Part 9

Chapter 10

While Mark was going through his night time ritual and sleeping Lisa was at CC’s getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The though of it being a guy who was locked up and frustrated was even better.

If she had any doubts before she was sure now. She wanted a sissy for herself. Even if Linda had told her that she could come by any time she wanted. She kind of wondered just how pretty Mark could become. One thing was certain she was going to see to it that he got as pretty as possible.

Lisa was just screaming through another orgasm when John came in. It was her fourth in the short time they had had to wait on him. “Alright sissy stop!” Lisa commanded pushing Stephanie away with her foot on the sissies chest. She got up and ordered. “now put my panties and tights back in place.

While Stephanie did as she was ordered John simply stormed towards the two women. He himself had never realised Stephanie was in fact a sissy. It gave him an instant hard-on. He had seen over the weeks that a guy like Mark could get him worked up much to his surprise, but that they could be such a hot piece of ass was new to him. Oh god how he would love to abuse a sissy like that. It had been looking to ruin Mark’s life, but now he cared more about getting himself the perfect obedient girlfriend he had always wanted, and this stupid blond was ruining everything.

“Who the fuck do you think you are?! You have no right to fucking blackmail me you bitch, and I won’t have any of it. Things were just getting juicy damnit. He was just getting home and was about to finger himself when you…” John screamed angrily, but he got cut off by Linda. Lisa didn’t look all too worried or phased about John’s outburst.

“Oh please shut your fucking mouth and listen John, you might even be interested in what we have to discuss!” Linda retorted shutting John up, but it was clear he didn’t plan on staying that way for long. Never the less he was listening now and Linda was sure he would fall in line. At least she hoped so. She had convinced her young protégée that having a sissy was fun, so she would get to keep her first client, but they hadn’t discussed what to do with John yet. Either way was fine for Linda, working with Lisa would be way more fun anyways.

Now that everyone was silent Lisa took the word. “John, you are the one who has no right to blackmail my boyfriend. Turning you in would only be my civic duty. I am not here to take Mark away from you though.” Lisa said both to the surprise from both John and Linda.

“I mean you have done a pretty good job off sissifying my boyfriend up until now, and you may continue to do so. From now on though your game is played by my rules. Before you object I am not that strict. Every big change should just be run by me first. I will most likely approve, but I need to know. Also, I get to make demands for changes and you will be the one forcing them on Mark.” Lisa explained gaining a genuine interest from both Linda and John who suddenly didn’t think this would be so bad anymore.

“In the mean time I will play the understanding girlfriend. I will act like I know no better than it all being his idea. I will just be supportive of his new choice in life and help him live the life that he ‘wants’ or at least I will act as if that is all I am aware off. Also I heard you made him a website that’s still private? Well I want full access and give Linda full access too if that isn’t the case yet. I will be spending a lot more time in Marks room and if I am in the picture you should always make me unrecognisable or I will go to the police anyways. Is that a deal?” Lisa asked firmly enjoying the way in which she had really shut John up.

John thought about Lisa’s offer. He didn’t like that he would have to ask permission for his actions. At the same time, it didn’t sound like Lisa would be denying permission either, so it sounded more like it was informative. He could work with that if it meant he would get to continue the sissification of Mark as he had been doing so far. Lisa saying she would be present in Marks room was a big bonus as well. The girl might be a bitch, but she was a hot bitch. Getting to watch her too would be way better than just toying with the sissy.

“Alright, we have an agreement. I will also stay quiet during the times you are there.” John eventually said.

“Great, as long as you keep those simple rules in mind I agree not to tell on you either. You may go now, I still have a few things to discus with Linda. When you get home, you give us access to that site first. I will be in touch with you.” Lisa said dismissively, and John just walked away. He didn’t like having to listen to a woman much less to a girl, but he didn’t want to lose his sissy either or be in trouble.

Linda just smiled the girl was a natural and she was very much going go enjoy mentoring her. Within a minute Stephanie was back between Lisa legs as she and her stepmother worked out how they saw the mentorship. Linda also gave Lisa a few tips on how to handle Mark now that he was aware that she knew his secret. They exchanged phone numbers, Johns number as well and parted ways.

They both were excited about what their future would bring. Surprising Lisa, Linda kissed her full on the lips. A passionate kiss, waiting for the girl to allow her tongue in. Nothing like the aggressive kisses she sometimes gave a sissy to let them feel who was boss, and even those kisses were rare when it came to sissies. A good sissy should only ever kiss a pair of pussy lips. A real kiss unless it was with an unsuspecting man or another sissy was a huge privilege.

It didn’t take Lisa long to give in to the Kiss and even return the favour. She had always been somewhat into women as well, and Linda was a real milf. This show of lust for her only made Lisa feel more excited over what this partnership would bring. With the kiss over they parted ways.

At home Lisa exchanged a few quick messages with John who apparently already had a few requests. There was nothing asked she was opposed to. In fact she looked forward to seeing them carried out, especially after going through the website. The only demand she had was to cut the live stream on the website when she was there. John would still be able to view it, but if the website ever did gain members then they wouldn’t be able to find out her identity. With the discussion over, she finally went asleep, excited over what this adventure would bring.

Chapter 11

It was early morning when Mark woke up, it wasn’t because of any alarm or that he was well rested. No, it was the pain of his cock trying to get hard within its cage that caused him to wake up with a loud grunt. His heart instantly sank as he remembered what had happened yesterday. He hadn’t heard from Lisa again and he was terrified. He just hoped that she would forget about everything somehow. One thing was certain though he wasn’t going to try and make contact since he was too scared.

He also had his own problems to deal with like executing his morning routine. Something that had become way worse after yesterday’s events.  No longer was he able to masturbate. He had to finger his ass, it was the only way he could get off much to his shame.

Mark still felt the same when it came to butt stuff, it was only okay if he could stuff his cock in a pretty girl’s ass. He had never thought that he would get something in his own ass, even less so that he would be able to cum from it yet he had done so twice already, once with his own fingers and once at the hands of Linda.

To think that Linda had been like his wet dream come alive. How could she ever respect him after he came under her foot and with her fingers up his butt? It didn’t really matter, she had never respected him, and he knew it. He had never been anything but a sissy in her eyes.

Despite how much he despised the idea Mark was starting to think off himself as a sissy as well. He was constantly being addressed as sissy, by the voice over the speakers, by Linda, and since yesterday by his very own girlfriend. He couldn’t even really blame his girlfriend, or anyone who would see him now. Afterall he was about to finger himself to another orgasm again.

With a sigh he leaned to his nightstand where he kissed that overtly realistic dildo. Then he grabbed the boxers and pulled them over his head. Instantly his cock started to hurt even more in its cage. The boxers stank just as much as they had yesterday, and yet he was only growing aroused by them.

It was a wicked scheme, the boxers had been linked to sexual release over and over which made it easier to get off with his fingers in his butt. This only further enforced the link between pleasure and that smell while also making him get used to getting off form butt stuff.

Without him really realising it his frequent masturbation sessions where really reshaping his turn-ons. While it wouldn’t make him gay in the sense that it took away his usual turn-ons, it certainly added a few more which to him were disturbing at best.

After yesterdays experience Mark’s finger slid up his butt easier. He was also able to locate that sweet spot nearly instantly and he used it to get himself off in under ten minutes. With the way his cock was hurting it still took some time to get off but all in all he was already growing quite efficient at fingering himself. The orgasms where also more powerful taking him a moment to come back to his senses again.

He wasn’t allowed to do so however as instantly after his third in a series of probably countless anal orgasms the speakers came back to life. “Did you miss me sissy? I bet you did. I am very glad to see how much you are enjoying playing with your boy pussy though. I knew from the moment I first saw you that you were a sissy slut at heart.” The voice said making Mark blush.

“Anyways, since it is Sunday and the shops are closed you won’t need to go back to the shop to find yourself another set of lingerie, at least not today. This doesn’t mean you get the day off though. I have been walking through the neighbourhood to drop off your new jerk boxers in the usual hiding spot and I have seen that Ms. Prince, one of the local high school teachers has hung her wash out to dry. On her clothing line there was a nice set off satin bed sheets. You are going to steal them and put them on your own bed. I bet you can’t wait to sleep surrounded by satin you little faggot.” The voice over the speaker laughed.

Mark was shocked. It wasn’t like he had never stolen anything before. He had done so for quite a few bets, but it had always been just a trophy to show off to his friends. Never something for himself and definitely nothing that big before.

Sleeping in satin would also just feel so wrong, especially since it was in Ms. Prince’s sheets. She was a teacher in the lower grades and only in her late twenties. She was also smoking hot and the fantasy of probably all boys in their high school. Mark himself had imagined himself in Ms. Prince’s bed on more than one occasion. He had never meant it this literally though.

“I also have a task a bit more long-term for you. I want you to be able to deep throat that dildo by Wednesday afternoon or you’ll be very sorry. How much you train and when you do is all up to you, but you better be able to swallow it whole on Wednesday.” John said over the speakers in a warning tone.

Mark’s eyes went wide, kissing that thing was horrible already. He couldn’t even imagine putting it in his mouth. Maybe he should refuse, after all most of his friends probably knew about his lingerie and chastity cage by now thanks to Lisa. If it was all in vain then what was the point? Well there was still that awfully tight chastity cage he didn’t have the key to he had no idea how to deal with that one yet, but he would figure it out. At least he hoped so. He hadn’t been big on figuring things out so far.

He did have until Wednesday to decide he guessed which gave him a bit more than three days. For now, however he guessed that he could go ahead and steal those sheets. It was something he never had much problems with, so it would buy him some time to think about sucking that dildo.

With a sigh Mark got out off bed and went on to wash his lingerie it would probably always feel wrong, but it wasn’t like it was that new to him anymore. He washed the boxers as well and took a shower before going back in his room and picking out the first panties he got his hands on. They were all overtly girly, so it didn’t really matter that much.

The pair he ended up choosing was powder pink satin with a lace front panel and ruffled edges. While none of the panties from CC’s where really thongs. They all seemed to have one thing annoying in common. They were designed in such a way that they rode up his butt crack and rubbed against his rosebud constantly, something which seemed to be even more annoying now that he was starting to get used to butt stuff, it slightly aroused him despite his dislike.

After the panties he put on his other clothes, covering them perfectly. It was just another thing he was getting used to, and while he wasn’t really planning on being seen by anyone he was still mortified by the thought. Even if people might already know thanks to Lisa.

All dressed Mark grabbed his back pack and headed out, straight towards the house of Ms. Prince. He knew where she lived. He had once been the hero of the school when he had snatched a pair of her panties away and taken them to school. They had and still hung in a semi hidden spot in the boy’s locker-room.

Bedsheets where something completely different though. They weren’t sexy, and they were huge, not just something you snatched off the clothing line and put in your pocket. He was already dreading what he would have to do. If he had to grab them along he would need some time so the risk of getting caught was way higher.

Nearing Ms. Prince’s house Mark looked for the hedge in her backyard that bordered a park. He still remembered there was a spot that wasn’t as overgrown as the rest. A spot he could easily squeeze through to make his entrance and exit.

First though he climbed up in a tree to scout whether or not it was a good time to snatch the sheets. In his tree Mark had a perfect view off all the windows at the back of Ms. Prince’s house. His attention was instantly focused on the one on the right. It was the window of her bathroom and she was just stepping out of the shower.

Mark Watched in awe as he admired Ms. Prince’s naked body. At the same time this awesome sight was a curse as well. It made his cock grow which was just painful in its way too small cage. It was a firm reminder of his current situation and why he was here.

He got his own private peep show watching Ms. Prince dry herself. It was hot, but most of all it was painful that damn cage really was a nightmare. It was so bad even that he was glad when Ms. Prince finally wrapped a towel around her and headed out off the bathroom. He imagined she would go to her bedroom at the front of the house and probably take some time to get dressed.

A few minutes was all he really needed, so he decided that now was as good a moment as any. He climbed down the tree, squeezed through the hedge and went straight for the clothing line. The sheets in question where pastel pink and the satin felt very slippery to the touch. He didn’t have time to waste or hesitate though, so he just pulled them down quickly, jammed them in his backpack and made a run for it.

Mark kept on running until he finally arrived home, while he wasn’t built like an athlete in the slightest he definitely had great stamina. The first thing he did was exchanged the washed boxers for the pair of freshly worn ones, before going right up to his room.

Once in his room he kissed the dildo like he had to and unloaded his backpack and proceeded to switch his sheets for these ones. Mark cringed as he put them on his bed. They instantly made his room look way girlier.

The sheets themselves were made of shining slippery pastel pink satin. Diagonally the name Marcy was embroidered on them in a big elegant fuchsia script. The same was true for the pillow case. He realised that was probably the surname of his teacher. God it would feel so wrong sleeping in them knowing where they came from.

While he did steel things from time to time it was always just as a trophy, never for his own use. This somehow made a big difference at least to Mark. He also felt bad since these sheets had probably cost a fortune. That and he never particularly liked sleeping in someone else’s sheets. Definitely not satin sheets like these which would feel strange either way.

“Good job sissy, I can just see how excited you are about your new sheets. They look lovely and so you. I bet you are going to sleep like a rose in those.” The voice over the speaker laughed at a mortified Mark.

“Now, why don’t you strip down to your panties and masturbate in your new sheets. I am certain you are just going to love it. New sheets or not, you look like you love playing with your butt, so go right ahead sissy.” The voice finally said.

Mark really didn’t want to, but he also couldn’t deny how good fingering his butt had felt. It felt way better than masturbating much to his shame and the peep show he had just gotten had turned him on.

He could try to resist, but at what cost? He still hadn’t had any taunting messages from friends, so he guessed his secret was still safe much to his surprise. He had already done it twice so what would be the point in resisting now?

With a sigh Mark stripped down to only his panties and took the freshly worn boxers out of their bag. Just like always they smelled strongly of sweat and stale cum. He could feel the crusty parts where cum had dried rubbing against his face once he pulled them over his head.

His cock was already straining painfully against its cage, but less so than in the beginning. Due to how gradually this change was going Mark didn’t really notice. he just slipped between his new sheets without thinking anything of it.

The sheets felt electrifying and so very good against his smooth skin. It was strange, he would have never thought sheets could feel good. He also couldn’t shake the thought that Ms. Prince had slept and probably had sex and masturbated between these very sheets.

At any other time that fantasy would stick with him and help him get off but wearing panties and having the strong smell off cock pressed right to his face prevented him from lingering on that fantasy.

Thinking about sexy women mainly caused Mark to feel embarrassed. He was still turned on by them but given his recent experience with women which was pretty much limited to the girls on the bus, Linda and Lisa. He just felt like no woman could respect him. The only thing they did was mock and taunt him. Not that he blamed them, if he saw a guy wearing lingerie he himself would have probably been the first one to laugh in his face.

He had never really done any of that, but he knew that if he had had the chance he would have. In that sense what was happening to him was probably poetic justice.

Slowly Mark slid his fingers in his bottom. Once again he was surprised by how strangely good it felt to do so. When his finger rubbed over that special spot he felt waves of intense pleasure course through his whole body. It was such a strange sensation, way intenser than just pleasuring his cock.

In a few minutes Mark was moaning softly, obviously feeling very good sniffing those worn boxers as he slowly drove his finger in and out of his bottom. It was clear that once the pleasure took over he didn’t seem to mind, and it was perfect.

John sat there behind his computer stroking his cock to this girly who was fingering his butt on his command. It was hot, oh how he wished he would be able to drive his cock deep down Mark’s ass some time. He could already imagine how tight the guy would feel.

Now he just needed to convince Lisa to let him do just that. He really hoped that bitch wouldn’t be to much a pain in the ass. John grinned thinking about it. If anyone was going to be a pain in the ass it would be him being a pain in Mark’s ass.

Another thing this moment was perfect for was some more blackmail material. After all what image screamed more that Mark was a sissy faggot in desperate need of a cock than they guy fingering his own butt moaning with pleasure while sniffing a dirty pair of boxers.?

If this image got spread in the right place the message would be very clear and there would certainly be someone who would take action. After all, as a straight guy himself even John had to admit that he would love to take action. If only that stupid girlfriend didn’t have him by his balls.

When it would come to it, if it ever would come to it. John would make sure to throw everything he had on that little shit out in the open. If he would be going down, then so would Mark. He was going to make sure of that.

For now everything was okay though. Lisa even seemed enthusiastic about what he had planned. Which was at least a step in the right direction.

John’s attention got dragged right back to his screen as the moans were suddenly getting faster in pace. Until finally a squeal escaped Mark’s lips and a darker pink spot appeared in the front of his panties while Mark lay there panting through the boxers.

“God sissy, creaming your panties like that. You must really love it up the butt, or is it the smell of my cock you like so much?” John taunted through the speaker, laughing as he saw the look of horror on Mark’s face when he pulled the boxers off his head.

“You know I have changed my mind about giving you complete freedom over when you train that mouth of yours to deep throat. Well you can still mainly choose, but I want to see just how far you can stick it already. Seeing how big of a faggot you are, I wouldn’t even be surprised if you could already deep throat that dildo.” John mocked.

Mark couldn’t believe it. He wasn’t a fag and kissing that thing was horrible enough. He had thought that he would have time to decide wether to do it or not, but apparently that wasn’t the case anymore. So, what should he do?

Eventually he came up with a weak protest. “But you told me I could choose when I sucked it as long as I could deep throat it by Wednesday evening.”

“Yes, I did, and now I have changed my mind. Are you trying to talk back to me sissy?” The voice in the speakers came threateningly.

“N…no, it’s just not fair and I, please don’t make me do this. I beg you.” Mark stammered pathetically. His reply had been nearly instant. With the blackmail and the possible consequences constantly on his mind he had really become even more weak willed. Even to an extend where the question wether he was talking back frightened him to no end.

“Well if you are not talking back then I figure you still want to be a good obedient sissy. Good obedient sissies follow all orders without hesitation. Oh and your begging isn’t very convincing at all. In fact, I am convinced I am even doing you a favour. I mean you might be telling everyone you don’t want to do all of this, but if that had really been the case then thing would have never gotten this far. No I believe you wanted this all along regardless of what you say.” John said feeling Mark’s weakness and exploiting it to push him even further, making him second guess wether he even really hated this.

After a couple of weeks of constant blackmail and worry it really wasn’t that hard anymore. Mark had become pretty easy to manipulate and his embarrassed silence said enough. John could see that he had managed to plant a seed of doubt from the way in which Mark just stayed silent in shock.

“So, what are you waiting for sissy? Are you going to start sucking that dildo like a good sissy or do I need to start spreading flyers? Do you know the “Leather Bikes”? They are a gay sister branch of another biker’s club, and they definitely aren’t to be messed with. They might be gay, but I can assure you there are no limp-wristed faggots like you in that club. Unless maybe as a club bitch which I am sure they can use more of.” John said frightening Mark to his core.

It ended up pushing Mark over the edge. John’s earlier taunts had gotten him to doubt whether this really was wat he wanted or not. He was still convinced he hated it but there was a seed of doubt and now his abject fear once again pushed him over the edge.

With a shaking hand he reached for the dildo, once he was nearly there he pulled back slightly. Hesitating for another moment, before he finally extended his arm and grabbed the dildo firmly. Just taking it in his hand was enough to make him shudder. The only difference he could feel between the dildo and his own penis was that the dildo was colder to the touch.

Well of course it also wasn’t caged, way bigger and constantly hard. Apart from that it felt like a real penis for all Mark could tell cause he only ever had contact with his own.

“That’s it, that’s a good sissy. I knew you wanted it. Doesn’t it feel good to have such a huge cock in your hands? I bet it is eye opening cause honestly that clitty of yours really doesn’t count now does it?” John laughed taunting Mark further. Now that he had pushed the guy into sucking it he might as well further exploit it to reinforce the doubt he had planted.

“Kiss the tip, then slide your lips around it and let’s see how far down you can swallow it.” John said. When Mark didn’t instantly respond John knew he needed a little extra push.

“I am going to count to 10. If I don’t hear you either gagging loudly on that dildo or see it disappear in your throat completely I am off spreading those flyers. ONE!” John said. He loved toying with mark like this. The guy was just so susceptible to it.

John already knew what the outcome would be, that much had become clear during the time he had started blackmailing Mark. The question wasn’t really if he would give in. It was rather at what count he would do so. “TWO”

Mark still kept strong and didn’t actually move closer to the dildo. It was kind of amusing to John honestly, but he also wanted to see action. “THREE, FOUR, FIVE, SIX.” He suddenly counted in rapid succession making Mark panic and shove the dildo in his mouth as far as it would go in an instant.

He didn’t even really think about it, he was just scared that at that rate he wouldn’t make it before the voice on the speaker reached 10. The quick forceful way in which he had pushed the cock down his throat really hurt, it also made him gag rather violently and while it felt like he had pushed the cock as far as his throat was deep he hadn’t even made it to the half way point.

The dildo had felt every bit as gross as he had imagined it. The silicone felt so lifelike and it also warmed to the touch rather quickly. He could even feel the veins and the wrinkles of the fake foreskin underneath the head. The dildo was really made with gruesome detail and he felt like he just wanted to throw up.

It also brought some worries along, like how the hell was he supposed to be able to deepthroat that cock by Wednesday. It was just impossible, or at least it felt that way.

Mark didn’t get much time to worry though. He was surprised by the sudden sound of the front door opening and his mother calling upstairs. “Mark Lisa is here, I just told her you were up in your room.” She said, and he could already hear the footsteps coming up the stairs.

An intense wave of panic washed over him. Lisa had only just been so mad at him and now she was almost at his door while he was laying between his satin sheet in nothing but a pair of frilly cum soaked panties and a very lifelike dildo in his hand. How the hell would he ever be able to explain all of this?

(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)