My girlfriend wanted me to try anal sex, fisting, and other new things, I always rejected her, I was not turned on by any of those things until one night. She brought home a video showing two women experiencing anal sex. I was quite turned on. After a couple wine coolers I told her lets experiment. She led me to the bedroom, I undressed as she got everything needed to take my anal cherry.

I laid on the bed on my stomach and she helped me put a pillow under my hips. She started by inserting a cotton swab with Vaseline into me so I could get used to something going in. After 2-3 insertions of the cotton swab, she changed to a pencil wrapped in a condom. This did not bother me at all, actually it was pleasurable.

Then she put on a disposable glove and slowly inserted her middle finger, the feeling of my asshole being penetrated like this was odd, but I was getting turned on. Slowly she moved her finger in and out, in and out. Many times she would rotate her finger around. I started breathing heavily and could feel myself getting very wet.

 She told me that she felt I was ready for something bigger, her 6 1/2 inch strap-on, I took a deep breath and told her to go ahead. She put some lube on the strap-on and around my asshole. She told me that when I feel her pushing in to push out and the head will go in smoother.

I felt the head push against me and I pushed out and the head popped in, I was ready to scream and tell her to pull it out, she told me to relax the muscles and it won't hurt. I did and she was able to slide the entire dong in my ass.

She stopped for a bit so I could get used to the size.

Then she started sliding it in and out of me, it felt so good and I was feeling like I was going to explode anytime. She started moving it faster and faster, I was moaning and telling her to give it all to me. Suddenly I exploded, my whole entire body shook with the onset of a terrific orgasm. She was right this was exciting and I can't wait to do it again.

She wanted me to do her this time, I agreed. I put on the strap-on with 8 inches for her as she had done this before. I lubed her up and she laid on her back with her legs in the air. She told me to be rough as she liked it that way. I rammed that play-cock into her, she yelled out for me to go deeper, I rammed deeper. Her ass opened up so big, I could of put another play-cock in there.

I grabbed her vibe and inserted it in her pussy, she gasped and her hips started moving up and down, back and forth. I pulled the play-cock out of her ass and inserted my hand, it went right in, she was so loose. She told me to slam her, I did, and she squirted everywhere. I put my mouth there and drank all her tasty juices. I then got on top of her and we ate each other until we both got off again.

As I am writing this, I am waiting for her to come home so we can start our evening of wine, dine, and sex, pure sex. She is fantastic and I am so glad she talked me into such a sensual thing. I love anal sex, and cannot wait to do it more after. Maybe tonight try fisting.