Mother May I...? Ch. 03

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

Mother May I..?

Chapter 3

Running on empty

*****

Another half an hour had passed before Adrian had finished his kitchen duties, having fed the two women, his Mother-in-law Margaret and her new acquaintance Denise, the young tight-bodied blond lesbian college girl from the sex boutique, he was then dispatched back to the kitchen were he was to clean up before presenting himself to Margaret once again in her living room...

Calmed down some but still quite shaken with how he was being treated, Adrian made his way out with every right to feel cautious...

"Ah there you are sissy-boy, come now we have something for you" Margaret chirped sounding quite happy with herself as he made his way in still dressed as he was, which was naked apart from his thin T-shirt and the vapour-thin lingerie style apron he had tied around him at the hips, and looking very much she was saying... Adrian did look like a sissy-boy.

"Yes Ma'am... Wh-what did you want from me now?" He asked in a solemn defeated tone, his head dipped to his chest and hands clasped in front of him nervously shifting from one foot to the other as he came in to present himself...

"What do I want form you? Well now that doesn't sound very appreciative and I'm not sure I like your tone, but since you've asked... Come here stand in front of me and I'll tell you what I want" Margaret replied not too fond of Adrian's apparent attitude, and saying as much she had him quivering as he stepped closer.

Placing himself directly in front of his forbidding, dominant looking Mother-in-law as she sat back in her living room chair, he knew that like everything else, this too wouldn't be good...

"We have many, many surprises for you my sweet little son-in-law, but first and foremost, I do believe I had agreed in letting you have your cummies one last time before you're to be locked up again, and yes.... You are correct, it will be for much longer this time, how doesn't six months suit? That should be a real test for a perverted little girly-boy like you... Wouldn't you agree?" She asked as Adrian stood looking down to her with his jaw falling open full of shock and disbelief...

"S-six months? Th-that's too long! Please Ma'am how, how will I survive?" He cried to her on the edge of tears, hearing such news it was too terrible to imagine. She had to be tricking him or wanting to scare him at least, because this couldn't be real...

There was no way... Six whole months? It just couldn't be...

"Oh yes you can, and you will... However before we let this happen, come and sit with me, like before, except this time it will be just you and me, I won't have my big cock up inside of you... Oh and Denise of course, she's going to help us... Or I should say, she's going to help you" Margaret answered with an arm up beckoning him over and turning nice all of a sudden, the older woman smiled up at her hapless little son-in-law as he accepted, nervously placing his smaller hand in hers...

"There's a good boy, now lets get rid of this first... You won't be needing your little apron right now, we have other clothes for you, but we'll get to your further feminization later... Now then" Margaret explained while reaching around Adrian at his waist and where pulling the light draw string she soon had the thin, wispy little apron off and leaving him naked down below as he was then sat in the small space left at the edge of her chair, between Margaret's silky feeling, nylon encased thighs, asking if he was comfortable...

"Ye-yes, I'm comfortable, Ma'am... B-but what's going on? What's happening? Why... Why is Denise putting her chair so close?, and what's all that stuff she has?" Adrian replied lying again about being comfortable as he watched confused, nervous and feeling very unsure...

"Now, now... Don't worry, Denise is here to help... Remember we said you would be permitted to have your little cummies a second time to make sure we get it all before you're caged up again?" Margaret asked, replying while trying to quell Adrian's fears of not knowing what was about to happen while at the same time lifting and ridding him of his little t-shirt and leaving him completely naked once more as he sat perched between her parted, stocking wrapped thighs...

"B-but I don't understand? How?" Adrian asked, shaking like a leaf and with no idea what was about to happen, other than knowing the two women were going to have him cumming a second time but how? That was the part it seemed was scaring him most...

"I... I do want to... I want to c-cum I mean, but why all of this other stuff? Why do I have to go through all of this? I mean, I already know... I know who I am" Adrian pled, both trying to bargain his way out and wanting to understand...

"Just who are you then Adrian? Tell me" Margaret questioned... "Say it for us... Come on now, if you know who you are then say it, really, we want to hear" she said with a near comical lilt in her voice, mocking Adrian in a way as he hesitated, wanting to say but filled to the brim with such humiliation, he stuttered and faltered, afraid he could hardly form the words...

"I... I'm a cuckold and a s-sissy-boy who..." He began, trying to be quick by rolling all of his words into one, but his Mother-in-law-come dominatrix, she had him petrified...

"That's good so far... You're a cuckold and a sissy, but go on... Say it all this time" she pushed...

"I'm... I'm Barb's cuckold sissy-boy and I... I like frilly-sissy girly things and...and I like suck...sucking c-cock" He stammered out actually saying more than Margaret was expecting but still, she was more than happy to run with it, helping him to re-enforce his belief...

"Mmm... There you go...Yes, you do like sucking cock don't you? I like how you admitted to that part, you're love of cock... You should never be afraid to say it Adrian, it's who you are and for no reason should you ever to feel ashamed... Wear it with pride... Sucking cock is a part of who you are... Now tell us again, and this time say it with meaning, Let me feel your love for cock this time my sweet, sweet little sissy-boy"

With his head turned looking to his Mother-in-law as he sat burning in the space between her legs. Listening as she egged him on, prodding him further, Adrian was all but beside himself with Denise there as well, sitting so close now with her tray of things beside her... The humiliation, it was almost too much for him to bear...

"I... I like sucking cock, it, it makes me feel different, like, like I shouldn't be doing it but, but I do... I'm... I'm a cock sucker, Ma'am... I'm a sissy and, and I love sucking cock" Adrian spat out after some time, not knowing what to say, just whatever came to mind...

"There you go... Yes... We know you looove sucking cock... Such a good sissy... See? You're learning to let go and believe me, once you do? Once you let go completely, then you'll see, then you'll understand" Margaret said to him congratulating him in a way but also confusing him some, Adrian still wasn't able to grasp everything she was saying, what Margaret meant...

"B-but what does that have to do with locking me up for s-so long? Why Ma'am? That's the part I don't under stand... Ahh! Ohh!" Adrian began but was stopped then seeing Denise doing something that grabbed his attention..

Talking and hashing out just who and what Adrian is, a cock sucking sissy, he hadn't really been watching what the young blond Denise was doing other than to know she was there... But now as he looked he had to wonder with vacant curiosity, why was she filling a rather large looking, needle-less syringe with some kind of clear gel?

But then and with a shocked gasped, feeling the girl take hold his deflated little penis, Adrian jerked sitting up-right in Margaret's arms with Denise's cold fingers taking him by surprise...

"Ahhh... What? What are doing?" He tried to say...

"Shhh, shh, quiet now, it's okay... Denise is just getting you ready" Margaret cut in hushing the frightened young man with her two strong arms holding him steady, encircled at his waist she held him still as they both watched...

"R-ready for what?" He stuttered again, asking terrified and seeing without believing as the twenty-something year old college lesbian with her narrow-tipped syringe full of what had to be lube, she pointed its opening at the end of Adrian's before shocking him further he went rigid feeling the cold gel being squeezed into the depths of his narrow little his piss-slit...

"Aggggh! Ohh Wh-what is that? Why are you doing that? Ohh it feels weird... Please, I don't like it" He cried but neither woman answered as Denise moved fast, injecting Adrian's small penis with the lube she was greasing him up from the inside as she quickly switched over, dropping the syringe back down onto her little TV table Adrian could see a series of three long, thin looking surgical tools or rods, and for now? He had no clue, no idea what they could be...

"I'm just going to stretch you out a little from the inside... Loosen you up so you're catheter can slide in much easier" Denise explained, but still, Adrian was no further along as he watched with horror in his eyes.

Perched atop Margaret's chair with her behind him, helping to hold him still while watching as intently as Adrian was, seeing Denise coming at him with the first of what were three different sized sounding rods. Starting with the smallest, thinnest of the long, metal sticks in her hand he nearly fainted figuring out where she was going to put the long, silvery looking things.

Pointed and aimed at the tip of his tiny, shrunken penis, the same spot she had injected all of that squish, weird feeling lube, Denise with what seemed like little care, she pressed in, slowly slipping the long, slightly curved 8-inch rod into him until all that was left was the round metal ball at the end, the stopper put there to prevent the rod from disappearing into him completely...

"Unnnngggg!" He cried seeing but not believing, however he was certainly feeling what the girl was doing to him...

"Oh please I don't like this... I feels too weird... Why do I have to have a catheter?" He cried again, asking and pleading as he tried to stay still, afraid to move with this long thin rod pushed down through his stiffening little penis and into his body, then to where, he just didn't know...

"Your catheter is part of your new chastity cage... It's what will enable you to last the full six months, so be grateful. Be a good sissy-boy for us as Denise does her work... Just let it happen, it will all be over with soon enough"

"Oh no! Please Mother... I, I mean Ma'am... I don't want to be locked up like this... Can't I just wear my other cage? I was getting used to it... I promise, I'll wear it all the time and not just for six months... I'll wear it for a whole year!"

Begging now as Denise moved the rod up and down a few times, letting his body reject it and push it out only to have her sink the thing back into him all the way as Adrian squirmed and wriggled not enjoying this in the least...

Removing the first rod before moving up in size she held Adrian's growing little pink-skinned member before working thicker middle sized sounding rod into him...

"Unnngggg!" He moaned feeling himself being stretched further and from the inside out in such a strange, unnaturally terrifying way...

"No sissy, this is the way for you" Margaret scolded, ignoring his pleas...

"It's symbolic if you're that interested in knowing... Both giving up your little penis and your orgasms in the traditional sense are true signs of your submission... Your willingness to obey, follow the directions you've been given and doing what you're told... You say you already know your place Adrian, but really? Do you understand just what that means? Being my daughter's submissive, cuckold sissy and what that entails?"

Questioning him in her answer, Margaret quieted Adrian's fearful outburst as Denise worked the second and much thicker rod up and down in the same manner, keeping a fingertip on it's end widening his urethral tube as he shook and shivered, fighting himself while reeling in the horror of what he was seeing.

Given no choice as his Mother-in-law pushed him further making him realize there was much more to this than just him giving in... The surrender of his mind and his will, they weren't the only things Adrian had to give up...

"Uhhh... Uhhhhh" He signed in response, trying to let himself relax as much as he could and with no other choice, no options left, he did what Margaret was telling him he needed to do most... Letting out his held breath, surrendering... Adrian let go...

"Mmm... Oh yes that's nice, isn't it sissy? I can feel you relaxing in my arms... Enjoy this Adrian dear, I'm sure if you concentrate you'll find it feels good, doesn't it? Having Denise fuck your little penis like that... Do you think you can cum this way? I'd love it if you could... It's sexy and just so damn hot... Ohhh yes sissy, take it, feel that thing moving inside of you, fucking you and making your little dick feel so extra stiff and hard" Margaret teased, feeling her son-in-laws surrender she upped her tempo with her teasing, as did Denise with her fucking...

"Oh God it feels strange but it's making me h-hard uhhh... Oh please, you're gonna... Uhhh... I don't know why but you're going to make me c-cum this way if you don't stop!" Adrian cried back sounding urgent and near the edge. The unnerving sensation of the rod moving up and down within him, while on the outside, his pretty young tormentor stroked his stiff little penis along his tender length with a single finger, the combination of the two were driving him nearer and closer to his second orgasm of the night...

And with Margaret in his ear, saying such things as she held him close her two arms wrapped around him tight... She wasn't helping his cause...

"Hold on! Not so fast, I still have one more rod left to use, its a bigger one, the same size as your catheter tube" Denise said then as she removed the middle sized steely-cold metal shaft, slipping the chrome coloured device back out of Adrian's now stiffly erect 4-inch penis yet deflating on the inside, hearing she had one more, larger, thicker rod to use on him as he moaned in exasperation...

"Unnnggg... It's too b-big...Please, go... Uhhh, go slow" He cried complaining as he held his breath turning into Margaret's shoulder afraid to watch, feeling Denise pushing the third and largest of the sounding rods into him with little hesitation, thinking he'd been worked open enough to take the much thicker rod all in one go...

"Ooops! Sorry! I guess I'm getting a little too excited" The younger girl gasped apologizing... "I'll go slow, I promise... I'm enjoying this and want to take my time... It's not every day I get to fuck the cum out of a little sissy-boy like you now is it?" Denise added mocking Adrian some as she continued, moving with an up and down motion sinking the thick rod into him with a constant pressure.

Further and further she went each time until once again the only part left on the outside of his short little penis shaft was the shiny round stopper ball held in at the tip of the girl's black pained fingernail...

"Mmm yes, what a delightful sight. I love how the rod stays in like that with just the tip of your finger holding it in place... How does it feel sissy? Are you ready to cum this time? We're going to let Denise do her thing now aren't we? We're going to let her get all of that nasty-boy cum out of you before you're caged... Isn't that right? Isn't that what you want?"

"Uhh, Oh... Oh please... I don't know what I want anymore but, but I can't uhhh, hang on... Ohhh it feels so st-strange... I think it's coming" Adrian cried with his stomach muscles pulled tight and feeling like he was indeed ready to cum, but in such an unusual way it left his mind in a muddle.

Cumming the first time while being fucked up his backside, and now this... Having his cum forced out of him so very, very differently. The sensations and implications of having this thick metal rod running up and down on the inside of his stiff little dickie, it was about all he could stand...

"Oh yes! There it is! Oh wow! Look at it coming out the sides... Now's a lot of cum... Even after the first time! it's a good thing we let you get off again huh? See how much you had stored up in these little balls of yours?" Denise asked with an excitement seeing as Adrian's orgasm hit him before she had time to slide the long steel rod all the way out, and when she did, a river of his pent-up cum followed freely behind it...

His pearly-essence a cloudy, milky-clear spew that came out of him in his usual manner, as more of a pouring-dribble running down the outside of his boy-cock than as a hard, driven ejaculation that leapt out of him.

To borrow a phrase, Adrian came with not a bang but with a whimper... His undersized balls and equally small penis were unable to achieve such status... Incapable of producing a manly ejaculation, this wasn't a thing for an underachiever like Adrian.

Soft little sissy-boys like him, they just didn't cum that way...

"Uhh, Mmm... Mmph" Adrian sobbed as his body went into contractions but then suddenly and without warning he found himself with a mouth full of more wet, cummy tasting fingers...

"Oh yes that's it sissy" Margaret barked from behind him... "Get it all, lick Denise's fingers, taste your useless seed... You'll get used to doing it this way in no time but you cummies are so thin and watery, it's no wonder you've never been able to give me grandchildren... You're little swimmers need to stay in the shallow end... They weren't meant for such things, getting girl's pregnant and playing like one of the big boys" she went on, teasing Adrian mercilessly... "No indeed... Boys and men like you, what do they do? They lick and clean up the messes they make"

Continuing to berate him and being quite harsh at that, Margaret watched as her new young lesbian lover gathered and fed back to Adrian his weak second issue all the while degrading him further. Firing one humiliating question or statement at him after another, only adding to his misery, his degradation and shame.

Telling him how useless both he and his watery little cum loads really were... Not meant for a woman's womb as a creator, but rather meant for his consumption as a sissy-boy, a non-man if there ever was one...

With his eyes closed and mouth willingly accepting each of the young girl's fingers, Adrian with tear-stained cheeks he licked and sucked, moaning with the symbolism not being lost on him this time. He knew there was a heavier gravity at work in these moments. His truest test as it were... Licking and tasting either his own cum or as of late, being engaged and crossing that boundary line with Keith, sucking real cock again after all of these years.

"There's a good sissy-boy, you like your cummies now don't you?" Margaret added, continuing to put him down... "No more fussing, you just take what you're given... I like that about you Adrian... When you pay attention and try, there really is no stopping you" she said as her crying, weeping son-in-law sucked at Denise's out stretched fingers as if each was a small, thin, penis like his own...

"Mmm... That's good, I think you have it all... I love seeing a guy lick up his own cum" Denise commented then, speaking up as Adrian blushed while regaining his senses, realizing he was perhaps savouring the taste and odd flavour of his own spunk just a little too much...

"But before we go on," the younger girl continued... "I need to know, do you feel like you need to go pee?" She asked remaining where she was, sitting on her chair opposite the odd pairing of her years older and newest lesbian conquest Margaret, and of course her sissy son-in-law Adrian, the cock sucking cuckold she was about to put into permanent chastity using a catheter tube that connects to his new, smaller and certainly inescapable, medical grade, all steel chastity cage...