I had no idea I was into cross-dressing until Halloween.

Up until then, I hadn’t realized I would be excited by the way a pair of silk stockings would feel against my skin or about how much I’d be into shaving myself until my body was totally smooth and bare, or about what it would be like to slip on satin panties over my stiff cock. 

But I’m getting ahead of myself.

It happened because of a simple suggestion. Sophie, who is one of my coworkers, said that all she’d ever wanted to do for Halloween was dress up as a man, but she hadn’t worked up the nerve.

“Why would you need nerve?” I asked her.

Sophie shrugged and said, “Well, do you think I could do it? I’d really want to fool people.”

I eyed her. She’s nearly as tall as me, which puts her at just shy of six feet. She has a lean body and long legs, but not much in the tits department. She’s beautiful, though, her face stunning enough to turn heads.

“You’re too pretty,” I said, staring at her high cheekbones and those outrageously large green eyes.

“I’ve never thought of that as a bad thing.”

I was the one to shrug now. “You’re too pretty to be a guy.”

“You’re pretty, too,” she said, catching me off guard. “And you seem to do just fine.”

We stared at each other for a minute, and I could almost feel her sizing me up the way I was sizing her. If she wore a beard, I thought, something scruffy — a goatee, maybe. If she slicked back her hair and put on a suit. Possibly. Maybe from the right angle. Perhaps…

She said, “You wouldn’t need much.”

“What do you mean?”

“To be a woman. A padded bra. High heels. Stockings. You’re pretty close.”

For some reason, the way she said “stockings” made my dick hard. I was also feeling fairly turned on by the way she was looking at me, in a partially clinical yet deeply interested manner. So I said, “You talk as if you’re serious.”

“I am serious.”

We eyed each other for another long beat. I wondered if she could tell my dick was erect. I had no idea whether her pussy was wet or not, but the thought of finding out had me searching for a way to get back to my place or her place. Some place other than the office.

Suddenly, the two of us were naked together in my head. Then mentally, I was dressing her and she was dressing me. The dirty images were coming almost too fast for me to contain.

“I’m game if you’re game,” I said, and I was pleased that my voice didn’t give me away. I sounded as if the whole thing was a lark. Like, “Let’s see if we can fool everyone,” and not, “Let’s cross-dress and fuck like fiends.”

She said, “We’d shock the hell out of everyone.”

That’s how we found ourselves at her place, going through her closet to see what she had that might fit me. I’d brought over an old suit, one I hadn’t worn for years. Something I’d fit into in my more slender college days. We would have to have the pants hemmed. The jacket slightly altered. She could wear one of my ties. We had a friend who could do the makeup for her — someone who worked in theater.

I was more difficult to dress. Sophie pulled out a stretchy lilac number that she thought might work. The dress hit her at the knees. It was a little shorter on me — and terribly snug in the most delightful way.

“Your dick is hard,” she observed with a casual elegance, the way someone might observe that it was raining outside.

“So it is.”

“Why do you think you’re hard?” she asked, again in an almost offhanded manner.

I took a deep breath and thought about the right response. “The way you’re dressing me up is turning me on,” I said, and that was as honest as I could possibly be.

That was the night we took things to the next level of our relationship. But not until she had me fully in drag. She was totally into the whole experience. She messed with my hair. She applied my makeup. She let me stretch a pair of her panties with my thick cock.

When we were man to woman — his to hers — in reverse, we started making out. I kissed her firmly, paying careful attention to the way her lips felt on mine. But there was more to this kiss than any other first kiss I’d ever engaged in. I was wearing makeup! The sensation of the gloss enhanced the romance of the kiss for me. I could have made out with her for hours. But then she moved us forward. It was as if she really was taking a male role, a dominant posture. She danced me to the bed and then spread me out. For a moment, she simply observed me.

“I never thought… I never imagined that you could be… ”

“What?” I asked, my voice a hush. Not feminine, but not the normal way I spoke, either. I sounded slightly submissive, very sensual. A bit breathy. I liked everything about the way this game was going.

“So beautiful,” she finished, and then she stalked toward me, and her hands were everywhere at once, stroking me through the dress, then pulling down the neckline so she could paw at my pink push-up bra. Then she caressed my waist and touched my thighs. She was careful not to stroke my dick. I noticed how she skimmed over that portion of my anatomy. Of course, the fact that she wasn’t touching me there had me consumed with thoughts of what it would feel like when she finally did.

I was so excited that pre-come began to drip from my cock, making a noticeable wet spot on my pretty undies, which she saw when she hiked my dress to my waist. Her eyes lit up, and she pulled the panties down to free my erection.

My dick was as hard as wood. I watched her smile, her face smeared with my red gloss. Then she began sucking my cock, and I was bucking up toward her face. I could feel excitement flooding through me. Sure, I was in a dress, but I was still 100 percent male inside.

Sophie slickened up my shaft with her mouth before she stripped and climbed on board. I loved that she was nude while I still had on much of my feminine clothing. She spun around into a reverse cowgirl, and I felt her tickling my balls, then playing with my asshole. I grunted and shoved her even higher into the air with a forceful thrust of my hips.

“I’ll get a strap-on for Halloween,” she said, “to make our next time even more realistic.”

“How?” I panted. “Realistic how?”

“You’ll wear your dress, and I’ll bend you over the bed, lube up your asshole and fuck you.” That was simply stated, simply put — and those simple words made me shoot off inside her. I filled her up with my cream and felt an unimaginable release as my body was consumed by orgasm.

She climaxed soon after I did, letting me know she was all woman by squeezing my dick with her strong inner muscles. She eked out every last drop of my spunk. Then we collapsed together on the bed, both of us momentarily decimated by what we’d done, how intensely we’d fucked.

When we made love for the second time, we were nude — and I was all me once more. But it was good to know that whenever I want to, I can dress like a lady, and she’d be happy to be my man.