Anal Experience

The internet was born and available to the general public. I learned a lot by going on-line. The biggest thing that I discovered was that I was not alone in crossdressing. At first I thought that only a few people did it and I was one of them. But much to my surprise and pleasure I found that I was not alone in the desire to crossdress.

Looking at various websites I came across a few that showed crossdressers receiving anal sex. They looked like that they were enjoying it. Not having any desire to be with a man I was curious anyway. But I was not about to have sexual relationships with a man even if he was another crossdresser. I still do not have that desire.

But like I said I was curious.

One day when I was alone I got dressed again. I took out one of our toys and secured it the corner of a coffee table with some ribbons pointing straight up. I took a condom and covered the ***** and applied extra lube to it.

Standing in front of a full length mirror I did a ***** for myself and took off the blouse and skirt. By now I had a good erection that was in my panties.
I walked ever so slowly to the coffee table to the waiting toy. I reached up under my slip and pulled the panties down to my ankles. I removed one leg from the panties. I took some extra lube and put it on the rubber making sure that it was good and slippery.

I turned around and lifted my slip as I slowly lowered myself onto the toy. There was some resistance as from my sphincter as I went down slowly pushing the toy into me. It started to hurt so I backed off for a minute then started down onto it again. This time it went in further before it hurt and again I backed off of it. I tried again only this time I was able to drive the toy into me further and deeper. I slowly went down the shaft until my cheeks were on the table with the toy deep inside of me.

It was uncomfortable to be sure. I sat there letting everything relax as this was the first time I ever put something in there. Then after a few minutes I got up a bit letting the toy slide out just so far then I went back down on it and put my full weight on it driving it even deeper into me. I simulated doing cowgirl by going up and down on the toy. It was not a very pleasurable experience for me and did nothing except make my butt uncomfortable.

I tried again a few more times sitting on the toy. It still hurt at first but not as bad as the very first time. But still I did not find it a great thrill.

I even tried going into the doggie position and pushing the toy deep into me and simulated having sex by rhythmically pushing it in and out. Still no great thrill. I must have tried giving myself anal at least a good 20 times hoping that I would enjoy it. I tried different angles, rhythms, depths and toys.  But with each time it was not a pleasurable experience so I did not see how others on the internet enjoyed receiving anal.

So that was my anal experience and still have no desire to have someone penetrate me.

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