This all started following a submission from a very good gurl who’s a follower of mine:
>I found myself daydreaming the other day. I found a cute little pencil skirt and put it on and I thought how good it would look if I put it on, with my tall black heels and a silky white blouse and visited your office for a ‘meeting’. I thought about being on my knees in this tight little skirt, working my lips up your hard cock all nice and slow. Ruining my lipstick on your hard, glistening cock. Then I found myself wondering what you would do to my little, tight sissy boipussy now that I had gotten your cock all hard…
As your mouth and hands devoured my cock with me leaning back onto the desk… I’d wrap my hand up in your hair, controlling every up and down, forcing your mouth to take more and more of my hard cock into it. I’d lean back and press the intercom button, telling my young, shy assistant to come inside. And there you’d be, on your knees, stroking my cock in your hand, looking back at her wondering what I had planned next. I’d tell her to close the door and come a little closer.
As she approached, I’d look down into your eyes and tell you to stand up. And as she came closer – her chest rising and falling with anticipation – I’d tell her to take over what you were doing as I told you to undress me. You’d start loosening my tie and thinking about it wrapped around your neck, you’d unbutton my shirt, feeling my muscles flex and relax with the pleasure from her mouth, and I’d lift my arms as you removed my undershirt, exposing my hairy chest and tattoos, completely hidden in my suit. I’d pull you close and kiss you hard and long, groping your ass and tits like a piece of meat. I’d rip open your shirt, knowing you’d have to leave later on clenching it together with everyone knowing exactly what you had been doing. And when your tits were exposed to me, I’d squeeze them softly – at first – playing with your nipples. Giving them little licks and sucking on them to see just how sensitive they were.
I’d look down at my secretary and tell her to finish undressing me. She’d remove my belt and pants, pulling my boxer briefs over my completely erect cock, running her hand down its shaft and lightly squeezing my balls hanging at the bottom. As she did that, I’d tell you to hike up that pencil skirt and take off the little thong you’d been wearing. And as she saw your little clitty for the first time, I’d walk around to my leather chair and take a seat, leaning back into its smooth surface and motioning for you both to come to me. I’d tell you to get on your knees and worship my cock more and as you did that, I’d tell her to massage your floppy little clit and start eating your boipussy until I was satisfied. And there I’d watch, your head moving up and down, rubbing my cock all over your face, messing up whatever makeup was left, my precum smeared all over… with her face buried between your cheeks and a hand lifted up, rubbing your limp clit.
After a few minutes of watching and listening to you sucking my cock for all it was worth while your boipussy was readied for me, I’d tell her to remove her panties as well and lie down on my couch. The same couch where I wrapped a tie around your neck and fucked you into a sissy coma… I’d order you to get onto your knees in front and start licking her pussy, up and down until she couldn’t keep the moans quiet. Then I’d take a knee right behind you, and slowly, with my hand pressed against the back of your neck pushing you into her twat, I’d slip my cock into that tight, filthy, soaking wet hole and as you lifted your head to moan I’d silence you by pushing you right back into her. I’d start slowly, moving up and down bringing the entire shaft almost out of your ass and then pushing it right back in, slowly and steadily building up the pleasure for both of us. And when I didn’t feel like doing the work anymore, I’d stand back up and get on the couch, pushing my cock into that secretary’s mouth, using her face to clean up everything I’d been picking up from your ass. I’d hold onto her head until she kept tapping my leg to catch her breath and then I’d let her go, telling her to sit in a chair in front of my desk and watch.
Then I’d sit back onto the couch and get comfortable while I motioned for you to get on top of me. “Show her exactly how a filthy sissy pleases master’s cock…” Then we’d watch. Me from behind, moving my hands from your waist where I felt every move and twist, to your tits where I squeezed and relished the little titties you had grown for me, then up to your neck, wrapping my fingers around it and pulling you down, hard, onto my cock just so every inch of me was now in your gaping hole. I’d feel it as you ground down like you needed what would come out… your face would start to turn red and you’d slow just a bit because of lightheadedness, and then I’d let go. You’d gasp for air then double down on your mission to milk my cock with that tight little pussy.
“It’s your turn” I’d say to you as I lifted you off of my cock with ease and tossed you onto the couch. “Legs up” is all I would say and then motion for her to join us again. As she came close, I’d tell her to get down on all fours and get to work. And then I’d watch as her eager to please little body rushed forward and started licking your taint, your asshole flush with all manner of juices, and your little bitty clitty, still limp and lifeless. Then I’d kneel behind her, and using a finger at first to test her eagerness, I’d slide it into her asshole. And listening to her desperate, eager gasps, I’d slide in another finger and another until I knew she could take me. With her there, feasting on your boipussy and me right behind her, looking into your eyes with an intensity that scared you, I’d slip my cock into her virgin asshole and begin pumping. Little cries would escape her lips but she knew exactly what to do and would bury her head into your ass and taint, licking long strokes up and down as she fought to concentrate on her job. Then I’d motion with my finger for you to lean forward, me grabbing the back of your neck, pulling your forehead to mine with me still staring into your sissy boi soul. And then I’d kiss you as I started to pound harder and harder the little ass in front of me. Just before my cock swelled and exploded, I’d stand and push it into your mouth, your hands wrapping around its shaft and your lips sucking, sucking every last drop of my sweet cum out and savoring every drop.
I’d grunt loudly and push your head down onto it again with that animalistic urge to just FUCK something in that moment, and then I’d turn around and lie back onto the couch. My little secretary still lying there, heaving and recovering on the floor. But you’d be right there between my legs, eagerly cleaning off every inch of my shaft, my balls, all of me. And as you finished up, I’d look you in the eyes one more time and tell you what you’d come there to hear, “Good gurl…”
Source: reddit.com/r/eroticliterature/comments/eyac2x/afternoon_delight_in_his_office_m_tf_f_anal_rough