Mother May I...? Ch. 04

Agreeing but wanting to be nice, Denise didn't say anything in response other than to crinkle her nose while giving her head a soft, telling shake.

Saying yes, she could see it too, she knew as well as Adrian... He wasn't a man at all and meeting this girl, this whoever she was he was seeing in front of him, he went quiet again with the weight of such an awakening as this bearing down on him...

"So... Can you tell me more about this milking thing?" he asked then without looking away, keeping his eyes fixed on his own, the dark made-up eyes looking back at him through the mirror and surprised, seeing and hearing him appearing to be moving on, Denise went with him, moving on as well, she answered his question...

"Oh, uhh okay" she replied, taken back with this change in direction, but still she was more than willing to tell him...

"Milking is when you're sperm, or cum is extracted from you... Don't you know?" She asked while explaining and a little surprised with how naive Adrian was about some things, and with male-milking apparently being one of them...

"Not really, Barb doesn't like it when I look at stuff like that on the internet, like porn, and I feel guilty if I do so I just stay away... But how does that happen? How do you get it out I mean? Am I let out of my cage?" Adrian asked hopeful of being let out but also admitting he didn't know about such things, what with Barb all but forbidding him from looking at porn he was left on the outside about these things, and certainly too afraid to look in...

"No, unfortunately you'll stay locked up during you milkings... That's the whole point of it, extracting your build up without letting you out or having an orgasm" Denise explained further but now she wasn't so sure either, again with Adrian not being in the know when it came to this stuff...

"So Barb never milked you during your first lock-up?" She asked sounding surprised...

"No Barb didn't do anything when I was caged the first time... Everyone said I had to wait until today" he answered, telling Denise that he had been denied the entire two months and that he hadn't cum since New Years Eve when he was last with Margaret, or "Ma'am" as they had both been instructed to call their older, dominant Matriarch...

"Wow! The entire time huh?" Denise said back, surprised again... "That must have been hard for you, but It was probably a good thing if you think about it... Having been denied for two months the first time will make this next six fly by" she reasoned, telling Adrian his first two month stint would make this next and much longer six-month stretch seem easier...

However Adrian, he wasn't so convinced...

"Yeah right... I don't think anything is going to 'fly by'... This next six-months is going to feel like an eternity" he came back with, adding a note of sarcasm...

"Hmmm... Maybe?" Denise replied, agreeing in a way... "But that's up to you" she added as Adrian turned with a confused look on his face...

"Remember? Ma'am said she might let you out if you're good and since she has both of your new keys, you'll have to come back to here if want out at the end, never mind in the middle... Plus I think she's going to be in charge of your milkings and even your sissy-gasms" Denise let him know but hearing her Adrian was left even more confused...

"A... A sissy-what?" He repeated feeling a new spike of fear rising from within, having an idea what she was talking about, even if the term was new to him... Adding it up himself putting sissy and orgasm together, that much he could manage on his own, but still he didn't feel any better, also figuring it was something else that he wasn't going to like...

"Mmmm... Oh you're gonna love sissy-gasms" Denise chirped happily which of course had Adrian's guard going up even further... Anytime any of these woman were being overly happy, as he was learning, this wasn't always a good sign... For him...

"It's when you cum from having your prostate stimulated, but at no time is your little dickie involved... It's sort of like milking where it does the same thing but with a sissy-gasm, it will feel kind of like you're having a real orgasm" she explained, telling Adrian what would be involved, what would happen during these milkings he would have to endure throughout the entirety of his second bout of being locked up... During the next six-months...

He would be cumming, but only through milkings and being permitted these 'sissy-gasms'...

"Okay gorgeous, that's about all I can do with your make-up, and I'm kind of jealous, you're hot as hell for a guy who's only trying to be a girl... But anyway, let's finish getting you dressed and see how much more that turns you into the real thing"

Moving from one embarrassment to another, Adrian found himself back on his feet with Denise holding his hand and this time she led him towards the bed where she had waiting for him was the dress or maids outfit he would be wearing for the duration of his stay...

"Ma'am let me choose this for you... I found it in the boutique and put it away thinking of you... I'd only just met Margaret and your stunning wife Barbara the day before... I don't know what it was. but something told me I'd be putting this on you one day, and sure enough, here we are! Isn't that freaky?" She asked while smiling and holding up his outfit...

"Oh gosh Miss Denise" Adrian gushed, embarrassed seeing what she had, but feeling right in calling her 'Miss' for some reason. It gave her an authority over him that he was sure the girl liked, because she had said so, commenting the first time he had called her 'Miss'...

"This... This is a maids costume?" He gasped in question seeing just how feminine his new clothes would be... "Haven't you dressed me up in too much pink already?" He asked, surprised with the short dresses' simmering pink colour. This, and to go along with the thin white pipping laid out in a diamond pattern sort of matching his stockings but for some reason, Adrian had just assumed they would be dressing him in black, like any regular maid...

"Everyone is determined to make me look like a girl these days" He commented as he reached out taking from Denise the very short looking, lacy pink skirt and bib-top combo.

With wide shoulder straps lined with more of the pipping, yet looking and upon closer examination, Adrian was soon to realize that the front part of the skirt, it looked to be missing. The lace-trimmed pleats were much shorter in the front than at the back...

"Yes! That's exactly what we're going to do... You're going to be our pretty little sissy-maid for the next two weeks, but don't worry... I don't think they want you to transition full-time... This is just to give you a good taste of what it's all about... Being a girl that is" Denise replied before going on and saying something she probably shouldn't...

Dropping more hints that had Adrian's eyebrows going up, along with his level of fear...

"There is something else though... Something we're working on that will definitely make you feel like one of us" she said to him, blurting it out without really thinking...

"What's that suppose to mean?" Adrian wondered, adding... "I don't like it when you guys keep secrets, only telling me things after it's too late... It scares me more than wanting to wear th-this"

Carrying on, first letting Denise know that he didn't like being kept in the dark, but then stuttering while holding up the outfit on it's hanger, Adrian was admitted his want of wearing the pink little costume. But that too scared the hell out of him, and especially so once he had it on...

"Why is it so short in the front? You can see everything, and, uhh... I can't even hide my cage" he questioned looking down and seeing right away how the skirt material had been cut much higher in the front that left Adrian's shiny new chastity cage on display and with the bottoms of his tight little ass cheeks on view in the back...

"Yes, that's what Ma'am liked about it most... While you're cleaning and cooking for us she wants to see your panties and your cage" Denise answered, but Adrian, standing there embarrassed looking down at himself he had to wonder why...

Why Margaret wanted to keep him exposed like this with the lacy part of his skirt sitting daintily above his pubic line, yet out back, his red spanked, recovering little ass was covered, and just barely at that...

"B-but why? Why does she want me umm, 'out-there'? I'll be mortified if someone were to sees me" He complained, working himself up again...

"Well that's the point isn't it? She's doing it so that you stay that way, embarrassed, or mortified as you say it" Denise replied to which Adrian frowned...

"You can't say you don't like that part as well... It's in all sissies to feel some shame and humiliation... That's what gets you off, having people look at gawk at you, and embarrass you for looking this way. Wearing things like this cute little uniform, which does look great on you by the way, and don't deny it, I know how you feel inside right now wearing that"

"H-how? How do I feel?" Adrian questioned, wanting to be believe what she was saying, but still he needed to hear more...

"You feel like you want to run away and cry, but you also want to stay and play more of these games... Like us all Adrian, sissies also crave attention and yours just happens to come from being exposed and humiliated... You like being made the centre of attention, but for all the wrong reasons"

Knowing what she was saying, Adrian felt bad all of a sudden, like he'd been caught in a lie... A lie about himself...

"Ye-yes... You're right, half the time I do want to run away and cry but, but I also like it in a weird, strange way... Stuff like this, being dressed up and even with Barb going with Keith again, for some reason I want her to be with him, but at the same time it really hurts and makes me wonder what's wrong with me"

"There's nothing wrong with you Adrian... You're a masochist and that's why you feel like you do when Keith takes your wife, and it more than likely has to do with your past... That's where this all began, with something big that may have happened, and even if you have repressed the memory? It's still there playing in the background, haunting you in a way"

"You... You think this has to do with Greg and how I let him talking me into doing, umm... Into doing 'that' for him?" Adrian asked fearful but also thinking this may have been the point when things changed, yet to his surprise, Denise with her college education... She suggested otherwise...

"Yeah, that could have been it, but think about it Adrian, he led you into doing 'that' rather easily don't you think?" She asked as Adrian looked her in question...

"I mean, you could have said no and just left... You could have walked away, but you didn't, did you?" She continued, getting it right...

"Something inside of you had you staying and agreeing to suck your friend's dick for him"

Taking this further yet Adrian, he was at a loss, unable conjure up any prior event in his life that made him the docile, lead-able type...

"I can't think of anything that happened before I uhh, started doing that for Greg" he replied as Denise looked to him with quizzical tilt of her head thinking she knew already...

"There... Did hear what you just said?" She asked as Adrian looked to her, surprised...

"N-no... What did I just say?" He replied, questioning...

"You said when you started doing that 'for' Greg" Denise repeated as Adrian stared back blankly...

"S-so?" He stuttered in question...

"So, dummy... If you listen, it's right there... You said, before you started doing it 'for' him, meaning you were doing it for his pleasure... You knew that he liked having you suck his dick so you did it for him" Denise hypothesized, picking apart Adrian's usage of words. How he phrased things, it was very telling...

"Tell me, the second time it happened, did he have to coerce you then? Did he have to goad you into it?, or shame you in some way?" She continued, asking as Adrian thought, trying to piece together what it was she was saying...

"N-no.. Not really, or, or not that I can remember" He stuttered back sounding nervous...

"We... We were in his car the second time it happened. We were parked in his drive way, it was really late, we had been out delivering pizzas all night and it was like 3am or something"

Beginning to recalling the night, Adrian did what he could to tell Denise the story of how he had sucked Greg's cock a second time...

*****

In Greg's car...

"Boy it sure is quiet at this time of night huh?" Adrian commented after Greg had pulled in and shut off the car and taking the stereo with it, the two friends were left in the eerie, early morning silence...

"Yeah you can't even hear the crickets anymore, guess they've gone to bed" Greg replied as they sat making small talk, yet both were feeling something else... No matter the late hour, neither wanted the night to end. It was like they both knew this wasn't over, or more so they weren't finished...

"I sometimes wake up around this time dying to take a leak, but when I get to the bathroom I'm too stiff to go... That ever happen to you?" He asked this time while yawning and stretching his arms out in front of him with his hands clasped together, his wrist resting on top of the steering wheel, that's when Adrian glanced down and saw it... That was when he spied the bulge in his older friend's tight Levi's.

With his legs going out at the same time, Greg sat in the drivers seat stretching like he was tired as his hips rose he stayed this way for a moment leaving Adrian to think that maybe he was doing it on purpose. Thrusting his pelvis upwards in an effort to show his younger friend what he had, what was waiting for him.

Greg was smiling as Adrian's eyes came up making him blush feeling like he'd been caught looking, but then not really noticing at first, he soon felt an added chill running through him as his older friend's right hand came up sliding in behind Adrian's head and neck, urging him forward with slight pressure while asking in a quieter voice... "You want to try it again?"

Hearing him and feeling like he was in some sort of trance, but understanding what Greg meant, what he wanted him to do, Adrian nodded as he sank down in his seat with his stomach to follow. Sinking with more of that edgy, excitedly-scared energy rushing through him, knowing what he was going to do... What line he was about to cross...

"There you go, get my jeans open" Greg said to him still in a hushed tone, coaching while keeping a firm, suggestive hold at the back of Adrian's neck and giving him the impression where once again, like last time... He wasn't so much as being given the choice, but rather Greg was willing him to do it, putting in his head the idea that it was okay.

Still afraid, but with continual bouts of this shame-fill desire hitting him, Adrian knew that he wanted this, that he wanted to please his friend this way as he reached over undoing Greg's top button before pulling his zipper down, then surprising him some and like he was ready for it Greg sat up, raising his ass from the car seat and in what seemed like a flash, he had both is jeans and underwear pushed down to his ankles...

"You liked it last time" he said to him as Adrian reached out and took him in hand, feeling the warmth and stiffness of his friend's bigger, thickening, growing cock, a real cock... It made him shiver as Greg went on, telling Adrian how things were going to be with his acceptance, his wanting to suck his cock for him a second time...

"You even let me go off in your mouth, and so now that we're over that hump let's say... Why don't we make this a regular thing, huh? But remember, no-one can ever find out, right?" He said or directed, not suggesting but more so telling Adrian this was how things were going to be...

Greg wanted him to do this for him on regular basis and they were going to keep things quiet.

"Ye-yeah, I won't tell anyone, I promise" Adrian replied near enough now he was able to smell the musty, male aroma wafting up from the dark forest of his friend's wiry feeling pubes. The pheromones hitting him along with the rigid yet supple feel of having a stiff cock in his hand.

It was making Adrian want this even more, and going along with what Greg was saying, telling him how things were going to change between them, that was the moment Adrian also felt himself changing.

Hearing Greg say he wanted more, it was like the impressionable, younger guy had been given permission. He was telling Adrian it was okay to feel this way. He was allowed to have these cravings and could feel his friend driving them deeper into him as he spoke... Driven into Adrian's psyche, into his being...

Adrian was also in agreement of keeping this to themselves... That part he had not trouble with because after all, he was the one doing it... He was the one sucking cock, and as it stood, at no time would Greg ever reciprocate.

It was believed or simply implied from the start that this wouldn't be a two way street, and with that, knowing he was about to become his friend's little cock sucker buddy, there was no way Adrian wanted this getting out...

"Oh yeah, that's it buddy... See you're learning already, use your lips and tongue just like last time, get me wet first... Mmm, that feels good" Greg sighed then as Adrian let himself go, moving on his own now, he lowered himself the rest of the way, tilting his head and parting his lips he found himself in contact with the supple-hardness of his older friend's big cock for a second time in so many weeks.

The sensation and remembering, to Adrian it was like taking another hit on some kind of drug he'd only had once before but didn't know how much he missed... Not until now, until he was here again and doing it, sucking his friend's big cock, the taste and feel of the thick shaft on his lips, it was enough to seal Adrian's fate... He wanted this just as bad... He wanted to be his older, bigger friend's dirty little secret...

Adrian wanted to be Greg's private cocksucker...

"Uhhh... Fuck yeah, take me... Uhhh I've been wanting you to do this again man, that's it, yeah, go down... Oh fuck your mouth feels so good, suck that cock Ade" Greg moaned sounding more intense and like he wasn't in control. The feel of Adrian's mouth closing over him and moving down, the incredible feeling coinciding with the taboo element involved, it had him to the point of cumming, and far too soon...

Much sooner than he'd like...

"Mmmm, Mmmph" Adrian moaned back in trying to signal his approval, yet showing Greg in another way he proved his worth using his mouth with a new-found passion, a desire that out weighed his lack of experience...

"Oh fuck, you're so good... Yes, go up and down... I like that best when I can feel you lips on all of me, right down to the bottom and then back up... Unnnggg... Sweet Jesus! You swear this is only your second time?"

Grunting with approval Greg was impressed with Adrian's efforts and could tell right away that he had it right, Adrian loved this just as much as he did and this was indeed going to be a regular thing for the two of them...

Having Adrian suck his cock for him again and also having him agree to becoming his discrete little blow-job-buddy also confirmed something Greg had know about himself for a while. But like most young men making the discovery, there was denial, and lots of it...

"You can cum in my mouth, I want you to, I.. I didn't mind last time" Adrian muttered, being quiet himself while also feeling brave in saying Greg could cum in his mouth as he pulled himself off of his friend's spitty-wet member long enough to take a breath, momentarily switching back to stroking his hardness. Greg's hard cock, it felt like a warm, fleshy-wet iron bar in his hand...