The Maing of a Man

(Author's Note - First, a special thanks to Literotica author "Cockhole" for his help.

I have a mental outline of potential future stories branching off this first piece, each developing characters more fully as the overall storyline progresses. Please feel free to message me, privately or publicly, any constructive criticism, opinions, or ideas to incorporate into future stories. Thank you!)

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Nick was fairly young when he and his family moved into the neighborhood. He was remarkably outgoing and mature for his age, particularly around people much older than him. He made friends easily, but he could never relax around girls. From an early age, he began to recognize stronger feelings toward girls and this made him even more afraid and insecure in their presence.

Nick was an industrious and hard working boy. It wasn't long before he discovered that he could earn good money during the week by doing yard work. Soon, he was maintaining half a dozen homes up and down the street, including Mr. and Mrs. Johnson's house.

Dan and Elyse Johnson were an unusual couple for the neighborhood in that they didn't have any children and were somewhat older than most of the other adults. Dan was some sort of independent contractor for the military and his job kept him away most of the time. When Dan was home, Nick found him to be a very friendly guy.

Elyse, on the other hand, was quite cold and distant. Although she was the person Nick had to interact with to get paid, she never loosened up like other adults he came to know so he just assumed she didn't like him for some reason. She was undeniably beautiful though. Elyse was on the taller side but lean and trim. She had long, straight, dark hair, perky, b cup sized breasts, and pouty, full lips that drove Nick wild.

Nick decided that he didn't care much for Elyse as a person, but he couldn't deny his attraction toward her. Nick recalled Dan commenting once that he was planning Elyse's fortieth birthday party but if she was forty, Nick thought, she sure didn't look it.

As Nick got older, he found his attraction to Elyse also grew even though she still paid him very little attention. Nick looked for opportunities to be in her presence just so he could stare at her, but she always seemed to notice this and kept her distance.

This wouldn't be so bad, but he was old enough now to know about the joys a woman could bring a man. To make matters worse, his friends were learning about girls and sharing all they learned from their own firsthand experiences. A couple years back, he found his dad's stash of girly magazines and spent plenty of time studying the beautiful pictures inside. The pictures were instrumental in helping him understand the female form but they always left him longing for Elyse.

In time, Elyse and Dan separated but Elyse remained in the house. She continued paying Nick to do the yard work but still remained chilly toward him. Around the age of eighteen, when Nick's interest in girls was hitting an all time high, Elyse started treating him nicer and he couldn't figure out why.

Elyse watched through the kitchen window one Saturday morning, drinking her coffee, as Nick dutifully cut the grass out back. He was a trim, handsome boy but far too shy for her liking. He had been doing their yard for years and she knew he recently turned eighteen and was about to graduate high school.

For years, she paid him no mind but as his body developed more, she started thinking Nick might become a real catch someday for the right girl. Nick was extremely sweet, and Elyse sensed that he had a naturally submissive side. Elyse noticed the way Nick looked at her over the years, even more so of late, and it was obvious to her that he was completely enamored with her. She began to like the thought of someone like Nick servicing her.

After Dan left three years ago, Elyse immediately started exploring her newfound freedom. She took lover after lover in the first few months and discovered that she relished being in dominant roles most of all. Before long, Elyse had several submissive young men who were always a phone call away to fill her needs. No longer was she playing the role of a dominant woman from time to time in the bedroom. Now she could be her naturally dominant self at all times.

As she sipped her coffee studying Nick, she reminisced about a young man named Jack shortly after her divorce. Jack seemed like the perfect little stud to satisfy all her needs. There was no love of course but she did love the way he tried so hard to keep her satisfied. Sadly though, Jack started to change and one day, he texted her that he had met someone and needed to move on. It really burned her up that he didn't have the guts to meet her in person to say goodbye after all they shared together.

Elyse dismissed her thoughts of Jack and imagined the kind of young man Nick would be as he grew up, but her thoughts shifted darker, to her domineering side, picturing the kind of man he could be with the right training. The thought quickly made her pussy moisten but she tempered those desires, reminding herself that he wasn't ready yet and needed some basic training first. A plan started to formulate in her dirty little mind.

The following day, Elyse met with one of her closest friends, Jen, to see if her plan had any merit. Jen was known to Nick only as Ms. Blizen but Nick certainly did not know that Ms. Blizen and Elyse were close friends. To Nick, Ms. Blizen was simply his English teacher at school. Had he known of their friendship, Elyse's plan would need a seriously different approach.

"You're certain Nick knows nothing about our friendship?" Elyse asked as they enjoyed breakfast together.

"Not possible. I don't get very close to male students for obvious reasons. They all sit and drool at me every day. I enjoy the attention, of course, but I don't have time for immature boys."

Jen continued, "I still don't understand why Nick is so intriguing to you, Elyse. He's the shyest boy I've ever seen around girls. I'm not so sure he can come out of that, at least not anytime soon. You've had some high-quality young men over the past couple of years. Do you really want some boy that's going to cream his pants in the first thirty seconds and run home to his mommy? I looked at his file. He just turned eighteen and I'd bet money he has still never even kissed a girl."

Elyse considered her friends advice for a moment before responding.

"You may be right, Jen, but there is something a little different about him. Not sure what that is just yet but I have this feeling that he has mountains of untapped potential and if he could be trained up a bit before he gets too set in his ways, he could be the hot little piece of cock I've been looking for since Jack moved on. The guys I have at my disposal now are enjoyable enough, but I want someone a little more naïve. Someone I can easily control.

Elyse paused to sip her coffee, "For the past couple years, I've noticed Nick staring at me. He's interested but he's incapable of acting on it. I think if I do it right, he will fully surrender to me and he'll become quite a play toy with little training. Besides, how many times have we both joked that the thrill of the hunt can sometimes be more fun than the kill itself?"

"Elyse, your friendship has meant so much to me over the years. Until the divorce last year, I had no idea how good sex could be. You taught me how to take charge of my sexuality and you've even been a role model for me as I've built up my harem of young men. I can't see ever settling down again. Not when I can call any one of my eager boys to come and service me at a moment's notice."

Elyse chuckled at that, reflecting on just how far Jen had come. Hell, she was becoming a real sexual monster, chewing up young men and rotating new ones in regularly if any failed to meet to her high expectations.

"You know Jen, if I do it right, I'll have Nick wrapped around my finger for years to come. You and the other ladies like switching boys back and forth and that can be fun but I would really prefer just one main young man who knows every inch of my body and exactly what I like. I'd still share though, and you'll always have free access to him if you like. In fact, if he turns out like Jack, I'd like show him off once in a while."

Jen laughed at that. "Okay, count me in. I predict you will get bored with him though. You think you want one guy but I know you better. You'll enjoy him for a few months and decide you want something different. Some new challenge. Whatever the reason though, can I have him when you get bored?"

"Didn't you just tell me he wasn't worth the effort? What use would you have for him? Boot licker?"

"Well, there's that! No, I figure he's not worth the effort at the moment but maybe once you get through with him, he will be. He's actually a good person, really cute, and I do think he has a very submissive side. I admit, I see him in my class each day and more than once, I've thought about how much fun it would be to utterly dominate him."

"You should know better than to even ask, Jen. I don't get attached to men anymore than you do. Once he's mine, you can play with him anytime you like. I'd only ask that you not be overly rough with him. You can be so hard on your toys. But yes, if I do get bored, I will bring him to you, leash in hand, and you can have him, no holds barred. Poor Nick had better hope I never get bored!"

Both of the ladies got a good laugh at that before Jen started in.

"Unlike the boys I teach at school, I am very close to the girls. They don't know the details of my personal life other than that I'm a complete freak and love to use men for my needs. Because of that, they come to me for a lot for advice on love and relationships, but far more often on sexual matters since I've made no secret about my skill set."

Jen leaned forward in her chair as if she didn't want others to overhear, despite their being alone.

"It just happens that there are two senior girls at school, one in Nick's class, that have crushes on him. I know this because they have each approached me and asked my advice on how to get his attention. In both conversations, I advised them to look elsewhere because I thought Nick was simply too shy for them. They are both more experienced and would probably get frustrated when he failed to accept their advances. I might be able to make something happen here."

"That might be perfect Jen. I was hoping you'd find someway to encourage Nick to find a girl, but this is even better. Do you think you could persuade one of them to make a move on him?"

"Sure. They might even be successful in dragging him to second or third base but what is your plan after that?"

"If you can help me get him past his crippling shyness, I should be able to do the rest on my own. He stares at me every chance he can. Time I give him something to really stare at!"

Elyse and Jen spent the remainder of the afternoon fine tuning their plan. Jen was getting excited at how things might turn out. If nothing else, Jen thought, the whole play that was about to unfold would probably be very entertaining to see up close.

Elyse explained that she only needed Nick to overcome his shyness with girls and be confident in who he was as a blossoming young man. She liked being dominant with men, but she did not like weak ones who groveled too much or shot their loads with the slightest stimulation. She needed Nick to have strength and confidence in her bedroom so that he could fuck her for hours yet have the appropriate submissiveness to always put her needs before his own.

Elyse told Jen that part of her plan involved trying to tease Nick mercilessly for the remainder of the school year so that when the time came to claim him as her property, he'd surrender to her without the slightest resistance.

Jen figured that being on the inside and having access to dozens of pretty senior girls, Nick's training was sure to be a success. Jen resolved in her mind that she would ensure Nick was ready when Elyse was ready to take him. It was the least she could do for her good friend.

Jen didn't share it with Elyse then, but she was also thinking over a far more aggressive alteration to the plan which she would attempt first and if it worked, it could pay off hugely for both Nick and Elyse. She just wasn't sure if she could pull it off or not. What Jen didn't share was the fact that one of the older girls in Nick's class, Rachel, happened to have a very slutty reputation and for that reason, she and Jen got on really well. Jen considered how she might be able to persuade Rachel into seducing Nick without openly asking her student to do such a thing.

Jen thought about sharing this idea with Elyse but she didn't want to get her hopes up until she had a chance to speak with Rachel first to feel her out.

Part two - Setting the Stage

During the next week, Jen made it a point to try and get Rachel in her class alone at lunch so she could set Nick's real education into motion.

Rachel liked Ms. Blizen and sought her out often for sexual advice on advanced techniques like having safe anal sex or getting a guy to perform cunnilingus to her satisfaction. Rachel believed that Ms. Blizen understood her and seemed to hold no judgment. In fact, Rachel got the impression that Ms. Blizen eagerly approved of her behavior.

Although Rachel had never shown any interest in Nick, Jen knew what a dirty young woman Rachel was and even admired that quality in her, perhaps because she saw so much of herself in Rachel. Rachel had confided dozens of her sexual escapades to her over the last year and Jen appreciated the detail in every story. Jen had even joked to Rachel more than once that she should consider a career in writing romance novels and to her surprise, Rachel liked the idea stating that her mind was filled with ideas for many such stories.

With regard to Jen's plans to get Nick laid, it helped a great deal that Rachel was one of those kids who got held back a year at a young age so she was unusually well developed both physically and emotionally.

Jen was secure in her own appearance but like so many women, she couldn't help but compare herself to Rachel. For a nineteen year old young woman, Rachel was built right and attracted lewd stares even from the male teachers at the school. Rachel was about 5'7" and 115 pounds of beautiful curves. In her conversations with Rachel, she knew that Rachel wore a 36d bra size and figured a virgin like Nick would be completely hypnotized if he saw them set free. Rachel was a cheerleader and her regular practice routines had given her a firm, round ass along with sculpted legs and arms.

Rachel had long, black, hair which she usually tied in a pony and her face was quite beautiful as well so it wasn't hard for Jen to imagine Nick comparing Rachel to the women he no doubt jacked off to in Playboy magazines. Jen was certain that Rachel would be the right person to seduce Nick.

Normally, Jen liked to leave her class open at lunch so students could ask for help with their school work but in reality, only the girls spent time in there and the only educational talk taking place involved sex in some manner or another, with their teacher weighing in as needed or when requested. Today was a bit unusual with Jen specifically asking to meet Rachel in private and the door stayed closed so they would not be disturbed.

Now in the classroom alone, they spent a moment catching up. Rachel always had good stories to share but Jen also didn't want Rachel to be nervous in any way since it was out of the ordinary to ask to speak with her so privately. The riskiest part of this plan involved asking Rachel to help by taking Nick's virginity. The approach needed to be just right so that Rachel volunteered as opposed to being openly asked.

"Rachel, I wanted to ask your help in something of a personal matter and I hope you don't take offense to it in any way. In fact, if you object to it in the least, please feel free to refuse. There would be no hard feelings."

"Ms. Blizen, you've been almost like a sister to me. If I can help, I gladly will." Rachel's curiosity was piqued.

"Do you know Nick from your sixth period class?"

"Yeah. He's been in other classes of mine the past couple years but this semester, we have only your English class together. Super nice guy. Cute too, but insanely introverted."

"Exactly, Rachel." Jen knew she had to be careful with the crafting of this next part since it was completely untrue.

"I don't usually reveal what I know about students in their outside lives but in his case, I know his parents well and they are a bit concerned about his extreme shyness with girls. The poor guy is just turned eighteen and he's never even kissed a girl. I know this is a bizarre request, but would you be willing to help him overcome this? I would be eternally grateful to you."

Rachel smiled broadly, "So you want me to pop his cherry? That could be fun. I've never had a virgin before!"

"Oh my god!" laughing as convincingly as she could, "Rachel you are so bold! I was just hoping you could hold his hand or give him his first kiss but if you want to take it further, it would probably do him a world of good. Only go as far as you feel comfortable with."

In truth, Jen was secretly hoping that 'as far as you feel comfortable with' meant that Rachel would fuck Nick senseless and turn him inside out. That was why she sought Rachel out over other possible girls who might help. She just couldn't risk such an open, even shocking request like that.

What Jen really wanted was to order up a list of sexual services for Nick as she might do with her car being serviced at the dealership. But she knew she needed to just have faith in Rachel to bring him into manhood in a fantastically memorable way without Jen knowing too many details beforehand. If Rachel chose to volunteer the story afterward, she would certainly enjoy hearing it!

In all likelihood, Rachel would want to boast to her of her conquest like she did with stories of other boys. Rachel confided much to Jen of her exploits and she was good at rehashing her stories in a way that always left Jen hot and bothered. Jen liked that about Rachel and at times, Jen shared a few stories of her conquests as well. She just had to filter her own stories slightly since they were far more intense than Rachel was used to.

Jen even imagined that once Rachel left school, they might very well stay in touch. Rachel was highly sexual like her, she thought, and it would be fun to tag team some guy together, bringing him under submission like a wild horse being tamed for service. The two of them together could become the stuff of legend at Jen's sex club but Jen had to keep those kinds of thoughts in check for now.

Part three - A Virgin No More

Jen noticed Rachel trying to engage Nick before, during, and after class each day and she admired Rachel's tenacity. Rachel had been dressing very skimpily the past week, sitting next to Nick during class and trying to make small talk. She had been wearing short, tight T-shirts and tank tops accentuating her ample tits and showing off her rock-hard stomach. She made it a regular habit to yawn and stretch when he was turned her way so he could take it all in.

From Jen's vantage point at the front of the class looking back, she noticed more than once Nick checking Rachel's body out. He obviously liked what he saw but if there was ever any doubt for Jen, it was all but gone on day two when Jen noticed Nick trying to hide a huge erection with his backpack as he left class that day.

One particular Thursday, Jen noticed Rachel leaning into Nick during class telling him something and conspicuously placing her hand on his arm as she made small talk. The flirty move had Nick looking even more uncomfortable than normal and Jen had a feeling Rachel was moving in for the kill.