Pleasing The New Boss

I started in the workforce when I was 20. Through 5 jobs for 4 companies over 15 years, I had never had a female boss. Blame the glass ceiling, not me. I would rather work for a competent woman than an incompetent man any day.

So I was delighted when I heard that my manager was being fired for "misuse of his work phone" (read: watching porn on it) and he was being replaced by Rebecca, the former manager of another branch.

I'd only met Rebecca - not, she would stress Becka, Becky or Bek - several times at conferences or work functions, but she'd always seemed pleasant, and I'd never heard a bad word about her management of her staff. I was relieved. My job often had me working late on projects, often directly with my manager. I figured Rebecca would be sure to make this easier than it had been under my former boss.

She was divorced with one kid, I remembered. I was married so thoughts of any romantic entanglement were the furthest thing from my mind.

It was six weeks before we slept together.

It's not a funny story, nor an original one. It's not even a story I'm particularly proud of. A two night stay at a hotel for a conference, too much booze, too little willpower. She was pushy and demanding. Loud and completely without abandon. I loved every second of it, but I felt like shit in the morning.

I rolled out of her bed and squinted at the red digits on the alarm clock on her side of the bed. 7:02am. I found my shirt. Wrinkled to hell. I'd have to sneak to my room and put on a new one before breakfast. I pulled it on anyway - better wrinkled than half naked - and looked around for my boxers. As I searched under the covers on my side of the bed, I looked up and noticed Rebecca looking at me. I apologised for waking her and explained what I was doing. With a sly smile, she said three words that changed our relationship forever.

"Just wear mine."

I'd never worn women's underwear before then. I had never thought about it. But when I laughed and continued looking for my boxers, Rebecca gave me a stern look and said in her best manager's voice

"I'm serious. Wear mine. The ones from last night." Her black panties were a dark patch on the carpet in the gloomy room. I picked them up, my face bearing a quizzical look. Rebecca reached out and took them. She sniffed them and handed them back "They smell like me. Wear them today and I'll fuck you again tonight."

With that, she rolled over and went back to sleep.

Somewhat sheepishly, I pulled her panties up my legs. I was used to boxers and these were - I would learn the styles later - bikini briefs. They did indeed smell like her. I could tell even as I pulled them up and awkwardly adjusted my balls. I put on pants, gathered my shoes and socks and whispered "See you at breakfast." Rebecca gave no reply.

My own room was across the hall and a few doors down. It was too early for anyone from the office to be heading to breakfast just yet, especially after the night we'd had, but I scurried as fast as I could anyway. Once inside I took off last night's wrinkled shirt and pulled off my trousers. I caught a glimpse of myself in Rebecca's black panties. They were simple, almost businesslike, but also somehow distinctly feminine. Just like Rebecca, I thought.

I slipped out of the panties and hung them on the hook on the back of the bathroom door, where my eyes drifted often as I showered. Memories of last night came back to me as I washed: Rebecca's tan lines, the taste of my own cock on her tongue, the pattern my cum had made when I jerked it onto her ass. I was hard as I toweled off, but a sudden pang of guilt ran over me and my cock went limp.

"Wear them today," I heard Rebecca's voice in my head and looked over at t panties on the hook "and I'll fuck you again tonight."

Had she meant that? Did I even want to? Last night had been a mistake. A one-off thing I could spend my life justifying and blaming alcohol, but twice was no mistake. This would be calculated, premeditated. Even if I could justify last night, this would unmistakably be cheating on my wife. This would be...

...Rebecca spitting on my cock before plunging her mouth over it. Her dark nipples like braille under my thumbs. The breathy way she said 'cunt'.

I reached out and took the panties off the hook. Five minutes later, I was buttoning a fresh shirt and leaving my room on the way to the breakfast buffet with my semi-hard cock squeezed into a pair of women's black cotton bikini briefs. It might have been my imagination, but they felt warm.

My heart was pounding as I rode the elevator down. I could barely concentrate on what anyone was saying as my colleagues trickled into the hotel restaurant in ones and twos. The pairs were exclusively of straight men and straight women. If you didn't know better, you'd swear no-one at all had hooked up last night. But if you looked closely you could see furtive looks between couples - and I was watching everyone closely, paranoid that someone was about to point at me like Donald Sutherland in that alien invasion movie and scream "paaaaantiiiies!"

I almost jumped out of my skin as a pair of hands grabbed my shoulders from behind. I realised that I could now recognise Rebecca's shampoo as her hair brushed my face. She put her burgundy lips close to my ear and whispered.

"Are you wearing them?"

"Yes."

"Good."

That was all. Rebecca walked away to join some other coworkers at the coffee station.

Day two of the conference was a short day and wrapped at 3pm. Rebecca had done a presentation, never making eye contact with me at all while she was on stage. When she was done, she took a seat in the front row and I spent all day staring at the back of her head, remembering how my hand looked tangled in her wavy, dark hair. At lunchtime, she appeared next to me as if by magic and asked simply if I was up to it tonight. As simple as that. I took a moment to answer, but we both knew I was going to say yes. She smiled and wandered away.

About half of my colleagues had checked out that morning so they could leave as soon as the conference was over. Most of them had families to get back to, some just hated being there. I had taken the offer of the room for the second night for no reason other than my wife was visiting her parents and there was no special reason for me to go home right away. Those of us who remained went to the bar, of course. By 9pm there were four of us left, Rebecca, myself and two men - one of whom was certain he was going to score with Rebecca.

As my male coworkers started a game of pool, I went to pee and Rebecca went to the bar. As I returned from the men's room I noticed she was empty handed. She caught up to me.

"I've ordered us room service to my room. I'm heading up. Make your excuses and join me in fifteen minutes."

Twelve and a half minutes later, I was knocking on her door. As soon as it was closed behind me, Rebecca gave me a wicked smile.

"Let's see you."

I unbuckled my belt and unzipped, then quickly reversed the process when the room service arrived. Only as we sat down to eat did I realise that Rebecca had ordered for me. A club sandwich and fries could have just been a good guess or a stab in the dark, but it was good and I was hungry. Rebecca sat opposite me at the tiny hotel room table and asked me if I liked my position at work.

I told the truth. I enjoyed working with her and for her. I liked the work and most of the people. I liked the office's location, a short commute from home. At the mention of home, Rebecca had another question, "Are you happy there?"

Again I spoke the truth. I loved my wife, but for the last couple of years we'd treated each other like side projects, our work, hobbies and even our friends seeming to come before each other.

"How often do you fuck?"

For some reason, the question didn't surprise me. I knew the answer right away, "Maybe once every month. Six weeks, sometimes."

Rebecca nodded as she ate a fry. "I'm going to be honest with you, Scott. I don't usually mess around with married men. Too many...complications." She made a face. A look of distaste. "But...You wore my panties today. You could easily have not worn them, and you certainly could have not put them back on after showering. But you did."

"You said you'd..."

"Yes, I said I'd fuck you again. And I will. But you could have turned that down too. Or not worn the panties and taken your chances at trying again."

"That doesn't seem fair."

Rebecca stood and pushed her chair in "Every weekday, after hours. Every convention or conference that we both attend. If the Christmas..."

"I'm sorry, what are we talking about now?"

Rebecca looked at me like a teacher looks at the slow child in class, "Every weekday morning, you will put on the panties I wore the previous day. Every weekday after hours, we will engage in some sexual activity that satisfies me at least, and both of us when time allows."

I started to say something, but I could not to this day tell you what it might have been. "I..."

"Conferences and conventions, we will get two rooms. We will always use mine."

No slinking down the hall in yesterday's wrinkled clothes for her, I thought.

"When the Christmas party is held off-premises, conference and convention rules will apply. Unless of course your wife is present."

Rebecca was undressing as she spoke. She was down to her bra and panties. Fancier than last night, a matching black and white set with lace. She motioned for me to stand.

"Let's see them."

I sat on the end of the bed and undressed. Rebecca removed her bra; olive skin, tan lines, dark nipples stiffening as I watched. I sat with my cock straining at the cotton of yesterday's panties. Rebecca knelt and buried her nose in my crotch, breathing deeply.

"Mmmmm, do you love the smell of my cunt?"

"I do."

She stood and pushed my face into her panties. They were damp and warm against my nose. "Do you?"

I licked her pussy through the fabric before repeating, "I do."

My boss knelt again and pulled my cock out the leg of the black panties. It was uncomfortable and we fumbled a little to get it right. But when I settled back, she swallowed my cock in one go and all was right with my world.

My wife hated giving head. She'd do it reluctantly on my birthday, or if she thought it might stop me asking when we were going to have sex again. Suck suck, stroke stroke, taking my load on her chest. But Rebecca, my god. She'd given me the sluttiest, sloppiest blowjob I'd ever had the night before and now, with the whiff of her own pussy in her nose, she gobbled my cock like her whole life had been leading up to this point. After a minute or two, the awkwardness of my cock poking uncomfortably through the side of the panties made things difficult so we both stood and took off the panties we were wearing.

Rebecca laid me back on the bed and draped the damp black and white lacy pair she'd been wearing over the lower half of my face. Then she shimmed up and knelt over them before lowering her pussy and humping my face with the panties between us. With no regard to my comfort, she writhed and bounced on my face until she soaked the panties that covered my nose and mouth. My cock was so hard I could feel my pulse in it. My whole world was reduced to the smell of my superior's musky cunt. She slid back and I pressed the wet panties to my mouth, sucking gently. Rebecca reached down and shoved part of them into my mouth, gagging me.

With a few wiggles, she slipped her pussy over my cock and slid down. I moaned against the lacy gag in my mouth. Rebecca rode me slowly, with languorous, rhythmic thrusts of her hips. I watched as her meticulously-trimmed cunt swallowed me over and over. I felt my orgasm building and was never so happy that my wife had insisted I get a vasectomy years ago.

"I'm gonna cum!" I muttered into her panties.

Rebecca must have understood as she picked up the pace of her thrusts, "In my cunt."

"In your cunt." I repeated, muffled.

"In Rebecca's cunt...say it. Say my name!" She reached down and removed the panties from my mouth.

"Oh. Fuck. Rebecca. I'm gonna cum in your cunt"

"Will you wear my panties? Say it."

"I'll wear your panties."

"Every weekday. Christmas. Conferences" Each word punctuated by a rhythmic motion. Her ass brushing the tops of my thighs.

"All the time. As often as I can."

Rebecca closed her eyes and put her head back. "You're mine now. Cum in me. Your mine. Say it. Say my name!"

"I'm yours. Rebecca. I'm yours. I'll wear your panties. I'll eat your pussy, your ass. Fuck. I'll cum in you. I'm gonna..." But it was done. I was cumming. Rebecca was bouncing hard and fast, milking me, tugging my cock with her pussy. I came so hard I felt like my soul was shooting into her. Rebecca came with me, her pussy flooding over my hips.

"I'm yours. I'm yours" I kept repeating. "Fuck. Rebecca. I'm yours."

That night was a little over four years ago. My wife and I divorced a year later, for completely unrelated reasons. As far as I know, she remained unaware. I remained a model employee, arriving early to meet my boss with coffee, changing into the panties she'd worn the day before and brought to work in a ziploc bag. Sometimes they're wet, sometimes very wet. if I displease her, she threatens to piss in them and make me wear them, but so far she hasn't followed through. If I please her with my work, she makes me wear a thong, but when I wear a thong, she always lets me fuck her. Otherwise, as long as I make her cum, we're both happy.

Yesterday she informed me that she bought a new toy: a seven inch, bright pink strap-on dildo in a black faux-leather harness. I'm wearing pink cotton tanga panties, with cute bows on the hips. She's smearing lube on the toy and asking who I belong to.

"I'm yours."