The Club of Fools Ch. 02

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Jason is used as a male prostitute, but dressed as a woman.
9.7k words
4.5
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Part 2 of the 10 part series

Updated 06/07/2023
Created 03/20/2015
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sublocked
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Author's Notes:

(1) Before someone goes off half-baked about this submission, please read chapter one. I like to tell a story that has erotica in it, in contrast to erotica with a faint storyline in it.

(2) This is FICTION.

(3) There are bizarre scenes herein, sexual to some, perhaps horrifying to others.

(4) Please be aware that Victoria's activities are illegal. She is a type of female psychopath.

(5) And the wax head idea? Do NOT try this at home as it would be very dangerous.

(6) Many will question the possibility of this plot ever happening in real life. But just ask the question: COULD it happen? And the answer is: yes it could. Having said that, that's all I need to tell a story.

(7) Finally, always remember that truth is stranger than fiction.

*****

Jason waited on Victoria's now familiar front doorstep after ringing her doorbell. The morning rain was sideways in the cutting October wind and he strained to lean away from the drenching onslaught, causing him to have his face closer to the door than he wanted when it opened. He jumped back in a start when it did open.

Victoria greeted him as if he was a party guest, dressed in simple black Lululemon Capri tights and a form-fitting red top which barely covered her generous breasts. Those breasts had also bounced with a startled response to Jason being so close to the door. Her hair was still wet, probably from a shower, and she had clearly not had the time or the inclination to tend to its drying and styling. But with her, any state of undoing was still an attractive state.

"Come in Jason! Good to see you," she exclaimed, "My God, did you ever see such rain for October? The leaves are dropping like rain themselves."

She was talking as if nothing distasteful had happened between them, and Jason just stared at her bleakly as he entered the front hallway. He shrugged his shoulders and shook himself like a dog, shivering as she shut the door behind him.

"Let me take your coat. I know you've booked the day off, so you might as well relax."

Jason glared at her as if she had three heads and said, "How did you know I booked the day off?" She was about to answer when he continued, "Oh never mind; maybe I don't want to know. Uh, I'm not staying. Here's what you wanted." And he handed her the envelope with the money. This is when it got strange. She said sternly, but with an incongruous smile, "Of course you're staying. Take all your clothes off please. NOW."

Jason tilted his and expressed disbelief, "What? No. I said I was leaving. Fuck you! Here's your money."

"Jason, why are you talking like that?" she said sweetly but now with no accompanying smile, "Please come in and stay for a bit. You really, really should stay. Please. I have something for you. We can maybe have some coffee, and later on some wine...you know, make a day of it. This is part of the scene that you wanted isn't it?"

"What scene?" he asked, "Jesus, you're fucking nuts!"

"Ah, good acting, my little stud! Now come in and make yourself at home. Clothes off please," she said.

"Jesus, I'm gonna fucking kill you if I get the chance," he said, "Shit!" Then he started pulling his clothes off until he was standing in front of her with just his tightie-whities on. She wiggled her finger indicating that those too had to hit the floor. The scene got weirder still, as when he dropped his shorts, he stood there, clearly aroused and ready. Why and for what, he had no idea.

Victoria walked around him a couple of times inspecting him, feeling his hair, looking into his ears; then she searched his clothing on the floor, finding his cell phone, and putting it in her purse. "Okay, you're clear," she said, "Hang your clothes in the closet and come with me."

Now Jason understood. She thought he might be wired for sound. Why hadn't he thought of that, he wondered? Mind you, it would not have worked, would it? Nonetheless, he decided to do that sometime in the future, as she would inevitably relax and he could trap her in her blackmail. This idea was soon quashed by her statement, "Whenever I summon you from now on, the first thing you do when you enter is to get your clothes off. Is that clear?"

"Oh, for Christ's sake!" he said, exasperated, "Really?"

"Yes. Really. And I do NOT like your attitude right now! Just so you'll know, your file is on what I would call "trial probation" right now. Until your routine is established, one false move and there will be an instant trigger response from Suzie that you'll regret immensely. Now, put these panties on and cover up your thingy please; you're gross. Go on; I know you like wearing panties."

Jason couldn't help it; he not only remained aroused, his arousal increased so that his breathing was now almost as rapid as his heart beat. It was intensely embarrassing to be exposed both mentally and physically like this. When he pulled the panties up, a wet spot appeared almost instantly at the front at the end of his bulge.

"Well, isn't that sweet?" Victoria said with more than a hint of sarcasm, "Sit down while we go through a few things. You've made me grumpy."

He looked around and decided to sit on the sofa so that he was facing the kitchen. He sat there nervously in the living room, a room straight out of the sixties, with a half-wall separating it from a dinette adjacent to the kitchen. But it was an odd combination of sixties layout and 21st century furnishings and decorations. She was a golfer, and there were numerous golf trophies on one shelf. The walls were graced with an array of black and white sketches of nudes, all of them women. He had not really spent time here before; he had always been led to her dungeon in the basement. It felt oddly more intimate. Jason was silent, but his inner thoughts echoed around in his head like banging drums, the misery of shame, embarrassment and above all the carnal betrayal of his arousal, the tent in his panties.

Flashes of memory arced in his brain like fragmented dreams as he sat there. Some other woman, his hands...they were tied..., a man...there was something pushed into his ass. He shook his head and shivered. "How did you drug me?" he asked, seemingly out of the blue, "What were the drugs?"

"As I said, a former nurse's secret. You don't need to know."

Jason shook his head slowly and said, "Everything you're doing here is illegal. You could go to jail for a very long time you know, and you will. I'll figure out a way."

"Well, Mr. Lawyer, as a matter of fact I do know that. That's why I have a system like I have, to ensure that doesn't happen. Now, if you don't mind, let me explain your new situation to you, Mr. pantie boy." She sat on the love seat opposite him and leaned forward with her elbows on her knees and her hands together.

"I want you to understand that in addition to the $1,000 per week, there are other required, umm, "services". I have a club of my own in addition to yours. It's an all-female club and we all share certain, uh, appetites and sexual tendencies that we need to act out on real people, just like you. You're part of that now. Now I want to introduce you to your club kit and then I want to measure you for a bondage corset I need to order for you. All the males have one." She watched him blanch, and then turn red in seconds, a perfect sexual flush of arousal at those words. He was so easy to read.

"Don't try to hide from it; I know you'd like that," she said, smiling. Then she shook her head in disbelief, "Honestly, your fantasies are like "hunter orange" in a green forest!"

Jason put his face in his hands briefly but didn't comment or even try to defend himself. It seemed strangely humiliating to be called a male instead of a man, as if maleness was simply an anatomical description, whereas a man was something more than that, perhaps suggesting virility and dominance.

Now Victoria pulled a black canvas shopping bag from the coffee table. "This is your kit. I'll explain each item."

Jason shook his head in incredulity at the predicament he was in. Seemingly out of context he said, "Who's Suzie?"

Victoria smiled. "Huh? Oh yes, I suppose you don't remember her, do you? She's my wife. And she's the one who did the video of you when you were having your homosexual affair. That was precious, by the way."

Jason thought about those videos and asked, "Precious. Yeah, right. Victoria, that video...the one with the cock in front of my face when my hands were tied...did I, you know, did I...?" He couldn't bring himself to say the words, and yet the unsaid words seemed to materialize out of nothing and hang in the air.

"Ah yes, that was a good one," she answered mischievously, "You'll never know, will you? Well, I shouldn't say that actually; you will find out if our arrangement falls apart. Along with everyone else you know I might add."

Jason sighed in his small but significant defeat, "Yeah, I suppose so." He had to ride this out.

From inside the bag, she pulled out the first item, a large rubber bag of some sort similar to one that his mother used to have filled with ice or warm water for her headaches. A long tube with a squeeze off valve was attached to it. He looked at her, naïve and puzzled.

As if he had asked the question, she answered, "An enema bag. Fill it with warm water and a small amount of soap. Hang it in the shower at neck level and insert that end there in your ass and release the valve to fill yourself up. When the bag is empty and you're full, hold the water inside you for as long as you can and then get out of the shower and expel it into the toilet. Repeat. Do this prior to every visit. I want you clean for gay and bi scenes."

Jason was having incongruous thoughts of both disgust and arousal and he squinted in confusion. He managed a manly, "Oh, for fuck's sake! You know I'm not gay. Why would...?"

She interrupted him, "But the video seems to suggest otherwise doesn't it? Oh, and the tent in your panties. You really are a piece of work, aren't you?"

This rendered him speechless. He was not used to being speechless, and he didn't like it.

She reached into the bag again. This time she pulled out a very heavy stainless steel butt plug which she passed to him. He hefted its weight in his left hand, frowned, and nodded his head up and down as he said, "I see..."

"I think you're starting to get the picture, yes. That gets inserted after your enema. The lubricant is in the bag. Use lots of it. You'll get used to it. Note that it has a small handle so I can work it a bit if I choose. It's amazing what that does to a male when it probes the prostate."

The next item was a red hood made of fairly thick translucent and red-colored latex. There would have been an opening at each eye except for the fact that a set of swimming goggles had been cleverly sealed as one to the hood which would allow clear vision with no compression directly on the victim's eyeballs. The entire hood was a sealed unit and had no air holes at the nose or openings at the ears. In fact, sealed at the mouth was a flexible device similar to a snorkel mouth piece designed to be inserted into the subject's mouth, but filling more of the oral cavity. A short air tube extended from it straight out below the nose.

Victoria said, "This hood is actually for your benefit. This is your default hood. Whenever I have a club function and you are serving us, your identity will not be revealed, provided you do as you're told. Sometimes I also have functions where all of the males are here as well, and each will be wearing a similar hood. You won't know them and they won't know you. I think that would be prudent, don't you? To put it on, turn it inside out; insert the mouth piece and then pull and stretch the rest of it over your head. It's really tight but fairly comfortable. I tried it myself. Put it on so you know how it feels."

Jason's heart was racing wildly as he placed the rubber mouthpiece into his mouth. He was shocked to find that it almost filled it so that he couldn't form words. His cheeks bulged with the filling, but the breathing was easy through the tube as he stretched the hood over his head, adjusting the eyepieces over his eyes. It was surprising how much of his hearing was taken from him. Most of what he could hear was the roar of his own breath going in and out of the tube. He tried to speak but could not.

"As soon as you strip down when you arrive, you'll put this hood on immediately, so I don't have to listen to you or even look at your face. Unless I say otherwise. You can take it off for now."

The smell of rubber stayed with him as he peeled it off his head. That was a "trippy" device, he thought, and indeed, it was something that made his mind flood with erotic sensations of bondage and discipline.

Next she pulled another latex hood out of the bag, a black one which was similar in most respects to the first, except for the obvious color difference. Upon closer inspection, it had an opening at the mouth and therefore had no need for a breathing tube.

"Commonly we like oral sex," Victoria explained, "You will wear this hood when required. Again, discretion is my motto; I won't expose your identity if I ask you to change to this hood. You'll be asked to do it in private. Everything clear so far?"

"Jesus. Yeah I guess so."

"Good. By the way there's no need to call me Jesus; Goddess will suffice if you feel the need to deify me."

She smiled at her joke. He did not.

The last item was a clear plastic device that he had seen images of on websites and had scoffed at its stupidity. It was a ball-trap male chastity device that, when installed, did not allow the wearer to touch his penis in any way. There was a hole at the end to allow cleaning with swabs, and for urine escape. That was it. A small luggage lock or numbered plastic locking tag kept it in place, and theoretically tamperproof.

"Seriously?" he said, "I've seen these on some websites. These are silly. I can get this off so easily."

Victoria smiled. "Physically, that may be so, but not if you want to stay incognito."

"So what!" he scoffed and shrugged, "I could just cut this plastic locking tag off with a pair of scissors."

"Yes. Yes you could. But I don't think you better do that, do you? That tag has a unique number on it. If you arrive here without that device intact as installed today, you know the consequences, don't you? Put it on."

"Today? Now? Come on. You think I'm going to wear this all the time?"

"Until I remove it," she said simply, "Now put it on."

It was a little more complex than he thought, and there were many separate pieces. His erection did not help, but eventually, after much fumbling, he got the ring around his penis and ball sac. With all the effort his penis had now gone limp and he was able to insert it into the tube and attach it to the ring with the numbered plastic tag.

Victoria got up and went to him to confirm that the device was indeed secured. With a pen she wrote down the number of the tag on a scrap of paper. Then she lifted his manhood and clicked the plastic with her fingernail. He felt nothing. But he grew again, or at least he tried to grow. His stubby length pushed against the clear plastic in all directions.

Victoria looked on with pleasure. "Oh this is ideal; you're a grower, not a shower. When you try to get hard, it won't have any place to go, will it? Perfect. All dressed up and no place to go."

Jason batted it around in despair. "Look, uh, this is really stupid, don't you think? Come on! Isn't the blackmail of $1,000 a week enough? What the hell am I supposed to do if I get lucky at a club or something?"

"What do you mean?" she asked, feigning innocence.

"Well," Jason said with barely concealed exasperation, "When I go to the Jasper Club... Well, you know, what if I'm getting on nicely with some chick and, and well, now what am I supposed to do?"

"Well," Victoria said, giggling, "One of two things will happen; you'll go home alone; or you'll cut it off and have sex. The latter will have pretty severe consequences, won't it? Now, pull your panties up and let's have a coffee. Let's just say that I have some control now, I believe." She started to put the bag back down on the coffee table but then she remembered one more thing and, bringing out a piece of paper, she handed it to him and said, "Read this. You'll be required to sign and date this at every visit prior to us using your services."

It was a waiver and it basically stated that (a) he was a prostitute; (b) he understood that he would be treated badly by the group; and (c) that he was okay with that. There was a place for him to sign and date it.

He looked up at her and said flatly, "This isn't a legal document and you can't force me to sign it. It wouldn't hold up in a court of law. In fact, it's ridiculous."

"Say whatever you like, but you WILL sign it. And you'll sign it at EVERY visit. And you know it. Furthermore, once the right (or wrong) people see your collection of videos and see that you performed of your own free will with full participation and mutual enjoyment, what do you think those people will think? Tell me. What would they take from that?"

Cornered again. As a lawyer, he wasn't used to this. Jason was tight lipped, silently brooding and sweating, thinking desperately about how to deal with this. He just seemed to be reacting to her, order by order, always feeling off-balance, and unable to be pre-emptive. For the life of him, he couldn't realistically figure out any way to deal with this other than through the impulse of strangling her.

But (he had a thought) , maybe, just maybe he didn't need to deal with it. He did enjoy the physical acts after all. He liked rough sex, bondage, discipline, all the bizarre stuff. Maybe he could just do as he was told and enjoy the ride. It's just that it was so humiliating to be forced to do these things, and he had no idea what she was going to demand of him. And this was so backwards. He was PAYING a prostitute, but the prostitute was doing what SHE wanted. He had no say in anything. Worse than that, she could ruin him if she chose. It was the coercion he hated, the absolute control of his body and mind.

Then it dawned on him; he was the prostitute here.

He followed her into the kitchen and sat down at the table while she made him a coffee. "Cream and sugar?" she asked.

"Just cream please," he said. He felt like being sarcastic and saying, "Woof, woof" or "bah, bah" as that was how he felt, a powerless puppy or a sheep following the shepherd. There didn't seem to be any way out of this and he wondered what sort of plans she really had for him other than the $1,000 per week income stream. He glanced around the kitchen, self-conscious, sitting there in panties and nothing else, holding his "club kit" on his lap like a purse. The smell of bacon hung in the air, and now coffee. It warmed him as he took a sip, and it made him even more conscious of his lack of clothing. Goose bumps formed on his arms and legs. He shifted in his seat slightly and the chastity cage slipped on the fabric of his panties and made a solid sound as it contacted the chair.

Victoria sat beside him, sideways in her chair, staring at him while she sipped her own coffee. Awkward moments passed. Then she said, "You know, you will enjoy a lot of what we do to you. Some of it (actually a lot of it) you won't enjoy, but that's just the way it is. Anyway, I suggest you just get used to doing as you're told and taking enjoyment from it when you can. It'll be easier for you. We've gotten into the habit of using the males for various get-togethers every week on the weekends, sometimes one night, sometimes three nights in a row. In fact, we have contests to come up with the most bizarre bondage, discipline, or raw humiliation scenarios. We all chip in a bottle of wine and then vote for the best scene (we can't vote for our own idea) ...winner takes all. Puts all you studs in your place; that's for sure. But at least you're all anonymous."

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