Being caught dressed in drag leads to the most exciting Friday night this cross-dresser has ever experienced.

"Don’t forget to cross your i’s and dot your t’s,” joked my secretary as usual.

Ellie likes to tease me about my messy handwriting, a jumble of scribbles that somehow manages to represent my name. Ellie’s own handwriting is the opposite. In fact, Ellie is the opposite. She is as clear and precise with her writing as she is with everything else she does. From her shiny brown hair, always worn in a bun, to the crisp blouses she wears with her suits, she looks like an ad for corporate assistants.

As organized as ever, she had spread out the last correspondence of the day that I needed to sign before she left for the weekend. I made sure to initial every box she’d ticked. Then I stacked the papers and put my computer to sleep. By the time I looked at the clock, it was well after six. The office was empty. Bosses often are the last to leave.

Just to make sure I truly was alone, I took a quick tour of the building. I peered into each of the offices up and down the hall. The lights were off in the lobby. I even checked the restrooms. Yes, I was the only one remaining on this Friday night. I retreated to my office and took the garment bag from my closet.

I’d supposed the day would go late when I’d left for work. That’s why I had packed my evening wear. Without worrying that anyone might catch me, I stripped out of my leather loafers, gray cashmere socks, white shirt and charcoal suit until I was down to my black silk boxers. I took my kit into the executive bathroom and gave myself a thorough shave. I noted that my cock was already hard. I’d chosen a feminine shaving cream in a light pink canister — to get myself in the mood. The trick worked wonders.

Women are so lucky. Instead of spice, sandalwood or some other acceptably masculine smell, this shaving cream was perfumed with the scent of cherry blossoms. I reveled in the light fragrance as I whisked every stray blond whisker from my face.

My cock twitched in my boxers as I brought out my makeup case. The bag was striped in white and violet. Inside were cosmetics by high-end designers. I enjoy purchasing the top-of-the-line products. Only the best when I cross-dress. I used concealer before applying a luxurious foundation. This evening, I’d chosen a lilac dress to wear. I lined my eyes using a thin pencil that was a little darker purple than my dress. The color complemented my green eyes. I knew it was a good hue. I spend a lot of time perusing makeup sites and visiting cosmetics stores, and I’ve learned over the years what looks best on me. I selected a fluffy blush to add color to the apples of my cheeks, feathered on coal-black mascara, and finished with an orchid lipstick.

When I was totally done, I looked amazingly feminine. I’ve had years to practice with cosmetics, but I’m always aroused by the transformation. For a few moments, I flirted with my reflection in the mirror. I wear my hair short, yet cut in a fairly androgynous look. With the makeup, I was practically passable.

Back in my office, I stripped off the last remnant of my male attire. Then I shimmied into my favorite bra and slid in the inserts that turn me from a flat-chested male into a B-cup female. I was going to put on a garter belt because I find something so seductive in wearing the retro style, but I wasn’t ready yet. First, I reached for the lemon-yellow satin panties I’d selected that morning. My cock was throbbing fiercely because it knew what my plans were. Dressing up always turns me on. All parts of the activity are arousing to me, including the preparation.

I rubbed my palm against my panty-clad dick, and I felt the tiniest bit of pre-come leak from my slit. Maybe I ought to just jerk one off, I thought to myself. That seemed like a winning idea, so I flipped on my computer again, called up some porn, and began to work myself.

And that’s when Ellie opened the door. Jesus.

There was absolutely no way I could hide what I was doing. I had the bra and panties on, my computer volume up to hear the sighs and moans, and a pretty dress hanging from the coat rack. Ellie opened her eyes wide. Hand on my dick, I froze. Although I like to imagine that I can think on my feet—that this is one of the reasons I have succeeded in my business life — no excuse came to my lips. Luckily, one came to hers.

“I forgot to have you sign something,” she stammered. “I was already halfway horny . . . ” She bit her lip. “I mean, home. I was halfway home. So I came back. I thought I’d leave the papers on your dress for Monday . . . ” she tittered nervously. “Your desk, I mean. Not your dress.”

Her cheeks were beet-red. She looked as if she would have liked to melt into the floor. I reached for my shirt, discarded in a heap, but I didn’t put it on. There really was no salvaging the situation. The shirt was only going to emphasize the fact that I had ladies’ panties on. Even if I dressed in my business suit, there was no hiding my completely made-up face.

“But I see you’re busty,” she continued. “Busy!” She laughed again.

Her eyes were so wide. She clearly wasn’t sure where to focus. My computer. My hard cock. My delicate bra. “I’m sorry to intrude,” she continued in a rush. “You’re obviously working late.”

What I obviously was doing was watching porn while dressed in ladies’ clothes. We both knew this.

“Ellie,” I started, but what could I possibly say? I was trying out a new line of makeup for a friend? I thought dressing like a woman would put me more in touch with my feminine side? I went for honesty.

“On weekends, I like to dress in drag.”

Well, that was the truth. As exposed as I was, there really wasn’t much left for me to lose. “I was going out tonight, and I didn’t want to have to drive all the way home first . . . ”

There. I shrugged. Would she tell the rest of the employees what she knew? Would she blush and leave in an embarrassed shuffle?

She cleared her throat and said, “Every Friday night?”

“Most Friday nights,” I said. This wasn’t going in the direction I would have expected. She didn’t look like she wanted to leave anymore. In fact, maybe I had completely misread the expression on her face. Maybe she wasn’t mortified. Maybe she was excited. That’s when the evening took a turn for the erotic.

“Do you mind if I watch?” she asked next.

“Watch?” I echoed as Ellie came forward and took the shirt away from me. Her organizational character came to the surface, and she folded the shirt neatly and placed it on my satchel.

“Watch,” she repeated, motioning to my lingerie-clad figure. “Watch you dress up.”

I turned off the computer and settled back in my chair. I wanted to make sure I understood her correctly. But before I could speak, she was reaching for my dress.

“It would turn me on,” she said, “to see you dressed in this.”

Her hands stroked the lilac gown, treating the fabric with the respect it deserved. I tried to make my brain catch up with the actions. … Holy fuck. … Ellie, my right-hand man — well, right hand-woman — wanted to see me in my ladies’ clothes? My dick, which had softened at being caught, was back to full mast in no time.

“Are you sure?” I asked.

She grinned at me and nodded. Then she sat on my sofa and waited expectantly, as if she’d arrived for a floor show. I was the one to stammer now. I had never put on my outfits with an audience before. Yes, I’ve gone out to a few clubs in my attire, but that’s the extent of my sharing this part of my life. Mostly, cross-dressing was something I did for me. Ellie looked so interested, so supportive, that I felt my confidence return.

I lifted the dress from the coat rack and unzipped the back. Cautiously, I stepped into the dress and then pulled it on completely. The top portion was fitted, but the skirt billowed out in a cloud of chiffon and crinoline.

Ellie came forward and kissed me. She stroked my cock through my dress, and then she said, “You’re so hard. This turns you on, doesn’t it, Tony?”

Obviously, it did. I nodded, and she continued, “Can I help?”

I didn’t know how she meant. Help me with my hard-on or help me get dressed? Turned out, she meant both.

“How does the garter belt work? I’ve seen them before, but I’ve never worn one myself.”

I took a deep breath. I needed all the courage I could muster. Then I told her, “The panties go over the garter belt. I hadn’t gotten to that part yet.”

“So take the panties off,” Ellie said matter-of-factly.

This was a big moment. My lovely secretary wanted me to stand at least semi-naked in front of her. I bit my lip, then pushed down the panties. Ellie handed me the garter belt. I showed her the fasteners, and she had me turn around and lift the dress while she affixed the hooks in the back for me. Then she watched while I gathered the stockings and slid on the first one. I had to sit on the edge of my desk to accomplish this task. Ellie remained right by, watching close-up. She was so close, in fact, that I felt her hot breath against me. I was pleased with the way the fine fabric slid over my smooth skin. I go to a beauty salon for regular waxes, and the silk felt like flower petals against me. Ellie reached out a hand to stroke the satiny flesh at the top of the garters. I sighed, and she sighed. She seemed fascinated when I attached the stockings to the garter belt. Then I put the panties back on.

My cock was an aching beast at this point. I usually get a hard-on dressing up, but I’d never really considered what it would feel like to dress for a lover. It had always been a private fetish. I stood so she could see me in the entire outfit. Ellie looked as if she were almost ready to applaud.

“I want you to make love to me while you’re wearing your lovely clothes.”

The evening was definitely taking a different turn than what I’d originally planned. Ellie was removing her own clothes, until she was standing there in her underwear. Hers were simple, classy, a nude bra and matching panties. I wouldn’t have expected anything else. In comparison, mine were so colorful and shiny. Ellie seemed to appreciate the contrast. Her hands were in constant motion, stroking my breasts, lifting the hem of my skirt to cradle my ass cheeks through my satin knickers.

I took a moment to realize that we had crossed a line between boss and employee. I wondered if Ellie had realized the same thing. She looked up at me, her brown eyes filled with desire. I wondered if she would offer one of her many curt statements. Ellie was filled with wry observations. What she said was completely surprising: “Now fuck me.”

“Fuck you?” I echoed.

I sounded bewildered, I know. I wasn’t. I mean, I desperately wanted to fuck my secretary. Still, I somehow needed to hear her say the words again. I don’t think I had ever heard her swear before.

“Yes, Tony. Fuck me while you wear that beautiful dress. Fuck me while you have that garter belt on. I’ve never been with a man dressed in drag before. And I can’t think of anything sexier.”

I couldn’t either. But I wasn’t exactly sure how to take her. Bend her over my desk? Spread her out on the sofa? Ellie answered my silent query for me. She lay back on the rug in the center of the room and parted her legs. Clearly, she wanted to see me while we screwed. I pulled her panties off, and then I took mine off, too. But I kept on the rest of my outfit. Ellie sighed when she felt the fabric of my dress whisper against her. She pulled me down for a kiss, so our lips were pressed together while my cock searched out her opening.

She was wet. So wet. Dripping, deliriously wet. She had gotten as turned on by me being in a dress as I was.

“You look lovely, Tony,” Ellie said when we parted. “You, too,” I responded, because she did. My lipstick had smeared to her face. She looked decadent with the makeup stained from my mouth to hers. I rutted into her, my dress a poof of lilac around the two of us. Then she surprised me by rolling me onto my back so that she was astride me. She unhooked her bra and took it off. For the first time, I won the prize of seeing my secretary in all her naked glory. She was a work of art—alabaster skin, breasts that fit in my hands, no tan lines whatsoever, her skin the color of the inside of a seashell. On any other day, I might have taken the time to truly admire her form. But Ellie didn’t seem to want to take the time now. She pushed her hands on my chest for support, and then she started to raise and lower herself on my pole.

“I had an idea,” she confessed as she rotated her hips. “I had an inkling.”

“What do you mean?” I was panting. The way her pussy muscles squeezed and released me was sublime.

“Once, you had a little lipstick around your mouth when you came to work on Monday. I thought you’d had a wild weekend.”

“I had,” I assured her. I didn’t know which weekend she was referring to, but most of my weekends are drenched in drag.“You know what I mean.”

“Sure, but what else? Had you ever thought I dressed up like this?”

She shook her head. “But I’m glad you do. The way you dress at work is so serious. I’m glad to find out you have a hidden side.”

At the word “hidden,” she suddenly seemed to realize that my cock was touching her just right. She froze for a moment, and then she started to rock at a faster clip. I reached a hand between our junction, and I stroked her swollen clit. We had never even kissed before, and now I was touching her most sacred spot, the place where all of her pleasure was focused. Ellie looked at me through eyes glazed with lust. She seemed unable to speak, but she moaned, and the sound was so raw, so animalistic. I felt my cock growing harder inside her. I wouldn’t have thought that was possible. I’d never been this turned on in my life. I pressed a little harder as I worked Ellie’s button, and she cried out my name and climaxed in a rush.

Her pleasure was glorious to behold. My buttoned-up secretary had come undone. While I was still almost completely dressed, she was entirely nude. Somehow this made our fucking even sexier. My dress was rumpled, but I didn’t care. I knew my makeup must have been ruined as well. None of that mattered. What mattered was fucking Ellie some more, driving into her and bouncing her into the air. My sweet secretary seemed to be feeling the exact same way. She gently pulled away from me and then moved a few items on my desk. Watching her bustle around in the nude was incredibly exciting. She moved with the same thoughtful motions she always does. But now she was naked, and that made all the difference.

“Here,” she said. “If you fuck me here, I’ll be able to watch us in the reflection in the window.”

Goddamn. She was kinky! In a million years, I’d never have guessed. Ellie shows up at work twenty minutes early on the days she considers herself late. She packs her own lunches, and I’ve caught peeks before as to what she brings: sandwiches divided neatly on the diagonal. Polished red apples. Cellophane bags of cut carrots and celery. She is precise in all of her endeavors, as she was precise now, moving my cup of pencils out of the way, tucking my calculator into my top drawer, stowing my laptop in its case. When my desk was cleared of everything except the blotter, she bent over and waited.

I assumed my position and slotted my cock against her pussy from behind.

“Don’t tease me,” she said, looking over her shoulder at me. “Fuck me hard. Fuck me in that dress, Tony.

”I was awash in desire like I’d never been. The sound of the fabric rustling around us made me hotter than ever. Ellie steeled herself with her palms on my desk, and I further steadied her with my hands on her hips. Then I took a second, preparing myself for the ride, before slamming forward so she felt me inside her hard from the first thrust. Ellie’s moan resonated in the office. I gripped her tight and kept fucking her at the same pace. Ellie let loose a string of dirty words that would have made a trucker blush. I couldn’t believe that this was actually happening. But when I glanced in the window at our joined reflection, I knew I wasn’t dreaming.

Ellie’s mouth was open, hungry. And she was pawing at her own clit, rubbing her fingers up and around her jewel as I filled her pussy. Those tight muscles of hers did the job on me once more, milking me toward my climax. I lasted as long as I possibly could, balancing on that thin boundary separating pre-pleasure from an out-of-this-world orgasm.

Then Ellie said, “I want to go out with you while you’re dressed like this.”

“You do?” I was panting

.“We’ll have dinner somewhere nice, like two ladies out on the town. You’ll wear a wig for me, won’t you, Tony?”

“Oh, yes,” I sighed.

“And then we’ll go to a motel and fuck while you’re all dressed up, and then maybe . . . ” I was really fucking her hard now. She was working to keep her words coming.

“Maybe . . . ” I prompted her.

“Maybe after you fuck me, you’ll let me get a strap-on and fuck you.”

That brought me to my limits. I let out a guttural moan and filled Ellie to the brim with my seed. She worked her clit fiercely and came on the tail end of my own climax. I felt connected to her in a way I’d never experienced before. Why? Because I’d shown her who I really was. And she’d accepted me.

Ellie pulled off me and turned around. We stood there for a moment, regarding each other. Ellie looked untamed. Her hair was down. Her face was shining with spent pleasure. I had never seen her look so lovely before.

“Let’s go to your house,” she said, “and you can show me your closet.”

In a daze, I collected my gear, and Ellie dressed herself. That evening was the start of many fabulous nights of my dressing up for Ellie. Crossing my t’s has never been as exciting as when Ellie and I stay late after work.

— L.T., New York City