In My Boss' Skirt

"Ow!" I yelped as the cup slipped out of my hand, hit my thigh, and tipped over, spilling hot coffee on my crotch. I jumped up out of my chair and tried to lean forward to get the hot liquid off my body. "Dammit! Ow..."

I was grabbing some napkins to try and wipe everything up when my boss, Hannah, stepped out of her office. "John, everything OK?" she asked.

"I uh, spilled my coffee," I explained as I wiped. Hannah was around my age, young for a financial advisor of her caliber, and I thought she was very pretty. She had long brown hair, which she sometimes kept up in a bun, but today it was hanging loose; calm, brown eyes; and long legs, so long that she was taller than I was when she was wearing heels, which she always did in the office. I had a little bit of a crush on her, which was half the reason I had initially taken a job, but she was a great boss, and I found myself feeling as though I would like the job even if I didn't like how she looked.

But I definitely liked how she looked, and I was just as definitely embarrassed to be telling her I had just spilled my drink like a small child admitting something to his mommy.

"Ooooh," she said. "Are you hurt?" She really did look good and complemented it with great style as well. Today, she was in a white button-up blouse, navy pencil skirt, nude tights, and navy heels. Her blouse was unbuttoned at the top, showing a silver necklace that matched her earrings. It was nothing fancy or spectacular, but she did it well.

"Nah," I replied, hoping I wasn't blushing. "But..." I gestured at my pants, a deep dark stain on the crotch and thighs. "Kinda soaked."

"Mmmm," she frowned, concerned. "Do you have another outfit?"

"No," I told her, feeling more and more embarrassed by the minute.

"And you live so far away, so you can't really go home and change..." she mused. She looked at me for a moment and it seemed like she made some sort of a decision. "Luckily, I've got something."

"Got... something?" I asked as I watched her retreat into her office. The door was open but because of the angle, I couldn't see what she was doing. Confused, I continued to try and wipe off my pants. It was helping some, but my pants were going to be wet for the rest of the day. It was Friday, and we weren't busy at all, but there was still a couple hours before I would be able to go home, which itself would be nearly an hourlong drive with all the traffic...

"Here, this should fit you," said Hannah, jolting me out of my thoughts. I looked up at her and my heart skipped a beat when I saw what she was holding.

"A... s-skirt?" I asked her. It was a short navy pencil skirt. I had probably seen her wearing it before, but my brain was suddenly too scrambled to be sure. Wha- what if she knows? I thought to myself. She can't know... She can't...

She nodded. "Yep."

She can't know. "Bu-bu-but... I'm, uh, I'm-"

"A man?" she asked me, her eyebrows raising. "John, I know you're wearing a bra under that shirt.

Ohmygodohfuckohgodnosheknowssheknowssheknows. The embarrassment I felt earlier was nothing to what I felt now, and my bra, red and black and matching the pair of panties I was also wearing, suddenly cut into my skin. I tried to speak but couldn't get any words out.

"John," Hannah said. She walked closer to me and I put my head down, but as she got next to me she put her finger under my chin and pushed up so I was looking into her eyes. She was smiling. "It's OK!"

"R-really?" I asked, not believing her. I loved wearing lingerie and had gotten to the point where I pretty much always wore panties and a bra underneath my work clothes, but I had been scared to death of Hannah finding out and being disgusted with me or firing me. In fact, I had never told anyone of my crossdressing habits. "H-how did you know?"

"Some of your shirts are translucent when the light's bright enough."

I hung my head. "Oh..."

"But, John, I swear, it's fine," she told me. "I mean, it wouldn't be fair if I could wear a bra, or a skirt, and you couldn't, right?"

"Yeah, I guess..."

"So, c'mon," she said cheerily. "You don't want to sit in those gross, wet pants for the rest of the day, do you?"

I shook my head.

"And," she said, glancing down and up my body, "you've got a nice figure. You'll look cute in this."

She laughed, and I blushed again as she handed me the skirt and something else. I looked down at the second item to see it was a pair of tights.

"It's cold in here," she explained. She was right, it was always cold in the office during the winter.

I swallowed. I wanted badly to put on the tights and the skirt, but my hands were trembling as they held the clothes. "Hannah..."

"Shhh," she said, cutting me off. "There's no one here but us, and no one else will come in today. No one will see you but me." She stepped in a little closer and lowered her voice. "John, I want you to wear these..."

I swallowed again. "OK..."

"Yay!"

Nervously, I walked around her and made my way over to the bathroom, stepping inside and locking the door behind me. My trembling hands put the skirt and tights on the edge of the sink, and suddenly I realized Hannah had given me a third item as well. I held up a lacy black thong.

"Oh my god," I said quietly. Hannah hadn't said she knew I wore panties, but she was no fool, and it was natural to infer I was wearing panties if I was wearing a bra. She's gotta know...

I put the thong back down and took off my shoes, belt, pants, and socks. The coffee had soaked through my pants and my panties were wet as well. I reached towards the paper towel dispenser to try and dry my panties but pulled my hand back before I ever got there. I knew it was pointless. I slipped off my panties and then grabbed some paper towels, drying off the little bit of moisture that was now on my smooth, hairless cock.

Now naked from the waist down, I looked back up at the clothes Hannah gave me. I was still nervous, but she seemed supportive, so I began to reach for the thong, but a thought struck me: what if it's all some big prank? What if she's on the other side of the door with her phone out, ready to video me?

I almost put my arm down, but Hannah had never seemed the type of person to do something like that. She was always kind and supportive of me. I decided to go for it.

I grabbed the thong and stepped into it, slowly pulling it up my legs and nestling it in place. Of course, it wasn't the first thong I'd ever worn. It nestled neatly into place and actually had enough frontal coverage to cover my balls, which was nice. I pulled the tail of my shirt up and looked at my ass in the mirror. It looked good.

Next was the tights. They were black, though low denier. I tried to savor the feeling of the nylon on my skin as I pulled them up.

Last came the skirt, which was gray and had a zipper on the right side. I pulled it around myself, having to waggle my hips back and forth to get the zipper all the way up. It was tight and not very long, only coming down to the middle of my thighs. Once again, I pulled up my shirt and looked at myself in the mirror. The skirt showed off some surprisingly nice curves, and I enjoyed the feeling of rubbing my legs together. "Wow," I whispered to myself.

I walked over to the door and took a deep breath before opening it.

Hannah was just outside, but her phone was nowhere to be seen, and she smiled as she saw me. "Oh my gosh, it fits so well!" she said. She motioned for me to twirl and I did, to which she clapped. "You look great, John!"

"Thanks," I mumbled back, happy she was happy but still embarrassed.

But then she frowned. "We're going to have to do something about that shirt, though. It doesn't go with the skirt at all."

I looked down. Hannah was right; my shirt was yellow - not my favorite, but laundry day was soon approaching - and it certainly didn't match the skirt.

"Come with me," Hannah said, and walked into her office. I followed.

Her office was very cozy. It had dark wood paneling on the walls, matching both the wooden desk in the center of the room and the wooden cabinets behind the desk. There was a chair between the desk and the cabinets and two more chairs in front of the desk. A full-length mirror was on the wall farthest from me.

Hannah opened up one of the cabinets and I could tell she was looking through some clothes. After a few seconds of searching, she said "a-ha" and pulled out a maroon turtleneck sweater. She turned to me and said, "take your shirt off."

I began to, remembered the bra underneath, remembered it didn't matter, and began fumbling with the buttons. I was bad at doing them in the best of things, and my nerves were shot after the adrenaline rush I had received earlier, so I could barely get them.

"Here," Hannah said as she walked around the desk and up to me, "let me help."

Undoing the buttons, I worked from the top as Hannah worked from the bottom. She was so close I could smell her shampoo, and the whole situation felt very intimate, especially as our hands met in the middle with us both grabbing for the last button at the same time. Hannah giggled and I managed a smile and giggle back as I let her undo the button, and I slithered the shirt off my arms and onto the floor behind me.

"Cute bra," Hannah told me. "You have good taste. But do you want one that matches your new thong?"

Surprised and still nervous, I couldn't manage any words to respond.

Hannah laughed again at my nervousness. "Of course you do," she said. She slowly slid her arms around my chest, under my own, and grabbed onto the back of my bra. "You trust me, right?" she asked, looking down into my eyes.

"Yes," I whispered back as she unhooked my bra. I let her slide it down my arms and off me.

"Good," she whispered back, throwing my bra onto one of the chairs in front of the desk. "You're very pretty, but I'm going to make you even prettier." She leaned in and gave me a slight kiss on my cheek.

I think my jaw may have dropped, but something in my pants - well, my skirt, I mean - was beginning to rise.

Hannah turned, searched through the closet for a moment again, and pulled out a lacy black bra that matched my thong. She walked back over and told me to hold out my arms, pulling it onto me and walking around behind me to hook it. As she came back around the front, I reached down towards the cups and tugged on them a little. All the bras I had ever warn didn't have cups, so it felt a little weird.

Hannah giggled at my fascination with the cups. "Yeah, sorry, sister. We're nearly exactly the same size everywhere else, but my girls are a little larger than yours." She grabbed her own breasts and shook them a little.

I gawked once again, and she laughed at my schoolboy reaction before grabbing the sweater. She had me raise my arms up and pulled it onto me.

"Oh, yes, that's perfect," she said after doing so, motioning again for me to twirl. I twirled, then she pointed me towards the mirror on the wall. "Come here and take a look."

I moved over next to her and looked in the mirror. I did look good. The skirt showed off my hips and butt, and the cups, though empty, gave me even more curve. The sweater fit surprisingly well.

"Why do you have all these clothes here?" I asked.

"Never know when you might need them," she replied. "Ooh! Wait." She turned back toward the cabinet. This time, she bent at the waist to grab something, and I watched as her skirt rose up the backs of her legs. It didn't go all the way up, but it showed off her beautiful legs in full and showed me that she was wearing thigh-high stockings held up with a garter belt, not tights.

She straightened up and turned back around, holding a pair of red heels. "Sit down," she ordered, pointing at her chair behind the desk.

I sat down, and she knelt in front of me, tenderly picking up my tights-clad feet and placing them into the high heels. "There we go," she said as she stood up, taking another look at me. But, before I could do anything, she held up a finger. "Wait - hold on a little longer."

She opened a drawer of the desk and pulled a few things out. I wasn't sure what they were at first, but then she pulled out a few more items, once of which I recognized as a lipstick tube. She was taking makeup out of the drawer and setting it on the desk.

"We're going to make you into a princess," she whispered. "Stay in the chair and close your eyes."

I closed my eyes and heard her picking up a few items before suddenly feeling her straddle on top of me. She had swung one leg over me and was more or less sitting backwards in my lap. I could feel her crotch directly on top of mine, and my dick started to swell again.

She began to apply different cosmetics to my face. I loved crossdressing but did it mostly in my home and had never really felt the need to mess with makeup, so it was new to me. It felt weird, but Hannah was gentle.

At one point, Hannah shifted in such a way that had her grind directly on my cock. I let out a small gasp in response to the sensation, and Hannah giggled.

"Do you like that?" she whispered.

"Yes," I whispered back.

Hannah began slowly rocking back in forth, rubbing her crotch on my dick. She did this for five minutes as she continued doing my makeup, eliciting more gasps from me along the way. It wasn't long before my dick was as hard as it could get trapped down in my panties and tights.

Before I knew it, however, I felt her get off me. "All done! Open your eyes," she said.

I opened them to see her finish pulling her skirt down. I guessed she must have had to hike it up to straddle me. I should have opened my eyes for a moment, I thought.

I stood up and walked over to the mirror. When I saw myself, I was in disbelief. Hannah had given me dark, smoky eyes; eyelashes that looked darker and, somehow, longer; shiny cheekbones; and hot pink lips. I turned. The heels made my figure look even better.

"I'm... hot," I declared.

Hannah laughed and walked up beside me, looking into the mirror. "Yes, you are, girlie." She put her arm around my waist and pulled me closer so our sides were touching.

I kept looking at myself and at us before giggling a little.

"What?" Hannah asked.

"With my short hair and flat chest, we look like a lesbian couple," I told her.

She laughed before looking over and into my eyes. "You know, normally I like boys, but I have to say you're the hottest lesbian I've ever seen." She spun me so we were facing each other and placed both hands on my hips before pulling me in for a kiss.

We kept kissing for a while. Hannah ran her hand up under my sweater on my back and rubbed sensually. My entire body felt warm. I was still nervous, but nothing would have made me stop.

Then Hannah pulled back. "Kneel," she ordered.

My heart skipped a beat, but I did as I was told. "Good girl," she told me, before grabbing the bottom of her skirt and pulling it up to her waist, showing me her white panties, which she promptly pulled all the way down and stepped out of. I stared at her shaved pussy. She slowly stepped toward me until her pussy was right in front of my face, then gently grabbed the back of my head and pulled me in.

I gently began licking her, aroused by her subsequent moans. I wasn't entirely sure what I was doing, but I hoped to make up for it with my eagerness. I began ramping up my licks and trying to stick my tongue into her.

"Fuck," she moaned in a breathy voice. She then pulled my head back by my hair. "Turn," she said, moving so I was between her and the mirror. "Pull your skirt up and your tights down."

I did everything she asked, my heart racing as I felt the cool air on my mostly bare ass.

"Yesss" she hissed. "I want to see your ass jiggle as you eat my pussy."

I went back to work, reaching my hand down to move my thong over and let my hard cock hang free. Hannah continued to moan as I licked, and she grabbed my head to hold it in place as she ground her cunt into my face.

Suddenly she pulled back my head again. "Up," she said.

I stood again and she pulled me in for a kiss, running her hand down my cock. I moaned into her mouth due to the touch.

She broke off the kiss and pointed at the chair she'd done my makeup in. "Sit."

I sat.

"Good girl," she cooed, before straddling me like before, but this time, her panties were off, my panties were pulled to the side, my tights were pulled down to my thighs, and both our skirts were up - nothing was between my hard cock and Hannah's dripping pussy.

Gently, she grabbed my dick and guided herself down on it. We effeminately moaned in unison.

Hannah began to slowly ride me, bending down to kiss me as she did so. Fireworks went off in my head at the sensation.

"Take my shirt off," she whispered to me.

I could barely focus, but I began to undo the buttons on her blouse. I knew I had to hurry because I knew I wasn't going to last long. Somehow, I had some success with the buttons, and the whole thing was off before long.

I grabbed her boobs with both hands and squeezed as she stuck her tongue into my mouth. Hannah increased her riding pace and I heard her thighs begin to plap-plap against mine. The sensations from my lips, hands, thighs, and cock bombarded me; I was drowning in pleasure.

But, far too soon, I realized I was about to cum. I tried to hold it in, but I was hopeless in the face of my burning lust. With a girly moan, I came, wrapping my arms around Hannah to hold on.

Hannah gasped as my cum entered her, before saying "oh, fuck! I'm cumming too!" and gritting her teeth. She continued to ride me up and down a few more times before finally coming to a stop all the way down on my cock. Panting, she kissed me again.

Then, she stood up next to me. By now, from head to toe, all she was wearing was her bra, hiked-up skirt, garter belt, stockings, and heels. "Fuck, Johnnie," she said. "That was great."

I smiled back. "Yeah. That was... amazing."

However, Hannah threw up her hands. "But now you're all sweaty and gross! We never really got to see you all dolled up!"

I giggled sheepishly. "I think it was worth it."

She giggled back. "Yeah, probably." She thought for a second, then looked at me. "Hey! You should come over tonight."

"Really?" I asked.

"Yeah! Unless you have plans-"

"I don't," I said immediately.

She giggled again. "Yes, it'll be perfect! You can come over and have access to my whole closet. You can wear whatever you want! We'll have a little fashion show and I can take photos." She grinned seductively at me. "And maybe we can keep our hands to ourselves until the very end."