I stared down at my naked secretary, barely able to hold back. She reached down to her wet pussy and began playing with herself... And then reached out again with the same hand and grabbed my dick. She didn't know it, but if she'd pulled me in right then, I wouldn't have been able to stop her.
Instead, she started giving me a very wet handjob, covering my dick with her juices. Every few seconds she'd reach back down, dipping back into her pussy, and then covering me with even more of her wetness. Her soft, now-sopping hand felt almost — almost — like we were actually fucking. Slowly, she pulled me closer and closer, leaving the gap between my dick and her pussy smaller and smaller; as I thrust, occasionally I'd feel them rub briefly against each other. She smiled, and mostly dispensed with the pretense of using her hand to slick down my dick, pressing me up against her pussy lips directly and rubbing the head against them, using her hand to slowly work the juice down from the tip. Wrapping her legs around me, she pulled me closer, running my shaft up and down against her pussy, covering it in her wetness but not actually fucking. On each downstroke, she'd subtly but perceptibly press the tip slightly more, until I was ever so slightly inside her. But then, grinning, she'd take me out and continue sliding me back up against her.
I was in agony. Her enormous tits jiggled with every stroke. I could barely hold myself back.
Eventually, on one of the downstrokes where I was just barely embedded inside her, she looked me in the eye and held my dick in place for a moment, slowly jacking me off. "You have to tell me before you cum," she said. I nodded, and she returned to sliding me back and forth against her. She was getting wetter and wetter and beginning to pant; this was clearly getting her off, too.
A few minutes later, on yet another downstroke that ended with my tip slightly inside her, I knew I couldn't last any longer. I told her so. She grinned, and held me in place, just barely inside her.
"Rosie, I mean it, I can't hold back anymore," I told her, hoping she'd understand the position we were in.
"Oh?" she said, teasingly, grinning wider. "Having your dick inside your slutty secretary makes you want to cum?" I felt her legs wrap around me.
I couldn't help it. I thrust slightly, and my head fully entered her.
"Cum inside me, then," she said, with her Cheshire cat smile. She knew she had won, and with unyielding force her legs pushed me deeper, deeper, deeper inside her, fully up to the hilt as I came. I pulled back and then thrust back into her repeatedly, still cumming, in one of the longest orgasms of my life. As she felt me paint her insides white as we fucked, she came too, writhing against me and moaning, nearly shrieking, uncontrollably.
We lay there for a long time. Eventually, slowly softening, I pulled out of her. We dressed quietly. Before she left, she pulled me against her and aggressively kissed me, pushing her tongue into my mouth. I groped her soft, giant ass and felt her massive tits as she pushed her mouth against me.
I knew I had gone too far; I knew she had me trapped now. I might as well enjoy what I could.
"See you again tomorrow," she said, and turned to leave. I stared at her fat ass she walked away.
^^^^^^^
I racked my brain for a way out, but I was in too deep. The next day at lunch, Rosie stopped by my office, locking the door behind herself with a smile. Her clothes were off seconds later, and this time was different. Unprompted, I took mine off too, and walked over to her, pushing her down to the floor.
"Fuck yeah, Matt," she whispered breathily, grabbing my dick. "Take what you want."
I pushed her thick lips over my cock, taking control. She felt amazing, as always, and as I slid in and out of her wet mouth she looked up reverently; our relationship had changed, and she knew it. No longer was she Rosie, the slightly sad and desperate older divorcee; no, now she was Rosie, the boss's hot dirty slut, his dark secret, his...
...She took her lips of my cock and slowly pulled herself on top of me like a spider about to devour its prey. She kissed me deeply, and I kissed her back, our tongues twisting around each other as she slid my unprotected dick into her bare pussy. She was soaking. She swiveled around on my dick, one jiggling leg briefly going over my head in an impressive display of agility for someone of her species, doing a 180 and facing away from me as we fucked, giving me a view of her striped ass bouncing.
"Fuck me Matt," she moaned. "Fucking use me, own this pussy."
"God you're so fucking good," I moaned back.
"When you first became my boss, did you ever think we'd end up like this? Your dick wrecking this pussy in your office?"
"No," I said, truthfully.
"Me neither," she moaned, "I never knew you'd be so into me... I couldn't have believed I'd catch you jerking off to me late at night. And I guess it's pretty lucky for you that I was single, huh? That I was into you, right? That I could talk you through your fears? So you could finally take this pussy just... how... you... wanted..." she shook, cumming, as she slammed down on top of me. Her distorted narrative was, perversely, turning me on, and I was close to the edge too. But I held myself back, and wrapped my arms around her flat stomach and played with her clit as she covered her mouth with her hands desperately to muffle her screaming orgasm. I moved my hands to her soft tits and pinched and rolled her long nipples, kissing her neck.
"God you're fucking hot," I whispered.
"You make me feel so fucking sexy baby," she moaned. Baby? Uh-oh. But before I could process the term of endearment, she kept going. "Have you noticed I've started wearing less for you?"
"Yeah," I said, "I fucking love it." In the moment, it was true.
"I'll keep dressing like a slut for you baby. I'll wear skimpy little dresses and high heels. I'll wear lipstick every day and smear it all over your dick every morning. Would you like that?"
"Oh god yeah Rosie," I said. "But if you do that I might not be able to hold myself back from taking more..."
"Oh yeah?" she said, peering innocently back over her shoulder. "You're gonna have to fuck me every day at lunch?"
"Yes."
"And maybe after work, too? With some wine?" she continued.
"You're gonna drain me, Rosie. You're going to completely drain me dry."
She swiveled around slowly on my dick again. I was barely holding it in as she dragged her body up and down against mine, and she looked me in the eye.
"I want all your cum baby," she said, staring at me. "I want it fucking all." As she said it she grazed her tits against my chest slowly, and I could feel the point of no return.
"Well here it comes, Rosie," I moaned.
"Cum inside me baby," she whispered darkly, and I did.
That night, sure as clockwork, she showed up at my desk again with wine, and I fucked her again. "Come early tomorrow," she said as she left, and I did; sure enough, her lipstick was smeared all over my dick as promised before 9am.
We fucked again, and again, and again, and again; she quickly became more and more affectionate, and in our nighttime sessions we spent longer and longer kissing and cuddling.
She started wearing lingerie under her clothes, and by the end of the week she pretty much only wore lingerie (or nothing) any time she was in my office for any reason.
She turned up the heat quickly, getting more daring, sometimes just sitting under my desk touching herself and sucking me off as I worked throughout the day.
My wife, Melissa, was barely interested in sex recently, but even if she had been I'm not sure I would've had enough in me for it.
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