Hands free orgasming and faltering steps to girlhood
Having become exceedingly dissatisfied with my current physique and being constantly reminded by my profile pic of how great I looked and felt 50 pounds ago, I've started back on my diet again. I also recognize the need to do things to keep my mind in a more submissive state and encourage my body to seek pleasure like a girl. Yesterday, I had my first hands-free orgasm in a loooong time!
I took some time earlier in the day to shave in order for my chastity cage to be comfortable. Then I cleaned with my douching toy and wore a butt plug for a while to get comfortable. Even with just that, I could feel my body becoming more sensitive to other things while my clit stayed safely out of the picture. After a couple of hours of household chores, I grabbed a towel and one of my favorite dildos, and layed on the bed to watch PornHub on the bedroom TV.
I did a quick search and pulled up a couple of 15 to 20 minute long sissy encouragement videos. At first, I didn't watch the images much - I merely listened while I inserted my toy and began probing around, enjoying the sensations. For comfort, I eventually settled on laying on my back with my legs spread open and my curved 7" dildo inside of me. Steadying the sculpted balls of the toy with one hand, I began rocking my hips slowly as the head of the cock rubbed against my p-spot.
Having found a comfortable position with my head propped up on a pile of pillows, I opened my eyes and focused on the videos. My breathing grew uneven as my hips circled on the dildo inside of me. Images of genetic and transgirls in bliss with men flashed before me and I smiled. A girl would be sucking on a thick, sexy cock, and I would be aware of how empty my mouth felt. I'd see a girl on her knees and a hung handsome guy balls-deep inside of her, and I'd let out a sigh, feeling my ass clench on the toy.
A warmth began to rise from within my chastity cage, and I started to flip through my memories of men I'd been with before. I thought of the older married man who had me sneak over during the day so I could suck his cock in the bed he shared with his wife, and I could remember the sounds he made as I sucked and swallowed. I remembered the man who made me strip naked and wear a pair of panties he gave me, ordering me to crawl to him and worship his cock with my mouth. I loved how he called me a good, obedient girl. I remembered the men fucking me in bath house steam rooms, adult theaters, and park restrooms. I remembered how their hands felt, grabbing me roughly while they pumped and thrusted in me like the toy I was grinding on now.
After what seemed like an eternity, but was only 15 minutes, my back arched, my legs spasmed, and I could feel wave after wave bursting from my tiny pink chastity cage. I also became aware of how high pitched my voice was. Somehow, the angle my head was at on the pillows helped clench my throat, and I became aware that I was moaning with feminine passion, begging the toy cock to not stop fucking me. I continued moaning and slowly grinding well after the waves had subsided, until I collapsed in a twitching heap on the bed.
Normally, I would be in a rush to clean up and get changed if I'd came like a man. But this was no male orgasm. This was feminine bliss, and I reveled in it for a while longer - wishing one of my previous daddies was there to still use me as he desired. Eventually, however, I cleaned up, but left my cage on for a while. I put on some panties and a girly shirt, and continued about my day, satisfied, but still hungry for more.
Here's hoping this will be the start of something VERY very good. I need so much more...