Caught in a New Life

Chapter 22

Ms. Thompson was casually propped up against the headboard of the bed, reading a book when Molly finally minced his way into the room looking completely defeated, and hopeless, more so than usual. It didn't take her long to realise that something drastic must have happened while she had left the husband and wife alone. While she didn't know for certain she could make a solid guess that Lena must have made it very clear to Molly that there wouldn't be any going back to normal. After all it was the direction she had bee pushing Lena into, convincing her that Molly was better off as a sissy. It was the most logical explanation, and while it was a major victory for her plan to keep Molly in panties permanently by the time she was done here, it was also a major complication.

She had hoped that she would have been a little further along the path of truly breaking Molly's spirits. After all next to her very stern supervision and punishments, the thought that things might return to normal was the best motivation to keep her sissy project docile and obedient. Now that that was ripped away she feared some real heavy protests no matter the cost might ensue. After all there was nothing left to lose, if this was permanent Molly had to know her acquaintances would find out about her sissy life sooner or later.

In any case what was done was done. Her top priority right now was to ensure Molly once again had a lot to lose. That she would see that being Lena's sissy was the best she could hope for in life. She had to ensure Molly would feel the dire need to be the best sissy she could possibly be for her wife and to accomplish that some radical action was needed. Action she had shied away from until now as it would have been too much for Molly to take which would have resulted in a heavy protest no matter the cost before. She could only hope that she had show Molly that she could make her threats happen for the sissy to be scared in obedience forever. In any case now when she was at her most vulnerable still mourning rather than thinking about a real big protest was her best bet to squash his resistance.

"Ah Molly there you are, great something I really wanted to discus with you just came up. You see given how naturally you take to being a sissy and how you constantly refuse my attempt to train your endurance so you can reinvigorate your sex life with your wife, I've come to question whether you are actually gay? I mean if you are not at all interested in learning to please a woman, pleasing a man might be more of your style. Besides with lips like those I'm certain you can please about any man out there." Ms. Thompson spoke giving Molly some time to process what she had just said, the horror struck face telling her the sissy had processed it.

"Obviously moving back to your old deceptive ways is out of the question, but if you aren't willing to be the best sissy husband you can be for your wife I think Lena will agree that a divorce is best and luckily I have a friend who is more than willing to take on a sissy house wife. He's a bit strict and a bit older than you are, but I'm certain he'll take excellent care of all your sissy needs. I mean if you weren't motivated to be the best version of yourself for your wife I think it would be best for everyone involved, I would be free to move on, your wife would be free to find someone who did care enough to give her their all like she deserves and your new husband would surely be very happy. Of course you'll also get to live your best sissy life." Ms. Thompson continued calmly as Monroe's horror only grew.

Monroe's head was spinning as he thought about what Ms. Thompson just said. He didn't want to be a sissy, not at all, but Lena had made it very clear there would be no turning back, all thanks to Ms. Thompson's manipulations. He was terrified that Lena would actually agree to give him over to whoever the fuck that old guy Ms. Thompson spoke about was. One thing was for certain though, he wanted nothing to do with another guy and certainly not some old guy wanting to make him his sissy wife, the thought alone made him shudder in disgust more than he ever had before. It was certainly a fate that was to be avoided at all costs.

The worst thing of all was that he feared like Ms. Thompson could actually easily do everything she just said down to the divorce. Given how she had been able to punish him, a man even an older one than him would have a way easier time keeping him in check. If she called him over he would be helpless and Lena could easily claim that his perverted ways and even more incriminating his relationship with a man no less was too much for her to take which is why she would file for divorce. No matter what he said, there was plenty of evidence stacked against him and all the people he had actually interacted with at Ben's bar, the salon and of course Ms. Thompson herself would probably be more than happy to testify against him.

He was screwed beyond believe, about to beg her not to do this when Ms. Thompson simply put her book down, threw off the covers, sat up on the edge of her bed, hiked up her nightdress and opened her legs wide revealing her old hairy pussy. "So Molly would you like to pay your fee for the start of your endurance training, an orgasm for an orgasm, or aren't you interested in growing into a better sissy for your wife?" She simply asked, a slight smirk tugging at a corner of her mouth as she could already guess the answer.

Despite his arousal having gone without an orgasm for so very long Monroe was not at all planning to give in to this horrible demand yet. He didn't want to eat the unshaved pussy of an older woman, let alone let her touch his cock after it. Yet as much as he wanted to say no, he was terrified of the potential consequences, they were too horrible to even want to consider. All he could really do was do whatever was in his power to become the best possible version of his new self for his wife in the hope that she would be willing to keep him around rather than send him off to whoever Ms. Thompson had in mind.

Horrified and utterly disgusted Monroe minced over to the most horrid woman he had ever met only to sink down to his nylon clad knees in front of her. The stench of Ms. Thompson's arousal mixed with the scent of her sweat from the busy day they had had was utterly horrifying. At least his training with her panties everyday, allowed him to supress his gags as he slowly but surely leaned in, sticking his tongue between those wiry hairs only to find Ms. Thompson's warm wet folds was disgusting, the taste and feel so much worse than he had imagined it. He had never liked eating pussy, but eating Lena's pussy was fine dining compared to this. His reluctance and disgust translated very much into his actions as he stayed as far removed from Ms. Thompson's pussy as he possibly could while flicking her outer lips with the very tip of his tongue.

"That is utterly pathetic Molly, I can see why your wife kicked you out of the bedroom for me to train you, there is no way that is pleasing any woman. It feels like you are disgusted by a pussy while it should feel like a pussy is the best thing you ever tasted in your whole life. That is unless you are gay of course in which case I would totally understand your reluctance. In that case you can stop and I'll make the call right away." Ms. Thompson said with a smirk, loving that she had Molly right where she wanted.

For Monroe just the thought of her calling on her friend was enough to conquer his reluctance. As horrible as eating this horrid old woman's pussy was, it would be so much better than getting anywhere near the guy she had mentioned. Reluctantly Monroe pressed his whole face into Ms. Thompson's bushy pussy, wiggling his tongue as deep as it could go, doing everything in his power to make her cum as fast as he possibly could. He took Ms. Thompson's advise to heart, not shying away from anything as he continued to eat her pussy, trying not to gag as he could hear some loud moans coming from above him.

"Mmm, maybe I was wrong about your sexual orientation after all Molly, that feels down right amazing, whatever you do, don't you dare slack sissy!" Ms. Thompson moaned from above as Monroe reluctantly carried on. His only saving grace was the fact that he actually managed to make Ms. Thompson orgasm in only a little over five minutes. Just like him she had quite a bit of pent up arousal resulting from how much turning a man into a sissy turned her on as well as Monroe's constant rejections to eat her out night after night. Watching him 24/7 was no easy feat giving her little privacy as well, not that she restrained herself much when around her sissy project, but still. That was all ending now though as she gushed out an intense orgasm all over his made up face.

"There we go, so much better sissy, at this rate you might actually start making a proper sissy for your wife and save your marriage. Too bad I'll have to disappoint my friend and tell him you're no longer available. I just know he would have loved trying out each and every one of your holes. In any case you can pull back now Molly. Let's get you ready for the night first and then go over to your endurance practice shall we? Get up and follow me into the bathroom." Ms. Thompson spoke sternly as she herself got up from the bed, just letting her night dress drop back down.

Monroe himself was more than happy to follow through, hoping he would be allowed to get rid of the woman's horrid smelling pussy juices plastered all over his heavily made up face. He couldn't help but shudder as he was escorted to the mirror, once again confronted by just how horribly feminine he looked. The water proof makeup Suzan had used earlier in the day worked wonders as his heavily made up look remained pretty much intact despite the thick coating of juices plastered all over his face. Even his new obnoxious hair had remained stiffly in place.

"Now Molly since you've gotten yourself such a fancy look the time of just sliding in your bed is over, this look is pretty high in up keep, but don't worry, I'll teach you all you need to know about it." Ms. Thompson smirked as she went ahead with her instructions. At first Monroe was relieved that he got to clean his face off of her pussy juices and that horrid makeup, but that didn't last long with his thin arched eyebrows his face remained rather feminine looking, especially under that hair. The green goop he was then forced to apply to his face wasn't any better for his ego, and as horrid as the hairstyle was he couldn't help but think it was even worse when she made him brush out his hair and put it in tight bristle rollers, all protected with a white satin cap that had a trim of bright pink lace surrounding it. He couldn't help but feel like even more of an outdated stereotype like this.

With help from Ms. Thompson Monroe was then helped out of his dress and his corset, left to take care of the rest of his outfit himself. He was more than happy that that intense pressure on his waist had finally eased up, but not nearly as happy as he was when he got to step out of those horrid heels he had been wearing all day, the heels that had quickly become the worst and most uncomfortable part of his entire outfit. It was a pure blessing to be relieved of that all despite knowing he would have to return to wearing them tomorrow most likely.

Fully naked Ms. Thompson taught him how to run a bath, telling him that was what he was going to take from now on in order not to wet his hair which would be taken care of at the salon for him. The oils, bath salts and bath bomb he was made to add to the water were all lavender scented, just like the products she had made him use before. It wouldn't make much of a difference for Monroe aside from the fact that he would need to take way longer to get red, required to spend a minimum of thirty minutes in the bath each morning and night.

Ms. Thompson's next instruction however brought forth a big horrid change for Monroe. With great delight she produced a big pink rubber bag with a hose and a thin hot pink nozzle attached to it. "Since you are now aiming to get sexually active again, even if it has just been oral so far, I think it's about time you learned about proper sissy sexual hygiene and especially its most important tool the douche Molly." She grinned big time as she filled the big rubber bag with water only to drop in a few drops of lavender soap before hanging it up on the shower rod.

"You can get this over with in any position you like Molly, but right here and now I'm feeling a face down ass up position is most suitable, so get to it Molly get in position." Ms. Thompson spoke, very eager to take the honours for Monroe's first ever enema, and what she guessed the first ever time someone put anything up his ass before. She always loved the moment when she could introduce a previously straight tough guy to anal as it was often more embarrassing than any dress she could put them into.

"Wait, no please Nanny, not that I beg you, it's completely unnecessary. I mean that's never going to be used for anything sexual right? I'm happy just sticking with oral I swear." Monroe pleaded nervously, trying hard to maintain his feminine voice as well as he possibly could, anything to avoid that horrid hag from going anywhere near his bottom with that nozzle. He couldn't believe he even had to defend his ass, but that was the sad state all of this had led to, he could only hope that Ms. Thompson would finally yield on something, but he knew he shouldn't cherish too much hope for that. He had a bad feeling he knew where this was going, but absolutely exhausted and defeated, a plea was about all the protest he could manage.

"Absolutely not Molly, it isn't even about whether it'll be used for sex or not, but cleanliness is very important when it comes to sexual intercourse and having you squeaky clean inside and out will be a good reminder of that. Now get in position or do I need to give you a spanking?" Ms. Thompson sternly asked as she fixed Monroe with a glare. She had to admit it, after the exhausting day she had put him through she was surprised that he was still able to put up this meek defiance, but she was going to make sure it wasn't long for the world.

Monroe felt devastated, he badly wanted to fight this, he didn't want to give up his ass so easily, but he knew this discussion would only end one way. On top of that he really didn't want to take a spanking, not again. His bottom was still sore from the one he had gotten in Ben's club. Still his reluctance was big enough to hesitate, hesitate until he saw Ms. Thompson lift her hand and approach him, ready to dish out a slap. In a moment of panic he simply dropped to his knees, then stuck his bottom high up in the air in complete and utter defeat.

"There we go, that's so much better Molly." Ms. Thompson spoke with a big smile as she moved behind Monroe, savouring another victory over Monroe. She really loved her job. Not delaying the inevitable any more she pressed the lubed up tip of the nozzle up against Monroe's butthole, it was too thin to give the sissy much discomfort, but she simply knew that having something up his ass would be a severe mental blow, another one that was, as his day had consisted out of nothing but heavy mental blows, one lined up after the other.

For a brief moment she paused right there, savouring Monroe's whimpers as he tried bracing himself for what was coming, the tip gently pressing against his puckered hole without pushing in yet. Something that soon changed however when Ms. Thompson applied just a little pressure. Monroe's hole was no match to resist the thin well lubed tip as it slid right in as he let out a loud yelp followed by numerous groans as inch after inch entered his virgin bottom until it was all the way in. It didn't hurt, but it was very uncomfortable, not in the slightest because it was a feeling that was completely alien to him, something relatively long and hard entering his bottom like that, moving around with every slight movement of Ms. Thompson's hand.

Much to Monroe's horror Ms. Thompson didn't keep the nozzle still either, instead she stared slowly moving it in and out, fucking his ass with it. He wanted to bitterly complain about it, but he knew that she would keep the nozzle in his head for the entire length of the discussion if he did. Having given in so far, fighting now was completely pointless, all he could hope was that it would be over soon, not realising what exactly Ms. Thompson was doing.

She had milked many sissies before, and was quite skilled at it. By now Monroe was overly aroused, frustrated and in dire need of an orgasm, the perfect mix to make his prostate very receptive to some probing as she skilfully worked the nozzle back and forth over the sensitive gland. If she wanted she would easily be able to make him cum right here and now, but that wasn't what she was aiming for not yet at least, all she wanted now was to move him to the very edge of an orgasm and as the first moans started to come in she was more than pleased.

Monroe was absolutely mortified, for as uncomfortable and alien as it felt the nozzle also gave him a very strange pleasant sensation unlike any he had ever felt before. It was so pleasant in fact that he couldn't supress a moan much to his own horror. How could it be that he was enjoying getting his ass penetrated by a nozzle? If anything it was more mortifying that the outfit or the makeover he had gotten, how could he cling onto what he saw as his masculinity if he literally enjoyed getting penetrated. It only got worse as well as he could actually feel a weird kind of orgasm approaching, fearing that all it took was a few more rubs over a strangely sensitive spot. Just before he was there however the water from the bag started flooding deep into his bottom, creating an uncomfortable pressure that soon turned to cramps as it kept on going. It was just horrible enough to keep him just out of reach of his orgasm, yet as the nozzle continued to penetrating he was still kept on edge, reduced to a series of loud moans and groans as embarrassing pleasure and horrible discomfort mixed.

This was kept up for the entire five minutes it took for the bag to empty at which point even Ms. Thompson's skilled efforts were failing to keep him on edge as the cramps were growing to severe. "Alright Molly, be sure to clench those butt cheeks of yours tight. I'm about to pull the nozzle out and I don't want you to make a mess, just rush for the toilet and relief yourself right away." Ms. Thompson instructed before yanking out the nozzle. Monroe didn't hesitate this time, instantly rushing for the toilet and letting it flow for what was pretty much the biggest relief of his entire life so far, with how on edge he had been kept it was a near orgasmic relief even, but not quite. A relief that left him completely mortified now that the pressure was finally off.

"There we go Molly, clean inside, now go soak in the tub so you can get cleaned outside too, just make sure not to dip under with your head, we wouldn't want to mess up that facial mask." Ms. Thompson instructed, barely allowing Monroe to catch a breath. He didn't object at all. Getting in bath despite how it smelled wasn't so bad, not nearly as bad as what had just happened, and at least he was left alone for about thirty minutes, thirty minutes of trying to wrap his mind around why he had just reacted that way. How could he have found that horrid penetration pleasurable? By now at least the edge had disappeared, but he was kept in more dire need of some relief than ever.

Sadly Monroe's moment of peace didn't last very long as all too soon Ms. Thompson returned to retrieve him wearing a pair of white disposable latex gloves. "Alright Molly, just to be certain that you are really squeaky clean inside I'm afraid I'll need to check, just to make sure we don't need to up your enema regime that is, bend over and hold onto your knees." She commanded with a grin, clearly enjoying herself way too much with this.