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Life of a Dominant Futanari Chapter 28: Training the Sissy Dry

So, what type of sissy do you want to make your Sissy? I asked myself while we were sitting in the jacuzzi. Samantha and Crystal were talking about something, as I thought to myself. This was a question that, throughout the conversation, Samantha wondered about. When I asked why she told me that it was important to start with a destination in mind when training slaves, and I raised an eyebrow, but I understood pretty quickly.

“Look, Angela,” Samantha had said, getting my attention, “No matter how ‘Spontanious’ we want our actions to seem sometimes, you plan. You plan almost every action you take for the reaction you want. You need to be ready for changes, though, and to reach a destination. Planning is one of the most important things for Dominant people like us. You don’t need it perse,” Samatha had said as I replayed the moment in my mind, “But you will find that with a planned training not only becomes easier for you, it becomes easier on your slave. You need a destination, Angela; floundering in the dark will only increase training time and confuse the sissy. Same with that skank of yours. I already noticed some mixed signals from her.” Samantha had said, and my thoughts whirred.

I needed to think of what I wanted Tracy and Jake to be. Jake, I was planning on abandoning; that was not even a question in my mind. What I wanted to do with him was more what would destroy the rapist more. Tracy, on the other hand, I was growing warmer too lately. She even had something to say but kept her mouth shut. The blackmail I had on her, though, was much more complete than with Jake. Jake could actually fight back if he were willing to give up his reputation.

That constantly meant that I could only go so far in cornering him. I had thought about this before, and it wouldn’t be the last time. I didn’t know about him because he would consider the point that he would rather lose everything than continue to degrade himself to me. The more he submitted, the more, the farther that line would move, I believe. Sometimes people pass the point of no return without ever knowing that they had done so. This is what I needed to achieve with Jake. Samantha was correct on what I needed to do; Plan.

What was Jake’s future Ideally for me? Was it to find someone to pawn him off too? Whore him out like some cheap skank until I find a buyer? The last thought made me frown. I didn’t want to degrade myself to becoming a pimp. No, I wanted something that was retribution for what he did to me. Samantha was right; I can already think of different ways to train this sissy. One was a sissy maid cleaning and doing chores inside a chastity cage. That meant keeping the fucker around, though.

Though, others might keep him in my sight to see his degradation even further. I could make him keep dating my little Skank Tracy. Make him watch as I fuck his girlfriend. Make him eat the cum out of her pussy while she moans with my cock up her ass. That brought a smile to my face thinking about it. It was a happy thought, but I didn’t want him to forever remain that close to me.

I needed to start thinking in the long term now, I realized. Jake would be in Football practice, and the ‘Early Morning Workouts’ with him would be the only time I could play with him unless on weekends. The afternoons would be filled with team practice. If I tried to invade that time at this point, I risk his future too blatantly; He would resist. I needed to do it right and subtly changing him without his knowledge.

A plan started to form in my mind. I might not know my final destination at this point, but I was coming up with a plan to begin training him towards whoring him out or giving him away when I am done. I didn’t want to go much farther than that. I wasn’t going to allow myself to come down to his level.

No, I needed to bring myself to a point then I could make a decision either way. I knew I was delaying the decision to the future, but it was all I could do for now. Tracy, on the other hand, would be my skank. She was starting to warm on me, and although I would not consider her a masochist. She was definitely warming up to it.

I brought myself back out of my thoughts. “You know Becky was asking about you this week at the swinger’s party.” Samantha said, “She was somewhat disappointed you didn’t show up; so was Rick.” Samantha finished with a smirk.

I looked down at Crystal, and I noticed her roll her eyes, “Rick is too obsessed with me at the party’s, and honestly, although I would consider his cock big, I am not sure I would care anymore for my girlfriend has begun to stretch me.” Crystal said casually, “I don’t know if you noticed, but I think I cant live with something smaller anymore. I even took out all my other condom boxes. Magnums only in this house now.” There was pride in her tone as Samantha chuckled.

“That sounds like you so much. Although you are settling down is still surprising to me. You were so into the swinger scene and the BDSM scene, Crystal. istanbul travesti Hell, You even planned some of the parties. People will feel your missing presence.” Samantha said, and Crystal scoffed.

“Just because the men at those parties might not satisfy me anymore means I won’t go. I got a girlfriend to bring with me to join the parties as well. She will be a hit at the parties, and we both know it, Samantha.” Crystal replied.

Samantha looked at me and noticed I was now actively following the conversation, “Oh, Your back from your thoughts, Angela.” Samantha said with a smile, “We were just talking about you.”

“I noticed,” I replied easily, “I am interested in the swinger’s parties but more interested in those BDSM scenes you were talking about there.” I finished.

“Ah, Well, The Scene is something you will naturally get into with Crystal, and I am sure she will introduce you to it once she can spare a moment. She really does need to get your clothing done this week though at least one outfit, my dear.” Samantha said, her eyes turning to Crystal with a critical eye.

“You’re right; I want to see you rampaging in Decker’s wife the most.” Crystal said with a savage grin, “I am sick of seeing him brag about his dick size at every party. When he becomes the second place in dick size, I truly wonder how he will react. Plus, I want to see how Evelyn will react to a larger cock. I am sure she just has a huge cock fetish with that swingers mindset.” Crystal finished.

“Oh, You’re so naughty, Crystal,” Samantha said with a chuckle, “You need to keep your girlfriend here on a shorter leash,” Samantha said, turning to me. Her chuckle, though, undercuts the words. “Decker is a pompous ass, though, so I can understand why you want to stick it to him.”

“So, You go to swinger’s parties too, Samantha?” I asked her.

“Yup, Although I usually go for some social play. I like to watch from time to time or tie up one of the wives there for my amusement. The open play, though, is what I like about it. I can go in without a plan in mind and make my choice of partner for the night squeal.” Samantha leaned back, and I think she would have looked perfect sipping some red wine at that moment.

“Honest;y,” I said, slowly tightening my grip on Crystal even as my cock hardened a little, “That sounds like a lot of fun,” I told them. “A party where I can bust a nut in someone’s wife and make the husband watch sounds like a lot of fun. I would love to fuck with this Decker person you are talking about.” My grin turned sadistic with the thought of someone in an open relationship looking at me with jealousy. “It feels weird to tell people this, but the thought of dominating some else’s wife really does it for me.”

“Ah, Crystal, Just found another kink in your girlfriend,” Samantha said with a sly smile followed up with a giggle. “You want to be a bull, it seems. You really would be into the Cuckold and Swingers scene then.” Samantha finished.

Crystal turned up to look at me while I was feeling confused. “Angela, Babe,” Crystal began, “A bull is when someone in a cuckold relationship is the one fucking the wife, usually with a large cock while the husband watches. Maybe with some humiliation or even recorded for the husband to watch later. It might even be with the husband himself recording the session. It ties into many BDSM and dominant plays too. I think that might be one of the reasons you like fucking that Skank. You know she has a boyfriend and that you are cuckolding him without shame.” Crystal finished.

“That is a short version and as with many Kinks. It has many branches and ways it can be explored. But you seem to be a bull just from your offhand comment definitely.” Samantha pitched in after a moment. “There are many ways to explore your sexuality through Anglea, Don’t try to narrow yourself on labels. All those do is pigeonhole you into a corner. Your girlfriend here is a prime example of someone who loves many different kinks. Under a general header, she is just a Masochist, but she can also be many other things. If she were to give herself a label, she would become bored with that label after about five sex sessions.” Samantha finished leaning back.

“I also agree with that,” Crystal said, looking up with a smile, “People are complex, and the need to put a label on yourself is a demerit in my eyes. You are you, and I like you as you are. We can explore all the avenues of sex together,” Crystal had an impish grin, and I suppressed the want to spank that perfect bottom.

Instead, I chuckled, “Don’t get all sappy on me, you two; we are still in the Jacuzzi together.” Samantha said, “Still, Your relationship technically isn’t any of my business but what Crystal said is correct. It is better to learn what the other likes while being together than trying and forcing things through. Though, it seems you two are already warming up to the motion.” Samantha finished.

“I am fine moving more slowly, to be honest. We already are moving quite fast,” I admitted honestly, “Crystal’s travesti istanbul body just does it for me also. I get caught up in that perfect ass ripple from the spanking too. Our relationship is moving quite quickly to the point that lately, I spend more time here than I do at home.”

“Well,” Samantha chimed in when Crystal looked to be about to say something, “I think it is time for us to get out of this jacuzzi. I am starting to get pruney, and I would like to see how that sissy is doing if I am honest.” Samantha finished.

I looked down at the condition of my hands and noticed the same thing, and nodded. “Works for me,” I replied before looking down at Crystal, “Feeling better after that short sex session?” I asked her.

Crystal glared at me, then looked at Samantha, “Look at her. She has the sexual stamina that makes me unable to walk then ask me things like this. Samantha, help me bring her down to a wreak that couldn’t handle possible thrust her hips once more!” Crystal exclaimed in false outrage.

“Nope, That womb wreaker will stretch me, to the point, I won’t feel enjoyment from anyone else. Plus, I am not into large insertions like you have always been.” Samantha replied as she got out of the tub, “Try inviting that Skank and the sissy too,” Samantha followed up, “Maybe the three of you can make her submit.”

“Hmmm, That sounds like it could be fun,” Crystal commented.

“Not happening,” I said, pouring cold water as I started to get out of the Jacuzzi myself. “Those two are still dating each other and don’t know the other is being trained by me,” I told them both without shame. “We can do something like that when I think they are ready to learn they are both slaves to my cock. Plus, I want the sissy little bitch in the other room to hold onto that relationship. I want him to cling to it. Put all his manhood into it. Make him grasp onto it like a lifeline and order Tracy not to break off the relationship. When it reaches that point where the only thing keeping him thinking that he is a man. That is when I will fuck Tracy making her beg and squeal in delight as she gets fucked by my cock. Make her beg for my hard girthy cock as she humiliates him for having such a smaller dick. Get her to make fun of the times when they had sex in their relationship, thinking that she was cumming or whatever. I want to watch that despair, those feelings of inadequacy as the one thing keeping his manhood afloat are dropped under him like a trap door hanging that manliness, forever killing that thread left in him.” I finished getting out of the tub and turned to see Crystal looking at me with pure lust in her eyes.

“Oh, My, God, You make me so fucking horny,” Crystal said as she sat back in the tub.

“That is…” Samantha said slowly, looking at me astonished. “Sadistic as fuck, I purely love it.” She continued slowly, “I have the urge to masturbate just thinking about that scene. The rich emotions, the steady drop; The emotional turmoil; Everything about it is purely amazing. The sissy would have his entire world shattered with one mind-blowing fuck as his girlfriend is Cuckolded right in front of him. The woman also had been a part of talking him into the place he currently is in, from my understanding. It, It, Record it.” Samantha finished.

“I plan on it,” I told her simply with a sadistic grin.

“No, I mean if you sell that recording, I guarantee I could get some perverted clients who would love it. Seriously love it.” Samantha exclaimed. “The scene you just painted right now, I want to hire you again just for that. I can almost see the despair and the fuck in front of me. I want to see it so bad now!” Samantha looked at me with great interest now. No, It wasn’t interested; it was something more along the lines of respect. It was something I hadn’t noticed in her looks at me before.

“I told you, Samantha; She has that sadistic touch that surprises you at random times. She is an amateur, but she can come up with amazing scenes.” Crystal exclaimed, now getting out of the tub.

I helped her to stand outside as her knees were still a little shaky. “I have to agree,” Samantha replied, “I think that I might even be happier than before about picking you to be the next Mistress.”

“Thanks,” I said as I helped Crystal Dry off, “It has been one of the things I have been planning since I made skank, well, my skank. It was one of the reasons I started to train her in the first place. The main one, though, was that she fucking helped plan my rape,” My voice grew dark as I said that, my anger returning.

“Hey, you’re using too much strength,” Crystal noted, and I realized that I was still drying her off with a towel. I was rubbing her ass a little too hard as I felt that anger. My movements softened, and Crystal sighed, “Look at this; she even takes care of me after using me,” Crystal noted with a smile. “She is the complete package!” Crystal finally happily exclaimed.

I rolled my eyes but brought myself back up to my full height and made sure to thoroughly istanbul travestileri dry out my girlfriend’s hair making it a mess. Once Crystal realized what I was doing, the damage was already done, and her hair looked like a mess. It also gave her a wild look, but her stare showed her displeasure.

“You messed up my hair,” Crystal said with puffed cheeks. I smirked and brought my lips to hers.

“Yup,” I replied after the quick peck, then ignored her outrage. I grabbed another towel and made sure I was dry myself, although I kept my hair in better shape with a smirk.

“I am looking forward to seeing the condition of that sissy after a couple of hours in that chair,” Samantha said, changing the conversation as she got into her clothes. “He was looking pretty bad after your sex tirades earlier. I wonder what would happen if you had your way with him now.” Samantha noted, and I smirked.

“I was thinking the same thing,” I told Samantha, my grin turning sadistic. “I was looking forward to finding out as well. Want to be the Camerawoman?” I asked her.

“I think you will have two of us to do that today,” Crystal said as she slipped on a robe over her shoulders, her knees still shaking.

“That works for me, and I think the sissy today is definitely going to have problems walking back into that cliche house,” I said with a smirk as I decided to remain unclothed. Samantha, on the other hand, returned to the clothes she was wearing before.

“I really am looking forward to this,” Samantha said, “It has been a while since I got to be a part of training a sissy. They are not very common, and forced feminization can be quite risky sometimes.” Samantha finished, “You have good blackmail and reason to be doing it. I look forward to him being broken in.”

Samanthas grin matched my own smile, and the two women joined me as I stepped back out into the basement. The sounds of moans filled the room we entered. It suddenly increased in volume as the voice echoing in the basement suddenly increased in volume. It was a desperate moan, and it seemed to beg as the Sissy threw his head back and forth as another orgasm ripped through his body. His arms strained against the restraints as we walked up. I smirked as I noticed no more sperm came out of his cock.

Samantha’s eyes turned to see mine as I turned to see hers. Our smiles grew as we watched the sissy come down from a dry orgasm in the black world that he was in. With the blindfold and the earplugs, the only thing he could sense with his nose and his body. That nose brought in the smell of semen, urine, and female ejaculate. The body brought in an overwhelming level of pleasure constantly to make up for the missing senses, though, and his moan tapered off. His orgasm must have finished, and I decided I would start now.

I crouched down, and I signaled Crystal to remove the blindfold. Crystal nodded and made way behind him as I squatted in a pool of sissy cummies and urine. I didn’t care about that, though, as I found the prostate massager that was firmly up the sissy’s ass. The sissy moaned this time in confusion as that blindfold was ripped off of his eyes, and the light of the basement temporarily blinded him.

I didn’t care, though, and I pulled that prostate massager quickly. Jake moaned loudly with the sudden change around his ass, and I felt my cock hardening in anticipation. I smirked, and I pressed the tip of my half-hard cock that was rapidly reaching full mast. The sissy Jake seemed to have noticed what was happening as the tip of my cock entered his asshole that was gaping from the sudden exit.

His moan was begging for mercy, I knew–the look of shock and despair and fear of the unknown colored his expression. My uncaring eyes looked back into that expression, and my hips moved forward under the chair, penetrating his gaping asshole. The Groan and moan echoed into the room as Fresh pleasure filled my mind. The sissy’s ass wasn’t really tight like it usually was. It was undoubtedly because his muscles were tired. That didn’t matter, though, as the new type of pleasure filled me. It wasn’t as pleasurable as a Tight hole that firmly gripped my cock, but it was amazing in its own right. I pushed myself deep without regard for the sissy either as he moaned even louder as I passed that prostate that had been massaged for hours. That was then coupled with the fact that Crystal and Samantha found the vibrates and started to change their settings.

The new changes came too fast for the sissy. His hole started to tighten up, making me moan suddenly. That tightness, though, quickly turned into spasming as the sissy started to strain against the bindings holding him. Nothing came from his little clit, though, as he cried out. My cock never stopped moving, and I pressed my hips against the chair in a hard position to maintain. To my delight, however, I realized what a good workout I could get from this position, and I smiled wickedly.

My hips started to trust up before pulling back as far as I could go before thrusting up. The moans and groans from the sissy as he rapidly started to spasm on my cock continued. His cries were like music to my ears as I made him cum over and over on my cock. His pleas for anything dying in that gag that cut all communication to minimalist moans and groans.

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