Barb's Boyfriend Ch. 09

Trembling again, his eyes brimming with new tears Adrian had to look away, up to the ceiling too terrified to answer as Margaret placed a finger under his chin, bringing him back she smiled, whispering her question once again...

"Tell me Adrian... We all know that you asked Greg if you could suck his cock for him the last time, before he went away to school... Oh yes... There's no need to look surprised... Like I said my pet... I know EVERYTHING there is to know about you... But what were doing is making sure that you know it as well"

"We're here tonight, ushering you in as the submissive cuckold that you are, along with everything else... In your panties, covering up your sore, spanked and plugged up little bum"

Quivering still and forever on the verge of tears, Adrian listened while being given no choice.

He knew he had to say it, there was no way she was going to ever let this end if he didn't...

"Ye-ye-yes I... I liked it... I wanted to m-make him happy... I... I wanted him to be my friend" Adrian admitted, saying what she wanted to hear, but in his words she sensed a sadness and heart break she hadn't considered before now...

The poor guy, Margaret thought... All he wanted was a friend...

Feeling her heart pull, hearing him say he did it because he wanted Greg to like him, to be his friend... Adrian's words had Margaret cringing inwardly and thinking she might have to give up the game. However when thinking again and remembering where they were, and how far they had come, she chose to keep going, just without the name calling and making him hurt on purpose...

"Aww... See? Again, I think that's very sweet of you Adrian, a little sad even... But none the less it has made you who you are today, hasn't it? Willing to do just about anything only to feel wanted and liked? I understand that too, and believe it or not, I'm starting to recognize just what it is that my daughter sees in you... You are very submissive to her aren't you?"

"Ye-yes Mother... I'm sure you know that by now... I'm sorry, I don't mean to be smart sounding b-but"...

"Yes, of course I know, and you're right... I am beating the same drum... We all know who rules the roost in my daughter's house... Right, well... Thank you for being honest with me Adrian, I think we're finished here... But I tell you? All of this excitement has made me hungry... So, why don't you make your way into the kitchen? You'll find our dinner all ready in the fridge" Margaret instructed, sympathizing with him and even thanking him for his candour, his openness...

"All you have to do is heat everything up and set the table... I'll be upstairs changing into some evening wear and remember, after we eat, and you're tidied up, I want you to do the same, I want you changed into the night wear I have for you... It will be fun, we'll have champagne and celebrate the coming New Year, and the new you"

Listening but not daring to ask, Adrian knew his Mother-in-law had him beaten at just about every turn... Punished and back in his panties, and not to forget the awful feeling butt-plug stretching him from the inside... He thought better of questioning anything Margaret was saying.

But as well, not wanting to know, for fear of the answer... Adrian remained tight lipped as he waddled off to her kitchen with his ass plugged and by now, he was willing to do anything that would get him out of this current situation...

***

Back up stairs in her bedroom, Margaret changed into a long, black satin and chiffon night gown with nothing else on her underneath... Nothing other than a pair of stay-up stockings she had waiting and ready to slip into, replacing her other pair, the loose stockings needing garters, switched out for this pair of stay-ups and doing so with a smile on her face she loved the sensuous feeling that was making her already wet pussy just that much more damp, excited and wanting.

Aching from the inside out, she was quite impressed with how this was going, and as well with how much this was turning her on as she rose to standing and lifting up the front of her gown she was unable to resist running a finger through her mature, sodden valley, gathering her wetness... It was all she could do to stop herself from rubbing her enlarged, thick feeling clitoris to orgasm right then and there, but no...

No... For now Margaret knew better... She knew enough to save herself for later, for the grand finale of the evening, after the clock had struck twelve midnight with Adrian locked away in his chastity cage, once the ball had dropped. That's when she would have hers...

Near or before the stroke of twelve midnight she would have him perform his duty, having him employ his talented tongue, getting her off before locking him up to usher in the New Year, as well as ushering Adrian into his new life as the submissive cuckold he was destined to be...

***

Meanwhile down stairs in the kitchen, still dressed in his sweater and pink panties, Adrian also thought to don the short yellow, floral patterned apron he'd found on the back of a door handle. Thinking it might be best seeing how he was nearly naked from the waist down, yet not so concerned now with how he would look, but rather that he was covered and protected.

Busying himself in the kitchen he soon forgot about the frilly, lace trimmed ladies apron while preparing and plating their dinner as he continued to grunt and groan, doing all he could to adjust with his body and his movements being dictated and controlled by the large butt-plug residing in his ass...

"Uhhh" He moaned bending over to set the table in his Mother-in-law's dinning room, the same table where he had been sat celebrating Christmas with his wife and her parents just days before, but now...

Now everything was different... Even if it all looked the same, nothing felt that way... Not with Barb gone, off away fucking Keith as Margaret was never remiss in pointing out, with Adrian there on his own, humiliated and humbled like never before...

"Are we about ready Adrian? I'm here and waiting?" Margaret called out then as she entered the room to find it empty but hearing Adrian out in the kitchen, she smiled as she spoke, letting him know she was back, changed for the evening and ready for their meal...

"Ye-Yes Mother... I'm coming, I have everything ready... I'm just opening the wine, I'll be right out" He called through the kitchen door not realizing she had come back and feeling nervous again knowing this evening, as horrible as it had been... It was still far from being over...

"Ah yes... There you are, and my? Don't you look cute in my apron... See? These are the things that have me wondering about you Adrian... But none the less, you may continue. Serve our dinner like the good young man we all know that you are" She replied seeing him and smiling, loving that he had found and put on her kitchen apron all on his own, and of course, she wasn't about to let it lie...

"I... I found it on the back of the door, I hope you don't mind, it's just that I didn't think I should serve dinner in my under-p-pants" Adrian stuttered back, hesitating...

"You mean your panties? It's okay you can say it... In fact, say it with me dear... Tell me how much you love your panties... Say this "Thank you Mother, I love my pink panties and I'll wear them everyday, just for you" Margaret teased as Adrian he stood there, embarrassed while feeling her dial up the pressure on him once again...

"I... I... Uhhh... Th-thank you Mother... I... I love my p-panties and I'll wear them for you, ev-every d-day" He muttered back, his voice sounding dry and broken as he blushed wildly, feeling his entire body going warm, the heat creeping up his neck and face...

"Not exactly as I said it, but that will do...Thank you Adrian, I know you love your panties, all wimpy boys do...and I love that you're wearing my apron... However, after you serve you can take it off, I want you sitting at my table looking a little more proper, even if you are in your panties" She added letting him off the hook for not repeating her embarrassing little statement word for word, but as well, Margaret was sure to emphasize that he was wearing panties, pointing it out several times that they were indeed his.... His and no-one else's...

Smiling again Margaret watched as he walked away, seeing his hips swing all that much more, aided by the plug in his ass and how his panties hugged and cupped his clenched little cheeks.

"Ahh! Ohh!" Adrian winced as he sat, forgetting for the time that his ass had been spanked hard, and as well, with that damn plug literally tearing him a new one, sitting was indeed going to be a challenge...

"Aww... Is you little bum still sore? Or is it your new plug? I know sitting can't be easy but I suppose you need a good reminder, a way of letting you know your position and place for being such a bad little husband" Margaret commented as Adrian nodded, offering a weak, defeated sounding "Yes Mother" as he kept his head down looking to his dinner plate pushing the food around rather than eating any of it as he shifted in his seat, searching, but never finding any real comfort.

Eating in silence for a moment or two, Margaret smiled inward feeling better about how she had been treating Adrian, and although she was laying off on calling him a cock-sucker, that didn't stop her completely...

No not at all... In fact, she made things worse for him... This time bringing Barb and Keith back into the picture...

"I wonder where they are now... Do you think he's fucked her yet?" She asked being blunt and causing Adrian to stop with a lost looking glaze coming to his eyes...

"I'm sure they must be there and are checked into the hotel... Or if they didn't go straight up to the room and have sex, I wonder? Did they run into all of their friends?... Do you think she's told them all what she's doing?, and just where her cuckold husband is?"

Sat frozen and thinking, letting her draw this picture in his head, Adrian was unable to look up to meet his Mother-in-laws eyes as he felt himself beginning to trembling. Struck with the fear of nearly forgetting where Barb was, and who she was with...

Feeling bad, he could hardly believe he had let this truth slip from his mind...

"I... I don't know Mother... I... I just want her to be happy" He muttered again in the same dry, monotone, his spirit sounding broken but growing used to the ordeal.

However inwardly he was no different, feeling the stinging bite of Margaret's words. It was just as painful and hard to take, even if he was accepting this fate he had created for himself, and Barb for that matter...

"Aww... There you go, being sweet again... Caring about your wife's happiness over your own... I'm sorry if I'm being rough on you Adrian, but I still don't get you when it comes to this... Or when it comes to Barbara's happiness as you say... Because honestly? What man would go that far? Letting his wife fuck her ex-boyfriend, just so she can be 'happy'?"

Unable to answer much less respond, all Adrian could do was sit there, struggling at both ends, first in his mind dealing with the imagery his Mother-in-law was putting there, talking about how and where Keith was fucking his wife... But at the same time, he was also dealing with something else she had place in him... This time in ass, rather than in his mind...

"Ummph... I... I don't know Mother" He offered again not wanting to think about or picture what Barb and Keith were doing...

"Uhh... But do you think I can t-take this thing out of me? It... It hurts now that I'm sitting on it and... Uhhgg... I... I still don't now why I have to have it... My butt-plug I mean" He asked struggling now, shifting his weight around from one cheek to the other.

Sitting on his dinning room chair but knowing enough to recognize and say out loud that it was his... It was "My butt-plug" as he had declared...

"Well... I was going to take pity on you, but since you still don't seem to understand that cuckold's like you, they want and need this sort of treatment... So instead... I'm going to say no... No you may no take your plug out... The gift that I've given you... You will keep it in until you learn and accept it as a part of you... Is that understood? Or do we need to go find my slipper once again?" Margaret replied, sounding stern this time and not giving up on her end, much to Adrian's chagrin...

"Now then... It looks like you've picked at your dinner long enough... Clear up these dishes and you can serve our coffee in the living room... I also want you up those stairs and changed for the evening... We have a big night ahead of us, so away with you, and keep that plug in or you know what will happen" She added as Adrian, relieved that he was free to go, or to stand up at least.

Yet as well though, he wasn't too happy about having to keep his plug in as he pushed his chair back and was up on his feel and feeling the pressure coming off of his back end as he nodded agreeably...

Offering the same pained and drawn out "Yes Mother" as he moved with care yet with out much emotion, he looked pale and robbed of any joy in his life.

***

Following Margaret's instructions and taking 15 minutes to clean up the kitchen, Adrian was however startled and surprised coming back into the dinning room to find his Mother-in-law there, standing by the kitchen door as he nearly ran into her, entering after finishing his chores...

"Oh Gosh M-Mother, you...you sacred me!" He called out taking a step back after bumping into her evening gown covered breasts...

"Yes... I'm sure I do scare you, now come along... I'm coming up with you to help you change" She replied smiling rather suspiciously as she took Adrian by the arm, leading him towards the stairs...

"Really Mother you...you don't have to go to any trouble, I can wear my PJ bottoms... You didn't have to buy me anything else... I swear, I'm okay j-just the way I am" he pled knowing that whatever she had for him, it wasn't going to be men's sleepwear, that much he knew...

"Oh no! I insist, and from how my daughter keeps you? All smooth and hairless... Trust me, you're going to love what I have for you... Now come along, right through here... We're going into MY bedroom this time, so do be respectful" Margaret answered, warning Adrian to be on his best behaviour.

But as well, making him blush again knowing that his entire body was clean and devoid of any hair, kept that way by Barb, who as it appeared she had ratted him out at just about every turn, and proving once again that his loving doting wife?...She can't keep her mouth shut...

Led into her bedroom, held at the elbow and with not much choice, Adrian looked confused as she walked him over to her bedside, at first not seeing anything laying on the flowery, floral patterned bed cover, or not until they were there, standing directly in front...

"Here we go... Now off with your sweater, I have this lovely, soft pink little chemise-nightie that I know your going to love wearing for me... Oh and you can take your panties off as well, you won't be needing them for the rest of the evening... Let's go! Everything off young man, it's time for your bed clothes!"

"B-But!" Adrian stammered, starting to rebel...

"No buts...and there will be no bargaining either... You can cry your eyes out if you wish, but I'm telling you right now, every minute you stand here not changing will equal two minutes back over my knee where you'll end up with something much worse than my slipper... Am I understood?... Adrian?" Margaret ordered, putting her foot down...

"Ye-yes M-Mother b-but I... Please? Must... Must I..?" He pled feeling the need, even if it did mean another trip across her lap where this time he would be met with what she was saying would be a punishment that was far worse than her slipper, which he was having a hard time believing after having felt the sting of that leather-soled viper biting into his ass once already this evening...

"Of course you must... What did I just finish saying to you? Do you really want to go down that road again? Because I promise you, I will not hesitate" Margaret threatened further...

"Ye-yes Mother... Okay, okay I'll change for you but please, can...can you turn or something? I'll... I'll be naked until I put it on" He asked giving in without anymore fuss, knowing he wouldn't win and would end up with an even hotter ass if he didn't do as he was told.

However, wanting to retain any dignity he could, yet rather fruitlessly, he asked if she would turn and look away while he stripped off...

"Are you serious? Do you honestly think you have anything at all that you can hide from me? Of course I will not look away...and for that matter, come here... Just for asking, I'm going to undress you and re-dress you myself...but believe me... It will cost you later... Now come here, get this off" Margaret replied looking as angry and insulted as she wanted Adrian to believe.

But really, she was just using this as an opportunity... A way to further her authority and indeed she thought... What better way than this? Stripping him naked when he refused...

"Uhh! Oh M-Mother! Oh gosh... Alright, I'll do it... I'll get undressed! You don't have to be so rough!" Adrian cried then as Margaret, having had enough of him as she pulled and tugged his long-sleeve up and off, leaving him in a huff, all but naked now except for his pink panties.

Looking red faces and with his hair mussed up form pulling his shirt up over his head, Margaret stood back with her arms folded letting Adrian finish as he paused momentarily, hooking his thumbs into the delicate, pink elastic waistband of his panties and wanting to turn away, but knowing better, he grimaced in a sigh as he pushed the pair down off his hips and allowing gravity do the rest, the pink cotton girl's underwear sent fluttering down his legs and settling at his ankles...

"There you go... Now step out of them, that's a good boy" Margaret remark as she looked Adrian up and down, scanning his skinny naked frame as all of him came into view... Except of course for his meagre little package...

His softened and shrunken penis and pink skinned ball sack he kept hidden as best he could with his fist balled in front of him, but not covering himself completely knowing she wouldn't like him doing that, and she would tell him so.

Seeing him however, Margaret was about to do that very thing, have him move his hands or even put them on top of his head, but knowing already that he wasn't very well endowed, she took pity on him once again...

Ignoring his cowering and hiding, she let him get away with this one small indiscretion.

Shaking as he stood there, teetering in his bare feet, Adrian wasn't sure where to look but then seeing Margaret smile as she turned, he chose to stay quiet knowing there was no way out of this, no escaping this humility, being stripped naked by his Mother-in-law, and now watching he couldn't believe what she wanted next, what she was doing...

"I don't suppose you've ever worn stocking before have you Adrian?" She asked as he looked from her to the new package of nylons she had in her hand, watching as she ripped it open...

Doing this putting him in stockings, to feminize and humiliate him further, this was something Margaret had thought of on her own and without Barb knowing, thinking she would love to see his smooth, hairless legs wrapped in such femininity, but as well, she knew Adrian would love it, but not that he would let on... Not at first...

"N-no... Mother" He replied feeling reluctant and not wanting to mention the long socks Barb had him wearing the other night knowing it wouldn't help his cause any as she was about to put him in both stockings and a nightie anyway...

"Well that's surprising, but still, you'll need to sit for this...I'll teach you how to put them on, who knows? You might like them and want to do this again sometime" Margaret replied, mocking him with her comment, saying she was surprised he hadn't worn stockings in the past. But then taking his arm, Adrian flinched, fearful but also, he was afraid to tell her why...