Neighbourhood Terror to Sissy Pt. 04

The next morning Mark was woken up by a loud mechanical voice. "Wakey wakey sissy, time to start your day, and what better way to start it than with another wank." Mark groaned loudly but he did as the voice said anyway. With a sigh he grabbed the boxers of his night stand and Pulled them over his head once more.

Since this had started he had spent countless hours inhaling the scent of these nasty boxers. It wasn't anything new anymore, but it remained embarrassing. His cock was already standing at full attention in the now crusty panties as he once more started wanking.

At least it was easier now than it had been the last time last night. He came within a few minutes after which he got up. Heading to the bathroom he almost made the mistake of standing up to pee, but just in time he managed to correct himself with bright red cheeks. Once more wiping after he was done.

Being done he carried the boxers to the sink and ran some warm soapy water. Handwashing the boxers and his panties had become part of his morning routine by now. The boxers went back in their bag and the panties got hung up to dry. The look of these ultra girly panties still made him blush. Once he got that over with he stepped in the shower.

The warm water felt good on his skin, but as he started washing himself he felt awkward. Running his hands all over his baby smooth skin felt so wrong especially knowing that he was being watched. With that in mind he finished his shower as fast as he could.

Just as Mark was stepping back into his room the speakers turned up again. "Good sissy, now I think it is time you do something for me don't you think? After all I have invested in giving you so Many panties and a nice waxing at the salon, it's only fair that you get to invest as well. So, by this evening I want you to get a full set of lingerie, panties, stockings, and a bra at minimum oh and the bra needs to be at least a D-cup. Make sure it is a set I like or else..." Just like that the mechanic voice stopped once more.

Shit, how was he supposed to get that done? What the hell did that guy even like? How was he even supposed to know? Mark thought in panic, he had no idea what the "or else" meant, but it couldn't be good.

It took a couple of minutes for Mark to calm down but once he did he was a little more clear headed and actually able to think of a solution. Clearly whoever the perv behind this was would like the panties he had given him, so those would be his reference to what kind of lingerie he would need to buy. Looking through his panty collection, he realised that while they were all different styles and colours, they all had one thing in common. All his panties were over the top girly, well true sissy panties for lack of a better word. They weren't meant to be racy but rather cute and eye catching. The only really racy panties he had were those of his girlfriend.

Not wanting to have to roam lingerie stores until he found a set that he hoped would be satisfactory to his blackmailer, Mark decided to do on online search first. He kind of remembered that Lisa bought her panties mainly at Victoria Secrets, which made it the only brand he really knew. Maybe he could place an order to be picked up at the shop? His blackmailer would be none the wiser and he wouldn't have to roam the whole store. He could just say he needed to pick up a package for his girlfriend.

Maybe this would be easier than he thought after all. A quick look trough the site left him disappointed however. Sure, they had some panties that looked cute and colourful, but nothing nearly as exaggerated as his own panties. Some might cut it, but only barely so and he didn't dare face the consequences of having his purchase declared unfitting. Besides that, he also couldn't find a single pair of stockings, so he would need to hit another shop as well.

Thinking about it going there wouldn't be smart in the first place. After all every girl he knew probably shopped there which would mean that his chances of getting discovered were quite high. Hell, for all he knew some girl from his class or the skate park even had a vacation job there. It was the only lingerie store he knew by name though so if not there, then where was he supposed to find that set?

he couldn't really ask his girlfriend, could you? No, no way, no one could find out about this. Then all of a sudden, an idea struck Mark. He really hoped this would work, it was certainly worth a shot. He thought and laid out all the panties he had received. With a few quick swipes he took close up pics of all the panties.

So, lets hope that a reverse image search will point in the right direction. A few clicks later Mark is surprised to find a website of a shop called "cc's boutique" on there he finds pictures of some of the exact same panties among a lot more stuff like that. To make things even weirder the shop is just at the edge of town even if the website looks a bit shady. There are tons and tons of over the top lingerie featured on the page, but there aren't any prices, or options to order it.

He would have no choice but to go there in person. On the other hand, it really didn't look like a store that would be visited by anyone he knew. They only featured lingerie of a very specific taste it seemed.

Maybe if he went now while it was still early he would be there completely alone. Not that a shop with lingerie like that had a lot of customers to begin with he guessed. Anyways, he had already missed a day at the skatepark and missing another might raise questions. Getting this entire thing out of the way as fast as possible was the best course of action.

With that in mind Mark got dressed and started heading out. At least this time he didn't need to wear panties out. It wasn't much considering what he would have to do, but it was something. These little things were the only once he could kind of find comfort in.

A short walk later he hopped on the bus and was surprised to find out it stopped right in front of the store window. This shop had really managed to pick a good location, he thought. Which was probably necessary because the only reason he could see some one walking into this store was out of curiosity. Well and of course if you had no other choice like he did.

The store front had big windows with mannequins dressed in the most elaborate dressed Mark had ever seen. All beneath a soft and dark pink striped headboard with the name "cc's boutique" written in a pearly white cursive.

For a moment he considered walking away, simply looking at this store and its wares was enough to make him feel slightly nauseous. Would he really need to buy a set of lingerie here? Well if he wanted to appease his blackmailer he would. It was not like he could think of a better option really and this store looked empty enough. The personnel wouldn't think anything of it if he said it was for his girlfriend, right?

With that in mind Mark braced himself and stepped in, a loud store bell rung. Once inside he felt a bit lost. There were a ton of racks all filled with bright colours and over the top girly dresses and other clothes. How the hell was he even supposed to find his way in here? This shop looked huge. Way bigger than what he had expected.

Mark was still staring around in awe when a big imposing woman suddenly appeared in front of him. She looked equal amounts hot and scary. If Mark had to guess, he would say she was somewhere in her late thirties to early forties. She simply radiated authority with her curvy hourglass figure and her stern outfit. Her white blouse with the top button undone revealing a good portion of her big breasts, the black tight-fitting pencil skirt hugging her ample bottom, the seamed sheer black hosiery giving another dimension to her long toned legs and the black stiletto heels making this tall woman look like a giant, all made her look like some sexualised version of a teacher. Especially with her long wavy red hair and glasses.

An erection inevitably grew in Marks pants while he gulped at the same time. This woman was every man's wet dream, if only he had seen her under different circumstances. Not that he would have had a chance, but what would she think of him now? Confronted by a woman this gorgeous his nerves only increased.

"Hello, my name is Linda. I'm the owner of cc's boutique, what can I help you with?" The imposing woman asked. Her tone didn't sound friendly or happy at all. Mark would have guessed a shop owner from a shop like this would have been happy with any client. Yet Linda's tone had a certain air of superiority about it. While due to her height she literally looked down on him she also talked down to him.

It was all rather demeaning which only made Mark blush and feel nervous even more. "Uhm, I... I am looking for a lingerie set for my girlfriend. I need a pair of stockings panties and a D-cup bra." Mark stammered out reciting what he needed to this woman.

Linda Just raised an eyebrow. "For your girlfriend you say? Right and I'm the pope. Let me guess, your girlfriend is about the same height and size as you as well?" She asked with s shit eating grin clearly starting to enjoy herself unlike with her greeting.

"I...It's true, I..." Mark stammered, but instantly got cut off.

"Shut it sissy!" Linda shouted leaving Mark stunned. Did he really look that much like a sissy? How did this woman see right through him?

"No woman in her right mind would ever buy, much less wear stuff like this. Of course, it is perfect for pathetic sissies like you. Why did you think this store was called cc's?" Linda asked with a smirk seeing the realisation dawn on Mark that when it got said out loud it sounded and awe full lot like sissy's.

For as long as she could remember Linda had gotten a thrill out of humiliating smaller and slender boys. She basically had two types of guys she loved. Big strong men who could give her a thorough fucking and these fragile boys to humiliate. The first type wasn't really her type but more like a help to get everything out of the second type. Linda got her main rush and kicks out of these weaker men which she simply loved pushing into sissyhood. Her first type merely served as a help to humiliate her victims even further.

It was a game she had played a lot in her college years pick up some scrawny looking guy which wasn't hard with her looks. All men wanted her, and the scrawny ones were especially easy. Most of the time they couldn't believe their luck to be able to go home with such a gorgeous girl. Especially since most were still virgins.

Seeing the looks on their face when she told them how hot it got her to see a guy confident enough in his masculinity to put on some of her lingerie was all it took to get them to do exactly that. After which she would call in one of her hunks on quick dial who all knew they weren't the only ones. They didn't really care either Linda was one of the hottest girls on campus and they would never turn fucking her down.

As she got fucked she never looked at her hunks. She got her kicks out of ordering the wimps to masturbate in her lingerie demeaning them the whole time as she got fucked while having orgasm after orgasm. By the end of her first year she had done this to every wimp in her class. Since all of them were too ashamed to talk about it her next victim never had a clue until it happened. Not even the ones who were friends with her previous victims.

Over the years her need to humiliate and sissify had only grown. A couple years back she had married some rich widower with prostate cancer. An easy target for her, specifically picked for his wimpy son. She never had to have sex with him due to his illness and he wasn't long for the world anyway. During her few years as his trophy wife she had made sure to be appointed the full inheritance and guardianship of his 18-year-old son until he turned 21.

She had spent a full year completely sissifying her stepson before she opened this shop. Up until her step son she had never been able to do more than make her victims wear some girly outfits, maybe some waxing or makeup, but none would return for more. Her stepson didn't have the luxury to run away which allowed her to take her fantasies to the extreme. Resulting in having a completely obedient sissy servant which she doubted would ever be able to live a normal life by now.

While she still managed to humiliate her sissy stepson, the intoxicating thrill was out of it. She needed someone fresh and new, which had led her to opening this shop. The idea had struck her out of the blue and she really hoped it would find success. Not really financial success or anything the inheritance was large enough to warrant she didn't have to work a day in her life again and to keep this rather big store running even if she would have no clients. Income was not the motivation behind this store. The only reason she opened it was to find fresh meat to sissify.

By now the store had been open for two weeks and Mark was her very first real client. Well technically John was when he bought those panties at first, she had been disappointed seeing that slob of an old man walk in but upon questioning him and gaining his thrust she had found out what he was doing with the panties. All the lingerie and outfits in the store were designed by her and custom made so they all were rather expensive. She had however offered him a full refund if he sent the sissy to her. Money wasn't an issue, but she wanted part of this.

While John hadn't really ordered Mark to go here precisely the guy had wound up here anyway which was enough for Linda to give John his refund. First, she would take her time savouring the humiliation radiating from this fresh sissy boy though.

"Alright, follow me. The lingerie is right this way sissy." Linda said to Mark grabbing his shoulder firmly and pushing him out in front of her.

"What, n...no, this is a mistake. I'll find somewhere else. You're right my girlfriend wouldn't like this lingerie." Mark tried saying in a desperate attempt to get away and convince this lady that he really wasn't a sissy.

Furiously Linda spinned him around and grabbed his earlobe with a great amount of force. "Listen up you little twat, you came in here in my shop asking for a nice set of lingerie for your sissy ass and that is exactly what we are going to get you. Everything about you screams sissy, so stop lying and start moving or I swear you will be sorry." Linda said angrily before dragging Mark along by his ear. This was getting her so hot. The thrill of a new boy to sissify.

On their way trough the racks of clothing Mark spotted a pretty girl around his age. She looked gorgeous although a bit ridiculous. She looked a bit smaller than him with a slender girlish figure. Her working uniform was the same as Linda's only her heels were higher the skirt was way shorter revealing her stocking tops and the blouse was made of satin with a high collar, ruffles running along the button line and at the sleeve cuffs. In the back of the blouse there was a big black satin bow starting right underneath the girl's neat bob cut in a matching red like Linda's hair.

"Help, this woman is crazy. You have to help me." Mark screamed at the girl who just looked up to him, blushed then went straight back to sorting clothes on the racks.

Her height and way she stayed in shape had always helped Linda push around wimps, she was simply much stronger than the guys she targeted, and this time was no different. The thrill of pushing this unwilling boy around was delightful, the fact that she had needed to wait so long for her first client made her all the more ruthless.

The corner where there would be a changing room in a normal store feature a small platform, a big mirror on each wall, two spots aimed perfectly at the platform and two big comfortable recliners facing the platform. There was a curtain which could be rolled down from the ceiling but only using a remote Linda had. This was no changing area but rather a presentation area.

Mark didn't have much time to take everything in however. Linda just dragged him over to one of the recliners and sat down dragging Mark over her lap by his earlobe. With a rough motion she pulled his pants and boxers down to his ankles revealing his smoothly waxed bottom which was still slightly bruised from yesterday's spanking at the hands of Suzan. His cock which was somehow still erect found its way between Linda's soft nylon thighs.

"Oh my fucking god, by the looks of it you simply don't learn do you sissy?" Linda shouted at him hinting at how he clearly had already gotten a spanking. "Just fucking look at you claiming not to be a sissy. You're smooth all over and even sporting a stiffy from all these pretty clothes around you. You're probably the biggest sissy I have laid eyes upon and that means a lot." Linda taunted.

"Now let's see, you lied to me, kept lying even after I saw through it, called me crazy, and insulted me with your perverted erect clitty. Those are four crimes that need to be punished with let's say 10 spanks each plus an extra 10 for being a pathetic sissy giving you a total of 50 spanks so let's get started, shall we?" Linda said vindictively rubbing Marks poor buttocks savouring his fear and humiliation.

Mark was almost out of his mind with fear. He instantly had flashbacks to yesterday and started whimpering and pleading. "Please, no I beg you. I will be good I promise please!" Mark screamed out near crying.

"Unbelievable, you even whine like a fucking sissy. Now I want you to count and thank me for every spank. The ones you miss don't count." Linda said delivering a first harsh blow to Marks bottom. Mark was so shocked that he didn't even have time to count before Linda delivered her second blow after which he yelped out "two!"

"No you fucking sissy, the first one didn't count so start from one and say thank you Miss Linda after every count." Linda said annoyed as she delivered 5 hard blows in rapid succession before delivering a sixth more controlled one.

"One, thank you Miss Linda." Mark cried out. He barely had time to say those words before another spank landed.

"Two, thank you Miss Linda." He cried out in pain. His bottom was already burning and still tender from yesterday. He didn't know how he got into this mess, but he just wanted it to end so no matter how bad the pain he just kept dutifully counting, knowing that reasoning would only get him more trouble.

Every spank made his erect cock slide a bit deeper before retreating back up between Linda's soft warm nylon covered thighs. To his intense shame Mark felt an orgasm slowly building despite the pain. Each spank brought him a bit closer. It was Eventually at the count of 17 that his penis started twitching before spurting its load between Linda's thighs.

"You fucking gross sissy, we'll deal with this in a moment!" Linda shouted while she carried on spanking. It took a couple of hits until Mark recovered enough to carry on counting. After that he continued without incident for the remainder of the spanking. His cock continued sliding between the now slippery thighs as he had once again reached a new height of humiliation.

By the time he finally reached 50 his butt fell like it would fall off, or at least Mark wished it would. He was loudly sobbing and truly defeated. Due to all the stimulation of Linda's slippery nylon thighs his cock had grown hard again, but instead of letting him go she kept him firmly in place. "Stephanie, come here a moment please." Linda called out calmly as Mark heard a fast-clicking pace of heels approach.

"Yeth Mommy, what can I do for you?" A soft girly voice asked. Mark could only see the incredibly high heels and stockinged legs from where he was laying but he recognised them immediately as the ones from the girl he had called out for help to. This was her daughter?!