Barb's Boyfriend Ch. 10

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"Happy New Year Cucky!"
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Part 10 of the 12 part series

Updated 06/11/2023
Created 12/08/2021
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Barb's Boyfriend

Chapter 10

"Happy New Year Cucky!"

****

Ringing in the New Year with Margaret closing the lock on Adrian's chastity device, pressing the two part together, the sound was faint but with his elder Mother-in-law behind him calling out and counting down, even over her booming voice never had he heard anything so loud...

The lock closing, it left a ringing in his ears, the sound so loud and deafening it was enough to drown out all others...

****

The next morning... New Years Day...

Having slept alone in the same bed he and Barb had shared no less than a week prior, Adrian woke feeling disoriented and unsure, not knowing where he was for a second until it dawned on him and he began to remember...

However, for the time being... He had a different and more pressing issue holding his attention...

"Ahhh, Oh I gotta pee so bad... Oh fuck...this thing is killing me!" He moaned rolling over not only remembering where he was, but also just why he had this 'thing' attached to him that was hurting so bad... The tiny, baby-blue and all constricting chastity cage Margaret had put on him and locked up tight with no hope of escaping.

"Oh oww, oww, oww" He winced hopping out of bed, all but forgetting how he was dressed as he scampered out and down the hall, hoping and praying his Mother-in-law was still in her room and not using the bathroom he so desperately needed.

Ducking in and closing the door Adrian was quite relieved to find the bathroom empty but catching sight of himself in the vanity mirror a different type of shock ran through him. Dressed in 'his' dusty pink, and very short chemise night dress he felt ridiculous still wearing the wispy women's sleeper...

"Oh God... What have I become?" He ask but with no more time to worry, quickly plunking himself down onto the toilet seat, desperate to pee but learning the hard way the night before, he knew now that while in chastity... Sitting... It was the only way for him to go...

"Ahhh... Oh God this thing feels so tight... Why do I get so hard in the morning?" He asked aloud in distress while trying to let go, but being hard, the steel backing ring on his bright blue chastity cage wouldn't let him.

Having spent a mere few hours locked up, Adrian had only been through this experience once before... Going to the bathroom that is... Later in the evening before bed and after a good few glasses of Champagne that followed his second 'attendance' to Margaret, his Mother-in-law...

"Ohhh... Oh yeah that's good" He sighed as his tightly compacted little dick gave up it's game. His morning wood shrinking enough to allow his bladder to let go, Adrian sat with his eyes closed listening with his cage tucked between his legs, hearing his stream spraying out and hitting the sides of the bowl.

Learning that standing while peeing, it was an impossibility while trying the first time but then arresting himself and stopping his flow... Adrian knew in an instant that standing while going to the bathroom when locked up... It wasn't going to work...

Even if the open slit end was rather wide and long, it didn't matter as his pee came out 'every-which-way-but-down' causing him to stop and scramble while reaching for the toilet roll to dab up his mess knowing he would have to sit if he was going to finish what he had started.

Relieved at last and at the sink washing his hands, Adrian looked to himself in disgust. Seeing himself dressed in a girl's nightie and his chastity cage with it's bright, baby-blue colour sticking out like a sore thumb... It was all just another reminder of who he was, but more so now, it was pointing to who he had become...

"Are you in there? I have coffee on if you'd like some... You can dress in your regular clothes, although I've picked out a fresh pair of panties for you... I went through your little carry case, but I'm sure you don't mind"

Hearing Margaret speak and caught off guard, Adrian jumped where he stood at the vanity sink. Frightened with his pulse spiking quickly, hearing Margaret's voice on the other side of the door, it made everything real again...

He was indeed here, and this wasn't some crazy, never ending nightmare...

"Uhh... O-Okay M-Mother... I'm just washing up... I'll be right down... Th-thank you" He replied while staying still and not even thinking of making a move to open the door or let her in. He was so embarrassed, he didn't think he could face her dressed as he was... Still in his feminine night gown and nothing else, leaving his caged little package unmissable and on display below his far-too-short hemline.

And as well, hearing her say that she's left him out a fresh pair of panties? That was cringe worthy enough thinking that from now on that this too would be his fate. Dressed in panties everyday, picked out for him by either his wife, or his Mother-in-law.

Waiting and hearing her walk away, Adrian stayed where he was for another minute with his breath held before opening the door and stepping out with a sigh, realizing that thankfully she had gone and he was alone.

Dashing back to the small spare room and quickly closing the door behind him, Adrian's relief was palpable, yet looking to the bed, the feeling was short lived because sure enough, and just as Margaret had said... She had been into his room and indeed she had gone through his bags.

Searching casually as she pleased, Margaret found the panties she wanted him wearing that day... A new pair from the six-pack 'gifted to him at Christmas' or so he had been told...

"Green huh? Well, at least they're not pink again" He said aloud as he stepped over and picked up the light green or teal coloured pair in his fingers, but still, another quake ran through him. Holding 'today's' pair of panties he was meant to wear... It was chilling in both the reality and the hidden fantasy, his own desires being met... It made him feel sick, just as much as it turned him on...

***

Dressed and entering Margaret's kitchen, Adrian looked to the floor, too afraid to make eye contact while slinking in and sitting down at her breakfast table...

"Well Happy New Year to you too!" His older Mother-in-law chirped noticing his quiet entrance, pointing out how he had come in without say anything, not even a hello or good morning...

"You didn't have to bring your bag down... Barbara and Keith won't be back until this afternoon so we have plenty of time... Tell, me? Did you sleep okay?" She asked...

"Uhh... H-Happy New Year Mother, and y-yes... I slept okay I guess, but I don't really remember going to bed to tell you the truth... I mean after everything, and then all of that Champagne, my memory is a little foggy" Adrian answered, telling his Mother-in-law that he didn't remember much, and quite embarrassingly so...

"Hmm... Yes we did celebrate alright... We nearly made it through two large bottles of bubbly, so I don't blame you... But you don't remember me helping you off with your stockings and taking your plug out before tucking you in? You were quite sweet and very polite... I must say, you're a happy drunk Adrian, you're very pliable and certainly not the type to go starting any fights now are you?"

"N-No Mother... I've never been in a fight... I... I don't like to argue, that's why Barb always has her way, I guess... It's because I'm a...a wimp... I'm just a c-cuckold sis-sissy"

Listening to him, Margaret was a little surprised with how down on himself Adrian was being, and so fast... Readily admitting his cuckold, sissy status... But as well, she knew this was difficult for him... However with the way he was talking? He sounded so defeated, sad even...

"Aww... Don't we sound all down in the dumps? Come on, it's not so bad... So what if you are what you say? A cuckold, and a sissy" She replied, being sure to say the words, reaffirming for him, just who he really is...

"At least you know and you can deal with it" she added, trying to snap him out of this little funk by showing the 'bright-side' of who he is... If there was one...

"Trust me, most people don't have a clue who they are, and because of it, they waste most of their lives denying everything and everyone... I mean at least with you Adrian... You know already... And you're only 30-yrs old? Oh baby... You are sooo far ahead of the game, you have no idea"

Lifting his head for the first time and looking to her, Adrian was curious now... What she was saying? Was it true?

"Are... Are you sure? Because I don't feel like that" He replied indeed unsure and not feeling ahead of the game as Margaret was saying... Not by any means...

"Baby once you let go? Once you stop playing the 'poor-me' card and really let go? Accepting who are and knowing your place? Oh Adrian... You have no idea how much easier and better you're life will become... And to think, you're so close... You've accepted most things like letting Barb go away with Keith, even condoning their having sex... You've let that happen, and let's not forget you and me? After last night, I think the two of us know where each of us stands... Wouldn't you agree?"

"Ye-yeah... I guess so" Adrian replied, feeling embarrassed again, remembering how they 'made-love' but as well... How she had him go down on her, licking her aged and aromatic pussy to orgasm not just the once, but twice throughout the evening. Sending her off for the second time with his "Oh so talented little tongue" at around 2am, he could hardly remember... Other than it being dark, damp and filled with her musky, mature, womanly secretions...

"You guess so? Oh Adrian dear... You know that won't do... After breakfast I'm afraid I might have to take you back over my knee for a refresher... Maybe spanking you again will pep up that woe-is-me attitude of yours hmm?" Margaret threatened but in a playful way this time, smiling as she watched Adrian's eyes grow wide with fear...

"N-No!... I... I uhh... I remember, but please Mother... You, you have to consider all of this is so new to me, and it's so...so hu-humiliating... But I am... I'm accepting who I am... Please! You have to believe me... It's just that sometimes it's harder to, to let go... Like now... I feel so sacred, and, and ashamed... I... I can't imagine what you and Barb will think of me from now on"

Seeing him struggle as he stuttered his way through, Margaret felt for him... But all the same she knew as well as Adrian did... They both knew there was no going back...

"We already know what we think of you Adrian... Barbara and myself" She began, her voice sounding calm and confidant...

"And to prove my point... And to drill it into that head of yours, I want you out of those pants... You'll spend the day with me in your panties... I was thinking, I usual wait until later in January to take my Christmas decorations down, but with you here to help me, we'll do it today... Besides, it will take your mind off of things until they come back"

Sighing and offering no real fight, Adrian knew better to agree with his Mother-in-law as she directed him to strip down, wanting him to revel himself, rather than to continue explaining things to him, so instead and until the time would come, she wanted him out of his trousers, showing them both who he really is...

Slipping out of the comfy fleece material pants he had on him that were more like a pair of dressy jogging bottoms, Adrian as casually as he could, but while blushing profusely he revealed himself to Margaret once again, showing her this time that he was wearing the teal green, pastel coloured panties she'd left out for him...

"Have you heard from Barb? I haven't and I'm afraid to text her... I didn't want to bother her" He asked thinking Margaret may have heard from her daughter, being as close as they were, and even more so with everything going on... He was worried about sending a message himself thinking he didn't want to bother Barb while she was away with Keith...

"No, it's still far too early... You know Barbara isn't an early riser, and I'm sure they're both well and truly hung over, if not exhausted from fucking themselves into the New Year" Margaret replied and making Adrian wince in the process... Listening to his Mother-in-law pretty much picking up from where she had left off, she wasn't afraid to be graphic. Mentioning Barb and Keith 'fucking' and probably doing so on purpose, just to embarrass him further...

"And look at you? Showing me your panties without any fuss... You see Adrian? I think you're accepting your new role a lot more than you're letting on" She added, commenting seeing him in his panties and the zip-up hoodie he had on over a plain white t-shirt.

"I... I guess you're right... I didn't even know, I was just doing what you told me" Adrian answered, agreeing but blushing all the same, thinking Margaret was right and that he did know who he was... Even if it was killing him...

"Well, very good... I know this is tough, but you are making great progress, and speaking of which... Out in the garage, you can start there by bringing in all of the boxes I keep my decorations in" Margaret instructed next, smiling and happy with the idea of Adrian accepting his place, wilfully taking off his pants and exposing himself in his light green cotton panties.

***

Working for the next few hours, both Margaret and Adrian had hardly noticed the time when suddenly her phone chimed with a text...

"Hi Mother! Sry' I dn't txt b4, was busy... We'r cls, be hm in 20 xoxo B"

Stopping and scanning her daughters message Margaret had to read the words twice, trying to decipher Barb's text-speak that drove the older woman crazy sometimes and making her wish cell phones or text messaging had never been invented.

Margaret thought cell phones made people lazy and case in point was her daughter, sending what looked like a coded spy message that in the end, all it really said was that they will be home in 20 minutes... Or so she gathered...

"Is that from Barb?" Adrian asked, curious but as well, feeling his stomach drop knowing he would have to deal with this next humiliation, he worried about Barb's coming home...

"Yes it is, and my! I don't know where the time has gone but you had better get dressed... She said they're close and will be here in a few minutes, so off you go... You can get your pants back on. Although I know Barbara would be happy to see you in your panties, however I'm not so sure about Keith"

Hearing they were due any minute, Adrian felt his heart rate climb as a cold chill run through him. He was scared and even afraid to look Barb in the eye. He didn't know what to expect and that was the worst part for him... Not knowing...

How would she see him? Would her heart have changed although she had sworn her love to him before leaving? Had Keith been able to sway her with his charms? Not to mention that big cock of his... The one that Adrian was still able to picture, outlined in his red trousers.

Or even about the reunion? Had he been talked about and made fun of by everyone as he had imagined? With a million and one horrible thoughts like these running through his head, however first and foremost, his biggest concern was being permitted to dress and after spending the day with Margaret bottomless in just his teal green panties, at her insistence, putting his pants back on, thus far it was his only relief...

15 or 20 minutes later...

"Hi..! We're back!" Barb beamed, sounding happy coming though her Mother's front door... However, and to everyone's surprise... She was alone...

"Hello Barbara... Welcome home" Margaret replied as Barb dropped her overnight bag, along with her smile... Seeing and hearing her Mother, where oddly she sounded no different than when she and Keith had left... She sounded cold and distant... Pissed off even...

"Oh, are we doing this again Mother?" She asked, catching the older woman's temperament as she stopped her at the front door...

"Come on, you can gave up the act, it's just me.... Keith went to his folks place, because believe it or not, he didn't want to face you and I'm starting to see why... You're not really mad are you?" Barb asked, wondering why her Mother was still keeping up this tense, pretending to be angry with her...

"Yes and no... That depends Barbara" Margaret replied, standing in her hallway, dressed casually in a blouse and long skirt, with her arms folded over her chest and indeed looking none too happy...

"It depends on what Mother?" Barb came back, asking and feeling guarded now...

"It depends on how you're going to treat your little husband in there who has been crying to me for the last twenty minutes believing you're going to think less of him after all of this"

"Why would I think less of him? Where is he? Adrian? Come out here" Barb answered as she called out to Adrian thinking all of this was a bit ridiculous and trying to side-step the woman who was stood there un-moving and blocking her way...

"Mother? What are you doing? Let me pass, please... Really, what's going on here?"

She asked feeling nervous now and like something was indeed wrong...

"I'm just trying to protect him" Margaret replied while remaining firm... "We've come a long way in the past 24hrs your little Adrian and I... Let's say that I've cracked him open and now that we've made this progress, I feel I owe it to him to make sure that you're not going to treat him any differently... Okay?"

"Yes... Yes of course... I've never thought bad of Adrian, you know that, and so does he... Just what did happen here last night? You sound so different, and defending him? I thought you were the one looking down on him Mother? Not me...That was Adrian's biggest worry about coming to stay with you.... He thought you hated him"

"Well dear, it's like I said... We've come to an understanding, and yes I do feel differently towards him... I mean, I am a woman after all, and I am entitled to change my mind"

"And I'm a woman too Mother, now come on" Barb replied, not really believing her Mother's argument... "Stop this and let me see him... I promise you I won't be mean or put him down... I know what he must be going through... We've talked about this a thousand times"

"That was then and this is now Barbara... I just want to be sure you feel the same as when you left... I want to know if having a dirty night away and fucking your former boyfriend has had an effect on you, or if you've changed your mind about Adrian... You have to understand my position"

"Wow! It sounds like you the two of you grew a lot closer than I did with Keith! Just what did you guys get up to here last night?"

Barb was feeling a little stunned as she stood there being berated by the older woman. Thinking at first she was still playing this game, but the longer it went on? The more she knew that this was real and that her Mother, for whatever reason, she was genuinely concerned for Adrian's well being.

Taking a second, and a deep breath while trying to processing this unexpected turn of events, Barb began to realize that not only was her Mother right, but she also understood why... Why she was protecting Adrian so fiercely...

"Okay I get it... I know why you're doing this, or I think I do anyway, and you're right... I'm sorry Mother I guess I've been avoiding this side of things, and I do feel guilty for going away... But can I see Adrian please? I want to take him home so that we can talk"

"Oh so you are going to break his heart even more? What are you going to do? Tell him that you're splitting up with him just because you've had a real man satisfy your urges? Is that it?" Margaret asked wanting to pressure Barb and test her resolve, her commitment to Adrian and her marriage...

"No! I'll do nothing of the sort Mother... And in fact... It's quite the opposite, thank you" Barb replied, sounding put out as Margaret smiled knowing she had struck a vein...