Putting On A Show

I once dated a nurse named Toni. As I think back on it, I’ve dated a lot of nurses, and I’ve found them to be pretty open minded and some downright kinky. I’ve written about Carla who was a nurse. After our first overnight encounter, she gave me a pair of her panties to wear home, and thus begun a long, kinky relationship.Here are the posts from that relationship:

http://sissyhumiliation.blogspot.com/2008/02/carla.html

http://sissyhumiliation.blogspot.com/2008/02/carla.html

http://sissyhumiliation.blogspot.com/2008/02/carlas-first-lesson.html

http://sissyhumiliation.blogspot.com/2008/02/house-dressing.html

http://sissyhumiliation.blogspot.com/2008/05/carla-takes-me.html


Toni was a real go-getter. After our first date, Toni was stripping of her and my clothes and fucking on the couch in the basement .

I revealed to Toni pretty quickly that I was a crossdresser, and on the second visit to her condo, she gave me a tour of her underwear drawer. She showed me all the matching panties and bras that she had explaining that she always wore matching things under her clothes. Picking out a pretty pair of silky panties, she handed them to me and said I could borrow them. She thought it was sweet that I would be wearing her panties. I was already wearing a pair of my own, and she knew it.

The next day, we were talking on the phone, and I told her I was hard as a rock wearing her pretty panties. Toni was amused by all this. The real fun came when I returned the panties to her several days later. I had laundered them, and put them on the kitchen counter. She asked me how I liked wearing them, and I told her I enjoyed the silky feeling of her panties against my cock. “Show me,” she said. “Rub yourself with them.”

I unzipped my pants and wrapped her silky panties around my cock. I started to stroke myself with them, much to her delight. I was getting visibly turned on as I continued to stroke myself. “Cum in them! I know you’ve been wanting to!” I quickened my stroking as she watched with an amused look on her face and her hands on her hips. She said, “I’ve never had a boyfriend jack off with my panties.” Well of course she hadn’t. She’d never dated a sissy before.

I felt a bit objectified standing before her in the kitchen masturbating as she watched with a sly grin and her hands on her hips. Just as I was getting close to cumming, she cheerfully said, "Squirt, squirt, squirt!" That did it. I let myself go and came loudly while Toni stood there watching.

“Did that feel good, honey?” she purred. I nodded. “Let me see…” She wanted me to open the panties and show her my load. “Ooooh… good boy…” The tone of her voice made me feel small, like a little boy. Good little sissy made a puddle.

But this hadn’t been the first time I had put on a masturbation show. I’ll tell you about a show I put on for a small group of women.

Aren't these cute?

"Slip them on for me, won't you?

"Yes, they look just darling on you.

"Now I want you to kneel on the edge of the bed while I lube up my black strapon.

Put your elbows on the bed, dear. I'll be very gentle with you..."

Here, put these on!

Here, put these on for us. Aren't they pretty?

Yes, they're totally sheer so we can see your little thing through it, and we can watch it get hard. Look! It's getting hard right now as you pull them up your legs.

All the girls are giggling now. We can see your shame.


Oh! It's getting harder now that you can feel the stiff, sheer material. It's poking straight out and making a little tent, isn't it?

It's so funny! Your little thing is sticking out! OMG! We're all laughing.

Awwwww, don't cry.