The Sissy App Experiment Pt.4 (Patreon)

Chapter 7

Fully ready to go running in his new and improved outfit Luke looked wonderful. The tight spandex shorts, paired with his tucked back cock and well trained bubble butt gave it a decisively feminine look. The knee high socks only made it look cuter, enhancing Luke’s now shapely legs. Between them and the shorts there was still plenty of his now shapely smooth legs left bare. His top remained very flat chested though, paired with his baby face and his now lengthening hair he looked quite androgenous, not quite guy anymore, but definitely not very feminine either although his outfit gave a more girly overall appearance.

He was just ready to leave when another message from his app came in. “Dear CC Trainee, to make working out so much more fun and to motivate our users we’ve set up a workout buddy program to bring together users that live close by. Since you are still rather low in rank you will get paired with someone outranking you. That way you can learn from the best. They in turn get a chance to share and help others with what they learned. Your first workout date has been arranged with someone you might know already, Mistress Olivia. A route has been established to her house, have fun!”

With that Olivia’s profile pic popped up and Luke instantly recognised her as the woman who had gifted him his waxing at the salon. Luke didn’t even question the title Mistress at all. It was just her rank after all, the female equivalent of those who reached the rank of Master. If anything Luke was excited to learn from his superiors so with an extra skip in his step he started on his way to Olivia’s house, in a neighbourhood he recognised from one of his previous runs. Since she lived well within reach of campus it was perfectly reasonable that the app would create routes with similar parts for multiple users.

At her place Olivia was already waiting, giddy with excitement. Finally she would get to have some face to face contact with Luke who was starting to look cuter and cuter every day. She had been warned by the app that for now the work out appearance still needed to be kept up, but that she could take quite a bit of liberty doing with the sissy what she wanted if it was explained properly.

Olivia had put on a pair of light blue spandex short shorts with pink stripes at the sides, a matching sports bra, pink knee-high compression socs and a pair of light blue sneakers. She was determined to blow Luke away, cause despite all the cum he had already gobbled up he was fully straight. Seeing him approach in his new outfit Olivia’s excitement for this opportunity only grew, he looked spectacular. “Hello Trainee Luke, I guess we’re workout buddies for today. So let’s continue on our run shall we?” Olivia asked as she started running ahead, not giving Luke time to slow down as he had to catch up with her instead.

“Hello Mistress Olivia, pleased to meet you. It’s an honour to be allowed to go on a run with a superior like you. I couldn’t ask for anything better to celebrate my advancement in the app’s ranks.” Luke said excitedly as Olivia’s smirk only grew. Being called Mistress sent a thrill down her spine unlike any other she had ever felt before.

The run itself while fun was nothing all to special it ended up mainly being an opportunity to talk and an excuse for some interval training where Olivia had Carl make an occasional sprint before letting him slow down to a jog until she caught up. She loved the way she had a perfect view of his ass that jiggled so deliciously in the tight shimmery spandex shorts.

Pretty much all of the conversation they had was directed by Olivia asking questions. Questions that would have been way to intrusive for him to answer before his contact with the app. She seemed especially interested in his take on the protein shots, how they tasted, how he liked their texture,… She simply loved hearing his praise for what was in all essence nothing more than cum. Especially the recollection of just how much he had enjoyed his cream pie this morning got Olivia so wet.

Eventually after quite an intense run Luke and Olivia arrived back at her place, both soaked in sweat. “Phew that was quite the run now wasn’t it Trainee Luke, now before you go I cooked up a little stretch routine to help guide you through. The first pose I want you to try and emulate is this one.” Olivia explained as she showed Luke a picture of her in her workout clothes with her face down and ass up, arms stretched out in front of her. It looked amazing to him and just like when he had first seen Mistress Olivia on his arrival here it made his tuck very uncomfortable. While Olivia wasn’t exactly a bombshell that blew you away, she was definitely a looker and seeing her in her sexy workout clothes and now this pose on picture didn’t miss it’s effect on his hormone filled body.

Not pondering too much on how sexy it looked Luke quickly assumed the position shown by Mistress Olivia. Stretching was important after all and he wasn’t about to question someone so much higher in rank than him. “That’s great, but it can use some improvement, here let me help you a little.” Olivia said as she took of her shoe and put her damp socked foot down on his upper back in complete disrespect, forcing his torso further while she reached an arm between his legs on his crotch only to pull his hips and ass further up putting his bottom on further display. The sudden hand on Luke’s tucked back cock that was trying to grow hard against the very tight rather strong thong felt very intrusive as he instantly let out a surprised yelp, blushing furiously over how this woman was handling him.

“There we go Trainee Luke, that’s a lot better already I’m sorry for this rather hands on approach, but it’s the best way to correct your posture. I can feel you have a lot of built up tension so this is more than necessary.” Olivia explained with a broad grin, as she stroked his hardening tucked back cock through the thin layer of cotton and spandex until Luke let out a loud moan. It was hard to compose her giggling at that moment, god this workout was only getting more and more fun.

“Thank you for helping mmmme Mistress Olivia.” Luke exclaimed with a loud moan and a gasp. He couldn’t believe this was happening, just like he couldn’t believe he couldn’t keep his moaning under control. Instead of feeling shocked at how Olivia was handling him though he felt worried about offending her with his inability to control himself. After all she was only helping and giving that she had reached the rank of Mistress she obviously knew what she was doing.

“It’s my pleasure Trainee Luke. It’s my pleasure giving back for al what the CC’s app has done for me already. I want nothing more than to help you just like I’ve been helped.” Olivia lied as her hand on his tucked back cock kept stroking while her free hand traced the rounding of his bubble butt. She ended up getting Luke right to the edge of an orgasm before abruptly stopping and ordering Luke in a new equally exposing pose only to repeat the cycle of having her hand on him and edging him once more.

After trying a multitude of different poses Luke was very flustered from the constant edging. Olivia in turn was equally flustered from the sheer power trip she felt from having such control over someone, especially such a cute big bottomed sissy. It sucked that she couldn’t have him take care of her arousal just yet, but the main course of the workout she was about to introduce now would do nicely as well.

“While you were stretching I felt a lot of remaining tension in that cute bottom of yours. In order to remove the last kinks I think a massage is in order. This might feel a bit awkward, but trust me, that bottom of yours is going to thank me later. Now just come over here and lay down across my lap and we can get started.” Olivia said as she sat down and patted her lap. Her voice was a bit breathlessly from sheer arousal as she was looking forward to administering Luke’s first real spanking.

Luke’s flustered face turned beet red as he could already imagine what laying across Mistress Olivia’s lap would end up looking like. Nevertheless he got into position without much hesitation. Luke could still grasp how things might look to an outsider, but due to all the subliminal messaging implanted by the app he couldn’t see how this was in fact so very wrong, instead all he could see was how refusing Mistress Olivia’s generous help would be not done.

With Luke over her lap Olivia didn’t waste any time at all, with a swift movement she hooked her thumbs in the waistband of his spandex shorts and swiftly pulled them down revealing his plump smooth butt cheeks split in the middle by the back of his thong. “I’m sorry sweety, but this is absolutely necessary, the less obstructions the better for our massage. Now this is a deep tissue massage so it might hurt a little.” Olivia explained with a smirk as she landed a quick hard blow on one of his exposed butt cheeks making it jiggle as Luke yelped. A bright red imprint was left when Olivia pulled back her hand.

Seeing the evidence of her first slap, her mark left on this sissy’s cute otherwise spotless bubble butt Olivia was besides herself with arousal. Not waiting more than a second a second blow rained down on Luke’s ass followed by a third, a fourth,… In a power and lust drunk daze Olivia kept spanking Luke’s bottom without any sign of stopping. It was such a turn on that she got carried away until Luke’s legs were starting to kick a little too wildly and sobbing was starting to set in. She felt better than ever, but looking down on Luke’s now flaming red ass she felt a little guilty as well, maybe she had gotten carried away a little.

Olivia just hoped that she hadn’t taken this too far for Luke’s first real spanking, after all she didn’t want to be responsible for the failure of this very promising experiment. “There’s no need to sob I know it might feel a little painful and sore right now, but trust me, you will thank me in the long run.” Olivia said as she gently rubbed his buttocks. It was a bit of a nonsense explanation, but given how well he had already reacted to all her other arguing including the one that had led to him finding himself over her lap she hoped it would take.

“Th…thank you Mistress Olivia, it wasn’t quite what I expected when you said massage, but I trust you know what you are doing way better than I do.” Luke said, hurting a little was an understatement, but this was all just to help him improve right? He hadn’t really heard of sore bottoms yet, but a lot of athletes were sore the day after an intense workout right? This was probably just part of such soreness right? His brain argued to make it fit the picture he was made to believe by all his conditioning.

A broad smile spread across Olivia’s face, her little argument seemed to have worked. “That’s alright, you can thank me by returning the favour. So why don’t you get down on your knees and give me a good foot rub? That’s where most of my remaining tension post stretching is.” She said as she pulled her hands off of Luke’s bottom and back, leaving him free to get off her lap, something he quickly did, pulling his shorts back up, whimpering lightly as the tight spandex moved over the sore flesh.

Luke didn’t even question the difference in massages for him and Mistress Olivia, instead he just took her still slightly damp socked feet in his hands and started kneading her soles. If anything he was just happy that he was able to repay Mistress Olivia for all her guidance and her wonderful company. His bottom might be sore, his balls might be aching after all the edging he had been put through, but he was more than satisfied over what once again was a very successful workout as far as he was concerned.

For the next 20 minutes Luke just massaged Mistress Olivia’s feet to the best of his capabilities while she leaned back and relaxed, letting out the occasional satisfied moan in the process. A foot rub after a long run was amazing, as was the fact that she had a sissy slaving away at her sweaty feet. She simply loved it. The only hard part was resisting the urge to start rubbing her pussy, that would have to wait until after he was gone.

“Alright Trainee Luke, that’s enough. It was a pleasure sharing my workout knowledge with you and I sure hope we’ll get paired up for the buddy program again, hopefully soon. Before you go I’ve cooked up a little extra surprise for you. Just wait right here, I’ll be right back.” Olivia said as she disappeared from view for a moment only to return a few moments later with a small cup holding a pearly white liquid that smelled a lot like Luke’s protein shots.

While Olivia didn’t consider herself to be a slut or anything, she had had a couple of sex dates the moment she knew she would get to meet Luke for real. For her it hadn’t even been for the sex as much as it was about the thought of being able to cuckold Luke. Sadly she couldn’t yet make him watch as she fucked a guy right before his eyes only to have him lick her clean right after, but that thought had made her wild and excited beyond believe during her dates.

None of the men had had any complaints as all of them had their mind blown. Hell wit how she basically jumped them they didn’t even complain about having to wear a condom as Olivia rode them like there was no tomorrow. She had been on top, she had set the pace, hell she had even made them feel slightly used like they were a living dildo to her, but none of the men had really cared much as it was probably the most amazing sex they had had. Olivia had gone crazy on their cocks and through out the dates she had milked at least three loads out of each guy while having multiple more orgasms herself.

She could appreciate a nice man with a great dick for sure, but all she could think about when riding these guys to an orgasm was how the contents of the condoms they filled would make it into the teacup in her fridge. A cup that was nearly overflowing right now with more than a dozen loads of cum. Having Luke eat her out might be impossible just now. Although she guessed that seeing how Luke was very much into women and the fact that he seemed to think she was quite hot if his ogling was something to go off, she would probably be able to seduce him without interfering with the app’s progress too much.

Still she decided to play on the side of caution as the owner of the app had told her and all others that sex was strictly off limits. She didn’t want to lose the opportunity of further playing with this budding sissy over seducing him. It’s not like she could complain at all with how today had gone so far. Luke had looked so hot in his effeminate running outfit with his nicely waxed body and spanking that overdeveloped but had been amazing.

Besides if he drunk the contents of this cup, which she was sure he would given how he had demonstrated on his social page how he absolutely loved his “protein supplements”, then it would be nearly the same as eating a load from her pussy. After all, all of the cum in this cup had been shot into he pussy first. She had milked all of these guys dry during sex and it was the result of that Luke would end up swallowing. It was a good thing she was sweating so much or the obscene amount of “crotch sweat” that was in fact her soaking through her panties and leggings would be way too obvious.

“Here you go sweety, I’m kind of at where I want to be right now so I put my protein supplements aside. You look like you could use some more though to make that already spectacular progress you have been making even more spectacular. You’re surely well on your way to becoming a real looker.” Olivia said with a wink on her return handing him the cold nearly overflowing cup of cum. God she was having a hard time maintaining a straight face saying that, he was turning into a real looker for sure, just not the way he imagined it when he started working out.

Luke’s eyes went wide with sheer joy as he noticed this cup which held more protein than he had ever seen, even more than he had gotten to enjoy with his cupcake. It looked and smelled so delicious that he spontaneously licked his lips and started salivating. “Thank you very much Mistress Olivia, you are the best, simply too kind.” Luke gushed as he eagerly took the cup from her.

With eagerness rather than hesitation Luke brought the cup to his lips and gave it a deep sniff, letting out an approving moan. It took Luke quite a few sips to finish the cup and he was quite clearly savouring each and every one showing off perfectly how well the post hypnotic suggestions were working. So far his protein shots had almost always been mixed with food safe from what he scooped out of the vials with his fingers. Then again the cum he got that way was nothing compared to the cup he was eagerly drinking down now, mouthful after mouth full of pure undiluted cum with nothing to mask the taste. From the look on his face Luke didn’t seem to mind one bit, in fact the opposite was true.

Fuck Olivia thought as she was having a terribly hard time maintaining her composure as she intensely watched this scene unfold. It was hot beyond anything she had ever seen before, hell it was way hotter than she had dared to imagine. Not only did Luke drink the cum from all her lovers these past few days, no he was savouring it like a fine wine, taking small sip after small sip from the thick sticky white fluid, swishing it around in his mouth before swallowing it all.

She wished she could just masturbate right here and now as she thought back how she had emptied each and everyone of the used condoms these past few days into that cup. She thought back to the orgasmic looks from her lovers as they filled the rubbers. All loads that were now making it into Luke’s mouth. If only her lovers knew their cum was cherished like this, if only Luke knew he was drinking the sperm of multiple men, the results of many hot steamy dates. No one knew except for her though and she couldn’t get enough from the sight.

“You may, *cough cough* you may lick the cup empty if you enjoy it so much, it would be a shame to waste and I won’t think it’s inappropriate.” Olivia said, having to try hard not let her arousal be heard by Luke, fuck she could swear she was so close to moaning as the now slightly blushing yet excited guy eagerly worked his tongue around the walls of the cup to really get each and every drop of cum. Just like licking a plate clean it was rather inappropriate, but Luke looked relieved to get permission to do so.

Once he was done Luke handed the squeaky clean cup back to Olivia. “Thank you so much Mistress Olivia, you have been way to generous and kind. To me, first a massage and now this. I certainly hope we can get paired up again as well. Working out with you as well as the post workout have been absolutely amazing. Having a work out buddy is so much better than working out alone I would literally recommend this app to everyone I know as soon as it is out of the tester phase.” Luke gushed as Olivia once again had to supress a laugh the stench of cum breath wafting out of Luke’s mouth being strong enough for her to smell it from where she stood. It was a bit nasty, but above all so exciting.

“Once again, so do I, in any case I think you’ll better be on your way now. I still have things to take care off. It was nice meeting you in person trainee Luke. I’ll make sure to save up all my protein until next time we meat.” Olivia spoke as she sent him on his way with a playful pat to his sore bottom, god she was going to miss spanking and feeling that cute butt off his. Quickly saying his goodbye’s Luke soon left on his way back to his dorm feeling better than ever. This had been spectacular in all regards.

Olivia hadn’t lied when she said she had things to take care off as she instantly rushed inside her house and up to her bedroom where she fingered herself silly to the events of this morning. God this had been so much better than she could have ever dreamed. She meant it when she said she could hardly wait to see Luke again. Mmmm, she loved the idea of how he was still tasting the cum she had collected at this very moment, with how he had savoured the contents of the cup, the contents of all those used condoms Olivia doubted that he would brush his teeth when he got home, he’d probably want to savour the taste until it was completely faded.

Despite the relatively hard workout he had just had Luke’s run home basically felt like nothing at all. With his head on cloud nine he imagined the big dose of proteins he had just had working throughout his body, building muscle with every movement. Olivia might have decided to stop using the protein provided in the program because she had achieved her goals, but Luke doubted he could ever do that. It was just so delicious. Even if he had his desired body he already knew he would keep on taking the protein just because he like everything about it so much. The moment he arrived Luke instantly went for a shower, dressing in one of his new thongs the moment he got out.

The unfamiliar feeling of the slippery fabric these pink thongs were made off felt simply amazing on his perfectly smooth skin, so good even that paired with his experiences from this morning working out with this beautiful Mistress achieving a tuck was impossible. Just like he often did he masturbated, depositing his load in a tissue like he often did without noticing how it was basically another protein shot. After all he paid it no further attention, it was cum and cum was gross. Without thinking on it he threw the tissue in the toilet and flushed it.

Now that his carnal needs had been taken of achieving a tuck was a piece of cake. It basically cost no efforts at all as he was so used to it by now. Just like he was used of the material of his thong rubbing up against his butthole by now. None of it bothered him anymore, instead all he felt was excitement over this new fabric even though it was pink. He could most definitely get used to wearing these on a daily basis. In fact since he had nowhere he really needed to go he decided to just walk around in his thong for now as he went on to cook his lunch, adding as much of the protein as prescribed to equally spread all vials over all his meals until a new meal box would arrive.

With how much time his workouts and maintaining his social media presence took up Luke had hardly been able to work for school, something he decided to rectify right after his meal. Opening his books he retreated to his desk to get some work done. He didn’t get very far though as after barely an hour of studying his phone lit up wit a notification from the app which he felt compelled to check out right away.

It was a video that started out congratulating him with a positive evaluation. “Congratulations Trainee Luke on your stellar evaluation after only your first ever buddy workout. Mistress Olivia was extremely pleased with the results of your hard training you managed to show case. Keep this up and you might rise to the rang of Senior Trainee. Be warned however that while one great evaluation is something to proud of you will only rise in rank through continuous efforts. One victory isn’t nearly enough, the way to perfection is hard and constant work.”

This warning was quickly followed by more praise however, but it barely got through to Luke at this point as the hypnotic underlay was sending him straight into a deep trance once more. Instead of adding to his conditioning however the app first had him perform a truthful evaluation of Mistress Olivia and the whole experience under hypnosis. It mainly served as a way to verify the evaluation given by the actual users, to check whether or not they had stepped out of bound so the hypnotic conditioning could apply damage control if necessary. It was also a way to check whether or not the subject felt in an appropriate way about everything that had happened to see if corrections were needed.

Olivia had definitely pushed things a bit handing him a cup full of cum and letting go a little too much during the spanking. She hadn’t broken any of the rules given to her for the safe keeping of the project though meaning she could stay on board. If anything her pushing of boundaries had highlighted just how well the app worked as Luke recounted their work out with adjectives that hinted at excitement. The choice of words was really the only way to gauge his feelings as his tone remained flat and far away.

With the survey confirming Olivia’s story highlighting what a good time he had had with her and showing just how well and truly addicted Luke was to his protein shots, things couldn’t have gone any better. Nevertheless it were those things the hypnotic suggestions kept working on. After all hetero as he was getting him to accept a rather intimate massage like Olivia’s spanking might be easier than having him accept it from another guy. The goal from the app was to get Luke ready to serve each and every Master or Mistress provided by the app. He also didn’t know where his protein came from which might become a big of his hypnosis infused addiction to them. A break that could end up dragging all other suggestions down with it basically destroying all process. Slowly but surely the app would need to work on ensuring that wouldn’t happen.

“Working out is exhilarating, nothing goes above working out, but alone is just alone. Workouts are twice the fun with a partner, someone to keep you company, someone to guide you, someone who knows what they are talking about. Your workout partners are to be trusted above everything. Their knowledge is your guide. You love doing what they tell you to do, trying new things and new workouts you hadn’t even known existed. Just like they love showing you new things. The best way to repay their time and effort is by showing your eagerness to learn, to follow their instructions to the letter. Make sure your partner is pleased with your efforts above all else.” The hypnotic underlay played for him leaving the term partner ambiguous while prying Luke’s mind open to suggestions beyond what his mind connected or could make sense off from a workout perspective.

After giving that mantra several repeats it shifted to his protein shots. “Your protein shots are delicious, you love everything about them, out of all rewards and gifts the gift of protein is the one you like the best, even if you value every gift highly. You like this protein so much that you would love to know how it is made. If you could find the source of the protein you would cherish it beyond believe as it would give you a near infinite supply. Finding the source of your protein would be the best discovery ever.”

This praise for his “Protein shots” went on for over an hour. Highlighting the many benefits of finding the source for his protein. Benefits like the quantity he could get, or how much better it would be straight from the source. The hypnosis only highlighted benefits and positives about his protein. It wouldn’t really be able to fully prevent the shock when Luke would inevitably be shown how his protein came straight out of a man’s cock and balls. It was made to compensate for the shock, to make sure that when all was revealed his excitement over finding the source of his protein would be greater than the shock of discovering he had been fed cum.

Like that Luke’s afternoon carried on, in trance working on these two commands. One afternoon of listening to them wouldn’t really shift his believes or being. It would merely open his mind to be more accepting of getting pushed further and further by future workout buddies and to be ready once the source of his protein was inevitably revealed.