My Life as a Phone Sex Operator - Part 4

By

My Life as a Phone Sex Operator - Part 4
Cross-Dressing

My phone rang one afternoon at 3:45 pm, and on the other end was silence. I said “Hello,” but there was no answer. I waited a moment, said “Hello” again, and finally I heard a shy, quiet male voice asking if I liked men who wore stockings. Well, truthfully, I never really thought about men in stockings, or panties, high heels, or anything. I just never really thought about cross-dressers. I was all of the sudden very curious and very interested in learning about this “new” fetish.
 

I asked him if he shaved his legs, and he said absolutely – he shaved them close and clean at least every third day. He asked if I would describe how I would dress him - from start to finish. I told him that I would first draw him a wonderful, perfumed bubble bath. As my naughty fellow would then have to undress in front of me, I would size up his body. While I was telling Jim these details, I could tell he was getting excited, I could hear it in his breathing, and in his short, encouraging responses. I told him to not touch himself at all, just to imagine what these things would feel like, and then I continued with my description.
 

I told him that before he could get into the bath, he would have to stand with his manhood tucked between his thighs, so he looked like a woman. He would then turn sideways, and look at himself in the mirror, and then he would step slowly and carefully into the steaming bath water. I could hear through the phone the sound of running water, and I realized that Jim was doing exactly what I was telling him, while I was telling him.

Next: More on arousing a cross-dresser...

More Juicy Content From YourTango:

Ask The Experts

Have a dating or relationship question?
Visit Ask YourTango and let our experts and community answer.