Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good.
At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job security. I was only 5'7" but made up for it with my good looks & great personality. Seriously I looked like a junior version of Chris Hemsworth's Thor just a bit less manly a build. But even better shoulder length hair. I was sadly widowed at 32, but I didn't let it ruin my life. In fact I used it to make myself better. I started to live my life and that included learning to embrace my other side.
You see, I decided to let my kinky side out. Why not. Too many people keep their feelings bottled up inside them and struggle through life. As soon as I decided to act on mine it was like a veil was lifted. My work and improved and through me the entire offices efficiency went up. My health improved, physically and mentally and I haven't felt been in years.
I was a closet cross-dresser, enjoyed bondage and bdsm games, and I always thought body piercing was hot. I even had my nipples pierced and a PA ring installed. It was really fun when a date found them for the first time. And none were ever put off by it. In fact they all said they could feel the PA ring when I was inside them.
But I guess much if not most of the credit for my personal improvements goes to encouragement from my lovely Mistress Emma, or Miss Em as she is often called. We met at a local BDSM club that I had started to visit and hit it off right away. She had quite a bit more experience than I did but I was a willing student and sub. In the first few months after meeting her I threw out my boxers and switched to panties, shaved my body and learned to worship hers. I Submitted to her paddles and canes and learned the joys of submission. It was all worth it just to be allowed to worship her amazing body.
Miss Em was and inch taller than me at 5'8" with golden hair a trim waist and beautiful bottom and a lovey c-cup chest. She was trim and toned from regular workouts, and men and women's eyes would turn towards her whenever she entered a room. She had a commanding presence and I was happy to play second fiddle to her.
Living only a few miles apart made it easy for us to get together. We regularly attended a few local clubs but spent most of our playtime together or with 2 or 3 other fem-dom couples that she knew, and a coupe of single domme women as well. I loved being on my knees between her legs while she or another domme was paddling my ass, urging my tongue deeper into her beautiful vagina or ass.
"So Mary I think I found a sub that may be a keeper." she told her girlfriend over dinner. "We met at the club and he's smart, intelligent, good looking, trainable and will make a really pretty sissy in time.
I still worry cause he is a guy. You never know if you can really believe them."
"Yeah Em, they say anything until they get to cum then its see ya girl. You are too good to put up with that shit."
"Listen Mary you are a wiz with computers. I would love to have you install and install some files and tracking stuff on his laptop. And maybe a couple hidden cams too. I will invite you to dinner at his house and keep him occupied. He will never know its there and we can set it so you can keep an eye on him too. We can follow her every move on line and even run sissy hypnosis tapes and subliminals in the background. In a month she won't remember who or what Kenny was. Lol."
Not long after I agreed to be her sub she called me at work one day and said she had a present for me and to pick up Chinese take out and bring it to her place for dinner. We drank some wine and ate with the usual small talk, all the while I kept glancing around the rooms to see if I could get a hint as to what was coming. She told me to clean up the dishes and meet her in the bedroom.
I knocked and waited to be allowed to enter the room. She was wearing 4" stiletto heel pumps, a black lace bra and crotch-less panty set and deep red lipstick. Towering over me in the heels she said one word, "STRIP." I hurriedly slipped out of my clothes and she grabbed me by my now hardening dick and directed me backwards towards the bed. With a firm push I found myself laying on the bed and she quickly was on top of me.
She knelt over my face and lowered her pussy down and I didn't have to be told what was expected. I was addicted to her taste and would lick her for however long as she would allow. After a couple of hard grinding orgasms she turned around and said it was time for my present. She lowered her ass onto my mouth and told me to start licking and not to stop for any reason or I would be in deep trouble.
As I worked my tongue between her cheeks she reached past my hard dick and grabbed me by the balls. The pressure from her hands slowly increased and with the increased pain level I could do nothing but force my tongue deeper into her beautiful ass to keep from howling in pain. I could feel my hard on wilting as the pain became worse. She finally released her grip and grabbed a metal cock ring from under the blanket and forced my balls and softened cock through it. I then felt a metal tube being slid over my cock and realized she had gotten me a chastity cage.
After putting the lock in place she lifted off of me and laid down next to me stroking the gleaming metal tube. "Like your present," she asked?
"Why Mistress" was all I could say.
"I got a promotion at work and will be traveling about 10 or 15 days a month and I want to be certain that my property is safe. I hope you don't have a problem with that?"
"No Mistress." What else could I say? She could have just thrown me out with the cage on. And besides, I really wanted this relationship to work so I was willing to do it to please her.
"Good. Now, before it gets removed, you will throw out all you men's under wear. The next time I am at your home I expect to see at least a dozen pair of pretty panties and 3 or 4 vintage style panty or long leg girdles. Understood slave?"
"Yes Mistress Emma,"
"Very good slave. Now if you want to reduce the time you spend locked up I suggest you consider embracing more of your feminine side because I have been seeing way too much testosterone affecting you lately. Otherwise you may be stuck in that thing for a while, and that may piss me off as I wont be able to play with it either."
"You will obviously be wearing panties under your clothes all the time now and if I find out differently I will start requiring bras or cami's too. There is one benefit for you, the panties will help support your chastity and boxers wont. I got you a pair to get started and will give them to you to wear home later."
So that's how the move towards Brenda started. I went out and purchased the required clothing the next morning. I didn't want to spend any more time than necessary in this metal contraption. Especially after I woke in pain twice through the night and again when my alarm went off. I texted Mistress before I was even out of the mall and told her of my purchases.