The Choice You Make Remix Ch. 01

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A Supervisor places an intern in a compromising situation.
2k words
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Part 2 of the 5 part series

Updated 06/10/2023
Created 10/17/2020
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"The Choice You Make" was almost exactly the way that my real life happened, almost. It is so close to reality that if you knew the person described, you would say, "Yes, that is her." Some have indicated that they would like a more sexual story. Well, I am sorry if my real life did not live up to your fantasies, so here is the way that my relationship with Brimstone Bree would have continued if I had chosen to go with my fantasies.

I glance over my shoulder as Bree heads to the post office. I usually have to be careful not to let her see me looking. This time she is walking out the door and I can pause for an especially appreciative look. Her ass has a nice mature sway to it. Definitely not a skinny college chick! Do I dare stay and see more of it? If I was smart, I would run for my life. Well, I am not that smart and this would probably be my only chance to discover her secrets.

I take a quick peek down the hallway. The first room is a bathroom decorated in a soft but not particularly shocking lilac. The second room is her bedroom with a large king sized bed and generous dresser with a mirror that folds in three sections allowing her to put on makeup from several directions. The furniture is luxurious and expensive, but the print above the bed is more like what I hope to discover.

It is a photographic canvas in black and white, so large that it borders on life-size. It depicts a very handsome naked man hung horizontally in a leather harness with a very large and stiff cock hanging down beneath him. More important than the man however is Brimstone herself standing beside the man caressing his face and turning him against her ample breasts. So apparently her demeanor is not simply a facade.

Of course, I take a quick perusal of the rest of the room. The left-hand drawer in her dresser seems like workout clothes; yoga pants, sports bra, t-shirts. It is hard to believe that someone of Bree's generous proportions works out, but I have heard her talk about exercise so perhaps she is among the unfortunate ones who cannot lose weight. It's not my problem. I like larger women and it is better not to think about your supervisor as a sexy woman. She is more of an abstract force, at least, until now. The second drawer is slips and nightgowns and a violet vibrator. I am not impressed. She has more and worse sitting on her desk at work. I continue my inventory swiftly around the room. It is not always clear if her clothing is intended to be worn in public or private. I have seen her wear the leather dress in the office and never seen the pink babydoll at all. The latter seems too small for her; She might have worn it when she was younger. I do not know how long she will be gone, so I am not going to spend too much time cataloging her clothing. I was disappointed not to discover the harness that the man in the photograph was bound by. There are not any hooks in the ceiling, so I know that the picture was not taken in her bedroom and a third person had to take the photograph, so who knows where she was at. I rush back to her living room, before I am caught snooping or I might end up really bound in a harness like that and spanked and whipped by the implements that she keeps in plain sight back at the office.

There is no doubt that Bree wants me to be her latest conquest. Why else create this lame excuse to invite me to her house? It is well known that she likes younger more servile men and I am the perfect candidate. I am 30 years younger than her. I am polite to a fault with girls. The thought scares me and excites me. My stomach has a pit in it that is matched only by the tingling in my groin right beneath. There are the obvious career advantages and disadvantages, but my young libido is drawing me more to the potential in my groin.

Bree is not every boy's cup of tea, but oh! I love her rubenesque figure! Her thick hips are unabashedly soft yet mature. I would let her lay me across her lap and spank me red. While some men would be put off by her waistline, no man is turned off by her breasts. I could imagine being flipped over after a proper maternal spanking and being comforted by smothering my face in her double D's. How often had I seen the edge of her areola peeking above the edge of lowcut outfit that she would routinely wear to the office. It was constant temptation to glance lower and I am certain that on more than one occasion she caught me glancing and noticed my blush when I thought she knew my stare. I am equally certain that she did this on purpose as a way to manipulate men with combined desire and fear of retribution by her claims to feminism. Bree knew how to bully men into doing what she wanted.

I get hard as I pick up the bikini left on the white leather couch. The fabric is a shiny grey and the cut is too small and tight to really seem functional. The waist size seems about right, but it really is more of a thong than a bikini and the front dipped down so that it ought to cover my balls, but I might not be able to get my cock in it. I am above average in size, probably not the largest in the world, but certainly larger than what this little slip of fabric can hold, particularly if I get hard. Of course, even an average size man would have trouble in this little piece of swimwear if they got hard. Maybe I should wear my underwear instead.

What am I thinking? Maybe I should get out of here! The pit in my stomach is all the worse for my foray into her bedroom. I feel like she could return at any moment and catch me even though my slight dip into voyeurism was done and it is unlikely that she will ever know that I took advantage of a private moment in her house.

If I was to wear my tidy whities, the instant I hit the pool they would become as translucent as a big-breasted girl at a wet t-shirt contest. But this is Brimstone Bree! She makes no secret of the fact that she has seen plenty of cock. She gave me these bikini bottoms that no self-respecting man would wear. Why do I call myself self-respecting? It might be fun to let go of some of that self-respect and just be a stud with a sexy older woman. She had me here to see my cock. She probably wants me to get hard. I can imagine her putting on a swimsuit and joining me in her pool. sliding up to me and rubbing her hands over my groin, pulling my cock out and stroking me, taking me to her basement or another part of the house that I had not looked and chaining me to a leather clad bench to spank me.

There is a wooden paddle beside her desk in the office. It looks like it has been carved out of a 1 x 6 and drilled with holes to give the paddle more sting as it strikes a man's backside. I am not a masochist. I don't pinch myself with clothespins or spank myself with a whip when I masturbate, but somehow when I enter Bree's office and see the whips on the walls, I think of what it might be like. If I ever do experiment with sadomasochism, it might not be a good idea to start with somebody who makes no secret of her somewhat sadistic personality. I could end up handcuffed across the leather couch in front of me being kicked right in the balls. The thought turns me on, but only enough to add a deeper pit of fear in my stomach. Would she stop if I said enough? Would I cry and beg for her to let me go? And if she did, would I cry and beg for her to keep hurting me? She is so over the top; I have no idea if she even respects limits and I don't know if I could take her punishment. Mom spanked me once in junior high. Certainly none of my girlfriends would even suggest it. They may have wanted me to do a spanking, but none of them have the maturity or the desire to be in charge. Bree is her own woman and mature enough to decide what she wants for herself and for her man.

Do I dare become that man? The thought is arousing. I am getting a hard on and Bree is not even here. I so want her to lay me across her thick thighs and let her spank me like a little boy, force me to give up control, make me cry like a toddler, then afterward lay my head against her breast and comfort me while she tells me how much she has come to appreciate working with me for the last few months and how she will keep me as her personal toy from now on. My cock is throbbing with the mere thought. I am not touching myself, but I feel like I could cum right now, right at this moment in my jeans. Damn it! I am going to do it! It is only an internship. If I overstep my bounds and she fires me, then what have I lost? The opportunity to work for free?

I tug my clothes off right there in the living room, forget to kick off my tennis shoes in my haste and nearly fall on my ass. After I am naked, I pick up the thong that looks like it could be ripped from my body with one quick tear, but may bind me harder than a steel chain and put it on, sliding it into the crack of my ass. I try to stuff my cock into the front. Damn it! I have a hard on and as I suspected, there is no way that I am going to get that covered up. The bikini does cover my balls, but is not designed to cover a hard on. I look up at the ceiling and try to relax staring at the rotating ceiling fan, but forcing myself to relax only makes me harder. I fiddle with the swimsuit to find a way to cover my erection. Here is the trick. It is designed with a pocket to slide your cock in and keep it trapped once it is on. The pocket also conveniently shows your meat off to the ladies. I want to know who the sadistic fashionista was who designed that! Probably was Brimstone Bree herself! Okay, just relax and breathe normal!

Except that is her car in the driveway! I run to peek out the front door and there she is climbing out of her sports car and coming up the walk. Okay! What to do?! I grab my clothes and decide I need to run to the bathroom, change back and simply tell her that it would not fit. I grab my clothes and put them in front of me as a fig leaf to run for the bathroom. As I do so, I realize that in my panic, I had lost my erection and I can tuck my cock into the appropriate pocket just as Bree opens up the door.

Bree asks, "You haven't got into the pool yet?"

I say, "No, not yet!"

She says, "Well, go hop in. I'll put on my swimsuit and join you. You can leave your clothes on the dining room table."

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