TV Submissive Gets More Than He Bargained for with His First Mistress

For my twenty-first birthday, I decided to fulfill a long-held fantasy and visit a dominatrix. I’d seen ads for such women in the back pages of the local papers, and with some cash I’d gotten for my birthday, I could afford to indulge in my first pro session.

I owned one pair of pink satin panties and had worn them—and come in them—countless times. I was hoping that my mistress would “force” me to be more ladylike, maybe make me try on a bra and walk in high heels, and then perhaps tie me up and spank me. But I wound up getting a lot more than I’d planned when Mistress Serena took my fantasy and ran with it.

I filled out a form at the dungeon that requested I identify my desires. I said I was interested in light cross-dressing as well as domination, with a side of humiliation. It all seemed pretty standard… until my session began.

Mistress Serena was gorgeous, a true goddess standing at six feet tall (I’m five foot eight). She towered over me in her shiny black heels, and her lips and nails were painted bloodred. “So, Patrick, it says here you want me to turn you into a girl. Patricia? Patty? What should we call you?” Then she let out an evil cackle. “You, of course, should always refer to me as Mistress Serena.”

“Yes, Mistress Serena. And, actually, I wasn’t necessarily thinking about transforming into a woman, so much as just wearing some panties and getting spanked. But I will, of course, defer to your greater wisdom and desires.”

I realized as the words left my lips that I’d just given her free rein. But wasn’t that the point? I kept arguing with myself until Mistress Serena snapped me back to reality with her first order. “Let’s have you slip into something more comfortable.” She steered me toward a rack filled with women’s clothes, from tops to dresses to skirts. On nearby shelves were hats, shoes, boas, and other accessories. It was like being in a boutique, yet everything was on the larger end of the size range.

Mistress Serena began humming to herself as she selected brightly colored items for me to try on. I’d pictured myself in pastels, or perhaps white, or maybe a chic black dress—not a bright-pink top and a purple skirt. “Oh, wait—wear these, too,” she said, handing me some soft, pear-shaped cushions. Noting my quizzical look, she explained, “They’re breast forms. They go in your bra.” And then she handed me one of those, too. There was no dressing room; I soon realized that part of my session was to be “humiliated” by being feminized in her presence. I was both aroused and nervous. Sure, I’d expected her to see me naked eventually, but not like this. My cock wasn’t even fully hard!

Under Mistress Serena’s watchful eye, I stripped down to my birthday suit and then tucked my cock into a pair of tight white satin panties. They were the only white piece of clothing I’d be wearing. I made sure my package wasn’t visible before sliding into the purple suede skirt. Then I slipped into the bra, put in the breast forms, and slipped the blouse over my head. When I looked in the mirror, the colors were almost blinding to me. My usual wardrobe consists of muted grays, browns, and blacks. Still, the silhouette before me was decidedly womanly, and the more I looked at myself, the more glad I was for the tightness of the panties, which were keeping my swelling dick from showing.

Mistress Serena surprised me again when she pulled out the makeup—and again, there was nothing subtle about her choice of colors. She made me close my eyes as she took her time making up my face. For a moment, I worried that we were wasting too much of my ninety-minute session by having her prettify me, but then I silently berated myself for questioning my domme. However Mistress Serena saw fit to beautify me, I would defer to her wishes.

When she was finished with my face, she held up a mirror and told me to look, and to be honest, I didn’t recognize myself at first. I was no longer the average-looking, semi-attractive man I usually am, but a woman, albeit one made up quite garishly, with pink blush along my cheekbones, smoky black eyes, and glistening magenta lipstick topped with gloss. I was shocked. I opened my mouth, but the mild protest died on my lips. How could I say, “But I only wanted mild feminization?” I’d sound rude and ungrateful, and I was neither of those things. In fact, my cock was as hard as a rock. I wished I could jerk off, but that didn’t fit in with my new womanly persona.

Mistress Serena beckoned me to rise from my seat, put her hand on my back, and led me toward what I thought was her private room. Instead, she actually paraded me around past other dommes and clients! Everyone was staring at me, I was sure, even though I kept my eyes focused on the floor. I no doubt added to the color on my cheeks by blushing heavily with embarrassment.

“Isn’t she pretty? This is Patty. She’s new,” said Mistress Serena. “Smile, Patty—that’s what ladies do.”

I smiled as best I could, while feeling my cock strain within the confines of the panties. Surely that was something a real woman wouldn’t have to deal with! But that hardly mattered in the dungeon. After all, I had asked for this—in a way. I was smitten with Mistress Serena’s beauty and her command over me. She wasn’t the barking-orders type, but with her sensual voice, she could have asked me to crawl on the floor in front of everyone and expose my ass, and I would have.

Thankfully for me, though, she kept the rest of our session private, though she instructed me to tell people about it, hence this letter.

First, she fondled my cock and told me what a pretty pussy I had and that she’d like to fuck me someday with a giant black dildo. She showed me the toy she had in mind—and it was indeed big—but for the moment only made me suck it. “You can do better than that!” she scolded when I failed to take more than the first two inches into my throat.

“Yes, Mistress,” I said, even though I doubted her words.

“Don’t make me demonstrate,” she said, and the thought of her taking the fake cock down her throat almost made me come.

“No, Mistress Serena, I won’t. I can do it,” I said, with more enthusiasm. Sucking a dildo wasn’t something I had planned on doing, either, but I was desperate to please her, so I tried to channel that hunger into taking the toy down my throat. The second time, slobbering all the way, I got it about halfway down. I could tell that with more practice I would improve, though the toy was so big I didn’t think I could ever take it all.

“That’s enough for now. Next time, I hope you’ll have more control over your gag reflex. Now bend over this stool,” she said. I recognized it from her website as a spanking bench. Finally, I’d get the spanking I’d been dreaming of!

Yet, once again, that wasn’t quite what happened. I’d dreamed of a woman’s strong hand spanking me, and while Mistress Serena was certainly strong, she used a paddle. And instead of crying out, “Ow!” as I was inclined to, I had to count and thank her after each smack. “One—thank you, Mistress Serena,” I said after the spanking had begun. That first swat felt pretty good, sending a warm, pleasant tingling through my lower half. By the final one—number twenty—I was aching and sore, though still completely aroused. I was instructed to leave with the clothes I was wearing and to wear them back for my session the following week!

I immediately ran home and jerked off, recalling every moment of my session with Mistress Serena. I’d thought that visiting a domme would be a onetime birthday indulgence, but I was hooked. I’ve since started a part-time job just so I can afford to visit Mistress Serena every week and continue to explore my feminine, submissive side.

—Mr. Patrick D., Beaverton, Oregon