In My Boss' Skirt Ch. 02

We pulled into the driveway of Hannah's house will a soft bump. Her home was a generic subdivision house, mostly brick, with dark green fake shutters around the windows and a one-car garage.

Hannah shut off the engine and looked over at me, smiling. She hadn't bothered to button her blouse all the way up when we'd re-dressed at the office, and I stared at the cleavage that peeked out.

"It's not much," she said, bringing my eyes back to her face. Her hair and makeup looked a little disheveled thanks to the sex we'd had at the office, but she was still beautiful.

"Hey, it's nice," I told her in response, looking back at the house. "Looks a little more spacious than my apartment."

She laughed and began to get out of the car. I opened the door to do so as well and gingerly swung my feet on to the asphalt, still not remotely used to wearing high heels. I stood up and closed the door, balancing myself against the side of the car.

Hannah saw me and laughed again. "Need any help?" She walked around to my side of the car and offered me her hand.

I probably could've made it inside on my own, but I took her hand anyway, not planning on saying no to touching her. Holding hands, we walked up the driveway to the door, which Hannah then unlocked, allowing us to enter the house.

The inside smelled good - it was a gentle floral scent, though I wasn't sure what exact flower. We didn't stop, though, as Hannah pulled me over to the stairs and then slowly ascended them with me, letting me take my time so I didn't slip and fall all the way back down as I wobbled in my heels.

"It gets easier," she told me as we neared the top. We were still holding hands.

"It had better," I told her. Finally, we reached the top floor.

We went down the hall and went into Hannah's bedroom, which had red wallpaper and was a bit of a mess. The bed wasn't made (though neither was mine back home) and there were dirty clothes strewn on the floor (also like my home) along with a couple of empty beer cans (yet again just like my place).

"Uh, sorry," she said when we saw the mess, embarrassed. "I didn't, uh, expect to have company tonight."

"It's fine," I told her, laughing. "Trust me, I'm no better."

I was wondering if we were going for the bed, but Hannah instead pulled me towards a door on the left side of the room. We slipped in and I discovered it was the bathroom. There were two sinks side-by-side, and the counter was covered in stuff.

"Uh, don't worry about the mess," Hannah said, clearly not taking her own advice. But then she turned towards me and her eyes narrowed a little. "Strip," she ordered.

I glanced at myself in the mirror and saw my own makeup was also messy. As told, I bent down and took off my heels, then unzipped my skirt and pulled it off. I yanked off my sweater, then peeled my tights off.

Looking up, I saw Hannah was also stripping, and I stared at her breasts as she took off her bra. I tried to reach around behind myself to take my own off, but I couldn't seem to find the hooks.

"Here," Hannah said as she stepped out of her panties and was now fully nude, "let me help you." She stepped over and wrapped her arms around me. I felt the bra unclasp and then she pulled it down my arms. After dropping the bar to the floor, she hooked her fingers into my thong and pulled it down my legs, letting me gently step out of it as she reached the floor. "There you go, baby," she told me as she stood back up, and I felt myself get a little aroused.

Hannah reached into something on the counter and handed me a wipe. "Wipe your face with this," she told me, pulling out another for herself. "It's makeup remover."

I did as I was told and wiped my face with it. Sure enough, it wiped away a lot of the makeup I was wearing, and I felt a little pang as the usual, boring me shone through again.

Then, Hannah walked past me to the shower and leaned in to turn it on. I bit my lip as I stared at her jiggling ass as she faced away from me, then swallowed hard when she turned back around to face me.

"If we're going to play dress up, we need to get cleaned up first," she told me. "We both look like sweaty messes. And" - she looked down at her crotch, my eyes greedily following hers - "I need to wash your cum out of my vagina."

"Um... sorry."

She laughed. "Trust me, I'm not complaining." Hannah then reached into the shower to feel the water. "It's warm." She reached her other arm out to me. "C'mon, get in."

I walked over and took her hand and she helped me into the shower, then pulled the curtain closed behind us.

Suddenly, the world was very small, just Hannah and I underneath the warm stream of water. Facing each other, she put her hands up on my shoulders, and I gently put my hands on her hips. Her brown eyes looked beautiful. Then, she leaned in and kissed me on the lips, and I closed my eyes and enjoyed the warmth of the water and of Hannah.

We kissed like this for a moment before Hannah turned around and grabbed a bottle of soap. Turning back to me, she squirted some soap out of the bottle into her hand and then some into mine.

She rubbed her hands together for a moment to get them both ready, then started running them over my body, caressing my shoulders and chest. I got the message and immediately started washing her boobs, causing her to giggle and call me a naughty girl.

We continued to wash each other, and between Hannah touching me and me touching her, I found myself rock hard.

"Hmmm," said Hannah as she gently stroked my penis, drawing a moan from my lips, "we'll have to do something about this. You won't fit so well in my panties and skirts and dresses if you've got this sticking out, will you?"

Suddenly, she dropped to her knees and, to my surprise, took my cock in her mouth. I moaned immediately as she began sucking and put my arm out to brace against the wall.

"Ooh, Hannah," I moaned as she licked my shaft, my voice high and girly. "Oh, fuck."

She kept sucking for a few more minutes and my knees began shaking as I got closer and closer to climax. All too soon, that familiar feeling began building my cock, and I whimpered, "fuck, Hannah, I'm going to cum."

Hannah took her mouth off my cock and began stroking it wildly, angling her chin underneath and sticking out her tongue. With a final moan, I erupted, shooting cum on Hannah's face. After a few ropes of cum came out, I was so overwhelmed by the orgasm and seeing Hannah's beautiful face all covered in cum that I nearly fell over.

"Oh my god that was hot," I said, still bracing myself against the wall.

"Mhm," agreed Hannah, angling herself so the water began to clean my jizz off her face. "I've never gotten a facial before, always thought it would be such a pain to clean up. So I figured this was the best opportunity."

I didn't really know what to say and hardly had the energy to respond anyway.

We finished washing off and got out of the shower. Hannah handed me a towel, and when I started to tie it around my waist, told me "cover up those tits, you slut!" I wrapped it around my chest as best I could as she did the same with her towel. I loved the feeling of the cool air on my legs.

"Alright, time to reapply makeup" she told me. "You're just going to have to stand, I don't have a chair."

"That's fine," I told her. I positioned myself in front of the counter and closed my eyes, letting her go to work.

It wasn't long before she told me I could open them again, and when I did, the hot woman from before was looking back at me.

"Wow," I said. "That really is impressive."

"Thanks," she told me. "Now let's find you your first outfit to wear."

She took my hand again and led me back into the bedroom, around the bed, and to a door on the other side of the room. She opened it to reveal a walk-in closet filled with her clothes.

"Wait here, actually," she told me. "Better yet, sit on the bed."

I sat on the edge of the bed, crossing my legs so no one could look up my towel. Hannah slipped into the closet, emerging after a moment with a pink dress that she laid down on the bed beside me. She then moved over to a chest of drawers next to the closet door, opened the top drawer, and pulled out a pink thong that she laid on top of the dress.

"Oh," she said, "one more thing."

She went back into the closet and returned a few seconds later with a black set of heels that she set on the floor next to me.

"OK," she said. "Get dressed. I'm going to put on some makeup myself, and then I'll be back."

Hannah went back into the bathroom. I gingerly took off my towel and let it drop to the floor, then grabbed the dress. It was strapless, short, and sparkly. I raised it above my head and pulled it down, having to fight it every inch because it was so tight. With one final tug, I got the hem past my ass and smoothed it out. The dress was barely decent, coming only down to the tops of my thighs.

Next I strapped on the heels, then stepped into the thong and pulled it up. It didn't cover me that well in the front and the back part wedged itself into my ass crack. It wasn't super comfortable, but it made me feel slutty as hell.

"Oooh, looking good, girl!" said Hannah behind me. I turned around to see leaning against the bathroom doorframe. She had applied some light makeup. "Mmm. That dress hugs your curves so well."

"It's really tight," I agreed. It felt like someone had wrapped me in something from the top of my chest (or tits, some might say) to the bottom of my ass.

Hannah grabbed her phone. "Let me take some pictures!"

I was immediately nervous. "Are- are you sure?"

"Yes, babe!" she told me. "You look hot! Isn't this what you came over for?"

"Uh, I guess," I told her, still anxious.

For the next few minutes, Hannah gave me directions as to how to pose, sticking my ass out and blowing kisses to the camera and the like. She then showed me the photos.

"I can't believe that's me," I said as we looked at them. I looked gorgeous.

"It is," Hannah told me. Suddenly, her stomach rumbled. "Oh my gosh," she said, embarrassed.

I laughed. "Hungry?"

She smiled sheepishly. "Yep." Her smile turned a little more sinister. "I guess I should have swallowed in the shower."

I felt myself blush.

"Let's order pizza," she continued. "Oh, but before that, let's get you into something a little more comfortable." She went over to the chest of drawers and pulled out a little pile of pink clothing. "Put all this on."

Sorting through the pile, I found it was a lacy lingerie set with a bra, cheeky panties, a garter belt, and thigh-high stockings. I yanked the dress off and took off the heels and thong, then went to work on the lingerie. I hooked the bra strap in front of me, then spun it around, put my arms through, and pulled it up into place.

"Where'd you learn how to do that?" Hannah asked. She'd taken off the towel and was now naked as she searched through the chest of drawers.

"Uh," I told her, blushing again, "watching porn."

She laughed and pulled some red clothes out. I went back to work, pulling the stockings up my legs and clipping them to the garter belt, then pulling the panties on. They neatly covered my cock and balls. When I was done, I decided I wanted a little more and put the heels I'd been wearing back on.

Looking up, I saw Hannah had put on a matching set of lingerie, though hers was red. It left little to the imagination, and she looked incredible.

"Thank goodness I got that buy-one-get-one deal, huh?" she asked me, before noticing my heels. "Ooh, good call."

She dipped into the closet once again and emerged wearing a white pair of heels that made her just as tall as me. "Alright! Let's go downstairs and chill out for a little bit."

We did just that (I still took the stairs slowly), sitting on her couch and turning the TV on. There wasn't much on, so I turned it to some true crime show. Hannah ordered pizza and then grabbed a blanket to cover us up, as it was a little cold in her house to be wearing so little. We sat underneath the blanket together with no room between us, holding hands.

Sooner than I expected, the doorbell rang. "That must be the pizza," Hannah said. Then, she looked at me. "Go answer the door."

"Me?" I asked, a pang of anxiety shooting through my stomach.

"Yes, you," she replied. "Be a good girl and answer the door."

Shakily, I stood up and walked over to the door, trying not to trip or panic. My hand was nearly trembling as I unlocked the door and slowly opened it.

There was a man in a black collared shirt on the other side holding a pizza box in both hands. "W-wow," he said, looking up and down my lingerie-clad body. "I thought you were kidding."

"K-kidding?" I asked.

"About the note," he said. I was terrified by the lust in his eyes that continued to roam my body. "In the notes section on the order, we get people kidding all the time, 'oh, I'll answer the door naked' or whatever. So when I saw 'I'll be in lingerie and I'll tip you with a kiss' on the note for this order, I thought you were kidding! But here you are!"

"Oh," I said quietly, glancing over my shoulder to see Hannah grinning wickedly at me. That motherfucker, I thought.

"So, uh, here's your pizza," said the delivery guy. He offered it to me and I leaned forward to take it from him. Our eyes locked, and I swallowed before leaning in all the way to give him a gentle kiss on the lips. "Thanks," he told me, smiling. "Feel free to order again whenever." There was a slight tint of pink on his lips thanks to my lipstick.

I smiled weakly back, then shut the door and walked back to the couch, wobbling in my heels on the carpet. I sat back down and put the pizza box on the coffee table, and looked over at Hannah, who was grinning from ear to ear.

"Shut up," I told her.

"I didn't say anything!"

Hannah put on a horror movie and we ate dinner as we watched. It wasn't long before we were through with the pizza, so we got back underneath the blanket. Hannah curled up beside me, rested her head on my shoulder, and began to rub my thigh, playing with the garter belt strap and the hem of my stockings.

After a minute or two of this, I decided to return the favor and began to do the same to Hannah. Hannah's other hand slipped out from underneath the blanket, grabbed my chin, and turned my head towards her. She raised her head up and we kissed deeply.

I decided to up the ante and moved my hand from her thigh to the front of her panties, rubbing her pussy through the fabric. She moaned and grabbed my thigh, and then I snuck my hand inside her panties and began stroking her wet cunt directly, causing her to moan even louder.

"Fuck, baby," she whispered. "Oooh..."

My dick began to rise in my panties as Hannah kissed me again. When we broke off, I suddenly slid off the couch and onto the floor between Hanna's legs, still covered by the blanket. Feeling around to find her crotch, I began kissing the insides of her thighs. She gently lifted her butt up and slid her panties down to her thighs, then sat back down.

I went in and began licking Hannah's pussy, drawing a "oh, shit," from her. Starting slow, I ate her out, enjoying every moan and whimper I heard coming from above me. I sped up, licking more aggressively and trying to stick my tongue in. Hannah's breathing got harder and harder until suddenly she grabbed the back of my head and pushed my lips into her cunt, squeaking "oh fuck, I'm cumming!"

Long moans followed, so I kept licking until she finally released her grasp on my head and went limp on the couch. Wiping juice from my chin, I slithered up her legs and sat on her lap facing her, my dick tenting my panties.

"Oh my god, baby," Hannah whispered, kissing me. "That felt so good." She looked down at my crotch and giggled. "Looks like somebody else wants a turn."

Now it was my turn to lift my hips up and pull my panties down. Hannah began stroking my cock and asked me to take her bra off, so I reached around her and began to fumble with the hooks. Thankfully, it didn't take long and I managed to pull it off her.

"Sit up," Hannah told me. I pushed my hips up so my thighs were pointed straight down and my dick was level with her tits. She gently took my cock and placed it in between her boobs, then clamped them together and began to rock back and forth, moving her rack up and down my dick.

I'd never received a titjob before and whimpered as she massaged my penis. Despite having orgasmed twice that day, the cuddling and pussy eating had me ready to go again, and now, looking down at Hannah's face as her breasts bounced up and down around my cock, I felt another climax coming fast.

"Ooh, mommy," I moaned, and suddenly my dick throbbed, shooting cum all over Hannah's tits. I panted like a dog as I came, and when it was over, Hannah let go of her tits and licked the tip of my penis, causing me to flinch in pleasure.

When she finished, I sat back down on her lap. Hannah looked down at her breasts, then up at me, smiling. "We're going to need to shower again."

I nodded, smiling back.

"But that can wait until tomorrow," she said. "It's late, and I'm wiped out."

I nodded again, realizing just how tired I was too. I slid off her and stood up, nearly rolling an ankle in my heels. Hannah giggled at me, then, after we each pulled our panties back up, took my hand again.

We went back upstairs and into Hannah's bedroom, took off our heels, and collapsed into her bed, spooning.

"Goodnight, Hannah," I whispered into the back of her neck.

"Goodnight, girlie," she replied. I smiled and fell asleep, our stocking-clad legs rubbing against one another.