I am mostly a side. I do like my ass played with from time to time especially when receiving a blowjob, the occasional finger, love to get rimmed, sometimes like it when a hard cock slides up my crack. I even bought a prostate massager a few years ago and use that sometimes and really like it, but mostly I stick with oral and jerking off.
My wife has a big suitcase full of sex toys. She is super kinky and adventurous and has offered to peg me before. Even though I tend to lean towards being more open I am still nervous about having her peg me. The last time she went out of town I opened the suitcase and took out her nice dildo. Assuming that is the one that she wants to use on me.
It was about 6 inches long and maybe an inch or two in width, not big by any standards but for me I thought it was a good size. I took out the lube and started to play with it. It slide in fairly easily but I could not take the entire size. I am still fairly inexperienced when it comes to anal. I love sucking cock but I have not explored much more.
After a few minutes of struggle I gave up, cleaned it off, and put it away.
This weekend my wife was away again and I was determined to see if I could make it fit. I was already horny, watching porn and stroking, but I decided now was the time to try again.
I laid down on my back, legs spread and applied the lube to my ass. I worked a finger in, and then two. I was moaning and the precum was dripping from my hard cock. I relaxed a bit and took out the dildo and applied a lot of lube and pushed into my ass.
Again, I could only fit about two inches in my ass before it started to hurt. I stopped again, breathed really deeply and pushed harder. A little more slipped in but I was still hoping to get it further. My cock was so hard at this point and I took some of my precum and rubbed it on my lips.
I decided that it may be easier with a warm shower, so I turned on the water with the dildo still in my ass. Adding a bit more lube I entered the shower. The water felt amazing and so did the fake dick. I pushed more and could feel it slowly move deeper. I closed my eyes and kept breathing as I pushed.
And then it happened. The cock shaped dildo pushed all the way in and felt incredible. All the wall to the fake balls.
I had to see. So I got out of the shower and went to the big mirror in our closet and spread my ass checks to see the end of the dildo just barely out of my ass. It was balls deep and looked hot as hell. I played with it for about a minute but ended up just getting back in the shower and pulling it out.
I felt the emptiness immediately but was still so turned on. I did not cum right then. I wanted to wait until later thinking about a real cock in my ass.
No idea if I will ever do it but the thrill of trying and also me finally stretching my ass with the dildo made me cum so hard. Just thought I would share.