Mother May I...? Ch. 08

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"There you go bad girl, that should teach you a lesson but... Mmmm though... I still love this ass, stay right where you are, I'm not finished with you yet... Not by a long shot" Greg said to him ending one nightmare for Adrian, leaving him with a lave hot feeling ass before moving him on to the next, where once again Margaret stepped up providing his old friend and current tormentor with the very thing he needed...

Adrian's smaller, jewelled bottomed, acorn-sized butt-plug... Handing it to Greg with a smile while also offering him the tube of Astroglide body lube...

But then and stopping in front of Barb and without a word she also hand the girl a toy of her own, not a dildo, or a butt plug but a miniature, smaller, battery operated version of a Hitachi-wand, it was something Barb recognized but didn't own one, not as of yet...

"Oh yes! This is just the thing!"Greg chirped, pleased and again, seeing what Margaret had handed him, no longer surprised with the depths of this wonderfully-wicked woman's level of kink...

"How's that feel Adriana? Can you feel your Uncle Greg's finger in your tight little pussy?" He teased, turning his attention back to Adrian, or 'Adriana' and calling himself Uncle again as Adrian winced feeling his friends slippery lube-up finger touching and pushing into him.

Making him moan but not trying to get away, the cool gel touching his hot feeling skin, along with Greg's thick finger, sliding and pushing it's way in, he found himself wigging back almost inviting and wanting Greg to toy and finger fuck his tight little hole as he had before.

"Uhh yes...ye-yees Uncle G-Greg... Oh it feels good, please use more, more lube it feels nice" He sighed back, stuttering as his body trembled uncontrolled but deciding to join in and play along, Adrian said the name back, loving this pained or not, he had easily slipped into his sub-space once again and it felt so good this time, he was in no hurry to find his way out...

But then, Barb bursting out herself, overcome and on the verge of her first orgasm, she couldn't hold back seeing this all unfolding in front of her "Uhhh... Oh fu-uck don't stop, please don't fucking stop!" She groaned, nearing what she was sure would be a monumental if not life changing orgasm, but catching herself and realizing, she looked to Margaret who once again was scowling and giving her daughter that 'cut-eye's look with one of her eyebrows crooked in a disdainful arc, and seeing Barb cowered some, afraid almost she apologized and nearly begging, not to be kicked out...

"I'm... I'm sorry... I'll be... Uhh, oh God... I'll be q-quiet" she gasped saying she was sorry however doing so while still holding that big vibrating wand over her pussy and with her eyes going back, Barb chose to stifle her cries this time by biting her lip and groaning inwards...

"Unnnngggg" she cried and pulling at a nipple through her vapour thin blouse and riding her Hitachi and watching. Turned back from her Mother's icy stare she was in time to sees Greg with Adrian's tight pucker spread open, finger-lubed and ready to push the small acorn-sized butt-plug into him. It looked sexy as all fucking Hell from where she was sitting and edging her ever closer to cumming in what she hoped would only be the first of the night's many, strong and powerful Big-O's to come...

"Ooofff!" Adrian moaned out then feeling Greg press the small plug into him and keeping it there he pushed in further with his middle finger, rotating it around and making sure his little buddy could feel the thing to it's fullest...

"That should keep you open, or get you ready... Speaking of which, get back down there princess, you're not finished sucking this cock... You need to keep me hard don't you?" Greg said to him as he had Adrian off of his knee and back down with his freshly spanked and plugged little ass in the air, his friend's firm, large and wet looking 7-inch mast of a cock waving in front of him just dying to be sucked...

"Fuck yes, suck his cock Adrian.... Get him ready baby... Are you going to let him fuck you again? Unnngg, oh I'm dying to see that" Barb called out once more, caught up in what she was witnessing, her little man, about to be defiled and deflowered and wanting it to happen. She was loving the gay sex, but more than anything she loved that it was Adrian, living out his deepest, hidden desires, his long forgotten cravings and lust filled wants...

"Unnnggg, Mmm Unnggg" he gurgled back as he took Greg's stiff cock down to the bottom for a second time, wanting to anything he could to make him even harder if it were possible, sucking and tasting, while moaning and groaning, Adrian was hungry as he made his friend ready... Ready to fuck him in front of not only his Mother-in-law, but also, his wife...

"Unnhhhh... Ye-yes... Yes please... I... I want you to fuck me in front of them... Please, fuck me again Greg... Sir" Adrian cried, begging now as he pulled himself off of his friend's towering stiffness and stroking the big thing up and down, he couldn't wait any longer to feel the huge thing to split him open again...

"Let me up and kneel on the seat, come on get going... We want to give these ladies a show and speaking of which, why don't you ask your lovely wife here to take your plug out before she takes my cock in her hand and puts me inside you" Greg suggested, or ordered really, taking it upon himself to dial up the kink, wanting to humiliate Adrian if he could by having his wife be the one to put his cock into her husband, and to Greg, that was the ultimate...

Other than fucking her of course, but being who he was, and although not an impossibility, but for now he didn't see that happening... What he was doing at the moment, about to fuck the woman's husband a third time, Greg knew that fucking Adrian in front of her would be more than enough to satisfy all of his current wants, and his needs.

Shucking his tight jeans, piled up at his ankles and as he looked up, Greg was presented with Adrian as he wanted him... Kneeling up the sofa, half hanging over the back and with his ass in the air, waving it around and looking like he was begging...

Begging to be fucked...

With his heart beating fast and thinking of the two woman behind him, his wife Barb and his first Dominant, his Ma'am, Margaret... Adrian was pleased that they were both here and watching as he smiled to himself, happy knowing they were enjoying this and getting off as he was, feeling the sexual heat and the gravity of the situation, he was sure that like him, they too never wanted this to end...

This was where Adrian belonged all along, dressed and as sissy bitch and about to fucked like one...

"Ohh yes I wanna do that... I want to hold that big cock as you put in him" Adrian heard Barb say from behind him as her voice drew closer before feeling her touching and running her hands all over his taut, stretched out ass and even giving his little plug a wiggle of her own as she smiled leaning over wanting to talk to her sissy-boy's, whisper sweet everything into his ear...

"Mmmm I know you've wanted this forever Adrian and now you're gonna get it, You want me to watch him fuck you don't you baby? Come on tell me, tell your wife how much you want your boyfriend's cock... How you want be my cuckold but in reveres... That's right, instead of you watching me take a big one, now it's my turn... Now I'm going to watch you take your lovers stiff, hard, cock"

Toying with him while playing it up, Barb was as happy for Adrian as she was for herself... Loving what they were doing and indeed, Adrian was in a way making her his female-cuck where instead of her fucking someone else, he was the one about to be impaled and taken...

That's what made this so much better for Barb, and for Margaret as well... Their little sissy, he was learning to love taking cock but this time, he was doing it just for them...

"Ye-yes I want it Barb... Ohhh take my plug out and put him in... Please?" Adrian answered craning and trying to look over his shoulder but with his eyes closing shut as his head dropped into the crook of his neck when feeling Barb pulled his plug free.

Popping the small, silvery bobble out as his mouth fell open in a groaning sigh, Adrian was once again filled with that unsettling feeling of being vacated and suddenly, yet eerily wishing it back in a way he was never able to understand.

Each time this would happen, each time someone pulled something or anything out of his ass, all he wanted was for it to be put back in...

"Mmmm... I love feeling a big cock like this going in... Are you sure I can't temp you Greg? I'd love to go for a ride on this thing" Barb asked only half joking as Greg moving in, stepping up with his rampant erection there for Barb's hand to grasp as she wrapped her fingers around his thickness

Giving him a few soft strokes while biting her lip and feeling envious of Adrian with her own pussy on fire, Barb wanted a big cock like this inside of her, fucking her and making her cum...

"Yeah sorry baby, but this cock was meant for tight little asses, your hand feels nice and you can go down on if you want, getting me wet for your husband would be a sexy thing to do, don't you think?" Greg replied smiling back while flicking his eyebrows up and down like Groucho Marks and smiling just as big while giving Barb a suggestive nod as she slinked down smiling herself and showing her approval.

"Mmmm! I don't mind if I do!" She groaned back with her cock hungry mouth falling open and taking in Greg's hard, circumcised, perfect looking, 7-inch specimen of a real cock, sucking him up and down as she moaned further with Margaret surprisingly coming in behind her then, not realizing and shocking her some, she watched in her peripheral vision as her Mother went in, nuzzling her face into Greg's large, hairless ball, sack licking and sucking at him like a woman possessed...

"Oh gosh Mother! What are we doing?" Barb said, sounding flustered, not expecting things to go this way, from watching Greg to spank their little sissy's white skinned ass, but having it come to this... Double teaming her husband's 'boyfriend' with her own Mother in the real sense this time... Sucking his cock together like two sex starved harlots while above them Adrian lay waiting stretched out over the couch with his back arched and, looking over his shoulder not believing what he was seeing...

"We're enjoying ourselves, now let me have my fun... I haven't sucked a cock this big in ages, then we'll let him fuck this little sissy and do us all a favour by making him admit that he's gay" Mmmmph... Unnnggg" Margaret said back being direct but then not caring she had Greg's slick, dripping cock between her lips and over her tongue...

"Mmmph... Oh... Oh I do love sucking a big one and oh my God, these hairless balls!" She called out when going in a second time, gobbling Greg's big knob and sucking him hard in a rapid up and down motion before tearing herself away and offering him back to Barb, who without thinking she went at him as well... She sucked Greg's fullness as Adrian remained left out, moaning in a high pitched whine and wiggling his ass back at them, growing impatient as he waited his turn...

"What's the matter sissy-girl? Can't wait for me to get back into your faggot ass?" Greg asked being derisive while taking two of his fingers and sinking them back into Adrian twitching, quivering little hole and calling him a 'faggot' once again but using the word merely for the effect as Adrian had come to recognize. It was more a part of the show in Greg's dominance other than than his beaning mean like some redneck, right-wing asshole who just wants to hurt people.

But then and making him gasp with his head going back, filling his empty and vacant boy-pussy once more, Greg began twisting, finger-fucking Adrian and making him call out..."Oooh! Yeee-sss!" he hissed turning and burying his face into the couch cushions as he rolled his hips and pushed back, both loving and trying get away from the feeling, the pleasure and the pain...

"Oh yes ladies, you suck my cock almost as good as this one... I love having two mouths on me but quick, put me in, I wanna fuck this ass and cum inside him... We used a condom the first time but I took you bare-back in the shower didn't I sissy?"

Hearing him saying Greg wanted to fuck him, he reminded Adrian of how had taken him in the shower with no protection, sinking his cock into him bare-back and now he was going to do it again, forgoing the condom he wanted the feel of skin-on-skin as he pounded the little sissy in front of his relatives, his wife and her Mother, and for Greg just then he didn't things could get any better, be any hornier or down-right dirty...

"Unnng... Yessss... Please... t-take me any way you want... I want to feel you... I need it, I need all of you!" Adrian called out in desperation while hanging onto the back of the sofa and thrusting his ass onto Greg's two thick-cock-like fingers with his legs spread and his back arched in a slopping curve, thrusting himself back but wanting more, wanting once again to feel his friend's hard cock breaking it's way in, stretching him out and fucking him deep...

"Do it Barb, put him in me" Greg said looking down... "You heard him, he wants my cock he wants to be my faggy little sissy-boy, don't you Ade? Now that I'm back, I'm never going away... Tell them, tell them what you want!" he said with urgency and an intensity, pulling his two fingers from Adrian's loosened back ring and all but ordering Barb to take him and put him in...

"Oh yes! With pleasure" Barb replied sitting up on her knees and scooting herself forward she had Greg's rampant member back in her hand and aiming his red, puffed out cock head at her little sissy-husbands back entrance ready to put him in...

"Ohhh that looks so sexy" she moaned then letting the big-bulb of Greg's cock-head sit there a second longer, teasing and enticing Adrian as she circled his tight looking ring a few times and watched as he pushed back on his own, wiggling his tight little tushy at her, just as ready to feel his friend's cock going in and fucking him as Barb and Margaret were eager to watch...

"Oh please... Stop teasing me and put that thing in me....Unnnggg, Barb I'm begging you, I want him to fuck me... With you w-watching... Ahhh! Ohhh!" Adrian howled. begging as Barb giving him what he wanted, what they all wanted, she pushed the big mushroom cap of Greg's hard cock into her husband's pink, pliable anus and making him call out as the bigger man leaned in with her, pushing more of his long, thick pole into his little buddy's ass with his hands on his hips he sank himself in further...

"Unnngggg!" Greg grunted, feeling Adrian's tight, elastic sphincter surrounding and grabbing onto him as he went in as far as he could, hitting bottom his thighs coming to a rest against the backs of Adrian's as he held himself there, letting him adjust, letting the eye-watering, blinding while pain wash through not only Adrian's body but through him as well, through his brain, his psyche, his entire being...

"Unnnnnnggggggg" Adrian moaned back...

Trying to breath yet feeling like he was wrapped in a Boa constrictor's coil he was so full of Greg's gloriously hard cock that in the initial minute he could neither inhale or exhale, left gasping in short stunted huffs with his head going back and eyes popping open, Greg laid into him then, taking him at his hips, he began to fuck his cock into his little buddy, as he continued to moan and cry through every breath, matched with the in and out, slowly building in rhythm, momentum and speed.

*****

With Greg sawing his way in and out of Adrian's ass a hushed concentrated silence had fallen over the room with Margaret and Barb having returned to their seat but watched on with lip-biting wrapped intent, holding hands even, each squeezing the other harder the longer this went on...

Until suddenly the spell was broken, like hear a twig snapping in the forest, suddenly their attention was turned...

"Hey! What the hell is going on here?"

They all heard as the four heads came up to see Keith standing there in the entrance to Margaret's living room, slack jawed and too stunned to imagine... He couldn't believe what he was seeing...

"Keith!" Barb hollered then as she rose up, dropping her big vibrator wand and practically running she grabbed him and dragging him in, pulling him closer, still amped up and lost in her own sexual frenzy that had a very dirty, kinky idea suddenly coming to her...

One that had her smiling as they neared the couch where Adrian was slung over it's back and looking like a rag-doll with Greg behind him, growling and fucking his little sissy-friend as Keith gawked, too stunned to be repulsed or much of anything else...

"Unnng, Unnng, Unnng" they were both grunting and groaning out as Barb neared with Keith in hand and saying to him "You knew this was going to happen with these two, don't look so surprised baby, come, come closer" she bayed, luring her wide-eyed ex Keith ever nearer as he looked on but letting his eyes dart away not sure if he should seeing what he was, however and utterly distracted what he hadn't noticed was Barb, pulling the string to his jogging sweats and pushing them down, off of his hips...

"Wh-what are you doing? I don't want to be involved... I'm... I'm not like them" he complained not only blown away with this uber-gay and somewhat incestual sex scene he'd walked in on, his girlfriend and her Mother there as well, watching and openly playing with themselves.

But now with Barb apparently wanting him to join in and participate? It was all a little too much for Keith to take in after literally having just walked in...

Seeing Margaret there, this woman he's known all of his life and grew up next to, watching the mature 'Mom' running a slimline dildo in and out of her wet, ripe pussy and Barb not much different down on her knees and tugging his pants off along with his shoes and his underwear all while smiling as he looked on, not believing what she wanted him to do...

"Mmmm! Adriana! Look what I have for you" she chimed then sounding as happy as she looked, pulling Keith closer with Adrian's head coming up, hearing her calling him the female version of his name...

Slung over the top part of the couch at dick-level and seeing Keith's semi-hard familiar looking hunk of man-meat being waved under his nose, and where Adrian, having fallen once again into his groggy, sleepy, sub-space world, having Greg fucking him so deep, so hard and sooo fucking good, without saying a word, and with no complaint or apprehension he craned his neck forward while opening his mouth willing to accept Keith's ever growing member...

"Oh fuck me!" He called out feeling the eager sissy mouthing and sucking at his rising erection, taking him in with his lips cresting over the crown of his big, circumcised head and licking him from underneath as he shuddered in a deep breath knowing it was no use, the little sissy's mouth felt too good and this...this was happening...

"Alright, okay... Fuck me! I wasn't expecting this... I only went for a run after visiting my folk but Jesus! I guess if I can't beat-em' I might as well join-em'..." he said giving in as he stepped closer with Adrian so willingly taking him in, Keith gave in himself, getting over any notions of this being a gay-three way when in reality he had been here before...

Maybe not with Greg there and behind Adrian fucking him senseless but with his stiffening dick in the little guys mouth, this part wasn't new feeling how good Adrian was at sucking cock he sighed one last time, dropping any reservations as he reached up, taking the made-up girly-boy's head in his hand and began fucking him from this in and doing what he said he said... Keith joined in...