(This is a teaser for an offsite post based in the universe of “Neighbourhood Terror to Sissy” reading that first might be advised.)

Intro

Victor was just a regular guy down on his luck. A month ago he still had it all, a beautiful girlfriend, a nice apartment and a decent paying job working for an accounting firm. The company he had worked for wasn’t doing so well though and as a result they needed to let some people go. He ended up being one of them.

It was a small disaster since him and his girlfriend didn’t have anything in regard to savings. They hadn’t even been able to pay this month rent yet as a month before they had made an expensive trip across the country to a huge but expensive metal festival. Both him and his girlfriend were huge metal fans. It was the same festival they had met at two years earlier and since then they had always attended it to celebrate their relationship’s anniversary.

He hadn’t expected to be out of a job a month after that festival though and so he was now in big trouble. For the past month since he lost his job he had tried to find a new one, often having several job interviews a day, but each time he was politely turned down. Maybe it had something to do with his long hair? He had always loved wearing his hair long. Right now it was even down to his back, a big mass of black curls. His girlfriend had often told him how jealous she was about his hair, seeing him head bang with it had even sparked their very first conversation. Apparently none of the people conducting the job interviews thought it was appropriate though.

Him being out of a job had also put a severe strain on his relationship. Something which was further fuelled by the treat of actually being kicked out of their apartment. Victor really needed a job fast to save both his apartment and his relationship. Desperately he searched through ads for any job he could possibly take to safe his current life. Sadly it couldn’t be something menial as he would have to pay two months or rent rather quickly and with a job as let’s say a server at a restaurant he just wouldn’t make it. Since his last job had paid well he had chosen an apartment according to his wage and so the rent was rather high.

Then all of a sudden a specific ad caught his eye. It had only just been posted and thankfully so cause judging by the ad it would soon be filled in and taken of line as well. It just seemed to good to be true. The only requirements were that you were male, it was for a modelling gig, but surprisingly no experience was preferred. It also paid 20k.

Immediately Victor dialled the number disclosed in the ad and a woman named Linda picked up the phone. “Hello, you’re speaking with Victor. Yes I call in regard to that modelling ad. I can come for an interview in 30 minutes?! Uhm no that isn’t a problem, I’ll be there. Yes I’m on my way. See you in 30 minutes.”

Putting down his phone Victor was quite shocked. This woman on the other end of the line sure wasn’t messing around at al. If he wanted to make it in 30 minutes downtown he wouldn’t even have time for a shower, he just had time to throw on his suit which wasn’t ironed yet after his last job interview.

Victor knew it made him look a little dishevelled but there was nothing to be done about that now he thought as he rushed out. Besides he wasn’t very hopeful he would get the job anyways. The ad asked for a male model and beside his long curls he was about as average as a guy got. He stood at about 5’9” and was neither muscular or lean. There was a little fat packed in his butt, gut and around his love handles, but nothing significantly. Just to much to call him skinny rather than average. He knew he didn’t have any qualities a model would need, but the offer was just too good to not at least try and go for. 20k would fix all his current problems and give him a few more months to find a job without having to worry about the rent.

28 minutes later Victor arrived at the address he had been given and immediately thought he had to be at the wrong place. Maybe this ad really was too good to be true, maybe it had all just been a prank after all this boutique called CC’s couldn’t be the place right? The main theme was pink and the outfits in the store front were all outrageous. Nothing he had ever seen anyone out on the streets wear.

The place instantly made Victor feel uncomfortable. He had always been somewhat uncomfortable around girliness and he actually hated the colour pink for reasons he couldn’t really explain. On that front his girlfriend was perfect, she mainly wore jeans and band shirts so she definitely wasn’t a girly girl to say the least.

In any case Victor decided to just suck it up and walk into the store. He really needed this gig after all. Maybe there was a modelling agency running from this same building? After all what did he know about the modelling sector? Nothing at all.

Entering the store a bell rung and he was confronted by row upon rows of these frilly clothes. It made his skin crawl so instead of focussing on the interior and the posters of girls modelling these clothes he just stared straight ahead to where a tall bombshell of a red-haired woman was approaching.

Linda walked up to the suited guy who had just entered her store figuring he had to be the one who had been first to answer her add. It kind of surprised her that he had even entered the store. Maybe he just hadn’t made the connection yet that he would be modelling these very clothes? It wouldn’t surprise her as her ad had been really vague but offering a big sum of money. A lot of guys would probably just walk away upon seeing the store they were supposed to have their interview so despite the big sum she was suspecting this search might take a while.

Even more guys would walk away once she explained that they actually have to model the very clothes in her store and get their pictures published on her website and in he catalogue. Then again this was exactly what she was aiming at. She really wanted to find a guy desperate enough to agree to this gig and then she would have some fun. If everything went really well she hoped she would get a new sissy toy out of this. Stephanie was pretty much fully trained after all and while she was starting to get some clients to sissify it still wasn’t the same of getting to do it herself.

“Ah you must be Victor, the one I talked with on the phone regarding that modelling gig? Welcome, now if you could please follow me along into my office so we can discuss the terms in peace.” Linda said shaking his hand and giving him a quick once over before turning on her heels and walking straight to her office. There was a lot of work on this guy to get him to the point where she actually wanted to use his pictures, but that work was half the fun. Now it was onto the next phase to see if he was desperate enough.

She had taken down the picture frames of the steps in Stephanie’s transformation. After all it might shock a potential new sissy too much and that was something she wanted to avoid. At first at least. First she wanted to test how far she could push one of her potential new sissies.

“Here have a seat Victor.” Linda said rather demandingly pointing to a chair in front of her glass desk. Without skipping a beat Victor took a seat. He couldn’t quite put his finger on it, but there was something very imposing about this woman and it wasn’t just the fact that she towered over him in her high heels.

“So Victor, tell me a little about yourself? Why are you here? Why did you reply to the modelling gig I put up an ad for? What motivates you? Have you brought your resumé?” Linda fired a load of questions at him. None of the questions were out of the ordinary for an interview, but Linda’s tone did manage to make him feel awkward and small in a way. It felt rather uncomfortable, but once again Victor decided to suck it up. Surely he was just imagining things right?

“Uhm well like I said before, my name is Victor. I’m thirty years old and after leaving my previous job I have been looking for a new challenge. I really wanted to broaden my horizons so your ad instantly jumped out to me. Modelling is something completely new to me and I would love to try it out especially since your ad specified you were looking for someone without experience. I sadly didn’t have time to bring my resume since I could come here on such short notice.” Victor explained somewhat nervous. He hadn’t felt nervous about an interview in a long time, but the intense way Linda stared at him like she was dismantling him really made him nervous.

If it wasn’t for his dire need of the promised 20k he would have probably apologised and said he wasn’t ready for the job already. Sadly that wasn’t something he could afford right now. Like before he just had to suck it up. It was a hard exercise for him as he usually didn’t bow for nobody. He might not be the strongest guy physically, but he certainly wasn’t one to just give in.

Right now telling Linda off was just not worth it though. He could take some discomfort for such a sum of money. “I don’t need to hear any excuses Victor, just answer my questions so when I ask if you brought a resumé just say no and save some time for the both of us.” Linda snapped as she watched Victor closely. She could tell he was having a hard time to keep himself from telling her to fuck off when she took her usual authorative condescending tone. Although at the same time she could also tell that he wouldn’t just let her walk all over him like she was able to do to some of her clients like Marcy.

Marcy had been such a godsend. Since that perv of a John had made a website for the sissy, the visitors on her own sadly rather not all that well worked out website with a few unappealing stock photos had exploded. Despite the state of her site it had already lead to a few new clients, but she was certain if she worked on a more professional site and better marketing, she would get another big boost in customers.

A professional site and strong brand needed a face and good customised photo’s showing how her numerous outfits looked on a real person. Although that was her main concern it was also just a reason for her to take on a new sissy to train personally. Ordering Stephanie around was still fun, so was helping out in sissifying her clients, but she really craved a new project of her own right now. Coupling a necessity to a pleasure was always nice.

“Anyways Victor, your motivation sounds perfect. I specifically asked for someone without experience since it’s always such a pleasure to introduce someone new to the modelling world and lifestyle. In that regard I think you’re a perfect candidate especially your hair will work perfectly for this gig.” Linda said with a smirk, if Victor only knew what exactly she meant by introducing someone new to the lifestyle he would probably have ran already.

Victor was quite surprised when Linda pointed out his hair as his current best attribute. It was the exact thing he had suspected he was discriminated on during all of his previous job interviews. More importantly though Linda seemed to be buying right into his lie. Modelling didn’t interest him one bit and he didn’t look to broaden his horizons. It just sounded better than being desperate.

“I’m sure you know the proverb no pain, no gain right? Well this is something that is especially true in the modelling industry. Since you’re honestly not in the best of shapes we’ll need to use some foundation garments. We’ll also need to apply some makeup, but don’t you worry about that, the support staff I’ll arrange in the studio will take care of everything you need.” Linda said giving Victor a bigger glimpse at the kind of shoot he was signing up for without giving it all away yet.

These statements shocked Victor somewhat, although he rationalised that he had heard about male TV hosts needing a dusting of makeup before shows as well so their head wouldn’t look like a shining beacon on camera so it made sense for a photoshoot as well he guessed. He didn’t know what the foundation garments were about and he felt somewhat offended by Linda’s blunt statement, although he knew he was nowhere near model shaped.

He was just about to ask for a clarification of the foundation garments when Linda spoke up once more. Victor had put up with quite a lot so far so she guessed he had to be at least somewhat desperate. Now it was time to see how desperate as she would reveal the kind of shoot he was signing up for.

“Now Victor, I do think you’re the man for the job and I do have the contract ready for you. If you could just sign at the bottom of each page.” Linda said shoving a stack of papers across her desk with a pen laying on top of them before dropping the bomb. “With some work and the right makeup I bet you’ll do great modelling the dresses in my store.” Linda said giving Victor a confident smile.

Victor had only just picked up the first page of the contract to start reading when Linda had said those fate full words. His face went pale in shock before going red in anger. “Y… You’re crazy not even a fucking million dollars would be enough to get me to consider putting one of those dresses on. You can just take your fucking contract and shove it up your…!” He screamed not finishing his sentence as he just dropped the first page and rushed out of the store, his blood boiling in anger.

Linda had remained calm during his outburst, but as soon as she heard the door of her shop close she cursed out loud. “God fucking damnit. I really needed that new model and a new fucking project! Stephanie! Get your fucking ass in here and bend over my desk!” Linda shouted loud enough for her sissy stepson who she had ordered to stay out of the picture at the back of the store to hear. God she really needed to blow off some steam.

Taking her strapon out of a nearby cupboard she was ready to take out her frustrations on Stephanie’s ass. Stephanie knew better than to say anything. She had minced into the office as fast as she could, bent over the desk, raised her skirt and lowered her panties as Linda didn’t waste a minute to shove the rather large strapon up her ass giving it a hard slap.

“I nearly had that fucking bastard! Just a little longer and he would have signed the contract! When another fool drops by I won’t disclose what that fucking shoot is about until he has signed! Fuck I should also rework that contract make it a little more airtight while I’m at it!” She screamed as she pounded Stephanie’s bottom with every word, venting her frustration. Poundings like these always made Stephanie’s ass very sore, but at the same time she couldn’t help herself from having at least one orgasm from them.

Chapter 1

While Linda was working off her frustrations Victor was fuming himself. He couldn’t believe the nerve of that Linda woman, the nerve to even suggest he would touch those horrid dresses, let alone wear them for a shoot. Fuck that 20k payout. Besides it just wasn’t wroth it, he should have some more time to look for something else.

Arriving at his apartment victor instantly went pale, his anger replaced with worry as an evection notice was posted on his door. Instantly he tore it down afraid of anyone especially his girlfriend seeing it. with their recent trouble this could have been the straw that broke the camel’s back and he didn’t want to lose her. Although it was a bit of a conservative view he felt it was his duty as the boyfriend to provide. Besides he couldn’t really expect his girlfriend to provide since she still studied.

Reading the note he saw this was just a first warning. It said he had a week time to come up with this month’s rent and that he couldn’t be late on next month’s rent either which was also in about a week time. Throwing his hands in his hair victor got back behind his computer and franticly started searching for another job.

His whole day of searching was rather fruitless and on top of that him and his girlfriend had yet another argument. Luckily he had been home first so he still had been able to hide that eviction notice. He didn’t want to know the shit storm that would come his way if she had found it. He would just hide it for now, find a job an fix it. He would fix it and she would never have to find out, or at least those were his thoughts.

The day after Victor started his search from the early morning but after numerous calls to various firms, he still wasn’t a step closer to finding a job. The week he had before his eviction became a reality, became shorter and shorter while his search became more desperate.

As his desperation grew so did the thought of actually accepting Linda’s offer. As disturbing as it was it still was better than losing his home and his girlfriend. If he didn’t find a job real soon his life as he knew it would be over. Maybe it was worth considering the option of just modelling a few of those horrid dresses and getting it over with. Maybe he should just put his ego aside for the greater good this once.

Besides, it was not like anyone would ever know about that shoot right? He didn’t know a single person who would ever come in contact with a store like that so in that regard he probably didn’t have to fear exposure. At least that was how he reasoned with himself as the chances of actually having to agree to that shoot as a last resort continued to increase much to Victor’s horror.

The next day Victor had another fruitless morning of job searching. With a few more days left until his eviction which would surely lead to losing his girlfriend as well, he decided to cave in out of desperation. The more he thought about it the more it seemed like his only option it would be just a one-time thing and no one had to ever find out about it. With 20k he could safe his rent and relationship for a few months at least, more than enough time to find a good job and end his troubles once and for all.

With a small heart he decided to call Linda again, praying that the job would still be available while also hoping it wouldn’t so he wouldn’t have to go through such an embarrassing shoot. Despite being nearly certain that this was his only shot at saving his current life he still wasn’t sure he wanted to go through with this. “Hello Linda, yes it’s about the shoot. I have reconsidered. Oh you have a few other candidates for the job by now? None of them have signed just yet and if I’m the first to sign I get the job after all? Great okay I’ll be on my way.” Victor said with a dread filled voice.

Linda smiled as she put down the phone. During the days her ad had been up Victor had been the only one to actually show up on his interview. Apparently her store front seemed as too big a scare off for other potential candidates. It had only made her frustrations over letting that very first guy go grow. Especially now that she saw the ever-increasing traffic on her site, all people who got to see the lacklustre website.

Her frustrations had risen to the point where she had hired a private detective to find out more about Victor. She wanted to find something anything to manipulate him into taking the job and ensnaring him in her trap anyways. After only a day she had gotten a full report on him full of juicy details. She found out about him losing his job, the trouble finding a new job, his approaching eviction, the difficulty finding a new job and even the relationship troubles.

Apparently Victor was an even better candidate than she could ever have hoped for, his situation was desperate. As soon as she had gotten the report she was nearly certain that Victor would come back to her sooner or later and she had just been proven right.

Since it had taken a few days for him to come to the conclusion that he had no other option than to take on this job Linda had had all the time in the world to prepare. This time she wouldn’t let him go anymore. With the help of a lawyer friend she had changed the contract to trap him in a number of ways, all that rested now was to wait for him to come by and sign his fate.

About half an hour later Victor finally arrived. Filled with dread he entered that overly girly pink store again. Linda was already waiting for him and guided him straight into her office, shoving a stack of papers under his nose. “Here, just sign at the bottom of each page.” Linda said coldly giving him a stern look. Ashamed by his outburst last time and not wanting to screw this up Victor didn’t object to her short cold treatment.

Picking up the first page he started to read, but Linda interrupted him. “Do you want this gig or not? I’m going to be straight with you. The only reason I’m giving you another chance is because I’m pretty certain you’re the perfect fit for our shoot. After how you screamed at me last time I’m not really looking forward to work with you, but for the greater good I want to give this another chance. So what is it going to be? Are you going to sign or do I just wait for the other candidates to sign?” Linda asked putting Victor under pressure.

There were no other candidates, but Victor didn’t know about that. She just had to convince him to sign quickly and without reading as the terms of the contract would put even this desperate guy off. Although Victor was against signing things he hadn’t read first he did so, not able to risk losing this second chance. He didn’t know it yet, but page after page he signed his life away, working himself deeper and deeper into Linda’s trap without knowing it. Linda just watched the whole thing with a big smile.

“Alright Victor, now could you please follow me along so we can start with a first try-out shoot to make you a portfolio? This is just to have a basis on which I’ll make my final decision on who I want to take on as the model for the shoot.” Linda said with a big smile on her face.

“What?! So you want me to do two shoots? No way, just let me know when the shoot is, I’ll show up and we get it done okay? After all I only agreed to do that shoot.” Victor sad sharply, having to shoot once would be bad enough already, but he needed the money.

“Now Victor I thought you reconsidered about the shoot. The way I’m seeing it you don’t seem all that enthusiastic about it at all. You know you don’t have to do this right? I can always take one of the other candidates. Of course you would give me no choice but to sue you since you need to deliver a shoot relevant portfolio as stated in the contract you signed. Not delivering one now would be considered contract breaching which would result in a claim of 20k or jail time if you can’t pay up.” Linda casually said watching the shock wash over Victors face now that he realised the contract was in fact quite severe.

“You are right that we didn’t agree on this trial shoot though. It’s nowhere in the contract, it was just me doing you a favour, after all I doubt you have any pictures for a shoot relevant portfolio? Of course if you do and have a phone filled with pictures of you in girly delights then go right ahead and craft a portfolio with that. It needs to be sent in by tonight though.” Linda calmly stated watching the dread on Victor’s face grow.

“Of course you also have the option to buy an outfit here and ask someone to snap a few pics for you on such a short notice. The choice is yours. I just wanted to help by lending you an outfit and a hand with snapping some pictures. I’m even willing to make the portfolio for you so you won’t risk being late on sending it in. So what’s your choice?” Linda asked with a big smirk knowing she had Victor right where she wanted him.

Victor’s face had gone completely pale as he realised the deep shit he was in. he should have insisted on reading that contract, but he had needed the money so badly that he had assumed that it was just a contract for that shoot he had already justified as necessary in his head. A claim of 20k was something he just couldn’t afford. It would send him to jail on top of losing his home and girlfriend.

“I…I’ll go along for the trial shoot I guess.” Victor eventually stammered out giving in to the pressure that had just been put on him. He didn’t like it one bit, but shooting once or twice wouldn’t really make the difference now would it. He had fucked up and now he needed to just suck it up and deal with it. This trial shoot surely was an inconvenience, but it was just this and then the real shoot and he would be done with it all forever, able to safe his relationship and home.

“Great, now come along, we need to pick out a proper outfit for you to model, but don’t worry. I’m sure we’ll find you something perfect to wear to give you a good winning chance with your portfolio. Not all applicants are as lucky as you are you know.” Linda mocked knowing full well that the last thing Victor wanted was to wear one of her dresses. The only reason he was in this was for the money and now because of his contractual obligations.

Having come this far Victor really hoped he would get the gig and not have to suffer all this embarrassment for nothing. He would have to give this trial shoot his best wanting or not. He couldn’t afford not to be chosen. Victor thought not knowing that he was in fact the only candidate. Linda didn’t plan to tell him either she needed him motivated for this trial shoot, well she didn’t need it, it would just be more fun to see Victor force himself to cooperate.

In fact there was still a lot Victor didn’t know about. What she had disclosed about the contract so far was only the beginning. If Victor had known the full extend of the contract he would have ran already and chosen prison time. She had seen it the moment he had entered Victor wasn’t the kind of person to easily bend to her will like Marcy was. He was a guy who did what he had to, to work himself out of this difficult situation.

The knots Victor felt in his stomach only grew worse as he followed Linda out of her office and into her store. Passing the rows upon rows of frilly colourful outfits his dread about what he was about to do only grew, but so he rationalised, he just had to suck it up for now and deal with it. This was only a small discomfort to pay for saving his home and relationship. After all it were just clothes, right? As bad as they looked they were just pieces of fabric.

“Alright, let’s find you something to wear.” Linda stated as she rummaged through the racks they passed by. Victor had seen nothing he would even consider wearing for a joke, but then this was no joke. This was his home and relationship that depended on his actions.

After a moment of rummaging Linda shove a hanger with a big mass of pink fabric in Victor’s hands. Just looking at it made him feel slightly sick. “This should do nicely, hold this!” Linda said. Victor wanted to protest, but looking around he didn’t really see a better alternative. Even the blue pieces were made of a light pastel blue making it seem just as girly as the pink. This is just a piece of fabric. He repeated in his head.

As they made their way further into the store Linda just added more hangers to the one Victor was already carrying. All of them kept to a certain pink and white theme although as they disappeared into the mass Victor was already carrying he had a hard time figuring out what each item was for.

Linda was having a field day however. Sizes were up to guessing for now, but she could always get a different size if the one she had just handed him didn’t fit. In a few minutes she would finally get a first good look at what her new sissy project would look like.

While Victor wasn’t weak he was slowly having a hard time carrying the hangers. They didn’t allow for the best of grips and the collection of clothes was actually surprisingly heavy. So much that it was a relief when Linda finally announced. “That should do, now just move behind the curtain and we can start.”

Looking up Victor was shocked all over again. He had walked looking down to try and control the mass of fabric he was holding so he hadn’t seen where they had arrived yet. Instead of a changing room like he was expecting they stood in front of a small stage, the back half closed off by a big pink curtain. Linda had to be joking right?

“Now there are a few steps there at the back behind the curtain with a chair and a few hangers. Why don’t you change into the lingerie I handed you there? Oh and be a dear and tell me your shoe size will you? So I can get you a nice pair of heels to go with that outfit?” Linda asked with a smile only watching the shock on Victor’s face grow? It was clear Linda wasn’t joking and now she wanted to get him heels? Where would this end? He thought horrified.

(This is another one of my stories running up on my Patreon. If you want to see more of this and many other stories, please consider following me there. https://www.patreon.com/Fibaro This story was commissioned by one of my Patrons and is still running.)