NOT Your Grandma's Book of Progressive Erotica: Vol 2

Kinked

Dating an open-minded woman wasn't just about exploring new ideas to make the world a better place, but exploring new ways to please each other sexually as well. We weren't into bringing others into the bedroom, but if we had the opportunity to try a different position, a new toy, lube, or even atmosphere, we would try it. The combinations were so endless that we spent hundreds of dollars on items in the clearance section of sex shops. We would buy things online, in store and one time even fucked – so quickly as to not get caught – in the store we bought things from.

Between outfits, toys, lubricants, positions and locations, we had made up a long list of things to do before we got too old to have sex, or forgot what it was.

It was rather easy to do things in the bedroom, but we also had a weekly challenge of fucking in public and not in the same position as we had the week prior. I was amazed at how well we were able to keep the list growing while we continuously crossed things off of it. It was endless and kept the relationship burning with passion.

As Valentine's Day approached, we discussed what we should do, which ultimately led to us going online to look at clearance items from a local sex shop. Considering how much money we had spent and how many items we already had, we were somehow still missing a few things. We picked the top three items that were in our bracket for purchase and then wrote them on pieces of paper. My girlfriend had the honour of drawing the item we were going to be using on Valentine's Day and it ended up being a strapon.

Of all the things we hadn't done yet, her fucking me in the ass was one of them. I wasn't overly nervous about it since she had already fingered my ass and given me a rimjob before. This just meant we were taking it to the next level on the day filled with love.

The strapon came in the mail just in time for Valentine's Day. My girlfriend opened it before I came home from work to check it over and when I came home, she greeted me at the door with it.

"Whoa," I said. "Today isn't Valentine's Day." She laughed and then chased me around the house with it, eventually trying to bend me over the couch with my clothes on.

When the actually day rolled around, the humourous thought of her chasing me around with the strapon was on my mind. I saw it as something fun and kinky, so I wasn't afraid of her being in control of such a large item going inside of such a delicate part of me.

Laying naked on my back after receiving an amazing blowjob from her, I looked on in anticipation as she adjusted the pieces of the strapon so it was snug on her. She grabbed a bottle of lube and fingered my ass for a bit until she was able to squeeze a second in.

Her fingering my ass with two fingers felt a little bit weird compared to just one, so I braced myself for when she began to rub the strapon against my ass. She leaned over me, kissed me gently and then held my legs in the air as it gently slid in my ass for the first time. I expected it to hurt a lot more, especially when she went all the way in, but as she carried on fucking me at a steady pace, it became more and more comfortable as I relaxed.

Leaning forward again, she kissed me as her breasts rested against my chest. I put my arms around her and she continued to thrust her pelvis. At one point I wrapped my legs around her as well, but that was short lived with she thrust a bit too hard and I yelped.

"Sorry, babe," she whispered, returning back to a slower pace.

She then grabbed my cock and began to jerk me as she steadily fucked me. I told her when and where she was stimulating my prostate gland so that she was able to get me off. Jerking my cock and fucking my ass at the same time, she watched on as I made my faces of pain and pleasure at the same time.

When I began to cum, she pulled out of my ass and then hoovered the cum as it shot out of my cock. Holding my cock in her mouth, she licked it and sucked it a bit until I settled down a bit from the orgasm.

Pulling my cock out of her mouth, she looked at me and said, "Well then. I guess I know what we can do when I'm on my period next time."