Chapter 9
Once off the bus Mark snuck to his house as good as he could. Hiding behind bushes and hedges whenever he spotted someone. He really didn’t want to run in any of his neighbours with this big pink shopping bag. It would mean nothing but trouble since he realised full well that he wasn’t actually loved around here after all his vandalism.
Once at the house Mark chose to throw the bag up on the little roof above the door portal. He had used that before to sneak out of the house and get back in when he shouldn’t, but now it would ensure that he would be able to sneak it inside without his parents seeing that bag. Afterall it was hidden well out of view and he could get to it whenever it was safe.
Walking to the front door Mark spotted both his parents at the kitchen table eating breakfast. With that information he decided to get the bag first thing when he arrived upstairs. It was best to not to wait with such things after all. What if it would blow away or something? Mark had quickly adapted his life around making the chance of discovery as small as possible which meant doing things like this, but also giving in to the orders he got. The more he did so the more he felt trapped, but by now it just kind of came naturally to give in. It was just easier.
In his room he barely had time to put the bag away before the speakers came to life. “You know the drill sissy.” Is all the voice said. Luckily he did know, not that he liked any of it. First, he stripped down to his lingerie, then he went over to the way too realistic dildo and gave it a kiss, cringing as he did.
With his new entering ritual over Mark returned to the middle of his room and awkwardly started showing off his new set of lingerie. He felt like such a faggot doing it, Especially alone in his room. It just felt worse some how then when Linda was physically threatening him. Even more so when he knew this would probably be added to his ever-growing site.
He knew the newly added chastity cage was entirely visible with the cut out in his panties, so now was probably a good time to make a comment about it. Afterall with his cage on he wouldn’t be able to jerk off like he had been ordered too anymore and he didn’t want to get punished for it by having those flyers spread after all. Especially not knowing they would lead to his by now probably huge site.
“Uhm, as you might have noticed I kind of have a problem for the rules. My cock is kind of you know.” Mark stammered highly embarrassed and nervous.
“Your cock? Don’t you mean your little clitty which I can obviously tell is neatly locked up? I know the owner of CC’s called me and will send me the key. She also told me that she has shown you how you can still masturbate so I don’t see any reason why your clitty cage would be a problem.” Came loud over the speakers. “Oh and she also told me that she taught you some poses so why don’t you show me those sissy? I’m sure they are better than your pathetic fumbling you call showing off.”
Mark was stunned. For a moment he just stood there frozen, lost for words. He knew his two main tormentors had at least had contact before and knew off each-other, them being Linda and the one who had orchestrated all off this. Mark still had no clue of who that was, and Linda surely wasn’t going to tell him.
What he hadn’t know however was that they actually talked, and quite a lot apparently considering that all this had happened not even an hour before. What else had they been discussing? Could Linda be the one actually behind of all this. It seemed unlikely considering how far from his house her shop was. She did seem to have a thing for sissies, getting off on the whole breaking, but it seemed even more unlikely that she would have been at his house in position too take that sharp of a pic in the few minutes he had been wearing panties or that she would have a daily pair of dirty boxers available for him. It almost had to be someone from the neighbourhood, but who? They all hated his guts.
He did have an idea who it might be, but he certainly hoped he was wrong on that one. He certainly hoped it wouldn’t be John that perv from next-door. His asocial behaviour and the way that no one really knew anything about him together with his sloppy appearance and the fact that he was over 50 years old and a slob had quickly granted him the reputation of pervert. No one really knew thought and it certainly wasn’t like Mark could just walk up and accuse him of anything. He had to be certain or he would be in even more trouble.
Right now however Mark didn’t have much time to think about those things at all. He knew he had to strike the poses he learned, or he would be in big trouble and so with a bright red face he did just that, knowing that he would end up on the website posing in his new lingerie like a, well like a sissy. He had no idea who was looking at him and for all he knew it could already be a couple thousand people. After all there was no way to know if his website hadn’t been spread already, well if it was then his phone would have been buzzing so he counted on it still being a secret.
“Oh my fucking god she really did teach you some poses sissy.” The voice over the speaker laughed. “Well whenever I tell you to show off this is what I expect out of you. Now go on and do whatever, but don’t forget the rules sissy. Bye bye and enjoy your day.” Was heard before the speaker went silent.
Once again Mark was too stunned to get moving right away. Things had really spiralled out of control, but by this time he was so deep in this mess that he just didn’t see a way out anymore. The only way forward he saw was going along and hoping that the person behind this would grow bored of him.
Despite his shock Mark couldn’t wait too long to get out of the house though. He was afraid that if he did that the person controlling the speaker would find something else for him to do and that was the last thing he wanted.
As fast as he could Mark got out of his new lingerie set, leaving only the panties on before getting dressed in his normal clothes. After checking out that everything was hidden well enough he kissed that awfully realistic dildo goodbye and went off to the skatepark.
Just like yesterday Mark was nervous at first, but when no one really seemed to notice he relaxed. All in all, he had a pretty awesome day. He felt normal again for a change.
He was just about to head home when the disaster struck though. Before he could leave his girlfriend, Lisa grabbed his hand and pulled him along to her house right next to the skatepark. Normally he would have loved to go with her but this time nerves were coursing through his body. What was she planning to do? Normally they just made out a bit at most, but what if she had other ideas this time? He didn’t know but the thought alone was enough to make him panic.
“Uhm Lisa, I am really sorry, but I really need to get going, I have uhm something important I need to take care off at home and well now really isn’t a good time. I love you, but can we please do this some other time because…” Mark stammered awkwardly, but he got cut off by a deep aggressive passionate kiss from Lisa. She was always the one to force her tongue in his mouth and this time wasn’t any different.
“Stop Stammering like an idiot Mark, I know you have nothing to do for the next couple of months. It is summer break after all. Now just go with the flow, I promise you are going to love this.” Lisa said confidently with a wink pulling Mark behind her up to her room without giving him a chance to complain further.
Lisa was like that, once she put her mind to something there was no stopping her. Usually Mark just went with the flow, but this time he remained worried. After all she said he was going to love this. He could imagine a few things he would have loved doing with Lisa, but pretty much all of them involved getting naked and right now that was the last thing he wanted.
Once in her room Lisa pushed Mark on the bed and jumped him, straddling his lap and making out passionately with him. It was clear that she was up for something sexy, especially when Lisa started pulling off her hoodie and T-shirt In one motion revealing her perfectly shaped young breasts to him.
Mark was stunned this was one of the first times he actually saw them in person and they were every bit as gorgeous as on the countless of pics he had had. At the same time however it was a very worrying sing. Whatever Lisa was planning he hoped that it wouldn’t require him to get naked as well, especially now that he felt his cock straining painfully within the cage reminding him of just how bad his predicament was.
“L…look Lisa, we really…” Mark tried again but once again Lisa interrupted him with a passionate kiss.
“I know you are probably nervous baby, but I also know that you must have been looking forward to this very moment for a long time. After all I do know that I can be somewhat of a tease, and I was curious to see if you would stick around. As far as I am concerned you have earned this. Now let’s see if it is only your beard that has been taken care off, shall we?” Lisa asked with a playful wink.
With a swift motion she pulled Mark’s shirt and hoodie off. Using a feather light touch Lisa then started running her finger tips over Marks chest. “Hmmm nice and smooth, I really like this new direction you have decided to take. Keep it up tiger.” She said before giving Mark a hard shove in the chest making him fall back on the bed from his sitting position. Placing her hands on his chest for support she leaned in for another kiss.
“Enjoying this so far baby?” Lisa asked getting off of Marks lap to strip out of the skirt and tights she was wearing. She didn’t wait for an answer, instead pulling off the blue and white striped panties she was wearing, revealing her pussy with it’s neatly trimmed landing strip.
Mark was in awe looking at his girlfriend in all her naked glory, god she looked hot. All it caused however was more pain for his cock as it tried to grow hard in its tiny cage.
Seeing his expression Lisa just smirked. “You know with a look like that you don’t even need to answer my question for me to know that you are in fact enjoying this. I bet you are so glad that I did pull you along instead of letting you go home right? I have honestly been looking forward to this for a long time myself.” Lisa said teasingly.
Picking up her panties she held them open and sat down on top off Mark’s lap again. “You see this? This is how fucking wet you made me, just thinking about what we are about to do has caused all of this.” Lisa said pointing out the soaked crotch of her panties.
“Now that we are on that subject I kind of wonder how hard you are, my bet is hard as a rock.” Lisa teased looking up at Mark with a seductive smile. She dropped down on her knees in front of him and her hands shot forward to his belt.
“Noooooo!” Was all Mark managed to get out, but it was too late. Within the blink of an eye Lisa had pulled his pants down to around his knees and she was now staring right at his panty covered crotch, the one with the awful panties that put his chastity cage on display with their hole in the front.
Neither of them said anything for about a minute. Mark was simply to mortified and scared. Lisa on the other hand was just to shocked and confused to say anything.
In the end Lisa was the first one to start talking again. “What the fuck?!” She says calmly at first, still to shocked to really figure out what to say, but once she does all hell breaks loose.
“What the actual fuck Mark, what is this supposed to mean? Panties really? I mean can you even call this fucking monstrosity a panty? What the hell is wrong with you? I mean like honestly, I have no words for how fucking pathetic this is!” Lisa screamed at him.
Mark opened his mouth trying to mutter an excuse but even before he got as much as a sound out Lisa cut him off. “I don’t want to hear a fucking word from you, you pathetic sissy!” Lisa screamed, and Mark shrunk away. He was really screwed right now, being discovered had been his worst fear ever since this had started and it was every bit as bad as he had imagined it.
Tears welled up in his eyes and he was unable to hold them back as the first ones rolled down his cheeks. He was certain this was the end of his very first relationship and that while he was meant to get lucky just now. How had he ever ended up in this cruel situation?
As if the knowledge of losing his girlfriend wasn’t bad enough he had yet another problem. Who would Lisa decided to tell. As angry as she was Mark really started to fear that she would tell everyone and then some. He was pretty much certain that his life as he knew it was over, but then again hadn’t that been the case for a while already?
“Like honestly, as if having a panty wearing faggot for a boyfriend isn’t enough. Just look at those. What the fuck is that perverted thing in the middle even?” Lisa asked grabbing the pink metal of his chastity cage, an instant look of surprised shock crossed her face as she looked up at him in disbelief.
With a swift movement she pulled down his panties getting a better look at the tiny pink metal cage sitting underneath the pastel pink heart shaped patch of pubic hair with the initials MJ in it.
The sight only made Lisa angrier. “I fucking thought you were a huge perv for wearing panties with such a,… such a tasteless design yet you managed to surprise me with just how bad it is. I mean what the fuck, having a special hole so you can show of your pathetic tiny caged cock. What kind of guy even locks away his cock?”
“Then I am not even speaking about that pubic hair or whatever the fuck you call that. Honestly, where did you even find a place that does such things? How does something like that even come up in your mind? God you are such a fucking pathetic sissy.” Lisa carried on.
“How long have you been doing this stuff behind my back? I mean given how you wear such obnoxiously sissy panties and that under your clothes in public it must have been for years. How could I have been so blind, and to think that I dared you to wear a pair of my panties just a week or two back thinking it was a ‘dare’. I bet you fucking loved that.” Lisa raged without knowing it pinning down the moment that had set all of this in motion. It just made her words sting even more.
Mark knew better than to try and interrupt her again however. He knew it would make her angrier and maybe if he just let her rage till she was done he would be able to talk her into keeping his secret. He knew it was unlikely, but still he had to hope.
“A fucking chastity cage, do you want to stay a fucking virgin or whatever your reason for wearing something like that is?!” Lisa asked taking a closer look at the thing.
“CC’s boutique? You mean that weird overtly sissy store in the city? I always wondered how a shop like that could exist, well I guess I have my fucking answer now. What the hell does this ‘property off’ even mean? You don’t mean to tell me that you don’t even have the key do you?” One look at Mark’s overtly embarrassed face told her everything she needed to know. Lisa didn’t start raging again though. She just let out a deep disappointed sigh.
With a moment of quietness Mark grabbed the chance to plead with Lisa to keep his secret. “Please, I know you’re mad, but please don’t tell Anyone about this. I beg you.” Mark said pathetically, tears still streaming down his cheeks.
Lisa just looked shocked. “Really? You come into my house. I have to find out how much of a pathetic sissy pervert you are, and the only thing you are worried about is saving your own skin?! Get out of my fucking house you pathetic argh! Get fucking out.” Lisa screamed in anger and frustration, Mark’s reaction making her even more pissed.
“But…” Mark started to stammer.
Lisa was quick to cut him off however. “Get out!” She screamed at the top of her lungs.
After the second get out Mark just hung his head and gave in grabbing his clothes and moving out of Lisa’s room. He felt terrified, completely humiliated and just overall dreadful. The two weeks of torment had really turned him in even more of a pushover than he had already been, and it clearly showed.
He closed the door of her room and got dressed before slumping back home. Mark felt so lost he really had no idea what to do. He felt like his whole world had just fallen apart. Things were just feeling so empty somehow.
While Mark was gone Lisa was still fuming. She hadn’t really thought about telling people, not at first at least. After Mark only seemed to care about himself however she thought about doing it just out of revenge.
On the other hand however, as mad as she was there was still something weirdly arousing about it. She hadn’t dared Mark to wear panties out of the blue after all, and if she was honest to herself she knew she had chosen Mark for his slightly effeminate looks and the fact that he was a bit of a pushover. Pushing him around just made her so hot.
In fact now that she thought about it she hadn’t really been mad about the panties and such either. She was mainly mad that Mark had kept things from her for god knows how long. Of course part of her reaction was also due to the shock of finding out so unexpectedly.
Now that she really thought about it though she started to feel like there had to be more about this than what it seemed. The panties of choice were rather extreme and honestly so was the rest. It just didn’t stroke with the Mark that she knew. He always tried to be as manly as possible. It was one of the reasons she had dared him with those panties, she just loved seeing him embarrassed.
She was pretty certain he still felt that way, after all he had been genuinely embarrassed this time as well. The Mark she knew would never wear something like that, he especially wouldn’t let anyone lock his cock up. Not voluntarily at least, he was way to horny to do so.
There had to be more behind it and honestly that maddened her even more. Mark was her boyfriend, her pushover and she would just let anyone take him from her. She was going to find out who was behind this, and she was going to reclaim her boyfriend. He was hers to toy with.
At least she had a clue to go off. Afterall didn’t that chastity cage come from CC’s? Maybe whoever owned that store would know more, like maybe who the person buying these things or accompanying her boyfriend was. It was certainly worth checking out and so she put her clothes back on and went on her way into the city.
The entire bus-ride long Lisa kept going over what she was going to say and do once she got there. She would have to make it very clear from the start that she was not one to be messed with. Whatever it was that they did to her boyfriend had to be forced in one way or another, and that was illegal. Maybe she could use that to her advantage somehow.
When the bus pulled up right in front of the store Lisa saw the tall redheaded storeowner was headed to the door, a young pretty girl with a shoulder-length bob-cut walking behind her. Without hesitation Lisa pushed open the door and blocked the entrance much to the shock of Linda. Stephanie on the other hand looked positively frightened.
“Who the hell are you and what have you done to my boyfriend Mark?! There is no way in hell he would wear what I caught him in on his own accord and I am pretty sure forcing him is illegal. So either you tell me everything right now or my next stop is the police station!” Lisa screamed at the tall woman who’s face went from shocked to nervous.
Linda knew that she would get out of a real sentence, after all she could afford the best lawyers and whatever fine they might settle for. It would probably mean that she would lose her store thought and that was something she absolutely wanted to prevent, especially now that she had her first client. A client she didn’t want to lose either. The first one was always the most important. After all it was the only way to build a reputation. Especially on such a niche market.
More even, if they did a proper investigation they might find out about Stephanie as well and then she could really lose everything. Her personal servant and all her money. Damn it, this stupid girl could ruin everything she had build. She really had to deter the girl somehow.
In a way Lisa reminded her of herself when she was younger, the girl was confident, smart and determined. The fact that she actually took a boyfriend like Mark, who was a wimp even the first time Linda had met him also told her that Lisa might even share that interest with her. It was probably best to come clean with this girl. Maybe she could even make a friend and an ally out of her. In fact Linda was confident she could. She had a lot of people knowledge after all. In an instant her nervous look disappeared and got exchanged with a cheeky smile.
“My name is Linda, I am the owner of this store and yes, your boyfriend Mark is a client of us. You are right that he doesn’t come here voluntarily. I have also helped push things a little further, but if you are honest with yourself I am certain you know he was just a sissy waiting to happen. He just needed a push. If I had to guess you might have even liked what you saw. Am I right?” Linda asked. The last part was a bit of a gamble, but she remained confident.
The shock on Lisa’s face told her she hit the nail on the head. The girl went from angry to somewhat shocked and defensive even. “That’s not true, he is my boyfriend and what you are doing is wrong.” Lisa replied quickly more on the defensive.
“Oh but I think it is true, and yes it is wrong. At least it might be, cause honestly he is a wimp and a pushover, he needs a strong hand to guide him. To turn him into the sissy he really is. You have probably even been toying with the idea yourself. I mean you can’t tell me you have never thought about what he would look like in panties right?” Linda answered.
The sudden flustered look on Lisa’s face told her everything she needed to know so she carried on. “Don’t worry, it is nothing to be ashamed off. In fact I am very much the same, the world needs more women like us, women who can spot a sissy and push him in the right direction. Isn’t that right Stephanie? Why don’t you show our guest exactly what I mean?” Linda said.
“Yeth mommy.” Stephanie lisped much to the surprise of Lisa, she had always been somewhat bi and she thought Stephanie was very attractive. She wouldn’t have minded having a girlfriend like Stephanie. She was somewhat shocked to hear such a silly voice out of such a pretty girl.
Her shock only grew when the girl blushed brightly and raised her skirt right there. She wasn’t wearing any panties so the tiny chastity cage she was wearing was in plain view. Linda had only just put her in a way smaller cage, after Stephanie had decided to put Mark in the smallest cage that would fit.
Just like Mark Lisa couldn’t believe what she was seeing this pretty girl was actually a guy? It just seemed so surreal. “Stephanie used to be called Stephen but now as my sissy stepdaughter that name doesn’t really fit her anymore.” Linda smirked. She had seen how Lisa had looked at her with a twinkle of attraction earlier and she just know it would only help her drive her point home further. Now that she saw how pretty a sissy could be it would be easier to convince her.
“You see, I am sure Mark can be just as pretty. He really is perfect sissy material, I mean you must have noticed as well how effeminate his body actually is. He even has a pretty face.” Linda smirked.
“That might be true, but he is mine and you have no right to just change him.” Lisa said now a lot calmer and more agreeing.
“You’re right and I’m sorry about that. I swear I didn’t know he had a girlfriend. Honestly though can you blame me for that? No he got send here by someone else who managed to snap some pics of him wearing a pair of red panties a week or two ago I believe.” Linda said.
Lisa was in shock, without really realising it she had been the cause of all of this. She didn’t really know how to feel about it though. On one hand she felt kind off bad but on the other she felt somewhat excited as well. Something about pushing Mark around was so hot. She still felt bad for thinking so, but she just couldn’t help it. Especially after seeing Stephanie. Lisa knew she was into boys and girls. There was something special about this hot girl being a guy in reality, a very submissive and easily embarrassed girl.
A girlfriend like Stephanie was like a dream and Lisa really wondered if Mark really could become that pretty. Now that Linda had mentioned it she couldn’t help but wonder. “Okay, I have decided to go along with this for now and keep from going to the police. This can change at any moment though and there are conditions to my silence. Before that however I believe you know who is really behind this and I want you to call that person to come here right now. That is my first condition.” Lisa said firmly.
Linda just smiled and nodded her head before going to the phone. She already liked this girl, strong, very dominant and from the looks of it very interested as well. Linda didn’t really like to be blackmailed or told what to do, but it saved her skin now and she had a feeling that she and Lisa might actually become good friends. Besides mentoring a new dominant woman might also be a fun and fulfilling project.
“Oh hey John, something very important just came up. Apparently Mark has a girlfriend and she is right here at the store right now. She knows all about the blackmail, and your website. She threatens to go to the police, so I think it is in your best interest to come here now.” Linda said putting down the phone before John could answer.
Returning back to where Lisa was eyeing up Stephanie with a smirk Linda said. “So I think he is coming right over in the meantime why don’t you follow me? I want go show you some extra advantage of having a sissy.” To conclude her sentence Linda winked.
Lisa had been so pissed when she came here. Now she was pleasantly surprised though, somewhat amused and a bit excited. Linda was a real bombshell, the definition of a milf if she had ever seen one, and Stephanie well Stephanie was gorgeous and perfect girlfriend material. Stephanie made her realise that while she thought she was bi she was mainly into sissies. Well she never liked manly men. One thing was for sure she was curious what Linda would show her. Whatever it was she was excited about it and so she followed along.
In the meantime, Mark was just arriving home. He had gone to a park nearby after the emotionally exhausting evening with Lisa. He just didn’t have the courage to deal with the person behind the speaker right after the confrontation.
Like most days Mark found another brown envelope, he already knew what would surely be inside. He just picked it up with a sigh and went straight to his room. He kind of expected the speaker to instantly start up, but it didn’t. Either-way Mark went over to the dildo and kissed it. Lisa would probably tell all his friends but having his number and website out at gay bars would be so much worse still. For now he hadn’t had texts from any man or any of his friends which was a good sign he guessed. He did know that could change at any moment though but until then I was probably best to just go along with the demands.
He stripped out of his clothes and put his lingerie back on again. Mark was feeling tired already even-though it was still early evening. All those intense emotions had really taken their toll. As soon as he had put on everything the right way he got into bed.
Mark knew what he needed to do and he had been dreading this moment ever since he knew it was still a requirement to masturbate even-though he was locked up. Fingering himself or having anything up his butt for that matter was the last thing he wanted. Linda’s fingers had been more than enough butt stuff for him, more than he had ever imagined himself having in his entire life.
Yet now he was pulling the lube out of his nightstand. It brought back painful memories. He had originally bought the lube as soon as his relationship with Lisa was official, thinking sex would follow soon. It had never come to that though. Today would have been the day but instead it was one of the worst moments of his life. He could still barely grasp the fact that he was single again or that soon all his friends would know about the sissy panties.
Instead of losing his virginity today he had lost his cherry and now he was lubing up his fingers to finger-fuck himself to climax yet again. Slipping one well lubed finger up his butt was easy. Actually getting off would be another matter he feared. With a sigh he grabbed the freshly worn boxers of his tormentor out of the envelope and pulled them over his head.
Nearly instantly his cock was straining painfully against its tiny pink prison, another reason why he had to do this, if he ever wanted out of this damn thing.
To Mark’s surprise the finger in his butt actually felt surprisingly good already. He didn’t really notice that it had started feeling good when he Pulled that boxer over his head. That strong smell of unwashed cock and stale cum was by now so deeply linked with arousal in his mind that it worked like a strong aphrodisiac.
While working his finger in and out of his bum he quickly found that special electrifying spot that felt so good for some reason. Unlike Linda’s skilful fingering Mark went straight to the finish, focusing all his attention on that special spot until only a few minutes in he exploded. Just like with Linda earlier his orgasm was intenser than any he had had while stroking his cock. So much that he needed to catch his breath for a couple of minutes afterwards.
When he finally did manage to catch his breath, he pulled the boxers off of his head and gave the dildo a kiss before quickly falling asleep. At least the voice over the speaker hadn’t bothered him which was a small relief.
Maybe the one doing all of this to him was finally growing tired of him? It was a good sign at least, or so he thought. Little did Mark know what was happening at CC’s right at this very moment.
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