Part 1

Intro

Mark had always been somewhat of a neighbourhood terror. Every time something in the neighbourhood got vandalised you could count on it that Mark had something to do with it. To the frustration of many neighbours, his parents didn’t really seem to care. His family was pretty well off and with his dad being a lawyer Mark always seemed to get out of every situation unpunished. At least it looked like this terror was finally going to end. Mark had turned 18 earlier this year and had now graduated high school. After the long summer break he would head off to college and his reign of terror would finally end. Pretty much the whole neighbourhood thought Mark didn’t deserve to go to college, but most of them were happy he would be gone.

A lot of this behaviour originated out of overcompensation for the fact that Mark, unlike most guys his age hadn’t quite grown out to be tall and muscular. At 5’6” he was the smallest guy in his class. His body was lean instead of muscular and he really hated the fact that his fat seemed to get stored mostly around his bottom giving it a slight bubble butt like appearance. Around his sixteenth his body hair had started to grow finally, but it was a slow process. By now he had quite a large pubic bush, a little darker fuss on the arms and legs and three hairs on his chest. His face was kind of roundish with bright green eyes and dark brown hair. In terms of beard he only managed to grow a sparse moustache and a goatee which he proudly kept.

To look tougher Mark had tried adopting a skater look, something that fit well with the mischief he spread across the neighbourhood. It also gave him a sense of belonging, most of the skaters were actually quite chill and they accepted him even if the look didn’t really suit him. The baggy clothes helped cover up his slender figure and bubble butt, but the way he kept his hair in a messy shoulder-length style made him look awkward. It was better now that he had some sparse facial hair, but not by much. The moustache and the goatee were too thin to look nice. His mom had often bugged him that he needed to shave, but that wasn’t something Mark ever planned on doing. He was too proud of his beard as he called it.

Reputation and image were very important to Mark and over the years he certainly had built a reputation. Many of his vandalistic deeds had come from dares with the people he hung out with at the skate park. Mark never shied away from a challenge or dare, and it had made him kind of a legend at the skate park. This respect from his peers was a huge confidence boost for his ego and self-esteem which only prompted him to be even more daring.

It’s his reputation that had scored him his relationship with Lisa, a pretty, somewhat eccentric blonde skater girl that was about the same height as Mark. Despite Marks loud mouth and daring behaviour, Lisa was the bossier one in their relationship. They had been together for three months and yet all this time Lisa had kept off the sex. She loved teasing and daring Mark to do all sorts of things to amuse her, which Mark was all too glad to carry out. Just the fact that he had a girlfriend one a year older than him at that made him feel accomplished in his manliness and that was all that mattered to him. It just gave him another thing to brag about.

From all the neighbours there was one guy in particular who had been a constant target of Mark’s vandalism. His next-door neighbour John. For as long as Mark could remember this guy had had quarrels with his parents over the smallest things like a tree branch that hung over the property border, trash that was put out too early,… stuff like that. This was more than enough to mainly focus on this guy when the dare wasn’t specific to a target.

John was a tall guy, somewhere in his mid to late fifties, standing about 6’2” tall. He was balding already, and the remainder of his hair was quickly greying. The guy was somewhat overweight and just a general weirdo. The man lived alone rarely came outside and when he did he complained about everything he saw. Due to his somewhat pulled back live style rumours had quickly spread that the guy was a huge perv.

Despite being a main victim John was one of the only neighbours unhappy to see Mark go to college. In Johns mind Mark needed to pay and when he was away John couldn’t make that happen. For a while now, John had been looking for an opportunity to extract his revenge but up until now without any success.

Chapter 1

Summer break had just started, and Mark was in a great mood. Yesterday Lisa gave him a little striptease show. It wasn’t sex, but Mark had loved it all the same. After all, with a four-month long break Mark had all the time to finally lose his virginity to his girlfriend. He still couldn’t believe he had actually managed to score a college chick. That fact alone made him a legend around his high school friends. The two of them had been talking about maybe sharing a dorm room at college. It was still just talk, though. After all they were in no rush to decide.

After sleeping in Mark went downstairs to make himself a quick breakfast before heading up to his room again. Not having any obligations or pressure to rise early or anything was fantastic he thought as he started up his computer when he suddenly noticed something red on the floor in the corner of his eye. It only took a second for it to sink in that these had to be Lisa’s panties. He still remembered how well she had filled that lacey red thong yesterday. The thought alone brought a big smile back to his face. A smile that quickly turned into a smirk as he realised Lisa had walked out without wearing underwear.

In a quick motion he picked up the discarded panties and instantly brought them to his nose, deeply inhaling Lisa’s sweet scent. It gave him an instant hardon. As the computer started up, he noticed Lisa was online, an opportunity he immediately took to give her a video call.

A few seconds later Lisa answered the call. “Hey babe, are you missing me already?” Lisa asked with a big smirk.

“Oh you know I can’t stand not being with you baby, luckily you seem to have left me a little souvenir behind.” Mark smiled triumphantly holding up the lacey red thong he had just found.

“Oh god I was just thinking about where that pair went. Well, I am glad to see it is in good hands or is it? Maybe you just kept my panties behind to try them on.” Lisa teased with a big smirk seeing the instant horrified expression on Mark’s face. She knew very well that associating anything remotely feminine with Mark made him balk. Mark really had a case of very fragile masculinity and she loved to tease him about it every now and then.

“Don’t worry silly, I am just joking. I am sure you had another very good reason to hold on to them.” She put Mark at ease again with a wink.

The way he nervously replied, “Hehe yeah.” Was all she needed to know to realise she had hit a very sensitive spot.

Being in a mischievous mood however Lisa couldn’t help herself but run with it a bit further. “I bet they would look great on you though. You probably fill them out just as well as I do.” Lisa giggled enjoying the shock on her boyfriend’s face.

“Eeeeh I really don’t think…” Mark said but Lisa interrupted him.

“In fact, I would love to see, just to know if I was right or not. So come on Mark why don’t you try them on for me? After all you got to enjoy seeing me in them, so it is only fair to return the favour, right?” Lisa mischievously pressed on.

By now Mark’s face had turned quite red. “I think it would just look stupid Lisa. You know totally out of place and everything.” Mark awkwardly tried to explain.

His reluctance seemed to egg Lisa on even more though. She would have probably just dropped it but now she really wanted to see Mark wearing her panties and she knew just what buttons to push. “Oh come on Mark, I dare you to put them on or are you too much of a sissy to try on panties? Are you afraid you will like it?” Lisa laughed knowing that Mark wouldn’t be able to turn down a dare. Especially not now she had questioned his masculinity as well.

“I’m no sissy, and I am certainly not afraid of a stupid piece of fabric.” Mark replied firmly obviously offended which was just what Lisa needed.

“Well then prove it and put them on.” She smirked.

“Alright, but you can’t ever let anyone know deal?” Mark replied instantly.

“Deal!” Lisa laughed.

Only now Mark realised what he had actually agreed to. He had been so lost in trying to defend his honour of dare king as well as his masculinity that he simply agreed to do it without a second thought. Now he badly wanted to crawl back, but he knew he couldn’t so with a sigh he got up and started to strip in front of his webcam much to the joy of his girlfriend who was cheering.

Out of his baggy clothes, it was obvious just how slender he was, it also showed how his butt was a bit plumper compared to the rest of his body. With a slight hesitation he slipped on the skimpy red lace piece of fabric only barely managing to get his three-inch soft cock in the front. When hard he grew to around seven inches but luckily that wasn’t the case now.

Lisa instantly started laughing harder, “I knew it! I knew you would fill them out perfectly with that cute butt of yours. This is great. They even match your face in colour.” Lisa cheered even though it was kind of unsightly with the bush of pubic hair underneath.

“Okay Lisa, you’ve had your fun now, can I please take them off?” an embarrassed Mark asked.

“No way! Give me a twirl and a booty shake and then you can take them off.” Lisa instantly replied.

Mark quickly did as he was told before stating, “I’m taking them off now.” And stripping out of the panties before putting on his clothes again.

“That was great, babe. I love you. Anyway, I have to go now, so I guess I’ll see you later.” Lisa said as soon as Mark was clothed again.

“Okay baby, you promised you wouldn’t tell anyone right?” Mark asked nervously.

“Don’t worry about it, a deal’s a deal. This is our little secret. Oh, and you can keep those panties I don’t need them back anymore. Consider it a trophy, I’m really running late though, bye!” Lisa said and as soon as she had said it the call ended.

Mark’s blush only slowly faded away as he scoffed at the panties. A trophy, like he wanted a trophy reminding him of this. His embarrassed look soon turned in a smirk however. The more he thought about it the more he liked the idea of this trophy. Afterall it would be something he could brag about to the guys. Maybe not today but in the future. Scoring a girl’s panties wasn’t a bad thing right and no one had to know how he got them.

The rest of Mark’s day carried on without anything special happening. He played some video games, ate lunch and went to the skate park. He had a great time hanging with his buddies and of course his girlfriend who now seemed to make him blush every time she threw him a smirk. No one knew but for mark the memory of wearing those panties was still fresh on his mind.

When he came back home around 17 o’clock however he immediately spotted a big brown envelop with his name written on it in big black letters. Strange he thought as he picked up the envelope and carried it up to his room.

Upon opening it Mark was shocked to find a ton of pictures of him wearing those panties. They had obviously been taken this morning, but it was hard to say by who. Some were taken from his rooms side window while others were taken from the street side window. Too look inside the street side window would require one to stand way across the street. Which was quite a distance that should make it hard to see what he was wearing. The same goes for his side window. Whoever had taken these had done it with a very good camera and a lot of zoom.

While shifting trough the pictures trying to figure out who did this Mark suddenly encountered a note.

“Hello Sissy,

Did you like the pictures I have taken? It really gets you from all your best angles, especially that cute bubble butt of yours. You really look made to wear panties. I do know a lot of guys who would just love to have a piece of that ass. I wonder how your friends and parents would like to see these pics though. Well unless you want to find out what they think about these pics I suggest you follow the instructions as specified in the mail I send you.

Good luck and have fun sissy.”

As soon as he was done reading Mark’s face went pale. What the hell was he supposed to do? He didn’t know where this letter came from so confronting whoever was behind this was impossible. The thought of anyone seeing these especially his friends was a horrible one. He would instantly lose the whole reputation he had built so carefully as well as all his respect. Lisa knew what was behind this, but would she still love them when he became the loser of the group?

At least his parents weren’t home yet, they only returned from work between 18 and 19 o’clock. Mark didn’t even want to consider the possibility of his parents opening this envelope.

The fact that this guy knew his e-mail address was also quite worrying although a quick google search linking to his Facebook would have done the trick. His Facebook! Mark had never really cared to change his privacy settings which meant everyone could see everything, his friends, his e-mail, his phone number,… everything they needed to ruin his life. He could change them now, but he fully realised the damage had already been done.

With a sigh he decided to just open the e-mail, maybe it wouldn’t be that bad. Maybe they would just ask a bit of money, money he could easily get from his parents with a little lying what it was for. Mark was actually starting to get hopeful. Sure, it would be pretty sour to give money to this asshole but at least it was an easy way out. Upon reading the mail Marks face went completely pale however, he felt himself getting sick.

“Dear Sissy,

I am glad you have decided to follow my orders and open your mail. Good sissies always obey. Now let’s see if you are going to keep on being a good little sissy. I did promise you instructions and here they are.

-              From 18:00 till 19:00 you will put those panties on again. Nothing but those panties.

-              All curtains must stay open.

-              During that hour you will always keep on a big smile.

-              You will sing and dance to at least one recent pop hit.

-              You will spend the rest of the hour reading a fashion magazine. I am sure your mom has some laying around.

-              Once the hour is done you will masturbate to climax in your panties.

-              After that you will clean up your mess, hand wash the panties and hang them out to dry in your room.

Before you decide to delete this mail and pretend none of this happened you should really check out the image I have attached as well as click the link to the website in copy. The website is only visible through this direct link for now. All of that can change depending on your decision however.

Good luck and have fun sissy, I know you will.”

Mark was simply mortified, but when he opened the attachment with the mail he nearly fainted. He was instantly greeted with a flyer size image showcasing a picture of him wearing those darn panties. In the pic his back and bottom showed and yet he also looked over his shoulder making his face recognisable as well. His body had been cut out and pasted on a pink background. The flyer contained everything, his cell phone number, address, full name and e-mail. Alongside it was a small text.

“Hey, I am sissy Mark and I am a cock hungry slut. I would love getting dick pics and drooling over all those pretty dicks. If you happen to live close by don’t hesitate to drop by so I can show you just how much I love cock.

Whoever this person was that had taken these pics, he had certainly put a lot of effort in it. Mark didn’t even dare think about what could happen if this flyer got out. Even his girlfriend who had dared him into those panties would instantly believe that Mark got off on this. Not even to imagine what kind of messages and pics he would get. Worse even if this got in the wrong hands someone might actually drop by and force himself onto him.

The web address also on the flyer proved to be just like the flyer but more extensive. It was all pink titled “Sissy Mark” all his contact info was on it along with the full picture set of him in the red panties. Underneath that set was a caption. “My very first panties, I am so happy to finally set my first steps towards sissyhood. If I get you har, take a picture and send it my way.” This website even had a calendar where visitors could pin when they would be paying a visit. This was just plain sick.

Mark realised that he was royally screwed. If only he knew who was behind this. Well he might find out soon. He was told to keep his curtains open, so the guy would probably take pics again. If Mark could spot him, he would at least know who to confront.

Until the time he was certain however he would need to do exactly as described in the mail.  After seeing the effort put into the flyer and website Mark had no illusion that whoever was behind this would carry out his threats and there was no way Mark could afford that. He wouldn’t even be able to look his parents in the eyes. Especially not if random guys did come around. If this got out all Mark would be able to do was change his entire identity and disappear.

Staying in his room in his privacy where only he and whoever was behind this would see him sounded like the best option. He had already worn the panties so wearing them a bit longer and masturbating in them wouldn’t be that much worse, he tried to calm himself.

It wasn’t working, and Mark didn’t have much time left. 18:00 was quickly approaching so he rushed down stairs and got a one of his mom’s fashion magazines. His parents weren’t home yet so it was still safe. Once in his room he saw that he only had a few minutes left which he quickly used to strip and change into the panties. The feeling instantly made him shudder in disgust. Especially now that he knew he was doing it for some guy instead of his girlfriend. Either way it was best to put them on a few minutes early than a little too late and run the risk of having those flyers send out.

Nervously Mark approached the side window and looked outside but saw no one. He repeated this with the front window but again no one. Where the hell was this guy. Surely, he must be watching right? Mark hated the idea of someone watching him like this. Especially some unknown guy, at the same time though he hoped the guy had seen that he was doing as told so the flyers wouldn’t get spread. He blushed at that thought. Doing as he was told like a good sissy the e-mail had said. Mark was no sissy but what could he do about this?

With a sigh he decided to get on with the singing and dancing. It was the most likely thing to draw his parent’s attention and they would be coming home within this hour. If Mark made it past that he was certain he wouldn’t get caught. He just clicked on the number one hit in the current charts. He vaguely remembered hearing it on a radio somewhere, but he didn’t really know the song.

Mark and his crew didn’t really listen to pop music. It was too mainstream for their rebellious image and thus they labelled it as not cool. Right now, though Mark was dancing in his room feel utterly stupid as he tried reproducing some of the lyrics. It was terrible and so was his dancing. It was stocky at best. Even without elegance the act alone was more than enough to embarrass him to his core.

Luckily it only took a minute or three after which he instantly checked his windows again but no guy with a camera was to be seen anywhere. With a sigh he just got down on his bed and started paging trough the fashion magazine seeing nothing that interested him. He had paged trough the magazine two times when he heard his mom announce she was home. This instantly made him freeze in panic. Somewhere he knew it was ridiculous to panic now, his parents never came into his room and yet laying here in panties he felt so vulnerable and exposed. The fact that this stupid thong had the tendency to ride up his butt crack did no good either. After a few attempts off pulling it out he decided to just deal with it.

Done with the magazine he looked at his clock only to see that it was only 18:23 not even half an hour had passed so far. Knowing he was supposed to keep himself busy with this magazine for the remainder of the hour he started to page through it again. This time however he started reading some article about matching colours and patterns in summer outfits and one about must have accessories out of sheer boredom.

Eventually the hour was over, and Mark knew all too well what that meant. He was supposed to masturbate in his panties now. First he looked through the windows again but like last time there was no one to be seen. He really hoped he had done enough to prevent the flyers from being spread.

Reluctantly he lay back down and started fondling his soft cock in his panties. Mark closed his eyes and tried imagining the striptease his girlfriend had given him, but even so it took him a long time to even just get hard. Eventually though his cock did harden to a its full 7 inches. After that it luckily didn’t take too long anymore. As a lot of hormone filled guys his age he managed to cum within minutes of getting hard. Getting hard had been the difficult part with how mortified he was.

Now after his orgasm the shame and mortification set in harder than even before he had started masturbating. Fortunately he had his own bathroom connected with a door to his room so he didn’t need to risk getting out in the hallway to wash his panties. He quickly washed the cum out of them and hung them to dry in a hidden spot hoping to just be able to forget about the panties completely.

Of course that didn’t happen, the events of the evening haunted him until he finally decided to go to bed. Sleep did not come easy as he wondered if his acts had been enough. He was worried about the flyers being spread as well as the fact that he still wasn’t any wiser as to who was behind this.

In the house next door John was having a blast. When he had woken up this morning and spotted Mark in his panties he knew it was a perfect opportunity to finally get some revenge on that pathetic excuse of a man. His job as a home employed web developer gave him great freedom to do his work whenever he wanted. He basically just had to meet deadlines. It payed a nice buck as well and now it had even proven to be a very good tool to help extract his revenge. Making a website and a flyer was routine for John. It had only taken him about an hour or two to get the job done but it was very satisfying work.

At first his plan had been to just spread the site and flyer as much as he could but the more he thought about it the more he craved something more fulfilling. He didn’t just want to ruin Mark’s life. He wanted to destroy the whole image Mark had been up until now and to do that he needed a slower more thought out plan. So, his thoughts of blackmail were born. Knowing Mark, the instructions would have been terribly humiliating for him and that was exactly what John wanted. Watching Mark make a fool of himself and humiliate himself was so much more satisfying. Especially since it didn’t remove the opportunity to still post the flyers and website anyway.

For now though he would just stick with blackmail. It had given him some more great content for the site and while John wasn’t gay in the slightest he had to admit that the power trip he got out of this had made him quite horny.

It was especially amusing to see Mark check all his windows repeatedly. Like it mattered at all. Unbeknownst to Mark the file he had downloaded from the mail had carried some malware allowing John access to Marks webcam and laptop. The whole thing had been streamed to his television and there was no way Mark could even know.

Satisfied with how things had gone John opened another beer and put on some porn to jerk off to, shooting a big wad of cum in his boxers as he imagined how he would proceed his revenge. One thing was certain this had only just started, and things would only get worse for Mark from here on out.