The word ‘anal” has a few different meanings but even just the word alone is enough to make my ass cheeks clench together super tight.

From the moment I even heard about anal sex in elementary school, I know that sh*t wasn’t for me. I remember thinking, “Why would someone want to stick their dick where boo boo comes out?” Gross! But at the age of 12, everything was disgusting, including the thought of sucking a dick, but I damn sure got over that!

I was blessed that in all of my 25 years that no one had even suggested anal sex. I was more than ready to shut them down with a simple and succinct, “No.” But at 25, I began sleeping with a man more than 12 years my senior and needless to say, he turned me all the way out. I had only been involved with men my age or a handful of years older, until him. This man had stamina like you wouldn’t believe. Most of the men I had been with couldn’t keep up with me, but I couldn’t keep up with him!

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Not to mention that he had a high-powered position, pushed a Range Rover and lived in downtown Chicago. I thought this was the come up. I was down for whatever with this guy. He was a good for G.M.O.s–Guaranteed Multiple Orgasms, so it was only a few weeks into our smash sessions when he brought up anal.

My insides were screaming “Nooooooo!” I told him that I had never done it. He did like most guys do when they’re trying to convince you to do something new sexually: he tried to make a case for it. I told him I’d think about it.

After three weeks of nagging, I finally agreed. He wanted me to buy an anal toy to prepare myself. I didn’t do that because what can really prepare you for something like that? He came over to the my apartment ready with a box of magnums (he definitely needed those) and lube.

I assumed the position and he tried to fit his 9 inches inside my pea-sized hole. The pain that shot up my ass was something that I had never experienced. Even losing my virginity wasn’t as painful as the moment he attempted to put his dick in my ass.

“Ahhhhhhhhhhhhhhh,” I screamed in horror.

In a flash, I went from being on the bed to being halfway on the ceiling.

“Relax, relax,” he said.

I attempted to calm down. I knew I had to relax if I was seriously going to go through with it. He tried to push it in again. At that very moment, I knew I had f*cked up. That was pain that I had never experienced in my life. Sex is supposed to be pleasurable and this was the most painful thing that I had willingly put myself through.

“Stop. I’m not doing this sh*t,” I said.

He laughed, “What do you mean?”

“That’s it. I’m done,” I told him.

“Oh come on. It’s going to hurt the first time, but it gets better,” he pleaded.

“No, I know it won’t get better because I’m not doing this sh*t.” He laughed. He was cool about it. After the sharp pain in my ass subsided, we went back to our regular session.

After he left, I called my girl, who had successfully had anal sex, and told her about my experience. She laughed hysterically and said, “Girl, you can’t have anal sex with a man with a big dick. It has to be smaller.”

“But why would you be involved with a guy who didn’t have big dick?” I asked. I didn’t believe her because as far as I was concerned, a dick in the ass was a dick in the ass no matter what size. A few months later, he tried to be bring up trying anal sex but I shut that down with one look.

Maybe other people have had better experiences but I know that I’m not trying that sh*t ever again. Ever.

Are you into anal? What were your experiences with it? Sound off in the comments below.


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