Anal Play: Early Discoveries

I never thought that I'd stick something up my butt to have a good time.  It just seemed so weird, and if I asked my old self about it, I would have made a face showing my distaste for such an odd thought.

But as I've stuck my toe into the land of sissy delights, I've become curious to try this forbidden fruit.

I bought a strapon a few years ago and asked my wife to use it on me.  It probably wasn't the best idea to just spring that on her, but she had expressed a desire to do it a few years earlier, and I was the hesitant one back then.

She flatly refused, and it was put in the closet for a rainy day.  As I began exploring sissy dares and assignments, I found one that dared the reader to suck on a dildo.

"I have a dildo in my closet," I thought, and decided to go get it.

Of course, there was a huge reluctance in my mind to do it.  I didn't want to do something gay, but as I secured the strapon to the pillow, I dared myself to do it, and it only took a little kissing and licking to have me mess up my panties after a few seconds.

Eventually, I began to play with it a little more each time, and one day I decided to stick it in my ass.

"I'm going to do it," I told myself, and pushed it up against my asshole.

It was difficult to push in, but eventually it started to part my sphincter, and I had an incredible feeling like I was going to shit all over the place.  Scared, I put it away for a long time.

On another occasion, I decided to try it again, and eventually put it in.  I had to stop and breathe for a while, and eventually tried to get pleasure, but for the most part, just felt discomfort - nothing painful, but just full, and it stimulated my feeling of defecation.

Still, I stuck with it, and each time became a little more comfortable with.  It wasn't really the most erotic thing - in fact, it kind of made my erection go away at times.

I went through a period where I would dildo myself so that I wouldn't cum, and trying to see if I could have a sissy orgasm.  It never happened.

What I did end up finding was that stimulating my prostrate, along with masturbation was a bit pleasurable.