Side Tracked Ch. 15

Chapter 15 - Traveling in style

Mistress Diana and Sam

"Waiter, would you please get someone to go into the 2nd class carriage and get my assistant. He sleeps in bunk number 3 and have him bring me the folder of the Saturday Evening Post article I'm working on."

"Yes ma'am, I'll be glad to do it in just a minute, as soon as I finish setting up lunch."

"Ok, then I'll have a ham and cheese sandwich while I wait."

"Yes, ma'am."

With that, she turns back to the proof sheets on the table in front of her and starts to make notes with a pencil. The book she had been working on for the last year was almost ready to be printed. She gets so caught up in the work, she doesn't notice when the plate with a sandwich show up in front of her.

"Ma'am, you sent for me?" he interrupts her thoughts, as a folder is laid onto the table.

Looking up, she smiles and says "Thanks, Sam. Get yourself some lunch to eat and then go and get my room ready for me, I'll be back as soon as I finish this set of edits." as she spots the sandwich in front of her and reaches for it.

"Yes ma'am" he says and turns to head over to the buffet. After eating a sandwich, he heads to her room to do as she asked.

Watching him go, she smiles and returns to her work.

An hour or so later, she cleans up the table for her papers, puts them into her briefcase. Getting up she drops a quarter, as a tip and heads back to her room.

Reaching there, she opens the door and steps into the room. On the floor in front of her, is her plaything. He is on his knees, legs spread wide, with his cock in his hand. She stops and watches as he continues to move his hand slowly on his cock, hard and protruding out of the top of his fist. His knees on on a small pillow, his back is arched so she can watch him beat off and of course he is nude, as all good playthings should be.

"Good boy, I want it nice and hard, for I have a use for it later to day. Now get up and get me out of this outfit."

Sam stands up and walks over to her. Reaching out, he starts to unbutton her dress top, as she reaches out and jacks his cock. She has always enjoyed the feel of a nice hard dock, and this one was very nice. Standing there, she let's go of the cock, to let him undress her. As each item is removed, it is neatly folded and piled for later packing in her traveling trunk, she smiles at him as he follows his orders. As she steps out of her bloomers and stands there just as nude as her plaything is, she watches as he has follows her instructions on the handling of her clothes.

She walks over and sits on the bed and gestures him to stand in front of her. He walks over and stands where she indicated, his cock protruding in front of him. Leaning down, she sucks it into her mouth and closes her eyes, as she feels it slide into her. The softness of the skin, the hardness of the shaft and the little bit of leakage at the tip, starts to turn her on.

She knows, she is on a power trip with this 25 year old man, almost half her age, but that is what she enjoys. Over 10 years ago, she joined the women suffrage movement and had helped to get the votes for women in Wyoming. She believes that women are more powerful than men and has over the years taken over many men and made them into her playthings. The one before her is a good example, hired as an assistant, she has over the last few months turned him into her sex toy and he seems to enjoy it. As she sucks on his cock, she knows he will not cum without her permission and she is not ready to give it. She will get him close and through her control of him, stop him from finishing.

As he starts to pump his hips into her mouth, he closes his eyes and enjoys what is happening, knowing he is not to cum, he has learned to enjoy the playing before cuming and because he knows this, he will not cum until she orders him to. She is enjoying the feel of him, fucking her face and also the enjoyment of controlling him and stopping his orgasm is one of many ways she controls him. The power of doing just that is a real thrill to her. She likes her power of controlling this horny young man. She enjoys making him do what she wants, not what he wants.

Just like right now, his thrusts are saying, I'm going to cum soon, but she knows he will do what she says.

"Mistress, may I cum?"

Pulling the cock from her mouth, she says "No my plaything, do not cum. Stop whatever you are thinking of doing, drop to your knees and lick my pussy, now."

In direct response to her command, he stops thrusting his hips and starts the process necessary to keep from cuming. He knows, if he cums, he will disappoint his Mistress and some kind of punishment will follow. Working hard, he is able to stops his drive to the orgasm, that he had been building.

Dropping to his knees, he opens her legs and leans in to lick her pussy. The hair around it is trimed short, he had done that before starting on this trip, so he has easy access to her slit and the small hooded thing at the top that she likes to have him lick. Hiding behind the hood, is the small nub that she does not like licked directly, just the circling of his tongue around it. Lowering her hand, she takes over and moves his head so that his tongue and lips where she wants them. She also likes this part, controlling this man between her legs. But, as she nears her first orgasm, she realizes she needs more than this little bit of control of him. Today, she wants to take over and have him fully under her control. As she starts to orgasm, shuttering through the feelings that his tongue causing her to cum, she is already starting to plan the next step. She smiles, as soon as she finishes this one and closes her eyes to enjoy the orgasm caused by her plaything licking her, just as she trained him to do. Lying back as she finishes with her legs spread, he continues licking her, cleaning her up and waiting for her next command, just as he should be.

As she settles down, she looks down at him, at her feet, and says. "Get the harness out with the dildo selections. I went to fuck you and I need to get the correct dildo?"

He now knows what is coming next and starts to prepare mentally for getting fucked in the ass by his Mistress. When she does this, he has very little to do with it, but to be the recipient of her power of control over him. He knows that she does this to prove to herself that she is in control of him, what she doesn't care about, is if he enjoys it, all she wants is that he does what she wants when she takes over.

While traveling her dildo collection is small but it has her favorites. There is the long wooden round one with a handle for her pussy, a short ivory one for her ass with the wide base to keep it from getting lost and finally a long, slightly curved one of ivory designed to be used with her harness for her plaything's ass. Looking over them, she gets lost for a moment in the memories of past experiences. Picking up the one for her plaything, she smiles as she remembers fucking each and every one of the past playthings. She fucks them, some for the humiliation, others for the pure joy and some just to prove she can. She wonders what this one will turn out to be.

"Put the harness on me, mount the dildo and then get into the ass high position, my plaything." She says to him and watches as he gets out the leather harness and the matching ivory cock. He then runs the belt around her waist and the straps between her legs to be buckled in the back. A triangle in the front holds the fake cock sticking straight out towards his face, as he sits back on his heels.

Looking down at her plaything, she says "Kiss my cock and then assume the ass up, face down and arms spread position"

He leans forward and kisses the fake cock, then turns around and assumes the required position. His ass is high and the cheeks are spread wide. She takes a jar from her travel trunk and opens it. Taking whale oil, boiled down to the consistency of grease and spreads it on the ivory dick she is wearing. Leaning forward, she spreads it down between his ass cheeks and over his asshole. Running a single finger into his ass, she greases it. As she moves her finger deeper into his ass, she lubricates the inside as well as the outside of his ass. Moving her finger, she feels his hole loosen up, so she adds another, widening his hole more. A third finger is added and she starts to move it deeper in and then pull it back out, fucking him with her fingers. Pulling the hand out, fully, she adds more whale oil grease and slides it back in easily. As she does this, she feels him start to rock, forcing her fingers deeper into him

"Are you ready to be fucked by your Mistrees? "

"Yes, please fuck my ass, Mistress. "

Taking a hold of the ivory shaft, she aims it at his ass and using her hips, starts to force her fake cock into his ass. He is now up on his hands and knees and rocks back, shoving the fake cock further up and into his ass. She now starts using her hips to shove that fake cock into and out of his ass, fucking him. His breathing now starts to match her strokes, in when she pushes the cock deeper and out when she pulls back for another stroke. She now speeds up the strokes, her feeling of being in control of this man, starts to climb. She really is enjoying fucking this man in his ass, making him take whatever she wants him to receive, even an old ivory cock.

Pulling out and standing up next to the bed, she says "Roll onto your back and take the Amazon position." She orders him.

He rolls onto his back, spreads his knees, lifts his legs to his shoulders and exposes his wide open asshole and his cock and balls above it. Stepping back in, she reinserts her fake cock beck into him and started to stroke again. Looking down at him, she says "Start jacking your cock so you can cum when I order you to."

"Yes Mistress" he answers, as his body is bounced by her thrusting into him. Reaching down, he takes his hard-on cock and starts jacking it in time to her thrusts. He knows that he has to be ready to cum, when she is ready for him to cum and also knows what will happen if his does not cum on command.

She looks down and watches him run his hand up and down his cock, in time to her thrusts into his ass and can feels him working up to an orgasm on her command. Wanting to prove who is in control of his orgasms, she watches him get closer and closer to cuming. As he is almost there, she stops thrusting into his ass and says "Freeze!". As soon as he heard that word, he stops all movement and just lay there, with his cock in his hand. He is almost ready to cum, but on that command he stops the effort to reach the orgasm that he wants. In this position, he is under her complete control and just wants to do what she commands him to do.

Very slowly, she starts to slide her fake cock in and out of his ass, again. With him in a 'Freeze', he can't do anything, until she let's him move again. So, he lays there, cock in hand, feet up in the air and ass full of his Mistresses fake cock. After a few strokes, she says "move" and releases him from his freeze. At that command, she feels him start to beat off again and feels good that he followed her commands.

Picking up her pace, she starts to pound his ass as she looks down at him masturbating, trying to get ready to cum, on her command of course. "Mistress, may this one please cum." Is heard over the sound of her fucking him.

"Yes, cum for your Mistress. Cum now!" Looking down, as she slides her fake cock deep in to him, and watches as he tries to cum for her. Lifting his hips to receive a deep thrust of her fake cock, he arches his back and shoots a stream of sperm up between them. She stops thrusting, as she watches a second and then a third stream of cum shoot between them. As she pulls out of his ass, he is just finishing his orgasm with a dribble of cum.

Sitting up, between his legs, she watches as he recovers from his orgasm. Reaching for a washcloth, she wets it in the basin and hands it to him, so he can clean up. Looking up at her, sitting back with that long fake cock, standing up between then, he says "Thank you my Mistress ".

She smiles, for he had cum on command, even with her fake cock up his ass. He is turning into a very good plaything, but now was her turn for another orgasm. Standing up, she says to her plaything "Your welcome, you did good, cuming for your Mistress on her command. Now it is time for you to get your Mistress off again. Let's start by getting this thing off me, so you can eat me and maybe get me to cum."

Sitting up, her plaything finds that his ass is sore, his back hurts from that last position and that his cock has shrunk back into it's self. Reaching out, he unfastens her leather strap-on and removes the fake cock. Putting it to one side, in order to clean it, he marvels at something that large and long can be shoved up his ass. He also is thinking that he would like it to happen again as it did, at times feel good and Mistress seemed to enjoy fucking his ass.

As he gets up, Mistress rolls onto the bed, with her knees spread wide and her legs off the edge of the bed. After setting down her harness, he leans in finding her pussy wet, he starts to lick her. He closes his eyes and tries to remember her instructions on how to eat her pussy. A lick here, a flick there and some fucking of her cunt with his tongue, he starts her on the climb to an orgasm.

As he licks her pussy, she reaches down and holding his head, she guides him to where she wants him to lick. Having him between her knees, a handful of hair being used to guide his head, she again feels in charge and starts to enjoy herself. Lying there, she feels herself start the climb to an orgasm and using her plaything, she is able to control how and where she will cum. She hits the top and orgasms, as he licks the best spots to help her cum.

Pulling him up onto the bed, she turns to lay the length and holds him to her breasts. He slides his head between her breasts, and snuggles down for an after noon nap. She smiles as she feels him start to hold her, one hand on her butt, and another on a breast.

Laying there, holding each other, they fall asleep.

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