The Making of a Man Ch. 04

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Elyse takes on teacher role to help Nick become his own man.
36.1k words
4.61
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Part 4 of the 5 part series

Updated 08/20/2023
Created 01/29/2020
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Author's note: This long chapter involves many different types of sexual content as I further the story along, including a bdsm scene at the intro. If you find a particular scene doesn't appeal to you, scroll through it and you may find more interesting material as you read on.

*****

Part one - The truth revealed

When the knock at the door came, Nick knew it could only be Rachel's pretty, older neighbor, Susan. The lonely one who missed the satisfaction of giving a man head since her divorce years ago. The playful look on Rachel's face told him he might soon find out just how good Susan's oral skills were.

Nick spent the previous night satisfying Rachel but she denied him his own release and now, he hoped, his patience would be rewarded. Still nude, he remained seated as instructed and closed his eyes thinking of Susan.

She was in her early fifties by his estimation but very pretty and well preserved for her age. She was tall and thin with long, wavy blonde hair and pretty blue eyes. Susan wore delicate looking wire framed glasses with small round lenses giving her the look of a librarian, which he found sexy.

Nick believed her best feature was her full, pillowy lips. Since meeting her, he found himself more than once pondering what it would be like to part those luscious lips with the tip of his member.

Nick met Susan for the first time the week prior. Rachel attempted to embarrass him during breakfast by making him remain naked while Susan came over. While he did feel embarrassment, it did nothing to diminish his fierce erection and Susan commented about how pleasing it looked. She even allowed Susan to stroke it briefly and he could still recall how nice her gentle touch felt when she cupped his balls.

She told him afterward that Susan apparently had a blow job fetish which somehow brought about the end of her marraige. Seeing Nick's interest in her, Rachel had teasingly told him several times since that she would probably let him help her out with small handyman tasks now and then so that Susan would have a good excuse to offer him a nice soothing hummer.

Like the week before, someone was coming over now and Rachel told him to remain where he was, completely unclothed. Her sweet words were music to his ears, 'It's not like she hasn't seen you naked before." Nick let out a contented sigh, knowing he was probably going to be inside Susan's lovely mouth before long.

As he heard the front door being opened, he reached down to stroke himself, believing his much needed climax might be only minutes away. He wanted Susan to see his rod fully engorged from the moment she entered the room. Eyes still closed, he lightly fondled the head, swirling droplets of precum under the sensitive tip wondering what she was going to think when she saw this display.

As Nick opened his eyes, his mind screamed out in alarm. Mistress Jen strolled into the room, bold as ever. Her thin lips were curled into a sadistic smile. His heart always raced in her presence, sometimes in elation but more often in fear. This moment, however was all about fear.

Jen owned every room she ever walked into and she knew most men lusted for her, Nick being no exception. Jen had always teased him without mercy yet despite this, he was constantly coming back to her, willing to accept whatever attention she would offer, good or bad.

Confident she had completely taken him by surprise, she walked up beside him and broke the silence.

"Hi Nick. If you're getting that dick of yours ready for me, think again."

He was too stunned to speak but it mattered little as Rachel walked up on his other side and spoke for him.

"He was probably thinking you were my neighbor and how he'd like to get a sweet blow job from her. Isn't that true, you little whore? The look on your shocked face is priceless!"

His mind swirled in panic and confusion as he tried putting the pieces together. He asked himself how Jen and Rachel figured out he had been seeing them separately and on the sly but a more important realization set in that they now believed he betrayed them both. He thought about the new relationship he was trying to create with Rachel and feared it was about to end in the coming minutes. Just thinking of it made it hard to breathe.

Rachel looked down at him and continued, her tone becoming more icy.

"I know about the time you and Jen have been spending together. You're not that clever, Nick. She and I have been toying with you from the start, tag teaming you and comparing notes at every turn. You never had a chance against us."

Her attitude shifting back to more playful, "You know baby, it wasn't very nice of you to use your boyish charms to flirt with Jen. You got her so worked up that now she wants to spend even more time with you. And I'm going to see that it happens."

Nick found himself confused not knowing if this was them playing around with him. In the pit of his stomach, he worried that something had changed here and possibly for good. Mistress Jen ran her fingers through his hair, distracting him. Before he took too much enjoyment from the simple gesture, she grabbed a fistful of hair and painfully yanked his head back. Towering over him, she brought her face closer to his and softly spoke.

"Nick, before I got to know you, I was strong and confident. I brought men to their knees and they would drink my piss if I told them to. Then you came along and made me soft. You were different from the others and I even found myself falling for you. You played cute and innocent in your efforts to try and fuck me, completely ignorant to how dangerous I really am. Now that I've regained my strength and come to my senses, I'm going to show you my darker side. With Rachel's permission, I'm going to make you my bitch!"

"Jen darling, you have my blessing to do with Nick here as you see fit. He and I will be taking a break from one another starting today. I'm anxious to see him once you've trained him up some."

Turning to Nick, she added, "You need to settle up with Jen now. I'm going to run over to my moms while Jen gives you a taste of things to come. When I get back, you and I will have a little chat."

He didn't even have a chance to respond as Mistress Jen yanked him out of his chair, ordering him to his hands and knees.

"Stay put while I go through my bag of toys. And not a word out of you either. We'll wait for Rachel to leave before we get started. She's always been too soft on you and might object to some of this stuff."

As he held his position, he tried telling himself that this was just another wild and sexy situation they were creating for him to keep him off balance as they so often did. This time was different though as they were working together and worse still, Rachel said she wanted to pause their relationship which really took him by surprise.

Nick felt slightly sick over the idea of not being with Rachel but he had learned to trust these women. Surely they were only screwing with his mind. He tried arousing himself with imagery of Mistress Jen when she was feeling more generous and playful, hoping to displace some of the anguish he was feeling.

Jen was in her early thirties, very short at 4'11" and extremely petite. Her tiny body couldn't weigh more than ninety pounds, Nick thought, but every inch of her was lean, sculpted muscle. Jen didn't spend a lot of time in the sun leaving her skin lighter in color yet beautiful against her other features. Jen usually colored her hair and cut it in a short, cute but sassy style. Nick was used to seeing her as a blond but today, her hair color was a rich shade of red he hadn't seen on her before.

Even in play, he had never seen Jen without some type of garment that covered her neck, shoulders and arms but he longed to strip her down completely and play with her small breasts, spending time finding out how sensitive her nipples might be. He knew she had a number of hidden tattoos and once, she commented that she might let him become the first man to ever see them.

If Jen were an animal, he thought, she'd certainly be a tiger and a wild one at that. She was beautiful, exotic, powerful and dangerous yet whenever she focused attention on him, good or bad, all he could think about was running his fingers through her fur in a desperate attempt to soothe and please her. He dwelled on that thought, trying to will his erection back to life.

Jen couldn't help but notice that Nick's hard on had completely shriveled up in all the drama. 'He's scared shitless,' she thought and it occurred to her that she was really enjoying his fear. As much as she reveled in it though, she also wanted to find the perfect balance point with him where she could maintain his anxiety along with his excitement. After all, she thought, his dick wasn't much use to her in this state.

Sex appeal and sensuality along with equal portions of cruelty and volatility would create the balance she sought. Always struggling with her own emotions, she had finally convinced herself that the key to regaining her sexual equilibrium was conquering that which nearly unraveled her. Having Nick at the end of her leash, so to speak, would be her way of controlling feelings she would probably never understand.

Jen studied Nick as he remained still on all fours, faced away from her. When she permitted him to stand, he rose to a full 6 foot tall. A former student of hers, she saw him fill out in his senior year but now that he worked with his hands for a living, she noticed his muscles growing even faster and becoming nicely defined, particularly across the shoulders.

One area of a man that turned her on most was the midsection. Jen was a fanatic with maintaining her own lean body so when she found men who did likewise, she valued the hard work and discipline it took to do this. While his muscles were growing thicker, he had kept his body lean and tight.

Jen always thought of Nick as very handsome with his short, sandy brown hair and dark eyes but since she had been playing with him over the past few months, she found herself daydreaming of him often. A few times, he stood before her and kissed her passionately, nearly overpowering her strong will. Today was necessary to convince herself he was just another toy and not some young heart throb who was going to sweep her off her feet.

Not for the first time in the last few months, Nick found himself revisiting how he got to this crazy place in his life.

Less than four months ago, he had never even kissed a girl but practically overnight, he was aggressively seduced by both Rachel and a gorgeous older neighbor named Elyse, whom he did yard work for. Both women wrapped him around their finger and made him their play thing. Neither knew of the other, so he believed, and he tried to juggle his time between them, all the while keeping both of the demanding women satisfied.

To add to the erotic turmoil, he had also been pursued by Jen during this same time. She had been his English teacher in high school and every guy at school, including fellow teachers, wanted to plow their dick into her. Jen knew this of course and adjusted her dress and behavior as provocatively as she could get away with to keep them all drooling after her. Nick knew that she always had to rule the world around her and he loved the way she was able to control him so easily.

Jen kept Nick wound extra tight over the months, allowing him only one orgasm during all those encounters. When she said she could make a man drink her piss, he believed it completely. As disgusting a thought as it was, he knew he'd probably be the first in line to taste her fluids, satisfied in getting whatever she was willing to give him. 'How could this woman hold such power over me?' he asked himself.

Once Rachel left, Mistress Jen wasted no time. He remained on all fours but she had him bring his knees up tighter while she grabbed his nutsack, pulling it uncomfortably back between his legs. His anxiety hightened as she fastened some sort of device to them, trapping them in the stretched rearward position.

"I've just attached a devious little tool to your balls appropriately called a Humbler. If you try to stand or straighten your legs, it will rip your testicles off. There is no way for you to remove it and you are totally at my mercy. Let me show you what I mean."

Out of nowhere, he felt a stinging blow to his vulnerable sack. The sound of the slap registered milliseconds before the pain but the effect was the same. He instinctively lurched and in doing so yanked his jewels very painfully. He screamed out and nearly faceplanted into the floor in his haste to cradle himself.

For a moment, he was certain he had permanently injured himself. Jen had always played rough with him but this was far beyond what he had experienced before. He didn't want to play anymore but something about her intensity today told him he wasn't going to be allowed a way out.

Gasping for breath, he blurted, "Oh damn! I think I hurt myself!"

"You'll be fine. That was just a little kiss to make you acknowledge your vulnerability. I can hurt you far worse than that and I will if you don't pull yourself together and do as your told. Stop touching yourself and get back onto your hands, nice and straight like a little pony bitch waiting for his Mistress to mount him. Eyes front."

He did exactly as instructed knowing the only way through this situation he was now trapped in was the path she had already planned. The pain diminished quicker than he thought it would and he reminded himself he could do this and might be able to enjoy it if he relaxed.

Nick listened to her behind him, hoping for some clue as to what was coming next. A flyswatter was tossed out in front of him ending the mystery of what she used on his exposed stones. He heard the sound of a buckle being unfastened and his first thought was he was about to receive a whipping but then it was followed by the sound of a zipper and pants dropping down.

In that brief moment, his thoughts rested on the idea that she was about to sodomize him with a strap on. Scary as the idea was, he knew that this was probably the kind of thing this unpredicable woman might do and his dick started to stir for some reason.

Nick was torn between relief and disappointment as he heard shoes being kicked off followed by her playfully tossing her clothes out in front for him to see.

Jen felt a surge of power when she hurt him but her conscience told her to turn it down a couple notches so she didn't injure him. She came up behind him and laid herself across his back. Gently running her hands underneath, she stroked his chest, teasing his nipples until they were hard. Using her nails, she pinched them harder and harder until he cried out. Someday, she mused, she be putting clamps on them and he'd be whimpering for sure then.

Moving her hands down, she lightly caressed his sides and belly, admiring the rippled muscles. Moving lower still, she found his swollen cock and played with the head. He moaned and this only heightened her excitement. He was leaking profusely and a strange curiosity overtook her. Without a thought, she swirled up the liquid and tasted it. She did this several times, enjoying the flavor when suddenly it hit her that she was losing herself in him again.

Jen scolded her own weakness. She rarely took a man's penis into her mouth and she certainly never longed to taste a man's semen.

Trying to regain her composure, she sat up and gently climbed onto his back, settling herself into the small of his back. Once again, she felt a surge of passion for him. She questioned why all this was really necessary when she could simply release him and have him fuck her to her heart's content. As she adjusted herself, her wetness across his smooth back provided an incredible burst of sensation and she let out a soft moan.

Whatever may have remained of his anxiety gave way to exhilaration as he felt her warm, bare skin against his. His rod sprang to life as she stroked his belly and teased his hardened nipples. When she played with the precum from his penis, he could swear he heard licking sounds.

As she lifted her feet off the ground and tightened her knees along his flanks, she shifted slightly and he detected her wetness. A moan escaped her lips and he knew she was close to breaking.

Nick had seen her weaken before in intense situations like this and once, he was almost able to break her iron will and seduce her. For a brief moment, he wondered if he could ever succeed in taming this woman and bring her to heel. She interrupted his fantasy seconds later.

"Mmmm, isn't this nice?" Leaning forward she added, "I fucking own you right now and I'm no longer the soft little slut who desperately wanted your cock. Open your mouth wide and don't fight it."

"Jen, please let me have you. Let me make love to you the way you need it. Give in."

As he spoke, she brought his efforts to a close by shoving a slender metal bar crossways into his mouth, nearly causing him to gag.

"Nick baby, I am truly tempted. Believe me, I am but I can't be the woman you want. We have to do this my way. So in case you've forgotten, it's Mistress Jen. I'm going to add you to my harem of playthings but if it makes you feel better, know that your my favorite."

Nick struggled to speak but gave up.

"You like it? It's a bit for my new Pony Bitch." Running leather straps along both sides of his face from the bit, "Don't fight it. I will win no matter what. Try to relax and breathe normally. I'll give you a moment to adjust."

Nick breathed through his nose and told himself he could weather this situation. Whatever she did, he knew she had feelings for him and wouldn't really hurt him.

"Now, lets practice walking slowly around the living room. Move. Find your gait so you don't injure yourself. Come on, keep moving Pony Bitch. I have ways to motivate you if needed."

Nick did as he was told, clumsily shuffling his legs so as to not stretch his sack too much. He could feel himself being guided by the bit with tugs to the left and right, the path eventually leading back to the flyswatter.

"Nice. Now hand me the swatter and tell me what you think I'm going to do. Be descriptive."

Nick found it almost laughable as he tried to spit out words. "Ur ong ew wat ee."

"Oh that's right. You're mouth is full. One day soon your mouth will be filled with my strap on. And trust me when I say that when that day comes, you will beg for it first and suck it better than even you have been sucked on yourself."

"Now, ponies don't speak, do they? They whinny. From now on, whenever you have my bit in your mouth, your words will come in the form on a whinny. So let me show you what the swatter is for and be sure not to react badly like before."

Nick steeled himself for what was coming but found the swat wasn't super painful. He quickly developed an appreciation for her skilled hand, which never missed the mark. By the time he made it across the room, she had already perfected just how much energy it took in her smacks to keep him moving briskly without being so hurtful that he felt an urge to ball up in defense.

After a couple trips around the room, Nick was growing confident in his new role but Mistress Jen always had a way of sensing this and stripping it from him.

"Very nice Pony Bitch! Now, let me here you whinny. Come on, do it!"

The swats rained down on his tender grapes but when he mistakenly tried moving forward, Mistress Jen harshly yanked on his bit.

"Learn Pony Bitch. It's not time to move. I told you to whinny and I'm going to hurt you until you get it perfect. Now whinny!"

Nick felt absolute humiliation as he practiced his pony noises but what choice did he really have, he thought.

"Much better. Time for some laps. Make sure to spontaneously whinny now and then like a good little pony. I like that."