Caught in a New Life Pt.2 (Patreon)

Chapter 3

While Monroe was having breakfast the next morning Lena passed by on her way out wearing a white body con designer dress with a black belt at the waist, black sheer pantyhose, a pair of white patent leather heels, big rounded sunglasses and a wide floppy white hat with a black band around the top.

Monroe loved how his wife looked in that outfit. Only this time he didn’t dare get handsy about just how much he loved it. In fact, he didn’t even dare look up at her or try to strike up a conversation. After the previous attempts that had been shot down, he had made up his mind about letting his wife signal when she was ready to talk.

“I’m heading out to go shopping for the day. Don’t you dare let me catch you jerking off again or I’m filing an instant divorce.” Lena said coolly as she made her way to the garage, slamming the door shut behind her. It was followed by the sound of the garage opening and a car driving out. Monroe couldn’t help but sigh. It was just porn, why did Lena make such a drama of it? Was all he could think about.

Lena hadn’t been lying when she said she would go out shopping. She was indeed headed to a shop. It might just not have been the kind of shop Monroe would expect her to go. Hell it wasn’t the kind of shop she would ever go unless she got a very good reason for it. Ben’s words from yesterday had stuck with her and those were reason enough to go where she was headed right now.

The drive was a long one, a little under an hour, but if there was any place she could find out more about what this whole sissy thing entailed then it would be this place. Lena thought as she pulled up in front of the overtly pink store called CC’s boutique. Judging from the store mannequins who lacked breasts yet wore the most outrageously girly outfits she had ever seen. She had definitely arrived at the right place.

Upon entering the store, she instantly spotted a young pretty woman. She had an elegant slender figure, a bright red Bob cut reaching down to her shoulders. Apart from her being a little flat chested she probably was every guy’s wet dream. Not that any guy would probably notice since she was wearing a skirt short enough that her stocking tops were plainly visible. 

“Hello, I’m looking for a certain Linda. Could you please go and get her for me?” Lena said, apparently shaking up this young girl who was quite a bit smaller than she was. She figured this girl couldn’t be Linda since Linda claimed to an expert on sissies with more than 20 years of experience and this girl looked to be just 20 or not even that.

“Euhm yeth Mith, I’ll go get her right away. Could you pleathe wait here for a moment?” The girl spoke nervously before mincing away in her very high heels, her wrists held limp at her sides. Lena slightly frowned at the girl’s terrible lisp and the way she moved, but she didn’t think too much about it. Instead she took of her sunglasses and eyed the nearby rack of clothes. There mainly seemed to be skirts on this rack they appeared to be either way to short to be decent, or just past the knee but so small at the edge that they would certainly restrict movement by a lot.

Lena was so busy looking at these strange impractical skirts that she didn’t notice Linda coming her way right away. When she did notice her, she was kind of surprised. She knew she herself was tall for a woman, but this Linda was even taller than she was. Not by a lot. She figured this woman was about as tall as Monroe, or in between the two of them. It was hard to tell since she was wearing very high heels as well.

This Linda woman looked very imposing, not only was she tall, she also was very curvy. Not out of proportion for how tall she was though. She had wide hips and thick thighs, a narrow waist and a big bust. Her long red hair made her guess she was somehow related to the slender shop assistant who was now walking behind her.

Linda herself was quite surprised. She didn’t know what she was expecting when Stephanie came to get her, but it certainly wasn’t a classy woman like Lena. She could tell this woman was high class cause of the designer clothes. Clothes she recognised because she had plenty of them in her own closet.

“Hello, I’m Lina. Welcome to my store. Stephanie here told me you asked for me, so what is it I can help you with?” Linda asked friendly. She really had two faces, a cruel sadistic one towards any sissy, and a friendly curious one towards anyone else. Especially people who shared an interest in sissies.

“So you’re Linda? Nice to meet you, I read a little about you on your website. The problem I have is kind of private and personal. I would like to discuss it someplace more private if that’s possible.” Lena said, even she found this woman to be kind of imposing. 

“Sure, follow me to my office. If you came here in relation to anything involving sissies, then I am sure I will be able to help you.” Linda said, turning on her heels and walking to the back of the store where she opened a heavy wooden door inviting Lena in.

The office was painted a soft pink, just like the other walls in the store. The desk sitting in the middle of the office was made of clear glass. On the wall behind the desk there hung a big flat screen television. Photo frames were hanging all over the place.

Upon looking over the frames Lena frowned. Instead of normal pictures with friends and family to brighten up an office these were all weird. The first one to catch her eye was a picture of a lean muscular guy with a dirty blond buzz cut. He was wearing a pair of frilly pink panties and was obviously very embarrassed about it. 

There were frames with that guy in full lingerie. Then a maid dress, a frame of him massaging a nylon covered foot, a frame with a cock in his mouth,… Over the progress of the pictures the guy’s muscles seemed to melt away, his buzz cut got longer, it was suddenly dyed red. There was one constant. The guy’s face remained beet red throughout.

Her inspection was suddenly interrupted by Linda speaking up. “I see you’ve noticed the pictures of my stepson Stephen, or Stephanie as she goes by now. They give the full timeline of her coming out of the closet. I made a point of documenting every first of hers on her journey to the sissy she is today.” Linda simply stated.

Lena looked surprised. She couldn’t believe this lean muscular guy with his buzzcut in the first picture was the same person as that pretty demure lisping shop assistant she had addressed when she just entered the store.

Linda smirked instantly recognising that look of disbelief. It was a look that made her very proud of her own achievement in how far and unrecognisable she had sissified her stepson. She loved looking back at those pictures, she loved making Stephanie recreate them just to compare them for added humiliation. Seeing his embarrassed face never got old.

“Have a seat, you told me you wanted to discuss something.” Linda said signalling to a comfortable chair across her desk. Having a quick look over the rest of the pics Lena eventually took her seat. 

“It does look like I have come to the right place. I kind of have a situation at home and with your expertise on sissies I believe you might be able to help. After all, with a stepson like that you must be an expert. It’s kind of hard to explain so let me go ahead and show you what I saw.” Lena said fishing out her phone, putting up the video and handing it over to Linda.

While the video was playing Lena explained. “You see this is how I caught my husband when I came home from my aerobics class. He was jerking off to sissy porn and it made me so mad. Especially when I talked to a gay friend of mine who told me sissies made a mockery of gay and trans people. He was the one who suggested I had a look at the site in question to find out more and maybe make him experience what it is like, so he knows what harm he caused. It was the site that led me to this store.”

Inside Linda was smiling. She recognised the sissy in question instantly. Her first customer Marcy. She knew the sissy had acquired her own site recently and it was a joy to see people actually subscribed and jerked off to it. Another big step in her journey, having a fanbase who used her or at least her image for pleasure. She could already imagine how Marcy would react if she saw evidence of this.

“Hmmm I understand, your friend was wrong on some part though. Sissies don’t make a mockery of gay or trans people. They are another sub group entirely. Sissies thrive on submission and humiliation. They adore everything that’s over the top girly while mostly staying a bit androgynously body wise.” Linda explained leaving out the part where she liked to force guys down the sissification path.

“When it comes to the main group of guys jerking off to so called sissyporn I am afraid your gay friend is right. They usually do it out of homophobic tendencies, to feel better than people they see as gay. In that sense giving them a feel for what it is like might be a fitting punishment.” Linda carried on explaining. She knew it was a lie, but she would love to seal the fate of yet another man. A new customer was always welcome. Besides, if that gay friend had suggested this then this lie might be true for her husband anyways.

“There is no way my husband would ever approve to something like this. He would never go along with wearing even a simple pair of panties. Not in a million years.” Lena sighed deeply. She knew Monroe to well to believe he would agree to this kind of punishment.

“Then don’t give him a choice. Make him choose between a divorce or taking the punishment. It might also help not to go full out sissy right away. Just build up to it over time. You know how men think with their cock right? Well we have a perfect device to use that against them.” Linda said with a smile.

“Oh I would put him in front of that choice if I could afford it. He ditched his last wife like dirt, and he has enough lawyer buddies to back him up and make sure I can’t even get my clothes out of that divorce. Maybe this is just hopeless.” Lena sighed again.

“I wouldn’t really say that if I were you. In fact I do think you have a pretty strong case when it comes to taking the divorce to court. You should actually insist on taking it to court even. I think you underestimate the power of shame. If you show this movie in court dissing up a story how you found him trying on your panties sometime. You could deface him as a big sissy to all his lawyer buddies, word that would certainly travel fast.” Linda said with a broad smile.

“How much do you want to bet that he’ll do everything to keep that from happening? Even if it wouldn’t win you the case he would never go through with it if he knew what’s at stake. I am pretty certain of it.” Linda continued seeing the hopelessness being replaced with a sudden curiosity.

“Then what, if I convince him not to go to court then what? We just part ways, each taking half of the money and continue our lives like that?” Lena asked sceptically.

“No, then you slowly guide him towards becoming a sissy. It’s justice for him being a big homophobe and your life will never have been easier. You would be in full control of everything and if you do it right, have a loyal servant to boot.” Linda seeing how Lena’s interest was peaking. She knew she had her convinced. Now she just needed to reveal her plan and she soon would have a new customer to sissify.

Over the course of a few hours Linda informed Lena about all the benefits having a sissy husband would have. She also informed Lena about how she should go over getting her husband to that point, telling her she could always call to her for help. When the two women parted, they both had a big smile plastered across their faces.

Lena made the drive back home and spent the rest of her day with friends doing some real shopping and having dinner. She felt certain now about how to go forth for the first time since she had caught Monroe jerking off to that sissy porn. Tomorrow she would kick the plan she and Linda discussed into action and if everything went right, she wouldn’t have to worry for another day in her life.

Chapter 4

The next morning, just like the morning before Monroe was quietly eating his breakfast. That sinking feeling of being around his still angry wife remained. For a moment he was considering just getting a divorce. If things remained like this then he would be way better off with a divorce. Sure Lena was a stunningly beautiful woman and he loved being around her, but no one was irreplaceable. With the help of some of his buddies from back at the club he would make sure Lena disappeared from his life with just the clothes in her closet if she was lucky.

Monroe hadn’t quite decided yet, but after sleeping in the guest room for a couple of nights and not being able to even have a civil conversation with his wife the thought was certainly starting to grow. It would only continue to grow the longer this situation continued.

To his surprise however it was looking like things were starting to change after all. For the first time since he had been caught his wife didn’t straight up ignore him coming down stairs. In fact she had a big smile plastered across her face as she approached him. It was a sudden big unexpected change for sure.

“Good morning Monroe, I think it’s about time we had a talk to sort out what has happened and how to go forward. I have done a lot of thinking these past few days and I think I have come up with a solution that’ll work for the both of us.” Lena said in an excited tone.

Even after her conversation with Linda she still wasn’t sure whether her husband would take the bait to go along with their plan. After all what she was about to ask was rather big, especially from someone as proud and with such old-fashioned ideas about what men were like as her husband. He was a macho and it wold make things harder for sure. Still she was convinced it had at least a chance for success.

It seemed like she at least had his attention now. A big smile had crept up his face. “Great, that’s all I wanted, an adult conversation so we can finally sort this thing out.” Monroe said just as excited as Lena had sounded. Finally his wife had come to her senses. Now that they could talk he could inform her about how it all had been a one time thing, how it would never happen again and just live on their life as if nothing had ever happened.

Lena had other ideas though. “Well I’m very glad you also feel this way, I’m sure we’ll get this sorted out. So the solution I came up with is as follows. I would like if you wore one of these. It would make me feel safe knowing that you aren’t jerking off to those disgusting porn movies or cheating on me like you did on your last wife. I would keep the key, but of course I open it up whenever we have sex.” Lena said confidently, placing a grey stainless-steel chastity cage with simple padlock on the table. 

The chastity cage was nothing as outrageous like the normal custom-made CC’s cages Linda was happy to give along as a gift for new customers. Nothing like the one she had forced on Marcy, her first real customer. Lena’s situation was different though. The deal she proposed had to be much better than the prospect of court, so Linda had given her a model that looked as boring as possible.

Monroe’s smile instantly disappeared, had his wife really gone crazy? He recognised the device all to well, at least a lot of sissies in his porn had worn in and there was no way he would wear that damn thing. Not in a million years.

His excitement had quickly turned into anger as he shouted “What the hell Lena, you can’t be fucking serious. I’m not wearing that damn thing. You’re crazy for even thinking that. I’m a man and I get to use my damn cock whenever I damn well please is that understood?” Monroe shouted, suddenly not seeming all that interested in resolving this matter or an adult conversation anymore.

After Monroe’s outburst Lena lashed out in anger herself. “Really?! I’m trying my best here to save our fucking marriage and this is how react? You don’t even consider what I proposed. Well just so we’re clear. This is only going to work the way I proposed it. Either that or a fucking divorce cause quite frankly I don’t trust you with you cock when I’m not around. Here I was thinking I had married a man, only to find out he jerks off to guys in panties.” Lena retorted.

It really stung Monroe’s ego to have his wife describe his indiscretions this way. He was a full-blown hetero guy, those sissies were even girlier than most real women if anything. It was nothing like Lena described. “Damn it Lena, it’s nothing like that, even you have to acknowledge that!” Monroe shouted in frustration. Thinking he should maybe just let his wife have her wish and go for that divorce. Let’s see who had the last laugh then when she got kicked out on the streets with just a suitcase of clothes.

“Oh really? That’s bullshit anyways, if you really don’t think it’s anything like what I claim then why don’t you convince the fucking judge of that when this goes to court. I’m curious what the verdict will be if I show that video I made for the whole court room, dissing up a story about how that was the confirmation of my worst fears. Fears that my husband wasn’t the man I thought he was. How I had my suspicions when I had first caught you holding up my lingerie in front of you while inspecting yourself in the mirror. How I found my soiled panties that had been stretched a little too much up front.” Lena shouted back further elaborating on the idea of a story Linda had proposed but taking it a step further now that she was angry.

“I… I never did any of those things you’re just making that up as you go, and you know it.” Monroe retorted no longer screaming. His face had gone pale and he started to look scared rather than angry now. 

“You mean just like you knew that your previous wife wasn’t cheating on you, but you were on her? That you destroyed her self-confidence so she would take your advice to go to that personal trainer you set her up with? The one you paid to kiss her on the lips and snap a pic of it so you could destroy her in court even though she didn’t even provoke or want to kiss him? You’re right I would be making the lingerie try-ons up, but how will you prove it? I know I don’t have proof like that picture from the personal trainer, but I think my story will hold up after that video.” Lena said, a smile starting to resurface.

To his horror he knew Lena was probably right. He didn’t know she even knew his first wife, much less how that story had gone down, but apparently she did. It didn’t help his case at all. Trying to get his wife to have sympathy for him would be hard now that she knew this part of him. The part where he wasn’t to shy to lie and set people up to get his wishes when it really came down to it. It wasn’t a part he was all to proud of, but it had helped him along in gathering his fortune.

A fortune that was now on the line. Lena wasn’t stupid, and since a divorce was just discussed he doubted she would let herself be set up like his previous wife had. Even if that was the case he really didn’t want any of her story or the video to end up in a court room. If he with the help of his lawyer buddies could somehow convince the judge in their favour it was fairly unlikely that his reputation would survive. 

He would be the talk in all of his social circles. Known as the sissy who loved jerking off to other sissies and there would be no way around that. Knowing how his buddies thought about those kinds of people, the same as he did, he was certain to get ridiculed and isolated. Even finding a new wife would be out of the question.

“Anyways, I’m heading out for the day. Tonight when I get back I want to either see you wearing that damn thing so things can go back to normal, or we’ll start the papermill for the divorce. So think about this very well, I’ll unlock that padlock now meaning you’ll have one chance to lock it in place since I’ll be taking the key with me.” Lena said before doing just that and leaving without another word.

Monroe was left speechless and in shock. Shit what would he do now? The more he thought about how this day would play out at court the more his stomach turned. He had about a 30 percent chance of winning the case with every scenario he came up with which wasn’t a lot. Even then he couldn’t imagine a single scenario where his life wouldn’t be ruined. 

The more he thought about it, the more attractive the idea of just putting on that damn cage was becoming. Lena had said everything would go back to normal right? Sure there would be no masturbation, no cheating, but he would still get to have sex with his wife as much as he wanted right? She would just unlock him, and they could have sex. At least that’s how Lena had made it sound.

If that was the case then would this really be so bad? After some time Lena might even just forgo that cage all together. If he kept his manners for a week or so then maybe she would see that it wasn’t necessary at all.

Even if that didn’t happen he could maybe just try to destroy that video of him Lena would eventually become less suspicious of him and if all the evidence was destroyed he could turn the table on her. If he claimed she had locked him up in that damn thing he could get divorced cleanly with his whole fortune. Her stories about the lingerie and the jerking off would just be laughed away. He hoped it wouldn’t have to come to that as it would take a lot more time in that damn cage and be a lot harder to pull off than convincing Lena he didn’t need that cage anymore an learned his lesson.

A lot of reasoning and pondering later Monroe decided to just put on the damn chastity cage like Lena had demanded. Sure it was embarrassing, but it was a lot better than taking a divorce to court with the evidence his wife held over him. Besides he would only be wearing it for a limited amount of time. One week, maybe two weeks tops, he told himself as he sighed before slipping on the cage and locking it in place.

The remainder of Monroe’s day was whether he had made the right choice or not. Well it was too late to change his mind now. He was locked and the key was far out of his reach, wherever his wife was hanging out right now.

With a deep sigh Monroe decided to go to the golf club. The question of whether or not he had made the right choice was driving him crazy. It wasn’t going to change so he decided to just try and distract himself from thinking about it.

While all that was unfolding back at their house Lena had gone to the gay to tell the latest developments to Ben. She had confided in him when she first caught Monroe. He had seemed very supportive and even suggested checking out that store. She felt like she owed to keep him in the loop now. 

There was also the fact that she couldn’t really talk to anyone about what was going on at home. Surely none of her girlfriends would understand. Ben just offered to listen and let his friend vent about what was going on. He acted compassionate towards Lena who obviously wasn’t all this sure about this. She was too good of a person to really feel comfortable with Linda’s plan the way she had explained it.

Inside Ben couldn’t be happier though. He really looked forward to seeing that plan in action and he would be there all the way to support her. If Lena felt like Monroe deserved it she would have no qualms about pushing through. She had always had a strong sense of justice. Right now it didn’t seem like he would even need to make anything up. With how Monroe had acted according to her this morning he had more than enough fire power to keep Lena on track with the plan.

“Look Lena, I think it’s very important that you strictly keep to the plan this Linda woman proposed. It sounds to me like Monroe is just looking for an excuse or opportunity to destroy you. You know what he did to his last wife, and I doubt he will hesitate to do the same to you if given the chance. I think it’s important you don’t give him that chance. You can’t eve risk giving him an inch I’m afraid.” Ben said in a serious tone.

Sighing deeply Lena said. “I know, it’s too late to call that plan off no anyway. The only time I’ll be at ease again is if Monroe ever gets as submissive and compliant as Linda said he would with her plan. Oh what have I done?” Lena said mournfully, her anger had gotten the better of her this morning making all her doubt and angers about her husband boil up at once.

“Hey Lena, look at me. You’re going to be fine and I’ll do what ever I can to make sure of that. You are doing the right thing here. After what he did to his last wife and after what he’s certainly going to do to you when given the chance this is more than justified. Don’t you ever doubt that.” Ben said.

“I know, I know. Anyways, I think I better get going. Maybe he hasn’t even put that cage on and we can take it to court right away.” Lena said nervously. The confident ultimatum she had given Monroe this morning seemed to have disappeared.

“Goodbye Lena, I’ll see you around.” Ben said cheerfully, trying to bring some of that cheerfulness to his friend, knowing she could use it. As Lena left the door Ben was cracking a big smile. For a far as he Knew Monroe he had no doubts he would be wearing the chastity cage. He had always been a bit of a coward, never taking action as long as he hadn’t made sure the odds were stacked against whoever he was up against.

The thought of Monroe’s cock under lock was wonderful on its own but he would have never dreamed of a plan as deliciously devious as Linda’s. He would love to have a talk with the woman himself, maybe he could even give her a few hints regarding Monroe without risking that his friendship with Lena would be damaged. If not just her plan would be more than delicious enough already and he couldn’t wait to see it in action.

Going home Lena was worried about how things would go. Much to her surprise her husband was rather silent and awkward instead of his usual charming confident self. It gave her some added confidence. “So Monroe, have you made your choice?” She asked trying to sound as confident as she possibly could.

“I’m wearing the cage.” Monroe said quietly. He wasn’t at all proud of it. Having his male pride locked up was more embarrassing than he had imagined. Especially having to confess it to his wife even if she had been the one who had left him little choice.

Lena looked surprised for a moment. It was followed by relief and a slow growing excitement. She had fully expected Monroe to refuse the cage, and then she would be left with having to go to court. Something she wasn’t sure she could handle as easily as she had claimed in her anger this morning.

Walking over to her husband she surprised him by instantly unbuttoning his pants and lowering his underwear. A slight gasp escaped her lips as she saw his cock locked away in the stainless-steel tube. A squeal of excitement later she kissed Monroe full on the lips. “Oh my god, you really did it. I’m so proud of you. Thank you for also making an effort to safe our marriage.” Lena gushed.

Monroe was caught off guard by Lena’s excitement. He hadn’t expected her to react this way for sure, but he didn’t mind one bit. Finally he and Lena were sharing some passion again. Something he had thought was lost after he had been caught jerking off to that sissy porn.

The passion didn’t stop there either. A few minutes later the couple found themselves in the bedroom, they stripped completely, and Lena took out the key to unlock Monroe’s cock. What followed was hours of hot steamy sex, better than Monroe remembered having. The new-found excitement from his wife certainly was showing through.

After their wild sex session they took a shower and Lena locked him right back up. Monroe was about to object when he stopped himself. This was the best sex he had ever had in a long time. His wife seemed happy and it seemed like she meant it when she told him the cage was only for when they weren’t fucking.

He still wasn’t happy about having his manhood locked up, but it was better, way better than the alternative so he didn’t object. He joined his wife back in their bed for the first time in a few days, some of the doubts about this cage where removed as they both slowly drifted off to sleep.