as I called it impacted my sex life.

I fucked a lot of girls before graduation. Even fucked this little white girl named Vickie, who was about the biggest slut in town and really loved Brothers. Then at the tender age of 17, I left home to join the U.S. Air Force. In technical School at Keesler AFB in Mississippi, I met women from all over the country. And a lot of young, liberal minded white women.

That’s where I met Laura. She was a beautiful, older (19), sexy and progressive white girl from upstate New York. She had been to college and had lived with this older Black guy in her hometown. With this immediate attraction, we started dating. We were hardly ever apart, and most of the time was spent just fucking. We would spend the entire weekend, starting Friday evening until late Sunday night, just fucking. I was a “real machine” back then. We had great sex, nothing kinky, nothing taboo.

Occasionally, Laura would ask if I wanted her to suck my cock. She said it was so beautiful she just wanted to please me. I would tell her no, that I wasn’t into that. Eventually she told me she really wanted to suck my dick and that she enjoyed it. That’s when my Reciprocity Theory was developed: "The idea was if she did it for me, then I would have to do it for her." Being the Southern Gentleman I am and remembering what my cousins told me, I politely declined.

After a few months together, Laura told me that she really enjoyed sucking dick, needed to suck dick and if I didn’t want her to suck mine, we should break up so she could suck someone else’s cock. STUPID ME! I said ok, we will have to break up then. Later I would see this guy she started dating, and he would look at me like he really wanted to thank me or something.

So after our breakup, I started my First Crusade: To fuck as many women as possible. Later down the road I got my first blowjob. I could kick my own ass. Laura’s new guy must have thought I was the stupidest motherfucker in the world, I know I did now.

But life was good for me. Fucking a different girl almost every night. I even fucked 3 girls (at different times) in one night. I didn’t just fuck women, I made them fall in love with me. I tried to give them the type of fucking they never had before.

On one visit home for leave, my cousin J.W. told me about his time in Germany and how much German women loved ass fucking. I told him he must have been fucked up in the head or turning gay, fucking a girl up the ass when all that pussy was there. He just told me not to knock it until I tried it.

Back at Keesler, there was the friendly competition between me and some of my "Boys" on who could fuck the most women. Of course when we got together, we would tell tales our sexual escapades.

We were at the gym one day waiting for next up, when one friend Skip, told us about his time with this beautiful sister from Chicago named Andrea. Skip was from Chi-town too. Andrea was hot, hot, hot. She drove a little green Triumph TR-7 convertible.

Skip said he was fucking her one night, she was on top riding him good. He said her pussy was extremely wet and hot. He said she grabbed his dick and pulled up and his dick came out then she pushed down again. He said here pussy got really tight and kind of dry. She pumped up and down on his cock a few time and she came. Then she grabbed his cock again, pulled up and his dick came out, then she put it back in and her pussy was wet and loose again. He then knew she had him fuck her in the ass.

That story got me so hot. I even missed some shots I could easily make because I was thinking about Skip’s story. After the gym, all sweaty from b-balling, I went straight to this girl’s room in the ladies dormitory, to fuck her. Michelle was a cute little white girl with acne who worked in the dental clinic on base that I had been fucking for a while.

I was in there tearing that pussy up when I asked if she had ever been fucked in her ass before. She said she tried once but it hurt and never tried again. I told her I wanted to fuck her and she told me she was scared. I got some lotion (Jergens in the white bottle with black label) she had in her nightstand that we usually used when her pussy got dry from me fucking her.

As I said before, I was a “machine” back then. I started fucking her pussy again in the missionary position. I squeezed some lotion in my hand and applied it to her asshole. I reached around and rubbed a lot of it all around and slid my middle finger into her asshole. She grunted and moaned but accepted my finger without complaint.

After really tearing that pussy up and fucking her ass with another added finger, I then turned her over doggy-style. I continued to fuck her and started fingering her asshole again when I asked if she was ready. Michelle said she was afraid because I was so big. But I knew she was lying. She liked me to fuck her really hard and hurt her pussy. She used to cum really hard when I pounded the back of her pussy. So I thought she really was looking forward to the pain and was saying no like, “oh no, please don’t fuck me with that delicious big black cock in my little white nearly virgin asshole” because she wanted it and thought her role-playing would turn me on. Which it did.

I pulled out of her pussy and pumped a couple of dollops of lotion in my hand and greased up my cock. Her asshole was already lubed up and ready. I told her to reach back and spread her cheeks as I put the tip of my cock to her asshole. Michelle pleaded, “Baby, don’t hurt me. Please go slow”. I asked if she loved me. She said yes. I knew she would. All my bitches said that when I fucked them. But I had never fucked any of them in the ass before.

I slowly pushed into her ass. It did not respond at first, so I pushed harder. Then it happened. Her asshole started to open up and accept my cock. First the head slipped in as I saw her asshole stretch around the crown. Michelle moaned and grunted as she pounded her fist into the bed. She had her face buried in a pillow, which she was now biting into to muffle her cries.

I stopped pushing to let her adjust to my cock and let the pain subside. I asked I she could continue. She said she wasn’t sure, that it hurt really bad. I told her if she ever wanted me to fuck her again, she had better take my cock in her ass. I told her to rub her clit to help ease the pain away, which she did. I asked if she wanted to continue. She said she wanted to please me and that it felt better. I started to work more of my cock into her. As I moved forward, she would move forward. So I grabbed her hips and pulled her back to me while I slowly fed her my cock.

Finally I was all the way in. I rubbed her clit with my right hand and squeezed her left nipple really hard with my left hand. Then she came harder than she ever came with me before. She screamed so loud that even with the pillow, I am sure the other girls in the dorm heard her. As I said before, Michelle was a freak, she liked pain. She liked it when I pinched and chewed on her nipples or fucked her pussy so hard she had problems walking. She would always come back for more. I didn’t know it at the time, but Michelle’s masochistic desires would have an impact on my future.

But now I was in her asshole. I waited until she adjusted to the fit before I started pumping my dick into her. I started slow and got faster and faster. Pretty soon I was fucking her with so much force and speed that I could not believe that she was handling it. At one point, my cock came out of her asshole and slammed into her pussy for a couple of strokes before I realized it was not in her asshole and was able to get it back in.

She was screaming into the pillow as wave after wave of intense pleasure hit her. And with her asshole pulsating around my cock, it was too surreal. I was and still am pretty good at holding back my orgasms and not cumming too quickly. But with Michelle cumming the way she was, and as hard as she was, I could not continue at the pace I was going. Finally I blasted hot streams of cum into her hot welcoming bowels, filling it up her anal cavity. She came again from my cumming in her.

After cumming, I continued to fuck her asshole squeezing my cum out past the rim of her previously tight asshole. When I finally slowed down, and she stopped cumming, I pulled my cock out with a plop and cum oozed out of her gaped asshole. It was so amazing. J.W. was right. Skip was right. Assfucking was really something.

Michelle finally came down from her euphoric high and told me how incredible it was and that she was looking forward to doing it again. She said she had never cum so hard or so long before from pussy fucking. I fucked Michelle’s asshole everytime we got together after that and we both enjoyed it. Now I was a convert. And she was a convert, too. And this was the start of my Second Crusade: To assfuck as many women as possible. And the adventures began…