Chapter 2

 

When Mark woke up the next day his parents were already gone, as usual. He was no early riser after all. He made some breakfast, gamed a bit made lunch and went to the skate park. There didn’t seem to be any signs that flyers or anything like that had been spread much to his relief. Yesterday had certainly been a scare, maybe it had just been a cruel prank. After all it had been embarrassing but all things considered not that much worse than what his girlfriend had made him do over webcam. As the day passed by Mark managed to cast those humiliating memories out of his thoughts, and by the time he walked home he didn’t even think about what had happened anymore.

 

It all came crashing back when he saw another brown envelope laying on the doorstep, his heart started racing and in panic he snatched it up quickly stepping inside. Mark hadn’t needed to read his name on it to know it was meant for him. The moment he did though he was horrified to find it addressed to, “Sissy Mark”. What if any of his neighbours, or the mailman saw this envelope? They would surely have questions. What if they would decide to open it? That would most probably be a disaster.

 

Mark took the envelope to his room nervously. He didn’t know what was in it, did he even want to know? Considering the way it was addressed he probably wouldn’t like the contents at all. Most of all he just wanted to burn and forget about it. If he did that he would be royally screwed though he wouldn’t know what his blackmailer expected of him, not that he wanted to. The last thing he wanted was to play that sick bastards’ game any longer, a one time off had been more than enough. Those flyers though, no matter how much he hated the idea of putting up with another potential task. It was still probably preferable to those flyers and that website being spread. If those ended in the wrong hands with all the insinuations made he might even get raped.

 

He had always been the kind of guy to envision doom scenarios and right now that wasn’t helping his case at all. With dread he decided the best thing would just be to get this over with and so he reluctantly opened the envelope dumping the contents on his bed. Mark was horrified to see a plastic Ziplock bag with what looked like grey cotton fabric inside, a pile of bright baby blue fabric judging from the silky looking fabric and the lace he guessed these were panties. Last but not least there was a note.

 

“Hello again Sissy,

 

Yesterday I told you that a good sissy always obeys and well I have to say it really appears as if you are very motivated to be a good sissy. Anyways, I am sure you are just dying to find out what you must do next. I bet you have been looking forward to this moment all day and rest assured, I just know a big sissy like you is going to love this.

 

If you are reading this note I guess that means you have also found my other two gifts. One is a new pair of panties for you, seeing how much of a sissy you are, I bet you can’t wait to try them on. The second thing is a pair of boxers. Here is what you are expected to do.

 

• Put on the panties, they are to stay on all evening and night, in fact all the time you are at home you will spend in your room wearing nothing but the panties I demand you wear that day. This also means when you are sleeping.

 

• Like last time all curtains stay open, at least until you decide to sleep.

 

• Once again you are supposed to read a fashion magazine for at least an hour.

 

 

• Just before going to bed you are required to pull the boxers over your head, the crotch part covering your face. Like that you are required to masturbate to climax in your panties. You don’t clean them, you just sleep in them. First thing in the morning you are to repeat masturbating just like this once more.

 

• After your morning masturbation you are to hand wash both the panties and the boxers. The panties should be hung in you room to dry. The boxers are to be put back in the Ziplock bag and be left out on your front porch like that.

 

• If you are going out that’s then end, if you plan to stay in however you put on a fresh pair of panties.

 

Just for your info, those aren’t just instructions for today. From now on those are the rules you need to follow. As always, good luck and have fun sissy.

 

1. The copy centre let me know that they have received my order of 2000 flyers. It is in processing as you read this. So if you know what is good for you I suggest you follow these rules to the letter or I might be inclined to start spreading the flyers on arrival. I could also just give them to the local post office to be spread as advertisement, one for each household in your and the surrounding neighbourhoods.”

 

Mark’s head was spinning, his stomach was in knots and he had gone completely pale by the time he had finished reading the note. Like yesterday he could somewhat convince himself that wearing those panties, while very humiliating wasn’t that much worse than what he had done so far. Those boxers were a whole different beast however. The insinuation the Ziplock bag made as well as the order to hand wash them made Mark fear the worst. He had nearly made up his mind to follow the orders except that one when he read about the flyers. Someone ordering 2000 flyers was very serious of spreading them and the way of spreading suggested was the worst he could imagine. Everyone he knew and encountered would find out. The chance that there wasn’t at least one pervert who might use the info on the flyer, over a total of 2000 households was also very small in Mark’s mind.

 

He felt sick but trapped. Following those rules to the letter would be the only way he could kind of salvage this mess and he knew it. Slowly he stripped completely naked and slipped on the panties. The material felt quite slippery on his soft cock. To his despair the panties fit perfectly as well. His cock was not supposed to fit in panties he thought mournfully as he looked at himself in the mirror. The panties where bright baby blue all over, they were made in a hip huggers style with a slippery front and a back nearly entirely in lace. In the front sat a small satin bow as well.

 

They made Mark blush profusely. Somehow the fact that those weren’t his girlfriends’ panties, that he could only really think of them as his made this so much worse. At least these didn’t seem to ride up his crack but they still snuggly hugged his buttocks which was about just as bad. To Mark it all looked embarrassingly feminine even if in reality the whole thing was rather unsightly with his pubic hair poking out he didn’t have much body hair yet but the hair on his legs and pubic area was quite pronounced.

 

It took a moment for Mark to come back to his senses. He was stuck in his room wearing nothing but panties. Usually he had no problems keeping himself busy, but this was way different. He felt nervous like he was being watched even if he had seen no one when checking his windows for his possible blackmailer. Eventually he decided to just start reading that damn fashion magazine again. At least it would be one thing that was out of the way.

 

Unlike yesterday he actually started reading right away this time. Fashion was boring but just staring at a paper not doing anything for an hour was even more boring. Having read intensely he was actually glad to notice the hour had flown by. The topic wasn’t interesting, but he had had something to do which made this part bearable. Combined with yesterdays Reading he had pretty much finished the entire magazine.

 

He had only put aside the magazine for a minute worrying about what to do next when his mom called out that the dinner was ready. Shit dinner, was he allowed to wear boxers now? It was still in the house, so he doubted it. He couldn’t go down to his parents wearing panties, though could he? Mark was torn between ditching the panties or not. If he did that might mean those flyers getting send though and he couldn’t risk that. Eventually he just decided to keep them on under his other clothes hoping his parents wouldn’t notice.

 

Sitting at the dinner table made him feel extremely self conscious. He could feel the presence of the panties all the time which in turn made him feel like they were very noticeable. It felt like it was only a matter of time before either his mom or dad called him out on it, Mark thought while cautiously eating his meal. When his mom did address him, he had a small panic attack. Luckily she only asked if he was feeling alright since he looked somewhat tense. A question Mark quickly waved away saying he felt good. It was a big relief to get that question instead of the one he had been fearing. The rest of the meal passed by without further incidents. To his huge relief no one at home had noticed.

 

With dinner over he instantly ran up to his room feeling relieved. A relief that didn’t last long when he realised he should really strip in order to keep his blackmailer happy. Like that Mark was once again wearing just the baby blue panties he despised. To think that he would have loved seeing these on his girlfriend was rather disturbing as well.

 

It was still early in the evening and Mark had nothing to do anymore, nothing but that masturbations session he dreaded. That was only just before going to sleep though and it wasn’t even near time to do so. Normally he gamed with his friends, but he was kind of scared that they would somehow find out about his situation if he did so. He knew it was stupid, yet he had this nagging feeling they would somehow find out. Eventually he ended up just playing a single player game until it was bedtime.

 

Mark had waited as long as he could to head to bed, but he was really tired by now. It was later than usually all cause he wanted to avoid what he knew was required of him. The thought alone of those boxers made him feel sick, but the time had arrived. It was either this or never showing his face to anyone who lived remotely close ever again. Not even his parents. He would be all alone on the run if those flyers got spread.

 

This is for the best, he tried convincing himself while taking the Ziplock bag of boxers and reluctantly opening it up. Feeling sick he picked the boxer shorts out of the bag and held them up surprised that they were huge. It looked like Mark could easily fit into them twice. Worse even was the fact that they were definitely worn. They smelled even when held at an arm’s length and Mark recognised the dried white material in the crotch all to well. He had thrown many pairs with the same stains in the laundry.

 

“Come on Mark, you can do it, just close your eyes and get jerking. It will be over before you know it.” He said out loud to his reflection. Mark normally never spoke to himself but right now he really needed the extra courage it gave him. He already felt sick just thinking about what he would do. The boxers smelled terrible and the smell wasn’t even that strong yet. This was just the worse Mark thought as he laid down on his bed.

 

He took a deep breath before reluctantly pulling the boxers over his head, the crotch part covering his face as instructed. Mark nearly lost it when he felt the white crusts against his face, but he started to masturbate anyway. He jerked as fast as he could all the while holding his breath somehow hoping he could avoid breathing, but due to the intense effort he had no choice but to breath in after only a few seconds. When he did the smell instantly made him gag. Tears shot in his eyes and he had a real hard time not throwing up. The smell of these nasty boxers was a really strong one up this close. It smelled of someone’s sweaty musky balls mixed in with the smell of stale cum and a hint of urine. The smell was overpowering and made his head swim while he violently gagged, tugging at his still soft cock in his panties.

 

It took Mark a while until he was able to breath without gagging, and even longer until he finally managed to get hard. All of this on pure physical stimulation and willpower since the intense humiliation and the nauseating smell kept him from feeling good mostly. In the end it took him nearly an hour total, first to get over the gagging, then to finally get hard and finally to shoot his wad in his new panties.

 

As soon as he was done he threw the boxers away as far as he could, he was mortified and exhausted, yet sleep didn’t come easy. He was still too much in shock about what he had just done that he laid there wide awake, the sticky panties serving as a horrible reminder of his nasty deeds. The fact that he had to do this all over when he woke didn’t help either. What the hell had he gotten himself into, and better yet how should he get out? Were his last thoughts before drifting of to a troubled sleep.

 

John had been watching the whole thing with a huge smirk. None of this had originally been planned, but he kind of liked the way this was going. The boxers had been a spur of the moment. The idea of this loud-mouthed brat who thought of himself as so much of a man having to smell what a real man smelled like, was just too good to pas up. It would serve as a good lesson in humility John thought sure seeing Mark laughed at and disappear would have been a good revenge, but this was so much more satisfying. This lasted instead of just prompting Mark to disappear embarrassed. John had doubted Mark would put up with those rules but apparently the guy was more of a wimp than he thought.

 

In the end this was just entertaining and justice, John kind of got horny from the power he held but that was about it. There was no attraction to anything other than the power. It was just a fun experiment to see how much Mark would put up with before he snapped. John certainly liked thinking about what further humiliations he could come up with to make that asshole really squirm.

 

For now though this would do John thought as he shot his wad into a new pair of boxers to his favourite porn. Some hardcore version of a man his age dominating a frail girl way younger than him into doing whatever perverted sexual act he desired. John discarded his boxers with a smile thinking about how Mark would have his face buried in them by tomorrow night.

 

The following morning Mark woke up with a sense of severe dread, his panties had dried and became crusty over night, but he knew he was supposed to do a repeat this morning. It would be best to just get this over with and head out for the day, so he wouldn’t need to wear panties again. Mark thought as he retrieved the boxers from where he had thrown them and started masturbating again. It wasn’t any easier than it had been yesterday, but eventually after another long masturbation session he managed to get the job done, starting his day out completely humiliated.

 

With a sigh he went to his bathroom to wash out the boxers and his cum soaked panties before taking a long shower spending extra attention on washing his face. Despite having washed several times Mark still felt dirty. He knew this was only mentally though and that all the soap in the world wouldn’t be able to help.

 

He got dressed, put the boxers back in the Ziplock bag feeling nervous about leaving them on the porch. What would people think if they saw this? He decided to just not think about it as he headed off to the skatepark.

 

The plan had been to stay there as long as there was at least one friend of his, but then he thought about how this blackmailer left envelopes and he certainly couldn’t risk anyone but him finding those considering what was most likely in them. The fact that he had to be home before his parents made him arrive quite early and just like expected there was a new envelope.

 

Mark didn’t even think anymore, he just snatched it up and took it to his room to empty. This time the contents were a pair of pink Mesh panties with pink ruffles around the waistband and leg holes. There was also another pair of boxers, but no note. There was no note needed. Mark knew what he had to do despite not liking it. He stripped put on the panties and followed the same routine as yesterday.

 

This routine repeated itself day after day, in the weekend when his parents were home he got a text with the info where the envelope of that day was hidden. This went on for 8 days, during this time john was just happy working up a sweat, cumming in his boxers more than once, not even bothering to shake off those last drops before shoving his cock back into his boxers after peeing. All to give Mark a very nice and smelly pair of boxers for the next day.

 

The humiliation of the act never seemed to lessen, but without really realising it. The masturbation got easier. Mark focused so hard on just cumming as quick as he could that he failed to notice that by day 8 he already got hard before even touching his cock. Masturbating twice a day while smelling these dirty boxers was starting to form a connection in his brain, a connection between arousal and the scent of unwashed cock. His last masturbation session hadn’t even lasted more than 3 minutes.

 

Up until now things had been easily hidden. During the day he had time to meet and socialize with his friends even if he was a bit more nervous and on edge lately neither his friends nor girlfriend seemed to suspect anything. Although he spends all his time in his room his parents weren’t worried either. They were quite used to him spending a lot of time on games and whatever a boy that age got up to. Neither of them really wanted to walk in on that. Little did they know he spend all his time up there prancing around in panties and masturbating with a pair of smelly boxer shorts. Apart from that Marks life was relatively normal.

 

To John this routine was starting to grow a little dull, he needed something to really make the guy squirm again. Sure, Mark was still embarrassed about it all but even the smelly boxers seemed to have lost their repulsive effect. Well Mark still seemed repulsed by the way he handled them but there was no more gagging or anything like that. Instead the guy seemed to get hard instantly by now. John hadn’t anticipated this, but it sure looked funny as hell to see Mark pop a hardon in his panties when he smelled his boxers.

 

It was Wednesday when there was a sudden change, along with the usual pair of panties and the boxers was another note.

 

“Hello sissy,

 

I see you have been having a lot of fun, with all that jerking off you do I have come to the conclusion that you must simply love all your panties. You certainly seem to love my boxers, always grabbing them to jerk off with.

 

Anyways, there just seems to be something off about the image and I believe I know how to fix it which is why I have decided to get you a treat. A nice gesture since you have been such a good obedient sissy so far.

 

I have made an appointment for you on the following address, be there at 10 am sharp and wear those purple bikini styled panties with the big pink bow in the back. Make sure you follow trough with this or I swear there will be hell to pay.

 

Have fun sissy, by the way your website is also getting better and better. Before you decide not to show up I advise you to check it out.”

 

The letter read, making Mark’s heart sink in his chest right away. When looking up the address he found out that it was some kind of salon in a shady part of town. It was a while away from the suburban neighbourhood he lived in. It was an area that had always kind of given him the creeps and he really didn’t look forward to going there, especially not wearing panties under his clothes.

 

After checking out the updated website however there was no more doubt in Mark’s mind. He would be going to that salon willing or not. If he had thought the website had looked bad before it was terrible now. Apparently the blackmailer had been watching him, that while he had been so careful to check his windows. Upon closer inspection he noticed that the angle came from his own webcam?!

 

As fast as he could he grabbed a post it note and put it over the webcam. At least the source was eliminated now. Not for long though as he nearly instantly got a text from that anonymous number. “I see you discovered my eyes, you better uncover that webcam right fucking now though or I swear to you everything is going online this instant.” The message read making Mark take off the post it with an intense feeling of defeat. He knew that this was basically giving permission to his blackmailer to film him, but what could he do about it?

 

Mark felt so lost, rationally he knew that he should cover up the webcam, but this website was so awful. It had a whole gallery of videos of him jerking off in various panties with various dirty boxers over his head. It was the caption that filled him with real dread though. “Sissy Mark has clearly grown addicted to panties and has been shopping for them a lot. Although he claims not to like cock the fact that he steals his daddies dirty underwear to masturbate with clearly shows otherwise. What sissy Mark really needs is a big strong man to show him just what a cock loving slut he really is.”

 

Great Mark thought, the chance of getting raped if this ever became public has just exponentially increased. What was he going to do? It seemed to be too late to back out now. The only thing he could think off was just show up at that salon. How bad could it really be? What could they do? Put some makeup on him? Sure, it would be humiliating and even worse to get through that neighbourhood, but he would just wear a hoody and wash it off as soon as he got home Mark thought.

 

No one would ever find out, at least he hoped so. For the remainder of the evening Mark followed the same routine he had been following for more than a week now. He slipped on the new panties, a thong in white satin with bright violet lace around the edges and a small violet bow upfront. All his panties were colourful in some silky or lace fabric and very sexy. He didn’t care anymore though. All he cared about now was getting his jerk off session over with before going to bed worried about his salon visit tomorrow.

 

(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.)