Let me tell you how I found my erotic destiny and realized Dolores was the only woman for me.
On one warm evening in June, we were running through the city streets, looking desperately for a free taxi.
“We’re going to be late,” I groaned.
“Stop whining,” Dolores told me sternly as she stepped to the curb to flag down a cab. One instantly swerved out of rush hour traffic and screeched to a halt before us. It was as if she’d summoned it out of thin air through the sheer force of her will.
Dolores pointed to the door and demanded, “Be a gentleman.” I hurriedly opened it for her. “You’ll be a lady soon enough,” she added wryly.
The truth behind her remark was partially hidden in the leather bag she had slung over her shoulder. The rest of it was under my suit, a set of feminine underthings that were distinctly at odds with my corporate male persona.
While Dolores told the cabbie our destination, I settled in the backseat and made a show of straightening my tie. But I was actually surreptitiously touching my secret outfit, remembering the words in the catalogue. In fact, I was whispering them under my breath: “50 percent polyester, 50 percent acrylic. Semi-sheer lace bra in black with embroidered lace trim. Underwire cups. Adjustable shoulder straps with cinch fastening.”
To me, they were magic words. Incredibly arousing. My nipples stiffened under that semi-sheer bra, and down below, something else was stiffening as well. Previously, I’d only indulged in such sexy escapades in my own private world. I’d just told Dolores about my predilections the year before, after she’d told me about her side hustle as a dominatrix. It seemed only right I should contribute my own confession to the conversation. I’d been a little worried — in truth, I worry about everything — but somehow, I’d known my secret would be safe with her.
Our relationship involved lots of fantastic fucking, and we’d learned that a terminally anxious male cross-dresser jibes rather well with a dominant woman. I’d even sat in on a few of Dolores’ sessions as her “sissy slave girl.”
That night, though, we were taking things to the next level, but my first challenge came even sooner than I’d expected.
“You’ll have to change in here,” Dolores said matter-of-factly.
She’s a small woman, curvy and compact, with a penchant for black clothes and red lipstick. I love the way her eyes flash when she lays down the law for her “slaves.” Or I usually do. But this time, they were flashing at me.
“Change? Here? In the cab?” I don’t want to say my voice squeaked, but I know it did.
“You don’t have much choice, darling,” she said with a shrug. “We’re late already, and by the time we get to the club, it’ll be later still. Look at it this way — you’ll make a big entrance.”
“But,” I gestured discreetly at the cabbie’s head. He was nodding along to a jazz station, paying no attention to us.
“This is New York,” she said dismissively, as though it weren’t necessary to say anything further. And of course, it wasn’t. The man was completely oblivious to us. I knew perfectly well that Dolores and I could have fucked in the backseat and our driver wouldn’t have blinked. He’d doubtlessly seen much more shocking goings-on in his cab than a guy changing from Madison Avenue drag to…well, you know.
“Come on, Miss Flora,” Dolores said sternly. She opened her bag of goodies, but kept her eyes fixed on mine. “I’m not telling you again. Get that fucking jacket and tie off.”
What does it say about me that my immediate impulse was to give in? Maybe a better question would be: What does it say about me that as I undid the knot of my tie, I was sporting a lead-pipe hard-on that threatened to tear right through my delicate panties?
I kept my eyes on the back of the cabbie’s head as I began the intricate dance of stripping in a taxi. I kept expecting him to turn and flash me a big grin or a look of withering disgust, but he did neither. As far as he was concerned, Dolores and I almost didn’t exist. It was just as well because traffic wasn’t getting any better and driving required all of his concentration.
I’d finally gotten my shirt unbuttoned. While I reached for my shoes, Dolores helped me get the shirt off, stuffing it in her bag along with my tie and, moments later, my socks. My trousers were tricky; I had to lift my ass high off the seat and squirm out of them. I was down to my beloved underthings, and let me tell you, it was a rush. For all intents and purposes, I was Flora now, albeit with a big, rather butch-looking wristwatch and a totally unsuitable haircut. The inside of the cab felt confining. It was warm with my body heat and spiced with the mingled scents of cologne and sweat.
Dolores gave me no time to enjoy the moment; she threw my best sequined dress at me, along with newly bought pantyhose, a well-loved pair of pumps, and a beautiful blonde wig.
“Get to it,” she said. “I’ll do your face after.”
I looked back at the driver’s head. There was still no sign he was watching us, but it’s one thing to just strip in a cab, even if you’re wearing female underthings. It’s another to put on a wig and makeup. And yet, the idea that I could be watched was unexpectedly seductive. My imagination converted the short, middle-aged driver into a hot woman secretly observing me change. Secretly getting turned on, just waiting for a chance to take Flora in her arms and fuck her.
“Come on, come on,” Dolores hissed, breaking into my fantasy. “Even in this traffic, we don’t have all the time in the world.”
“Yes, Ma’am,” I said. And I did as ordered, but it wasn’t easy. There was barely any room to maneuver. I had almost gotten on the dress — which was a pretty tight fit around my ass — when the driver swerved, cutting in front of a slow-moving sports car. The sudden movement sent me flying toward Dolores, who was having trouble getting her makeup box out of her bag.
I found myself in her lap, nose to nose with her, and I couldn’t help but laugh. Dolores smiled, but she seemed less amused. She reached under my dress and pinched my balls through my panties. I squawked, but by now, my arousal at being in this situation had doubled. Dolores must have felt how hard my dick had gotten. She was the one who’d taught me how to tuck — an old female impersonator trick. Basically, it involved folding my dick — mercifully soft when I’d first dressed — down around my scrote till my cockhead was saying hello to my asshole, then using the panties to secure it. So, she knew just where to feel to gauge the extent of my new erection. It didn’t seem to entirely displease her. She squeezed and stroked my shaft until it threatened to spring free and rip through my panties.
“You like that?” she asked, speaking throatily, but not bothering to whisper. If the cabbie had been listening, he would have heard her. “You want me to jerk you off, Miss Flora?”
I nodded, delirious with desire for her. But I should have known we weren’t exactly lovers in this situation. I was closer to that sissy-slave status I’d mentioned earlier. That became clear when she gave my painfully erect, painfully bent shaft a sharp pinch, making me yelp.
“Well, too bad for you! We’ve still got work to do, so get it together!” she barked.
I did. At least, I gave it my best shot, considering how hot she’d gotten me. I finally wriggled completely into my dress and squirmed around, so Dolores could zip me up. While she did that, I wrestled my way into my hose and pumps. Then she went to work on my face. The soft kiss of the makeup brush was exquisitely erotic, and it didn’t take long before I was full-on horny.
“There,” Dolores said, putting my wig in place, like I was a queen being crowned. “Pretty good, considering the tight quarters. A good thing, too, because if I’m not mistaken, we’ve just arrived.”
Glancing through the window, I could see she was right. The lights of the club glowed nearby. The street was full of gorgeous women all dressed to the nines, all sashaying their way toward the entrance. Of course, not all of them were “women,” if you know what I mean. They really were gorgeous, though, and for a moment I felt my confidence flag. I mean, all of them had changed under optimal conditions, in hotel rooms or bedrooms, with admirers or lovers helping them along. They hadn’t changed in a moving cab.
Dolores must have noticed my crestfallen look.
“Go on, you look beautiful,” she said, not as sternly as she might have. “I’ll pay our charioteer, since your wallet’s in my bag.”
I got out into the cool night air, trading smiles with some of the other “girls.” I felt my anxieties draining away. This was my first pageant, and I’ll just cut to the chase and let you know I won first place.
Afterward, Dolores and I snuck into a restroom and fucked wildly up against the wall with me still in my dress and makeup. It was one of the best orgasms of my life.
That night led to a lot more adventures — and it was all thanks to Dolores.