Mother May I...? Ch. 03

Emptied of his cum, his pent-up balls being drained for good, Adrian offered a modest sounding "Yes" while nodding, hoping this meant he might be dismissed, allowed to go relieve himself but as well, he could use a moment or two... Some time to catch his breath and process some of this... Time to digest how he really felt and maybe hit some sort of a 'reset' button if he were permitted such a thing...

"Okay, well hang on if you can" Denise answered... "We're going to do this first, while you're relaxed, and then, once the tube is in, believe me, you'll be able to pee with no problem whatsoever" she replied with a smile and wink, explaining how he wasn't going to be given the break he was in need of as he was jolted aware once again.

Feeling her take his spent little dickie in her fingers and with what looked to be surgical precision, or like this wasn't her first time, Denise soon had the long, yellowy coloured catheter tube half way down into his tiny opening, equally small just like his undersized glans, the baby toad-stool of a mushroom cap making up the head of Adrian's penis...

"Uhhh! Ohh! Oh don't like when you do that... When you p-put things in me th-there... It doesn't feel right" he moaned, more so shocked than in any amount of pain with what she was doing. It had him wondering just when would all of this end?

When would she locked him up? But also, and further down the line... When would he be set free?

"Hush now sissy, it will all be over soon" Margaret said this time, telling him it won't be long but really, all she was doing was to make things that much more bleak and desperate...

"Lay back and watch with me sweetie, I'm here with you" she added, trying to provide some cold-comfort as she held Adrian's head in her one hand while bringing his upper half closer, his bare skin feeling chilled with a film of fright-filled perspiration as it touched hers...

"Uhhh... Oh God now I really have to pee.... C-can I go? Please? I can't hold it... The tube won't let me, it's letting it all out" he complained as Denise worked manoeuvring the catheter into him before quickly pulling back the rigid applicator successfully leaving the tube behind and where reaching his bladder, indeed, her actions had opened Adrian's flood gates, making him feel like he couldn't hold back, like he didn't have a choice and quite frankly... He didn't...

"Hang on! Let me get the bottle" The young girl warned as she turned finding an open topped glass beaker she had near-by, at the ready and put there by earlier, just for this purpose...

Taking and slipping the free end of Adrian's catheter tube into the bottle, Denise the cute pixie blond looked up to him smiling as his uncontrolled flow began to seep out at first before bursting like a dam, and all in just the nick of time...

"Uhhhh! Oh... Oh God" He moaned as it happened, his bladder was evacuated in what felt like a 'swoosh' rather than how he would normally relieve himself with his usual, uncontrolled trickle that had a tendency to go everywhere except into the bowl, even if he wasn't caged...

"There we go, and wow! Looks like you weren't kidding huh? Boy you really had to go!" Denise said with excitement, amazed in seeing Adrian's bladder released its contents, and so quickly with him filling the glass beaker to half way point in what was only a few seconds...

"Uhhh... Ye-yes... Oh God it f-feels weird like this... But, oh, it's also good... I didn't know I had to go this bad"

"Mmm-Hmm, I'm sure it feels different but you'll get used to it... It looks like you're just about finished'... Margaret said... "Thank Denise for helping you with your catheter, but it's time we moved on... Ask her to cage your worthless little pee-pee as well, now that you've been drained and satisfied"

Cutting in as she sat watching, Margaret, seeing Adrian pissing through a tube, it was kinky and 'weird' as her little sissy-son-in-law had described. The sensation of having a foreign object worked down into his body, and through the tip of his penis no less, she supposed he had every right to feel weird...

But at the same time she didn't want to lose control of the reigns, and showing her dominance now felt like a better time than ever... Plus she was simply swimming in the gusset once again and couldn't wait for some alone-time with her young lesbian friend, her other cute little fuck toy...

"Th-thank you... I, I guess... But are your sure this is safe? You know? Leaving this thing inside of me for six....six months?" Adrian replied thanking Denise as he was being told, yet stuttering as always, he was hardly able to say it... Admitting how long he would be locked up...

"Six-months"... It hurt his ears to say it out loud, like nails on a chalk board or acid in his mouth... Either way, it was hard to take, it seemed to be such a long time...

"Yes, it's perfectly safe, the tube can be removed and put back in... Don't worry there are people who live their entire lives with one of these, so consider yourself lucky. The catheter is just a part of your on-going training" Denise added as Adrian frowned.

Knowing he had no real choice in the matter, or if he did, they were well past that point by now with this long tube hanging out of him as he watched, seeing in Denise's hand the silvery-chrome coloured backing ring belonging to his 'new-and-improved' chastity device.

The much smaller basket-like steel cage made of eight bars all coming together forming a circle meant to encase and hold back his shrunken nub of a penis, it would give him little to no room for any growth, let alone a complete erection...

"Uhhh!" Adrian signed as Denise with quick fingers she had each of his undersized testicles pushed through the small opening with his soft deflated little dickie-bird soon to follow and thus trapping his entire package behind the thick steel hoop... His miniature penis and balls sat gathered together and held away from his body and looking lost and alone, separated from the rest of him...

"Okay I'm going to cut the tube now and insert the connector that will attach to your cage, then we'll get the whole thing on you and Ma'am can lock you up" Denise advised as she looked past Adrian and over his shoulder to where her gaze met her older dominant lovers, the woman's dark, sparkling eyes looking back at her with a lust filled pride.

Smiling but saying nothing, Margaret stayed sat behind Adrian as he lay limp and near lifeless in her arms, holding him in place as she looked on with fascination and feeling herself growing even wetter still when hearing the girl say she should be the one to have the honour.

As their Matriarch, Margaret should be the one to close Adrian's lock and seal him away...

The sexiness of it had her nipples diamond hard up top while down below she was left flooding anew, her black satin panties becoming no match or barrier against her rising arousal.

Mean while Adrian was nervously biting at his lower lip and doing all he could to remain perfectly still. He was too terrified to move as Denise continued her preparations of mating the connector with the now clipped off end of the shortened tube...

"Okay, we're ready for his cage and then you can put the lock through Ma'am" Denise said as she retrieved the small basket-like cage portion along with two small keys on a ring...

"Are you ready sissy? Be nice and ask Denise to cage you, and then you'll ask me to lock you up... Come now, I'm sure you know how this is going to work" Margaret said with a smile taking the two keys from the girl before turning her attention back to Adrian, telling him again that he needed to ask...

Asked to be caged and then ask again to be locked up... Quivering harder with the reality hitting him, thinking this looked like the end, but it was no end at all as he was seeing it now...

This was only the beginning of a new chapter, a simply continuation of this never ending torment that had become his life...

"Wh-what's going to happen after? After I'm locked up? Are, are you going to make me wear more-girl's clothes?" He asked while trying to sound scared but deeper down they knew, they all knew where he was going, what he wanted and why he was asking...

"Why yes sweetie, that's exactly what we're going to do, but something tells me you already knew that... Are you excited and want to be feminized even further? Is that why you're asking? Hmmm?" Margaret replied teasingly, knowing and recognizing the hidden, shameful desire coming out in his voice no matter how cowardly or afraid he may seem...

"I... l-like wearing the panties and the, the nightie you gave me, b-but I'm afraid... I don't want you to think that I'm....that I'm g-gay, like all the way gay, or that I want to be a girl and wear dresses and other stuff, like all the time" He admitted but also acknowledging his greater fear, labelled or thought of as being openly gay...

"Oh not this again... We know you're not gay Adrian... We've told you dear... You may like sucking cock, but with your skills in pleasing a woman, using that little tongue of yours? We also know you're not gay, or not 'all the way' as you keep saying" Margaret came back with almost sounding annoyed, but also seeing Adrian's need for acceptance, this time she threw him and bone and went over it all with him one last time, how they all know he's not gay... Or not entirely...

"What you are however is a sissy, and most boy's like you... Most of you are bisexual and we all know about your recent ways with Keith, sucking his big dick and getting him ready to fuck my daughter, your wife... But as well, this is seated much deeper now isn't it? I mean we can't forget where it all began for you now can we? Where was it again? Out in a fields with, oh what was his name?"

"G-Greg.... His name was Greg" Adrian muttered back sensing the pressure rising as he answered quietly and under his breath, feeling his Mother-in-law patients being tested in how she was mocking him... Having him say his Greg's name when she knew very well who he was, and the whole story for that matter...

"Yes, with Greg, outside in the dark of night... That's where it all started for you wasn't it? That's where you discovered this 'taste' for cock you've had hidden deep inside of you" she replied, sticking the knife in further...

"I wonder whatever happened to old Greg? It's a shame the two of you didn't stay in touch throughout the years... Who knows? You could have married him instead and become his little wifey, then Barbara could have married the man she was suppose to be with... Keith, her childhood sweetheart"

Laying it on rather thick now, Margaret opined, dreaming up a scenario Adrian could never have imagined, but still, his Mother-in-law's sentiment, saying he'd have been better off marrying Greg instead... The thought rang preposterous in his mind yet was enough to crush him, wounding his very soul.

Sat stricken and on the verge of tears once more Adrian, he stayed where he was, listening and feeling himself tremble further, he wondered where Margaret was going with this... Bringing up his past was one thing, but the way she was speaking? He couldn't be sure where this would lead or what her intentions were...

"N-no... I... I didn't want that... After school Greg moved out west I never heard from him again... I'm sorry Ma'am, b-but why do you keep asking me about him?, and saying things like that? Like I should have married him instead?" He replied feeling desperate and a little brave asking why she was so fixated in his old friend...

But for now, he didn't get his answer...

"There! I have the catheter all ready to connect with his cage... Did you want to do it?" Denise interrupted then, ending their little conversation and resting back on her heels, happy and proud of her work in preparing Adrian for his new cage. But then offering the penultimate act to Margaret, thinking it was only right for her to take over from there... Smiling she offered to hand over the reigns allowing the older woman to be the one to finalize the deal, caging then locking up Adrian's undersized, under-used, nothing of a penis.

"Yes I'd love to be the one to lock him up, again... Remember it was me who put you into your first cage Adrian dear, so maybe we should make this a tradition where it will always be me... I'll be the only one to lock you up, but as well... I'll also be the only one who can set you free" Margaret answered, declaring with the evil thought crossing her mind just then.

A delicious idea that had her sitting forward as she dangled two small keys on their ring in front of Adrian's frightened, watery looking eyes...

"This time Barbara won't have the second key" she declared, letting him know... "This time, and from here on in... I will be the one holding your keys... How does that suit you my sweet little sissy-boy? I think that's something else you should be asking me... Yes, along with locking you up, you're going ask me to be your key holder"

"I'm going to be your Mistress, your Master and your Goddess all in one" Margaret went on with a flourish of her arms, surprising both Denise and Adrian with her excited tone, as well as her announcement...

"I... I... Ye-yes, I guess that's okay" Adrian stuttered out nervous and still very unsure. But again, it wasn't like he could say no...

"Will... Will Barb be okay with it? Shouldn't she have one of the keys? You know? In case of like an emergency?" Adrian asked, sounding hesitant which was nowhere near where Margaret wanted him to be... She wanted him thankful if not begging while showing his appreciation...

"You guess?" She shot back... "Oh my, my Adrian that is not what I want to hear... You don't sound very grateful... I think you may need reminding... Are you looking to have those little balls of yours paddled and punished a second time today?" She challenged keeping her calm as Adrian turned in her lap looking to her with a white fear crossing his face.

The thought of having her use that nasty wooden spoon on his trapped and separated balls, held behind the steel ring anchoring his new cage to his body... It was more than enough to have him backing down...

"No! I'm... I'm sorry.. Yes... Yes please M-Ma'am, will you be my key holder?, just you and, and not Barb... Please don't spank me like that again" Adrian pled, scared further as he remained where he had been, perched on the edge of his Mother-in-law's seat and going nowhere...

"I didn't think so, and yes dear, thank you for asking... I would love to be your key holder, that's very sweet of you to think of me" Margaret replied, mocking Adrian as she smiled but then taking his attention away once more, his eyes shot open feeling something 'weird' once again...

"Ahhh... Ohh... What? What's that?" He asked this time looking to Denise as she put together the second to last part of Adrian's puzzle making up the parts of his new chastity cage...

"Relax... That's just the pin slipping into the receiver in your tube, it's only and inch long... Can you feel me turning it?" Denise answered as Adrian bit his lip, nodding and indeed feeling the girl turning the short steel pin inside the tip of his catheterized little penis...

"It threads into the end of your cage to hold it in place and to keep you plugged up so you don't dribble your pee everywhere" Denise added as both Adrian and Margaret watched, fascinated yet for different reasons, of course...

"Okay, here you go Ma'am, let me hold everything together while you close the lock" she said next looking past Adrian again and to her older Dominant with a satisfied smile as Margaret, grinned alike.

Reaching with her right hand, her manicured, dark painted nails and using her thumb and forefinger, Adrian watched with held breath as Margaret pressed the hasp into the lock with a 'click' and with little more fan-fare it seemed the deal had been sealed, and so too had Adrian...

Sealed away, locked up and at the start of his second, three-times-as-long stint of chastity.

A whole half year... Six months of denial, pain and humiliation with both his little penis and his ability to cum being taken way from him...

"Mmm... That felt nice... Did you feel that sissy? Did you feel me closing your lock?" Margaret asked with the rush of such control coursing through her, being the one to decide the fate of another, it was a strong, powerful experience to say the least. Certainly one she wanted to relish, remember and enjoy...

"Ye-yes... Yes Ma'am, I felt it... I'm going to be locked up for a long time... Will, I ever be let out or are you saying six months as like a trick to keep me like this forever?" Adrian replied pouting while feeling the full weight bearing down on him, the realization setting in with a simple click of a tiny pad lock...

"Don't worry, I'll keep my word and let you out when the time comes, and who knows? If you're a good little sissy, one who does what he's told, when he's told... You may find yourself being let out early for good behaviour, like they do with real prisoner's but in your case, we all know it's you're little dickie doing the time for you" Margaret replied, happy with herself while teasing Adrian further, saying he might be let out, or 'paroled' after showing some good behaviour...

"Yes, Ma'am, I'll be good, you know I will... I don't want to do anything to up-set you" he said back with fearful hope, thinking he had better obey her and everyone else or he could see himself locked up indefinitely, or maybe even worse, he didn't know and as well, he didn't want to think about it...

"I know you'll be good, or you'll try at least... However, if you do step out of line we have ways of correcting you, don't we Denise?" Margaret answered, first quelling Adrian's fears some, but then seeing the woman look to Denise, and with what she was saying... Suddenly he didn't feel as safe and secure...

"Oh yes! Did you want me to put the Glass-Purse on him now Ma'am? Just to show him?" The girl asked in answering as they both turned to Margaret, Adrian could feel himself beginning to sweat once again as he wondered, what could the girl mean...

"What's a Glass-Purse?" He asked with a naive innocence, afraid but still wanting to know...

"Never you mind" Margaret replied putting his concerns to the side "Just be good a little sissy and go with Denise, she's going to help you into your new uniform, the one you'll be wearing most days while you're here with us... Then we'll show you what you can expect, if you step out of line"

Hearing her threat but saying nothing, or knowing better, Adrian let his curiosity slip when Denise then, smiling and taking his hand he soon found himself back on his two feet as they made their way out of the older woman's living room...

Caged now and weighed down by the heavy thing like he was wearing and anchor and wondering how he would ever cope, Adrian and Denise made their way up, hand in hand as they climbed the stair to where Adrian's next fate was waiting...

Continued...