Chapter 5

At least he didn’t have to wait long for his bus to pull up. Not that it helped with any of his suffering. He vowed right there that he would never visit that store again. There were few people on the bus and yet he felt like all eyes were on him. Passing two girls his age at front he heard some whispers. “What the fuck, I never thought that store would ever have an actual customer.”

“Look, he is even wearing a bra, and oh god are those stockings?” The other girl gasped surprised as he passed. Mark decided it was smart not to pass any more passengers, so he sat down a couple seats past the girls. Only then did he have the idea he could fold the bag and hide it under his shirt. It was quite a thick package when it was finally folded small enough, but it was better than having the bag on display.

This had to be the worst bus ride of his life. Sitting down had caused his pants to rise slightly. The girls kept busily whispering and snickering. Undoubtedly about him, and his tucked penis was growing very uncomfortable in its panty prison. The satin and nylon fabrics just felt so sensual on his smooth skin that it made his cock want to grow. Which was especially humiliating since the strong taste of cum, evidence of his two orgasms was still strong in his mouth.

Luckily none of the passengers further down seemed to notice him. It had only been the girls by the time his stop came up. Nearly running past the girls, he got off and ran to his house. He was so fast that he nearly didn’t notice another box sitting on the porch. With a feeling of dread, he picked it up and went straight to his room.

Once there he let out a deep sigh, but there was no time to gather his thoughts as the voice nearly instantly spoke up.” Have you, bought what I asked yet? I believe I don’t have to remind you of the consequences of what happens if you don’t have it by tonight right?”

Was his blackmailer waiting for him all this time or what? Unbeknownst to Mark John had just programmed the webcams to give him a ping whenever they spotted motion after a period of seeing no motion at all.

“I…I have bought it already, please don’t spread those flyers.” Mark Spoke up in a scared voice.

“Alright, then Let’s have a look shall we. Put on your lingerie, and I hope I will like it or you’ll have to go out looking for something else.” The mechanical voice warned.

Terrified Mark removed his outerwear leaving him only in the embarrassing lingerie. John couldn’t believe his eyes. He would have guessed Mark would have gone for something a little more normal, but this was perfect. The guy actually looked rather sexy. His long hair was still a mess which took away slightly from the look but other than that he actually looked pretty cute. Cute enough to make Johns cock stir.

John couldn’t quite figure out why Mark had worn this lingerie under his clothes though. He had guessed the guy would have done anything but that. Like when he checked over and over in the mirror when he had to wear panties. There was probably reason, but for now it was a reason to push Mark a little further.

“What a sissy you are, you couldn’t even wait till you were home to try on your lingerie? Well since you seem to like lingerie so much you’re forbidden from wearing anything but panties ever again.” The mechanical voice said leaving Mark stunned in his new lingerie set.

“Wait, no please. I didn’t mean to wear …” Mark replied, but he got cut off immediately by the mechanical voice.

“Shut it sissy, that wasn’t a question and it is not up for bargaining. You know it has always fascinated me to see how careless kids these days are with their personal information. I mean I am on your Facebook right now and I can simply pull the names and email addresses from every person in the photo titled “group pic” apparently you and some other people at the skatepark. You know these tags really make it easy all I have to do is copy paste a bit and I am ready to send a link to the website to every single one of them. That is of course unless you changed your mind.” The Mechanical voice concluded.

Mark looked as pale as a ghost. That picture was one with all of his closest friends. He would never be able to live that down. Besides standing here in the middle of his room in nothing but frilly lingerie, talking to a wall didn’t really make him feel courageous at all. This was all temporary, he would figure a way out, he was certain of it. Mark tried telling himself.

Eventually he just slumped his head in defeat and gave in to whoever it was that controlled the voice in his room. “O…okay, I’ll do it. Only panties from now on.” Mark said softly.

“I knew you would change your mind. What sissy could turn down the offer of wearing frilly panties 24/7? None is the answer and you just confirmed it. Of course good sissies don’t back talk either so I guess a punishment is in order.” The voice said.

Mark really wanted to protest this, but what would it help? Hell why would the person behind this even listen. Back talking on his punishment for back talking would probably only lead to more punishment. It was probably best to just take the punishment and get it over with. If only he had a bargaining chip himself.

“No protests? Good sissy. You’re a quick learner, aren’t you? Although I have to say I had hoped you would protest again so I had another reason to punish you. Anyways you just about confirmed how big of a sissy you really are. So now for your punishment. You are going to take a pair of scissors, and gather every pair of boxer shorts you own, those in the laundry basket and the ones your closet. Make sure you have them all, no tricks or anything cause if I ever see another pair of boxers that aren’t mine you will be very sorry. Now get going.” The voice said.

With a deep sigh Mark headed to his drawer which held about 19 pairs of boxers. He found another five pairs in the laundry basket. Doing a quick canvas of his room scared of the consequences missing a pair would have he came up empty. Finally certain he had collected them all Mark went to his desk and fished out a pair of scissors from one of his drawers.

The moment he had the scissors in hand the voice started up again. “Good sissy, now get on your knees in front of the boxer pile and cut them all in half going from the crotch to the waistband. While you are doing so I want you to put on a big smile and say. “Finally, I have enough pretty panties not to have to wear those boring boxers for another day in my life. The only boxers I need are those of my Master. I just love being able to smell a real man when I play with my clitty.” You better sound excited as well sissy.”

Mark sat there in shock. He couldn’t believe he had to do this. If he destroyed all of his boxers, panties would literally be the only kind of underwear he owned. Willing or not he would have to wear panties out or nothing at all. The text he had to say was even worse than having to his boxers up. Combining that with the overly frilly set of lingerie he was still wearing. He would really look like the world’s biggest sissy.

He wasn’t stupid either. He realised that those instructions were crafted to make yet another condemning video on that damn site, but what could he do about it? There was already so much video material and pics on there that it wouldn’t really make a difference. At least that is what Mark tried telling himself to justify what he was about to do.

A deep sigh later Mark closed down the pair of scissors between the legs of his first pair of boxers. “F…finally I have e…enough pretty panties not to have to wear those b…boring boxer for another day in my life…” Mark started to stammer looking miserably. He was visibly cringing with Every cut he made it felt like he was cutting directly in his male ego.

“Stop and start over. That’s just purely pathetic. Say it like you mean it. Make me believe you just can’t wait until this task is over, so you are finally released from all that nasty boy underwear. We are going to keep on doing this until you get it just right. Even if that means you have to go out wearing that lingerie set again to purchase extra boxers only to cut up.” The voice said before it had even let him finish his first full repetition.

The next try didn’t end up being any better, nor did the one after that. Seeing the pile of boxers slowly getting smaller made him feel the threat of being send out to get more boxers. For the first time Mark significantly improved. Apparently, all he needed was a little motivation and John was more than happy to provide just that. A few tries later the mechanical voice spoke up again. “Since you are obviously not even trying I have started compiling a mailing list for your website. At this rate I am going to need it very soon, so I might as well have it ready.” This was followed by a series of names and surnames simply dictated, but they had a big impact on Mark. It were the names of his closest friends letting him know that this person wasn’t kidding when he said he could send them the link.

Just like that Mark’s performance improved significantly. “Finally, I have enough pretty panties not to have to wear those boring boxers for another day in my life. The only boxers I need are those of my Master. I just love being able to smell a real man when I play with my clitty.” He said almost breathlessly with an ear to ear smile.

“Again, it sounded to forced.” The voice said before shutting down again. Too forced? Of course it sounded too forced. This was forced after all, there was no way he would say something like this in a million years.

Panicking Mark started to improvise. He just had to get it right or his whole image and life would be destroyed. “Yay, I finally have enough of deliciously frilly pretty panties to get rid of that nasty boy underwear for good. The only guys underwear a sissy like me needs are the worn boxers of my Master. They always smell so deliciously of real man. I just can’t keep myself from smelling them when I am playing with my clitty. They are just to yummy.” Mark said with a big smile even slightly raising his voice pitch mimicking how he imagined a little girl would talk if she got a pony. He felt completely ridiculous doing it, but with only a few boxers left he felt desperate.

John had to admit he was a bit surprised hearing what Mark said. He nearly instantly had a laughing outburst. “That wasn’t what you were supposed to say but I’ll take it. Now be a good sissy and cut up the remaining pairs. Oh, I am sure you will be glad to know that this pair is starting to get very yummy like you called it.” John made the mechanical voice say before playing a loud farting noise making Mark gag instantly.

By now John was just messing with Marks mind but he was having a great time. Besides he wasn’t really lying either. Even though he had only forced some new clothes and a waxing session on Mark, he already looked good enough to Make Johns cock stir. Especially with the feeling of complete control over the youth. Even Marks figure looked a bit effeminate on its own. Given a little bit of help he guessed he would be able to make the effeminate figure just girly. A change of hairdo would also be nice, if Marks hair was at least combed instead of a tangled mess it would go a long way already. The change of hairstyle was certainly a good contender for the next big change, John thought adding it to his list of ideas.

Pitifully Mark cut up the last pair of male underwear he owned. He would basically have no choice but to wear panties or go commando. Being caught commando especially with his new pubic hair would be just as embarrassing as being caught in panties and since not wearing panties meant punishment it sadly was the preferred option. He was positive that they hadn’t be spotted when he went to Suzan so maybe he could pull it off?

He certainly hoped so because he had no other options, Mark thought before the voice ripped him back out of his thoughts. “Alright sissy, you can take off everything but the panties for now and get dressed. The box you brought up is to be opened this evening when I say you can. That’s it for now, enjoy your day panty boy.” Despite the voice having no real intonation Mark could still make out the taunting way in which he imagined those words would be said.

Mark sighed his morning had been really intense so far, but at least he was free to do what he wished now. Going to the skatepark to take his mind of things would be a big relief. Even if he still had to wear these stupid panties, he would at least be away from the control of his blackmailer. Although wearing those panties technically meant he was still controlled even then in a way. Mark just tried not to think about that.

At least he could finally pull off this bra even though he didn’t have breasts the straps had been tight enough to dig into his shoulders and back anyway. Just pulling it off brought great relief. So did pulling off that horribly constricting garter belt girdle. At last he could breathe freely again. The only garment that had felt somewhat good were the stockings, sliding this sheer nylon material off his legs felt electrifying, just as slipping them on and pretty much every movement he had made with them felt.

The only item of the set left were the panties, but those Mark couldn’t take off, well he could always wear another pair instead, but he simply didn’t see the point in doing so, each and every one of them was just as horrible as the last. Safe for the pair he had gotten from his girlfriend, but then again, a racy thong wasn’t exactly a look he liked either.

Trying to just forget about it Mark quickly covered up the panties with a pair of his jeans and a long-bodied t-shirt. This at least removed them from his view, but due to the slippery satin material on his smooth skin and the tightness stemming from his carefully tucked away penis in the gaff part, Mark couldn’t forget about them for even a second.

The only comfort the pants and t-shirt formed were as a barrier to keep anyone else from finding out about his predicament. It was all that mattered for Mark now. He quickly finished dressing and piled all the cut-up boxers into his arms carrying the result of his latest punishment to the trash. The boxers were completely useless in their cut-up state and yet it hurt to have to throw them away as well.

After dumping his cut-up boxers Mark took his skateboard from the garage and went straight to the skatepark. He wasn’t going to risk heading back upstairs only for who his blackmailer to change his mind and decide not to let him go just yet.

The closer to the park Mark got the more nervous he grew. He hadn’t seen his friends since Wednesday and since then all his hair body hair and his beard had been removed. He was also wearing panties here for the very first time. Not showing up for one day wouldn’t raise any questions yet for Mark it had felt like an eternity with all that he had been trough.

When he arrived he just got greeted like normal, a simple greeting no real special attention or anything. Just like no one even noticed something had changed. Well the only visible change that happened was the removal of his sparse goatee and moustache, but no one seemed to notice or care about it.

It actually was a huge relief, maybe he had just made things way worse in his mind than they actually were. Well of course the panties would get out strong reactions, but no one had to see those. He deliberately kept his skating simple instead of doing tricks to make sure he wouldn’t fall and be accidentally exposed, but apart from that he actually had an uneventful good time. It was strange how good a sense of normalcy could feel.

Everything that happened remained somewhere at the back of his mind, the alien feeling of his pants on smooth legs and the panties holding back his penis and balls in their slippery satin grip served as constant reminders. Yet since no one noticed he was mostly able to put those worries aside as well. It felt freeing.

When Lisa arrived however she instantly noticed Marks lack of facial hair. “Hey champ, finally decided to get rid of that ridiculous thing you called a beard?” She said making him blush. “I mean it was only a couple of sparse hairs and honestly it wasn’t nice to look at at all so I’m glad you did.” She continued on in honesty.

This confused Mark a little. He had always hold on to it to the best of his abilities thinking he needed it to be seen as a guy. Sure his mom had often bugged him about getting rid of it but apparently his girlfriend had disliked it as well?

To his huge surprise Lisa approached him only to pull him in a long tongue twisting kiss. One of the most intense ones they had ever shared. “Mmm so much better without all that hair cutie.” She said once she pulled back giving him a wink.

Mark didn’t like being called cutie, definitely not considering his current predicament. After that mind-blowing kiss however, protesting was about the last thing on his mind. “Uhm, yeah thanks. I have decided to start shaving.” He said trying to still appear manly. There was no way he would let anyone know that it had been waxed instead.

“Well I love it, so keep it smooth for me, will you? Mmm just looking at you gives me the urge to kiss you again.” Lisa said.

“You don’t have to resist your urges for me babe, and I definitely plan to keep it up.” Mark said feeling a bit more confident about his situation. His face would probably stay hairless for about a month after that waxing he got so this would serve as the perfect excuse.

Promptly Lisa gave him another intense kiss making his heart flutter. Never would he have thought that anything good could come from what he was going through and yet Lisa had just debunked that entirely.

Mark had an awesome time at the skatepark, better than ever before. No one realised anything, and Lisa seemed so much more interested in him. Normally they rarely kissed or did anything exciting but today she seemed to be unable to stop herself from kissing him as much as she could. It was a great boost for his confidence.

He had such a great time that he lost track of time and was nearly late for diner. Luckily there was no other package delivered for him while he was gone, otherwise his parents would have found it for sure. Still thriving off euphoric feelings his day at the skate park had provided he sat at the table all smiles. What had happened in “CC’sboutique” this morning almost seemed like an afterthought despite the reminder the constricting gaff panties still provided.

Over dinner Mark was much more talkative than usual. Normally he remained silent, but today he engaged in a lot of small talk with his parents. “Well Mark, it’s a relief to see you so happy. I’m also glad you have finally decided to take care of that way too long fuss you called facial hair. Me and dad had been slightly worried about you, given how much time you have spent in your room lately, but clearly that worry was ungrounded.” His mother said.

“Oh yeah sure mom, no need to worry about me. Everything is great and for the beard you can thank Lisa, she really managed to persuade me to go clean shaven from now on. Anyway, I’m back to my room.” Mark said joyfully the topic making him realise that he probably should go check if he wasn’t in trouble with his blackmailer yet. He had never stayed away from his room for this long since the blackmailing had started.

The moment he stepped foot in his room the mechanical voice came to life. “There you are sissy, I was starting to worry that you had run off with a boyfriend or something. Anyway, now that you are here strip down and pull on your full lingerie set again.”

In an instant Mark’s whole good mood was gone. He was pulled back to the horrible reality of the predicament that he had managed to forget for a while. The voice was all he needed to be pulled back to his scared agreeing mindset that had developed through carrying out the various tasks laid out by his blackmailer. Unlike at the start of all this resisting was more of an afterthought. He still balked when new things got introduced sometimes needing encouragement in the form of another threat.

Dressing up wasn’t new by a long shot however and so Mark did so without being asked. He still had difficulty putting on the bra in a smooth fashion, the garters were also still hard. He did however take into account the things Stephanie had told him. He checked if his seams were straight and made sure to pull the garter tabs underneath the waistband of his panties.

All in all, it took him 10 minutes to get completely dressed up in his newly purchased set of lingerie. His body once more encased in frills, lace and satin, Mark once again looked way girlier and way more appealing to John who had fished his cock out for what he was about to order next. “Alright sissy, since we were so busy this morning you forgot to properly show me your new lingerie set. So this is what I expect from you. You are going to give me a nice twirl and say “Look what I bought today master. I really hope this sexy set of lingerie is able to make your cock hard. You know cause I simply love hard cocks.” Like with the boxers I want you to look and sound excited while saying it oh and this time I want you to giggle afterwards. Now get to it sissy.”

Mark shuddered hearing what he was supposed to say. Just the thought that this might actually be making someone’s cock hard was more than enough to make him feel sick. He knew what he had to do however and despite how hard it was he did it. There was no point in resisting, otherwise he would be stuck doing this all night. He quickly spun around his centre and said “Look what I bought today master. I really hope this sexy set of lingerie is able to make your cock hard. You know cause I simply love hard cocks.” He forced himself to get out a nervous laugh along with the biggest smile he could give.

He had done it without stammering or anything and yet the voice quickly spoke up again. “Not good enough, laughing like an idiot is not the same as giggling also twirl a bit more gracefully, you look all pretty so you better act all pretty as well got it faggot? Now again and don’t worry this time there is no limit to the times you can try. You can even take all night if you have to, but one thing is for sure you are going to give me the perfect sissy twirl and text tonight.”

Mark felt his heart sink hearing the feedback over those doomed speakers. Hadn’t he been through enough yet today? He sighed deeply trying to shake the feelings of dread, so he could give this task his all and look convincingly excited.

Three tries later it still wasn’t good enough, but this time the voice suggested a different approach. “Why don’t you adapt your text slightly? Improvise a bit, it seemed to have helped you sound more convincing last time so do it again. I don’t want to hear my exact words coming from your mouth again or the fliers get spread.”

His eyes went big, improvise? He had been scared to do so ever since this morning because he had been shocked about what he had ended up saying in his desperation. “Oh look what I bought today master. Do you like it? I really hope this sexy set of lingerie is able to make your cock hard. You know cause I simply love hard cocks.” Mark said after another twirl forcing out something that could almost pass as a giggle.

“That was barely different sissy, try again and try fucking harder.” The mechanical voice said prompting Mark to repeat his twirl routine.

“Oh Master, I’m so excited. Look at what a sexy set of lingerie I got. I really hope it’s able to make your cock hard cause you know how much I love hard cocks.” Mark gushed getting out a nearly perfect giggle afterwards.

“Again.” Came the hard answer over the speaker. Mark couldn’t believe it, but with little choice he tried again and again. Each time his text got more exaggerated. After a few tries he even tried using the higher pitched voice again.

“Oh Master, look at what a deliciously cute set of lingerie I bought to day. Isn’t it just the best? I hope it is at least cute enough to make that deliciously smelling cock of you rock hard cause you know how much I simply love cocks.” Mark said with an exaggerated giggle.

John laughed to himself witnessing the whole show. Making Mark come up with this on his own instead of reciting was so much more entertaining. Besides it would without a doubt help get his mind set in the place of a true sissy. If he had to use his own imagination on his debasement Mark would have no way to distance himself from what he was saying anymore. Over time it would really start shaping his mind or at least that is what John hoped.

One thing was for sure, he was spot on about it being more humiliating. Mark had reached a new height of humiliation. At least he was rewarded by a confirmation that it had been good enough this time. “Alright, sissy that’s enough. You may now open the box you have gotten earlier today. Go ahead, after your little speech I am sure you will just love it.”

If the voice said he would love it Mark was positive, he would hate it. Taking the box and cutting it open with the scissors he had used to cut up his boxers. Looking inside Mark was horrified. Beside another pair of Ziplock sealed boxers there was an enormous suction cup dildo. It looked very realistic and simply huge. The material looked a bit brownish, instead of the pinkish colour of most dildos. It had a couple of well-defined and life like looking veins running along the length and the bulbous head was deep purple in colour. There even was a slit in the top of it making it look even more real.

The cock was at least 8.5” probably larger even and it looked almost as life like as his very own penis. Hell, if he hadn’t known better he would have thought it was a real cock. Deeply shocked Mark just looked at the monster with his mouth agape.

“Good sissy, looking at a cock with a wide-open mouth like a proper cock hungry slut. You can touch it, go ahead. Take it out and put it on your nightstand.” The voice said, Mark didn’t react however. He couldn’t get himself to touch that thing. No, it was just gross.

“Take that damn dildo out and put it on your nightstand right now sissy. Do it or I will be sending out every damn piece of video material I have on you to all your friends and every major porn site.” The voice on the speaker said shocking Mark enough to make him take action.

With a shaky hand Mark reached inside the box shuddering as soon as his fingers made contact with the dildo. It even felt so goddamn real. Since he had already touched it he might as well grab it cause he needed to get that dildo on his nightstand as soon as he could before his blackmailer made true on his promise. Closing his eyes and holding his breath as if it would help any Mark grabbed hold of the dildo and pulled it out of the box. It was highly unsettling. The thing felt rigid and still flexible, soft to the touch just like a real penis. The only difference was that this dildo did not feel warm like a real penis should.

Dildo in hand Mark rushed to his nightstand and put the thing down as fast as he could. He really didn’t want to touch it any longer than necessary. John was laughing his ass of at the show, the dildo had been very expensive, but he would make sure to get every penny of worth out of it and this definitely was a good start.

“That dildo is an exact state of the art replica of the very penis you have been smelling from those boxers all along. My present to you and from now on as part of your routine you are required to give the tip a good morning and goodnight kiss, as well as a goodbye and hello kiss every time you leave or enter your room. It goes without saying that your nightly and morning masturbation sessions are still mandatory as well. Goodnight sissy and enjoy your present.” The voice said before going dead.

“Oh, before I forget, you are required to be in full lingerie while in your room from now on. To make sure you don’t run out you will hand wash everything everyday just like you have done with the panties and tomorrow you are expected to go buy a new set yet again. Make sure to go to that same shop.” The voice said before going quiet again.

Mark just sat there in his room mortified. He couldn’t even grasp what had just happened. The control he thought he still had in a way was completely slipping from his fingers. He didn’t know what to do, he didn’t know what else he could do than what was required of him and so still numb from the shock Mark just went ahead and carried out the orders on auto pilot. His mind was spinning wildly as he pulled the strong-smelling boxers over his face. Instantly his cock jumped to attention despite the horrid state his mind was in.

It took a little longer than usual but helped by the new sensation of these sensual slippery new fabrics his lingerie was made of, especially the electrifying way his sheer stockings felt underneath his sheets, he came.

Putting the boxers aside he leaned towards his nightstand looking at the monstrous big phallus standing on top of it, complete with balls and everything. Closing his eyes, he gave the purple head a quick peck shuddering in disgust as he felt the lifelike silicone make contact with his skin. After that he quickly killed the lights and turned his back to the dildo while trying to fall asleep.

(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.)