Caught in a New Life Pt.10 (Patreon)

Chapter 13

By the time Lena came back home Monroe was preparing lunch, a wok with plenty of vegetables and small pieces of beef as per Ms. Thompson’s instructions. She was just sitting at the table, a cleansing mud mask on her face that had completely dried by now. The cucumbers were off her eyes so she could watch him closely sitting in nothing but her bathrobe.

The difference between them both couldn’t be bigger, Ms. Thompson was completely relaxed while Monroe was just stressed and embarrassed. He wasn’t quite so sure that his wife would agree with his stance that more intimate massages were cheating. He certainly hoped so, but it seemed like she trusted Ms. Thompson completely, probably for a big part because she was starting to get a little more alienated towards him being gone so often.

“Mmm, Monroe that smells amazing. I trust the spa training is going very well judging from that facial mask Ms. Thompson?” Lena asked as she entered the kitchen. Monroe couldn’t even feel satisfied about her compliment, after all he had just been following orders, which had pretty much been his life lately.

“Oh yes Lena, it’s going very well, but we bumped on bit of a problem Monroe rightly claimed we should take up with you before we proceeded. I argued that given your goals for the little spa day I should teach him about some more intimate massages, the poor dear was worried that would equal cheating though, so before we proceed we would like to ask your opinion.” Ms. Thompson said as Monroe just carried on cooking with a bright blush.

“I understand the concern, but I think it’s okay. I trust you to make the best decision so I can have the best possible day tomorrow.” Lena said as Ms. Thompson smirked and Monroe looked horrified at her decision. Lena didn’t mind Ms. Thompson’s proposition simply because she was absolutely certain that her husband would never run off with Ms. Thompson, she was no threat in the slightest.

In fact he had probably only made a fuss because he didn’t want to touch her in more intimate places even without it being sexual, something which rekindled her initial anger at her husband. He was so shallow when it came to women, having demanded a pretty young girl from the maid service while she had ordered him to clean. Not even any available maid had been enough for him. Having him give Ms. Thompson a more intimate massage might prove to cure his shallowness and make him appreciate what he had.

Lunch proved to be very awkward for Monroe, sitting between these two eagerly chatting women who both seemed to be against him while he worried what his afternoon would bring. After lunch Lena just had a quick shower and decided to head out for the afternoon leaving Monroe back in Ms. Thompson’s care who promptly resumed the spa training.

It ended up being every bit as horrible as he had feared and more, he had to work his ass off to serve this old witch in often very intimate ways and she was very demanding of him. God he often shuddered over the places he had to massage and even kiss, but with the cheating argument off the table punishment and even more denial were his only options as Ms. Thompson would bend him to her will no matter how many shocks and spanks it took. After having had plenty examples the threat of it was pretty much enough for Monroe.

His afternoon ended when his wife came back home and Ms. Thompson left them alone after giving a good report. If he was good with his wife tomorrow he would finally get to cum. It had cost him a whole load of work and a big dent to his dignity however. After what Ms. Thompson had made him do massaging Lena’s feet and providing her with plenty of oral pleasure was pretty much heaven.

Exhausted Monroe finally ended up making it to the guestroom he shared with Ms. Thompson. He was in for a huge shock when Ms. Thompson was waiting on him completely naked, sitting on the edge of the bed with her legs spread and her greying hairy pussy on full display. He had seen plenty of naked Ms. Thompson that day, but never quite this explicit.

“Ah you’re here sissy, you did succeed to the criteria I set out to evaluate your spa training. You did manage to get me very wet, now I have a proposition for you. Given how your wife seems to enjoy your tongue so much I bet you are fantastic with it and I want to try it out for myself. So you either show me just what you can do with that tongue of yours and if you manage to make me cum I will plea with your wife to reward you with more frequent orgasms instead of once ever three days at most. If not well I guess then things will just stay the same.” Ms. Thompson said with a smirk.

Monroe was absolutely horrified, there was no way in hell that he would get any closer to that pussy than he already had today more frequent orgasms just weren’t worth it, especially not since he would get one tomorrow anyways. “I won’t do it, there’s just no way, I can’t.” He stammered.

“Well as you wish Monroe.” Ms. Thompson simply said, surprising him that she didn’t put more pressure on him to eat her out. She did end up horrifying him some more however when she didn’t close her legs but instead took a vibrator from nearby and started getting herself off. Horrified and not wanting any part of this Monroe got into bed and turned his back towards Ms. Thompson. There was no getting away from the loud buzzing of the vibrator, her moans or even the strong scent of her arousal filling the room, a scent he knew very well from smelling her panties whenever he did the laundry. She only stopped after three climaxes after which it was right to snoring, still loud, but at least not limiting his ability to fall asleep himself unlike those loud moans had been.

Chapter 14

The following morning the same embarrassing bathroom routine as always played out, only this time when Monroe saw Ms. Thompson upon waking up he couldn’t shake that horrid vision of her naked and pleasuring herself with her dildo last night. She also wasn’t dressed in her usual dresses, tights and heels, but rather in her workout clothes for some reason.

As they made their way to his closet Monroe’s worries grew. What would he find in there this time? He was dying for more clothes, but he had hated all the clothes Ms. Thompson had put in his closet so far, well the pantyhose were quite pleasant to the touch, too much so even, but Monroe disliked the fact that he got turned on by them.

When the closet opened, Monroe found his panties, pantyhose, his hobble skirts and now a pair of shoes, pumps to be exact. They only had a one inch block heel, yet they were decisively feminine made out of black lacquered leather. He was mortified, he couldn’t wear heels now could he? He knew protesting was futile and yet he had to, he couldn’t let this one pass. “Please Ms. Thompson I can’t wear heels. What if I twist an ankle and have to go to the hospital? I could end up with serious injuries.” Monroe complained.

“Nonsense sissy, you’ll do fine these heels are only barely twice as high as the heel on a man’s fancy dress shoe and they are only a little narrower, just walk the way I taught you yesterday and you’ll be more than fine.” Ms. Thompson said instantly destroying his argument, they didn’t look too hard to manage indeed, but they were heels, for a moment Monroe considered calling on Ms. Thompson’s rule that he could wear or not wear whatever he wanted from this closet, but he worried that would just mean she’d put even higher heels in next time, just like those original knee high socks had been exchanged for pantyhose when he didn’t wear them.

Learning to walk in even taller heels definitely wasn’t an option as he might really twist an ankle like that, besides he still needed to earn enough clothes to make it to the store fully dressed when they needed groceries. It was probably an idle hope, but he really hoped that if he behaved and just sucked this up he’d be at least given his male outer clothes for that occasion, if he could collect a full outfit that was.

Reluctantly Monroe got dressed in his panties, followed by carefully putting on a pair of sheer black pantyhose, another satin cream hobble underskirt and the black lacquered leather heels. He felt like a complete fool, but at lease if he neatly kept his elbows tucked at his sides to keep his balance stepping in these heels wasn’t all that hard. By now he was quite adapt to the outer limits his skirt allowed, taking quite natural small heel to toe steps.

Ms. Thompson smiled seeing how he walked, it was just perfect, a perfect sissy mince apart from the fact that his back wasn’t quite straight enough to her liking, but she could work on that. Having him rely on his held out arms for balance was perfect. If she could keep him off balance enough it was bound to become ingrained behaviour, just like the limits of his skirt seemed to be rather naturally incorporated in his walk by now.

“Much better sissy, now just so you can walk in your heels a bit and get the hang of them I think it’s time we headed for a work out just like yesterday. Your wife has requested to sleep in a little before starting her spa day so we have all the time in the world for now.” Ms. Thompson said with a grin as she guided him down to the gym where she once again set him up on the treadmill just like yesterday. A good long walk with a slight acceleration through out would definitely help him further ingrain his mince. The heels offering enough of a challenge to keep his elbows tucked at his sides. While the swishing of his smooth nylon legs once again turned him on. With so long since his last orgasm his cock was straining hard and leaking profusely in the tight cage.

After the workout Ms. Thompson took him into the kitchen where they shared a quick meagre breakfast before getting to work on Lena’s lavish one. Ms. Thompson also instructed him to make a pasta salad that he could just put in the refrigerator for lunch along with plenty of fancy snacks. She wanted to ensure the fridge was stocked so Monroe could dedicate all his time to serving his wife.

With a full tray of breakfast and a pat on his satin covered bottom Monroe was sent upstairs to his wife’s bedroom, the one they once shared to serve her breakfast on bed like every morning. Although he didn’t know it Ms. Thompson on her turn went to get a shower and put on her regular clothes once more, since Lena would be at home all day and since Monroe would be occupied serving her every whim there was nothing left here for her to do. Instead she looked forward to reporting on this successful project to Linda. She also had an appointment with Ben at his bar as he had seemed very interested in the sissification of Monroe.

Like every morning Monroe once again found himself between his wife’s legs as she enjoyed her breakfast, that’s were the routine stopped however. Throwing off the covers Lena looked down on his soaked face between her legs, loving the look of it. “Good morning honey. I can’t wait to see what you have learned, but first it’s time for me to shower, I believe you know this button don’t you? Well I’ll take a shower and I expect you to wait for me right outside the door.” Lena smirked showing him the button that could shock his balls, using the same trick Ms. Thompson used every morning. It caused Monroe to follow her closely as she got out of bed and headed into the bathroom.

Lena looked beautiful as she came out of the bathroom dressed in only a silky white bathrobe, and her hair wrapped up in a towel, the bathrobe showed a lot of cleavage and perfectly displayed her long slender legs making Monroe’s cock strain painfully once more. “So Monroe, I believe you know what to do now? Ms. Thompson told me that you had this whole day planned out and that all I needed to do was relax and enjoy myself. She told me she would quiz me once she got back.” Lena said with a smirk as she crossed her arms making her breasts appear even bigger.

“Uhm, yes I guess, uhm follow me please.” Monroe stammered, he hadn’t been explicitly informed about this supposedly having been planned, but he guessed he should just walk his wife through the steps Ms. Thompson had put him through the day before and in that order as well. He felt so silly standing there in his skirt and heels, but above all he was nervous, he needed to do a good job as Lena would decide whether or not he deserved an orgasm tonight, and his cock was definitely begging for it.

His wife’s smirk only grew bigger as she watch him get a mince on when he guided her downstairs. Ms. Thompson had clearly done a number on him, he even walked like a sissy. She thought to herself, oh she was so going to enjoy this day filled with pampering.

Just like yesterday Monroe started out by giving Lena a foot massage, followed by the pumice stone. Lena barely had any cuticle formation her feet already were very soft and well taken care off so a quick once over to remove what dead skin that was on her soles was more than enough. Unlike the demoded deep red old lady colour stuck on his toes Lena opted for a fresh crisp looking white. It still asked a lot of Monroe’s concentration, but he was quite well adapt to painting nails by now. That paired with the application of the face mask and the massage that came with it was pretty much the lamest part of the day.

While the mask did it’s work Monroe quickly set the table for two, put the salad he had prepared earlier on the designated plates, and poured two glasses of wine before moving back to his wife’s side. “Lena, your lunch is ready, if it pleases you, you may follow me to the table.” He nervously spoke as Lena just removed the cucumber from her eyes and followed along without a word. The day had started off wonderful and she was already feeling like a queen. Oh she could definitely get used to this.

Taking place at the table there finally was a sense of normality back in Monroe’s life. Finally he was able to share a meal with his wife again, in private without that horrible witch of a Ms. Thompson present. She might not be here, but her presence was definitely still felt. Afterall he was still stuck in that stupid skirt with that sheer hosiery that tantalised him with every move and his feet were starting to get sore from these heels forcing them into an unnatural angle despite them barely having any heel to speak of.

Not only that, but the relationship between him and his wife had definitely changed big time as well. She cast down one look at her plate, and then at his before saying. “Hmmm, why don’t you be quick about eating Monroe? I’m kind of craving an orgasm and I would like one before my meal is over.” Came the simple statement that despite it’s formulation was a pressing command. Monroe himself needed an orgasm way too much to even risk fucking up.

Lena slowly forked through her meal, eating a small bite at a time while Monroe rushed through his meal as fast as he could. For him there was no real enjoyment to what he had cooked. As after just five minutes he had managed to work his meal down leaving him enough time to pleasure his wife. She just smirked and opened her legs as he disappeared under the table, his skilful tongue instantly getting to work on her pussy, replacing the wonderful flavours of the meal with the taste of his wife’s pussy as she moaned high above him. It was a flavour he was slowly getting used to although he would be lying if he said he loved it.

With how slow Lena ate and how good Monroe had gotten with his tongue she ended up having two orgasms instead of just one by the time she finished her meal. Instead of telling her husband she was done Lena just shoved her chair back, pulling her pussy away from Monroe’s mouth. “So what’s next on the menu?” She simply asked smirking down on the wet faced Monroe who quickly crawled out from under the table.

“Uhm, oh well next it’s uhm time to move to the jacuzzi, p…please follow me.” Monroe said somewhat shook as he got up to his feet and started mincing upstairs to the Master bedroom where he quickly let the jacuzzi that doubled as bath fill. Using all kinds of fragrant oils and bath salts as per Ms. Thompson’s instructions. Yesterday they had used the outside jacuzzi for this without all the additives as Ms. Thompson didn’t want to invade Lena’s privacy

“If it pleases you, you may take place in the jacuzzi now.” Monroe nervously said, his jaw dropping as Lena casually dropped her bathrobe and stepped into the hot water. She had always been gorgeous, but with how horny he was having been locked up this long paired with how he had seen Ms. Thompson’s old body way more than his wife’s these past few days, Lena simply looked like a Goddess. He mourned the moment she put the jets on making it harder for him to see her as he started by washing off her face mask.

What followed was a scalp massage that slowly sank down to Lena’s shoulders, and finally down to her big firm breasts. It felt like heaven to be massaging his wife’s breasts, playing with her nipples. Yet he couldn’t fully enjoy it, it was making his cage very tight and uncomfortable for one, the other thing that really bothered him was how it brought back the awful memory of how he had needed to do the exact same thing for Ms. Thompson, massaging her saggy breasts and playing with her nipples under firm instructions how to do it as he had tried touching her as little as possible. Ms. Thompson had been very vocal about her enjoyment of this treatment to boot.

The jacuzzi treatment lasted for nearly two hours during which Monroe washed Lena’s hair, spending the rest of the time massaging, mainly focussing on her head, face, shoulders and breasts as the jets in the jacuzzi did the rest. Eventually it came to an end though as Monroe guided his wife out of the tub, once more getting a full appreciation of her gorgeous body as he dried her. “The next step of your spa day is the last one I have prepared Lena. I was told to tell you that if you are pleased and ready you may stop me at any time to unlock my cage, now could you please get comfortable on the bed? I’ll fetch some snacks and be right back up.” Monroe said, his face bright red as he suggested unlocking his cage basically as a sort of tip for working his ass off for his wife’s pleasure and relaxation all day long.

Today had really been one wonderful day as far as Lena was concerned. In fact she couldn’t remember ever having a day this good before, after all unlike at a real spa she could have Monroe between her legs whenever she felt the need. On top of being so relaxing this spa treatment was wonderfully tantalising to boot.

Although she wasn’t very aware of that change Lena had started to see her husband more and more as a servant through out the day. The more he had grovelled for her the less guilty she had started to feel about treating him this way. If anything he deserved it. She sure as hell wouldn’t want to miss this level of control, comfort and service anymore. Just like Ms. Thompson had intended, she wanted Lena to start viewing Monroe as just a servant she didn’t want to lose. By the time she left she wanted Monroe to be a complete sissy and his wife his Mistress that would ensure he stayed that way.

When Monroe made it back up the stairs with a platter filed with snacks he had prepared along with a bottle of champagne, his wife was already waiting on the bed, completely naked laying face down. Her ass looked so amazing from back where he was standing. He had always wanted to tap that ass, something Lena had never allowed him to do and he doubted she ever would after this. With how far this ridiculous thing was going he would be lucky if things could even go back to normal once he proved to his wife that this cage wasn’t necessary at all, that he could behave. Right now all he could think about was earning himself some relief though.

“Here you are Lena, snacks and refreshments are off to your right, feel free to enjoy them while I start with you massage.” Monroe nervously said as he placed the plate down next to Lena before moving to the foot of the bed where he first applied some oil then started massaging her feet, kneading his thumbs right into the soft pampered flesh. As his hands travelled up, his lips closely followed kissing the part he had just massaged it really made Lena feel like a Goddess, being worshipped like that.

Doing this for his wife was none too bad, but just like the Jacuzzi treatment, it made him shudder remembering how he had been forced to do this for Ms. Thompson as well. Kissing her way looser flesh and getting his hands all over her had been horrid, especially cause just like with Lena, he had been able to smell her arousal wafting up between her thighs when kissing her bottom. The only real difference arrived when he massaged Lena’s front.

With Ms. Thompson he had been allowed to kiss around her pussy although he had been required to come a lot closer to it than he liked. His wife on the other just grabbed his hair the moment he got close to her pussy and shoved his face right against her soaking wet lips. “Lick!” Was all she said as she grinned down keeping Monroe in place. Within seconds Monroe started licking like he was told, bringing his wife pleasure on demand with his tongue like he was getting used to by now. All that while remaining frustrated and locked up himself, hoping that his own relief would follow soon.

Lena had her husband lick her to three more orgasms before releasing his hair and letting him carry on with he wonderfully sensual massage while she slowly got down from her high. God this was great, all this personal attention, his tongue, but nevertheless she was looking forward to unlocking him. As great as his tongue was and as nice as it was to get better orgasms and more of them than ever before, she was kind of missing the feeling of something big filling her up. Last time she had let Monroe out of his cock cage it had been a huge disappointment. It had been a long time since she had been properly laid and she was craving it more than ever. Surely her husband wouldn’t let her down again right?

Eventually Lena ended up enjoying the massage for just short of another hour. Her body was well oiled up, slick and extremely soft to the touch as Monroe had carefully massaged and kissed every nook and cranny from her head down to her toes. It had gotten her worked up to the point where she could definitely use some relief once more and it was starting to get on the late side so now seemed like a good time to start what she hoped would be an hour long fuckfest to make up for lost time. She was completely relaxed and more than ready to get wild. “Alright Monroe, you may stop now, I think you’ve earned yourself some freedom. You know the deal, get down on your back, hands against the headboard.” Lena said with a big smirk as she too the cuffs out of the nightside table to restrain her husband just in case he wouldn’t want to put his cage back on.

Monroe would have liked to be able to fuck his wife instead of being tied down again, but he wasn’t about to complain. His need for release was so big that he couldn’t wait, within seconds he was down on his back, his hands held high above his head as his naked wife straddled his chest with a big smirk, locking his hands high above his head. “There we go, wouldn’t want you to get naughty now would we?” Lena teased as she got down to his crotch

The satin hobble skirt was still in the way as was the remainder of his outfit, but like a wild animal Lena made quick work of that. She pulled the skirt down to his ankles, ripped open the crotch of his pantyhose and shoved his panties to the side revealing the tight metal cage locked around his cock. A small moment of fumbling with he padlock later the cage came off and Monroe’s cock instantly grew into a full erection, already badly leaking precum as it was finally freed from its metal prison. His balls felt ready to burst as he had spent most of his day terribly turned on on top of his already aroused state. The feeling of his nylon legs rubbing together and against the slick satin of the skirt as well as spending all day in such close proximity to his gorgeous wife, touching her breasts, butt and every bit of her certain hadn’t missed it’s effect. He was exhausted after working his ass off all day, but at the same time he was thrilled and filled with anticipation as his wife slowly lowered herself onto his cock.

Her tight sopping wet pussy felt so stunningly good on his rock hard sensitive cock. Way too good even as he completely lost his composure. His cock started to twitch wildly within his wife as a mind numbing orgasm rolled through his body even before Lena had fully lowered herself onto his cock. All the pent up arousal and heaped up stimulation from throughout the day, paired with his exhaustion and the way Lena’s pussy felt like heaven compared to the hard unyielding metal had made it impossible to hold back. Something he didn’t even seem to care about as his eyes rolled back into his head from the sheer intensity of his orgasm. It was so powerful that he completely lost touch with what was going on around him, his head swimming in pure pleasure as he shot string after string of thick saved up cum up his wife’s pussy.

Straddling his cock Lena looked down on her blissful husband in sheer shock, she hadn’t even got started and he had came already. For a moment she tried to ride him as he was still hard, but all it did was prolong his orgasm and milk his balls completely dry as his cock started growing soft within ten bounces. It turned her shocked disappointment into frustration and eventually anger even. Linda and Ms. Thompson were right, Monroe only cared about getting his rocks off. He was a pathetic excuse for a man with a good for nothing cock. Well this was it, she was sure now that it belonged in a cage, no woman should have to deal with such disappointment and she surely wouldn’t put up with more than ever she was convinced that Monroe was a complete sissy, a thought that had grown through constantly grovelling, seeing him prance around in his skirt, heels and now this.

Linda, Ms. Thompson and even Ben’s pushing had moulded her mind to see Monroe as a pathetic excuse for a man and a sissy. Having been married to him for a few years she had always doubted that always rationalised that she knew that wasn’t the case, they had manged to make her doubt that conviction though, after last time’s premature ejaculation, her doubts in her husband had only grown, but with this spectacular disappointment, her sexual frustration over the complete failure of this moment she had been anticipating for a while, destroyed all rational thought at this moment. It convinced her that Linda, Ms. Thompson and Ben had always been right. She was angry, angry at herself for never seeing it and angry ad Monroe for leaving her hanging like this.

“You fucking bastard, do you call that a fucking cock? That’s just a fucking trigger if you ask me, I would call you a two pump chump, but at this point that would be a fucking compliment as you don’t even last half as long! Well I’m not going to be left hanging, clearly that cock of yours is useless, but at least you’ve learned to use your fucking tongue!” Lena screamed shocking Monroe out of his blissful daze as she stepped off of his by now limp cock, moving right up for his face, his thick cum dripping out of her pussy all over his torso on the way up.

Before Monroe well and truly grasped what was happening Lena had sat her cum oozing pussy down on his face, turning around so she was facing his cock and his nose was pressing against her butthole. His first instinct was too scream, but that only got him a mouth full of his own cum that dripped out of his wife’s pussy as he recoiled and gagged in horror over the salty bitter flavour mixed with just a subtle tangy taste of his wife’s juices. He was going to feel sick as he struggled in his cuffs pinned underneath his wife’s pussy while she made quick work out of locking his limp cock back up in the cage.

His sheer disgust over his first taste of cum had Monroe seal his lips shut, but it only further enraged his wife. “What the hell are you waiting for you fucking asshole? Are you going to start licking or what? Prove that you aren’t completely worthless. Fucking hell I might as well go flush this key down the toilet you fucking sissy. Is it because of your fucking cum? Well deal with it, you make a mess you clean that mess up and I don’t fucking care if you don’t like it. I didn’t like to be pumped full of cum either, I wanted to fuck, now get licking and clean up your fucking mess.” Lena screamed on top of Monroe.

Hearing how angry his wife was and fearing that she might actually do something stupid if he started licking just so she would stay on his face. He wanted nothing more than to get her cum filled pussy away from his mouth, but considering how mad she was he really didn’t want her to get too far away with him tied up and unable to stop her whatever she would do. With his arousal gone, and the cum making a task he had only recently come to fully accept into something hard and disgusting, Monroe had his work cut out for him. He could swear that he was going to be sick as more and more of his cum made it into his mouth and eventually into his stomach, but at least Lena’s extremely embarrassing hurtful angry insults turned to moans.

By the time Lena finally got off of his face, he was sure that he had swallowed the entirety of his load as after her second orgasm the taste off cum had pretty much disappeared. It made him feel nauseous. At least Lena seemed to have calmed down though, her frustration gone for the most part after multiple orgasms, yet she remained disappointed as she just quickly unlocked his cuffs and coldly said. “Get out right now.”

It was a tone that terrified Monroe, especially after what had just happened. Scrambling to pull his skirt back up Monroe hurried out of the room as fast as he could. Specs of dried up cum were stuck to his stomach and a mixture of his cum and Lena’s juices still coated his face. The last thing he wanted was to stay around his wife right now. Although, when he made it to the spare room and he saw the horrid Ms. Thompson already in bed reading a book he wasn’t so sure anymore. She must have come home at some point when they were up in the master bedroom. “I hope your wife wasn’t mad because you screwed up your spa treatment. Don’t bother answering, I’ll ask her tomorrow.” Ms. Thompson said putting her book away and turning off the light before going to sleep.

Monroe was left trying to feel his way to the bed, not daring to go wash up afraid he would somehow anger Ms. Thompson. Kicking off his heels was pretty much all he managed to before getting into bed himself. His mind was racing and he was filled with worries after what had happened. It wasn’t his fault he tried to convince himself before after hours of over thinking he too went to drifted off to sleep.