The Making of a Man Ch. 04

He wore himself out making lap after lap in the room, his body sweaty from all the labor. His throat was becoming hoarse as he was forced to whinny in response to her questions and comments. His mouth was aching from the bit and his knees were on fire from too much crawling. Worst of all, he worried that his nuts were swollen to the size of coconuts from that nasty flyswatter.

Seeing his breaking point fast approaching, she dismounted her exhausted steed and tied the leads off on a nearby kitchen chair back.

"Don't even think about removing your bit, bitch or I'll make you pay dearly."

He slowly recovered as he saw her get dressed and put her shoes back on.

"Good boy. Had you disobeyed, I was going to give you fifty swats. You may remove the bit now but stay where you are. Time to show you another lovely little feature of the Humbler."

Mistress Jen forced one of his arms back and fastened his wrist to the strap along side the Humbler. As she fastened the other wrist, Nick found himself face down with his ass sticking up in the air, hands bound to a device that constantly tried to yank off his balls. He struggled to keep his arms alongside his body lest the added weight of his arms pull even harder.

"Imagine if I decided to give you those swats anyway. Is there anything you could do to stop me?"

"No Mistress Jen. I'm completely at your mercy."

"Exactly. That's how it's going to be from now on. I could pulverize your precious nuggets right now and all you could do is scream and cry. Now that we are nearly finished with today's session, it's time for a good boot polishing. Begin."

Nick struggled to lick her left bootie but despite the lousy job he did in the awkward position, she seemed pleased with his work.

"I suppose an explanation is in order. I owe you that much. You haven't done anything to upset me, Nick. In fact, what you are suffering through now is actually helping me in ways you wouldn't understand. But more importantly, I'm going to help you discover who you are. By the time I'm done with you, Rachel won't even recognize you."

"Nick, you know I have feelings for you I've never developed with anyone else and it makes me very uncomfortable. I feel vulnerable to you but I can't seem to walk away either. Keeping you like this, fully subjugated and helpless is the only way I can enjoy you safely."

Nick paused the licking and was about to respond but received another swat on his balls before he could say anything.

"I didn't tell you to stop bitch!"

Jen moved to Nick's other side, shifting her feet so he could begin on the other one. Before he started though, she leaned over and gave him another hard slap as a signal to begin. Nick got the message and did his best to appease her.

"Nick, I'm going to let Rachel do some of the explaining but you are going to be spending more time with me from now on. I plan to use your wonderful mouth often and if you please me, I might even ride your cock as well. All for my needs of course. You won't be cumming in my presence very often. If ever. I want to keep you delirious with desire so you'll follow my every command without thought."

Rachel came home as Mistress Jen was laying out her expectations. Nick tried to turn his head to see her but received yet another slap on the testes, this one sharper than the others. He cried out in pain this time but wisely controlled his physical reactions.

Sharply, Jen scolded, "I have not released you from your task. Lick it bitch!"

Rachel took in the whole scene of Jen triumphantly towering over Nick's battered and bound body as he licked at her boot like a broken man.

Rachel considered for a moment what she hoped they could accomplish with all this. The week before, Jen informed her of her weakness for Nick and during subsequent conversations, they devised a plan whereby Jen would reestablish her own control by training Nick as a submissive.

In the end, Nick would be returned to her but he would be sissified to some degree. Rachel knew her desires were getting out of hand but she relished the idea that she could keep Nick kneeling at her feet no matter what she did to him. The thought of him licking her clean after being ravished by another man was absolutely intoxicating.

She knew she felt love for him and didn't want to ever see him hurt but she convinced herself that he needed her and this was a way of her exploring a new lifestyle while meeting his need to remain with her. She told herself that he'd grow to enjoy it if Jen trained him right.

It was only recently, she recalled, that she and Nick decided to make their relationship exclusive but even then, she had doubts about whether that was what she really wanted. She knew she allowed herself to give in to what he wanted, without considering how she felt about her own needs. This way was for the best, she decided. For all of them.

Coming out of her rumination, she declared, "Oh, it is so nice to see you two settling your differences like this."

She walked over and tenderly caressed Nick's reddened sack causing him to groan in relief.

"So this is the Humbler you told me about? I think it's amazing. You have to show me where to get one of my own."

"You know I will, Rachel. Every strong woman should own one. Your timing is perfect. I was just about to finish. Why don't I leave him like this for your conversation? I can get it from you later."

"Well if Nick is going to be coming over every weekend, he can bring it next time you meet."

"That works. Nick, with the start of the new school year just a week away, we will have to meet on the weekends. I'll be texting you from now on to set up our weekly appointments. I may give you extra instructions now and then and I expect you to follow them to the letter."

Gathering her belongings, "In fact Nick, I want you to pick up a dildo today and practice sucking on it. I'll text you the address of the store I want you to get it from. I have a friend there who will ensure you get a good one for our needs. Once you have it, I expect you to practice often. At some point down the road, I will allow you the privilege of blowing me and I expect nothing less than excellence when you do it."

Before Nick could say anything in response, the ladies started saying their farewells and Rachel saw Jen to the door.

Returning, Rachel said, "Now wasn't that nice of her to visit?"

"Mistress Rachel, please allow me an opportunity to explain things. I don't want to keep anything from you. I couldn't stand it if you were upset with me. And don't send me away. As much as I like Jen, I want to be with you instead."

She ran her fingers through his hair and said, "I'm not upset at all. I know far more about your escapades than you think. We've orchestrated your entire sex life over these past few months. And that includes Elyse. Yes, I know every tiny detail. We've been friends since the start. As far as my sending you away, it has nothing to do with anything you've done."

"Don't respond yet, Nick. Just take it all in while I free you."

Nick was physically relieved to finally be freed but as Rachel motioned him to the couch, he had an ominous feeling that something worse was coming.

"Nick, I do love you and I want our relationship to flourish but I wanted to talk more about what we expect from each other."

Dropping the Mistress title for what was becoming a serious conversation, Nick responded, "Rachel, I love you. I have since that day in your bedroom. Why do I get the feeling your telling me it's over for good?"

"It's not over for good but I do want us to take a break. This whole past week, I've been constantly thinking about this new lifestyle. Thinking about us and how you fit into my changing sexual appetites. I know I want you around and I really do love you but I want to slow things down until I figure it all out. I'm turning you over to Jen and we won't see each other for a long while."

"Rachel, I just want to be with you. That's all that matters to me. If you'd tell me what you want from me, I'll adjust to your needs. Just don't send me away."

"Baby, I love that you want to please me. You always have and I'm certain you will continue to do so someday but I've made up my mind. Jen is going to have her fun with you for a few months and train you as her submissive. It's not forever. Go with it and when she's done with you, we can talk about how you fit into my life. By then, I'll know exactly what I want from you."

Nick felt horrible. He had prayed it was all some kind of game but she seemed so serious. His only hope, he thought, was to completely go along with it all and wait for Rachel to take him back when she was ready. He had no idea what sort of terms she might place on him at that point but he knew he loved her and wanted to have her in his life, whatever role he might be forced to play.

Nick defeatedly asked, "Rachel, I'm a little freaked out by this whole dildo thing. Will you go with me to the store? And would you teach me how to do what Jen wants?"

"What Jen wants is for you to learn how to give her a blowjob. You need to learn to suck cock. The first lesson here is to get comfortable saying that. If you struggle to say the words, you're going to struggle mentally with the act itself."

"Rachel, will you teach me how to suck cock so I can please Mistress Jen with a good blowjob?"

"Much better. My answer is no. There is another woman in your life who might help you become a good cocksucker though."

"Would it be okay if I ask Mistress Elyse to teach me this skill?"

"That's fine but as I understand it, she isn't actually a mistress of yours anymore, is she? In fact, you're only mistress now is Jen."

Looking down, he said, "I understand."

"I would never have seduced you last May if it weren't for plans set into motion by Elyse and for that, I'm grateful to her. In fact, if it weren't for her, you'd still be a virgin eventually finding yourself in a boring and sexless marraige someday. You owe her more than anyone."

"Yes, you're right."

"You may ask her help but it's up to her if she wants to do it. And I'll let her know that she may use you in any way she likes from now on. You will never seek out pleasure from her but if she wants pleasure from you, you won't ever refuse her. Clear?"

"Thank you. If Elyse does want sex from me, am I allowed to cum?"

"You are a greedy little whore, aren't you? You are absolutely forbidden from cumming, period. Even if Elyse wants you to. Your jizz belongs to Mistress Jen now. No jerking off either. I know Jen intends to withhold your orgasms for extended periods of time. Denial is the best way to keep you hungry. So hungry you'll do anything. Don't forget we all talk regularly. No cumming without Jen's permission."

Rachel dismissed Nick shortly thereafter, giving him the Humbler to return to Jen and reminding him that he had some shopping to do.

Part two - A new friendship

Nick wasn't sure how to start with Elyse so he decided to reach out to her immediately just to get it over with. He believed she'd agree to help but it was still an awkward and humiliating thing to ask a woman. He sent a text asking if he could come by to ask a favor and was happy when she replied quickly, telling him she was free now if he wanted to come over.

Elyse was a little surprised by Nick's text. It had only been a week since he last saw her. They had decided to stop seeing each other so that he could focus on building his new relationship with Rachel. She was a little disappointed at the time but they arrived at the decision together and there were no hard feelings whatsoever. In fact, they had fantastic goodbye sex all afternoon and she even allowed him to take charge during their last session. A first for them which she really enjoyed.

Since then, Elyse had thought of their last encounter several times. She knew of the plans concocted between Rachel and Jen and thought they were going about it in all the wrong ways. While she didn't love Nick, she did like him a lot and thought he deserved better than what they had in store for him. She never expected to hear from him again but when he called asking for a favor, she knew right away that she wanted to see him. If for no other reason than to give him some good advice.

While Elyse got ready, waiting for Nick's arrival, she received another surprise when Rachel called. She didn't provide much detail, saying it was Nick's duty to bring up the odd request but she did take a moment to sincerly say how grateful they were to have a friend such as her.

Elyse listened, happily, as Rachel told her that if she agreed to Nick's request, she was free to use him in any way she liked however, she asked that he never be allowed to cum per Jen's instructions. Elyse was always keen at finding meaning from what wasn't being said and in this case, her intuition told her that if she seemed too eager to use Nick sexually, Rachel or Jen might try to keep them separated. Caution dictated she hide the elation she was feeling like a poker player who had just been dealt a winning hand.

"Rachel, I really appreciate the offer but I may not use him much, if at all. Whatever this favor is, I'll do it if I can, of course. And don't worry. I'll let him lick my pussy once in a while before sending him off with blue balls. What are friends for?"

Rachel thanked her and they ended the call. While she waited on Nick, she was mulling over ideas that might help him without revealing too much of Jen and Rachel's plan. She knew if she had enough time, she could eventually open his eyes and undo some of their damage but even if she didn't get enough time, she could at least enjoy a few repeats of their last steamy rendezvous.

Upset as Nick was, he was looking forward to seeing Elyse. She was direct and uncomplicated and seemed to genuinely care about him as a person as much as a lover. He pictured her easily in his mind and doing so conjured a feeling of comfort he often associated with her.

Elyse was in her early forties and quite beautiful, Nick thought. Elyse was the first woman he fantasized about before losing his virginity. She was around 5'7" and had a slim but curvy frame of about 115 pounds. Elyse exercised every day and kept her body trim and defined.

She often wore snug jeans highlighting her firm and perfectly shaped ass. Knowing how much Nick liked boots of every kind, she usually made it a point to wear one type or another for his viewing pleasure. Today, Elyse threw on a form fitting tank top and left off her bra to better display her firm B cup breasts, hoping it would drive him wild as it typically did.

When Nick arrived, she met him at the door with a warm hug followed by a warm and wet kiss.

Nick spoke first, "I know it's only been a week but I already miss you. It's nice to be back here again. The last few months, my life has felt a little out of control. It seems to get more complicated each day."

"Sounds like it. Well, where to begin? By now, they have probably told you everything? And are you mad at me?"

"Jen and Rachel told me earlier. It's been an intense day so far, to say the least. And hell no. I could never be mad at you. You have always been wonderful and I've loved every minute we spent together. You've been a friend and I really have come to trust you. I'm glad they are okay with us being together again. Especially as I go through this, not knowing what's to come."

This admission really tugged at Elyse's heart strings because she knew what Rachel and Jen had planned for him. She knew it stiffled his potential as a man and she felt responsible for setting all these events into motion by ever wanting him in the first place. She found herself trapped between loyalties to friends with competing interests and no matter which side she took, she would be betraying someone she cared about. She only hoped the plan she was still formulating would work out.

"So Nick, I have to say I'm curious about this favor you need. Rachel called on your way over but she wanted you to be the one to tell me."

"Jen came by this morning and had her fun with me while Rachel went off to her mom's for a bit. When Rachel came back, she told me we were taking a break while Jen trained me. When Jen is done, Rachel will decide if she wants me back and what role I will play. I could handle the rough play with Jen but what Rachel said really tore my heart out."

Taking a steadying breath, he continued, "Before Jen left, she instructed me to go to a sex shop and buy a dildo which I will practice sucking on so that when Jen is ready, I can give her a good blowjob. I was hoping you could teach me to do it well. Jen can be very harsh when I disappoint her."

Seeing pain etched in his face, Elyse was close to anger hearing this type of detail. She knew Jen and Rachel planned to soften Nick up, even cuckold him now and then if Rachel chose to bring home another man but learning the particulars showed they were taking him too far. It didn't take much imagination to see where this could lead him and the imagery didn't sit well with her at all.

Elyse made up her mind then and there. She was going to train him to become a real man. His own man who made his own decisions. She brought him to this point months ago when she enlisted Jen and Rachel to prime him for seduction and now it was her responsibility to be his friend, guide and mentor. To get him on the correct path for him.

"Well I must say I'm quite shocked. I will teach you if you like but are you sure this is something you're okay with? We all have limits Nick and it's okay to tell them you don't want to do it."

"I love Rachel and I'm prepared to show her I'll do anything for her."

Elyse silently thought that the attitude he just described was the very root of the problem. By being so blindly submissive, they would never learn nor respect his limits. His love for Rachel and obedience to Jen would be used against him and he'd be trained to become their cuckolded sissy if she didn't find a way to stop it.

"Why don't you start at the beginning and tell me everything in detail. If we are going to be spending time together, maybe I can guide you along the way."

Nick started over and hearing all the fabulous details of Jen's pony play made Elyse moist. She certainly liked that sort of roughness, she just wished they targeted another guy instead.

As he finished the story, Elyse decided that she was going to find a way to clear his mind no matter what she had to do. She wanted him to find the guts to tell them both no, even if they stopped seeing him. If that actually came to pass, she thought, probably the better. Then she'd teach him normal guy skills like how to pick up ladies and bed them. First step was to build his confidence and self esteem.

"Okay Nick. I'm in but there are a couple conditions. First off, when you took charge last week, I found it very thrilling. I'm always the one in charge so what you did was a first for me. I absolutely loved it and I want more. Everytime we're together in fact. When we fuck, you have to make me feel like your own dirty, cock whore. I want you to talk trashy and demeaning too. I know you're used to being submissive to the ladies in your life but can you do that for me?"

Nick seemed conflicted and said, "I loved doing that to you last time and I'm so glad to hear you liked it just as much as I did but Rachel said I'm not allowed to cum anymore."

"I know. You're asking something of me and I'm asking something in return. I'm asking you to be a man. No one ever has to know and it will be our secret. Can you keep this from them forever? Even if it means outright lies? I don't want you holding back. If you're fucking me and want to explode, then I want you to do it. It's time you made decisions for yourself."