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Chapter 39
by
caitlynmasked
Does Joy get help from Mr. Colton?
Mr. Colton helps get Joy off
I find myself clenching my jaw in frustration as Mr. Savidge stands up, takes my hand in his, brings it to his lips for a quick kiss, then departs the office. On the one hand, I have reason to celebrate. I have the job! Starting tomorrow I can find out how to get back into the secured area and then start my research. On the other hand, I have to further debase myself starting now. Not only am I going to have to act like and appear to be just like any of the other sex starved women here, I was going to have to do it in a way that satisfied a man who wanted me fired.
Sex at home from a robot. Sex at home from my neighbor. And now sex at work from my boss. At this point, it’s easy to see how women would be seduced into a life accepting this.
Heading out of the office, I return to the front desk and look for Mr. Colton. Not seeing him, I ask one of the men working there where he is and follow their directions into one of the many library sections. The smell is satisfyingly familiar. Old books, leather, dust. It smells like knowledge and propriety. It smells like everything is right in the world, even when I know it’s not. I must have gotten lost in my own thoughts as I hear Mr. Colton’s surprised “Oops!” a bare moment before I walk right into his chest.
I’m sure I would have broken my nose if my breasts hadn’t taken the brunt of the collision. But I’m still tripped off balance and have to throw my arms around Mr. Colton to avoid falling flat on my face. I feel his arms around my back, holding me steady but also holding me close to him. When I look up toward his face, I see him smiling down at me. He sounds honestly amused at our bumping into each other, “Miss Williams! My my my, you’ll have to be careful in the future. While there aren’t many clients here at any give moment, you still need to keep your eyes open!”
He rests his hand on my head and pulls me closer for a hug before taking a step back and letting me go. “I assume you were looking for me. How did it go? Are you our newest employee?”
I nod absentmindedly, knowing that I have to get him to have sex with me. “Yes. Mr. Savidge said I was to be your assistant, so I guess I’ll be doing whatever you want me to do. Plus, I’m to seek you out specifically for any… um… you know…” I find it hard to continue to look at him with what I have to ask for.
Montana’s hand cups under my chin and forces me to look back up into his face. His smile is genuine and warm. “You’re to seek me out for any of your sexual needs. Don’t worry Miss Williams, I’m accustomed to dealing with Mr. Savidge. While he’s not my direct supervisor, we work together often and he’s an old-fashioned man. I’m sure he’d like nothing more than to send you home to get naked and pregnant. I, on the other hand, love that you’re intellectually curious and seeking out an important job and will support you however you need. I’ll not only consider it my duty to keep you personally satisfied but will consider it a pleasure of my own. I can see that you’re nervous after the interview, so… are you ready to go now?”
I feel myself trembling a little as this man, both attractive and intellectual, stands before me offering sex that I know will be mind blowingly pleasurable and frustratingly mentally feminizing. But this is for me. This is for my society. This is for my future. Nodding I put my hands on his waist, move up onto my toes, and give Mr. Colton a kiss with a whispered “Yes, I’m ready.”
I don’t even try to stop the moan that escapes from my lips to his as he reaches down and cups my ass, grinding our bodies together and letting me feel the bulge in his pants. When he pulls away from the kiss, he smiles at me in a rather nerdy way and says softly “I have just the means to guarantee your pleasure. As we work together more and more, I’ll focus this to your specific desires and needs, but this method works as it hits the pleasure points of almost every woman. We'll start with oral.”
I feel a pang of anticipated pleasure rise up from between my legs as I remember Bradley and his magical tongue’s action on me, but my mind is quickly refocused as Mr. Colton gently places his hands on my shoulders and pushes me down to my knees. Oh… Oral.
I steady my hands before reaching up and undoing Mr. Colton’s belt and unzipping his pants. With what’s becoming a practiced hand, I pull his pants and underwear down, pulling back at the last moment to prevent his already hard cock from slapping me in the face as it springs free. His voice sounds calm and clinical as he pets my hair and says “Go ahead, show me what you got. I’ll guide you though if I need to.”
Grabbing the base of Montana’s cock, I take just a moment to remember Sterling’s lessons. As I start to lick along the length of the cock in front of me, I realize I’m finding more and more ways of differentiating different men’s manhoods. There’s of course skin coloration, but it also moves into size and veinyness. While Mr. Colton’s skin is generally pale, his cock is darker toned. He’s larger than average…. although I might have to adjust my idea of average as I’ve seen few men here below average size… in both length and girth but smaller than my current men’s cocks. His veins stand out quite a bit, giving his length more textural differences than Sterling’s rather smoothness, or Bradley’s normative geography. And then there’s taste. Sterling of course has a subtle plastic taste that’s easy to identify. But Bradley has a more musky, more manly flavor than Montana. Or is that just mental? Am I associating Montana’s flavor as less manly because he works in a library where Bradley works in construction?
All of this goes through my head as I lick and kiss my way along his length. Once I’m satisfied that he’s moistened enough I move right into the main show and take him into my mouth. I don’t try to hide the frustrated groan that wants to spill out and in fact emphasize it, knowing that it comes across as a pleasured moan to the one I’m currently sucking. I can feel Montana’s hand work through my hair as I start to bob up and down, working my hand in synchronicity to my head’s movements and stimulating his entire length. As I bring my other hand up to his low hanging balls and cup them, I feel his hand gather up my hair into a makeshift ponytail and use it to start guiding me. Sterling taught me to submit to my man when he shows me his desires, and even though Sterling let me be in command of this activity, I follow his advice and let Montana become my puppeteer.
Montana’s first guided motion is to pull me down close to him, feeding almost his entire length into my mouth. My eyes flash wide as I wasn’t ready to take him into my throat. Like with Sterling’s intimate lessons, my hands quickly reach up to Montana’s knees as I barely control my gag and try to pull back. But where Sterling let me relent, Montana’s grip pushes me harder, sliding not only the head of his cock into my throat, but an additional inch or more. I feel Eileen give me my pleasurable reward for doing this well and even feel her activate my plug to vibrate pleasingly, but it doesn’t stop my gorge from beginning to rise. Montana lets me pull back just a bit before pushing into my throat again. Another buzz, another pleasured Eileen response, another gag. Montana keeps up this action of sliding in and out of my throat for several minutes as tears stream down my face from the strain and I use all my hours of practice to simply keep from losing my mind throughout the **** of my throat.
When Montana finally pulls me completely off of his cock, he tilts my head back so that I’m staring up at him. I take a deep shuddering breath, feeling a great need to re-oxygenate myself as he smiles down at me and says “I can see that you need to practice your throat more. Tell your AI assistant to make a training regimen for you.”
I don’t have time to tell Mr. Colton that I’m already going through daily instructions on deep throating techniques as he uses my hair to guide me up into a standing position. It’s a strange dichotomy as Mr. Colton, while certainly attractive, comes across as an intellectual, but is treating me more brutishly and mechanically than either Bradley or Sterling ever has. With ease, he turns me around and hugs me close to him, letting me feel his hardness rest on my ass while he cups and teases my breasts. He kisses at my neck for several moments before reaching down and rolling my tight pencil skirt up to my waist. Once my panties are on public display, he turns us together and bends me over one of the library’s tables.
He wastes no time in pulling my panties down before pushing my legs further apart. I hear his amused voice say “Oh, I like this!” as he pulls my plug quickly and smoothly from my ass. I can’t stop the grunt as I feel my sphincter unexpectedly opened wide and again can’t help but compare him to Bradley and Sterling, both of whom have removed my plug but have done so gently, making it a fun and ,dare I say, pleasurable experience all on it’s own. Montana, on the other hand, simply removes my plug like you’d remove a cork from a wine bottle.
My grunt is repeated as he pushes his already moistened cock into my ass. I still can’t get my head around women here finding this pleasurable. When combined with other pleasures it’s not horrible, and certainly I’ve grown accustomed to the plug and its affirming vibrations, but Montana’s length and girth fill me up uncomfortably until he’s pressed up against my ass, pressing me against the table. Reaching forward he grips my neck and **** me down until my cheek is against the table. Once he’s satisfied I’ll stay where he put me, he moves his hands to my waist, holds me still, and starts to slowly but methodically fuck me.
I probably could have gotten through the activity all on my own, but Eileen was there doing her best to ‘help’ and give me pleasure throughout. With her internally stimulating me, Montana holding me, and his cock sliding in and out of me, I’m quickly panting and on the edge of an orgasm. Close enough that I let out a whimpering disappointed sound when he pulls out of me entirely. With a surprising amount of strength, Mr. Colton rolls me over, guiding my leg around him, until I’m lying on my back with my legs on either side of him.
While I feel myself flushed with involuntary pleasure, his face clearly shows he’s enjoying himself and yet he’s also clearly just working. Performing a task. Gripping my ankles, he guides them up to his shoulders before roughly wiping his manhood clean and shoving it unceremoniously into my pussy. Thankfully I was already dripping wet, making the transition smooth and easy. My hands fly to cover my mouth as the stimulation is overpowering and I find myself moaning and mewling in pleasure. As with my ass, he slowly and methodically fucks me. This corner of the library is filled with the fleshy sound of him bumping repeatedly into my ass as he bottoms out in me and my muffled appreciative moans. It doesn’t take long, since he clearly knows what he’s doing, before my pleasure shoots up like a rocket and explodes. Looking up at the gilded ceiling of a library I orgasm loudly, fully, and overwhelmingly.
I barely have time to register that he’s successfully gotten me off this quickly before he’s started back up with his thrusting. Slap, slap, slap, the sounds fill the room again as my orgasm rebounds and starts rising again. My eyes roll back into my head as I let my hands fall to my sides and simply accept that I’m going to cum again. This time, loudly.
And then again.
When all is said and done, my new boss Mr. Colton was able to give me three orgasms in the span of just twenty minutes. He guides me to a bathroom where I’m allowed to clean myself up and re-apply my makeup. I make a mental note to bring at least a couple fresh pair of panties with me, as well as some cleaning wipes when I come to work in the morning. With my legs still shaking, I walk out and see that he’s already working and organizing a large stack of ancient books. He smiles at me, pulls me in for a soft kiss to my cheek and asks if I need a ride home. He chuckles when I say I’ll call for a ride, letting me know that women can’t call for their own ride from downtown.
A quick phone call later and he walks me outside to a hired ride that will take me home. The driver and Montan speak for a moment before he moves to the backseat window and leans in to speak with me. “I look forward to working closely with you Joy. I hope you don’t mind, but I’ll start calling you Joy when we’re alone. I’ll stay with Miss Williams when there’s others around to let them know you’re here on a professional basis. So long as you come in with a cool head, I should be able to keep you satisfied. It’ll honestly be my pleasure to do that with you a couple times a day.”
I take a deep breath in, wondering if I’ll be able to mentally process all of this. It might be a minimal amount for a woman of this time, but that’s a lot of sex for me to take on a daily basis and isn’t even counting what might happen during the evenings. My brow furrows a bit as he taps at the door and adds “And each night I’ll send you home in a specialty ride like this. The driver is ready to help you out, has toys and sounds and other methods to make sure you have a fun time on your way home. Enjoy!”
Before I can ask what he means, the window rolls up and the driver pulls away from the library. Looking into the mirror at me he smiles knowingly and says, “Just relax ma’am, and enjoy!”
Soon thereafter I feel the seat below me start to vibrate pleasantly while the center armrest flips down, displaying a collection of dildos and vibrators.
How does Joy's ride and evening go?
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It's a Man's World
But it wouldn't be nothing without a woman
Jim and his two scientific partners research time travel and discover a disaster coming in several years. Unable to learn more about it, they have to travel far into the future and hope they can learn from the 'history' about the disaster in order to return and prevent it. But the world they find is very very different from our own. It's a Man's World!
Updated on Jul 3, 2024
by caitlynmasked
Created on Feb 25, 2024
by caitlynmasked
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