An account of my playtime with Mistress Ryder and Mistress Firefly.

I Arrived at my destination, as instructed. Scanning my surroundings, I phoned Mistress Firefly and informed her I was there. “I know you are”, Mistress replied. “I’m watching you”. I struggled to find an answer. A moment of silence ensued. Enough time to wonder if anyone else was watching? Do they know why I’m waiting on this particular street corner? My face reddened a little. Even if they did know why I was there, it’s unlikely they would imagine the level of depravity I had invited upon myself. Mistress Firefly broke the silence. With a hint of mischief in her voice she gave me the house number and summoned me to her playroom.

On entering the playroom it was clear that both Mistresses were in a playful mood. I wasn’t sure if I was fortunate, or unfortunate to be their first victim of the day. After a chat about likes and limits, I was ordered to strip and the fun began — for the Mistresses, at least. Naked, and a apprehensive about what lies in front of me, my physical attributes, or lack of, there for both women to see. Mistress Firefly and Mistress Ryder were unimpressed and more than a little amused. They wasted no time in letting me know about my inadequacies. The playroom is a space for fantasies; somewhere you can be someone else for an hour. Stood before these two powerful women, I felt my status as a sissy could be more real than I imagined.

A sissy bitch needs a collar and Mistress Firefly wasted no time in fastening a leather one around my neck. Without uttering a word, Mistress Ryder made my first task clear. I dropped to my knees and began planting kisses on her perfect latex clad derrière. Such a lucky sissy; I could have done that all day, but no, Mistress ordered me to move down and worship her shoes. Mistress Firefly’s idea of boot worship was a little more devious. Wanting a demonstration of my cock sucking abilities, she ordered me to suck the heel of her boot. At last, we’d finally found something in which I might excel.

The Mistresses decided it was time for the real fun to begin. I was bent over and secured to the whipping bench. Mistress Ryder warmed me up with a spanking, before Mistress Firefly took over. It was obvious my pain threshold was low, but that wasn’t going to spoil the Mistresses fun. Mistress Firefly commented on my email, in which I expressed a like for strapping. She took great pleasure in describing one of her favourite straps, “Princess Bastard”. The description alone had me considering begging for mercy there and then. I didn’t, of course. I meekly agreed to having my buttocks kissed by Princess.

I have two distinct reactions to certain kinds of pain. The first, is a response that could be mistaken for laughter. It is an unfortunate response. Especially when you’re strapped down, bottom exposed, with two sadistic Mistress stood behind you. It is all the more regrettable when one of those Mistresses is wielding a leather, lead lined strap — the aforementioned Princess Bastard. I tried to convince Mistress that I was not laughing. Despite my protestations, Mistress Firefly saw my response as a challenge. She set about turning my “laughter” into tears. It didn’t take much doing. A couple more strokes and it was Mistress Firefly laughing now. She wasn’t the only one laughing. Mistress Ryder had noticed the other response I have to pain. My manhood was now so limp and shrivelled it could have been better described as a clitoral hood.

My ordeal was far from over. Moved from the whipping bench to the examination chair, my anxiety level increased. Before securing me to the chair Mistress Ryder took the opportunity to make me more lady like. She removed her stockings and gave me to me to put on. Not before making me inhale her scent from the stocking feet. Strapped into the chair, Mistress Ryder offered me a deal. I could keep the stockings on condition that I wear them to work and send the pictures. I could do that. This seemed like a deal weighted in my favour*. Now restrained, my stockinged legs in stirrups, I was primed for more torture. Both Mistresses snapped on disposable latex gloves hinting at what was to follow. Mistress Ryder had been keen to introduce me to her “wasp stings”. A short sharp needle prick, followed by an injection of a small amount of saline solution. That’s how Mistress Ryder enthusiastically described it. The first sting was to my balls. The prick of the needle was nasty, the injection of saline nastier. Mistress Firefly observed the procedure, like some kind of a wicked junior doctor. Mistress Ryder encouraged Firefly to handle me, feeling the effect of the saline solution. The second sting, to the the foreskin, was much more cruel. I’ve only been stung by a wasp once. It didn’t feel like this, though. I can’t be sure, but I doubt the wasp revelled in my suffering as much as Nurse Ryder seemed to.

Not to be outdone, it was Mistress Firefly’s turn to pile on the agony. Out came the electrics and I braced myself. This was a form of torture I was familiar with. I knew if I didn’t control my hysterical urges I would be in for a rough ride. This time, Mistress Firefly was more amused than offended at my response. Particularly when she increased the power. She found my facial expressions and thrashing limbs hilarious.  There was no respite. Mistress Ryder was having her own fun with a pinwheel. An instrument that I’ve always thought looks rather innocuous. Until I have one rolling over my sensitive bits, that is. It was with great relief that the electric pinwheel did not come out to play.

Not wanting to break their new sissy toy, the Mistresses decided I had earned a reward. It was time to experience Mistress Firefly’s new Venus 2000 milking machine. Unfortunately, this is a machine designed for men, not sissies. Even the smallest attachment could not provide adequate suction on my sissy clit. In my email I had listed SPH as play activity. I figured we could overlook the fact that I’m not that small — what a way to find out that you actually don’t measure up. Mistress Firefly’s boots provided adequate grip where the Venus 2000 couldn’t. She ordered me to hump away between her boots. Mistress Ryder didn’t hold back in letting me know what a pitiful sight it was.

Playtime ended with me stroking my maggot. Mistress Firefly made it clear what I was to do when I spilled my sissy cream — as if a sissy needs telling! Both women towered above me offering verbal abuse and encouragement in equal measure. Mistress Ryder describing in lurid detail my future life as a sissy. She painted a vivid picture of how a slutty cocksucker like myself would earn her keep at the Sissy Retreat. I shot my cream over my hand, spilling some on the floor. A moment of hesitation. I looked at the two expectant faces looming above me, then lapped up contents of my hand. Mistress Firefly ordered me to lick my spilled muck off her floor. I complied without hesitating. Gazing up at my tormentors, I saw their satisfaction. As a man I might be a failure, but as a sissy plaything I had proved to be a pleasing diversion to two superior beings. Both Mistresses leaned in closer to my face. I knew what was coming. I opened my mouth and accepted their final indignity.

*It was still good deal. Wearing Mistresses stockings at work was a more humbling experience than anticipated, though. Photos taken, I exited the toilets, somewhat red faced. Mistress Ryder had reinforced my sissy status without even being present.