Wrecking the Homewrecker Pt.51

Anatomy with Master Frank

Up in his room after what felt like forever Jason had finally finished with that utterly degrading essay on why. It had taken him what felt like forever to get that many pages filled, with nothing but praise for Frank's cock along with insults and ridicule for his own caged member. His full concentration going to keep finding new praises for Frank's cock had been devastating to his already broken identity. Especially with the very depraved things he came up with to write down. Praising everything from the scent, and taste to the feel, even that feel and scent of his musky pubic bush tickling his nose. He praised how Frank's cock smelled like a gorgeous delicious, man's cock, while his smelled just like a cute little flower.

Praise only went that far, so he had had to resort to fantasies, just the normal ones, of how much he would love to suck such a manly delicious cock again. Then a little harder to how he would love to have his boy pussy fucked by it. A praise all the more devastating because that was exactly what he was yearning for through all that edging he had been subjected to. Actually wanting that and doing all of this for it, made him feel like a bigger sissy still. Soon those fantasies were not enough to fill the pages though and he had to go to increasing lengths to keep on writing, like how he wished he had a pussy of his own instead of that worthless clit so he could feel Frank's magnificent cock in another hole, and after that even going to the complete non sensical dream scenarios. Things like how he dreamed that he could be a condom so his whole body could be tightly wrapped around that amazing cock, soaking in all it's greatness among other such twisted dreams.

Throughout the essay his writing was going nearly automatically, he was getting quite in the habit of writing with plenty of hearts and curls while sucking on the back of his pen ever so often, and practicing it only made it that much more ingrained in his way of doing things. If he got out of here, he would have to make a very conscious effort not to write with all those hearts and curls anymore. Not sucking on the pen would be even harder to unlearn as he was barely even aware that he was doing it anymore, much like the correcting of his glasses every so often. By the point he put his last heart shaped dot behind his line the whole document looked neat, tidy and ultra feminine. Only the last three pages or so had some messy spots where he had had to really rake his brain too long to come up with something to write. He knew he would regret those, but there were no do overs as he finally looked up at Frank's cock and exclaimed. "I'm done Master Frank."

"Good girl Jasmine, well then what are you waiting for? Lets get you on your knees before me and you can read your love letter to my cock. Lets make it a little animated though, I don't want to hear some plain monotone reading voice. I want to hear the same enthusiasm and love in your voice as put into your writing." Frank grinned as he got up from the desk, and stood at attention, Jason hurrying to fall down on her knees before him. There was no getting out of this, so he might as well just get it over with, besides the quicker he got there, the quicker he could find some relief granted by that cock which he embarrassingly enough was looking forward to even more with how great he had made it sound and how horny he was.

For as wounding to his self image as writing this essay had been, reading it out loud was so much worse. Somehow it made the words feel that much real, especially with the effort Jason forced himself to put into bringing it theatrically, staring at the cock mere inches from his face as he exclaimed loudly with his terrible lisp in his practiced high pitched sing song voice. Saying all those horrible things out loud somehow made them seem so much real than just thinking them and writing them down. Especially when Frank worked in the occasional mocking remark turning Jasmin's face even redder than it already was underneath all that makeup, making him stumble over his words for a little bit. It got especially bad when he had to read out those outrageous fantasies he had come up with just to fill all his pages while Frank laughed his ass off calling him a real twisted sissy pervert. Jason could hardly blame Frank for that as that was exactly how he felt. Saying it out loud, he couldn't believe he had actually come up with such things.

Thing were made so much worse still by the fact that throughout all of this Jason actually found himself rooting for the cock right in front of his face to rise. He didn't want to suck it again, but he needed to succeed at this task or there was no telling how long he would have to deal with this horrid arousal. His own rooting, paired with the enthusiastic praise he was singing about this cock was doing a real number on his mind. He rationally knew that he was just doing a task, that he was not an actual sissy, that he was into girls, not guys, especially not guys old enough to be his dad, but it was getting increasingly hard to keep believing that was fully true. After all he did feel his mouth water at the thought of sucking that cock again, simply because of how he was telling about how absolutely delicious it tasted and smelled. He didn't want this reaction to happen, but it did outside his control, and it got rubbed in all the more when relief which could very well be mistaken for joy washed over him as Frank's slowly rising cock turned into a full fledged erection.

"As I see you've noticed by that drooling hungry expression on your face, you've succeeded in your assignment, congratulations Jasmine. Although I guess with how much you love and adore cock this wasn't exactly a hard task for you now was it sissy? It certainly sounded to me like you finally got to admit just how much you love cock and who am I to deny you what you love. Your treat for another job well done is a nice juicy blowjob now hand me those sheets so I can count how many spanks you'll get and get started Jasmine." Frank casually spoke with a huge grin as Jason could only whimper softly. Frank's comments hit so much harder now that he was actually struggling with his own thoughts about the subject, having had to think and speak about it with so much enthusiasm that he hardly knew what his real thought were and what he had written for the sake of this task, although he guessed no matter how he looked at it, he had done this all for cock which made it incredibly painful.

Jason didn't hesitate to do as he was told, not wanting to screw up all this hard work by quitting now. Obediently he handed up his sheets of paper which Frank instantly snatched from his hands, then without delay he wrapped his head around the cock he had just sung praise about and started sucking yet again. In the past getting a blowjob as a treat would have meant getting his cock sucked by a hot girl, yet here he was, the cock in his mouth and somehow that was still called a treat. It wasn't even close to as good as he had described it, hell it wasn't even close to being good Jason thought, the smell taste and feel of another man's cock in his mouth disgusting him. He didn't know how to feel about that either. It was a relief that he wasn't actually loving cock as much as he had been describing, but then again this would have been a lot less disgusting if it actually tasted and smelled as good as he had described. Not that it showed in his performance at all. Despite his disgust Jason gave the cock in front of him his all, sucking it the way he had gotten in the habit of doing from his meals, and it was working wonders as it didn't take him long to get Frank moaning. Sadly the vibrations of his plug had also started up again, making him moan even faster.

With his first orgasm out of the way Frank ended up lasting way longer than he had the first time. Then again the first time he had gotten off faster than usual with how pent up his arousal had been. Done with counting the slight sloppy spots in the long essay Frank had put the sheets down and focused his attention fully on the sissy sucking his cock. It was an outrageously hot sight and he could hardly wait to get the sissy on its back and his cock stuffed deep up its bottom. Right now it was time for another lesson though. "Mmmm you're doing great Jasmine, I only have one remark and that is that your actions are a little repetitive. Try to put some variety in them, run your tongue back and forth over that slit at the very tip rather than just around, gently tease my balls with your nails, take some more time, do it slowly and sensual, then speed up to your regular pace again,..." Frank commented as he instructed the sissy on its knees how to become an even better cock sucker.

Down on his knees Jason was mortified, as if sucking a cock wasn't bad enough yet, he now had to be passionate about it as well. It already sounded completely wrong with his inability to stop moaning, and now this? Nevertheless, overly aroused as he was Jason kept giving the cock before him his all, trying to follow all of Frank's instructions to the letter. It felt disgusting to run his fingers over that hairy velvety sack, and licking that slit covered his tongue in precum. Going about it slowly also made it seem like he was loving it as much as it sounded like, but not doing it would be even worse. It would only mean giving Frank more blowjobs while his ass would be denied the pleasure of that cock fucking him and being rapidly driven to edge after edge by his plug once more made him need it more than ever. He felt disgusted and pathetic, but to any outsider it would just seem like he was loving cock as much as he had described and Frank's cock was definitely throbbing harder over the passionate sight he got when looking down. At least his sheer over arousal did dull a lot of the shame, not that that made things easy. It just made it easier to comply.

For the next twenty minutes Frank kept giving suggestions on things to try so he could become a better cock sucker and like with his earlier suggestions Jason did his best to comply. The basics he had learned from his bottle gave him a solid foundation to work off of. It had made his tongue very nimble and taught him to deepthroat with ease. It was however a little dull, repetitive and rushed, but more than capable of getting any man off. With Frank's instruction he went from just sucking cock to actually making love to one. It was no longer about just giving pleasure, but also about giving a show, turning them on further rather than just getting them off. Sucking cock like this would make every cock around him hard for him, in the mood for Jason to take care of them as well, or if the person he was with didn't allow that, to make other's exceedingly jealous. It was devastating for Jason's mental state as it made it less of a chore that he could just get over with, and more of an active involvement, requiring him to think on how to best please a man. Being this horny, and after his essay, it was doing a real number on his self image.

Frank for his part was absolutely loving it, with his tips and tricks this had gone from a great blowjob to an amazing one, yet in the end the sheer tension of a rapidly approaching orgasm still took over and all his talk of sensuality and all those other things went out of the window. Overcome by lust while on the last few sucks until his orgasm, only getting off really mattered any more. There was no reason for him to hold back either, as Sally had said, the sissy was his to do with as he pleased and so he just grabbed the ginger pigtails and served himself, pounding Jason's throat to a climax. It had happened multiple times before with Sally so Jason knew the best course of action was to just relax his throat and let it happen while feeling all the more used for it. At least it didn't take that long for Frank to cum after that as a few moments later Frank pulled out until only the tip of his cock remained in Jason's mouth as it started pulsing and spewing out cum. A smaller load, but still plenty to leave a thick coating all over the sissy's mouth, refreshing that taste of cum with had never quite gone away after the last blowjob.

When Frank finally started going limp again and pulled out of his mouth, the vibrations coming from his plug stopped. Jason was mortified, but he did carry out his earlier instructions. After swallowing everything he leaned in to place a quick peck on the tip of Frank's cock only to lean back and speak. "Thank you Master Frank for your delicious manly load out of that amazing cock of yours." As if sucking cock hadn't been awful enough, here he was saying thanks to it as if it was the greatest gift he had ever received, and while it made him shudder he also felt himself eyeing that slowly limpening cock and hoping it would get hard a third time so he could finally find some relief from that horrid arousal and the aching in his balls, a desire which only made him feel even more pathetic.

"That was great Jasmine, absolutely amazing, just look at what a good cock sucker you can be if you put your heart into it rather than only your effort. Do keep that in mind for the next man you're sucking off, I'm sure he's going to love that to bits. In any case, your essay was great, but there were a few sloppy spots, seventeen to be exact, so follow me and come lay over my lap. You've earned yourself a spanking!" Frank snickered as he casually walked over to what was now Jason's bed and sat down, not really bothering to cover himself up one bit as he admired how the sissy got up on her high heels and minced right over, her makeup a little ruined, and looking a little nervous, yet completely obedient as she lay down across his strong hairy thighs as demanded.

After all Jason had been through he couldn't believe he was still getting spanked, but he knew better than to disobey or screw up anything like his mince and such. After all a spanking was hardly a real punishment compared to the things that could happen if he really screwed up. That didn't make him feel any less embarrassed over getting onto the lap of the man he had just sucked off though. It only got worse as Frank's instructions got in. "Alright sissy, when I spank you count and I want a thank you for each and every spank, now lets start shall we?" Frank asked, not really waiting for a reply as he flipped up the short skirt and revealed the prissy panties Jason wore. He didn't even need to pull them down for a bare bottomed spanking as he rained down a first hard blow.

"One, thank you for spanking me Master Frank." Jason cried out after a quick yelp, his face turning beet red under his makeup and he was sure his ass was following as Frank clearly wasn't holding back, spanking him full force despite this not even being a real punishment yet. Maybe that was because his ass was still somewhat tender, but it got him all the more motivated not to screw up for real as he dutifully counted out one spank after the other feeling pathetic. It took some time to get to seventeen and by then they were really starting to hurt. Each spank had stung more than the last and by the last one Jason was only barely choking back tears. Finally it was over though, he thought as Frank finally released the grip he had held on his back.

"There we go Jasmine, you may get up and thank me for your spanking, then go clean up your makeup and go back to your desk, it's time for another lesson. I'm sure you are going to love this one, so hurry up. If you perform well, then at the end of this lesson I'll fuck that sissy pussy of yours with my cock the way you have been craving all this time. Especially know that I know just how much you're craving it, after all didn't you just tell me how you would have dreamed of being my fleshlight so I could fuck all of you whenever I'm in the mood?" Frank asked with a chuckle while Jason barely supressed a groan thinking about the awful twisted fantasies he had come up with to fill those last pages. Making matters worse, he couldn't even deny craving to be fucked. Even if he had mixed feelings about it, his mind screaming no, he really needed that cock inside his ass and he needed it badly. He had been trying to be good just to earn that, even now he quickly dipped into a curtesy, thanked Master Frank and minced to his vanity table to get his look back to perfection before mincing right back to his desk.

Once at the desk Jason was greeted by the sight of a paper with colourful drawing of a penis and all the structures beneath the surface with numbers and names. Next to it lay a picture of a cock in a pink cage similar to his with only one name attached to it. "Alright Jasmine, if you love cock as much as you seem to do, then I'm certain that you want to know all there is to know about it, and what better way to do that than to study the entire anatomy of a cock? You have fifteen minutes to study all of these terms, once you are done we'll do some practical exercises and after that there'll be a real test, the result of that will determine if you get to get fucked or not. Now begin." Frank simply stated as he sat back in his chair right above Jasmine's desk, loving how the sissy instantly sat down and started studying.

Although a drawn picture with so much internal organs on display that it didn't look much like an actual penis anymore was less embarrassing to look at than Frank's actual cock. It remained mortifying to learn every proper name for all the things concerning a cock and its inner workings. He was in college, yet this seemed to be the only thing where any mental capacities were required of him in this new life Sally had forced him into. The only thing he had learned so far at this twisted version of sissy school. He feared it would be the only actually thing he would learn as well, but there was no time to really think much on it as even though a few anatomical names were well within his capacity, fifteen minutes wasn't long at all to memorise something.

"Alright sissy, that's enough, please pass those sheets up to me and go kneel on the carpet over there. It's time for some more practical exercises, to see how well this knowledge translates in the real world. These practical exercises will be conducted in the same way as the test later. Only this time if you don't know something you may kiss the tip of my cock and ask me to please remind you where something is. Now as for the exercise itself, I'll read a name from this sheet of paper and you'll point it out with your tongue, or as close to it as you can get. We'll start off easy with the urethra." Frank smirked as he looked down into the cute mortified sissy's eyes, right in time to catch her correcting her glasses again with a snort.

Jason was mortified, he didn't know what he should have expected from this practical exercise of sorts, and he had known it would be bad, but this was worse than he'd imagined it being. Still he knew better than to delay, cause whether he liked it or not, he really needed that relief that would come with getting fucked. Leaning in he lifted up Frank's lip cock and pulled back the foreskin only to give the small slit at the tip of his cock a quick lick to point it out as demanded, knowing he got it right as he pulled back only to be scolded. "That was the correct answer Jasmine, but next time don't stop licking until I give you another part to point out." Frank spoke as Jason felt his freckled face turn beet red it pretty much meant that his tongue would be on some part of Frank's cock at all times.

"Alright, onto the next part, I want you to point out the scrotum, and make sure you point out all of it, so I know you really know where it is." Frank grinned, looking down as Jason lifted up his cock again, the horror yet neediness clear on his freckled face. This time Jason put his tongue on Frank's hairy wrinkly sack and got to work licking it the best he could. The hairy wrinkly texture felt awful on his tongue, but he licked it all the way around from the left side to the right side, and from the shaft to Frank's taint. He spared no effort getting under there, as he did his best to point it all out, slobbering over Frank's nutsack as if he loved it. He couldn't believe he was actually thinking this, but sucking cock had been way better than this, he especially shuddered at how close he had to get to Frank's ass.

In no hurry to move on Frank kept the sissy slobbering over his hairy balls for over a minute, before finally speaking up again. "Very good sissy! Now point out the glans." Frank smirked as Jason was more than happy to move on from that hairy sack back to the tip of Frank's cock. The smooth purple head felt so much nicer to lick, yet not any less embarrassing. Looking down with glee, Frank couldn't help but feel like he would have grown in a full fledged erection again if he hadn't just came for a second time. In either case, at this rate he would definitely have a third erection ready to give the sissy, and he couldn't wait to fuck that ass, that sweet virgin sissy ass. At this rate Jasmine was most definitely earning it.

For the next thirty minutes Frank kept on naming parts of his cock with Jason only having to debase himself twice to ask Frank for help. With the prepuce which ended up being just the foreskin, and the suspensory ligament which ended up being cantered behind Frank's pubes. Putting his tongue into that pubic bush and licking around there had been horribly disgusting. It gave Frank no physical pleasure either, yet he had kept the sissy licking his pubes for quite a while, highly amused by how low she was stooping to earn some cock. It gave him great pleasure to see, and feel the power he had over this cute, but pathetic looking sissy nerd.

"Can you point out the useless clitty Jasmine? It's okay if you can't quite reach this one with your tongue." Frank had spoken with a smirk somewhere in the middle of all the instructions. Useless clitty had been the only term linked to the picture of that caged cock, the which made it the encompassing term for what he had between his legs. It was mortifying, but not about to screw this up, Jason hiked up his skirt and pointed down to his caged member which was still giving him a ton of trouble, yet less than when he had first arrived here. It had never been taken and it wasn't looking like it was going to be taken off any time soon. For as much as it pained him. Jason actually agreed with this awful term. It really felt useless what he hid under his frilly skirts.

After Frank had had Jasmine slobbering over each and every part of his cock and surrounding his cock he finally upped the ante a little more. "Alright Jasmine, can you show me where the anus is?" He asked with glee as he watched a look of pure horror cross the sissy's face. Jason couldn't believe what he was hearing. It had been on the sheet of course, but he had never thought he would get this kind of question. It was just gross on a whole new level. For the first time he had sucked an actual cock, a rather musky one at that, not once but twice. He had just rubbed his tongue over every inch of that cock, including rummaging around through the pubes, yet now for the first time he simply couldn't bring himself to immediately do it. None of those things had come close to being as disturbing as the demand he had just gotten, and it was pretty much a demand cause everyone knew where the anus was.

"If you don't know where it is you may always ask me Jasmine, this isn't your real test yet. Of course you can feel free to think about it a little longer, but don't take too long or I might start to think you are delaying on purpose and I wouldn't be happy with that. Not at all. Let me give you a hint. If I feel like you're not giving this exercise your all my cock might never make it up your anus among with a lot more unpleasant things." Frank amusedly spoke. Of course he knew Jasmine was stalling, that she was refusing to put her tongue back there, but he wanted her to succeed, he wanted to fuck that sweet virgin sissy ass, and he wanted to feel that pierced tongue back there. Sure a strict punishment and another blowjob wouldn't be bad, but he had his preferences, and complete obedience and control were so much better than punishment to him. He guessed all the sissy needed was a little nudge, after all instead of refusing or even attempting to get out of this any other way, all she had done was delayed in silence. She had obviously become meek enough not to dare stand up to him, so all it needed was a little convincing.

Jason for his part couldn't help but awkwardly squirm on his knees a little. Despite his over arousal which had only groan over the edging during those two blowjobs he had given, this just sounded like too much. Touching this man's asshole with his tongue nearly made him gag just thinking about it, but at the same time he feared that there was no getting out of this. Frank was even stronger than Sally, and there was no way out of this room for him. His ass was still burning from the spanking he had received and that hadn't even been a real punishment. Plus he really really needed that cock to help him find relief from this insane over arousal. There was no telling when he might get another chance, or what he might have to do then, plus he doubted that after his punishment he wouldn't be told to put his tongue there anyways. Jason couldn't help but feel like Master Frank's command had already sealed his fate. That there was just no getting around it so maybe giving in was in his best interest. It didn't even fully register to him how he was trying to reason his way into obeying such a nasty demand, yet here he was, turning more and more into the pathetic sissy he was called and moulded into.

Eventually seeing how Frank was about to speak up again was the trigger Jason needed to get into action before he lost his chance. In a most awkward kneeling shuffle he got around Frank and spread open the man's butt cheeks, nearly gagging as he saw that wrinkled hole. Yet reminding himself what was at stake he leaned forward anyways and reluctantly touched the rim of that wrinkled hole with the tip of his tongue only to slowly starting to circle it, working hard to keep himself from gagging. "Very good Jasmine, I knew from the moment I first saw you that you were a real kiss ass." Frank taunted, unable to resist celebrating this victory. Jason could only groan though, hating that he was actually doing this, and the taunt made it feel all the worse, yet he had come this far so there was no point in stopping.

Frank made Jasmine lick his butthole for a good three minutes before finally speaking up again. It was what Jason had been aching for since he first started, a chance to finally move his tongue away from that asshole, but as he heard what Frank had to say, he wished he could just take that back and keep on licking Frank's rosebud. "Very well Jasmine, now there is only one term left to quiz you on I think. You can point out my prostate next." Frank chuckled knowing full well what the best way of reach that was. He just loved feeling that tongue on his butthole come to a stop in utter shock, but it never left there as Jason once again hesitated big time.

Licking Frank's butthole had been more than bad enough as it was, he couldn't believe the man now wanted him to put his tongue in there. At the same time though he once again started to reason his way in obedience, using all the same arguments in his head he had used to start licking Frank's ass, plus by now the musty taste of Frank's ass was strong on his senses already. Would it be that bad just to have at it a little bit more? Of course it would, but it was all Jason managed to do to get himself to comply with Frank's latest demand as he started pushing on that asshole he had been licking for what felt like ages. He couldn't belief he was actually doing this, he was, and with his wet slippery tongue Frank's ass didn't put up that much resistance. Before Jason knew it, he actually had the tip of his tongue into the man's ass.

"Mmm that's it Jasmine, you've got the right spirit and the right idea, but I think it's a little bit further up. You're getting there Jasmine, just push a little deeper, deeper, deeper. Almost there now, yes that's the spot!" Frank exclaimed happily, urging Jason to keep on going and going until he had his lips firmly pressed against Frank's asshole, his nose pressed deep into Frank's crack and his tongue stuffed down there as far as it would go. Right now Jason couldn't help but wish for that taste of cum back in his mouth, it was delicious compared to this, but he dutifully kept wiggling his tongue around deep inside Frank's ass, not about to lose it all now that he had come this far.

Making matters so much worse the vibrations of his plug started back up and before Jason knew it he was actually moaning with his tongue buried deep up Frank's ass. "Alright Jasmine, you'll want to really circle and prod that small bump you feel there, flick it with your tongue, pressure it, Mmmmm yes that's it!" Frank moaned out instructing Jason on how to give a proper rimjob. Jason for his part was nothing but horrified yet oh so horny. He couldn't believe he was actually moaning like he was loving this while doing something so nasty, and in essence all so he could get fucked. He had stooped even lower than ever, it was horrible. He simply couldn't help but think of how he was eating this middle aged man's ass with seemingly more passion than any of the pussies from hot college girls he had hooked up with throughout the year. It only made it all the more embarrassing.