Chapter 21

John had been looking forward to this very moment that he wasn’t about to just get it over with. He was going to savour it as much as he possibly could. These contacts proved to be such a good find. They allowed him to stay anonymous as long as he didn’t give away his voice while still not covering the sissy’s face.

A face even John had to admit was pretty. He had never really noticed it before when Marcy was still Mark but with that nice coating of soft pink lipstick, the pig tails and the way it was completely smooth it definitely had its appeal.

Still there was a lot that could be done to make Marcy even prettier. That much became clear when John stroked Marcy’s cheek with his finger, feeling the slightest trace of hairs that were starting to regrow. It looked like it was about time for another visit to the salon, but that could wait for now. He did love the way Marcy squealed when he touched her cheek.

“Please, whoever you are just please leave me alone. This isn’t what you think it is. I beg you.” Marcy whimpered in response to the touch. It was becoming clear that whoever this was had come especially for her. Had her blackmailer really thrown everything online?

John just smirked but remained silent as he opened up a suitcase, taking out a few cameras to catch some more angles than the installed ones in the room did. He then stroked Marcy’s cheek once again and pushed his thumb against Marcy’s lips. Pressing harder, obviously trying to get his thumb into the sissy’s mouth.

Marcy wasn’t about to just give in to these unspoken hints however. She firmly pressed her lips together. It seemed to work as the hand and thumb suddenly moved away. The victory was short lived however as it was instantly replaced by a severe stinging pain from a slap across the cheek that made Marcy’s ears ring.

Right after the hit the hand took its position back on her cheek with the thumb against her lips. This time Marcy obediently took it in her mouth and sucked on it softly. It tasted slightly salty and she really didn’t like the act or what it symbolised one bit. She did however realise that resistance was futile in the position she currently found herself in.

A big smirk grew on Johns face. he could feel the sissy’s cheek glow underneath his hand, the warm wet insides of her mouth felt great on his thumb. He was already thinking about where else they would feel great, but that could wait for now.

After about a minute the thumb finally moved away. For a while Marcy felt nothing, which on its own actually was worse than sucking on that nasty thumb. At least she knew what was happening when she sucked on that thumb. Not knowing made her thoughts run wild which only led to severe disturbance.

The uncertainty seemed to last forever until Marcy suddenly felt a hand on her stocking covered calf. The hand didn’t stay there very long, instead it slowly slid up along the inside of her leg. When it was nearing the tops of her stockings Marcy instinctively closed her legs, preventing the hand from advancing.

It was enough to make the hand stop for a moment, a moment in which Marcy realised this was the exact same situation as with the thumb. Afraid of another ear ringing slap in the face Marcy reluctantly opened her legs allowing the hand to travel up further.

John smirked, this was going way better than he had ever expected and he was loving every minute of it. Without a single care for Marcy’s obvious discomfort. He just continued sliding his hand up Marcy’s thigh, over the stocking tops, making his hand disappear under the sissy’s skirt while he had skin on skin contact with Marcy’s inner thigh.

After softly stroking Marcy’s inner thigh for a moment John’s hand shot straight up to the crotch of the sissy’s panties where he cupped a good feel of her caged cock. John smirked knowing that this very cage had prevented Marcy from really touching her cock for more than two weeks already. More than two weeks of fingering her butt as only form of masturbation.

Marcy groaned loudly, the way this man was feeling her up was really disturbing, especially the way he touched her cock cage trough her panties. She could tell it was a man touching her cause those hands felt anything but dainty. They were big and rough. Being touched by a man especially in such intimate spaces grossed her out completely.

Having cupped a good feel of the sissy’s caged cock John moved his hand further down to where the butt was resting on the floor. Pushing up he made his desire for her to lift her butt clear. Something Marcy reluctantly did knowing she was trapped no matter what. That first slap had proved resistance brought pain.

As Marcy’s butt rose for him John didn’t hesitate to slide his hand down further, giving each butt cheek a good squeeze, happy with how squishy it felt. Marcy might be a guy, but she certainly did have a fat butt for a guy. Still it would be nice if it was filled out even more.

At her butt John fumbled to find one end of the bow tying the panties together in the back. With a firm pull he opened up the bow which in turn opened up the heart shaped cut out framing the sissy’s butthole perfectly. Too bad he couldn’t really see it in her current position. Oh well it would just have to wait for another time then. There was no way he would unlock the cuffs after all.

Now that Marcy’s butthole was exposed John traced his finger down to the hole and started pushing right at the centre. This instantly elected a squeal from Marcy who once again started pleading. “Please no, don’t touch me, not there.” Marcy begged pathetically, but the finger kept on pushing without a word from the person with her in the room.

With the weeks of fingering and the enemas that had gone before it didn’t take all that much force for John to push his finger inside the sissy’s butt. Much to her shame it didn’t even take that long for John to get a moan out of Marcy by thrusting his finger in and out the sissy’s butt a few times. He wasn’t practiced in the slightest in how to finger a butt, but Marcy was so used to getting all her pleasure from fingering herself by now that something entering her bottom didn’t need to be all too skilful to yield results.

After that first moan John pulled his finger out of Marcy’s butthole and disappeared from touching distance once more. Marcy’s whole face was beet red as she worried about what was next. It was becoming clear that this person in her room had more than just touching in mind after having violated her butt like that.

John gave his finger that had just come out of the sissy ass a thorough sniff, mainly out of curiosity. He was really pleasantly surprised that it literally smelled like roses. A clean sweet-smelling hole ready for use, but that was for another time. He had something else in mind for this visit.

All Marcy had to go off now was the fumbling around she heard rather close to her. It was worrying and yet she had no idea what it was at the same time. Maybe that was what worried her the most though. The fumbling suddenly stopped and once again the hand went straight to her bottom signalling her to raise her butt.

When she did, she was surprised by something cold slick and rather hard pressing against her butthole. Whatever it was she didn’t like where this was headed, but with that thing positioned underneath her there was no way she could sit back down to prevent whatever it was for. Sitting down would only force it straight up her butt.

Straight up her butt faster that is, with the pressure starting to mount it looked that those were the exact intentions of whoever was with her in the room. At first her sphincter gave way allowing a relatively small angled head to pop in. The thing became wider and wider however until all of a sudden the sphincter rapidly closed around a very narrow base. All of a sudden she realised exactly what the thing was. It was a butt plug. A strange one for sure. The tip seemed to be slightly angled pressing right into the sweet spot she always sought out when fingering herself.

Taking a step back John smile. The sissy was nearly ready for the real fun. Now for a test of that new plug he had just given Marcy. It had some cool features which he couldn’t wait to try out. If it worked as the woman in the sex shop had promised it would be a great new toy.

Fishing out his phone John opened an app and tapped a button on screen. While he couldn’t really see or hear the device, Marcy’s sudden surprised squeal followed by a deep moan made it clear it worked as intended. Instantly John pushed the button again making it stop.

Marcy was in shock after the sudden vibrations concentrated right on that sweet spot sending an instant jolt of intense pleasure through her body. It was more intense than anything she could do with her fingers much to her shame. She didn’t like the fact that this stranger could make her moan practically on command. Probably cum on near command as well. With this device it probably wouldn’t take long to get to an orgasm.

All of a sudden Marcy got shaken up again. This time by a sudden vice grip at the sides of her jaw. It hurt like hell leaving her now other choice but to open her mouth in an attempt to ease the pain. When she did she could feel something cold being worked between her teeth in a rush before the tension finally eased. She tried closing her mouth again, but it had become impossible. There was something stuck in her mouth forcing her to keep it open wide while a strap got buckled behind her head.

John smirked admiring his handy work. Now Marcy really was at his mercy, a sissy completely prettied up especially for him, a fat plug in her ass under his control and a wide-open mouth waiting for him to use. There would have probably been a lot of defiance at what would come next, but that was all taken care off there was nothing the sissy could do anymore, nothing but riding this whole experience out.

Touching and preparing the sissy had turned John on a lot. Normally he would have long taken care of it by jerking another load into his boxers. Not this time though. Now he could finally reap the fruits of his patience and preparation as he sighed in relief, releasing his big already rock-hard cock from the confinement of his pants letting it stand at attention pointing right at the sissy’s face, even if she couldn’t see it. A strong musky smell of stale cum, fresh precum, stale pee and some sweat emanated from his crotch. A smell the sissy would certainly recognise.

Although she couldn’t see Marcy’s expression instantly changed to one of intense shock as she recognised the smell of her blackmailer’s cock. It was that same smell she had been cumming to since that one fateful day. That nasty smell those boxers always had, but way more intense than what she was used to. Hell she even knew what it looked like after sucking that damn dildo so many times. Only this one was real, flesh and blood, throbbing alive, and she had a bad feeling she knew where it was going to

She wanted to scream, to run, to fight, hell even to bite that awful cock in front of her, but she couldn’t do any of that. All that she could really do was sit there and wait for the cock to enter her open mouth. A tear rolled down her cheek as she realised how hopeless her situation was, not even able to beg using any intelligible sounds with her mouth forced open.

John was relishing the sight before him, the sight of his helpless terrified sissy. Thanks to the contact lenses instead of a blindfold he could witness all the facial expressions perfectly. Taking a step forward he lifted his cock, positioned himself right over the sissy’s face and let it slap down with a smirk.

A squeal distorted by the ring gag escaped Marcy’s mouth as she was suddenly smacked in the face with a real cock. It was disgusting. She could feel how it was slightly sweaty, hell she could even feel the pulse as it rested across her face. It felt incredibly warm as well.

Without letting his cock break contact with the sissy’s face John moved forward. Running his cock over Marcy’s face and positioning it so that his hairy wrinkly sack was hanging over the sissy’s mouth, one ball hanging a bit lower within her mouth. His cock lay right over top of the sissy’s nose.

Marcy felt grossed out of her mind. Her nose was stuck right against the skin of this sweaty ball sack, engulfed in pubic hair which tickled the insides of her nose in a disgusting manner while the cock lay pulsing on top. It had that same gross smell as the front of those boxers, only this time it was at least 10 times stronger making her feel nauseous. Despite how much she was screaming inside this overly intense version of the smell she had been masturbating to all these weeks, also had another effect on her apart from grossing her out.

Much to her horror her own cock was straining hard against its cage. Not being able to touch herself there she hadn’t really paid a lot of notice to her cock lately. She didn’t even realise the worrying signs that her cock didn’t seem to get hard at all anymore lately, well not until now at least. Even now with that intense familiar scent that awful pressure didn’t stay on long. It came more in waves of trying to get hard but growing soft again when it hurt too much. It didn’t keep painfully straining against the cage like the first attempted erections she had had while wearing this cage.

What bothered her even more than that smell was the hairy testicle hanging slightly in her mouth. Her first reaction was to try to push it out, the only way she could, with her tongue. After attempting that it instantly became clear that it was the worst possible idea however. All it got her was a disgusting salty musty taste and the ball sinking right back in her mouth under the force of gravity. All it really accomplished was a firm lick, or at least that how it must seem like to her blackmailer. After that first attempt, she just kept her tongue as far back in her mouth as she could.

John wanted to tell her to keep on licking his balls, god he wanted to rub in what her position was so badly, but he knew talking would give away who he was, so he restrained himself. Besides it wasn’t like he could complain at all having his cock laying across the sissy’s face. In fact he was very pleased to see how the intense smell of his cock turned the sissy on. Not that he could tell with her cock locked, in panties and under a skirt. He could tell by looking at the plug’s app though.

Apart from being a vibrating plug highly specialised in delivering maximum stimulation to the prostate, it was also a highly technological device. It gave a reading of how turned on someone was by measuring the pressure the prostate exerted on it as well as reading the temperature of the device so one could see if it was within a body or not. The base had a few electrodes that could sent feint pulses to the surrounding muscles making them clench and strengthening them so the butt would remain very tight.

With the push of a button John made the plug in the sissy’s bottom vibrate again, making her moan underneath his cock much to his sadistic satisfaction. Oh this video would become so great, the sissy getting ready for her Daddy, then moaning when she finally got up close and personal with it. After that one moan John once again shut of the vibrations.

Of course Marcy could always deny she didn’t moan because of what looked like sucking his balls. Then she would have to admit she was getting off on that big plug in her butt though and John doubted she wanted to admit to that. There really was no other explanation for this than her being a depraved sissy, no matter how she twisted or turned it. Even if she delivered proof of the blackmail John could always claim it was a kinky game she liked to play. After all no matter the explanation that moan was damning evidence.

After letting his dick rest right there for a few minutes John finally started moving again. He moved back this time. His dick slowly slid down Marcy’s forehead, over the bridge of her nose, falling just underneath her nose before finally coming to rest on her chin and under lip, the tip hanging right above her open mouth. When moving down her face the tip had left behind a slimy strong-smelling trail of precum in a straight line from her forehead to her upper lip.

Marcy knew exactly what was coming next and she dreaded it with every fibre in her body. Yet cuffed to her bed with a ring gag in her mouth she could do nothing to stop her blackmailer from having his way with her. The feeling of dread was growing constantly as her blackmailer’s cock rested above her open mouth, putting off the inevitable insertion for now.

Having let the dread increase for a while John finally progressed. With a slow steady movement John guided his cock in the sissy’s wide-open mouth. Just the tip for now. He wanted Marcy to savour the full extend that came with that smell she had been conditioned to get aroused for. With that in mind John slowly rubbed the tip of his unwashed cock, sticky with thick precum up and down the sissy’s tongue.

She groaned to signal her disgust. The cock tasted salty, musty, somewhat bitter and with a light acrid undertone. Yet no matter how much she tried she couldn’t bend her tongue enough to prevent the velvety cock head from rubbing over it. To make matters worse the vibration right on that special spot started up once more making her moan involuntarily, the vibrations were way softer this time, but they continued unlike the quick intense bursts from earlier.

Using the specialised app John had started a sequence that would bring Marcy right to the edge of an orgasm, but no further. He liked the idea of keeping the sissy highly aroused and moaning while using her mouth. Besides it would be perfect for the little video he would make off it. At this point he had started Marcy’s website by montaging old video material he had of the sissy’s transformation, but in due time this video would also make the site and he was certain it would become a hit.

John was surprised by how good just rubbing the tip of his cock on the sissy’s tongue actually felt. So good that he had to stop himself earlier than he had wanted to. After all he didn’t want to grow overtly aroused before the real fun started. Besides, he was pretty sure that the goal of this little warm up had already succeeded. The sissy just had to have a good understanding on what his unwashed cock tasted like by now.

Proceeding with his fun John surprised Marcy by suddenly continuing to slide down instead of going up again near the end of her tongue like he had been doing for a while now. Little by little he kept pushing his cock deeper inside the sissy’s mouth until hitting the back off her throat.

From deepthroating her dildo which really felt like a cold none pulsing version of the cock currently in her mouth, Marcy realised this was only the beginning. She was barely halfway to a deepthroat now and the big second half was way harder than the small first half.

Nevertheless, John kept pressing on, only encountering light resistance from Marcy’s throat muscles. The deepthroat training with the dildo was paying off for sure as John’s cock went deeper and deeper down Marcy’s throat until his balls were resting against her chin and her nose was buried deep into his strong-smelling pubes. There was some gagging but mixed in with the sissy’s moaning that only made it hotter for John, especially the way Marcy’s gag reflex massaged his cock.

Not wanting to suffocate the sissy John started pulling out again until just the tip of his cock remained in the sissy’s mouth. An opportunity Marcy gladly took to take a deep breath. She felt so gross and violated, but now survival was more important. She would have to breath when she could since the cock was already working its way back down her throat once more. Faster this time.

Just like that John slowly picked up his pace, settling into a nice rhythm to face fuck the sissy to. With the pace ever increasing he had to grab onto Marcy’s pigtails at one point to be able to have enough grip. Soon he was using Marcy as nothing more than a glorified flesh light with handles to it, while the sissy was helplessly moaning and gagging underneath him, catching breaths whenever possible.

It didn’t take long for him to approach an orgasm, the combination of the complete power trip along with the fact that this was his first-time having sex with a real human since his wife divorced him a couple years back, were just too much.

Forcing himself to redirect his attention John turned back to his phone for a second, quickly initiating the pre-set sequence to push Marcy over the edge with a few seconds delay. He wanted the sissy to cum when he did, and he was very close.

A few quick thrusts later John was ready to blow his load, but just as his cock was starting to tense up, he pulled out of the sissy’s mouth. Instead of cumming deep down Marcy’s throat he painted the sissy’s face with rope after rope of thick sticky warm cum. It was the biggest orgasm he had had in recent years and it was evident by the sheer amount of cum covering Marcy’s face. It was positively coated.

Not wanting to deny the sissy the taste of his cum, John scooped some off Marcy’s chin with the tip of his cock and reinserted it back into the sissy’s mouth. Just like he had done before he rubbed his cock up and down the sissy’s tongue leaving a good coating off cum behind before definitively pulling out.

Marcy felt awful she felt disgusted with the big load covering her face. Hell she felt disgusted with herself having orgasmed with a loud moan herself when the ropes of cum started splashing on her face. in union with her blackmailers cock she had filled up her panties with a small load of cum leaking out the tip of her cage. The salty bitter taste of cum was strong in her mouth and there was no way out of this situation.

John just stepped back and smirked. He put away the extra cameras he had set up and knelt down before Marcy for the last step of his visit. He lifted up the sissy’s skirt and pulled down her sticky panties. Taking his copy of the key John unlocked the sissy’s cock for the first time in a long time. John still considered himself completely straight, after all he didn’t consider Marcy a guy at all, and the soft cum covered thing between her legs certainly wasn’t a cock in his eyes. He would have to check his videos from the beginning, but he was nearly certain it was smaller than in the beginning.

Casually John slid off the tube that connected to the ring behind the balls, leaving that ring in place. He then took a cold pack and pressed it against Marcy’s cock making it shrink even more. He then replaced the tube with a significantly smaller one he had gotten from Linda, one so small that it was a tight fit even in its ice shrunk state. He then neatly locked it back up, packed his bag and left the whimpering sissy alone, retreating to his house.

Marcy’s mind was in turmoil, shocked beyond believe at what had just happened, she didn’t want to believe it even, but between the taste of cum in her mouth, the feeling of drying ropes of cum on her face, the plug in her bottom and her sore throat there really was no denying it. It got only worse as her cock warmed up again trying to go to its normal soft state only to be painfully contained by the current smaller tube.

After about 20 minutes which seemed like an eternity to Marcy the speakers in her room cracked back to life. “Hello sissy, that was fun wasn’t it? I’m so glad to see you enjoyed sucking my cock as much as I loved getting it sucked by you. At least that’s what that load in your panties told me.”

“You’ve doubtlessly found out by now that the cuffs don’t really have a key or lock. They are locked remotely, they can only be opened using a corresponding app. I’m going to unlock them in a few minutes, but before I do I want to make somethings clear so listen carefully. I have made a video of our little encounter that just happened and if you don’t do exactly as I say an anonymous copy will end up on your dad’s desk at the lawyer firm he works at. It will have a note claiming to have evidence of a sensitive high-profile case so he’ll surely watch it himself right away. I bet he’ll love to see how you get all prettied up just to suck my cock and moan like a bitch in heat.” John said in the computer distorted voice giving some time to let the threat sink in.

Marcy was terrified. Her stomach turned to knots as she imagined her dad or anyone seeing a video like that. Hell even she wouldn’t want to see it at all. Having lived through it once was more than bad enough already.

“First of all my cum is to remain on your face until tomorrow morning when you shower. Since I am generous and don’t want to be too hard on you, you can lick up whatever you can reach with your tongue.” John said grinning behind his computer.

“Secondly, from now on you can forget about fingering yourself. As you might have noticed that plug is more than capable of giving you an orgasm. I can control it using an app and will do so. From now on that plug stays in your bottom unless I tell you otherwise. If your girlfriend or whoever wants to take it out to use your hole they can as well, but you are never to take it out or suggest taking it out yourself. Not unless it is for your morning or evening enema. The plug has its own sim card and is connected to the mobile network. In your room I left a charging station with a rechargeable battery. Along with your enema you should switch the battery in your plug with the one in the charging station. The battery should last 24 hours, but to make sure you are going to switch and recharge them with every enema.” John informed.

“Of course you can beg me for an orgasm whenever you want one, I’m not cruel after all. Oh and before you think of taking it out to sneak your fingers in anyway, the plug is heat sensitive so if the temperature drops well below body temperature I will know.” John added.

“The last rule is that you should stay in that outfit for the remainder of the day. You should really train in walking with those heels some more. If you understand these three simple rules then give me a nice loud moan, you’ve already proven that you can moan very well.” John finished his set off rules.

With the ring gag still in her mouth Marcy couldn’t really reply coherently. She let out a loud and pitiful moan, terrified over how the control from her blackmailer had just tightened a lot. Although her face was covered in his cum she still had no idea who was behind this and thus still had no one to confront about this whole mess.

While fingering herself to an orgasm had been very humiliating, she had at least been in control of her own orgasms up until now. This plug basically meant that she was completely reliant on others if she ever wanted an orgasm again, but if this asshole thought she would ever beg for an orgasm he was sorely mistaken, Marcy thought bitterly.

A sudden click was heard throughout the room and the cuffs fell open, finally releasing Marcy’s wrists from the posts at the foot of her bed. The first thing she did was removing those damn dark contact lenses from her eyes. Moving around with these heels was hard enough on its own that it didn’t need to get any harder by not being able to see. She then quickly removed the ring gag, unbuckling it from behind her head.

Now that she could see again she dreadfully got up and minced over to her mirror. She was horrified seeing her slightly roughed up pigtails and her face coated in cum. Not wanting to be confronted by the sight any longer she quickly turned away. Thanks to the rules she was stuck in her room after all there was no way she was going anywhere with her face plastered in cum, dressed as she was.

God she wanted to wipe that cum coating off so badly, feeling it stick and dry to her face was a constant source of disgust. The also couldn’t seem to get rid of that awful taste of cum and cock. Despite how bad she hated it she was too afraid to do anything about it.

With nothing else to do Marcy turned to her computer and started up a game. It was all she could do to hope to forget about the entire situations. Even that proved impossible as suddenly random intense vibrations attacked her prostate.

It was simply impossible to concentrate well enough not to get harassed by her team in the shooter games she liked to play. As a last resort Marcy switched over to watching movies on he computer. She didn’t really feel like it, but it was the best she could do to distract her right now. The random intense vibrations kept happening, slowly pushing her to the edge once more and maintaining the arousal.

As the day dragged on the constant pressure of intense arousal started to wear down Marcy’s resolve. Suddenly she wasn’t so sure anymore that she wouldn’t end up begging for an orgasm like she had thought earlier. God she needed some relieve, she needed it badly but she didn’t want to give in to that asshole.

Yet she was so horny that relief was all that was on her mind by the time bedtime arrived. Maybe just maybe she could push herself over the edge with the nozzle from her enema kit. That was the solution for her problem. That way she could relieve herself each and every day so she wouldn’t have to cave in and beg for an orgasm to her blackmailer.

Weird as it was she actually couldn’t wait to give herself that enema so she could cum. She was too horny to even realise how drastic her train of thought regarding the enema had just changed. This morning she hated the nozzle, finding it much worse than her fingers because of its cock shape, now she couldn’t wait to fuck her ass with it.

Stripping down to her lingerie Marcy prepared her enema and was just about ready to remove her plug when the speakers cracked to life again. “You may remove your plug sissy, but I’ll be watching if you dare cum with your enema kit I’m sending our video from earlier straight to your dad’s mailbox, so keep that in mind.” The room then fell silent again.

Marcy was shocked here whole plan had just been shattered, she was so horny that she even shortly considered begging for an orgasm anyways. Even if it meant begging to fuck herself with that enema nozzle. Despite her need for an orgasm Marcy decided to stay strong and resist the urge to beg. After everything that bastard had done to her today she really didn’t want to give him any satisfaction.

Giving herself an enema while not cumming proved very difficult with how aroused she was already. Not only was she way more sensitive, not needing much more stimulation to get over the edge. The desire to cum was so big that it took all her willpower not to just thrust that nozzle a few times to put her over the edge. It was challenging, but eventually she did manage to succeed at flushing her insides, switching the batteries in her plug and reinsert it.

With the plug back in place Marcy went to bed and remembered just in time to set her alarm for tomorrow. Yet another dreaded day awaited her as she was supposed to work at CC’s to earn this horrible outfit she had just worn for her blackmailer back. Just the thought of returning to that store filled her with dread, whatever work she would have to do she would hate it for sure. She hated everything Linda had come up with already.

Sleep did not come easy with a face full of dried up cum, a painful dick from the new chastity cage, a sore throat and being insanely horny. It took a while, but in the end Marcy did manage to drift off to sleep.

(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)