This happened a few years ago. For my girl’s birthday, I asked her if she wanted to experiment with any new roleplay scenarios in the bedroom. We discussed some ideas, and she mentioned the idea of me being her boss and putting her in a compromising position.
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At this point, Rachel was working as a personal secretary for this guy who she regularly blasted as a huge asshole. Her responsibilities in the office also overlapped with menial personal duties (Fetching coffee, dry cleaning, etc.), and he could be rude. Rachel had told me he once had made mocking, innuendo-laced comments in a front of a client about her (“She has to do whatever I tell her”).
The night of her birthday, we had a lovely dinner and then briefly parted ways to change into our roles. I wore a buttoned shirt and suit in the style I’d seen her boss, Tony, wear (Though Tony’s wardrobe definitely cost more than mine. We’d met before and you could see the smugness in how he dressed).
Rachel knocked on the door and entered. She wore the kind of outfit she’d usually wear to the office — a white button down blouse, a black skirt, stockings. The problem with Rachel is that she managed to look sexy in everything — she’s slim and athletic, but her ass always draws too much attention. I was already getting hard at the thought of what I was about to do to her.
I told her to take a seat and ignored her while I worked on my computer. Finally I asked her if she knew why I called her in.
“No,” she said innocently. “No idea at all.”
I told her that there have been complaints about her wardrobe in office. That some found it inappropriate.
“What’s inappropriate about it?” She challenged.
I told her that multiple co workers had mentioned that they’d seen her underwear when she bent over. Rachel blushed — she’s had a recurring fantasy about that exact scenario happening.
Rachel lightly protested, saying that it wasn’t her fault her co-workers were looking at her. I shushed her, stood up and towered over her. My hand brushed the back of her head. I could see the hint of her black bra underneath her unbuttoned blouse, and I couldn’t help but imagine her actual boss getting a glimpse of her cleavage while he hovered over her desk. The thought gave me knots in my stomach.
“We can fix this right now, if you can be a good girl,” I told her. I slipped my hand into her shirt to cup her breast.
“You think another firm would hire you? You’d be out on the street.” Rachel gasped as I roughly grasped her tit. “You’d never find another job without me.”
“What do you want me to do?” She whimpered.
“Give me a kiss.” I told her. I directed Rachel’s head to my crotch. She reached for my trouser zipper and I swatted her hand away.
“I didn’t ask for that,” I told her. “Give me a kiss.”
“Yes sir,” she gasped, and Rachel began to kiss my erect cock through my woolen suit pants. She was gentle, sweet and demure.
“Good girl,” I told her, stroking her hair. I decided to go for it: “See? You do EXACTLY what I tell you.”
Hearing Tony’s words back to her made her go feral. She begged me to let her suck my dick, and I let her. She kneeled in front of me, in the same outfit she wore so many times around her office, and swallowed my cock while I settled into my desk chair. I yanked up her skirt to expose her ass.
“You should go into work like this more often,” I managed to say as she sucked the life out me. “It’d be good for workplace morale.”
“I’d love to,” she said back. She humped my loafers desperately while continued to blow me, and I couldn’t help but be struck by how badly she craved this, how this deranged fantasy of being used by her boss took over her body and turned her into a wild, dripping bitch in heat.
I took Rachel on the desk next, pounding her from behind while lightly pulling her hair. As I plunged my fat shaft inside her, I could feel her body quake. I decided to break character, because I knew it’d be the perfect push to get her to cum.
Gripping her ass hard, I said: “Say his name for me, baby. I know you want to.” She grunted in pleasure and shock. “Its OK. He’s your daddy. He keeps you late. You do whatever he tells you-“
“Fuck.”
“You know he talks about your ass to clients, right? They all watch you as you leave the room.” I kissed her hungrily and said:
“Who’s your daddy, baby?”
“Tony’s my daddy.”
I spanked her. Hard. Commanded her to say it again.
“Tony’s my daddy!” She screamed. I couldn’t stop myself. Tony spent more time with my wife than I did. He kept her late at the office, worked her like a dog, and had the gall to be an asshole to her. But here she was, on her birthday, fantasizing about him having his way with her. I could feel Rachel’s body quiver from an orgasm and I did the same: I finished hard, flooding her warm pussy as I cried out alongside her.
I collapsed on top of her, our best clothes absolutely ruined and rank with sweat and cum and bodily fluids, and I felt a flood of dirty shame for pushing this fantasy this far. But at the same time, I was on fire — turned on by how hot and bothered Rachel was for this rich piece of shit, especially since she’d have to go in the office the very next day to see him…and cater to his every command.
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