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Caught in a New Life Pt.1
🕑 Added 2019-11-20 14:53:32 +0000 UTC
Intro
Monroe Smith had everything pretty well figured out for himself. He was 43, his hair was brown and slightly greying, but his hairline hadn’t really receded thanks to the hair implants he had done about a year back. He had never been a big guy when it came to muscles, but it didn’t really matter all that mattered to him was staying in shape.
While he didn’t bother going to the gym his way of staying in shape was watching what he ate. Junk food never entered his house. As a result, he looked fit, but in a lean way. His eyes had a mysterious grey colour and he had a smile that could charm any woman, something which he had tested over and over. He stood at 6’1” and was a real womaniser who loved the hunt.
Back when he was fresh out of college, he had started a small software company which had done pretty well. He had been able to sell it for a small fortune to one of the bigger players on the market. He had opted to receive his money in stocks however which had been a good bet as over the few years following his sale, these stocks had tripled in worth.
He was pretty much settled for life which was something else that made it so easy for him to get the women he liked. It was clearly evident when you saw his wife Lena. She was a stunning beauty who really didn’t show her age.
Lena was 31 years old, but if she claimed to be in her early twenties you would probably believe her. Her German heritage clearly showed in the stereotypical blond hair and bright blue eyes. Standing at 5’11” she was an imposing woman, yet despite her length she was very well proportioned. She had long legs, a full firm butt, flat stomach and a pair of D cup breasts. Despite her impressive bottom and breasts, she did still look slender due to her length. Neither of her features looks exceptionally big on her body.
She was Monroe’s second wife. He had divorced his first wife and high school sweetheart about 10 years ago, but their marriage had been bad long before that. Monroe had cheated on his first wife a number of times and Lena knew it. She had had an occasional talk with his first wife and there were no hard feelings between the two women.
When it came to their relationship Lena had no illusions. She knew Monroe had married her because it gave him something to brag about. She in turn also quite enjoyed the fact that he was rich, but apart from that she also liked his charms. She was however cautious when it came to loving her husband. She doubted that he would be able to keep his hands-off other women forever.
If things would go that far she wouldn’t just let herself be brushed aside like what had happened with his first wife. If he wanted to divorce her she would make sure she could keep on living a comfortable life without having to go and look for work.
You could say their relationship was a strange one, but so far it worked out for the both of them. They had been going strong for 9 years so far without incident. Lena did have her doubts about whether Monroe stayed fateful or not, but right now she had no tangible proof of him cheating. She had had her doubts from the moment his ex-wife had warned him, so the doubts were nothing new. Besides as charming as her husband was Lena doubted if he could do better than her, she was a walking wet dream and she knew it.
Chapter 1
It was Tuesday evening which meant Lena was getting ready for her aerobics class. While she didn’t work she certainly kept busy building and maintaining a social life and just generally doing things she wanted.
There wasn’t a day where Lena didn’t do something which had made her a pretty well-established figure among the wives in the gated community, they lived in. Most of them where trophy wives who didn’t really work. The closest thing to Working any of them did was going to charity events and supporting charities they could get behind.
Monroe on his own was also pretty well known in the community, but he was no where near as active as his wife. Most of his days were spent selling and buying his stocks, continuously growing his fortune which was already bigger than what he would probably spend in his life time. At this point hoarding money was just kind of a hobby he really enjoyed.
Apart from hoarding money Monroe sometimes went to the golf to enjoy some sport with his buddies. Meetings and events to gain more insight in the stock market were also on his agenda, and each Friday he went to the local country club’s special events.
On her way-out Lena quickly passed by her husband who was sitting on the couch reading through the latest developments on the market from his phone which was now screen sharing with the huge television screen. Monroe had always been a man of gadgets and he loved the pure ease it brought to his life.
He had always been fascinated by technology and the possibilities it brought. He had foreseen what a big role it would play in the futures which is why he had initially started up his software company. As far as he was concerned technology was the future, and most of his investments had been in that market. So far it had only made him even richer. After all technology was an increasing need of everyday life for most people.
These days a good smartphone was all one really needed. He could do his transactions form there, use his social media, watch television, … It was also a device he could take along anywhere he went to do the same things with the same exact ease as at home.
The only real downside to this wonderful device was the rather small screen. Yet with the ease of screensharing these days it only took a few taps to pull it’s screen up on one of the many big flat screens throughout their house, which is what he mostly ended up doing. At that point the device served more like an advanced remote.
After sharing a quick kiss on the lips with his wife Monroe turned around to admire her beautiful figure. It looked perfect in her tight aqua leggings and sports bra which hugged her butt in the best ways while exposing most of her beautiful strong back. His work surely looked gorgeous and even after these 9 years he still couldn’t get enough from looking at her. One thing he certainly didn’t mind spending money on was her. After all he got to enjoy the results of all her fitness classes and stunning sexy outfits she bought.
Now that she was gone however Monroe had the chance to enjoy another hobby of his, watching porn, and more specifically sissy porn. Ever since he came across this kind of porn it had been one of his favourite genres. If someone had described it to him before he stumbled across it on the web, he would certainly have called them gay which was absolutely something he detested.
Monroe was quite homophobic even though he would never really admit it. In today’s society that wasn’t all that accepted anymore. Hell, Lena herself had some friends in the LGBT community and sponsored a number of charities supporting LGBT rights. It kind of hurt that some of his money was going to such things, but there was no way to help it.
While he knew for a fact that most of his buddies thought the same about gay people or faggots like they mainly referred to them, he knew better than to be openly against it. That much had been clear when one of his old buddies his company went bankrupt due to his stance on LGBT rights. Society as a whole had become way more openminded and usually when someone with some amount of power was against such a thing outrage followed.
To Monroe getting off to these sissies wasn’t gay though. The only gay ones were the sissies themselves. After all what kind of self-respecting guy would do such a thing to himself? He had stumbled across this genre of porn by accident when he saw a very pretty fragile looking girl serving a small group of men in the thumbnail.
He had instantly opened the video since pretty weak submissive girls were one of his main fantasies. None of the women he had been with had been like that. They had always been pretty strong-willed which Monroe hadn’t really minded at all, He had used many of them for a night of pleasure regardless. It was a pity that the most stunning women always tended to be strong willed, but that didn’t bother him to much. Just like with Lena he loved having a woman who made all the other men jealous. The sex was pretty great as well even if she wasn’t the submissive toy he would like.
Somewhere during that first video while he had already been consumed by his masturbation and near the edge of an orgasm, he saw one of the men this pretty girl was serving lower her panties. It didn’t really register at first but between her legs was a cock. Well more like a cute little dicklet. You couldn’t really call it a cock. It took a few moments to seep through in his overtly horny brain that this pretty girl was in fact a guy? It didn’t really make sense. When reading the title “Sissy serving me and my friends”. He hadn’t really thought twice about it either. He had just thought that Sissy was the name of the pornstar.
Despite his realisation that the girl was actually a guy in very pretty slightly over the top lingerie he still blew his load to said video. It had confused him a bit at first, yet the next time he wanted to masturbate he had looked up the term sissy again. It was a pleasant surprise when he saw many more thumbnails of very pretty fragile submissive “girls”. Like that a new favourite category was established with Monroe.
These sissies couldn’t really be called guys with any stretch of the imagination anyways and they were often prettier and more outrageously girly than the female pornstars. Their weak fragile looks were just his type. He loved the idea of having someone under his complete control.
A few days back he had gotten a recommendation for a premium site in the mail box he used for his porn subscriptions. After all he wanted to keep all that junk and those ads away from his normal life. This recommendation link seemed promising though. It promised to witness the birth of a sissy. Monroe thought that he might as well check it out and subscribe. The subscription fee wouldn’t really hurt him anyways.
At first Monroe was slightly freaked out when the first thing on the site was a photo set of a guy wearing a red lacy thong. Sure he looked skinny, had long hair, but he was still obviously looking at a guy. The next thing was a video of the guy who if he went off the site name was called Sissy Marcy, dancing and singing in his panties, reading a fashion magazine and finally jerking off and cuming in his panties. While the guy looked somewhat effeminate, he was still definitely a guy. His pubes underneath the panties weren’t particularly nice to see.
What followed was a compilation of that long-haired guy cuming in a variety of different panties, all way frillier than the red lace thong he had worn that first day. He also always seemed to have an obviously dirty pair of boxer shorts pulled over his head while he masturbated. Which the text under the video claimed to be his masters. It was still very disturbing with the body hair present, but it was also somewhat hot to Monroe to witness the guy obeying such depravity.
When the next video featured this same guy now completely smooth with a pastel pink heart shaped pubic bush Monroe was sold though. He liked where this was going, and he definitely wanted to see more.
Since that moment Monroe always pulled up this new site. He was pleasantly surprised when a new video had been posted. In this one Marcy was wearing a full set of lingerie just like in the video before that. It was a different set though and once again very frilly, it featured a hot pink thing sticking out of a lacy looking flower of sort. It was quite strange, but Monroe liked what he was seeing. Monroe liked how the guy from the first photo set was really shaping up to be a pretty sissy.
He watched intensely as the guy first modelled the set striking various poses, then the video got cut and went to a scene where he once again pulled a pair of boxers over his head. Much to Monroe’s surprise though the sissy’s hand didn’t go to his cock, instead his finger went up his ass and he started fingering his butthole.
A second surprise came when a white goo squirted out of the pink thing sticking out of the panties. It took a moment but then it dawned on him. The sissy was wearing a chastity cage and masturbating by fingering his ass. Monroe licked his lips as he pulled up that masturbation scene again. It looked like the sissy was well on his way to becoming a hungry butt slut and he loved the new change.
While watching the scene for a second time ferociously stroking his own cock while the fingering sissy played on the big screen, he failed to notice that his wife had come home. He was way too consumed in his masturbation and usually it wasn’t really a worry either.
Normally his wife went to the sushi with her girlfriends after the aerobics class, then they headed to a lounge bar to enjoy some cocktails over some gossip. She usually didn’t come home until after midnight on Tuesday evenings and as a result Monroe wasn’t at all worried about being seen.
Lena on the other hand had exceptionally come home right after her aerobics class. One of her friends had cancelled because her chihuahua had died, another couldn’t stay for the usually sushi and cocktails because she needed to accompany her husband to a big company event right after class, and her last aerobic friend and her had decided that going just the two of them wouldn’t be the same so they would skip until next Tuesday when they were all able to go out after class.
It was needless to say that Lena was shocked when she found her husband jerking off to such a depraved porn. Instead of instantly interrupting however she pulled out her phone and started filming the whole thing. If she was going to accuse him of anything, she needed more proof than just word against word. A video would serve as a good security blanket if he would threaten to divorce her.
Monroe was really starting to build pace masturbating now. He was pumping his cock harder and harder setting his rhythm to the finger blasting of the sissy on screen. He licked his lips imagining it was his cock plunging in that tight looking hungry hole.
Mere minutes later the sissy started moaning even louder into the boxers pulled over her head. Monroe in turn let out a loud grunt and then it happened. A white goo started spewing out of the pink thing in the front of the sissy’s panties at the same time as Monroe grabbed a tissue and emptied his balls into it.
At the exact moment he had started cuming Lena who had quietly stood by and filmed this whole time started screaming. “What the fuck are you doing? What kind of nasty shit are you even jerking off to you fucking pervert?! God this is so gross! You cum faster for this than when you are fucking your own wife who is by the way a real woman. Are you some kind of perverted faggot or what?!” Lena asked furiously.
The moment his wife had started screaming a wave of panic gripped Monroe. In his panic he pulled his hand away from his cock, but that only ended up with another shot of cum squirting up and hitting him in the face. It grossed him out and made him reflexively wipe it away, only the tissue he was holding was soaked in so much cum that it just ended up covering his face in even more cum. His cock erupted in two last shots, one on his chest and one on his stomach before his orgasm ended completely. With the panic gripping him it hadn’t even felt good. He only felt a harsh sinking feeling in the pit of his stomach.
“Fucking hell you even cum on your own face you bastard. Is that it, is that what you dream of becoming pervert?” screamed on as she saw his cock continue to sputter cum. While he wiped his face with the cum filled tissue.
“No please honey, I can explain it. This isn’t what it looks like I swear! It’s…” Monroe started defending himself, but his wife just cut him off.
“I don’t want to hear another word of you and don’t honey me. You disgust me! I am heading to bed and I don’t want to see you again for the remainder of the day. You can sleep in the guest room or wherever, but I don’t want you in my bed.” Lena screamed as she turned around and walked off leaving a defeated Monroe sitting on the couch covered in his own cum.
He tried to set everything straight by shouting after his wife to get a chance to explain himself. “Hon… Lena please wait!” It was in vain though; his wife didn’t turn back she just kept on walking, quickly disappearing out of view while he sat there on the couch defeated and worried, his cum was slowly cooling and drying on his skin.
Without much else to do Monroe grabbed another few tissues and started cleaning himself up as good as he could. There was no way in which he could explain himself to his wife now. Going after her didn’t really seem like a very good idea. Not with how angry she was. He would have to let her anger sink a little before he would be able to have an actual constructive talk with his wife. A talk that didn’t just end with her screaming at him and refusing to listen.
Angry at himself for not being more careful Monroe headed up to guestroom. He took a shower in the adjoined bathroom and headed to bed alone. Why had he not heard his wife come home early? How could he be so stupid as to let her catch him watching something like that? Those were the questions going through his head as he drifted off to sleep.
Chapter 2
The morning after at breakfast Monroe approached his wife to try and straighten out the situation. “Look Lena, about last night.” He started calmly but instantly got interrupted by a harsh cold stare from his wife. It was instantly clear that she wasn’t up for discussion yet.
Lena then just looked back down at her tablet, reading the paper while sipping at her coffee. “Like what you were doing need explaining. It seemed pretty clear to me you perverted fag.” Lena muttered under her breath. Still loud enough for Monroe to hear.
His wife calling him a faggot was what hurt most. It was the last thing he wanted to be compared to. He detested homosexuality let alone being considered gay himself. Jerking off to such a fragile feminine looking thing wasn’t gay right? It couldn’t be, but he knew that it was not a discussion to be having right now with how angry Lena still was.
After her coffee Lena got up leaving Monroe alone to get dressed and head out. Today was the opening of the first LGBT bar near their neighbourhood. A project of one of the charities she supported. She went with somewhat mixed feelings after calling her husband a faggot. She knew it was a derogatory term, but she had been so angry she hadn’t been able to help it. Besides, what Monroe had watched seemed more like some twisted perverted version.
It surely hadn’t been about the love between two people no matter the gender she fiercely supported. It had looked more like a fetish, a mockery of what LGBT stood for and it only made her angrier. There were enough prejudices regarding the LGBT community already that it could really do without the fetishized porn versions.
Lena didn’t really know what to think about it either. She felt cheated on, especially with Monroe’s past and the way in which he had cheated on his ex-wife. She also felt lied to, was her husband secretly gay and had he never told her about it? Surely if that was the case, he could at least have told her. She would have been supportive at least. Then again what she had caught him watching surely was downright perverted.
She tried to put what had happened out of her mind, but she simply couldn’t. The party only barely helped to form a distraction. Maybe she should talk about it to someone, but to who? She didn’t really want to admit she was having relationship troubles to anyone and she certainly didn’t want the fact that her husband was such a perv to get out. After all if she didn’t immediately divorce him then it would be bad for her own reputation as well.
In the end Lena concluded that she had to confide in someone. Someone who could maybe give her some good advice. She decided to confide in Ben. He and his husband Jason were the ones who had established this club and would run it.
Ben was a 6’3” tall Arab guy. He had dark curly hair, a full dark beard, light brown skin, dark brown nearly black eyes and a muscular body with a lot of body hair all over. The last thing one would expect when meeting Ben was that he was gay. The same thing went for his husband Jason who at 6’2” was only just smaller than Ben. Jason was shaven clean all over, he was black and had a short curly buzz cut. While Ben was bulky muscular Jason was rather lean muscular.
Lena had met Ben in her first year at college. Back then he had only just arrived in the country. His English wasn’t very good yet and he was pretty much set up to fail at college because of it. Lena had pretty much instantly taken a pity on him, he clearly meant well, but no one seemed to want to give him much of a chance. Throughout the years at college Lena had helped him with his studies as much as she could they had become very good friends and Ben was eternally grateful for the help Lena had offered.
Up until that point he had had a hard life. He had to cut all ties with his family, flee his country and change his name all because back in his country gay people still got the death penalty. Here int the west things were a lot better, but even here gay people were still judged and discriminated much to Ben’s frustration.
When Lena pulled him aside, she asked. “Look Ben, I have something very personal to talk to you about and I would very much appreciate if this could stay between the two of us. If you don’t think you can honour that I rather have you tell me now okay.”
“The least I can do for you is listen. So Lena, tell me what’s on your mind. I swear I won’t tell a living soul about it no matter what.” Ben said even though Jason was the best husband Ben could wish for Lena was without a doubt the best thing that had ever happened to him. In many ways he had Lena than for his life. If she hadn’t helped him like she did back when he had no one and no one willing to help him he would have probably ended up living under a bridge somewhere with a crippling drug addiction. So helping Lena was the least he could do.
“Alright, can we maybe go in the back to the office? I have something to show you and it really isn’t pretty and I really don’t want anyone accidentally seeing it or picking part of it up.” She said in a serious tone. Without another word Ben led her back in the office behind the storage room and locked the door.
Back in the office Lena played the video she had made of Monroe masturbating to her friend saying. “Yesterday when I came back from my aerobics class, I caught Monroe like this. I really don’t know what to think or make of this at all.”
Ben had to blink a few times to believe what he was seeing. Monroe just sat there jerking to a very girly looking guy. The moment he shot a part of his load on his face was just precious to Ben. He had disliked Monroe from the moment he first met him. Despite the fact that he wasn’t openly against the LGBT community Ben saw the disgust on his face each and every time. Sure it was subtle, but Ben knew that look all too well.
He had always thought Lena deserved way better than Monroe. In Ben’s eyes Monroe was everything that was wrong with society today. He was homophobic, but it was more than that. Ben couldn’t shake the feeling that Monroe was also racist. A guy who thought having a ton of money granted him the right to do whatever he wished. He had warned Lena a couple of times, but she wouldn’t listen to him.
Lena had fallen for Monroe for his charms in the first place, not for his money, but it was a big factor as to why she had stayed with him. She had a very easy life with a husband like that, and the two of them got along fine. Ben didn’t blame her for that, he did know however that Lena had never truly let Monroe into her heart, afraid of the hurt he could cause her, the hurt he had caused his ex-wife.
That together with the doubt Lena and anger Lena was feeling now, paired with the blackmail Lena had with this little film the wheels in Ben’s head started turning. He could safe his friend from the humiliation of going through a divorce, let her continue on with her easy life, guarantee that Monroe wouldn’t cause her anymore trouble and take some revenge for how he had been wronged by society on a person who stood for everything that was wrong with said society.
Ben knew he would have to lay it on gently, let Lena come to the conclusion herself. He was certainly planning on guiding her slightly in the right direction though. For all he cared he would be doing her a big favour.
“I see, he is clearly jerking off to sissy porn it’s a known phenomenon within the LGBT community. Mainly straight homophobic men jerk of to this stuff that mocks gay and trans people. They do it to feel better about themselves and justify their hate towards the community for being pathetic.” Ben explained. It was a lie, sissies were a part of the community although they were more a fetish thing for most people. A daintier version of a crossdresser who had a thing for humiliation. He just needed something to fuel Lena’s anger a bit more so she would be more open to the suggestion he was about to give.
“In my experience the people who jerk off to this kind of thing just aren’t well aware of what they are doing. If they knew how it would feel they probably wouldn’t do it. If you look up the website it came from you might find more. You should be able to find it with that film you made, after all I spotted that the video, he was watching had a watermark in the corner.” Ben explained, choosing his words wisely in the hope that Lena would decide that giving Monroe a feel of what it was to be a sissy, even just for a day.
Ben smiled at the thought, as far as he knew Monroe that would really sting which was exactly what he was hoping for. Oh it would serve as such poetic justice. He only hoped he would be there to see it if it happened.
“Thanks Ben, I guess I’ll just go home and try to figure it out since I am in no real mood to party. Please remember your promise and don’t tell anyone about this.” Lena said, she looked calm and collected, but Ben knew her well enough to see that she was hiding her anger.
“That’s alright, and I won’t forget my promise. Thank you for swinging by. It means a lot to me and Jason. Take care and I hope you can solve this mess with your husband quickly.” Ben replied, giving Lena a hug before she headed home.
Once she arrived at home, she ignored Monroe completely and headed straight up to her room instead. There she locked the door, still not feeling like sleeping with her husband. Once alone in the room she pulled up that video again feeling her anger boil up again. She tried to ignore what was happening in the video she had made and instead zoomed in on the watermark.
It read “Sissy Marcy: A Journey into Sissyhood”. Going to the site she was greeted with a pastel pink screen, the site title sat on top in a bright pink cursive pink. In the middle of the screen sat the usual warning that the site was adult themed and that you had to be 18 or older to enter.
Clicking through Lena came onto a page with a big picture of a rather feminine looking guy posing in a set of over the top lingerie. Lena had to admit that it looked cute in some way, not as perverted as the fingering with an obviously dirty pair of boxers pulled over the head as she had witnessed yesterday. Underneath the picture sat a small text.
“Hello,
I’m Marcy and I would love to welcome you on my site. Here you can see my Journey of finally coming out of the closet and embracing my nature a true sissy. I aspire to be the best sissy I can be and make as many cocks as possible cum which is why I created this site. Sadly I can’t be there to receive all your loads, but it fills me with joy to see new subscribers to my site producing a daily load of yummy cum for me.
Will you subscribe to my site? I certainly hope so as I provide new top mastrubative content at least once a week. I would here by also like to thank CC’s boutique for helping me realise my dreams of becoming the most girly looking sissy ever. All my adorable outfits and lingerie sets are from there. If you like them be sure to check them out in the link below. Just click on their storefront window and it should take you right to their website.
I hope to see you inside.
Hugs and Kisses,
Sissy Marcy.”
Scrolling down there was a picture of a pink store that had the name “CC’s Boutique” written in a big pink cursive script right above the door. The storefront window was filled with slender flat chested mannequins wearing the most outrageously girly outfits Lena had ever seen.
Clicking through to the site Lena was surprised to see that it was in the next city, about 50 miles away. The store claimed to be experts on everything sissy. Maybe that would be a good starting point for Lena to learn more about sissies. Surely the owner Linda, who claimed to have more than 20 years of experience with sissies would be able to tell her more about it, and maybe help her come to a solution of how to go forward with her husband.
Tomorrow Lena would go there and see for herself she thought as she shut off her phone and went to sleep. Monroe’s worries about his wife’s anger had only grown. For a moment he had considered joining her in the master bedroom, but he quickly decided against it, realising it would be a bad idea. With a deep sigh he moved back to the guest room for a second night.
