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Neighbourhood Terror to Sissy Pt. 06

Story Info
A second visit to CC's brings a whole lot of humiliation.
5.9k words
4.65
54.2k
39

Part 6 of the 49 part series

Updated 06/09/2023
Created 02/23/2019
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Mark's night ended up being a very restless one. The constant rubbing of his sheets against his nylon covered smooth legs as well as the feeling of the silky material of his panties all around his bottom and chest felt very sensual. He was embarrassed to admit it, but it actually turned him on. The worries combined with the horniness formed a potent combo to keep him awake. He knew that masturbating again would probably solve his problems, but he knew what he had to do when he masturbated so he chose to just endure it.

Over the night he had managed to drift of a few times giving him at least a couple of hours of sleep. Yet by the time he decided to just start his day he was still tired. It was quite early on a Saturday morning which went completely against Marks nature of sleeping in, but he had had enough of all the twisting and turning.

Reaching over to his nightstand to grab the worn boxers Mark felt sick when his hand suddenly made contact with the lifelike dildo. It did make him remember that he probably should kiss it first before getting on with his masturbation and handwashing morning routine. For a moment he thought he might get away with not doing anything but washing everything, after all what were the chances that whoever was behind this was up this early as well?

If his blackmailer was asleep then he wasn't being watched, but what if it was on record, or he was awake anyways? In the end his paranoia over his blackmailer knowing everything he did won out so reluctantly he leaned over his nightstand to give the tip of the dildo a quick peck, shuddering as he did so.

At least it was over now Mark thought as he pulled the smelly pair of boxers over his head. His own cock instantly went from half erect morning wood to rock hard in response to the smell. Mark didn't think anything of it however. He just reached his hand inside his still somewhat moist panties and started masturbating, cumming within three minutes.

With his by now usual morning masturbation session over Mark got up and pulled the boxers with the very familiar scent of Johns cock off his head. He was still wearing the full set of lingerie with the now cum soaked panties as he walked to the bathroom, holding the dirty pair of boxers in his hands. He felt just like the sissy his blackmailer constantly called him.

Once inside the bathroom Mark stripped out of his frilly lingerie and started running some soapy water. Even without the lingerie he still looked like a big sissy due to his completely smooth body and the pastel pink heart of pubic hair sitting above his cock.

Now that he had a lot more items to wash, it took a lot longer to complete the tasked. The increased number of items hung out to dry also made his bathroom look like a girl's bathroom. Afterall you could easily look over a pair of panties, not so much a pair of panties, stockings, a girdle garter belt and a bra. All he could do about it though was sigh and take his shower.

Fresh out of the shower he went to his wardrobe sighing again when all he saw were panties in his underwear drawer. It was the very first day that he opened his drawer with only panties to choose from. He didn't really look through them, they were all panties which made them all just as bad in his eyes. He just grabbed the first pair, a baby blue silk pair with lace detailing and put them on.

He finished dressing in his usual baggy clothes and worn out sneakers, but he skipped putting on socks. He still remembered too well how Linda had kept his boxers and socks last time and after losing all of his boxers yesterday he didn't plan on losing his socks as well. Sure, walking sockless in his sneakers was slightly uncomfortable, but there was no way he was going to put on the stockings instead.

At least his parents were still asleep. Him heading out was nothing new and no one would probably question or know where he was headed, yet he felt so self-conscious about it that he was glad his parents were still sleeping.

Mark was almost at the door when he remembered the big pink bag. Linda had told him last time to bring it with him or there would be consequences. Probably another spanking, Mark thought with a shudder. The humiliation of being bend over Linda's lap and spanked was as painful as the spanking itself had been.

With that in mind he headed back up to his room and shoved the bag under his t-shirt, so no one would see it. He dropped the plastic bag with the boxers in the usual hiding spot for his blackmailer to pic them up, then jumped on the bus to that dreaded lingerie store. It was still calm on the bus, but then again it was still early as well. He just hoped he would also be so lucky later on in the day when he left the store.

The dreaded moment of arrival came way to quick for Mark. He knew he didn't want to go back into that store, but he also knew that it was either this or the whole world knowing he was a sissy. What would Linda think if he headed back in there after having been here only yesterday? Well did it really matter? Linda clearly had a very strong idea about him already.

Sighing deeply Mark pushed open the door making the bell ring, the nerves were coursing wildly through his stomach and for a moment he just thought about leaving again. Was this all really worth it?

Before he could make up his mind and leave however he saw Linda approaching him with a big smile and large confident steps. "Good morning sissy, seeing you yesterday I just knew you would be a loyal customer, but this? You must really be one desperate sissy. It hasn't even been 24 hours yet and here you are again." Linda said with a slight mock in her tone.

As soon as she closed in on the embarrassed guy she grabbed a firm hold of his arm and started pulling him towards yesterday's corner stage again. If Mark had wanted to leave he had certainly missed his chance. He could tell that there was no way Linda was going to let him go unless it was with at least one other set of lingerie.

"So let me guess sissy, you bought your first set of lingerie yesterday and you found out that you were just born for lingerie. You can't get enough of it and now you are back for more?" Linda said, she knew the real reason since she had asked John about it, but she didn't really care much and taunting the sissy is so much more fun anyways.

"N...no, that's not it at all." Mark stammered softly.

"Then why are you here sissy? I don't know if you noticed but this store doesn't sell the newest sports jerseys or whatever guys are into." Linda replied sharply.

"I... I'm here for..." Mark stammered hesitantly not really finishing his sentence. He couldn't say it was for a new set of lingerie, now could he? Not after just having denied the acquisition Linda had just made.

Feeling that Mark wasn't going to admit why he was here Linda intervened. "I'll ask it simpler, are you here for a new set of lingerie, yes or no?" she asked straight to the point in a tone that urged Mark to answer her.

It took a few seconds, but eventually Mark just nodded his beet red head, confirming that he was indeed here to buy a set of lingerie. "Point proven, just like I thought. You are nothing but a huge sissy lingerie addict. Luckily, we have a store full of medicine right here sissy, aren't you excited?" Linda taunted Mark who once again wished for the ground to swallow him whole.

The two of them just kept going until they arrived at the stage with the comfortable lounge chairs. "Alright sissy get up there and strip for me. We can't have you wearing all those yucky baggy clothes that don't even seem to have any model to them. No, you were born for frilly outfits so that's all I'm going to allow you to wear out here in my store." Linda said matter of factly.

Mark just looked at the imposing woman who had just sat down in one of the comfortable chairs. She clearly wasn't afraid Mark would make a run for it, and she was right. It was the other way around. Mark was afraid of what would happen if he disobeyed this gorgeous yet scary woman. The spanking he had received yesterday was still rather fresh on his mind and his confidence in being able to escape before she could stop him was pretty much non-existing.

"Well sissy, are you going to strip, or do I need to bend you over my lap again? You know I have no qualms about doing just that. I even remembered to bring a brush to the shop just in case I got any new naughty sissies." Linda said sharply when Mark hesitated a little too long to strip like she had ordered him to.

The threat and the futility of resisting were enough to get him going. Slowly he started taking of his t-shirt, then his shoes and finally his pants. Linda smirked as she saw his lack of socks and his panties. "Well at least you are improving in your choice of clothes sissy."

Linda observed the nervous embarrassed guy for a little longer delighted with what she saw. "Anyways, while I whole heartedly approve of your choice of underwear. You are here to buy a new set of lingerie, so you can take off your panties as well."

This time it didn't take Mark long to react. Standing there in a pair of panties was just as embarrassing as being naked. Even with the way his pubic bush had been shaped and coloured. So if it would warrant not being punished it was only a small effort for him.

"Good sissy, I still can't believe anyone would actually allow themselves to have their pubic hair shaped and coloured like that. God even Stephanie wouldn't allow for something like that to happen. You must simply be the biggest flaming sissy in the universe." Linda mocked, she knew full well that her word was law and if she demanded it Stephanie would sport the same pubic hair style. Well maybe not, it would be kind of impossible after all given how she had put her stepson through a laser hair removal session to get rid of all his unwanted body and facial hair forever.

"Oh god you're proud off it you sick sissy?" Linda suddenly screamed surprised, pointing at Marks half erect penis making him feel even worse. He couldn't even explain to himself how he possibly could have started to get hard here. Was he really a sick sissy like Linda said? He certainly started to believe so, not even considering the possibility that it could be cause he was standing naked in front of a woman he found gorgeous.

"Well I guess that leaves us no choice but to take care of that first. Stephanie, would you please come here for a moment? You remember the sissy from yesterday? Well, he's back and we are having the same problem as last time again!" Linda called out into the store and instantly the both of them heard a pair of heels clicking towards them.

A few moments later Stephanie arrived. Mark still couldn't believe she actually was a guy. She looked just like a younger, frillier, more exaggeratedly girly version of Linda. If she had introduced Stephanie as he own daughter instead of her stepson Mark would have believed it. The incredibly high heels and the overtly frilly black skirt and white blouse outfit she wore would have led to questions, just not questions about her gender.

"What can I help you with mommy?" Stephanie dutifully asked upon her arrival.

"Well, it looks like the sissy here, you know the one from yesterday just loves lingerie so much that he is back for a new set. I believe you can spot the problem yourself Stephanie, I know it is not a real man's cock, but it is still a cock and you love cocks, don't you?" Linda asked devilishly embarrassing both sissies.

Stephanie threw Mark a nasty look. She had obviously not forgiven the guy for her missed free orgasm yesterday. Even if she rationally knew that it had been just another game from her cruel stepmom and the chance that she would actually be allowed out of the cage was pretty much nonexciting.

Mark threw Stephanie a disgusted look in return. All he saw was a rather flat chested but smoking hot girl. Yet he had seen with his own eyes that she, or rather he was actually a guy. How could anyone ever fall that low? He had asked himself while shaking of the thought that he was well on his way to that himself.

Linda observed the obvious tension between the two sissies with amusement. Neither of them had actually done anything wrong to the other, it was all Linda's doing and yet neither of them dared to throw her a dirty look. It was just perfect, if Linda would leave the two of them alone they might even start fighting. It might actually be a funny to witness, but at the same time she didn't want either of them to have a bruise or anything. Making the two sissies preform under her command while obviously hating each other was just as fun.

"As you can see this sissy here is once again too excited to start trying on lingerie and I was thinking that you could give him another blowjob. I have just decided to be a little more generous though, so I'll allow the sissy to choose. Do you want a blowjob from Stephanie? Or would you prefer me to take care of your little problem?" Linda asked with a big smile.

It took Mark only a second to decide. Sure Stephanie's mouth had felt like heaven yesterday, but there was no way he would choose oral sex with another guy. Certainly not if he could pick a gorgeous woman instead. He could already imagine Linda kneeling in front of him sucking his cock, or maybe even fuck her. God that would really make his day. "I would like you to take care of it Linda." Mark said instantly, a hungry lustful look in his eyes as he eyed this woman who made him think of a real-life Jessica Rabbit. Sure, she was scary, but she probably wouldn't look all that scary anymore down on her knees.

"That's Miss Linda to you sissy, now lay down on your back? The top of your head against my recliner, body stretched out right in front of it and we'll get right to it." Linda said sharply snapping Mark out of his fantasy.

Wait, laying down in front of her chair didn't seem right? Mark thought confused. Maybe she was going to ride him? Then why didn't she even attempt to get up herself. This simply didn't feel right to him as he just stood there sheepishly trying to figure out what was going on.

"Don't make me say it twice sissy or you'll regret it. This was your choice so do it!" Linda shouted at the confused guy in front of her.

Still hesitantly Mark lay down on his back and got in position like Linda had demanded. It felt awkward, especially given how his head was now in between Linda's high heels. He had no idea what the point of this was, but he would find out soon enough he guessed.

He was right, a few seconds later Linda quickly slipped her stocking covered feet out of her high heels and placed one square across his face. The foot felt warm and slightly damp. It ran all the way from his forehead to his chin right over his nose and mouth. Linda's feet had quite a disgusting strong vinegary smell to them. It made Mark want to squirm away, but he couldn't. Linda made sure of that by putting enough pressure on her foot to pin his head firmly to the ground.

Quickly thereafter Mark felt Linda's other foot press down on his semi erect cock, making slow up and downward motions. She massaged the cock that quickly grew erect underneath her feet in a continuous rhythm.

The way things were going it would probably take a while to get Mark to cum. As disgusting as it was the soft nylon sole felt good on his cock, but the rhythm was way to slow to finish him of quickly. Especially with how he was forced to inhale Linda's nasty foot scent during the entirety of it.

Knowing that Mark would have preferred other methods of getting off she used that to taunt him. "I really can't believe you chose to cum like this. I mean you had the chance to use one of the best cock pleasing mouths in town and here you are underneath my feet. You know what happens when you cum don't you?" Linda laughed cruelly never breaking her rhythm.

It made Mark truly regret his decision, but it was too late to do anything about it now. How could he even have been so stupid to really think that Linda would suck him off or let him fuck her. He had to know there would have been a catch, but he was so absorbed in his own fantasies that he didn't really think about it all that much. She was right as well, despite her being a guy Stephanie was one of the prettiest girls he had laid eyes on and she was very skilled indeed. That ball in her tongue only added to the sensation she could bring. In retrospect a blowjob would have been so much better. He would probably have cum already.

"Stephanie, come here for a moment." Linda suddenly said while she continued to rub. Stephanie leaned closer to the recliner and Mark could hear something being whispered but he did not know what. He couldn't really see what was going on either since he only had the edge of his view to rely on with Linda's foot dominating the middle.

The next thing Mark heard was a giggle from Stephanie followed by. "Yeth mommy, it will be my pleathure." Stephanie sounded enthusiastic which made Mark worry about what the two of them had been discussing. Judging from the looks Stephanie had given him he guessed that whatever she was happy about couldn't be good for him. Sadly he couldn't do a thing but wait for it to happen while Linda was getting him closer and closer to orgasm.

Mark heard Stephanie's heels click away from him, but he did not know with what goal. Despite his worries and the intense nasty smell of Linda's feet Marks balls tensed up a few minutes later and he started cumming hard. Depositing spurt after spurt of sticky white cum between Linda's foot and his own belly.

Linda instantly started laughing. "That's pathetic sissy, getting all worked up and cumming for a pair of sweaty feet. You know I would have just thought you would go soft on your own but here we are pervert. Well you know what follows after spurting your sissy cream don't you? I think it's time for the clean-up." Linda taunted, she knew it was normal to cum from the stimulation, but her guess was that Mark was sexually inexperienced enough not to know. Making him cum was just so much more fun when she could make him feel embarrassed about it.

It was time to clean his mess now though. So Linda moved the foot on his head slightly back away from his chin and finally away from his lips. She curled her toes, so they hooked under his nose, blocking his nostrils and tilting his head back slightly. This forced Mark to breathe through his mouth. "Alright sissy stick out your tongue like a good little bitch." Linda said sharply.

This time Mark didn't hesitate but instantly complied. He was trapped anyway so what was the point? Reluctantly he stuck out his tongue as far as he could. From that point on he didn't have to wait long at all. Linda instantly lifted her foot of his cock and brought it up to his face only to use his stuck-out tongue to wipe her soles. After a few wipes she stopped. "Swallow and stick out your tongue again."

Obediently mark did as he was told. The feeling and taste during the wiping had been nasty, but now that he pulled his tongue back in his mouth the taste intensified tenfold. It was the salty tasted of sperm he had gotten to know yesterday, but it was mixed with something also salty yet acrid tasting. He realised it was Linda's foot sweat which made him shudder.

He made a disgusted face much to Linda's delight but stuck out his tongue again anyways. "Good sissy." Linda laughed before wiping her foot on his tongue again. She repeated this process five times until she was certain all the cum was gone from her sole. There was still a hefty amount laying on his stomach however.

Linda quickly solved this by scooping some up with her big nylon covered toe before pressing it between Mark's lips. "Suck sissy, suck your cummies out of my stockings." She said sternly before letting out a satisfied moan when Mark complied she never thought it would actually feel that good. Certainly something she would have to do more often, she thought with a smile.

12


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