Sandi was admiring a pair of glossy black pumps when she said to me, “Look at these. Aren’t they to die for?”
I kept my expression calm, even though inside I was turning cartwheels. “Where’d you get them?” I asked, reaching out to touch the heels. It was like the shoes gave off little sparks, crackling between the smooth patent leather and my fingertips.
Sandi tossed her head a little, shifting her dark bangs back and away from her eyes. It was a signature move of hers — sassy, sexy and so Sandi.
She told me the name of the boutique, and I recalled it being one of her favorite places to shop.
“But that’s not all,” she said teasingly.
Sandi leaned to one side, reaching for the shopping bag she’d set down beside our bed and handing it to me. A moment later I was holding up a fire-engine red cocktail dress and was no doubt wearing an expression of awe on my face. The garment was a replica of another red dress in Sandi’s closet, one she’d had for about a year.
The only difference between the two was that the dress in my hands was maybe two sizes bigger. In case you’re wondering, there was another pair of patent leather pumps in the closet as well, though they’re somewhat smaller than the ones she’d just purchased.
You see, she’d gone shopping for me, and finding a larger duplicate of her beloved dress was an unimaginable stroke of good fortune.
“Try them on,” Sandi urged, obviously as excited as I was. I practically tore off my work clothes, while Sandi squirmed out of her outfit and ran to fetch her matching dress from the closet. A few moments later, the two of us stood side by side, holding hands before the floor-length mirror that took up one corner of the bedroom.
The effect wasn’t quite flawless. Sandi hadn’t bothered to put on her pumps. But her red toenails glinted through the sheer black thigh-highs she was wearing. And, of course, I was just a guy in a dress and heels. No makeup, slicked-down black hair and the beginnings of a five-o’clock shadow. But I could see the potential. Sandi laid her head on my shoulder and smiled at our reflection. Then she ran a hand over my thigh, feeling my cock stirring to life. What a thrill!
“We’re perfect,” she said, her voice nearly a sigh.
Let me explain. I’d gotten into cross-dressing in college, right about the time Sandi and I started dating. Of course, women’s clothes had always fascinated me for as long as I could remember. I would pick up the latest fashion magazines every month and watch every movie and TV show I could find about fashion.
I loved the feel of silk on my skin, and the tight sensation in the backs of my legs when I walked in high heels. I loved the way mascara made my eyes look. I’m fairly tall and thin, so there’s not much difference between my build and that of a tall, leggy woman. I’d look at myself in the mirror, and I’d see someone incredibly sexy and beautiful. I learned to fill out my narrow chest with rolled up socks stuffed in bra cups. I taught myself to tuck my cock between my legs and wear tight panties to hold my dick in place to preserve my feminine silhouette. But more than once I had to hastily tear off the undies, so I could jerk off.
Mind you, my predilections occasionally got in the way of my dating. Most women found my obsession fascinating, even delightful — at first. Then they tended to get a little put off by it, which led to a lot of awkward conversations and abruptly canceled dates. If they’d realized how many nights I’d spent modeling for myself in front of my bedroom mirror, I probably would have been even more lonely during my senior year.
It wasn’t a problem for Sandi, though. She loved my “hobby” from the very beginning, offering me fashion tips and taking me to clubs while I was all dolled up. Afterward, we’d fall into bed together and fuck like crazy. It shouldn’t come as any surprise that she and I fast became an item.
I would often dress up when we went out together. In New York City, where we’d attended college, that wasn’t as much of a problem as it would’ve been in my small hometown.
I’m noticeably taller than Sandi, but as I’ve said, I’m on the thin side, and we have similarly colored dark hair. It wasn’t unusual for people to mistake us for brother and sister. We’d often fantasize about playing twins sisters, going out in identical outfits and makeup. The idea of us side by side, turning heads, was just too hot to resist. Sandi had confessed to me that she’d masturbated thinking about it, and of course I had, as well.
But for far too long, we couldn’t seem to find the right outfits to complement our looks and feed our fetish. We’d tried everything from the most outrageous leather fetish gear to very conservative pantsuits. But with the red cocktail dresses, it seemed we’d found the perfect look for both of us. They were sexy and fashionable, and so in tune with our style they might have been designed with us in mind.
They weren’t, of course. But a “girl” could dream.
Best of all, Sandi’s birthday was the following weekend. An ideal evening for us to step out together in our matching frocks. We decided to celebrate our good luck with a quick bit of fun in bed, and to make it even more special, we didn’t bother to take off our red dresses beforehand.
I sat on the edge of the bed with Sandi crouched on the floor between my knees. She loved to pretend she was seducing me, as though I really were another woman and our physical resemblance made me irresistible to her. She pushed the dress up high, exposing my cock. When I’d stripped for her moments before, it was right down to the skin. So I wasn’t wearing either briefs or panties. My dick was hard, and it didn’t get any softer when Sandi wrapped my shaft with my dress and started jerking me off. The smooth material felt like heaven on my dick. It made me shiver — especially when she rubbed it briskly over my knob.
“Like that?” she whispered teasingly.
“It’s like…like I’m fucking the dress,” I gasped. It was a strange thought, but it excited me. And why not? If I truly loved the dress, why shouldn’t I fuck it?
“Maybe we should add some shoes.”
I was already turned on by the thought of fucking the dress. The idea of bringing the shoes into the mix made me even hotter. Sandi got her pair of pumps, moved the dress away and caressed my naked dick with her nimble fingers. Then she slipped the shoe over my cock, laughing at the sight of it perched there like some bizarre decoration. Then she began moving the pump up and down over my shaft as if I were fucking it. I lay back and let my eyelids flutter shut. The sensation of the shoe sliding against my hard meat was delicious. It was smooth inside, though not as silky as Sandi’s pussy. As she shoe-fucked me, I thought I detected a whiff of her feet from the pump’s leather interior. A delicious smell, earthy and tangy. The only thing more wonderfully sexy than a woman’s shoe is one that’s been well-worn until the perfume of her toes and sole are imprinted inside it.
If she’d gone on just a little longer, I probably would have lost control and shot off inside the shoe. Instead, she pressed her red lips against my cockhead, leaving a blaze of sticky lipstick on my flesh. The sight seemed to inspire her. She went to her vanity and returned with several cosmetics. She twisted open a lipstick and tapped it against my unadorned pout.
“Pucker up,” Sandi whispered, and when I obeyed she applied the brilliant red color to my lips. Next, she brushed some eyeshadow over my lids. A moment later she was kissing me eagerly, holding my shoulders with both hands — as though I was going to try to get away! Her kisses got steadily hotter, and finally I allowed myself to fall back onto the bed, letting Sandi climb atop me. My hard cock was pressed against her wet slit, and she writhed against it, tantalizing me with the friction.
“You like that?” she breathed. “You like that, pretty girl?” Hearing those words from her turned me on like you wouldn’t believe, but I couldn’t help notice she wasn’t looking directly at me. Instead, her lovely eyes were focused on the mirror. She was watching my reflection as she rode me.
“Oh God,” she whispered. “You’re beautiful.”
“So are you,” I gasped. I joined her in looking at the mirror, the sight of us grappling on the bed — so nearly identical, yet still distinctly separate — made me crazy. Instinct made me want to thrust up inside that tight wet slit of hers, but I couldn’t resist rubbing against her twat instead, matching her movements. The act jibed with my fantasy of being Sandi’s twin, as if we were lesbian lovers rubbing our pussies together until we drove each other crazy.
Soon, we were going at it hot and heavy, murmuring and gasping at each other. She snatched my dress back up and caressed my cheek with it. Then suddenly she lifted her ass up, just high enough to let her slip the dress between our crotches. Then she settled her pussy back onto the silky red fabric, moving her hips in an irresistible rhythm.
I felt come boiling in my balls. There was something weirdly decadent about rubbing against my girl that way. I breathed through clenched teeth, reveling in the knowledge that soon I’d be blowing my load onto that beautiful dress. On the other hand, I was more than a little reluctant to get it all sticky. But it didn’t really seem to be up to me. Sandi was working away on top of me, growling like a she-cat in heat. She clearly wanted to encourage me to give in to my need for release.
“Pretty girl,” she said, stroking my hair. “My pretty girl.”
That did it. My ass pushed upward as I jammed my cock against her. I felt my hot jizz pumping out of me, soiling the irresistible red dress.
Sandi gasped, letting her weight fully settle onto me. She petted my hair and kissed my chest.
“How long do you think it’d take to wash the dress?” I asked her.
“Not even an hour. Why?”
“I want to wear it. I can’t wait for your birthday. I want to go out with you, tonight.”
“Let me get that in the wash,” she said gleefully.