Neighbourhood Terror to Sissy Pt. 13

"Good, for the rest of the spanking I would normally just opt for a set number of spanks, but since you are new and might not be hitting hard enough for the desired effect, I propose that we just keep going until their bottoms have that nice dark red glow. You know, that same colour their cheeks turn to so often." Linda proposed.

Mark could vouch that his girlfriend certainly did hit more than hard enough but saying so would just get him even more spanks so instead he kept kissing with Stephanie. "When you spank them, it is good to find a set rhythm and spank each cheek in turn. Unless you want them to be unable to brace themselves. Then it is best to do it irregular and choose butt cheeks at random." Linda explained as she gave Stephanie's left cheek a hard whack followed by another one two seconds later on the right one, going back and forth like that.

Lisa soon adopted the same rhythm as Linda used and started spanking Mark's bottom in union with Linda. Both sissies grunted and groaned into each other's mouths, but they did make sure to keep their lips pressed together even as they had started sobbing, knowing things would grow worse otherwise.

Each spank felt like it hit harder than the last as their bottoms had started to become quite sore. This went on for what seemed to them like forever. The pain in their bottoms grew to intense levels and they both thought the punishment should have been long over.

If both women had followed the goal for their spankings as they had said at first. The spanking would have indeed been over, but even after both bottoms had turned a glowing red they had continued just for fun. Lisa especially was having way too much of a blast delivering her first spanking.

Eventually the spankings did stop however, both sissies were still dutifully kissing. "Once the two of you are done kissing you might get up. I think that spanking should suffice, unless you sissies want more of course." Linda said with a smirk.

They didn't need to be told twice as both of them instantly broke their kiss and got up on their feet, glad it was finally over. "Thank you for the thpanking mommy." Stephanie said in an instant, drying her tears. Mark had had no intention to thank Lisa, he the thought hadn't even occurred to him until Stephanie did it.

With his hurting bottom and the expecting looks from both Linda and Lisa he didn't dare do anything but utter his thanks either. "Thank you for the spanking Miss Lisa." He sobbed softly, still finding it very awkward to call his girlfriend Miss.

"You're very welcome Marcy, I am glad to see you liked it just as much as I did, and don't worry, that was a first of many spankings to come." Lisa said with a wink to her shocked, scared boyfriend. She knew he hadn't actually been grateful, but that made it even better.

The spanking had been yet another reason for Stephanie to hate Mark. Normally her spankings were a lot less painful and intense than the one she had just received to help Lisa with her training. Rationally he should know that this wasn't Marks fault yet Mark was the one he blamed. He was the only one who could be blamed to not get in trouble. He was the only one Stephanie could get some form of revenge on like with the tiny chastity cage, even though that had blown up right in her face.

"I have noticed that you mentioned your disappointment in the inability to have sex with your boyfriend a couple of times." Linda suddenly said to which Lisa instantly nodded her agreement, it had been what had led her here in the end.

"Well first of all I would like to tell you that I saved you from an even bigger disappointment. You see, sissies are literally the worst when it comes to sexy. Their cocks are less than average to tiny and they don't even know how to use them either. You see, a sissy is best kept under lock and key at all times. For their own good, and the good of everyone around them. It makes them more obedient and it helps them get rid of the silly idea that they are men." Linda stated.

Mark wanted to object that his cock was bigger than average, and that he would prove that he could fuck. After all he had never had the change to prove it before since he was still a virgin, but he was sure that he could do it. He doubted that Linda would unlock him though and clearly his girlfriend believed her more than she did him. Besides his size was very hard to tell locked up in the way to tiny cage. The one that had started to feel less and less tight. In the end he decided that there was just no point in arguing. Instead he shamefully hung his head.

"If you do look past the classical image you have of sex however, sex with a sissy is still a possibility. Sissies derive pleasure through their butts, it is their main way to get off. So if you focus on their butt holes you can have sex with a sissy." Linda informed.

It was instantly met with a practiced shocked look from Lisa towards Mark as she cried out. "No way!" Of course she knew about this, she had seen Mark play with himself over John's website before. Mark didn't know that though and so this was a perfect opportunity to embarrass him even more.

"Oh yes, if you don't believe me why don't you ask for yourself. I am sure Marcy would love to inform you if it could help your sex life as a couple. Isn't that right Marcy?" Linda asked with a big smirk on her face as Mark nervously nodded, his bottom still burning red as a reminder that he should cooperate.

"I don't believe you, but sure, I'll play along. Have you had an orgasm even though your cock was locked up?" Lisa asked her boyfriend with a curious smirk.

Linda tuned in. "Marcy, I want you to answer your girlfriends' questions truthfully, it is of utmost importance to your relationship, and I pride myself on being a human lie detector. Well more like a sissy lie detector, but you get the gist. If I catch you in a lie that spanking you just received will feel like a walk in the park. Oh, and use your manners when you answer."

Nervously Mark looked over to Linda, then back to Lisa. Even though he was standing here in his bare bottom, with his cage on full display, that felt like the least embarrassing thing of this situation. "Yes Miss Lisa, I have had many orgasms since my cock was locked up." He nervously stammered.

"Oh really? And how the hell did you accomplish that? I can't imagine you managed to get hard, let alone deliver a lot of pleasure to your cock wearing that cage." Lisa continued her line of questioning.

"I fingered my butt hole till I came Miss Lisa." Mark stammered softly, his cheeks turning the same shade of red as his butt.

"Hmmm, I'm still not convinced. I'd have to see first before I believed any of that. Actually why don't you get up on that stage and show me exactly how you managed to cum so many time even though you are locked up?" Lisa asked sceptical.

With a look of utter disbelief Mark looked between his girlfriend and Linda who were both eyeing him expectantly. Even Stephanie was smirking broadly. In the end Linda broke the silence. "What are you waiting for sissy? Didn't you hear your girlfriend? Get up on that stage and put on a show for us, or else..." Came her threatening words.

On shaky legs Mark eventually found his way to the stage where he climbed up on the edge? Resting on his hands and knees as he moved one hand to his butt looking at his small audience a last time in the hope that one would say that they were just joking.

Those words never came and so in utter embarrassment Mark moved one of his hands between his red butt cheeks and inserted a finger into his rectum. An instant moan escaped his lips, followed by a gasp coming from Lisa. "Oh my god, he is really doing it. I can't believe it. Will he actually cum like that? I mean it looks almost exactly like a girl masturbating. Well a girl who can't seem to find the right hole." She laughed.

"Just wait and see, I am absolutely positive he will cum like the sissy butt slut he is." Linda said keeping her eyes glued on stage. This was the exact reason she had opened this store. God dealing with sissies was just so satisfying.

While everyone was looking at him with wrapped enthusiasm Mark wished the stage would open up and swallow him whole. His visit to CC's today had turned out to be the most humiliating experience of his life so far. He simply couldn't believe he was actually fingering himself in front of this wicked store owner, her sissy stepson and his own girlfriend. To make matters worse he was already fighting back the urge to cum.

It was a battle he was quickly losing. He hadn't realised up until now how much of a butt slut he had actually become. He had only been going at it for a couple of minutes so far and yet he was right on the edge already. His moans were becoming more and more frequent. Then all of a sudden his whole body tensed up and he came right there on stage. A few ropes of sticky white good spurted right underneath him out of the tip of his chastity cage. When they stopped Mark slowly removed his finger from his butt and just stayed in place, catching his breath.

Everything went silent for about a minute until Lisa spoke up. "Oh my fucking god, unbelievable. He really is way more of a sissy faggot than I ever imagined possible. God, I mean he can really cum just from fingering his ass. I didn't believe it at first, but now. Wow!"

"See, I told you. Now why don't you come join me so we can have a closer look. The trick to having sex with a sissy is just about finding the right spot, nothing more than that. Once you know where it is you can choose to stimulate or avoid it depending on whether you want your sissy to cum or not. To get a feeling for where it is I suggest trying with a finger, but once you get the hang of it literally anything will do, your finger, a toe, a whole fist, a strap on dildo,..." Linda exclaimed calmly as she walked over to the stage followed by an eager to learn Lisa.

"Stay right as you are sissy, if you dare to move you will be sorry." Linda threatened as she approached Mark who was still coming back to his senses, resting on all fours. Without any regards to him Linda then proceeded to spread his sore red butt cheeks and shoved one of her fingers right up his butt hole.

Mark instantly answered with a groan followed by a moan as Linda pressed down on his prostate. "See how easy it is to get a sissy going? One magic touch inside their butt is all it takes to get them moaning, or as I like to say it's very easy to get a sissy wrapped around your finger." Linda joked with a cheeky grin.

It was instantly received by loud laughter coming from Lisa. "Oh my god, you're right. He has only just cum, and he is already moaning like a bitch again. What further proof do you need that he isn't a real man? Real men are never ready right after an orgasm."

"Well, I guess we at least found something sissies are better at." Linda said as she pulled her finger out of Marks butt. She grimaced when she noticed it was a little dirty. "Stephanie, go fetch some sanitising towels and a pair of latex gloves." She ordered.

"Yeth mommy, right away." Stephanie answered before scurrying off only to return a moment later with the demanded items.

Linda quickly cleaned her finger and handed the gloves to Lisa. "I see the sissy isn't really clean yet. I recommend setting him on a strict douching regime. Stephanie here is always clean and smelling of cherry down there. I always loved the irony of being able to pop her cherry every time."

"That's noted!" Lisa said firmly before eagerly pulling on a glove on her right hand. Then without warning or hesitation, she plunged her finger knuckle deep into her boyfriend's butt hole and started wiggling it around getting out mainly grunts with an occasional moan.

"You're not afraid to get in there, that's good. Now I want you to pull your finger nearly out and make sure the tip of your finger is aimed down. Then I want you to gently slide it down alongside the wall, deeper and deeper until you can feel a slight bulge. That's the prostate, the magical spot to make a sissy go crazy. Once you mastered finding it, it really is almost an off and on switch." Linda instructed.

It took Lisa two tries but helped with the sounds of Mark's sudden moans she managed to locate the prostate. "Got it!" she shouted out with excitement as she instantly started toying around with it, prodding and poking away at it. She relished in the moans and cries of pleasure the movements of her fingers elected from Mark. With burning curiosity, she continued to experiment with various ways of stimulation.

All Lisa's experimentation was quickly getting to Mark and to his intense shame he quickly found himself cumming yet again. Much to Lisa's joy who instantly squealed in delight. "Aaaah I did it, I made him cum, and that right after an orgasm while he is locked up. An achievement if I do say so myself."

With that Lisa decided to put a stop to her experimentation and removed her finger form her boyfriends butt. The puddle of cum underneath Mark had nearly doubled in size and he was breathing even heavier than before. The two orgasms in rapid succession had really taken their toll.

"You did very well Lisa. Of course this treatment should be reserved as a reward, or simply because you feel like it. Another big part of a sissy's sexuality revolves around oral skills, pleasing their superiors if you will. I will leave that part up to you to discover though. After all cunninglingus is a matter of preference. I can advise getting him a tongue piercing Like Stephanie for added stimulation though. It feels like heaven and it gives them a cute lisp. At least that is how Stephanie got her lisp." Linda informed much to Marks horror who had picked up on the conversation. Lisa wouldn't do that to him right?

Linda led Lisa back to the comfortable recliners and sat down. "Now Before we continue why don't you start licking up your mess Marcy? I know you love the taste of cummies even if it is just sissy cream." Linda said as both of them turned their attention to the stage to watch the show.

With a loud groan Mark slowly turned around and started lapping up his own cum. He really detested the taste, but more so his mind was filled with dread of what was yet to come. He had a bad feeling that their visit wasn't over yet.