NOT Your Grandma's Book of Progressive Erotica: Vol 1

Painal

I had taken a huge risk introducing my boyfriend to my parents as they hadn't even fully understood why I was gay. Coming from a strict family, I figured it would take some time for them to come to terms with it, so I was going to be patient.

My boyfriend was accepted as being gay at a younger age than myself and I sometimes felt jealous when we would go to his parents place. Sure, they accepted me just as much as they accepted him, but I never had that growing up. I wanted to be accepted in all aspects of life and especially in my boyfriend's fantasies that he kept hinting at.

He would always beat around the bush about how he was a freak in the sack, but would never give me a straight up answer on what that entailed. I would be left guessing for hours on end as he laughed at every silly thing I said. It was quite frustrating for the most part, until I began to tickle him and he would say mercy. Apparently he was so ticklish that if I didn't stop, he'd pee himself. If I ever needed information from him, I knew how to get it.

When I went to his apartment for our weekly homemade dinner date, I was greeted by an aroma of flavours. He spent a lot of time in the kitchen with his mother growing up and learned a lot in his culinary school as well. He enjoyed cooking and one day wanted to open up a restaurant.

After dinner we got stoned and I prodded a bit about his oh so kinky fantasy life that he could never tell me about. He was reluctant at first, but I guess he finally wanted to tell me– or as I would soon find out, show me.

I walked with him to his bedroom and then sat down on his bed as he asked me to. Waiting there, he rummaged through his closet to find a rather plain looking box. Returning to the bed, he sat down beside me and opened it, revealing all sort of sex toys: some short, some long, some thick and some... extra thick. I was left rather speechless. I had never used toys on myself before, just the real thing with previous boyfriends.

"So you're addicted to masturbating?" I asked hesitantly, with a hint of uncertainty in my voice.

"Not exactly..." he replied. "It's more like painal."

"Painal? What the heck does that mean?"

"Painful anal," he explained, pointing to the biggest toy he had.

"Oh... gotcha." I wasn't entirely sure what to do with the information, but I was more than just a little intrigued as to how his skinny ass took that huge toy. "What do you start with?"

His half ajar mouth said it all. He hadn't expected me to be all for the sex toys, or his fetish of painful anal. Looking through his box of toys, he then pulled out various sizes prior to the big one – as well as the big one – and then placed the box with the rest of them on the floor. Walking over to his dresser, he opened the top drawer and pulled out a massive bottle of lube.

I guess I didn't realize how serious he was until he was butt naked, on his back, legs up in the air, with me inserting the "big one" into his anus. He cringed a bit as it finally slipped into his ass and I forced it ever so slightly in and out of his ass.

"Are you enjoying this?" I asked. All he could do was bite down on his lips, nod slowly and then breath deeply.

"I could go bigger actually." He wasn't looking at me when he said it and missed my wide-eyed reaction to his claim. Bigger? Really? He didn't have anything else to stick up his ass, so I couldn't imagine what he had in mind.

"There's nothing bigger in your box, so what did you have in mind?" There was silence for a while and then he cleared his throat.

"Your fist."