If you haven’t read Blackmailed By Her Boss 1, 2 and 3, catch up here:
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Right on time, Carrie knocked on my door, even though it was 8 p.m. and everyone else in the office had long since left for the night.
She was such a good, obedient girl! And all mine. Although tonight - though she didn’t know it yet - I was willing to share her.
With a sly smile, I nodded at the two other men in the room. This party was about to get started!
Lascivious grins split their faces as they looked forward to my secretary’s big entrance. I’d told them both a lot about her and had shared some of the videos I’d recorded of our more ‘elaborate’ sessions together. I’d kept Carrie to myself for a lot longer than my usual girls and they were both impatient to sample her many delights for themselves.
In the office with me were Dale Conway and Ralph Murphy. Dale and I went way, way back. We were in the same frat and had been on countless debauched adventures together since then, our tastes being almost exactly the same. Dale sent some girls my way, I sent some to him and - on nights like tonight - we occasionally enjoyed them together. He was in his mid-fifties, with a prudish wife at home, just like me.
Ralph was a piece of work. He and I were members of the same country club. He was a few years older than me, a real pillar-of-the-community type. He’d become aware of my proclivities after catching me fucking a waitress at the club. Sweet girl, even sweeter after I’d tied her up and fucked and spanked her whilst she begged for more. She’d gotten a little too carried away and screamed loud enough that Ralph had found us in one of the cabanas together after dark.
He’d walked in and seen us, taking a couple of fast shots on his phone whilst I disentangled myself from her. He’d then asked for a turn on her himself.
Luckily, the girl had a pretty solid older man fetish and he’d caught us right on the brink of her orgasm, so she’d agreed willingly.
After shooting his load in her, he’d scooped his slime up from her pussy and, with it still glistening in his palm, firmly shook me by the hand. Over the noise of his cum squelching around in the grip of our handshake, Ralph had said, “Let’s do this again soon, eh Jack?”
Clapping me around the back, still pumping my hand in his, his cum oozing out between our fingers, he’d followed it with, “Let’s keep this nice. A shared hobby binds two men together in an inviolable bond, I always say.”
Finally releasing me, he got the waitress to lick his hand clean, before strolling off, whistling happily.
The irony wasn’t lost on me: I’d blackmailed a dozen secretaries in my time and now Ralph had put the squeeze on me. Karma was a little bitch and so was he, I thought, shaking my head ironically.
Since then, I included him in something every few months. He’d been over to my office a couple of weeks ago and we’d watched some Carrie footage together - there was no way I trusted that bastard enough to send it to him - and he’d said he wanted a turn on her.
I’d been meaning to share Carrie with Dale for a while by then, so I’d set up this little soiree for the four of us. Only Carrie was unaware of my plans for the night, but she would be easily persuaded, I knew.
Right on cue, there was another timid knock at the door and I shook myself out of my brief reminiscences, calling out my permission for Carrie to enter my office.
She walked in and three pairs of jaws dropped simultaneously. It was Halloween tomorrow and I’d told Carrie to dress up as a sexy schoolgirl for tonight’s event.
As ever, she had totally dedicated herself to the task at hand. Her soft brown hair was tied in two long pigtails, one on either side of her head, with little bows tied around each.
Her beautiful face was seductively made up. Thick layers of mascara around her eyes, her pouty lips shiny and coated with red lipstick. She knew I loved to watch her make-up smear all over her face as I deep-throated her with my fat cock until tears ran down her cheeks, leaving crimson rings of lipstick all over my thick meat as she worked it in her mouth.
She wore a blouse that was mostly unbuttoned, exposing a black lacy push-up bra from which her plump, juicy tits were already bursting out.
The blouse was knotted at her midriff, exposing her taut, tanned stomach. Below that, a tiny mini skirt, short enough that her black garter belt and the lace tops of her stockings were clearly visible. Ludicrously high heels graced her pretty little feet, laces tied so that they’d stay on as I made use of her in every corner of my office.
She was fucking perfect. And confused.
She looked from me to my two companions and then back to me.
“I’m so sorry, Sir. Should I come back later?”
“No, Carrie. You’re exactly on time. As usual. Good girl.”
“But…”
“It’s almost Halloween, Carrie. So we’re going to play a little game of Trick Or Treat. This was your first trick of the evening. It won’t just be me that’s making use of you tonight.”
“But Sir!” she started looking around the room frantically, reminding me of the night when I’d first persuaded her that becoming my office whore was her wisest option. My cock throbbed at the memory. I loved that she’d become my willing little fuckdoll over the months, but I couldn’t deny the thrill that I got from seeing fear in her eyes for the first time in a long time. Tonight was going to be fucking fantastic!
“Carrie. Our agreement has always been that you are mine to use, whenever and wherever and with whomever I choose. Remember?” There was a steely edge to my voice as I spoke. A little resistance from her was fun, but Carrie needed to know her fucking place.
Blinking slowly, she said, “Yes, Sir,” her voice shaking and her body starting to tremble. Fuck! This was just like the first time that I’d taken her. My cock still pulsing impatiently, rock-hard in my pants, I pointed to Dale and Ralph.
“These are my very good friends, Mr Conway and Mr Murphy. They will let you know how they prefer you to address them when the time comes.”
Dale and Ralph grinned lecherously at my sexy little secretary. Dale, cocky bastard that he is, even gave her a little wave. His friendly gesture was somewhat undermined by the imposing length of his monster cock, the outline clearly visible in his pants, even seated.
Carrie nodded nervously in acknowledgement, her lip wobbling in the way that I so adored.
“Now, Carrie. Since we started this appointment with a trick, Mr Conway here is going to give you a treat. Make sure you do exactly what he says. Do you understand?”
She nodded again, a sudden manic energy in her movements. The poor girl was still in shock, bless her heart! Still, we had no time to waste…
“Have at her, Dale,” I said, with a wink, getting up from my desk and moving across to the nearest couch, taking the best spot to enjoy the show that was about to start. Carrie looked at me forlornly as I crossed the room.
Dale stood up and walked over to her, towering over her, even in her 5-inch heels. He stroked the side of her quivering cheek, smiling slightly as she flinched nervously at his touch.
“Let’s have you over on the desk, shall we?”
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