Mother May I...? Ch. 02

Adrian knew that sucking cock lit something darker inside of him and that stepping into such dangerous territory again, blurring societies idea of what's right and what's wrong, it turned him on like nothing he had ever felt... Apart from saying it, His desire was more than enough to override any of his reservations...

Saying it out loud however, that was the hard part...

"I... I do like it Mother... Umm, I mean Ma'am... I liked doing it for Greg and now Keith too... It makes me feel like I belong, like it's my place, if that makes any sense? I like to please people and, and do what they tell me... I don't know why... I... I just do"

Answering and finding enough courage to make such a confession, Adrian was broken down a little further, telling his Mother-in-law that he liked pleasing people, even if that meant sucking cock...

"Aww... That's so sweet Adrian, hearing you say it, finally coming out and admitting who you are... A submissive beta who lives to please others...You see? It feels better doesn't it? Telling the truth" Margaret replied after listening and giving Adrian all the time he needed to spill his guts.

She knew it wasn't easy for him, but now that he had come out and said it, admitting he loved sucking cock... The door for her as they say, it was left wide open...

"I, I guess not b-but I'm still scared... I don't want to be gay. I know I'm not deep down... I know I like girls and women like, like you Ma'am... I still want to be here with you and with, with Denise too..."

"Shhh... Hush now little one... You don't need to be afraid, we know you're not gay, or not completely at least, and thank you as well Adrian... It's nice to know that I'm still desired, even if it is from a bisexual sissy-boy like you, I'll still take the compliment... However as I'm sure you know... You and I... We can never be 'together' in the traditional sense, if you know what I mean?" Margaret replied, trying to put some of Adrian's fear to rest while accepting his compliment. But on top of this she also wanted to be sure he understood the perimeters of their 'relationship' if that's what all of this could be called.... A relationship...

Using his words Margaret wanted to reassure Adrian of just how his involvement with woman would proceed from now on, and not just with Barb, but with all woman for that matter...

"Ye-yes... I know that Ma'am... Barb says that's pretty much over for us too... Making love the way we used to... She says that I'm better suited on my knees pleasing her with my tongue than I am with my, my..." Adrian answered or started to but faltering then he didn't want to say the new name Barb had started calling his locked up little penis...

"Your what darling? Come now, you can say it... What is my daughter calling your little dickie these days? Don't be afraid, tell me" Margaret said back, prodding him but already knowing through one of her many conversations about him with Barb...

"It's... It's my sissy-stick, Ma'am... That's what she calls it" he answered, feeling the pressure and stuttering as always, afraid and embarrassed to say...

"Umm-Hmmm... Yes, yes it is your little sissy-stick isn't it? I like that name and don't be afraid to use it. Remember you have nothing to hide here... Even your little sissy-stick as my Barbara has so aptly named that little nothing between your legs" Margaret said back, with her tone dropping once again but as well with her repeating herself when saying the name calling it his 'sissy-stick' over and over, she was working to only drive his humiliation deeper...

"But as I'm sure you know, all of our judgment of you has long been decided" she continued... "Now say it again and be proud this time... Tell me? What's the name? Is that your penis, or even dare I say it, your cock?" She asked in a harsher tease.

"Ye-yes... It's my sissy stick Ma'am, and I'm happy that it's free... Can I..? I mean, do you think I could cum one more time, before, you know? Before you lock me up, again?" He asked in hesitation but feeling brave and taking the chance, he thought of being permitted to cum a second time, before he's locked up for God knows how long.

Smiling, but more so to herself, Margaret was way ahead of her diminutive little son-in-law, already planning on draining his little balls utterly and completely, because cumming again for Adrian? After today, it wasn't something that was going to be happening for a very long time.

Sitting with him but saying nothing, not replying or reacting in any favourable way, Margaret left Adrian to hang in the tense silence. Time for him to stew while pretending to weigh her options as she watched him twitching in place, quivering beside her with a second bout of courage allowing him to ask again...

"You... You said I've been good and, and I won't give you any trouble putting me back into my cage... I just figured that you'll be locking me up even longer this time so it might be a good idea to do it when, when I'm empty... I... I guess you could say"

This time Margaret couldn't hold back her smile if she tried, hearing Adrian's reasons and sounding like a ventriloquist's dummy, saying the words as if she had her hand up his back that was making him talk, explaining why she should let him cum a second time after being told no and denied for as many months...

"You know Adrian dear, you do make a good argument, however let's not be too greedy, hmm?... We have plenty of time... I mean, you're not going anywhere are you?" She replied, speaking at last but taking some of the air out of his bubble Margaret dashed his hopes by not saying yes, but also, she didn't say no...

"N-no Ma'am, I... I guess I'm not going anywhere" he stuttered in reply, sounding downbeat and defeated.. "That's right you're not going anywhere, except maybe into my kitchen and what ever room I have you cleaning next," she added smiling and thinking further...

"When you were here last, at New Years, do you remember the fun we had taking down all of my Christmas decorations before you went in and made us lunch? Do you remember what you were wearing?" She quizzed as a renewed flush of embarrassment filled his cheeks with the memory coming back to him...

"My panties and a t-shirt, Ma'am" He said with a certain fear in his voice, looking to the floor once again as he sat naked, freshly fucked, punished and deflowered, his ass a red mess of angry red stripes and feeling the effects both inside, and out...

"That's right, and you'll do the same for us right now, you can wear a t-shirt but no panties this time... I have a pretty new apron for you to wear while you make us a nice light lunch...

Everything you'll need is in there and waiting, so away you go... Be a good boy and do as your told because I'm sure you know already what will happen if you don't"

"Ye-yes Ma'am," was all Adrian could reply as he rose, heading towards Margaret's kitchen with his head down, knowing he wanted to avoid any more of her humiliating punishment, or in this case just trying to keep his dominant Mother-in-law at bay for as long as he could...

*****

A few minutes later...

"So... Now that the little sissy is gone, have you had any word from his old boyfriend?" Margaret asked, turning as Denise came back in with a wicked smile on her face...

"Yes Ma'am! He sent me a message not to long ago... He was confused at first but once I explained a little more, he sounded quite happy, excited even" Denise the young pixie blond replied grinning from ear to ear along with her new lover, the woman she was 'teaching' how to be her dominant...

"Yes, I know that much, but what else have you told him? Do you think he would like to meet and perhaps re-ignite their old-flame?" Margaret asked harbouring the hopes of reintroducing Adrian to his old friend Greg, and their old ways, Adrian's old cock sucking ways...

"I haven't asked him yet, I didn't want to do anything without your permission, Ma'am" Denise replied as she changed her stance, dropping a hip and tilting her head and giving the older woman a submissively sexy look, batting her dark, heavily made-up eyes at her as she smiled...

"Well, look at you, showing me again how this works are you? Being my good little girl and doing what you're told... I do love that about you my pet. How well you're teaching me, but still smart enough to let me lead" Margaret said smiling back teasing her young lesbian lover...

"You have my permission... Contact him and ask him if he would like to see his little friend once again... I know I'd like that, for the two of them to find each other, however I'm not so sure about Adrian, so in that case we'll keep it secret. Maybe we can arrange some kind of surprise meeting for them... Oh God! Can you imagine the look on the little sissy's face?"

Happy with where she was and where it appeared things may be going the older, mature woman couldn't ignore the tingle growing in each of her thick, overly ripe nipples to coincide with the heavy, damp feeling of arousal filling her lower regions. The 50 year old Margaret, she could hardly wait for things to start happening as far as Adrian and his long lost friend were concerned.

But still, and knowing better, she kept herself in check. Controlling both her mind and her emotions, Margaret focused herself on their next task at hand, which would be putting Adrian into the new, tighter and smaller, all steel chastity cage Denise had been so thoughtful in choosing and briefly showing the devise to the older woman along with all of it's features including one interesting aspect that his current device did not have...

*****

30 minutes or so later...

"L-lunch is served, Ma'am" Adrian declared, or muttered is more like as he poked his head through the kitchen door and into the woman's living room where the two were back where they had been when Adrian had first arrived with Margaret sitting in her chair with Denise there at her side.

Yet stopping where he stood and with his jaw dropping, nearly hitting the floor, he could hardly believe what he was seeing, what he had walked in on...

"Uhhh, Oh yes... Mmm... Oh that's nice. Keep going... Oh you lick me so good!" He heard Margaret baying, calling out with her head going back and eyes closing as Adrian stood frozen in the doorway... Seeing what he was, yet instantly feeling like he shouldn't...

"Ahhh, oh and you!" Margaret called out a second time but surprising him even further, she was looking to Adrian as he realized, it was him she wanted...

"Come in and kneel beside her sissy-boy... I want you to watch and learn... See how a real girl pleases me... Although you are very good with that tongue of yours, Denise here has taught me that there is no comparison when it comes to who knows a woman's needs, and that of course, is another woman"

Listening but still a little shocked, Adrian followed his Mother-in-law's direction, obeying and scurrying in, not as naked as when he had left, but still feeling as such in a thin white t-shirt up top but with nothing on him down below... Nothing other than the sheer, pink and very see-through novelty-lingerie apron that had been provided for him to wear.

Exceptionally feminine, trimmed in delicate white lacing, the tiny waist-high garment looked more like a bedroom item than an actual apron giving him little to no protection and even less of a place to hide...

"Uhhh... Oh yes, my clit... Suck baby-girl... Mmmm, yessss" Margaret hissed as Denise zeroed in on the mature woman's thick, protruding knob of erect flesh, sucking at her hyper-sensitive clitoris, pulling inward with her lips, the young college girl had her older lover swooning as she fell back with her eyes rolling in her head...

"See what I'm doing sissy-boy? I'm sucking her fat clitty like it was a cock and we all know how much you LOVE sucking cock... Did you want to try?" Denise asked, questioning Adrian as he blushed on his knees beside her, afraid to answer

Sat back and biting his lip while squirming inside with his un-caged, freed-up little penis coming back to life, Adrian was all a quiver, full of nerves and feeling himself stiffen under his silky-sheer apron as he looked on...

"Yes! Do what she says sissy... I want the two of you to make me cum... Mmm... All of this has me so riled up, now get in there, suck my clitty like you suck Barbara's boyfriend's cock!"

Yearning and agreeing, Margaret took over telling Adrian what to do, how she wants him to help make her cum, sucking her fat, mature clit like a cock, like Keith's hard, 8-inches...

Saying nothing but feeling Denise's hand come up, cradling the back of his head and urging him forward Adrian groaned and gave in. Overwhelmed with his lusty wants taking over he opened his mouth and lips while eagerly taking in the woman's hard, heady tasting clit with his tongue coming out to curl around, stroke and tease her just the way he remembered how...

"Ohh fuck yesss sissy... Mmm... Oh I can't wait to see you suck a real cock.... Ohh fuck me don't stop.... Mmm, let me close my eyes and picture it, I'll cum so much better" Margaret moaned out as Adrian once again followed her orders to the letter, sucking hard at the woman's clit with a mouth full of her coarse pubes to go along with it, he worked his magic like a switch had gone off in his head.

The fear and reluctance dropping away his senses were a flood with Margaret's deep, womanly aroma, her arousal unmistakable, aiding and driving his efforts...

Sitting herself back and indeed, closing her eyes while imagining and seeing Adrian there on his knees but in her place it was Keith's big dick her effeminate little son-in-law had in his mouth. Seeing and feeling at the same time, it wasn't long before Adrian had Margaret close...

Denise however, remaining where she was and having learned a few of the older woman's likes, she slipped into Margaret's gaping pussy three of her fingers held in a bunch where then she began to fuck the woman in earnest.

Joining in with Adrian centring his attention higher, licking and sucking on the flailing woman's overly aroused clit that in the moment was threatening to go off like a firecracker... Exploding in an orgasmic series of hard, jolting spasms, cumming hard and rocking Margaret to her very core...

"Ohhhhh God yesssss! The two of you... Don't stop... Never.... Ohhh never fucking stoooop!" She hollered in a last gasp, cumming while bucking her hips upward, a handful of Adrian's hair clutched tight in her hand, grinding and fucking her wet mess of a pussy into his face...

"Ohh! Oh Jesus what you do to me? I... I can't believe I've waited this long... Uhhh, oh I've wasted half my life with one man when all the time I could have had this... Unnggg! Ahhh!" she wailed in her ecstasy... "Both of you... Now, up here... Come, I want to hold you, together"

Lost in the most delightful orgasmic glow with her emotions running ahead of her, she called to both Denise and Adrian, wanting them near where she can be held, feel close and be intimate.

Having this happen, allowing herself to be taken and turned into a wriggling mess of cumming, middle-age woman-flesh, dropping her guard and with it, part of her control she hadn't intended for things to progress as they had...

Laying with her for a time, the three all piled together in her living room chair, Margaret after catching her breath and enjoying her orgasmic after glow, she was soon to realize the need to catch herself and regain her position, take back what she had let go of while caught up in the moment...

"Right! Very good, now let's pull ourselves together, I want you both up... Adrian? Did you say that lunch was served?" She asked while having the two move, sending them up onto their feet...

"Ye-yes Ma'am, I'll... I'll bring in the serving tray, I'm sure the coffee should still be hot"

Feeling the mood change or Margaret's tone that is, Adrian thought it best for him to make himself scarce once again as he trotted away, wiping his pussy-wet chin while heading back into the kitchen to retrieve the tray full of coffee and sandwiches laid out earlier...

Before this unexpected little 'love-in' he'd just been put through... Being made to join Denise on her knees where together they had pleasured the older woman, licking and fucking her ripe, ready pussy to a thunderous orgasm...

"He's really quite cute isn't he? Denise asked as the two watched seeing Adrian disappear through the woman's kitchen door...

"When can we cage him again? I'm dying to try out the sounding rods before inserting his catheter... I love the medical range of chastity devises, and once you see the tube going in? I know you're going to love them too!" The young college girl added saying again how much she was looking forward to the next phase in Adrian's subjugation, which as she was describing, it involved a set of sounding rods and an insertable catheter being included with his new chastity cage...

"Yes, they do look quite interesting and you're right, I am excited to see how this works but as well, I'm more interested in how our little sissy-boy is going to react... Speaking if which, did you remember to bring one of those little pouches I came across in the on-line catalogue?"

"What was it called again? It looked to be quite an effective training tool if you ask me"

Replying, Margaret was intrigued with the idea of Adrian's new cage coming with a catheter, but as well there was another little item that had caught her eye... One she thought was quite clever and a rather handy little item to use when taming her already timidly scared little sissy for a son-in-law...

"Oh you mean the Glass-Purse? Yes, I have one, and in fact, here, look for yourself, it's in my bag with everything else... I brought a pink one like you asked, but be careful though, the inside will prickle your fingers if you're not careful!"

"Oh my! Are you sure it will be safe enough to put on him?" Margaret said back sounding somewhat concerned but still loving the idea of using such and eye-opening device on the submissive beta-cuck...

"No, it will be okay, the little shards will only cause damage if you drag them across the skin, but if they're simply pressed in, like when you pull the draw string closed? You'll get the same effect but without causing him any real harm" Denise explained... "It has more of a fibreglass feel, it's prickly and itchy, or so I've been told"

Saying the pink coloured velvet sack, or 'Glass-Purse' as it was known was safe to be slipped over Adrian's exposed little ball sack that once on him, and with the strings pulled tight the 'purse' lined with millions of microscopic glass shards would prickle and jab into the soft, tender skin of his already denuded ball sack and thus assuring his full attention, if not keeping him frozen in place, terrified to move an inch.

Thinking of the pain and discomfort such a nasty little piece of cloth could produce, the devilish idea had Margret feeling her nipples tingling anew with such naughty, lusty anticipation... Dying to try out this devise on Adrian, if anything just to watch him dance...

"Oh how lovely, you were able to find one in his colour, pink... All of the ones I found on line were black, but this is much more suited to our little sissy-boy, and it will go nicely with everything I have for him to wear... I think pink is going to be Adrian's colour!" The older dominant woman commented pleased the Glass-Purse would match with the rest of his sissy-maid outfit

The one she had let Denise choose from the racks of authentic fetish clothing at the sex-boutique... The new costume he would be put in and made to wear while serving his two new Mistresses...

"Yes, I thought you'd like that and here, have you seen his new cage up close?" Denise added with another bright smile, producing for Margaret the heavy feeling, all steel chastity cage Adrian was to be put into.