Wrecking the Homewrecker

Class with Master Frank

"Alright sissy let's get you out of those cuffs of yours so you can give me a proper greeting shall we? I've been told that you've been educated in proper sissy etiquette so I expect nothing but perfect behaviour from you, otherwise the only action that ass of yours will be seeing is that of plenty of sound spankings rather than the privilege of getting to enjoy my cock." Frank grinned as he turned off the vibrating plug and unlocked the cuffs holding Jason down on the bed.

Jason for his part was absolutely mortified thinking about taking a real genuine cock up his ass. Taking Sally's fake one had been more than bad enough already, but doing all he had done to her dildo to a real cock was tent times as horrifying. Still he needed that itch scratched so badly and he was desperate to avoid any more spankings as well. So for as bad as it was that cock really did sound like some kind of twisted privilege to him. Plus if he failed to please Master Frank he was sure to be made to pay for it double when Sally or Bernice heard of it. He really couldn't screw up and much to his shame that cock was one of the reasons why.

Not knowing exactly what Frank had been told about his sissy etiquette, Jason's only real option was to act as perfect as he knew how to, trying to execute all of Sally's instructions over his time her flawlessly. With that in mind he took the smelly sock off of his nose, took the saliva drenched one out of his mouth and nearly put them aside only to slide his glasses on and slide into his mules in front of Frank, naked aside from his cage and the by now rather full small pink condom full of leakage dangling off the end. Picking up an imaginary skirt he dipped into a deep curtesy before the man happy not to have to look him in the eyes, although staring at that tent in his pants didn't feel much better to him at all. With a loud by now habitual snort he corrected his glasses which had slid down during the bow only to giggle and speak in his ever more natural sounding high pitched lisping voice. "Hehehe, welcome Master Frank. Thank you so much for your visit and wanting to teach me a valuable. I hope to be of service of you and that delicious cock of yours." Jason spoke, cringing at his own words yet motivated to lay it on thick just not to screw up.

"Hmmm do you like cock Jasmine? I can't help but notice how you only seem to have eye for my cock, or are you maybe just a little shy and find it easier to talk to a cock? Would you perhaps like to take it out and play with it? Hold it in your hands, maybe your mouth?" Frank asked with a big smile loving to see the freckled face before him turn beet red while Jason instinctively corrected his glasses with a loud snort. It was pretty comical to Frank, but at the same time it was most definitely cute and he just loved toying with the sissy, it made the tent Jason was looking at throb which only further fuelled his blush.

"Yes Master Frank I do. I love cock and I love playing with it in every way that I'm allowed to play with it and maybe I'm a little shy as well Master Frank." Jason said while squirming on his high heeled mules, lending further credence to the shy statement. The mere thought of actually handling another man's real cock made his stomach turn though, but at the same time his ass was clenching around the base of his plug in anticipation of that deep fuck hitting that special spot inside his ass enough to tip him over that horrible aroused edge.

"Wonderful because my cock seems to love you too. It's a pity that you have had to go without a real cock to play with for so long that this is about to be the first time in your life that you'll get to play with a real cock. You can suck and savour it in a few moments Jasmine. My balls are full of pent up cum for you to enjoy, aren't you a lucky sissy? It'll be good to get all of that out so I can last longer when fucking that ass of yours. Consider it your dessert to come as I still have to give you your lunch, but before we get to that, why don't you make yourself all pretty for my cock? You can start by changing that small sissy leakage bag out for a fresh one and hand over the full one. Let's save that too for after your meal so you can taste how your pathetic leakage measures up to a real load. Are you excited to get to play with your very first real cock instead of that now luckily locked up clitty?" Frank asked grinningly, loving how Jason's squirming only seemed to get worse.

"I'm very excited I'll get to play with my very first real cock Master Frank, thank you so much for offering me such a great opportunity, I almost can't wait. I'm such a lucky sissy." Jason gushed with a deeply embarrassed high pitched lisp as Frank had a good laugh at his expense. Less than a week ago he had had his cock sucked by a hot girl yet here he was feeling as pathetic as he sounded while his ass ached for that cock, his arousal so maddening high that the shame was dampened a little yet with how embarrassing his situation was it reigned more than supreme. His arousal paired with the sheer helplessness of his situation and the fear of the potentially painful consequences of disobedience kept him acting as pathetic as expected of him. Still he couldn't believe he was about to really suck the cock of a guy who looked older than his mother even. If anything it was even worse than the prospect of getting fucked, he thought as he obediently handed the fully leaked condom to Frank only to pull another over his caged cock. Getting fucked for as bad as it was would at least give him that much needed relief. It also didn't make as big a difference whether it was a cock or a very realistic dildo or a real cock he was dealing with back there as it did for sucking it, the taste, smell and especially the load were bound to be so much worse.

"Would you look at that, I don't think I've ever seen someone leak this much over a smelly pair of socks. It really makes one wonder just how much you are going to love my cock once I give it to you, but first, off to the closet you go, put on some knee high socks and glossy nude nylons, oh and put on your face as well. I want you looking perfect for my cock, so translate that desire of yours to suck my cock into effort in your look." Master Frank ordered, chuckling when Jason quickly agreed with yet another curtesy before mincing off to his closet to get dressed in the variety of his school girl uniform with the white knee high socks with their ruffled tops and a pair of glossy nude thigh high stockings to pimp the look of his smooth legs.

By now Jason pretty much had the hang of getting dressed and doing his makeup. It still took a considerable effort and quite some time, but he managed to get it done on his own. Less than a week ago getting ready just meant a quick shower and throwing on the closest pair of pants and t-shirt. Now just putting on his outfit with all the difficult to handle and delicate materials took more time than his entire morning ritual used to do and that still left him makeup less with messy hair. Doing all that took even longer than putting on his clothes and that was with the largest part of his morning ritual, getting bathed inside and out, already behind him. The fact that he was doing all of this to suck a cock made it so much more painful. He couldn't help but shudder as he carefully applied layer after layer of brightly coloured lipstick to his plump lips only to finishing it off with an inviting looking gloss as he knew where those lips would soon wrap around. He badly wanted to do a bad job because making himself all pretty for cock was just too painful, but he didn't dare do so. Frank looked way stronger than Sally still and she could already man handle him after all.

Getting up from behind the vanity table Jason was once again looking like the perfect sissy school girl and he knew full well it meant a step closer to sucking an actual cock. Luckily there was still lunch as Frank held out the bottle of sissy formula with a huge life like dildo stuck to the cap. It had been days since he had had any real solid food, or consumed anything he didn't have to deep throat out of a dildo. "Alright Jasmine, why don't you show me exactly how you would like to suck my cock? You can get down on your knees for extra immersion." Frank grinned as Jason shamefully grabbed the bottle and did exactly that. He wrapped his plump lips around the head of the dildo and circled it with his tongue to by now skilfully prep the mechanism before deep throating the entire impressive length of the dildo and sucking his pink meal out. The meal which was rapidly making him weaker, deteriorating his muscle so he could look as dainty as he acted. All this time he could only look at Master Frank's throbbing tent in the front of his pants and shudder a little thinking how he would have to suck that next.

With the bottle in hand, able to control it himself for the first time Jason managed to drink it down a lot faster with a lot less effort as he was able to kind of push it in while he went down on it as well. Right now moving faster was the last thing he wanted though, but he did settle into a steady rhythm nevertheless. Usually he was happy to see the fluid drain from the bottle so this horrid part of his day could end, but right now he wanted the bottle to last forever. All too soon however he managed to drink out the last few drops and almost reluctantly pulled that way too large dildo out of his mouth knowing what it would be replaced with.

"Mmm, that looks great, I can already tell that you're a great natural cock sucker Jasmine. I mean not that I doubted that for even a moment, with your self proclaimed love off cock, those delicious looking lips and all that effort you put into looking your very best for my cock, I already knew you were going to be great. In any case, why don't you open up and give that pathetic dribble of yours a taste so you can freshly compare it to a real load. Also those lips can use a touch up, I want them looking fresh and perfect before allowing them to wrap around my cock. When they're perfect again, you may drop back down on your knees and beg me to suck my cock. Make sure to really voice how much you want it, cause I may be horny, but if I think you might not appreciate the privilege enough I have no qualms rubbing one out over your face instead. I will however drop at least two loads in that mouth of yours before I even consider fucking that ass and if you waste one, well then that's on you." Frank grinned as he held out the small pink condom filled with leaked precum from Jason's cage.

Mortified, yet obedient Jason opened his mouth an allowed Frank to squeeze the rather watery contents out of the small latex thing between the plumps slightly ruined lips. Less than a week ago he would never have thought of tasting his own cum, hell he wouldn't even kiss a girl who had freshly sucked him up, yet here he was accepting the full load of precum on his knees in front of a guy while feeling glad that it was only his cum which he had tasted way too often for his liking by now. Even worse, he thanked Frank for it with another curtesy after getting back up just like he had been taught to do when he got something from someone no matter how embarrassing that something was. With that Jason minced back over to his vanity mirror to quickly touch up his lips realising full well that he was making them perfect for a cock. On one hand he was glad to delay the inevitable a little more, but he was anything but glad about what Frank had just said. In his arousal clouded mind he was even more prone to confusion and with his butt clenching in anticipation of getting fucked paired with being unable to deny that he had in fact proclaimed his love for cock, making himself pretty for one, he couldn't help but start to doubt if he did actually love cock to some degree.

Mincing back over to the middle aged man who was his Master this afternoon Jason dropped back down and started his plea. On one hand he had wanted to plea not to have to do this mortifying thing, but all he would do was make things harder and trickier for himself as he couldn't deal with being this over aroused. He needed to make this work despite his doubts there simply was no other way, so he laid it on thick, hoping it would be enough. "Master Frank, may I please please please suck your cock? My lips have been aching to wrap around it since I first saw your bulge and I have been fantasising about how a real cock tastes for ages. Please can you make my fantasy a reality and allow me the privilege of sucking my very first real cock? I would be forever grateful." He lisped pathetically in his high pitched voice.

"Well if you beg so nicely then who am I to say no? You sound so pathetic that I would almost feel bad denying you my cock. So go ahead Jasmine, get it out of my pants and start sucking you have my permission to enjoy the privilege. Make sure to really savour it, taste what a real man tastes like compared to nothing but a pathetic sissy." Frank spoke with a grin as he just remained standing, obviously not about to do anything to facilitate Jason's job at all. Like with his outfit, makeup and the begging he wanted to make him work as much as possible for the cock he was about to suck.

It felt awful to Jason as he had never stooped this low before in his life yet driven by sheer over arousal and fear of potential consequences he shamefully obeyed. Frank's words about how pathetic he was really stung, but given that he was doing all of this just so he could feel this cock go up his ass to get him off, he couldn't help but agree that it really was pathetic. With all the work he had put into earning this he also couldn't help but feel like it was an actual privilege. Right now all he wanted was to get this over with. After all he still had his work cut out for him as this would only be the first of two oral orgasms he had to provide his Master with before getting fucked Jason thought mortified as he nervously started unbuttoning the man's pants, cringing as he could feel the cock throb underneath his daintily manicured hands. He had unbuckled plenty of pants, but doing it in front of him right at eye height with what was awaiting him after the fact was devastating.

Once he got everything opened up Jason gently lowered the pants, the throbbing tent being so much clearer in the relatively thin material of the boxer shorts which reluctantly got pulled down again making the proud rock hard seven inch cock jump out and stand at attention right in front of him. He had seen plenty of cocks on the various pictures in this awful room, had to deal with plenty of realistic dildo's, but nothing could have prepared him for this real genuine cock throbbing right in front of his face, a very strong musky scent wafting off of it, something no dildo had and it was so much different from the foot scents he was accustomed to. Jason was only barely able to hold back a gag knowing what he was smelling making him all the more reluctant to put his lips around it, especially when he got a very deep whiff when snorting to correct his glasses again. Frank couldn't help bus smirk seeing it all from above. He had been on a morning run just for this occasion to present a musky cock to the sissy and it definitely had the desired effect.

"You know Jasmine, with how much you seem to love cock, I think it would be a nice gesture to give it a little kiss as a greeting when spotting a hard member you're about to suck. Nothing says love like a little kiss. Then once you've fully savoured the load and swallowed you can give it a thank you kiss, or a goodbye kiss depending on how you look at it. I think that would be a nice gesture to show how much cock means to it so get into that habit will you?" Frank spoke just when Jason seemed to have worked up the courage to go for it and just get this over with. It stopped him right in his tracks, he hated the idea, but then again failure was not an option. Maybe if he could have had his lips around that cock a little sooner and given Frank a blowjob which would have sent him straight to heaven, consuming him with too much pleasure to come up with these horrid ideas, then maybe he could have prevented these words from being spoken. Words which were bound to turn into rule as he didn't question Sally would be watching this video feed and think it was a great idea.

He was too late though and so instead he yielded yet again, puckering his lips rather than opening them as he planted a quick peck straight on the head of the cock, the pearl of precum which had leaked out now coating his pillowy glossy lips. Just as they made contact Jason couldn't help but let out a loud moan as if he just loved it, a moan which turned his cheeks bright red, caused by a strong surge of vibrations from his plug to his overstimulated prostate. It felt awful, here he was on his knees, not just sucking cock, but literally worshipping it, showering it with love and affection and moaning alongside it. He was surprised he could even feel more pathetic after everything, yet here he was, definitely feeling like he had sunk to a new low.

With the quick peck over though Jason hurried to get his lips wrapped around the throbbing hard member before Frank could come up with any other additions to make this whole experience that much more shameful. He couldn't believe he was actually doing this, but soon his lips slid over the sensitive pulsing and leaking head, the warmth, the velvety softness and the taste of another man's precum and musk instantly strong on his senses. For as realistic as all the dildo's he had to deal with were, they still weren't quite the same as a real cock and it made the whole thing so much more embarrassing, especially when the plug in his ass started vibrating full force again, moving him right to an edge he hadn't been left to stray too far from all morning along with the accompanying moans. Moans which forced him to breath deeply through his nose now that his mouth was stuffed. Instead of feet all he smelled now was Frank's musky cock though.

Not only was he sucking cock, he was actually loving it, or at least that's how it would seem to any outsider, moaning like a bitch in heat just because he had a cock in his mouth. Frank just couldn't help himself but make a remark about it driving home Jason's shame that much deeper. "Wow Jasmine you really weren't kidding when you told me just how much you love cock. I mean getting so excited just from giving it a kiss, and now look at you, you nearly couldn't wait to get it in your mouth and I can see why. I have never known anyone to enjoy cock this much, you even look like you might have a spontaneous orgasm just by getting that cute dorky face of yours fucked." Frank laughed as Jason only whimpered through his moans, having a hard time even thinking now that he was kept right on edge again. It could have made this task nearly impossible, but at this point he had so much experience from sucking his meals out of those dildo's that he was able to suck on autopilot alone.

While there wasn't a ring subtly hiding underneath the head of Frank's cock, Jason still circled his tongue around it, the wet surface moving over the head it self while the piercing and tip massaged the under rim of the head where it ran over in the shaft. He wasn't really thinking much about how he was sucking cock. With his arousal this high he was in no position to think really, but the familiar shape in his mouth required no thinking, he just circled it five times as had become habit. Having shown the head plenty of love, he expertly sucked the whole length of Frank's cock down with ease, having had bottles with way larger cock's attached to them than Frank's large, but very manageable seven inch cock.

Sliding down the shaft the mixture of precum and musk was replaced by the overwhelming taste of musk, the smell becoming overpowering when instead of pressing that button at the base of the cap like he was used to, his nose pressed into Frank's thick dark but greying pubic bush while his chin pressed against the man's balls. Not really thinking much, another one of Jason's habits kicked in, having felt his glasses slide past a certain point on his nose, he quickly corrected them with a snort, sucking in air thickly filtered by Frank's pubic patch. It was bad enough to make him whimper through his moans as he quickly sucked his way back to the tip again for some relative fresh air, applying plenty of suction along the way. Like with the head he took Frank's cock down his throat five times, aside from a drop of precum leaking out, no fluid coming along with it as it usually did.