Who's the Boss Now?

Story Info
Sex with a work collegue who was my female supervisor.
2.6k words
4.45
12k
11
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
verbiage55
verbiage55
45 Followers

When I was 28, and before I became a writer, I was working a junior-level civil engineer. I was employed by a firm that specialized in bridge design. My immediate supervisor -- my boss -- was a single, 40-year-old woman named Diana.

She was brilliant. Not only was she the most innovative design engineer in the firm, but she was also a pilot and had an incredible mechanical mind. She actually built (and flew) her own airplane. She had to install an engine, which she took from a used Porche and adapted the kit to house it. It was a kit plane; but still, she built an airplane!

She was a tough, but fair, boss. Not mean, but definitely demanding, and very much "the boss." She let me, and everyone else who answered to her, know that she was the one in charge and giving the directions -- and you were expected to follow them without question. Period.

She wore the pants in the office. Literally and metaphorically. She always wore jeans to work unless she was required by our CEO to attend a client meeting, then she came to work in a skirt. She always changed back to jeans after the meeting.

Despite Diana's hard-ass work personality, I enjoyed chatting with her when not working. We had several common interests. So, we occasionally had lunch together and more rarely went out after work for drinks with several other employees. Then, on one occasion, we found ourselves alone -- just the two of us -- at our usual happy hour watering hole. It was a dive bar only a mile from work, and half-way between her home and our office.

After a couple of cocktails (okay I had three or four) we decided to leave. Walking to our cars, with me following her, I suddenly noticed how good her ass looked in those jeans. Silly as it sounds, I don't think I had ever thought of her as a woman before. She was just my boss, 12 years older, and an infallible senior engineer. Not a sexual object.

When we got to her car, she turned to me to say, "Good night, drive safe." And then I did something spontaneously insane. I leaned in and kissed her. I honestly don't know what I was thinking at that moment. I guess I wasn't thinking. I could have lost my job. I was a bit drunk, and my testosterone had kicked in when I saw that ass swaying in front of me. It was like a red cape to a bull. And I charged in.

When I kissed her; she kissed back. Passionately. With tongue. Talk about a greenlight! And I hit "go". I cupped her ass with both hands and we started to make out while standing, right there in the parking lot. Lust had overcome me. I removed my right hand from her butt and cupped her pussy mound. I think I would have fucked her in the parking lot at that point. But she was less drunk and far more sensible.

She stopped kissing me and said simply and forcefully, "Get in the car. My place is just a mile from here." And that was the last bossy thing she said or did for the rest of that night.

She drove us home in silence with my hand resting on her leg like we were a loving old married couple. But five minutes later, we were making out again at her front door while she fumbled for her house key.

We stumbled through the door and I took off my jacket and casually hung it on a rack by the door. She dropped hers on the floor. She was wearing jeans and a simple button-down shirt.

I kissed her and immediately started unbuttoning her blouse. I was wasting no time. But she did not seem to mind.

The next thing I knew, she was fully naked and I was shirtless and in bare feet. But I do not remember now how that happened. I can't recall any of our clothing coming off. Yet somehow it did... And now she was standing in front of me, nude. She placed her palm flat on my chest and her expression seemed to suggest she also wondered how she got naked.

I start kissing her far more passionately. She felt my fingers parting her as we stood and she moaned softly. She was no longer the boss of me. Intending to embrace her, we accidently stumbled backward in a clumsy Tango. We bumped into a big leather ottoman and club chair in her living room when the backs of her knees collided with the ottoman. I dropped to mine and buried my face into her fully engorged pussy. It smelled fantastic. I breathed her in deeply.

I think she started to say, "Fuck me..." But then gave in to the pleasure as I started licking her slit. Since I seemed to be truly enjoying the activity, she left me to it. Then I found my mark and rubbed it long and hard.

My tongue was still on her clit as I brought her to orgasm. That was crazy fast, I thought. Knowing her climax was on its way, I had the forethought to unzip my jeans. At the very moment she started to come, I was between her legs and in her, with my pants still on. She finished her orgasm with me fully deep inside her.

She sort of purred in pleasure as we moved together, kissing as we did so. I could feel her pussy contractions in waves. I wondered if that was another mini-orgasm, or just the final vestiges of the first one echoing within her.

I decided it was time to give her another big one. I alternated between doing her orally and fucking her in a slow, mercilessly prolonged way, not allowing her to complete the next orgasm from either form of stimulation before switching to the other. Her body language made it obvious she wanted me to continue fucking her to completion. So, I stopped, stood, and finally fully removed my pants.

With the oversized ottoman pushed against the club chair we had a perfect little bed. She stretched catlike, adjusted some throw pillows, laid back, and got comfortable. I slid up and was in her again. We rocked our hips in unison for some time, with more enthusiasm for the kisses than the fucking.

I stopped kissing her and buried my face in her neck. Her hair smelled great. I slid my hands under her ass and cupped both cheeks just as I did in the parking lot. She pushed her pelvis into me hard, just as she had done in the parking lot. I realized this was our first non-verbal communication of certainty. It said, "Yes, I want you to be dominant. Give it to me hard." She would never be the boss of me outside of the office from now on.

Alternating between fast and slow penetration, I matched my fucking pace by pulling her ass up and into me as I pushed my own ass down. She slid her own hands down my back and begin to pull me into her, with each pull matching my own hip thrust. It was if she was using her hands to say, "Fuck me. Fuck me. Fuck me."

We were now in perfect sync. Shallow push. Deep push. Hold for a breath. Slide out. Shallow push. Deep push. Hold a breath. Slide out. Repeat. Repeat. Repeat. Ad infinitum.

Once the fuck-thythm became automatic, I removed my hands from her ass without changing our pace. I arched upward and reached for her arms. I slid my hands down to her wrists without breaking the rhythm. I raised her arms upward so her hands were palms up above her head. She was constrained ever so briefly as I held her down firmly by her wrists -- but only for mere seconds. It was just long enough for her to feel overpowered by me, but not in a scary way. I now was saying, "I own you." Without speaking a word.

I kissed Diana passionately to let her know I was going to dominate her in a gentle way. Then, I relaxed my grasp on her wrists and moved my hands lovingly on top of hers. Our hands were palm-to-palm -- with fingers matching fingers as if we were comparing our hand size.

I then pressed my thumbs into the center of her palms and massaged them in tight little circles. Firmly. As a did so, I broke our hip rhythm and pushed into her as deep as possible as I rotated my hips slowly. My cock pressed her cervix in a movement that mirrored my thumbs on the center of her palms. The corresponding pressure suddenly made her hands into newly discovered erogenous zones. Like buttons that turned up the arousal volume.

As I fucked her in these tight little circles, she began to rhythmically hip thrust upward. Her movement was like a bass player playing a new rhythm in counterpoint to the drummer. I responded to her improvisation. With each slow thrust she made, I pushed my thumbs into the palms and pushed my cock in hard. And then I reduced the pressure in equal measure to her metronomic hip thrusts. Once the new rhythm was jointly established, our pace began to quicken. We were both going to come. Very soon.

I released her hands and grasped Diana around her shoulders, cradling the back of her head in one hand and hugging her with the other arm as our pace quickened toward orgasm. Like an accomplished jazz musician, she added another layer of intrigue to the rhythm. Her pussy started to contract in syncopated waves that were further enhanced by my thrusts. The drums and bass were now joined by her vocals. She was coming. And hard!

The waves of pleasure washed over me. Literally. I did not come, but rode her rhythmically to a standstill. Now it was my turn. I wanted her to concentrate on me squirting. I want her to be attentively focused on the contractions, as my cock pulsed hot cum deep inside her.

I rarely speak during sex. But I now broke that silence to give very clear instructions: I said, "Turn around. I want you from behind." I was clearly the boss now. I directed her to get on her knees on the ottoman and lean her elbows on the club chair. She shuddered when she turned and raised her ass to me. I mounted her like she was my mare.

I tend to come very quickly in this position, so I save it for the finish. I feel very "alpha" when doing it doggie style, and that arouses me to a quicker climax. It is so deep in this pose, and I can completely dominate a woman in a very primitive male way. And I now knew that is what Diana prefers. She controls everything in the office, but in bed she wanted to be "my bitch".

She buried her face in the chair and rocked her butt slowly from side to side as if to signal me: Is this what you want? I mounted her quickly and pounded hard. I took a firm grasp of her hip bones and pulled her ass into me as I humped her. I was pushing her face into the pillow, but I could still hear the muffled moans of what sounded like yet another orgasm underway.

My right hand was wrapped around her waist fingering her clit as we fucked, while my left was attempting to grasp a handful of her tussled hair. I was totally dominating Diana physically. She was still making muffled screams into a pillow, but I just ignored them and drove harder. I felt her cunt contracting as she pushed her ass back against me.

She fell completely silent, but was either having orgasm contractions, or consciously kegeling me. Either way, it felt wonderful. Her juices were dripping onto the ottoman. I was pushing hard forward and she was pushing back. Both in equal effort. The physics of this action ensured we were completely still and completely linked in an equilibrium of opposite forces. I was no longer moving but as deep as I could possibly be thanks to us pushing against one another. My dick pressing hard against her cervix. She was full of cock.

The power of the contractions became overwhelming. And, because I was completely motionless, I could fully appreciate them. It felt like she was sucking my cock with her pussy. I cannot resist the compliment her body was paying to mine. So, I said, "thank you" in the most direct way I knew: I came inside her.

It is unusual for me to actually feel the internal pressure as my cum squirts out. But, I was so fully enveloped by the contractions that I could feel each squirt as it matched her twat squeezes. And, she could feel each muscular pulse of my cock. Diana purred a happy little sound. A piece of me was now a part of her. I had a secret desire to say, "I love you". But I knew such a declaration was both silly and very premature; it was more a desire to express gratitude for the pleasure given, than as a declaration of our emotional connection. Wisely, I remained silent, and savored the moment.

My body scent was all over her and in her. She smelled more like me, than I do. I'd marked her with my pheromones. She was now mine now to do with whatever I wished. I owned her and she must've had a similar feeling. Because she was always this submissive whenever we fucked thereafter.

I dismounted as gracefully as possible, given her undignified ass-in-the-air position. She casually turned around to sit on the ottoman. Her pussy made an embarrassing sound as my cum gushed out. We both laughed at her queef. I was still fully hard as I stood before her. Without hesitation she leaned forward and took me into her mouth and sucked me clean. Something else that became her habit every time I fucked her. I was surprised by this act. You have no idea how much this pleased me. So, I withdrew and kissed her. We share the taste of our sex.

She turned out to be a pure submissive in bed. In the many times we fucked, it always ended with me either pounding her doggie style or her on her knees sucking me off. That is how she wanted it. Fine with me.

We became regular fuck buddies for the rest of the time I worked at the same firm with her, for well over a year. We fucked at least twice a week. Sometimes I would come to her home before work, we would fuck, shower and then go to work in separate cars. Sometimes we would leave for lunch separately and go to her home and have a nooner. Sometimes we would meet for drinks after work and go to her place to fuck afterward, just like we did the very first time.

And, as often as we fucked, she never once asked for some kind of exclusive arrangement, nor once came to my home, nor even questioned me about who else I might be fucking. Diana was an unusual woman... my demanding boss at work and my very willing sub as soon as I had her behind closed doors.

verbiage55
verbiage55
45 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymous10 months ago

Great story, loved it, how they both get out of it what they need...

AnonymousAnonymous10 months ago

I don't know how anyone could let that go....5 Stars!

mathur_nkmathur_nk10 months ago
A pure f*** story

A pure f*** story between a sub woman and dominant male. Some scenes of office where she reminds him who is the boss. Some sex in her office chamber where she refuse to be sub and be dominant boss also can be there with instruction to obey the boss in office both for sexual and non sexual act.

Share this Story

Similar Stories

Her Son's Best Friend A newly divorced MILF finds a young lover.in Mature
Did I Make the Right Choice? What do I have to do if I am more attracted to her mother?in Mature
Every Schoolboy's Dream Sex with MILF teacher + dating her hot cheerleader daughter.in Mature
Mama's Beach House A man and his best friend's mother become lovers.in Mature
MILF Motivation Victoria fucks her slacking student.in Interracial Love
More Stories