Barb's Boyfriend Ch. 09

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New Years Eve (part two)
16.3k words
4.58
11.7k
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Part 9 of the 12 part series

Updated 06/11/2023
Created 12/08/2021
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Chapter 9

New Years Eve (Part Two)

(Author's note: This may contain elements of a bisexual nature)

Laying across his Mother-in-law's stocking clad legs and feeling the wonderful, cooling sensation of her hand, soothing and calming down his very red and sore, slipper-spanked ass, Adrian revelled in this respite, or this 'good' feeling which was short lived however as he listened to her, hearing what Margaret was saying, mentioning his past, mentioning Greg...

Feeling panicked and sick all of a sudden, Adrian knew already that Barb had sold him out again, but hearing his Mother-in-law bring it up, her knowing didn't make things any easier where it seemed that until now no one knew about him out in the hydro fields with Greg, and again in his car...

No one knew accept Barb... It was a secret that Adrian had kept close to him for a long time where he hadn't told anyone about his become his older, bigger friends personal 'cock-sucker' taking care of him when ever asked, and even volunteering himself the last time they had been together.

Going still over her stocking clad knees, he felt a cold sweat creeping over him, feeling betrayed and even more humiliated as he lay there having his red-hot, freshly spanked ass attended to by his Mother-in-law, he didn't know what to say, or even if could find the words...

"Yes, that's right" Margaret went on feeling Adrian grow rigid with fear...

"Barbara has told me all about you Adrian dear... But don't worry, I'm not looking down on you... I get it, and believe it or not, I even think it's sweet... You, doing that for your friend... Sucking his cock for him all those times" She said to him as she stopped her motions, feeling him going still across her lap and knowing she had struck a chord in him.

But wanting to be blunt and address this issue, Margaret didn't hold back, calling things as they were, and using the words to go along with it, all but coming out and calling her son-in-law a 'cock-sucker'

Quivering now Adrian was afraid to move not knowing what she was going to say or do next, only that he was embarrassed and he didn't want to look at her, he felt so ashamed with this secret and his past about Greg coming back to haunt him...

"But do you know what else Adrian?" She quizzed leaving him stymied and not knowing what else there could be... What else could she want?

"N-no M-Mother... Wh-what else?" He managed in reply, his voice gravelled and throaty...

"Well... I know we're here on New Years eve, and we just had Christmas... But if I remember correctly, I missed your birthday back in early October... Isn't that right?" She asked, confusing Adrian on purpose while leaning over into her big black carry all, switching out the Aloe cream for a tube of Astroglide along with a pair of latex surgical gloves. The snapping sound as she put them on catching Adrian's attention but still he was none the wiser...

"Ye-Yes?" He answered in a question of his own, sounding unsure, not knowing what she was talking about. Saying she'd missed his birthday? It didn't make sense yet distracted further, and with his head coming up in surprised shock, feeling but not believing what his Mother-in-law was doing, he called out...

"Ahh! Oh th-that's c-cold...and...and why are you? Oh M-Mother? That's... That's my bum!" He squealed feeling Margaret placing a hand to his ass and parting his cheeks as she let a long thin line of the slippery lubricant drizzle out of the tube and onto his exposed, unsuspecting and puckered up little back-hole.

Shocking him as she smiled, Margaret knew exactly what she was doing...and why...

"Yes I know what it is, but if we don't use a lubricant, you're not going to like your birthday present quite as much, or at all for that matter" she explained, smiling as she closed the cap and dropped the tube down beside her before using her two index fingers, sliding them up through his parted cheeks.

Smearing and spreading the slippery lube all around his clenching back passage as he called out again, questioning what she was saying. Telling him he won't like his 'birthday present' without the lube as she pushed in, sinking her long, latex wrapped middle digit in past her first knuckle...

"Uhhhgg! M-My birthday p-present? But why are you?... Oh! Mother please!" Adrian called out with his neck bent and head up, feeling slight pain and the pressure of her gloved finger sliding into his quivering back ring and beyond...

"Yes, and I'm going to give you your Birthday present... I found a lovely gift for you the other day, and I'm sure you're going to grateful and thank me once I give it to you... Won't you Adrian?" She asked, confirming that she had another 'gift' for him, but with her finger worming it's way up his ass, making him gasp in the sheer terror of being treated this way.

Being anally finger fucked and probed by his Mother-in-law? Adrian couldn't imagine why he would be thankful for what ever this next gift was that she was about to give him...

"Wh-what is it?...and wh-why do you have to d-do that? Uhhh... Oh please Mother... This... It's so em-embarrassing!" He cried, the despair and humiliation ringing out in his voice...

"Well it's like I said my dear Adrian... If we don't use lots of lube and get you ready, you're not going to like this going in... Here see? Isn't it pretty? It's a brand new butt-plug...and look... I chose this one especially for you... See here on the bottom? That's an Opel... It's your birthstone... Or it's a pretend one anyway, but I think it's lovely"

Turning his head some and trying to hold himself up, Adrian scowled, embarrassed, unsure and certainly uncomfortable residing over his Mother-in-law's lap, feeling her thick finger most the way up his ass and seeing what she was holding in her other hand... A rather large looking, silvery, shiny chrome coloured, cone shaped thing.

However not completely dumb to the world, Adrian did know that it was...and indeed he knew the big, gleaming bulb was in fact a butt-plug.

But hearing her, he couldn't believe it... There was no way... Why did she want him to have this thing in him?... And also from his vantage point, or what he could see of the plug, it looked huge causing his pulse to spike fearfully wondering how on Earth this thing was ever going to fit up his ass, and let alone why...

"B-But how? How come? I... I can't... Oh please... You... You can't do this to me... I'm sorry for being who I am...b-but haven't you humiliated me enough? That thing is going to kill me!" Adrian begged as Margaret continued either not listening or caring but loving every second, even thinking of Denise saying she was plugged and offering to show her as proof.

Pulling her finger out of him, humming even as she popped the cap on the Astroglide once more, this time squeezing out a larger dollop onto the butt-plugs shiny metal surface before smearing it around, coating the entire thing...

"Humiliate you? No dear... That's not what I'm doing." She replied after ignoring him a while longer, happily smiling as she busied herself, lubing up his newest means of degradation...

"You're the only one humiliating yourself Adrian, I mean look at you? Naked and spanked over my knee, and don't think I can't feel that little thing you call a penis... I can tell you're hard, I can feel you between my legs with your little stiffy... You like this Adrian and I'm not humiliating you... I'm helping you" Margaret explained but none of it mattered to Adrian, he knew again and like the spanking he'd just received, there was no way out, this too was going to happen...

"Be still and we'll get your plug into you... I'm sure you know all cuckold-husbands wear a plug for their wives...It's just another symbol, a way of showing us all how much of a submissive weakling you really are... The 'man' who married my daughter... If you can even call yourself that... A 'man'..."

"Uhhh! Oh God! What? No!... Please! It's toooo biiig..!" Adrian cried, first listening but then feeling as Margaret pried his cheeks apart once again, this time aiming the blunt end of the rather weighty and wide 2" butt-plug at his twitching pink little ring...

"Uhhh Ohh!" He gasped a second time as she ignored his cries, feeling her push while twisting, working the thing in and out, getting him used to it as he stretched, taking more and more of the heavy chrome plated sexy-toy with each grunting turn...

"Ooofff! Oh p-please Ma'am... I... I mean Mother... Oh ple-ese st-stop! It hurrrts!" He wailed again as she had the gleaming, slick lube coated plug most of the way in, yet leaving it there sitting at his his widest point, at the crest, Margaret stopped... Holding still she let him feel it's width stretching him to the brink before giving large bulb one last push...

"We're almost there! You can do it... Just hang on, and from what I've learned, you need to push out... Do that now Adrian.. Push out with your bum, I'm sure you know how... Do it Adrian and this will go much easier" Margaret called out, pushing and holding the big plug and stretching him at it's widest, telling him to push out, wanting him to use his internal muscles to open himself up and get him there.

And together, with one last drawn out, painful sounding moan coming from Adrian, he did as he was being told, he pushed out as instructed and his ass, it finally gave in...

"Unnnngggg... Ohhhh... Uhhh! Oh God!" He howled with his over stretched, pink ring opening and accepting the rest of the plug. Passing the widest part and sinking into him with his outer sphincter muscle collapsing, closing in around the metal plugs narrow stem Adrian gasped, gritting his teeth and with his eyes pressed shut, trying desperately to ride out the incredible pain that came along with such a humiliation... Having his ass stretched and plugged by his Mother-in-law...

"Oh it so big, Oh please... I can't... Please take it out... Oh Mother" He begged, feeling the last electric jolts of pain shoot through him as he lay there across her lap, sweating and huffing, thinking and knowing there was no way he could keep this thing inside him, not for another minute let alone however long Margaret had intended him to endure such an indignity...

"You'll get used to it... Just relax... You took that very well Adrian... Or I should say your tight little ass did, and don't make like this is your first time with something up your cute little tushy either... My daughter has been telling me many, many tales about you, and we'll be discussing them all" Margaret replied as Adrian quivered, his body covered in a cooling sheen...

"However... For now, you just lay here with me and relax, let your body adjust... You can't lie to me Adrian, even though your little dick has gone all soft on me, I know you still like this, and I think it's cute... Plus it's rather fitting for a guy like you... Don't you agree?"

Laying there trying to listen and breath, doing as Margaret was telling him as he struggled to adjust and get used to this alien invader residing up his ass, Adrian closed his eyes visualizing and feeling his anal ring closing in around the cold, steel butt-plugs thin tapered stem, locking tight and keeping the rest of the big gleaming orb deep inside him.

Opening and stretching his inner passage, his mind began to shift, feeling the betrayal and humility of Barb telling on him. Telling his Mother-in-law about his past, and of their private life, all their bedroom secrets...

***

Letting him rest for a few minutes, seeing his ass wiggle and move, trying to adjust as Margaret she quietly hummed a soft lullaby and lightly stroked Adrian's back. Moving lower, she let her nails and fingers skate over and across his still red looking ass cheeks. Soothing she calmed him down, letting his breathing settle as he stayed quiet...

"Stand up for me Adrian" she said to him after another moment, breaking the quiet and feeling enough time had passed...

"I think your little bum will be fine, and pull up your panties as well... But then I want you back down here, on your knees... You still need to be shown your place when you're with me" She directed as his eyes came open and somewhat back to reality...

"We're going to talk for a while, and then I have a meal that you will serve, and you'll also do the dishes before I let you have a glass of Champagne with me as we ringing the New Year" She added, instructing Adrian as she had him move, righting himself carefully and feeling a little queasy with his face in a knotted grimace.

Moving slowly, fearing his plug might pop out if he went too quickly, yet also knowing it was almost impossible, the thing felt so big it left Adrian sniffling along with his face being a mess of tears and looking red enough to match his still sore, slipper-spanked ass.

However on the other side of this, Margaret was smiling with her plan falling into place and left feeling better than ever... But as well, knowing how broken and vulnerable Adrian must be at the moment, she took pity on him in her mind, but staying firm on the outside, she had him back kneeling at her feet, reminding him of where he belonged.

Standing and pulling his pink, full panel panties up and over his sore ass, Adrian grunted all the way, and coming back down as instructed he settled to the floor folding, his legs under him and with his ass plugged and spanked, sitting off to one side was the only comfortable position he could find...

"So... I guess we should start at the beginning hmm? Did you want to tell me about you and your friend Greg? Or do I have drag it out of you playing twenty questions?" Margaret began, getting right to the point about his past...

"Remember Adrian... I'm not looking down on you, I just want to hear the story from you instead of relying on Barbara and my own imagination" She continued, asking Adrian if he wanted to tell her of his early days spent not unlike he was at that moment, on his knees, but with Greg, and for an entirely different reason...

"I'm sure you know enough from what Barb has told you... I mean, do...do I have tell you?" Adrian replied softly, feeling humiliated enough and not really sure what the recounting of his time with Greg was going to accomplish, except to embarrass him further...

"Yes, I do know enough... But now that I'm more 'intimately involved' let's say. That's what I want from you... I want intimacy... I want details and to be included, and also? I like the idea of you doing that, sucking your friend's cock for him, and don't forget, I also thought it was sweet... So yes please Adrian, indulge me... Tell me everything" She went on pushing him as he knelt at her side feeling so outed and so humiliated.

Pausing however, Adrian looked to her almost praying for mercy with his watery, tear-wet eyes. Thinking and knowing he could never say... He could never tell her the story...

"Remember Adrian" Margaret added, pushing him further... "Your wife... She has gone away... My daughter has left you here with me while she's off fucking her ex-boyfriend, and they won't be back any time soon... So take your time my sweet little son-in-law... Because as it seems? We DO have all night" She finished, cutting him further with her tone and inflection, reminding Adrian again of where his wife Barb was at the moment... Off fucking her ex-boyfriend Keith, and with his weak-willed acceptance no less.

Sensing his reluctance however, and knowing he wasn't going to tell the story of Greg all on his own, so in order to help him, Margaret reached out in an act of pity, putting a hand to the back of his head, she held him closer, his cheek touching her nylon encased outer thigh as she spoke, telling him that she understands... Yet doing so in a way that had Adrian thinking the opposite...

"Okay... I get it" She began, stroking his hair. sounding kind in her voice and with her gesture...

"I know it must be hard for you to sit here like this and tell me all about your cock sucking ways... So instead, I am going to ask you some questions" She said to him in calm, yet confident, commanding voice. But without relent, she cut him deep once again by using such crude terms...

"But I want you to look at me when I do... Alright Adrian? I'm up here little boy... Look at Mother while she asks you about sucking another man's cock" She went on, being derisive like this on purpose, mentioning 'cock' and 'cock-sucking' where, and whenever she could.

Margaret had decided that if Adrian wasn't brave enough to tell her the story? She was going to do this her way, which included name calling, subjugation and even more humiliation...

"I'll begin by saying this" She added with his full attention...

"From what I know? Or from what Barbara has told me... The first time you sucked Greg's big dick, you let him coax you into it... Is that right?" She asked as Adrian swallowed, blinking his eyes closed while nodding out a shy, embarrassed 'yes' with his head while trying as he could to keep his eyes focused to hers...

"Okay, that's good... I mean at least he didn't force you, but I figured it was that way because well... You did it again didn't you? You went back for more... You went back for more cock" She replied, sounding relieved that Adrian hadn't been raped by this older friend or coerced in a bad light.

But also asserting that he must have liked it because he did go back, he went back for 'more-cock' as she said it, sticking the knife in just that much deeper.

Unable to answer all Adrian could do was look to Margaret as she did the talking, and again being so graphic, hearing the way she would say 'cock' it was like nails on a chalkboard, hurting and biting into his ears, it was all so humbling and soul rattling...

"Yes, I like sucking cock too... But then again... I'm a woman and I'm suppose to like men... However as for you Adrian? You're not a girl are you?" She asked as he looked to her, frightened and wondering where she was going with this...

"No... You're not a girl, but tell me... Can I ask you Adrian?... Is that what you want? To be a girl? Or to just be 'like' a girl in, your case?" She asked with the harshness and teasing in her voice never fading...

"N-no... No I don't w-want that... Please you, you have to understand... I'm not like that... I'm not g-gay" Adrian muttered speaking at last, or feeling he needed to as she smiled, knowing already that he wasn't gay but hearing him trying to defend himself, she thought it was so cute, Margaret enjoyed his begging...

"Are you sure? You are wearing panties after all, and I do believe you've told Barbara that you like wearing your other piece of lingerie... Your satin cami-set... The one you were given for Christmas... Tell me? Do you have that one with you? Were you planning on sleeping in it tonight after we ring in the New Year?" Margaret teased further, trying to look serious but her enjoyment was taking over...

"N-No Ma'am... I... I mean Mother... I have my PJ bottoms, a t-shirt and c-clean underwear for tomorrow"

"You mean clean panties, don't you? But never mind that for now... You won't be needing anything in your little case, I have something all picked out for you to sleep in... Consider it another loving gift from me to you... But anyway, where were we? Oh yes... We were talking about you, sucking cock"...

"Please Mother... Do... Do you have to say it like that? It was along time ago and I was im-impressionable, you...you know? Like I am with most things I... I just sort of go along with what I'm told, and well that's...that's how it happened with...with G-Greg"

Showing some backbone at last, Margaret looked down to Adrian, her eyes wide with amused surprise, listening as he finally spoke, uttering his first wilfully coherent sentence as he tried to stand up for himself...

"Yes... You are rather obedient always doing what you're told... I'll give you that Adrian, and I will 'try' not to call you a cock-sucker... I'm sorry, but I just can't seem to resist... However, tell me one thing and I'll leave you alone... Tell me you enjoyed it Adrian... Tell me you liked sucking Greg's cock... That's all I want to hear... Just admit it... Tell me you liked sucking cock and I'll leave you alone... For now"