Mother May I...? Ch. 01

His older, dominant Mother-in-law who had already taken him firmly in hand, first spanking and plugging his tight little butt before locking him up? Or this new and mysteriously dangerous looking girl, appearing old enough to be his younger sister, rather than an antagonist, someone he would come to fear...

"Ahh! Please... I can do it" he cried shying away as Denise, swiftly and with two lightening quick hands, she had his track suit bottoms pulled down past his knees with one sharp 'yank' leaving his legs bared and embarrassing him further, if that were possible by this point...

"Now, now Adrian! Do as she says young man, and yes Denise, you may continue... Strip him to his panties and then bring him over here... Stand him in front of me, you know what I want after that" Margaret interjected, first telling Adrian to let Denise undress him then telling the girl where she wanted him placed before doing something else...

Something that to Adrian, it sounded like they had already planned...

"Oh wow! Very nice... Did you wear pink just for us? I love that they're boy-shorts too! You're going to make a very pretty girl Adrian... Err, I mean... You 'would' make a pretty girl" Denise commented gleefully upon seeing Adrian exposed as he was, stripped so far of his track suit bottoms and left burning in his humiliation, useless in his efforts to conceal himself.

Yet Denise, making a small faux pas of her own, dropping a clue she wasn't suppose to, however and lucky for her, Adrian was already lost in his fear and he didn't catch on...

Blushing instead, the smaller, slight fellow shivered all over, being made to lift his arms and allowing Denise to continue, stripping him down to the pink boy-shorts his wife Barb had left out for him that morning. They were his last salvation, his panties covering up his caged little nothing of a penis...

"Now, stand here young man, I think you and I need to have a few words and lay down some rules, seeing how you'll be with us for at least two weeks" Margaret directed as Denise led the woman's near-naked son-in-law over before gathering his clothes and taking them away...

"Y-yes Mother" Adrian replied as Margaret looked him up and down from her seat, agreeing without question already, he wanted her to know that he wasn't about to put up a fight...

"No... That's the first new rule... From now on you'll call me Ma'am, just like my other little girl" Margaret clarified, laying down a new rule for Adrian to follow...

"Y-yes Ma'am" He stuttered a second time, correcting himself while hearing her subtle mention of his being one of her 'other little girls'...

"That's better now give us a spin, let me see that cute body of yours from all angles... You do look good in panties my dear but as Denise just let the cat out of the bag, we will be bringing out more of the 'her' we all know is living inside of you" She stated while having him turn in place...

"In fact, I'll have you in a dress and heels before your 'wife' decides to comes back for you... If you can even call Barbara that anymore, your wife... Not with Keith in her life once again, and with all of these changes we're going through, all thanks to you I might add"

Listening and doing as he was told, Adrian turned slowly but not understanding the older domineering woman completely, he was scared and felt the need to ask...

"What... What are you going to do to me, M-Ma'am?, and Barb is still my wife... She told me she would never leave me, no, no matter what happens" he said back whining really, complaining because he didn't like what Margaret was saying, what she was inferring...

"We're not going to give you anything that you don't already want... Like wearing girly panties and even sucking cock, again" Margaret answered without holding back and leaving Adrian to shirk with her harsh words hitting his ears like nails on a chalkboard...

"I hear that since Keith has been around you've fallen back into the habit without any effort" she added as Adrian blushed in the shame, knowing Barb must have told her Mother about his being caught on his knees with a mouth full of Keith's hard cock...

"It... It wasn't like that, he made me do it that time" Adrian moaned back, trying to clear his name but by now even he knew it would be of no use, because Margaret was right... He had sucked Keith's cock on more than one occasion since his wife's ex had appeared on the scene.

Yet it was Adrian who could no longer contain himself that first time, just after New Years with all of them back at Barb's condo.

Feeling Keith's sizable, warm-skinned member in his hand, about to help put him into his wife's wet, wanting pussy. Sliding Keith's hard cock into Barb would be the ultimate sign of his approval, yet with the temptation coming on too strong... Adrian found himself with his mouth open, salivating being so close, savouring the taste of 'cock' he lost himself in the abandon, going down on Keith with both his, and Barb's sudden and surprised approval...

"Hmmm, yes... That's what you said the first time, about your friend Greg, but like him and now with Keith, you liked it... You liked sucking their cocks so much you couldn't get enough isn't that right?" Margaret prodded, prolonging this agony as Adrian cringed, embarrassed and unable to answer.

Standing facing his Mother-in-law mostly naked and terrified already he didn't dare move as she teased him about his apparent love of man-cock, all the while being aware of Denise, shuffling and moving what sounded like furniture behind him, he couldn't be sure...

Denise? Are you ready?" Margaret asked then, looking past Adrian as he stayed put, too afraid to move or know what being 'ready' could mean...

"Yes Ma'am, I'm ready when you are" The slutty looking sprite replied as Adrian, not knowing what was going on, only seeing Denise step away leaving two of the woman's padded dining chairs in the middle of the room, oddly situated back to back...

"Very good, now come Adrian, follow me" Margaret directed as she stood, rising from her chair with her black silken dressing gown flowing down towards the floor and taking Adrian by the hand, she lead him over as he hesitated, afraid and not knowing...

"Wh-what's happening? Why do you have these chairs like this Ma'am? I'm not so s-sure" He asked pleadingly as they reached the middle of the room before stopping...

"I won't lie to you Adrian, what's going to happen is, you're going to be punished" Margaret stated but then went on, sounding far too casual... "Now up you get, kneel here on this chair and then hunch yourself over, I want your palms flat on the second one... Understand?"

Directing and answering Adrian's question he looked to her with his mouth hung open and not believing...

"B-but what did I do wrong? Why do I need to be punished? Please Ma'am... It hurt so bad last time and, and I've been good for the whole two months... I've kept my cage on and I haven't complained too much...Please Mother, I'm begging you"

"Tut-tut... Remember, it's 'Ma'am' to you, and what your being punished for has nothing to do with your behaviour but rather, I'm going to tan this cute little behind of yours for not staying in touch with me" Margaret announced only confusing Adrian further, finding himself being positioned how she wanted him, straddling the two chairs with his knees press to one and his body slung over the facing backs, his open hands pressed into the chairs mirror-like twin...

"I know you've been good... However I am quite annoyed with how you've been avoiding me. Not once in the past two months have you called to say thank you for our time together... Honestly Adrian, I thought you and I had bonded on New Years Eve, but I guess you really didn't want to be here, did you? No... I don't think you enjoyed yourself at all, and if that's the case? Well... We'll just have to make sure your stay this time will be just as miserable"

"No Ma'am, please... I... I did enjoy our time together, but Barb? She didn't say... She never told me to call you or that I should get in touch... I swear I would have and, and I will from now on... Please! I promise, I'll, I'll text you everyday... I'll even take a picture of which p-panties I'm wearing and send it to you"

Listening but with her mind made up, Margaret did however like the way Adrian was thinking... His idea of having him send her a daily 'panty-pic', the word coming to her quite easily to go along with the image.

"Hmmm?... That does sound like a lovely idea but you know as well as I do that you still need this... You still need to be punished Adrian... You need to be reminded not only of who you are, but of who I am as well... I know there is a big-boy in there somewhere, one who can take his medicine" she said to him, thinking of his offer but then going ahead anyway...

"Now stay still, and get those hands back down" she instructed as Adrian quaked in his place, this awkward position his domineering Mother-in-law had him in, hunched over the backs of the two chairs and ready to be punished in some awful, merciless way...

"Denise, lower his panties please... In fact take them off altogether, he can spend the rest of the afternoon naked with his nose in the corner once we're finished with him. You can dress him up later"

First telling him he was a good-boy but then turning and speaking to Denise, Margaret was talking to the girl as if Adrian was no longer there which made him shivered and grow all the more tense, feeling the younger girl's fingers peeling down his lacy-pink boy shorts...

"Lift your knees, one then the other, that's it... Let's get these off of you bad-boy about to have his bum spanked" Denise teased from behind as Adrian shied away, her mocking voice echoing in his head like a school taunt, but still he complied. Doing as he was told he rose first one knee then the other, allowing the young blond to strip him entirely, with his panties gone, and save for his caged little dick, trembling now, Adrian was about as naked as he could get...

Quaking with fear, but staying where he was, he couldn't see the two woman as they both stood behind him. Holding his breath and filled with dreadful anticipation he knew this wasn't going to be good...

"Do you remember last time I had to punish you?" He heard Margaret ask from somewhere behind him and possibly to his left...

"I had you over my knee and used my slipper" she added as Adrian shirked again having no trouble in recalling the last time his tall, full figured Mother-in-law had blistered his ass cheeks to a fiery-hot stinging red with the aid of her fluffy-toed, feathery slipper...

"Today however, we're going to do things a little differently... Isn't that so Denise?" Margaret explained but then asking for the girl's input he felt himself welling up once again. On the verge of tears, the humiliation and undoubted pain about to befall him, already, it was proving too much...

"Here you go Ma'am, just what you asked for" he heard Denise say, probably handing the woman something, the implement of his torture no doubt...

But then suddenly he cried out and with even greater surprise..."Ahh! Ma'am wh-what? What are you doing? Th-those are my b-balls! Ohhh! Oh Mother! Owwwww!" he hollered, shocked and left calling out when feeling Margaret's long, thick fingers encircling his already trapped little ball-sack, taking a firm hold and pulling his little package out and away from his body...

Ohhhh! P-Pleeeesssee!" He cried rearing up in a bid to escape, lifting his hands for the second time as he'd been told not to, yet Denise was quick to move this time... Placing herself at his side, she kept him where he was, forcing his shoulders down as he groaned out in the shock-filled pain of what his mature, yet dominantly sexy Mother-in-law was doing to him from behind.

Squeezing like a Boa constrictor she pulled down first and then back, exposing fully his compressed balls held tightly behind the all-steel backing ring anchoring his chastity cage to his body, leaving him to scream out further and quite suddenly once again, Adrian felt the torturous sting as she began smacking his tender, undersized set of balls, repeatedly tapping away with something that felt flat...and hard...

"Whap-Whap-Whap" The sound came sharp and quick as Adrian howled louder...

"Ahhhggg! Ohhhh!"

"Be quiet you and take your medicine!... Just to get things going I'm punishing you with my wooden spoon... You need to know how useless and unworthy these two little balls of yours really are," Margaret shot back, sounding terse while explaining and degrading Adrian further.

Yet by this point, all he could see was white... Blinded by the shock of what his wicked Mother-in-law was doing, let alone the relentless, searingly hot pain she was inflicting upon his tender, unprotected balls...

"Owwwww! Oh! Oh Ma'am! Pleeeeese!!!" He bellowed out at the top of his lungs as Margaret continued, giving his overly tender little nut sack ten more sharp, stinging raps with the back of her large, flat backed wooden stirring spoon...

"Uhhhhnnngg!" He grunted with his eye pressed shut, preying this would end... He wasn't here with Margaret and Denise twenty minutes and already Adrian couldn't wait to go home...

"There... That should take care of your pathetic little balls for now... I don't even know why you have them, it's not like you'll ever give me a grandchild now will you?" She bayed, letting go of Adrian's poor, beaten balls yet not permitting him to rise or even try to get up, Denise kept him where he was, holding his arms at his elbows now and with his back arched, his body humped uncomfortably over the two dinning room chairs...

"Oh please, no more... I'll be good, I'll do whatever you say" Adrian begged with laboured breath as Denise stared at him silently, her big blue eyes looking sexy yet uncaring as she grinned, smiling with a look that said she was loving this...

"Oh you'll be good alright, and although you are being punished at the moment, later, I will be letting you out of your cage... Now be still" Margaret ordered when switching out her wooden spoon for a thick leather belt she readied herself without giving poor Adrian any time to do the same.

Laying into him then she gave his bare backside three hard warm-ups with the wide, thick leather belt folded over in her hand...

"SWACK! CRACK! SMACK!"

"Ahhhhhgggg! Ohhh!... Noooo!" Adrian hollered...

"That was just for starters.... You'll take twenty of my best and then if Denise wants to exercise a few demons of her own she can have her turn.... Now take you licks young man and stop you're screaming... You'll have the police here and then how will you explain yourself?"

"SMACK! SMACK! CRACK!"

"Owwww! Ohhh!"

Giving him shit along with the real threat of Denise being handed Margaret's belt once she was finished with him, his Mother-in-law let loose a second time, raining down several hard swats the older dominant woman dressed in her long black gown reddened Adrian's backside leaving behind several wide, thick, welting stripes.

Giving him his twenty while berating him for making so much noise, and to his credit, or in fear of the police indeed showing up, Adrian knew this certain out come would have him in more hotter water than he already seemed to be. Dropping the volume and tone of his complaint to more of a dull, droned out moan seemed like the best thing to do...

"That's better, now lets get back to it, just a few more" Margaret continued, administering his last now that he had quieted down...

"SMACK! SWACK! CRACK!"

"Unnngggg!" Adrian grunted feeling more worn out or beaten down rather than in so much pain as Margaret taking some pity on him she eased up before stopping altogether...

"Alright, that's enough for now but stay where you are, I'm not finished with you just yet" she added while tossing her belt to the side but keeping Adrian where he was, Margaret had one more item that needed attending to before letting him up...

"Here, this will help" she said as Adrian shivered and grew tense once more, feeling a cold wetness touching his fiery hot feeling skin... "Does that feel better? Some nice cooling gel to sooth your hot little bottie?" She asked in mocking, calling his stinging little bum cheeks his 'bottie'...

"Y-yes thank you... Ohhh.. Ahhh" Adrian replied with a wince feeling the cold gel touching his burning red ass but then and suddenly with his eyes flying open and his head coming up he called out once again... "Ohh! Ma'am please! That's... That's my b-buuum!" He complained, shocked and mystified once more, the lengths she was going to right from the start......

"Yes I know that's your bum, and these are my two fingers coated in slippery lube to stretch you open and to get you ready... Just like the last time"

"R-Ready f-for what? Ohh! Oh Ma'am please! Not another butt plug!" Adrian cried back feeling his Mother-in-law working her fingers into him and indeed prying him open, but still he begged wanting to know for sure, what was she getting him ready for?

"Ready for this!" Denise chimed in then, kneeling in front of the prone young man and showing him in her hands a butt plug, but oddly and much to his surprise again, it wasn't overly large and in fact it looked to be much smaller than the first plug Margaret had forced into his tight little virgin ass on New Years Eve...

"I... I don't want that in me, please do I have to?" He begged sounding less worried about the butt plug and more so about the humiliation of being splayed out as he was with the hot young Denise seeing up close as his Mother-in-law finger-fucked his openly exposed little back hole.

Mortified beyond belief and wishing the ground would open up and swallow him whole. Adrian preyed for someone to wake him up from this awful nightmare because he had to be dreaming, not believing that any of this could be really happening...

"Yes you have to." Denise chimed happily enough... "Whether you like it or not Adrian baby, you and I are gong to be besties for the next two weeks, and what better way for us to show Ma'am our love than having the pair of us wearing matching butt-plugs?" She announced, and all too gleefully for Adrian's liking, not really believing or understanding what the girl was saying...

"Here look... See what I have in me?" She added, and then much to his surprised eyes was the girl's fishnet covered backside being presented not two inches from his face...

Turning with her ass in the air and that micro-mini skirt of hers hiked up, through the coarse, wide holes in her fishnets, there, twinkling in the light was indeed a butt plug, a small bejewelled, silvery looking object wedged between the young college girl's firm, creamy skinned cheeks...

"See? Mine has a pink gem stone but yours is an Opal... It's the stone for October, that's when your birthday is right?" She asked while explaining as Adrian's gawked with his mouth hung open in surprise. Embarrassed seeing this girl's plugged ass up close, not only showing him but also reaching back, she wiggled the plug around inside of her with her the tip of a finger...

"Ye-yes... It's the same as my other one, the bigger one but please, can...can you use more lube?" Adrian moaned replying and giving in because he knew there was no use in fighting. His fate had been sealed and about all he could do was ask for more lube, something or anything that would make this easier...

"Yes, I have a full unopened tube... We bought it just for you dear" Margaret replied, dismissing Adrian's concerns as she looked over him to Denise...

"Thank you Denise, did you want to hold him open for me? Come, stand beside him and keep his two little cheeks apart while I slip this in" Margaret instructed then as the smiling pixie-blond rose with a positive nod of her head and a jubilant sounding "Yes Ma'am!"