If you had told me five years ago that I’d wind up quitting my corporate job to become a sex slave, I’d have laughed in your face. I was single, dating, and thought I was having the time of my life. And I was until I met Mistress Margaret. She found me at a regular bar, having a beer one night. She was hot, but a little severe looking, with her hair pulled up into a bun and bright red lipstick. She was dressed in a tight black skirt that went down to her ankles and a ruffled black top. The bar attracted jeans and flannels types, so she stood out from the crowd.
“How are you doing tonight?” she asked, and there was something in her voice that made me pay attention. Instead of trying to shamelessly flirt with her, I spoke to her politely, answering all of her questions and wanting her to like me. I wasn’t sure why she’d picked me to speak with, but I was pleased. Over the next few hours she asked me a lot about myself, as if testing me, and I guess I passed because she finally said, “If you want to continue this discussion, come to my house tomorrow night.” She scrawled an address on a napkin and handed it to me. She didn’t give me her phone number, and I didn’t dare ask for it.
That night, I showed up at her place, hoping that my black jeans and favorite button down shirt from Brooks Brothers would endear me to her, or at least not get me kicked out on sight. I was more nervous than I’d been for a date in recent memory. Margaret hadn’t told me what to expect, but I’d surmised that she was going to put me through my paces, and that thought excited me. Before I even rang her doorbell, Margaret had brought out my submissive side and given my mind plenty of fantasy fodder.
She let me in, but instead of greeting me with a hug, she ordered me onto the floor. “That’s where you belong, below me. Don’t forget that.” Her words were unexpected and harsh, but they made my cock hard.
She instructed me to call her “Mistress Margaret” and gave me a tour of her two story home on my knees. I crawled my way into the kitchen, dining room and living room, and then followed her up the stairs. She had me visit every single room until we finally reached what she called her “dungeon.” The word sent shivers through me. “I’d like to test you out, see if you’d be a good addition to my household.” I didn’t know exactly what she was talking about, but I knew I wanted to obey her.
I crawled inside her dungeon, but I didn’t get a good look around because Mistress Margaret placed a blindfold over my eyes. “That’s better,” she said, as if to herself. “Now take off your clothes.” I did, with trembling hands, and once I was naked, she had me stand and face the wall while she tied my wrists behind my back. She then turned me back around, and then I heard another woman’s voice say hello, followed by Mistress’s invitation: “Do come in.”
My heart pounded in my chest. We hadn’t discussed the possibility of anyone else joining us! Although I was nervous and a little embarrassed, I still trusted her. Her voice was at once commanding and soothing. Mistress Margaret placed one hand on my chest, pressing me against the wall, and put the other on my dick. “From now on, this cock is mine. I control when you touch it, when you come, and what you do with it. Those are the rules in my house and outside of it, for as long as you’re under my command. Are you comfortable with that, Michael?”
I nodded, but that wasn’t good enough. She slapped my face and asked me again.
“Yes, ma’am. Yes, Mistress Margaret,” I stuttered.
“Much better,” she replied. “Tara is going to flog you now. I’ve trained her well, and you need to know that part of submitting to me means submitting to anyone I choose. I’ll return for you when she’s finished.”
So there I was alone with a complete stranger. I didn’t know what she looked like, though I imagined her pretty and petite, based on her voice. I was glad I was bound, because it forced me to keep my hands where they were and not try to block her blows. After the initial shock, though, I found that I liked being flogged. The thudding pain and heat that spread throughout my body made my cock rock hard in no time. Tara alternated light brushes of the flogger’s tails along my chest and over my hard cock with swift blows against my thighs, and when she had me turn around, she snapped her whip against my back and shoulders more times than I could count.
By the time Tara had dropped her whip and Mistress Margaret had returned to rake her long, sharp nails along my chest, I was a goner.
Ever since that night, I’ve been passionately devoted to my mistress. This had led to numerous changes in my life, including quitting my full time job in favor of freelancing to have more time to spend with her changing the way I dress, and asking Mistress Margaret’s permission to go out with friends. In return, she not only keeps me well spanked and allows me to serve her, but she has made me feel very special, and assures me I’m at the top of the hierarchy of her slaves. Once in a while, she even lets me have another woman to play with, under her supervision, of course.
That’s the reason why when Mistress Margaret informed me that she wanted me to dress in drag for an upcoming party, I didn’t dare protest. Inwardly, I was half aroused, half fearful. I didn’t think I’d make a convincing woman I’m six feet tall, fairly muscular and have very short hair. This would be a trying task for me, but one thing I’ve learned in the past six months is that my mistress is constantly looking to shake things up. She loves to challenge me, as well as all her other slave boys and girls. Some of them fail and are banished from her home forever. Watching her cast out a recalcitrant servant for a misdeed both impressed me and scared me, should I ever be the one to disobey or displease her.
I knew, though, that every time I’d participated in something I’d been uncertain about at the behest of Mistress Margaret, I’d been happily surprised by how pleasurable it was in the end. That’s why I let Mistress Margaret dress me in such an outrageous outfit, even though I found the idea embarrassing. The dress she’d chosen for me was hot pink, with a slit cut to the thigh. She paired it with matching five inch heels I had to learn how to walk in. Mistress Margaret had Tara shave me and select a wig from her collection. By the time they were done, I didn’t look like a girl, but I didn’t look all boy either.
Thankfully, we were driving to the party, but on the way there we stopped at a convenience store. “Go get me cigarettes,” Mistress commanded, handing me a twenty dollar bill. Not only would I have to go into the store, but I’d have to speak to the clerk, too! I felt my cheeks heat with embarrassment, but I obeyed. It was a mortifying experience, but my dick was stiff throughout the whole thing. My arousal continued through the night, but at the party, I experienced people directly commenting on my outfit, as opposed to the store clerk who’d merely silently raised an eyebrow. “What a darling,” someone said, patting my ass affectionately. At Mistress Margaret’s suggestion, a few women even lifted up my dress to peek at my cock, which was tucked into a lacy pair of panties.
Being at this pervy party and having so many dominant women fawning over me never got old. My cock was so hard it ached, and I hoped that Mistress Margaret or Tara or anyone, really, would be allowed to relieve me. Just when I was starting to panic about my state, Mistress Margaret whispered in my ear that she was saving my cock for herself.
Finally, at two in the morning, we returned to her home, where she had me lie on my back, still wearing the dress. She pulled my panties down to reveal my dick, and then climbed on top. That was the only position we’d ever fucked in, but I didn’t mind. After she’d come twice once while riding me and once from my tongue Mistress climbed back onto my cock and allowed me to come in her pussy!
“You’re very pretty as a girl, my pet. I look forward to dressing you up and taking you out again,” she said.
Smiles from Mistress Margaret were rare, so I was very pleased. I’m blessed to be part of her special household, and to hold such a prized place in it.
I hope more “macho” men out there find a dominant woman who’ll tap into their hidden submissive side, because they don’t know what they’re missing. Mistress Margaret has changed my life for the better, and I couldn’t be happier.
Mr. Michael C., Columbia, South Carolina