Mother May I...? Ch. 02

"Uhh! Ohh! Oh God" Adrian yelped back, surprised but also oddly relieved when feeling Margaret moving the big cock buried in his depths. It felt better than being made to stay still.

Fucking him in and out, it came to Adrian as a strange, unsettling relief...

"There, there sissy... Can you feel my big cock fucking that tight little ass of yours? Relax and you might actually enjoy it" she said to him leaning forward while pulling Adrian back, talking into his ear in more of a growl this time, no longing cooing softly or lulling him in...

"Uh... Oh, oh" he moaned unable to stay quiet as they both settled back and watched once again, seeing the young blond first spread out a handful of shave foam, coating and covering his entire groin, from his already shorn pubic mound, down over his soft penis and loose skinned ball sack, being touched after so long was causing Adrian to quiver without control...

"Stay still now... You don't want Denise to slip do you? We all know you're small but I don't think you want to lose what little you have" Margaret directed only half teasing as she halted her movements, keeping both herself and Adrian still as he remained stuffed full of her cock and watching...

Feeling the cool smoothness of the razor, Adrian did what he was told, fearing Denise might cut him as the older woman was suggesting, he went still with his breath held and his hips tilted forward in an automatic motion, seeing and feeling the girl's pink safety razor glide over his denuded, hairless mound did feel nice, if this slight pleasure was any consolation...

"There, that was easy!" Denise the young pixie-blond happily declared just two minutes later, having taken Adrian back to a smoother-than-smooth sheen with her razor and delicate a touch...

"I guess you have been taking care of yourself, down here huh? You did a really good job, even being caged, you didn't miss much" the girl added, remarking as she wiped him down leaving his pubis bare, slick and shiny. His scrunched up little ball sack held tight to his body looking even smaller, immature and ineffective...

"Very good... You know what to do next kitten" Margaret said then, first complimenting young Denise as the girl smiled with a knowing wink, hearing her Ma'am calling her 'kitten' in a sweet, sexual way as Adrian was left looking and wondering again about his Mother-in-law and her sudden interest in young girls.

However seated as he was atop the mature woman's lap with 7-hard inches of her strap-on buried deep inside of him, to say the least, young Adrian was otherwise distracted...

"Uhhh, ohhh!" He moaned moving his hips from side to side trying to find a spot of comfort, if one existed, yet Margaret of course, she saw things differently...

"Mmmm, yes... Press yourself down... Now you're going to learn what it feels like to be woman... To feel like Barbara taking all of Keith's big, thick cock fucking her the way she needs, the way your wife deserves"

Torturing Adrian again with her harsh words, feeling him move as he moaned, she was sure to mention Barb and Keith and how her ex-boyfriend is the one fucking his wife these days and not him...

How Keith with his big cock has taken over, more or less stealing his wife from him and fucking their days away on a beach somewhere in Florida...

"That's it... Now you're getting into it... Up and down, it's the only way I'm going to let you do this sissy-boy... You'll cum while fucking yourself on my big, hard cock or not at all... Ohhh yesss this is the only way for you... Take it... Take me and my c-cock! Ummmph!"

With her desires driving her intent and no longer able to hold back, Margaret began rolling her own hips harder and faster.

Perched forward again, seated at the edge of her wing-back chair she began taking Adrian with greater urgency, fucking him to the point where soon enough he was crying out with his feet leaving the ground, up in the air she had him held like a coat on a rack, hooked on her hard cock as he howled...

"Ohh! Oh God... Oh! M-Mother!...Uhhh! I mean M-Ma'am" Adrian railed, with his head going back, the air being repeatedly knocked from his lungs and with his vision in a blur Margaret continued fucking him, bouncing him on her knee...

"Now you can help Denise, take hold of his ankles and lift, lets open him up and really give him a good seeing too, hmmm?" She directed then, looking and telling Denise to help reposition Adrian as the girl did so, gladly taking a firm grasp of his ankles she raised each of his feet high up above his head...

"Oh there you go! Look at that!... Opening up for us just like a slutty little girl huh?" Denise the hard-bodied blond teased, holding his ankles as Adrian struggled to breath, bending his knees and gritting his teeth while being re-positioned, opened up while fully impaled, the change making everything feel all that much deeper and ten times more intense...

"Arrrrggg! Ohhh! Oh please, go s-slow" he begged not sounding all too convincing or like he wanted this to stop, but if anything Adrian was begging for her to go easy on him. More so saying he wanted Margaret to fuck him slowly, rather that to have her stop altogether...

"Do you like being fucked properly Adrian? This is what you wanted isn't it?" Margaret asked from over his shoulder and behind him, holding him firm at his chest with Denise keeping his legs up he was stretched to his maximum and left mumbling out a faint gurgling... "Yee-yessss"

"Ohhh, uhhh, Ma'am it feels so, uhhh... It's so big.... Oh! Uhhh" he gasped as Margaret continued fucking him at such a stark angle, using her wide, heavy hips and thrusting continually upwards, driving her 7-inch latex cock as deep as she could...

"I can feel it too Adrian, my cock is fucking you the way you want and it is good, very, very good... I'm fucking you the way you need... Mmmm yesss, sooo good" Margaret howled back in her own fevered excitement, rolling her hips into him and then away, matched with Adrian's movements together they were soon at a pace, fucking his ass while also grinding into her, casting her further, pushing the woman closer to the edge of cumming right along with him...

"Oh wow!" Denise exclaimed form her front row seat, enraptured with the sight... "This is awesome!" she called out... "But how come you're not hard Adrian? Where's your little stiffy gone? Don't you like it?" The younger girl, questioned sounding excited but seeing his un-caged, hairless, pink nub of flesh looking soft and squishy, wiggling and bobbling on it's own, the sight of him did leave her curious...

"Some boys are like this Denise... When they have a big one inside their sissy-pussies they go soft as a sign of respect to the man with a real cock, and I love it!" Margaret answered but went on...

"Losing your little boner when being fucked, it's a true sign that you are a sissy Adrian...Unnng... Stroke him Denise, help him... He's going to cum with my cock in him, even if his little dick is all soft useless!"

Answering Margaret felt a certain amount of pride, knowing what was going on after reading in her article about such things happening, submissives losing their erections while full of cock, and she was pleased to inform him so, further confirming Adrian's sissy-status and leaving him no room to argue as he panted and struggled, moaning and pleading all the way to his end...

"Uhhh! Ohh! Oh please, It's too much...Uhhh, oh God it's coming.. It... It's going to ha-happen... Uhhh!" He hollered as Margaret bellowed back..."Yes! Take it! Take my cock you worthless little man...Uhh... Uhh... Cum sissy-boy... Cum while I'm fucking you!"

Really throwing it to him, thrusting in an upward motion with her hips Margaret had the two of them bounding on her living room seat and landing with a thud, impaling Adrian hard and taking his breath away each time, bottoming out with the backs of his thighs slapping Margaret's with a loud, ringing clap...

"Ohhh yes! He's leaking like crazy, it's all over my hand" Denise shrilled in her excrement, seeing and feeling Adrian's thin, runny wet secretions beginning to flow out of him like a sugar maple tapped in late winter...

"Mmm, it so warm and wet... Cum Adrian... This is so awesome, let it ooze out of you... Don't be afraid, don't hold back"

Feeling Adrian's watery-warm cum weeping out of him in a long, slow stream rather than through a normal brought-on, hard and eruptive, alpha male ejaculation, Denise marvelled at the sight, no matter her experience and sexual knowledge as lesbian... Seeing men, or in Adrian's case, seeing a sissy cum was most certainly a treat...

"Oh it feel sooo g-g-gooood!" Adrian cried as Margaret kept up her end, thrusting herself into him with an upward arc as he came back down, meeting and fucking together, her dildo forcing and squeezing out his pent-up cum load in a thin, pearly-white ribbon.

Feeling the spasms of such rapturous, orgasmic delight ripping and tearing through him after being denied for so, so long... Cumming in any form left Adrian with his chest heaving and his head slung back, light headed he was about ready to faint in Margaret's arms...

"Are you getting it all Denise? Catch his cummies in your hand, that's it, now feed it to him... We all know how much you like the taste now don't we Adrian?" The older, dominant woman asked, first turning her attention back to Denise and where indeed she had Adrian's soft, cum-wet little package cupped in her hand.

Collecting his runny, yet still rather copious issue, two months of build up fucked out of him in such a humiliating and belittling way, riding his Mother-in-laws big strap-on while her lesbian lover collected and fed back to him everything he'd produced...

"Uhh, unngg-mmph" Adrian moaned accepting what he was being given as Denise fed her wet, glistening fingers to him, he opened with his tongue coming out and a lusty, pain filled knot in his face. With his eyes pressed shut, Adrian could both smell and taste his watery seed while lost in his sub-space, burning the shame of knowing who and what he is...

Sucking at her fingers he became overwhelmed with his own earthy, musty flavour, secretly savouring each and every drop... Adrian was a cum-sucking sissy and just then, no one knew it better then he did...

"Yes, that's a good boy, lick it all up... Mmmm, now there's is a sight to see... However watching you suck cock, that would be the real icing on the cake now wouldn't it?" Margaret commented as Adrian craned his neck some, subconsciously reaching and searching for Denise's sticky wet fingers and being noticed, he wasn't helping his cause any...

"Yes sissy-boy... Reach for it... You want it bad don't you? Barbara said she caught you sucking Keith's big dick while she was out... Tell me? Did he cum in your mouth that time? Or is it still just you licking your wife's pussy after he's filled her up and satisfied her needs?"

Keeping up the pressure while putting into Adrian's head the image of Keith cumming and filling his mouth while he sucked him, Margaret couldn't hold back her smile, or the fire already smouldering deep with her own loins. Being turned on by all of this, she could feel her arousal beginning to get the better of her...

"Uhh! N-no!" Adrian grunted with a surprised upswing to his voice, feeling Margaret extracting her strap-on from his no-longer so virginal back end at the same time he was trying to answer...

"No, he didn't... Not that time, Barb came in and stopped us" He added without really realizing what he was saying, delirious still and weak kneed Denise had him standing with her hands in his, holding him and supporting him as Margaret slipped out as well, righting herself while tugging and pulling all of her garments back into place...

"Oh so there were other times? Is that what you're saying?" She asked, pulling him up on his choice of words this time, implying that he has sucked Keith to completion at some time or another...

"W-well, yes and...and no... I've... I've cleaned him up, after... If that's what you want to know... I've only sucked him once before and, and when they're finished Barb tells me to... She says that when it's over for them, it's only the beginning for me"

Smiling and somewhat surprised, Margaret was none the less proud of her daughter Barbara. Hearing how she was taking control, telling Adrian when it was his turn, when he was needed, and for what? For clean-up duties... Using his mouth and his tongue to lick them both of their love making, removing while tasting and consuming the efforts of their passion, the combination of their sticky-wet fuck-juices...

"Yes, you've been very good to Barbara and Keith, and to me as well... So don't think I'm unappreciative for what you're doing, putting yourself at my mercy once again, as well as telling me all of your secrets" Margaret explained, being nice to him for once...

"I do appreciate you Adrian, you've opened up a whole new world to me and that can't go un-noticed" she commented, sounding the most sincere she had all day as Margaret stood with Adrian watching, seeing her first unfasten and then drop her glossy wet looking strap-on to the floor before stepping out of it altogether and casually strolling away...

"Be a dear and pick that up for me Denise" she said without looking back... "We'll leave our little sissy-boy as he is for the time being... Like a bottle of wine, we'll let him breath a while before putting his cork back in"

"Yes Ma'am!" Denise replied sounding up-beat once again and like she was in on something that Adrian wasn't... Or, that's the feeling he was given as the young blond looked to him briefly before letting her eyes dart away with a noticeable shyness. Whatever it was, he didn't like they way Margaret was taking, being cryptic again, speaking in terms he only ever half understood...

*****

"Come Adrian, sit here with me. Denise will be back in a minute or two so we have time to talk" Margaret said to him as Adrian watched Denise leave, but feeling nervous he knew that what ever was coming next, it's wasn't going to be any easier than what he'd already been put through...

"Are you going to cage me again? Right away?" He asked with reservation, fearful of being locked up so soon, and worse, not knowing how long he would have to go this time... When would his next stint of chastity come to it's end?

"Not right away, but soon... Don't worry about that right now my dear, come sit, here see? I have a towel all laid out for you, just so you don't make any messes on my couch" Margaret replied, patting the seat beside her as she moved over taking up residence on her living room sofa where there beside her was a towel spread out and ready.

However even seeing this made Adrian nervous, thinking again that more plans had been made for him without his knowledge...

Naked and unsure, he sat down beside the woman, taking the middle of the three seats with Margaret on his left...

"Now, there we go... Nice and comfy are we"? She asked as he nervously settled in, sitting back some but then feeling his Mother-in-law's arm coming around his shoulder and pulling him in, she kept Adrian close as she spoke and suddenly he didn't feel quite so comfy...

I'm alright, I, I guess" Adrian replied, lying some but not wanting to say...

"Well that's good, but tell me sweetie, are you comfortable at home theses days?" She asked as he turned his head looking to her with with mild confusion...

"What I mean is... How are you surviving with Keith living there in your two bedroom condo? Have you been kicked out of your own bed, or do you get to sleep with your wife, and her boyfriend?" She went on but Adrian he was no further ahead, only embarrassed hearing her refer to Keith as Barb's boyfriend, while still not getting what it was that she wanted...

"I... I sleep with them sometimes but, but I'm not sure what you want me to say" He replied this time admitting that he didn't know where Margaret was going with this line of questioning. But then listening to her, he didn't have to wait very much longer in finding out...

"So you do sleep with them sometimes, and tell me? When Barbara came home the other day and found you on your knees with Keith's big dick in your mouth... You say that was the only time but are you sure you're not fibbing to me?" She asked wanting to keep the idea of him sucking cock at the forefront in his mind by keeping the topic going,

"Yes, that was the only time... When we were alone" He replied, admitting with a shyness...

"Hmmm, yes as you keep saying but I just want to be sure... There were other occasions where you've found yourself knelling before him and uh, servicing Keith? Let's say?" Margaret asked pushing still and being sure to question all of Adrian's replies, hoping to trick him or even just keep him off balance, on his toes...

"N-no... I swear, I've only been with them a few times and it was just the once Barb caught us. But like I said before, that wasn't me... It was Keith... He tricked me, he said she wouldn't care, but I knew she would" Adrian said back, being emphatic in his defence with his excitement level going up he was anxious to get his side of the story out before Margaret was to believe otherwise...

"Yes, that's what I've heard... But my point dear sissy is that you did it anyway didn't you? You did what Keith told you to and sucked his dick for him, that part I can understand... But what I don't get is if you knew Barb would be upset? Why didn't you say no? Why didn't you just refused? That's the part I'm trying to understand... Why you said yes... That's what I want to know, and that my sweet sissy-son-in-law... That leads me to my next question" Margret continued dragging this out further...

"Wh-what's that?" Adrian stuttered sheepishly afraid to know as Margaret paused for a second longer, looking at him and waiting, delaying a bit longer just for the effect...

"Would you do it again? Or, more importantly... Would you do it for me? Would you suck a cock if I was the one telling you?" She inquired then, knowing Adrian would probably do it, but would he do it for her? That's what she wanted to know... Would Adrian suck a cock for Margaret as she watched on, smiling...

"I... I suppose if, if you wanted me to, b-but like with who? With Keith?" Adrian answered, saying yes, but again he was being cautious wanting to get it right, or say what he thought the woman wanted to hear...

He wasn't exactly sure just where it was Margaret seemed to be going, only how humiliating it was being asked such a thing... Would he suck a cock with his Mother-in-law watching, maybe even get herself off as he was doing it? Did she want to make herself cum at his expense?

"Don't worry about who... It's nice enough to know you would do it, just for me... That's very sweet of you Adrian but on top of this, I also want to know how you feel... Meaning, do you want to do it? Is it something you desires, something you crave? Or are you just saying you would because you know it will please me?"

Asking and sounding pleased but at the same time confusing Adrian and making him cringe when digging deeper, asking him the bigger question...

Did he want to suck cock? Or was he only doing it to please his wife Barb and now his Mother-in-law Margaret, as she was asking?

Unable to look her in the eye while feeling his shameful desire was about to be exposed, Adrian hesitated as he set his gaze lower to Margaret's feminine looking red painted toenails stretching thin the darkness of her black stockings as he cowered inside knowing he would.

Crossing that line wasn't just about pleasing Greg and now Keith, it was also about what Adrian wanted and how it made him feel, and where as much as anything, this was also about pleasing himself.