Becoming an Anal Sex Whore

“So, what made you decide to post your ad online tonight?” he asked as we walked down the hall of my apartment building.

“I don’t know,” I replied. “I guess I am just really horny and wanted to try something new.”

I knew, though, why I decided to post the ad that read “28 year old male looking to have sex with a man for the first time. Please, be open to fucking and being fucked.” I have been playing around with anal play since my senior year of high school.

I skipped school one day and decided to check my sister’s room to see if she had any porn. In the back of her closet I found two dildos. Thinking not much of it, I put them back and got on our computer and started searching for porn. I stumbled upon a few sites that featured transsexuals and I felt my cock jump a bit – there was something about these “girls” that had a little something extra. I was enjoying looking at pictures and video clips of the girls getting screwed. But when I came to a video of a guy taking a tranny cock up his ass, my mind wandered back to my sister’s dildos.

I went back to her closet and grabbed them both. She had one long, skinny one and one that was pretty close to the size of my own cock – 6” long and 2” wide. I grabbed some Vaseline from the closet and raced back to the computer. I started the clip again and my cock sprang to life immediately. I grabbed the skinny dildo and coated it with Vaseline. Kneeling in front of the computer, I reached underneath me, spread my ass and put the dildo right at the entrance of my asshole. Slowly, I began to push. Slowly, the long, hard dildo entered my ass.

I loved it! I searched for another video while I rode my first dildo. The longer I went, the easier it slid in and out. I found another clip with a guy with two trannies. One was in his ass and the other in his mouth. I quickly grabbed the other dildo, set it on its wide base on the desk, and started sucking on it like it was the real thing.

The overall sensation was too much. The sound of the guy moaning while he was fucked and sucked; the “girls” telling him to take it like the bitch he was; the skinny dildo sliding in and out of my ass and hitting my prostate; the dildo in my mouth; my hand furiously pumping my cock. I knew I was going to cum. I took my mouth off the dildo, leaned back on the dildo in my ass, and shot the biggest load ever all over my chest. I wiped some of the cum off my chest and tasted it. A bit salty, a different taste than anything else I had tried, but I liked it and swallowed it.

A few weeks later I went to the local porn shop and bought a couple of dildos of varying sizes and occasionally would use them. But was (and still am) primarily attracted to females. Since guys were not really interesting me, I continued to happily date women and, when the mood struck, occasionally use a dildo on myself while masturbating.

When I was 25, I started dating a girl named Cindy. The sex was amazing and we tried many new things. One night we came home from the bar around 2 am and tore each other’s clothes off. We both loved drunk sex. I could last forever and we would try just about anything. On this particular night I was on top of Cindy fucking her hard. She was grabbing my ass, trying to pull my cock in even deeper.

As Cindy adjusted her grip on my ass, I felt her right hand grab my whole cheek and her middle finger touching my hole. Sensing no resistance, Cindy moved her finger tip onto my hole and began rubbing it in circles. Hearing me gasp in pleasure at this sensation she asked, “Do you like that?”

“Uh huh,” was all I muttered.

“How much do you like this?”

“A lot. I love it!”

She then adjusted her grip and began pushing her finger at my hole.