Caught in a New Life Pt. 11

Chapter 15

Just like every morning Monroe woke up with a loud groan as the alarm went off. The taste of cum and pussy in his mouth served as a firm reminder of how horrible last night had been. It had started out as the night he had looked forward to so much, the night he could finally prove himself again after being treated like a sissy for so long that he actually started feeling like he was a sissy instead of a man. Instead of proving himself however he had only further proven that everyone might be right and he might just be a sissy. Hell he couldn't even please his wife with his cock anymore. The only thing that was good at pleasing pussy was his tongue, he was literally pussy-whipped.

Hell he couldn't even decide what hurt his ego the most, the fact that he had basically swallowed a load of cum, or the fact that his cock was pretty much useless. Either way last night had been devastating, but he didn't have a lot of time to marinate in his sorrows as Ms. Thompson just got up and headed into the bathroom. She didn't bother waking him up explicitly this time or even waiting for him. Nevertheless Monroe quickly rose nearly tripping due to his hobble skirt as he rushed to stand guard at the door of the bathroom afraid he would get a shock if he didn't.

Although he didn't like the scent of Ms. Thompson's soaps and shampoo's in the slightest he looked forward to using the bathroom now more than ever. It was the only way he would get rid of the strong smell and taste of cum and pussy all over him. In preparation to get cleaned up Monroe stripped out of the skirt and pantyhose he had still been wearing. They looked awfully lewd with the crotch torn open like that.

The wait for the bathroom seemed to take forever and when the door finally opened Monroe visibly cringed, standing there wearing nothing but his chastity cage. Ms. Thompson smelling strongly of lavender like he soon would emerged wearing nothing but a towel in her hair and one around her chest. She was clearly eyeing him up and down before smirking. "Had a fun night pansy? Looks like there's still some pie left around your mouth, some cream pie." She mocked with a loud laugh before removing the key from the inside of the door and signalling Monroe to go in.

Was it so obvious what had happened last night? He thought as he quickly dashed into the bathroom only to get the door slammed shut and locked from the outside behind him. One look in the mirror told him all he needed to know, next to the taste and smell it was rather obvious that something had crusted around his mouth and on his face. He couldn't believe he had just given Ms. Thompson more firepower to embarrass him as he quickly turned on the shower and stepped in to wash all evidence off of his body.

While he was hurrying to get clean and get rid of all of last night's evidence Monroe didn't realise that Ms. Thompson was having a talk with his wife. She had been up way earlier than usual and just like Monroe she hadn't forgotten about last night either. She was still somewhat pissed and frustrated, enough so to remember one of Ms. Thompson's suggestions to relieve her of needing to take care of Monroe's sexual urges if it became a bother to her. She had been against it at first, but constantly hearing from Ben, Linda and Ms. Thompson how useless Monroe was along with the sorely disappointing performances two time in a row had convinced her.

"Look Ms. Thompson, I am very sorry to call you in here so early and I am very sorry to involve you in this, but I just can't do it anymore. I don't want to reward my husband if his behaviour is abysmal, but I can't get hyped up for multiple days only to end up with another grave disappointment like yesterday or the time before. Hell he didn't even last a full stroke this time. While his tongue did end up making up for some of the disappointment it just isn't the same and I fear that next time it will just be disappointing all over as well. I don't want to get excited only to be disappointed again." Lena explained as Ms. Thompson made her way into the master bedroom.

"I know it's a lot to ask given the rather intimate nature off this request and I know you aren't a sex worker and this isn't why I hired you, but you proposed to take care of his urges once before and I hope that offer still stands. Would you please take care of his release in the future? I can take over again once he can last more than a minute, hell with how frustrated I am I bet that is all I would need right now, just a good fuck for more than a minute." Lena continued her rant. It felt so weird to ask another woman to take care of her husband's needs

"Oh no, it isn't a problem at all, of course I will help you Lena. You shouldn't have to put up with that at all. Your sissy husband shouldn't expect to get his rocks off when he can't help you get off. It is completely selfish and one of his core problems, even know all he is thinking about is himself. In fact I am happy you tasked me with this as it'll allow me to work more effectively. I will most certainly let you know when he can last over a minute once more, until that time why don't you give me your spare of his chastity key? I believe it would only serve as a painful reminder." Ms. Thompson said empathically, trying her best not to smile.

All her efforts were bearing fruits now. Without sex even if it was frustrating sex Lena would only get alienated further from seeing Monroe as her husband, leaning more and more to seeing him as her sissy maid. She would ensure that he never reached that one minute goal set out by her, in fact she planned to work on making his premature ejaculation problem due to pent up arousal even worse. Of course neither of them had to know about that, just like they probably didn't know that yesterday was the last time Monroe had put his dick in his wife. She kind of wanted to put Lena on her way to open up to trying to find some boyfriends who could satisfy her and sate that itch she had, but this decision couldn't have been a light one for her so she thought it wise not to push Lena any further right now.

"Thank you Ms. Thompson you are the best, what would I do without you? I guess you are right I won't be needing this anymore for now. Oh and by the way, I won't be needing breakfast, lunch or dinner. I don't want to see him today, can you do me another favour and be the one to break it to him? I think it'll be best that I won't be around for that. Now if you'll excuse me, I'll be getting ready now." Lena said with a sigh of relief as she handed the small chastity key to Ms. Thompson. She couldn't even unlock Monroe's cock if she wanted to now.

"Of course Lena, have a nice day, I'll be keeping him in the guestroom until I hear you leaving so you won't have to see him. Also if you still don't want to see him tonight just text me when you plan to come home and I'll ensure that he's in bed by that time." Ms. Thompson said before leaving the room and returning to hers where she still heard the shower running. Oh she couldn't wait to break her new power over him to Monroe, he didn't even realise how doomed he was yet.

It took nearly ten more minutes before Monroe ended up making it out of the shower, his completely smooth body smelling strongly of lavender. His towel was neatly tucked around his chest just like Ms. Thompson had shown him before. He didn't like smelling like lavender one bit, but at least this morning it was a welcome relief from the cum smell that had hung around him all night. The was Ms. Thompson was smirking at him broader than he remembered was highly unsettling, but then again he could just be imagining things.

By now Ms. Thompson had heard Lena leave so it was safe to take Monroe out to his closet. "Follow me sissy." She simply said as she turned on her heel and walked him to the other guest bedroom. With a loud groan Monroe just followed, he knew making a fuss was pretty much useless so he didn't even try. If anything his failure yesterday had only made him meeker.

On the way there Ms. Thompson was very pleased to notice how Monroe's steps were already significantly smaller than they had once been. There was also a defined wiggle in his step even though he wasn't wearing his hobble skirt or heels. He even held his arms out slightly more than the usual relaxed position they had always been in. The best thing probably was that he didn't even realised how much his gait was changing with how restricted it was nearly all of the time.

Once arrived in the guest room Monroe didn't need to be told what to do. It was slowly starting to become routine. Opening up the closet by now cause him more dread than hope. He had long since given up hope that he would get any of his male clothes back, even when it came to outerwear. It was once again confirmed when in his new piece of clothing turned out to be a corset. There were two of them, one in white satin, and one in black satin, both had a relatively simple design with hard cups to support breasts he didn't have. Like most of his clothes for now they weren't designed to look amazing, but rather to do a job. The corset's job would be to train his waist and keep his back straight at all times to further improve his posture.

"Alright pansy, now this is a little tricky, I doubt you can sufficiently tie and tighten it yourself as the laces go behind your back so if you need help just ask. Know that there are only two more days left until we'll have to go out for groceries. After this you basically only need a top leaving room for you to potentially get an accessory I bet will be more than welcome on the day we go out. So what is it going to be? Are you going to ask for my help or lose the last chance at a useful accessory while I look from some upper body lingerie you might like." Ms. Thompson asked with a smirk applying some pressure as she saw the doubt on Monroe's face.

An accessory what was that supposed to mean? Did he really want to wear more than what he absolutely had to? The fact that Ms. Thompson called it a welcome one didn't help him one bit, would it be welcome for him, or for her to make him look even more ridiculous? On top of that he also really didn't want to wear the corset but what would he get in its stead? Would it be worse, could it be worse? In any case it was picking this corset or waiting to see what Ms. Thompson got for him tomorrow, he really needed a top so he couldn't postpone it any further.

Eventually Monroe decided he would just do it, it was the safest bet since he could always deny the accessory if he didn't like it. At least he guessed so. Without further ado he started getting dressed. He put on the white panties, a pair of glossy black sheer pantyhose, another hobble underskirt, this one in shimmering black satin, the heels were the same as yesterday, or at least they looked that way. Monroe could swear that they were slightly taller than yesterday's heels though, not by enough to tell without comparing them, yet noticeable when wearing them.

Last but not least he fished the black corset out of the closet and wrapped it around his torso. The material just like everything he wore felt quite pleasant, quite slippery, yet it also felt very stiff. Turning his back to Ms. Thompson he spoke up, hating himself for it, but he had to do this. "Please Nanny could you tie my corset for me." He asked softly.

"Of course pansy, with pleasure even." Ms. Thompson spoke satisfied that he was bending to her will. Stepping in behind him she put a knee in the small of his back and with a surprising strength for a woman her age she tightened the laces of the corset, knocking the air out of Monroe's lungs before tying it off.

"Now off to make breakfast you go." She smirked sending him on his way with a pat on his bottom. The corset really did wonders for his figure. It pushed some flesh into the stiff cups creating the illusion of budding breasts while taking his waste in a couple of inches giving his body a feminine curve to it. Not only that, she was also pleased to see how the half an inch taller paired with the fact that his torso was forced up right caused him to stick his arms out for balance in the dainty fashion she had taught him once more further ingraining the sissy mince he was already progressing towards.

Walking was becoming an utter nightmare for Monroe, with every step he was afraid he would trip. The extremely tight corset prevented any slouching at all. Not only that, but it made him short of breath as well. With how it contracted his waist and ribs all he could do was take shallow breaths. His outfit was clearly getting further and further out of hand, but with Ms. Thompson on his case and ready to punish 24/7 he had little choices but to go along with it.

Making it into the kitchen after his unnerving walk Monroe started taking out everything he needed to prepare his wife's breakfast, something that was slowly growing into a routine by now. He couldn't help but shudder thinking about meeting his wife back in the master bedroom for breakfast after what had happened last night. Thinking back to it he could still taste his own cum even though it had to be an illusion at this point.

"You can put that tray away pansy, you won't be serving your wife breakfast this morning. In fact it's just you and me for probably the remainder of the day. She's sick and tired of your selfishness, your cock going off before you even give her any pleasure. Yes she told me all about your lacklustre performance. She told me that she couldn't handle having sex with you again if it would just end in grave disappointment so she asked me if I could take care of that for the time being." Ms. Thompson explained with a big smirk as she put the keys to his cage on the table to show evidence of this power she now wielded, to show Monroe that she wasn't kidding, that his wife had really entrusted his cock to this horrid woman.

Ms. Thompson loved the shocked look on Monroe's face, a look that grew more and more shocked as she doubled down on her explanation. "She asked me to help you build up some stamina again so you might be able to satisfy her with more than your tongue again. I was told not to even bother giving that key back to her until you could last at least five full minutes. Until that time I guess I get to be judge and jury of how well you are doing and when you deserve some relief. Your wife doesn't want to be bothered by such things for the time being so you better keep that in mind when following my orders and guidelines."

In Ms. Thompson's mind Lena had been way too soft on Monroe, requiring him to only last a minute, luckily the sissy didn't know that allowing her to impose her five minute rule. With how Monroe wasn't attracted to her in the slightest, she guessed he might very well make a minute, but there was no way he was going to make five, in fact she would work on him until there was no way he could last at all. Under the guise of helping him build stamina she would make sure that it crumbled further to the point where a direct touch wasn't even necessary.

"Don't worry though Pansy, I don't like having to take care of that nasty premature ejaculating clit of yours anymore than you do, so I'll do anything in my power to help you work up to that five minute mark. I trust I'll have your full cooperation with that or I'm afraid you'll never stick that dick in your wife's pussy again." Ms. Thompson carried on upping the pressure to comply with her.

When she saw that Monroe was about to protest she quickly intervened once more. "I'm a reasonable woman though Pansy, if you're on your best behaviour you can even expect to get to cum on a daily basis. Like I said the sooner we can get this over with the better for both of us. I absolutely can't and won't tolerate bad behaviour though, so if you mess up I can't reward you with an orgasm now can I?" Ms. Thompson asked. She didn't mind unlocking him daily as her plans for him were so much greater than just leaving him frustrated, the more she took his cock out to play the more progress she could make, it wasn't even a compromise although Monroe probably wasn't aware of that.

Monroe was trying his hardest to bite his tongue. This was utterly ridiculous and he couldn't condone this shit at all. He couldn't believe how his wife had broadcasted his performance issues too this bitch, and even less how she was now in charge of his orgasms. He should not accept this, but at the same time he realised full well that there was no way in which he would be able to change the mind of this hateful bitch of a Ms. Thompson. If he wanted to stop this he had to take this up with his wife so right now his best shot was to just stay quiet.

The thought of doing anything of a sexual nature with Ms. Thompson was more than enough to make him shudder. While he would love to have daily orgasms again, or better yet to get rid of that hated cage entirely there was simply no way in which he was doing this with Ms. Thompson. Hell eating his cum out of Lena's pussy was more preferable than getting intimate with this old witch. Lasting longer in the bedroom was something he desperately wanted as well, but not with Ms. Thompson's help.

She might claim to be a reasonable woman, but if Monroe had learned anything it was that she was anything but reasonable. Lena was the only one to be reasoned with on some level and since she wasn't here he'd better do as Ms. Thompson demanded or paid the prize. It was another thing he had learned about her, standing up against this hated woman always had a prize, it had never been worth it before. He just hoped that he would be able to sway Lena, something which had sadly become harder and harder as well.

Seeing his acceptance for now Ms. Thompson nodded approvingly. "Great, I see we understand one another, now get started on our breakfast and remember, behave and we'll get along just fine. You'll get your orgasm, I'll help you grow your stamina and we can both get out of this." Ms. Thompson reassured as she leaned back with a self-satisfied smile, happy that she had quelled his protests without needing to use force. It was a big leap forward to moulding him into the perfectly obedient sissy maid she was sent here to create.

Meanwhile Monroe told himself that nothing in the greater scheme of things had happened yet. With his wife in control of the key he would have had to wait at least three days until his next orgasm anyways. Sure he would rather have her unlock him on a daily basis, something Ms. Thompson did offer, but he'd rather cum once every three days inside of his wife than every day with Ms. Thompson. As long as he managed to convince his wife to just take his key back from that witch in the next three days there was nothing lost, not really at least, the fact that she had given it up in the first place stung either way.

Sighing deeply as he tried to console himself Monroe got started making their breakfast like he usually did. Apart from this big revelation and the fact that he didn't have to serve his wife, his day was pretty much the same as it had been for a while now. He made breakfast, served him and Ms. Thompson as they pretty much ate in silence then went upstairs to tidy up the rooms and handwash all laundry he found. Doing laundry remained a nasty task, especially Ms. Thompson's laundry as he was still forced to give each and every item a sniff.

When he washed his wife's bathrobe, the only thing she had worn yesterday he couldn't help but groan thinking back to wonderful day they had. Sure he hadn't liked the extensive spa treatment as it made him feel so submissive, but aside from that it was some quality time with his wife which was way better than just doing chores. He seemed to remember how she had been more aroused than usual yesterday. At least when he had eaten her out she had been wetter than usual. It told him that just like him she had looked forward to their sexy time yesterday making him painfully aware of just how disappointing his performance must have been.