Mother May I Ch 02

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

Mother May I..?

Chapter 2

Back Door Man

As Adrian cowered, afraid and feeling shy he asked his Mother-in-law a question, no man should have to, not even when dreaming... "You're going to fuck me?"

*****

From where we left off...

"Your going to f-fuck me?" Adrian asked not believing or, seeing at least, he did know... Margaret his 50-something dominant Mother-in-law, dressed all in black, she was indeed 'strapped-on' sporting a long glossy, somewhat real looking 7-inch dildo jutting out from her loins and looking ready to do just as he was asking...

Margaret was ready to fuck her wimpy, sissy for a son-in-law and take him even further into submission...

"Yes darling, that's exactly what I'm going to do... I'm going to use my dildo on you and fuck that tight ass of yours, just like I had a real cock" she said back to him sounding rather matter of fact as she smiled, looking to Adrian while wringing her right hand up and down the smooth shafted latex dildo, her 'cock' as she liked to say.

The semi-realistic looking 'marital-aid' or sex-toy appearing to be a part of her, it's colour matching the lacy-black, all-in-one corset, bra and girdle set she had changed into replacing the long, flowing night gown, she looked menacing and untrustworthy as Adrian was seeing her.

With her full, ripe tits held high and presented, pushed up and out while encased in her corset bra, and with her legs wrapped to her upper thigh in a pair of lacy topped sheer black stockings, each held in place by one of the six garter straps built into her dangerous looking lingerie sets, she appeared every inch the stern, domineering woman she was intending...

"Oh please Mother, uhh, I mean Ma'am" Adrian pled while correcting himself...

"Please you, you don't have to do this, you know I'll be good... I'll stay naked and with, with my plug in, I'll wear it all the time and, and I'll cook for you... I'll clean too... Please! I'll do anything" he offered, truly afraid with a new wave of humiliation washing through him that sent him begging once again, saying how he'll do anything she wants from now until eternity...

However, knowing his fate a cold forbidding sweat broke out over his entire body and as much as he was in denial, Adrian also knew this was going to happen, he couldn't stop her... His Mother-in-law was going to fuck him...

"Now, now, you know as well as I do, you need this as much as you want it Adrian, and the sooner you submit, giving up this game you're playing, pretending to be shy and afraid, the more you can start to enjoy this... Don't you see? We all know... It's no secret to any of us, and as your family we have a duty to help you see this through" Margaret explained as Denise stepped closer to the woman, wordlessly squeezing out a long line of the clear lube down the top of Margaret's cock shaft allowing her to gather and smear the dildos entire length as she thanked the girl, giving her a smile...

"We owe it to you just as much as you owe it to yourself my dear, sweet sissy" she added, using psychology as a mind game, confusing Adrian's thoughts while casting doubt on his own beliefs.

Telling him everyone knows 'who' he is but saying it in a way that would lead him to believe he needed to trust her, and those involved....Adrian had to have faith in what she was saying, in what everyone were telling him...

Trembling now while lost in the two-month long fog of sexual wanting with his unsettled desires being denied time and time again, it did however make accepting and taking what Margaret had to offer somewhat easier.

But still, Adrian was afraid, if not terrified altogether...

"I'm... I'm sc-scared, and I don't think I'm like that... I...I'm n-not g-gay! I love Barb and woman please, you have to believe me" he cried in a last defence, stuttering and sounding far less confident, or convincing for that matter.

"Are you sure? That's not what someone asked me recently" Denise pipped up then as Adrian looked to her feeling all the more confused not knowing what the girl meant...

"Now, now Denise, let's not mention anything just yet... Mind yourself young lady or it will be you feeling the sting of my belt... Is that understood?" Margaret said with a tone, interrupting the young girl who looked back to the woman in dismay, surprised for being chastised and put in her place...

"Y-yes Ma'am... I'm sorry" Denise answered with a frown, however, catching herself and knowing better than to challenge her, not at a time like this, she felt bad for over stepping her boundaries...

"Very good" Margaret went on, sounding up beat as she turned to Adrian once again... "Now young man...I do I remember saying I would let you out of your chastity cage, does that still interest you?" She asked and gaining Adrian's full attention the naked young man's head came up, hearing those sweet words yet again...

"Will you go a little more easily if you're let out?" She added, asking if she let's him out will he accept her 'cock' with less fussing, yet knowing he had no alternative, Adrian did say he was willing to do anything...

"Y-es, yes please...please let me out M-Ma'am... I'll do, do whatever you want, I promise" he said agreeing but maybe not fully understanding what he was letting himself in for, what this could mean later on...

With his desperation leaning more towards his desire, rather than any last fruitless grasps at his humility, Adrian found himself willing to do just about anything to be freed from his cage, as well as being permitted to cum..

Even if that included him taking his Mother-in-law's strap-on cock up his back-side, being released from the tiny penis-prison he'd been locked into for the past two months was worth just about anything at this point...

"There's a good boy... Now you see? I'm not as horrible as you think. Trust me, we're both going to enjoy this"

Confident and with a sarcastic smile, Margaret lead poor Adrian over towards her large wing-back chair where she had him stand in front as she then took up residence, plunking her large, round ass into the low cushioned seat.

With frightened eyes Adrian then watched as the woman adjusted herself, moving closer to the chairs edge, tilting and thrusting her hips in and upward motion making the slick, black latex dildo jiggle and bob, she settled in as he shivered and quaked. Sweating now he could hardly believe what he had just agreed to...

"There we are now, come to me," she beckoned... "Turn around and lets get that plug out of you... Oh and Denise, I'm sure our little sissy-boy here would like you to add more lube to my cock... Isn't that so Adrian? Do you want my girlfriend to make my big black dick all slippery and wet for you?" Margaret asked, continuing with her harsh teasing...

"You? You want to do it with me on top?" He asked in his usual surprised stutter still not believing she was going to fuck him as she took him at the hips and turned him around, wanting Adrian to mount the big, ominous looking dildo faced away from her, impaling himself in a 'reverse cowgirl' position, it seemed even more humiliating if that were possible...

"Oh yes my little darling, you are going to work for this, and you will because I know that deep down you want this... You were born to be a little bottom bitch Adrian, your only problem is realizing and accepting" Margaret said to him, keeping it up... "With our help... Denise and I are going to teach you to how to enjoy being who you are... We're going to teach you just how to be a sissy who loves cock more than anything, even if you keep saying you're not gay"

Listening to her while standing terrified, watching with his body half twisted, Adrian looked back over his shoulder in disbelief as Denise came in then with her hand full of lube smearing more of the slippery looking gel down the length of the older woman's 7-inch strap-on making it glisten and shine anew as he watched with continual, fearful shudders running through him...

"But what about my, my cage? I thought you said I could have it off while I, while I c-cum?" He asked nervous trying to think of anything he could... Anything that might change this somehow...

Anything that might get him out of what was about to happen, but of course he knew...

"Oh don't worry, we'll be letting you out, once you've settled that cute little ass down on my big cock, then we'll have Denise unlock you" Margaret replied as Adrian shirked again not liking what he was hearing, feeling he was about to be ripped off, denied again with another one of her cruel tricks...

Telling him the only way he'll be allowed any release, any pleasure, it will happen while he's impaled to the hilt on her the slick, glossy-black imitation cock...

This wasn't what he had bargained for...

"B-but that's not fair! That's not what you said" Adrian complained, or he tried to...

"What's not fair Adrian? What did I say to you?" Margaret snapped back... "My only promise was to let you out, I never said how or when, and I'm not sure I like your tone young man... Do I need to punish you further? My belt is right there on the floor?"

Chastising as she held him at his hips, backing him up, Adrian went quiet then, knowing that if he pushed too hard he'd end up feeling the sting of her wide leather belt reigniting the slowly cooling fire raging across his rather red and still hot little ass cheeks...

"Denise, come dear... Hold him, open him up, you can remove his little plug" Margaret instructed her young blond friend and all for the idea she had Adrian half bent at the waist as she went in with her two fingers and a thumb, grasping the small rounded end and giving it an unceremonious tug that had Adrian's eye popping open while letting out a soft whimpering 'Unng" feeling his back end being vacated of the plug that quite frankly he'd become used to already, even forgetting it was there...

"There we go, now lean back, that's it step closer, Denise hold his arm help him down, I'll hold him open back here" Margaret instructed next as she watched Adrian's tight little bung wink itself closed which also and quite oddly, it left Adrian with a strange new feeling, having the butt plug suddenly removed, he felt an emptiness that came with a longing and that was the odd part.

He couldn't understand what he wanted, it was like he missed the plug being inside of him and now of all things... He wanted it back...

"Mmmm... Now there's a beautiful sight... Keep going! Can you feel my big cock-head about to push into you? Tell me, go on now... Let me know that you want it Adrian... Relax yourself and take my cock sissy"

"Ohhh... Oh gosh Ma'am... I can feel you, but, but I'm afraid.... I... I can't let go, not like you say... Please, I... I just I can't" Adrian moaned back admitting that he did want her cock pushed up inside of him but doing it for himself, being able to let go and sink down, he was too afraid... He couldn't do it, not like she wanted...

"Can I help?" Denise chirped from the background, asking as she moved in taking up centre stage in front of Adrian as he hovered in his indecision with bent knees and a strained back, unable to go any further...

"No dear, leave him alone, this is something he has to do on his own" Margaret cut in then as Denise stopped with her hands about to land on Adrian's shoulders...

"Yes Ma'am, you're right... I'm sorry" the girl apologized as she stopped, looking to her older dominant and feeling the woman's icy stare for the second time, again she knew they weren't playing games just then, realizing in the moment that there was something deeper going on between these two.. This odd pairing of son and Mother-in-law...

"Come now Adrian, no more delays, surrender yourself to me... There we go... Down... Take me, that's it... Nice and slow"

"Uhhh, Unnngg... Ohh" Adrian cried, doing it then, lowering himself until he could feel it for real this time, the slippery wet domed head of Margaret's cock first touching and then pushing in quite easily, slipping in past his already loosened-up little back ring...

"Oh yes, I'm in you now! Can you feel me?" Margaret asked, watching as she leaned back and declaring with pride as her cock slowly moved into him, first with it's blunt, round head and with each agonizing inch following after, disappearing ever so slowing into Adrian's depths...

"Unnnggg.. Yes... I... I can feel it... Ohhh Ma'am, it's, it's so b-big... Oh please, can we go slower?.... Uhhh!" Adrian gasped feeling the stiff cock worming it's way deeper as his body weight drove him down, the initial pain ripping through him and forcing him to move at a pace he could hardly stand...

"That's up to you sweetie" Margaret replied... Put your hands on my thighs, hold yourself up but keep me in... Now take a breath and tell me when you're ready... Ready for more of my cock" she directed, reassuring Adrian that this was all up to him as he followed her direction, placing each of his open palms down atop her stocking covered thighs he held himself aloft.

Half impaled on her hard but slippery feeling strap-on as Margaret was playing with his mind as much as she was playing his body.

Pushing him again, she wanted him to say it, she wanted him to tell her when he was ready... 'Ready for more cock' as she was sure to emphasize, loving the work 'cock' with it's hard 'k' adding a certain flair that turned heads when said out loud...

"Ahh I... I don't know if, if can," Adrian whined in reply, listening to her instructions while trying to hold himself up, feeling his Mother-in-law's 'bigger-than-it-looked' strap-on dildo moving into him further...

Like falling into quicksand, he had no choice, the enormous feeling sex-toy stretching his tight little butthole as he moaned the rest of the way down, Adrian was soon seeing stars with his eyes shut tight and a lemon-sucking scowl occupying his face.

With the latex cock invading his body as well as his mind, suddenly in a flash of bright light an image filled his mind. One that had him sitting bolt up-right with his thoughts going back in time, back to Greg and where in a blur of tormented emotions he pictured his long lost friend there in Margaret's place...

"Uhh! Uhh! Uhh!" He gasped with his eyes rolling to the back of his head and taking in short puffs of air Adrian was unable to exhale, caught in the moment... But not daring to say or call out Greg's name in error, but feeling this desire rising inside of him, did he really want Greg to take him this way? Would he have ever let his friend fucking him instead of just sucking his much bigger, alpha-male cock?

Working himself all the way down with such images in his head, Adrian had taken all of Margaret's big strap-on without realizing until the backs of his thighs were resting atop hers with the initial pain and shock of it all still coursing and rippling through him like a hard, crashing tide...

But still, the image was there, seeing Greg... He couldn't let it go...

"Ohh yess that's it... All the way down" Margaret declared happily watching and feeling Adrian give in, taking her cock inch by inch...

"Rest on me sissy boy, lean back and relax, that's it... Feel me in you... Mmm, you're such a good boy Adrian, taking all of my big-hard-cock"

Happy and quite turned on Margaret cooed into his ear from behind and giving Adrian no choice as she let her hands slide up from his hips to settle around his waist, her fingers interlacing at his mid-section covering his bellybutton she gently held him down, unable to move, keeping him impaled, taking all 7-inches of her hard latex cock.

Leaving him moaning in sighs and soft whimpering cries, Adrian let his eyes drift closed once more with his head lolling from side to side becoming further lost in the ecstasy being matched and twined only by the agony, the lingering, gnawing pain of taking so much cock...

"Oh wow, that looks sooo sexy... I have everything ready Ma'am, just to let you know" Denise said then partially breaking the spell Adrian had fallen into, his eyes opening to see the spiky haired dynamo had moved and was now kneeling between his splayed legs as he remained suspended, held firm with Margaret's big cock lodged up his backside firm and deep... His feet left to dangle with his toes barely scraping the floor...

"Very good dear, I think he's settled, you can unlock him now" Margaret replied looking over her son-in-laws limp, lifeless shoulder as he lay back against her, and Adrian he too was watching, seeing the smiling girl holding up a tiny silvery looking key... His key...

Coming around some, out of his delirium and filled with renewed and sudden hope, Adrian sat up partially gaining his senses where like smelling salts to a fainter, seeing the key to his chastity cage pushed him to a new level of awareness, desire and anticipation...

"Lay back sweetie, relax and watch with me, Denise will be a little while... She's going to clean you and shave you, then my little sissy-son-in-law... Then you can have your precious little cummies... Before we cage up again, and my, my... Do we even have a surprise for you there!"

Instructing him to lie back while applying light force to Adrian's chest with a hand, Margaret had him resting atop her ripe, full 38-inch chest as she spoke. Telling him what was going to happen, she wanted Adrian to watch with her, watch and see Denise first unlock and then free him from his cage...

The small, bright blue silicone penis prison left manacled to his smaller than average member for the past two, long, arduous months...

"Uhh... Oh that feels so, so much better" He cried doing as he was told, trying to rest back but it wasn't easy, not with Margaret's big cock all the way up inside him...

However, feeling Denise unlocking then pulling and manoeuvring the parts of his 'old' chastity cage off and away with the steel backing ring being the last piece, Adrian sighed with a moan feeling a mix of pleasure and pain as the tight-bodied blond pushed each of his undersized testicles one at a time back through the ring's narrow opening...

"Ahh!" He gasped with an inward breath each time, the sensation and slight pain causing his head to jerk back just as it had when he finally let go, when Adrian had allowed himself to take Margaret's rigid latex cock up into his virginal back entrance, his boy-pussy...

"Oh please" He cried then as she laid a warm, wet flannel over his freed little penis and equally tiny ball sack, followed with her hand and fingers massaging and working the wet towel all around his small, shrivelled member leaving him to squirm and wriggle with his eyes blinking open and closed...

"Just making sure you're all nice and clean... It doesn't look like you need much shaving but we'll do it anyway" Margaret informed as Adrian began to struggle wondering now how long this was going to last....

When would she either fuck him, let hum cum, or just take this big thing out of him?

"Sh-shave me? Like this? Oh please Ma'am I can't stand it any longer" he cried thinking this torment and humiliation would last forever, the pain of being stretched so far and feeling so full of woman's rubbery-stiff cock... It was indeed becoming much more than he could take...

Feeling her shift then, the stronger, bigger Margaret took hold of Adrian at his hips and began moving him with an up and down motion... Slowly, she began using her cock and her body, starting to fuck Adrian in a slow grind as he sat deliriously residing atop her thick, powerful thighs...

"Yes you can... Here, let's have a little fun before Denise shaves you" His Mother-in-law replied telling Adrian he can and will stay where he was as the girl finished cleaning him up, shaving back to smooth...