The New Boy

She hated waiting. She especially hated waiting in line. She most especially hated waiting in line at the post office. Still she had parcels to post so she had no choice, but to wait. So she waited on the postal worker to wave her over to the next available window.

Fortunately the line was not all that long today. She stood quietly, motionless as she looked at her fellow waiters. She noticed one young man just ahead of her. He seemed agitated or nervous or something, he could not stand still. He was a very attractive although a much younger man than she knew she should have been observing. As if he had sensed her eyes on him, he turned to face her and smiled slightly. She acknowledged the smile with a smile of her own. He then resumed his original position facing forward in the line.

There were suddenly more windows open and the line dwindled fast as each customer was handled quickly to conclude transactions before the office closed for the day. In the sudden rush she lost sight of him and his presence slipped her mind until she made her way to the parking lot for her car.

It was autumn so the sky darkened quickly and the parking lot lights were on, she had parked beneath one so her car was easy to spot. Apparently the young man was parked near her because they walked towards the same area.

She got to her car just as he stood next to the car that was directly in front of hers. There was an awkward moment of silence as they stood and stared at each other. Finally he spoke.

"Hi, nice night, huh?" He said, a slight smile playing across his lips.

"Yes, yes it is." She said, wondering why he had even initiated a contact.

"I'm sorry, I don't mean to be forward but I noticed you inside and caught myself thinking that you were a very attractive woman. Someone I would like to talk to, if that's alright?" He stood there in a very non-threatening stance and seemed eager to engage her in conversation.

She was momentarily speechless. She had always been told she was pretty but had never considered what that really meant to those that had said it. She considered herself rather average. Average height. Average weight. Average looks. Just you're average over 40 brunette.

She took a closer look at him. He was obviously younger than she was, rather tall, slender with long hair to his shoulders and a full, yet neatly trimmed beard. His coloring was typical of the blondes, fair skinned and light eyes.

He broke her inventory by saying, "Again, I'm sorry, I don't mean to be rude, it's just that..."

She interrupted with "Oh, it's alright, it's not often a young man approaches me like this."

His smile widened as he asked, "Well, then let me take this one step further and ask if you'd consider joining me for a coffee at that restaurant across the street?"

This took her aback and as she tried to come up with a response, he walked towards her. She wasn't sure if she was to be flattered or alarmed. They were strangers. It was getting darker by the minute and the parking lot was clearing out leaving her alone with this man.

Finally, she spoke, "Well, ordinarily I don't just go off with someone I just met but for some reason, I think I'll make you the exception. I do think we should re-park our cars in that lot though. I'll meet you there in a moment." She got into her car as he hurriedly returned to his.

They pulled up next to each other in the lot. Neither one spoke as they entered the restaurant, found a table and sat waiting on the waitress. In a few minutes she came and took their order of just coffee.

She sat still and quiet while he sat grinning and twisting his napkin nervously.

This time she broke the silence by saying, "So do you want to start with the usual, like name and occupation?"

"Oh, sure. My name is Michael and I'm photographer." He told her obligingly.

"Well, hello, Michael the photographer, my name is Nancy and I'm a professional dominatrix." She giggled as his mouth dropped.

The awkwardness of the moment was diverted by the arrival of their coffee.

Michael seemed to become intensely involved in getting his coffee creamed and sugared just right, his eyes averted from her face. He even blushed.

She assumed she had embarrassed him and said, "So its my turn to apologize, eh? I'm not what most people expect and from the look on your face, red cheeks and all, certainly not what you were expecting me to say."

"No. No, its not that...uh, what may I call you?" He said, his eyes downcast and his physical presence much more subdued than before.

Nancy took this to mean he was asking her permission to address as a domme and said, "Well, then Michael, Mistress is just fine, but I'm off the clock so to speak.'' Again, she giggled like a young girl.

He glanced up at her and said, "Oh, yes of course, I understand, I think. Being a domme is your profession, something someone would have to pay you for doing. I, well, I..I don't know what to say". He seemed to deflate into his seat.

Well, this is becoming rather interesting, she thought. Her usual clientele were older men and a few women that paid handsomely for her services as a dominatrix. She was quite proud of the reputation she had carefully built up over the years in her community of like-minded people. Not one for needing to be limited to one relationship, she had some long timers but more first time clients. This had gotten her to be known as "The Cherry Popper".

"So how acquainted are you with the BDSM community, young Michael?" She asked, looking directly into his face.

"Uh, well. I've no direct experience, yet. Its just something I've sort of kept up with for a while mostly online. You know the websites and chatrooms." As he spoke, he kept eyes downcast.

"Alright. So the terminology is not strange to you but you've not actually submitted to anyone, right?" She asked as she watched his body reactions more intently.

He continued to not meet her gaze and said, "Yes, Mistress. So maybe our meeting is kismet in some way. Maybe you are the one to show me what it's like in real life? Again, I hope I've not presumed too much. If so, I beg your indulgence, Mistress."

"Uh, huh. I think you should understand I have a certain reputation in my community, one that might be altered if I were to engage in a non-professional, meaning free, relationship with someone. Still you do intrigue me. Maybe its time we took this conversation somewhere more private? And also, keep this less formal than I would ordinarily when cultivating a new client. You may call me Mistress if you like but I'm in the mood to be a bit more lenient and less structured than usual." She was pleased to see him raise his face to her and look her in the eye.

"Yes, something less intense than the traditional sounds more like what I could handle for now." He motioned for the waitress to bring them the bill. He paid at the register and then followed her out to their cars.

Nancy suggested they meet at a motel not far from there, a place she had used before for trysts. She got into her car and drove off without waiting for a response from him. She smiled slightly as she looked at him through her rearview mirror as he watched her drive away. This would be the first test. Whether he would follow or drive off.

It didn't take long for him to pull up beside her in the motel parking lot. She stayed in her car and motioned for him to come to her window.

"You play, you pay." She said in an even tone.

He went to the office and paid for a room. Then he walked down the sidewalk to a room at the end. She was right behind him.

"Sit in the chair by the window". She said as they entered the room together.

He did as he was told. She drew the curtains closed and sat on the bed facing him.

"It has been a very long time since I had vanilla experience with someone but I think it would be appropriate now. I'm in no mood to domme today. What I do want is to be pleasured by a man who knows what he is doing and will do whatever it takes to make sure I am completely satisfied. So this is a kind of test of you as a lover. If the sex is good enough then maybe that might lead to something more like what I ordinarily do. Are you still interested? Just having sex?"

"Uh, yes. I would be very happy to please you, Mistress, I mean Nancy." He said, a bit of a tremor in his voice.

"Well, then. I will be a bit directive, I just can't help myself, so first things first. Take off your clothes. Slowly, introduce yourself to me a little bit at a time. Would you prefer music or silence?" She settled back into the bed waiting for the show.

"Uh, I think quiet is fine.'' Michael said as he unbuttoned his shirt. He stood at the foot of the bed removing one article of clothing at a time until he was naked from head to toe.

She was duly impressed by his well toned, muscled body and an obviously rising erection. His cock was what she would have expected on a man his size. Although rather noteworthy for the speed at which it became hard.

"Now I want you to use your hands on yourself. Start by using both hands to touch and caress your face. Then work your way down your body, slowly. Stop just before you reach your cock. I want you to focus on how it feels to you."

Michael put his hands to his face, touching his mouth, for a moment his fingers lingered on his lips. Then his hands continued down pausing at his nipples that were now also hard and erect. Slowly his hands drifted to his hips and he stopped, his breathing having become deeper and more irregular.

"Tell me what you are feeling, Michael."

"I...feel aroused by my own touch. I ...feel like I need more than this. I...I'm wondering.."

"Quiet! Michael, this is about feeling. This is about self-awareness. A true lover knows his own body well first. Now, masturbate as if you were alone."

He looked up at her quickly. Confused. He started to speak and she shushed him.

"Michael, jerk off! I know you know how. You must stop short of cumming though. So, begin..."

Hesitantly, he grabbed his cock, stroking it.

"You must focus on the sensations. You must become aware of your need to cum. But you must not cum until I allow it. Understand?"

"Oh, uh, yes." He said as he stroked himself, eyes closed, his whole body posture changing in response to the self-pleasuring.

She could tell he was close to cumming. "Michael, now come here onto the bed with me, do not take your hands off your cock, least not yet."

He clambered onto the bed awkwardly next to her. She arranged him so he was lying down as she straddled him just below his hard, erect cock.

"Now watch me, Michael. Do not take your hands off yourself but stop stroking and watch me."

Once she had sat on the bed when they first entered the room, she had removed her heels. She wore a simple, black, knit wrap dress, which came off quickly. His eyes widened in appreciation of her lingerie. Black silk bra and thong. She slipped out of her bra and unsnapped the sides of the thong. Then she was naked on him in a cowgirl like position.

By the look on his face it was apparent he was almost to the edge of no return by seeing her bountiful breasts unbound and having her discretely shaven cunt so close to his cock. He was moaning as if in pain from the denial of his need to fuck her.

"Oh, I think we are ready to proceed. I want you to touch me with your mouth and hands as I hover over you." She moved her breasts over his face as his hands found her. He took a nipple in his mouth and sucked while his other hand massaged the other breast.

She quit talking as she got lost in the process of moving over him, giving him access to her body with his hands and mouth. He was very skilled in making her feel pleasure by kissing, sucking and stroking every inch of her body she presented to him as he lay there.

At different times in all this movement she could feel his still rock hard cock rubbing or poking against her.

Then she motioned for him to move down so she could straddle his face. She wanted his tongue in her cunt.

He quickly obliged and greedily kissed and licked her wet pussy. Covering her mound with his mouth and massaging her ass with his hands. She came hard on his face. He responded by probing her cunt deeper with his tongue and fingering her clit until she spurted in his mouth.

Now she wanted him inside her, so she repositioned herself to ride his cock. It was not long before his was bucking up hard, groaning.

Barely audible, through gritted teeth, she spoke. "Michael, you must ask my permission to cum."

She intentionally slowed the rhythm down, holding off his release, taking full advantage of his cock deep inside her. Tightening and releasing her inner muscles, rubbing her clit hard against him, she came again and again. Sensing his was about to burst from need, she slowed her pace just a bit.

Barely able to speak he pleaded, 'Nancy, oh Mistress, Nancy..please. Please. Let me cum..."

And then she said, "Yes, Michael. Cum for me! Now. Cum for me!"

Michael's body tensed as he bucked up furiously, slamming into her cunt, finally releasing his load, he grunted "Thank you, Mistress".

They lay next to each without speaking. She was thinking, as her breathing returned to normal, that it had indeed been a long time since she'd had sex without any restraints or toys. Simply being directive. It was better than she had remembered but still the thought of using Michael with her usual bag of tricks made her shudder with anticipation.

"Michael, you are naturally a good lover. You do know what to do with your body to please someone. I think this could just be the beginning of something very special. I can teach you more but you have to be willing to learn. Are you willing to learn? To submit yourself to me?"

"Yes, Mistress. Yes! I will do whatever you ask of me. I want only to please you, Mistress!"

"Well, then. You are now my private pupil. My special pet project. This is not to be a public arrangement. No need to change how my paying clientele see me. As soon as you leave here, go someplace to purchase a cellphone exclusively for our use. Then call me with that number." She grabbed a notepad and pen out of the nightstand and wrote her phone number for him. "This is a private line. When we meet it will be either here or someplace like this. You will always arrive first and pay for the room."

Nancy went to the bathroom to clean up and dress leaving Michael to dress in the room.

They stood at the foot of the bed, embrace quickly and she kissed his cheek.

"Oh, Michael. You are going to be my very good boy now, aren't you?"

"Yes, Mistress. Yes, I will be your very good boy."

She slapped his butt playfully as they left the room.