Mother May I...? Ch. 05

(Author's note: This story carries a femdom, semi-incestuous and bisexual theme throughout)

Mother May I..?

Chapter 5

Meeting your future past...

*****

"Well it's about time... I was beginning to think the two of you had eloped or something... What were you doing up there?" Margaret asked from her wing-back chair as Denise entered the living room first, wanting to surprise the older woman she had Adrian hidden tucked in behind her dressed in his frilly-pink maids get-up...

"Sorry Ma'am I was only doing what you told me and here, see for yourself... Doesn't he look amazing? Or 'she' I should say?" Denise answered not so much going on the defensive but rather showing the older woman just what the two of them had been doing all of this time.

Pulling Adrian out from his hiding spot Denise had him standing front and centre, presented in his newest form... Dressed head to toe in pink and ready to be their sissy-maid...

"Oh yes! Wow!" Margaret declared sitting forward excitedly in her chair, seeing Adrian as he now was...

"I'm actually impressed... Come, come closer let me get a better look" she directed, surprised with how real her little son-in-law looked all dressed up in his costume, complete with make-up and a matching pink silk choker Denise had slipped around his neck to go along with a tiara like maids-comb topping his head before finishing him off with a pair of low-heeled matching pink patent leather sandals on his feet that left his equally pink painted toes visible through the open ends...

"My, my indeed" she quipped quite taken as Adrian said nothing yet feeling the gravity of the situation, that much he couldn't ignore... Standing presented in front Margaret and feminized to his fullest, he could feel his cheeks redden and his temperature rise as she looked him over, assessing how much of a sissy-girl they had turned him into...

"Turn for me, all the way around" His Mother-in-law instructed as Adrian standing with his hands clasped in front of him, he did as he was being told, making a small circle where he stood, allowing her to see him from all sides before returning to face her once more...

"Mmm, yes... Very pretty indeed. But move those hands, you can't hide form me, I can see your skirt is doing it's intended, cut this way. I like how it keeps that caged little clitty on display, it's the proper look for you... But I suppose it's rather humbling isn't it?" She added, asking as Adrian sighed with a weak sounding "Ye-Yes Ma'am" when dropping his hands to reveal himself...

"I'd say so, and I can't imagine you're very comfortable dressed as you are but not to worry, you'll only be like this when you're here, otherwise I have a whole new wardrobe for you, clothes that are a little more suited to how the world sees you" Margaret continued as Adrian felt somewhat relieved glad to hear he wouldn't be dressed like this all the time, if that was any consolation...

"Now... What is it you were doing earlier? I believe you were in the kitchen... Cleaning?" She asked, but more so stated, telling Adrian where he should be as he caught on, he didn't mind though, being sent away. At least he wouldn't be gawked at doing dishes and mopping Margaret's kitchen floor, it was about the best thing he could hear just about then...             

"Ye-yes Ma'am... But can I get you anything? Before I start cleaning? Coffee or, or something stronger maybe?" He replied thinking it might be good to play his part, offering to serve drinks or bring her whatever else she may want before he's put to work...

"No thank you... However as you mention it, Denise and I, we do not wish to be disturbed for the next little while, is that understood? No matter what you hear through that door, because I know you'll be listening yet under no circumstances are you to enter, unless I call you"

Directing and telling Adrian she didn't need any refreshments, Margaret did however warn him about walking in on whatever it was she and Denise found themselves doing...

"Ye-yes Ma'am... I won't come in, no, no mater what" he answered feeling nervous but also with a twinge of sexual jealousy... Feeling a little left out he was hoping he'd be able to watch at least... Watch and see his Mother-in-law and her new little sex-pot girlfriend doing what have you, no doubt engaged in more lesbian sex, and doing it right there in her living room.

"Where would you like me to start Ma'am?" He heard Denise asking the woman as he turned to leave and with Margaret replying... "You know where I want you... Down you go, you can start by using that tongue of yours on my very excited little butt-hole"

Gasping some but knowing enough Adrian stepped through the kitchen door, he was however able picture in his mind where indeed Margaret wanted the girl to start... As she had said, with her tongue in the older woman's back door, rimming her rear cleft, he imagined his Mother-in-law kneeling backwards on her chair with her ass hanging off the end, spread apart and made available to the young blond.

Shuddering some with the vision, Adrian chose to step away just then, knowing better than to hover around the door listening as Margaret would suspect he would be doing, and so with regret he made his way over, turning on the kitchen taps hoping to drown out any noise as he put himself to work, doing his sissy-maid duties of cleaning, mopping floors and putting the dishes away...

*****

An hour or so later...

"Adrian... Sissy-boy you can come back in now... Denise and I are finished and I need to speak with you... I know you're hiding on the other side of that door, so get in here" Margaret called out as Adrian took a step back. Having finished his chores then choosing to eavesdrop if he could, but afraid now thinking he'd been caught, he paused and waited a second or two longer before pushing open the spring loaded door...

"Ye-Yes Ma'am? You c-called?" He stuttered fearfully upon entering with his eyes set to the carpet and wanting to keep his gaze averted, once more afraid of seeing anything he shouldn't...

"Yes dear, Denise and I have had our fun... Tell me, did you enjoy listening? Did we make your little dickie feel all tight and uncomfortable in your new cage?" Margaret asked, teasing Adrian as he stood near the door dressed in his all pink and white costume and looking as silly as he felt, his hand clasped in front of him once again, doing what he could to hide his shame...

"It... It feels alright, Ma'am... Is, is there anything I can get for, for you?" He asked when replying, wanting to be as attentive as he could, or more like he was kissing her ass to stay on her good side as he also tried to change the subject...

"Yes, I want you to go and change... I've suddenly had a craving for steak and I think I'd like to go out for dinner this evening" Margaret directed, and shocking Adrian some he didn't quite understand... First about the steak and then about wanting to go out...

"You? You want me to go out? In? In clothes like...like these?" He asked terrified now thinking he was going to be seen in public dressed in something that was likely to be feminine in nature, more girl's clothes that would no doubt be worse in some way...

"That you'll have to find out for yourself... You didn't happen to look in your closet did you?" Margaret questioned as Adrian quivered while thinking he hadn't opened the closet door in her spare room, his room during this extended stay...

"No Ma'am... I haven't... I've only been here since this morning" He answered being truthful...

Adrian had only been there a short time, yet with everything the two of them had put him through so far, it felt so much longer.

In fact to Adrian this whole day felt like it was taking a life-time to pass, turning into one of those days that seemed to last forever, continuing like a bad dream from which he could never wake...

From his arrival and being stripped, to spanking his two undersized balls before fucking him up his backside and taking his anal virginity, then later milking him dry... As well and not to forget, locking him up in his new and very permanent feeling chastity cage... Adrian could hardly believe this had all taken place in the last four or five hours... And frankly, neither could Margaret...

"Yes, you have only been here since this morning and it seems time does fly when you're having fun, isn't that right?" She replied with a sly smile coming to her lips, assuming Adrian must be enjoying himself, seeing how the time had slipped away so effortlessly.

Yet from where he was sitting, quite the contrary was true... First of all, he wasn't having all that much fun, and secondly with everything that had happened in such short order? Adrian had to wonder if this next two weeks spent in purgatory, feminized, chastised and humiliated... Would it too ever end?

At the moment, he didn't think so...

"Very well then off you go... I'm sure you can dress yourself... We'll be leaving in an hour and you don't need to look so worried, I'm sure you'll find something suitable to wear"

Dismissing Adrian once again he was glad to be sent on his way and wondering now he had to hope and believe that whatever clothes Margaret had for him, there was no way it could be any worse than how he was currently dressed... Or could it?

Entering the small, wood panelled bedroom with it's North facing window allowing little light, Adrian clicked on the over head bulb and with baited breath and trembling fingers he pulled open the two bi-folding closet door hoping whatever his Mother-in-law wanted him wearing in public, it would only be as bad as his track suits and the flat-soled, tasselled loafers Barb had him wearing when they went out...

"Hmm? Well, this isn't too bad, I guess" Adrian hummed as he paused, standing in front of the open closet and looking he was surprised to see that the clothes left for him they were a lot 'kinder' to him that he fight might have thought.

Meaning he wasn't faced with a hanging racks of girls dress, feather boas and stacks of women's shoes, but no... Looking now that wasn't what he was seeing and with the air let out of him, having prepared himself for another fight, he was quite pleasantly surprised to find the clothes were indeed rather modest... For what they were that is...

"I guess I can make this work" he said next reaching in and removing what he thought at first was a guys' blue-gingham, or check print, long sleeve button down, but once out of his uniform, his girly pink, filly-laced maid's get up and with the shirt on, for reasons he couldn't figure out, it felt different, and odder even still? the buttons, they fastened from the other side...

Stepping to the mirror while wondering why, but then looking seeing himself and cringing with his face still made up, the pink velvet choker around his neck and on top of his head the fan-like tiara, or comb, and thinking suddenly just how ridiculous he looked. Adrian knew right then and there that he couldn't just change and head back down... No, would need to shower first and wash his make-up away...

"Oh God I have to get this stuff off, and now!" He guffawed, quickly shucking the blue cotton shirt and before making his way naked out into the hall, not even thinking all he wanted at that moment was a hot shower and a hand-full of face-cream to get rid of the make-up and heavy eyeliner.

*****

Mean while down stairs...

"This is going to be amazing, Adrian is going to be so surprised" Denise chirped as she and Margaret found themselves alone once again, having dispatched her sissy-son-in-law up-stair to change out of his girly-maids costume after being told by Margaret that she wanted to dine out, which was true... However, what he didn't know was where, and with whom...

"How do you think I felt when Greg messaged you back?" Margaret replied, agreeing that Adrian will certainly be surprised once he sets eyes on his old friend again, if not lose his mind altogether.

However, both woman, the elder and the younger, they too were taken aback some when the girl's phone chimed with Adrian out of the room, and lucky for them they had finished their little love making session with Denise strapping herself into the big black latex dildo this time and giving her Ma'am a 'Jolly good Rogering' as her grandfather would say...

Fucking her Mistress, the girl's much older, dominant lesbian lover with the 7-inch sex toy, helping to rid the woman of her pent up frustration, what with Adrian being subjugated and taken care of the way he had, Margaret had been left wanting more... Much much more...

But then, and as luck would have it they were able to communicate with Greg, starting a live dialogue that did not end until Adrian had been called back in...

Surprising them both but overjoyed none the less, and through a quick series of text messages some things were mentioned as to Adrian's current status that had the result ending with Greg inviting all three to Woody's for the as mentioned, steak dinner...

"I wonder if we should have told Greg more though, like about Adrian being feminized, and about his cage?... What if stuff like scares him off?" Denise asked thinking with a bit of caution that Greg might not go for that sort of thing, becoming involved with a simpering caged up little sissy-boy...

"You read what he said, he's an open, out, gay man and quite the Alpha it would seem from his profile photo... He's quite the hunk, but anyway, he runs a gay bar so I'm more than sure he's come across his fair share of sissy-boys like our Adrian, and if we're lucky, he's still the top he was with him all those years ago... So, I wouldn't worry too much about him not taking to our little girly-man... Because you know what they say? A Leopard never changes it's spots and neither do guys like him"

Explaining and telling her young girlfriend not to worry while smiling as the two woman sat, Denise felt better understanding what Margaret was telling her, caught up in the hype of it all this part of the male psyche, it never changes...

Once a man is who he is? Rarely will he change...

"I guess that goes for Adrian too huh?" She asked as Margaret looked to her slightly puzzled...

"He's be acting like a girl and he might even be gay but won't admit it" Denise explained... "And just like Greg, Adrian is no different either... He's been like this all of his life so, yeah I agree, guys don't change, even if they are trying to be girls!"

Tittering to themselves for a second or two, Margaret thought it might be time for the pair of them to head up to change as well, plus she wanted to check on her little sissy-boy, see if he was finding all of his new clothes alright...

*****

"How's it going in here Adrian?" Margaret asked as she stepped into the spare bedroom to find Adrian there but not dressed, he was still going through the dresser with a somewhat annoyed, puzzled look on his face...

"N-not so good actually... I don't mind that all of these panties are for me, I haven't worn guys underwear in ages anyway but I, I can't see to find any socks, just these knee-high stockings and several packages of pantyhose?"

"Those are your socks now Adrian, and what's the difference? No one will know what you have on under your slacks, just like you panties and your caged up little dickie, no-one will see them either now will they?" Margaret asked, telling Adrian he didn't even have a pair of socks, just more hosiery...

"I... I have to wear knee-highs? But what if I'm in shorts?"

"Really Adrian? Are you that dumb? How many women have you ever seen wearing knee highs with a pair of shorts? You won't need them, now quit this stupid routine and get dressed... I have to get ready myself and I don't need to be wasting my time fussing over you now do it? But since I'm here, you'll wear this top and the blue slacks, now get going"

"B-but this is a b-blouse! It, it has flowers on it" he complained, seeing the top she had pulled down from it's hanger and tossed at him...

"Yes, they're all blouses as you say Adrian, but this one isn't too obvious, and yes it has flowers on it but they're on the inside, you'll only see them with your cuffs rolled up, now here... Wear this underneath, it's still a little chilly out so you'll need something else" she added finding and handing him what at first looked to be a plain, light blue coloured undershirt but looking closer, and seeing it's spaghetti straps, along with low cut square front trimmed with a light lacy detail... Meaning yes it was an undershirt, one meant for a girl, and a very flat chested one at that...

"Oh and I suggest you go for a full set of pantyhose if I were you, your slacks are just as thin and a full set will act like long underwear... Now is there anything else Adrian?" Margaret asked, sounding frustrated and like she'd about had enough of him...

"N-No... I guess not... I'm sorry for being, uhh fussy like you said. I just don't want people to laugh at me" Adrian replied, feeling berated and put in his place, knowing form Margaret's tone she wasn't happy with him and so not wanting to push his luck any farther, lest he wanted another taste of her leather belt tanning up his backside, he dropped his clothing fight, agreeing to wear what the woman was handing him...

"Yes, well, I don't think you'll have to worry about that so much tonight... Not with where we're going... Now finish up in here and go wait for us in the living room and in fact while you're down there run a vacuum around, you'll find it in the front hall"

Finishing off, Margaret this time she was the one to slip, inadvertently telling Adrian he needn't worry about how he looked or being laughed at, not with where they were going but realizing and quickly veering off, she dodged any more question by giving him an order before stepping away, leaving him and making her back towards her own bedroom.

However Adrian, already lost in his world of hurt, trying to figure out how he was going to get away with wearing the clothing she had chosen, he didn't pick up on what his Mother-in-law had said, but then distracted further he came to realize something else he hadn't notice until just then... Dressed in the little cami-top as his undershirt and then choosing to step into the trousers, he hadn't noticed until now that these 'slacks' they were in fact lady's dress pants...

"What the heck? Why is the zipper at the side and why is it so small?" He asked out loud but to himself as he looked up then, seeing his refection in the mirror mounted to the back of his bedroom door... "Oh man! These are girl's pants... Now I know why she kept calling them slacks! Damn, can't I catch a break here and have just one normal thing back in my life?"

Looking to the pair of pantyhose left on the bed and still in they're wrapper, he thought about not wearing them thinking the pants, or slacks looked like they were going to be a tight fit already but then sighing and thinking again, Adrian picked up and opened the package knowing that Margaret would ask if he was wearing the tan coloured 'All-in-one Control Tops' as the outside advertising described... And so in an effort of self preservation, he sat on the bed and tried to figure out how they went on...

"Gosh, how do women do this every day?" He asked struggling into the tight nylons, he remembered watching as Denise put him in stockings which seemed much easier because they went on one at a time, but with these pantyhose, they were joined making them harder to work with...

"Unnnggg, Uhhh" he grunted sighing again, tugging and fighting his way into the pair, learning as he went, working first one then the other up his legs a few inches at a time, enough to let him stand as he shimmied the rest of the into the tight, flesh-tone, or 'nude' coloured tights...