Caresse's Awakening Ch-01

“Uh….er, will you use any lube? What about my apartment? I just got finished this month’s rent. I’m on a month-to-month lease. What about protection? I don’t want to catch anything or get pregnant. What happens if it doesn’t work out between us? I had a hard time find this apartment and this job. I don’t know how I can deal with getting fired and being out on the street.” She asks uneasily.

“Yes, I’ll use lube. How much depends on whether or not you’re being punished. As far as this month’s lease is concerned, you’ll stay at my place, and that give you time to pack your stuff and prepare for the move. I’ll pay for the movers. As far as protection is concerned, you’ll go on the pill, until I decide otherwise. I’ve already been tested for STDs, and I can show you the doctor’s report. You, having been a virgin, obviously don’t have any STDs. Just for protection, you’ll get a full check-up next week. I’ll set you up for it, including full blood work. That will cover all health issues. The company’s health insurance covers that. If things don’t work out between us, I’ll help you find a place and I’ll give you good references for another job. I’ll possibly point you to some people that may hire you. From time to time, I will command you to service other people, but in those situations, they will be using condoms. I will also use condoms myself when having sex with other people. Now, I believe that I told you to get undressed! That will earn you 10 more swats! Strip now!” He asserts.

“Yes, Master! I’m sorry!” She acts contrite, then disrobes, stepping out of her panties. She takes off her blouse first, and follows this with her skirt. She picks them up and folds them neatly, laying them on one of the armless chairs in front of his desk. She awaits his next decree. 

As Romain sits in the other armless chair in front of his desk, he directs her to bend over his lap, and then positions her where he can spank her. Her feet and legs are spread, and her hands are gripping the legs of the chair. Her pussy is over his right thigh, giving him an excellent view of her “assets”. He begins swatting her hard, turning her pinkish ass red once again. He feels their combined juices dripping onto his leg. 

“You’re a very naughty girl, getting turned-on by spankings. I don’t think that you learned your lesson. Maybe I need to punish you even more.” He admonishes her.

He proceeds to swat her pussy several times, making her drip even more than previously. He reaches between her legs, and plays with her wet pussy. He inserts several fingers into her deflowered womanhood, stretching her further. After a few minutes of this manipulation, he succeeds in getting a moan out of Caresse. He swats her pussy several more times. This causes his cock to thicken, indicating that he is ready to take one of her other virgin holes. He is not yet sure which one. 

Romain pulls Caresse up into a standing position, telling her to stay put, while he walks over to his closet, and grabs a bottle of lube and one of the butt-plugs he keeps hidden there. He has a good-sized collection of sex toys and a variety of paddles for such occasions. This is not the first opportunity he has had to use them, being an experienced master. He has used these toys and paddles on several errant subordinates. Since he is the Chairman and CEO of the company, he doesn’t have to answer to anyone else. He does as he sees fit. All of the other employees that he has disciplined have agreed to it just like Caresse. 

He heads back over toward her with the chosen items, then directs her to resume her previous position over his lap. Spreading her cheeks as she complies, he applies a small amount of lube on her rectum, before inserting his index finger into it. He thus prepares her ass for the butt-plug that he plans to pop into her anal cherry. He begins adding more fingers, stretching her back door farther. 

When he hears her moaning in pain, he removes his fingers with a pop. He slightly lubricates the butt-plug, just enough to ease entry, but not enough to lessen the pain. This is a punishment, after all. He then shoves it in forcefully, making her yell out in burning pain. He slaps her ass on the butt-plug one last time, adding considerably to the torture she already felt in her tender asshole. 

He instructs her to get on her knees in front of him. He grabs her head, lowers it to his crotch, and shoves his cock down her throat. 

“Suck my cock, Slave. Clean all of your juices off of it! I want it extremely hard when I take your ass! You won’t be getting more lube than what’s in there and the spit you put on my cock. You had better polish it well! Don’t forget to lick my balls and ‘caress’ them gently with your hands.” He compels her, as he laughs at the pun he has made on her name. 

He shoves his extra large cock farther down her throat, past the gagging point, holding her head still. He thrusts his cock in and out of her throat, forcing her to deep-throat his cherry picker. He is not showing her any mercy. This is part of her training. He wants her to know what he expects of her. While his butt-plug is still readying her ass for his anal invader, he continues this ruthless face fucking for another ten minutes.

He then pulls her off of his cock, and leads her over to the over-sized, stuffed couch in his office. He puts her into a “doggie” position, with her ass in the air, and her face and shoulders laying on the sofa. He takes out the butt-plug, and it makes a loud popping sound as he withdrew it. Her ass continues to gape open, and he places his anal intruder where the butt-plug had just been. 

Taking her breath away when he first forcefully enters her, Romain starts plundering her ass. He will not able to last long, after the blowjob he just forced her to give him. 

“I can’t take this. It’s too big! Take it out! You’re going to rip me open! Oh, my God, please stop! No more!” She begs him. 

“You can take it, and you will! Your ass will get used to it! Once you get past the pain, you will feel the pleasure in it! Stop thinking about the pain, and start enjoying the pleasure of it! You only THINK that your ass is being ripped apart. You will be begging me for more of this soon. You’ll be taking this cock up your ass a lot from now on!” He says, giving her ass a smarting slap while he rides it hard. 

Caresse is stunned to actually find out that he is right. She IS feeling some pleasure in this callous act after all. The pain has subsided a lot, being replaced with the pleasure he mentioned. She starts begging him to fuck her harder, surprising herself even more. She can only imagine how he anticipated this change of her attitude toward anal sex. It would appear that he is an experienced Master, from both the way he acts, and the “supplies” he seems to have on hand. Not everybody keeps that stuff in their office closet. She can only imagine what he is going to do next. 

He speeds up as he takes her harder. He contemplates either cumming in her ass, or making her suck him off straight from her ass. He is not surprised to hear her moan in pleasure: they all do, in spite of their misgivings. She shows more potential as a slave than the other girls he has trained in the past. He is confident that he will keep this one around permanently. He has looked for the perfect slave for many years. He had almost given up hope until he hired her. She showed promise then, but he was unsure whether or not she would go for it. He has to be careful whom he chooses. 

Romain decides to go ahead and cum in Caresse’s bowels, especially as he is getting closer. He is ready to cum, and he doesn’t want to have to get back to that point again. He is prepared is to go now, and getting back there would take precious minutes he doesn’t want to give up. He thrusts a few more times, before he feels the cum churning in his balls, signaling its imminent release. He slams his cock in, all the way to his balls. He holds it there while he cums deep inside of her, filling her up with his jism. 

Caresse feels his cock swell even more, stretching her further than she was already. When he rams all the way into her, she is surprised to feel some of the pain come back. She feels him pause, and then she feels his load empty into her rectum. He does not appear to care whether she cums this time or not. It must be part of the punishment she is receiving and deserves. 

“I want you to clean my cock good now, so I can get dressed and order us some lunch. If I am to continue your training, I’m going to need some fuel, and so are you!” He commands her, as he pulls out of her ass. 

She turns around and complies, sucking all of their juices off of his cock. She feels his cum leaking from her gaping ass. She feels him forcing her head further down his cock, until his pubic hair presses against her nose. His mushroom head is in her throat, blocking her from breathing. All she can do is swallow his cock, cleaning everything off of it. After a few minutes, he slows down the rhythm into which he was forcing her, so he can allow his cock to soften. This allows her to breathe normally again. 

He needs a respite from all of the action, so he allows his cock to soften. His belly grows in protest at being empty. He has to get some food into his system, if he is to last long into the night, as he intends. He is not planning to let her get much rest tonight. It has been a long time since he has had a slave at his disposal. He plans to take full advantage of the long weekend. He pulls her head off of his dick.

“I’m going to order some sandwiches to be delivered from the deli. I will unlock the door, so he can come right to my office door. You will remain naked. You will sit on the sofa, with your legs spread wide apart, allowing him a good view, in case he happens to look in that direction. This is your first test in being my slave. As my slave, it will be within my power to show your body off to whomever I please, wherever I please. If I decide to take you in a restaurant, you will comply. From some of the stories that you have written, and yes, I know that you have written some of them by your nickname, you enjoy the idea of being used in this fashion. I bet you’re getting wet right now at the idea of him seeing your naked pussy, and knowing what just happened to you.” He announces. 

To be continued...