Dressing in women’s clothes is my biggest turn-on. You could, in fact, call it my greatest passion. The varied textures, the sweet smells, the sheer beauty of feminine attire all seem to unlock a whole secret world inside me.

After my college classes were over for the day, I would make for my place and my secret stash of panties, dresses and makeup. Then I would strut before the full-length mirror in my bedroom, letting myself live for a while in the blissful fantasy I had created. Would I be a pretty blonde that day or a sultry brunette? Was I a stern female executive or a sweet, submissive girl-toy? I could be any woman I chose, and I loved it.

It was while I was in college that I met Simone, who would become my girlfriend. She was a slim brunette with a taste for vintage styles and a quirky sense of humor. I was far luckier than most guys in my position. Simone didn’t just love me. She understood me and supported me in all sorts of ways. Adding to my collection of “pretty things” was never a problem with Simone by my side. She would take me out shopping as often as we could afford it. We’d come home with tons of goodies, and she would spend an hour or more making me up, painting my nails and dressing me in my new dainties. Sometimes we would simply sit together chatting, trading notes on fashion trends and whatnot. Other times we got into some fairly involved roleplay. Our friends had no idea of the secret life we shared. Most nights we were regular college students, going to clubs, concerts or ball games, but when we were alone together, we were like two completely different people.

Simone brought a few of her own somewhat unconventional desires to the table as well. She loved a man in a dress, but she also took particular pleasure in him being submissive. In fact, she told me early on that as far as she was concerned, having a boyfriend and having a slave were one in the same. It certainly didn’t bother me. In fact, some of our hottest nights together were those in which I played her “sissy.”

We’re still playing those games, and there’s one recent night I remember with special fondness.

The school we went to was fairly small, so the various cliques tended to be fairly tight. Everyone seemed to know everyone else. One of our mutual acquaintances was a girl named Rachel, who everyone called Rani — the Hindi word for queen. She was really stunning, with long black hair and strong, gorgeous features. She liked to dress in black leather and drop hints that she was seriously into BDSM. Still, neither Simone nor myself ever considered her a good friend. She came off as a bit haughty, and her sense of humor could be rather cruel.

But Rani had really liked Simone — for her fashion sense, her awareness of various scenes and subcultures, and her personality. One day, about two years after graduation, when Simone and I were living together in a small apartment in New York, my girlfriend received an email from Rani saying she was planning a trip to the city and wanted to have dinner.

“I doubt she even remembers me,” I told Simone.

“I actually hope she doesn’t,” Simone said, her eyes sparkling. “Do you want to have some fun?”

Simone wrote back to Rani, saying she would love to have her over for dinner, which would be prepared by her live-in “sissy slave.” Predictably, Rani was delighted. Even in college, she loved the idea of having a submissive under her heel. The next best thing would be to share Simone’s.

So, we set a date and tore into making preparations. The dinner was no problem, as both of us loved cooking. All that was left was to turn me into the perfect sissy. We spent the entire afternoon before Rani’s arrival getting me ready.

When we’d finished, I barely recognized myself. I was wearing a filmy negligee and cherry red pumps with criminally high heels. Simone gave me long lashes and a pursed rosebud of a mouth that seemed made for covert kisses. As a finishing touch, Simone trimmed my hair close to the scalp and fitted me with a new blonde wig, short and curly. With my elaborate makeup, I looked like a Kewpie doll version of Marilyn Monroe. I looked terribly innocent and absolutely delicious. Honestly, if it were possible, I would have taken myself to bed the minute Simone laid down her brushes and lipsticks and fucked myself silly.

“Do I have time to jack off a little before her majesty gets here?” I asked, making my voice all breathy and sweet. “Just a little?” 

“No,” Simone said sternly, turning me around so she could give my ass a disciplinary swat. “She’ll be here soon, and I still have to dress. Go set the table.”

As Simone had predicted, Rani was knocking on our door moments later, just as I was laying out the last fork and knife. Upon answering the door, I was startled by her physical appearance. Frankly, I had forgotten how hot she was. She seemed taller than I remembered, with the same heavy mane of jet-black hair and piercing green eyes. She was one of those women who give off an aura of being the boss. I would have happily removed her boots and kissed her feet then and there.

She clearly didn’t realize I was Simone’s soft-spoken boyfriend from college. To her I was a total stranger, a cute cross-dressing submissive to play with, and she was enamored with me.

“What’s your name, sweetie?” she asked.

“Her name is Dolly,” Simone said promptly, click-clacking into the room on her tall heels. She spoke with a cool, authoritative tone to her voice. “Isn’t it…Dolly?”

“Yes, ma’am,” I whispered, hanging my head just a little with my hands carefully folded over my crotch. I did that to look more submissive, but also because I was sporting a giant hard-on. Simone had shown me how to tuck my dick, of course, so my erection was taped securely under my itching balls. But it was still swollen to uncomfortable proportions.

“She’s precious!” Rani said, practically drooling.

“She’s OK,” Simone said with a smug grin. “Go freshen up, and we’ll eat.”

I had made a simple chicken dish with salad and wine. Rani wasn’t particularly interested in the food, though she drank more than her share of vino. She kept the conversation coming back to how cute I was, talking about people she knew in “the scene” and how Mistresses So-and-So and Whatshername at this particular dungeon would just adore me. Same old Rani.

All the while, I stood at attention beside her, refilling her glass and batting my eyelashes at her. Simone could barely control her giggles.

“Have you ever been spanked, Dolly?” Rani purred. “On that pretty little round ass of yours?”

“Yes, ma’am,” I said, honestly enough. “Miss Simone spanks me whenever I don’t do my chores properly, which is often. She…she has a special way of doing it,” I added. I said that on the spur of the moment. I was really awfully turned on, and at times like that, inspiration tends to strike out of the blue.

My remark was a big hit with Rani. She immediately had to know all about Simone’s “special” spanking method.

“She makes me hold my…my ladydick in my hand, just like when I play with myself. And then when she spanks my ass, it kind of pushes my ladydick into my fist and rubs it…and rubs it until I squirt.”

I kept my eyes downcast and let a pretty blush creep into my cheeks. All this was maybe pushing it a little. Simone was having a hard time keeping a straight face. Rani, of course, was eating it up and demanded Simone demonstrate her spanking skills tout suite.

But Simone had an even better idea and suggested, “Why don’t you do it, Rani, dear? After all, you’re the guest.”

This, predictably enough, sounded great to Rani. I was told to undo my tuck and whip out my ladydick without delay. I wouldn’t say I’m the best endowed guy in the world, or even the best-endowed sissy-slave, but my steadily growing excitement had definitely affected my hard-on. My cock, as it lay in my open hand, was nothing like the kielbasa-size dongs you hear about in porn stories, but it could definitely have given a decent-sized frankfurter a run for its money.

“Show it to Miss Rani,” Simone ordered. When I obeyed, our old classmate leaned forward until her warm, wine-smelling breath was driving me absolutely crazy.

“So pretty,” she whispered, and with that, she placed a tiny, teasing kiss on my swollen dickhead. I shuddered, and my balls felt like they were going to blow. My toes curled as much as they could in my tight red pumps. I arched my back, whimpering.

Oh God, I thought in absolute panic. This is it. I’m gonna blow my nuts.

But I maintained my control — just long enough for the spanking to begin. I wrapped my fingers around my shaft and cried out as Rani’s hand slammed against my rear, once, twice, then a third time. She was pretty strong, and she wasn’t holding back, either.

It was just as I’d described it. Each time her hand hit my ass, my cock jerked forward in my loose grip, rubbing against my sweaty palm. I longed to rub myself to climax, but as a good sissy-slave, that wasn’t an option.

“Spank her,” Simone urged, her eyes gleaming. “Spank her, Rani. She’s been a bad girl!”

To my surprise, Rani then dug her fingers into my hips and turned me around, so my stiff cock was bobbing before her face. A moment later, she closed her soft lips around my dick and was sucking me blissfully.

Simone and I gazed at one another — incredulous at first, then delighted. Then suddenly I had other things to think about. It turned out Miss Rani was a wonderfully talented cocksucker, and I was soon spilling my load into her mouth.

“Oh my God,” Rani whispered afterward as she grabbed a napkin to dab her lips. “Where did you find her, Simone? She’s delightful.”

A few weeks later, Simone told me we’d received a thank you note from Rani.

“She said she had the best time,” my sweetie assured me.

“Do you really think that’s true?” I asked.

“Oh, who knows?” Simone grinned, easing back in her chair. “She sure liked your ladydick, though, that’s for sure. So why don’t you come over here and show me what’s so special about it?”

Well, I could hardly resist, could I? I mean, I am her devoted sissy-slave!