Barb's Boyfriend Ch. 09

"Aww what's the matter? Don't you want to wear the cute little nightie and stockings for me?" She teased as Adrian stuttered then, fearful of something else...

"W-well n-no... I don't really want to wear them, but I will...f-for you... But can I stand instead? It's just with this thing.... I mean, with my...my butt-plug in..." He replied, stuttering worse than ever while letting Margaret know about his bigger fear, or his bigger problem... Namely the 2-inch, heavy feeling, chrome butt-plug buried deep inside of him...

"Oh yes! Right! Ha-ha!" She laughed... "Well, I don't know about you Adrian? But I must be getting used to you being plugged because it's already slipped my mind! But anyway... Hold my hand, go slowly and you'll be fine... There you go... See? That wasn't so hard"

Listening but not agreeing because no, no Adrian wasn't getting used having his ass plugged, and the longer it went on, the more unbearable it was becoming...

"Now... As I was saying" Margaret continued as Adrian settled, looking up at her watching as she slipped off-white, or ecru coloured nylon stockings from the packaging...

"These stockings, they are a little different... You see... I was going to have you in a separate garter set, but then these little beauties were pointed out to me by my new friend Denise, and I thought... Oh yes... These are perfect for you" She went on, looking down to Adrian as he sat with the same struggling look on his face.

Half trying to adjust to the plug in his ass as he listened with his Mother-in-law of all people, about to put him in stockings...

"As you can see, the garters on these stockings, they're built right in and that's what makes them different and special... Don't they look sexy? I think they do... Now here, let's get them on you... I know the cream colour will look daring on you, they match perfect with your new nightie"

Not smiling or looking quite as happy as his Mother-in-law, Adrian chose to stay quiet again as she opened and unfolded the new pair of nylon tights, that were as she was saying, they were cream or off-white coloured and with an extra wide looking band of the same silky, see-through material attached at the top with four built-in garters connected to each long, sheer looking legs at the front and at the back.

They were novel and rather practical looking but still, they were for Adrian, and he wasn't sure if he was ready...

"Ahh! Ohh! Please... Not so f-fast!" He gasped then as Margaret forgetting again she had his one foot in her hand and up in the air, ready to start rolling the sheer nylons up each of his legs...

"Oops Sorry! I keep forgetting... Okay, well, I guess you have me, but don't you dare tell anyone you saw me like this" Margaret replied, realizing she would have to get down onto her knees in front of Adrian in order to help him into the stockings.

However, warning him ahead of time, she didn't want him getting an ideas as she switched places with him... Lowering herself to what should be his level... Yet Adrian, he didn't notice and nor did it bother him, knowing already where his place was and thinking that Margaret didn't need to feel as she did...

"It's... It's okay Mother... I know you're just trying to help... I don't see you that way... Like me... Not at all" He offered wanting to put her fears to rest but also, he was letting her know that he understood his place.

Leaning back some, resting with his arms out straight behind him, Adrian offered himself further, grunting and wincing but taking the hit, or the added pain in his ass, he lifted his foot for her, letting her slip first one, then the other rolled up stockings over his toes, and working the two back and forth... Soon enough she had the tight but cool and amazing feeling nylons half way up his legs...

"Ahh... They... They do feel nice M-Mother" Adrian said to her in a pleasure filled sigh that made Margaret smile as she had him stand. Rising up with her, his two hands placed in hers, she pulled him up before moving in behind him to slip her arms around his waist.

Taking up the top part of his nylon stockings in her fingers and working with him, she continued, moving and stretching the incredible, silky-soft feeling material up his bare, hairless upper thighs leaving him to tremble and falling helplessly into her arms.

Sighing ever still, Adrian was lost in the instant rapture found in such an everyday item as a pair of nylon stockings... Or they were an everyday item... Provided you were a woman, a real woman and not a submissive, feminized cuckold learning about and experiencing such wonders for the first time...

"See? I told you... I knew you would love them... Just get over the fact that you're wearing women's stockings and enjoy the feeling... I know what you're going through, all women do... Relax Adrian, I can tell that you like this, and here, see? Look and feel with me... I love how these have a cute little garter built right in, and doesn't it feel amazing too? All soft and silky against your skin?"

Cooing in his ear from behind him while holding and supporting his limp weight, Adrian was sent into a deep, body shaking tremor like he was near hypothermic and chattering hard as the incredible dainty, feminine feeling women's hosiery settled into place.

Smoothed up his legs and Margaret was right, the built in garters, they did look and feel amazing, the front panel, stretched out across his flat, hairless mid-riff like a vapour-thin belt, resting just above his naked and exposed pubic bone, he couldn't help but grow to his hardest, full, erect state...

All four hairless inched of him, left stone hard and twitching...

The nylons looked as sexy as they felt, as his stiff little dick was indicating... But as well, and with a sickening, quaking feeling in his stomach, he also knew that it was wrong... This was wrong, he wasn't meant to wear such things... Such wonderful, soft, and caressing things...

"Oh gosh Mother, they feel... They feel so good but, but I shouldn't... This... This isn't right" He sighed, fighting what he knew was a losing battle as she stayed with him, letting him drink in the sensation. Margaret let him connect with the experience...

"Now, now... Don't think that way, of course this is right... Right for you Adrian... You belong in panties and stockings, and who knows? You might even like trying on a dress some time... But for now, just relax, feel and enjoy...and here... Let's get you into you're nightie, hmm? I know that will help you too... Don't you love the soft pink colour? It's also 'you' Adrian, so come, lift your arms for me... There's a good little girly-man"

Stepping away momentarily, Margaret picked up the feathery light, short Chemise night gown and with Adrian in a fog, he turned offering no resistance, doing as she asked, lifting his arms and allowing her to slip the ultra light see through nightie over his head and letting it fluttering all around him, the dusty rose coloured chemise setting off another round of fireworks in his head, Adrian was hit with the same eerie but likeable feeling he had while being put into the equally sheer, feminine feeling stockings...

Being shot with this double barrel of femininity, it was almost too much sending Adrian's mind into a swirl of delights the likes of which he'd never experienced until now...

"Ohhh... Gosh Mother" He cried, cast further adrift, he felt like someone else...

"Th-this feels nice too... But it feels so wrong... I... I shouldn't be wearing stuff like this, but... I...I..." Adrian began, wanting to express how good the nightie and his stockings felt, but also in a very last bid of trying to rescue any of his male genetics, he held back...

Knowing already that if he said so, if he agreed completely, that would be it... Margaret, his Mother-in-law, she would see to it that from then on, this would be his life.

Adrian knew that after this he would be spending the remainder of his days dressed in panties, stocking and silky-see-through night gowns...

"But what Adrian? You like it?" Margaret teased as she stayed behind him, her two hands resting on his hips...

"Is that what you want to to say? It's okay... We know that you like being dressed as you are, and feeling as you do... But as well... It's okay if you're still having trouble finding the words... Remember, this is why I'm here... To coach you and guide you" she added, speaking for him now, saying what Adrian couldn't.

But as well, as she looked to him naked and hairless, looking so small and dainty, yet with one tell tale sign Adrian couldn't ignore.. And now, neither could Margaret...

"Hmmm" She hummed softly then as she let her fingers drift down and across his exposed mid-riff where undeniably and unmistakably, he couldn't lie... Not with his little pink-topped dick standing up and erect to his fullest. Yearning and hard, his meagre 4-inches stuck out from his naked, hairless pubic mound...

His little dick's erect betrayal was giving him away, letting Margaret know...

"Yes... It's okay... I can see for myself that you do like this Adrian my pet... In fact, judging from how stiff your 'little-guy' has become, I'm going to guess that's exactly what you're trying to say, that you like feeling girly and soft... It turns you on... Your little penis may be that... It may be little... But from how hard and excited he looks? You don't have to say anything Adrian, your little dickie-bird is telling me all on his own"

Burning up with the embarrassment, feeling so naked and exposed with his Mother-in-law, or just 'Mother' as she was insisting he call her, Adrian stood there listening again as his torment continued with her commenting and pointing out his stiff little dick...

"You do like this, don't you Adrian? Feeling girly and special?" She continued with her right hand and manicured nails drifting further, gliding and ticking her way across his shorn pubic mound, going down and daring to, she let her fingers slip in and around him, drawing forward and along the short length of his rigid shaft, the sensation and her feather-light touch, making him gasp and reel back, shrinking into her, the delight and the pleasure filling his mind in an explosion of paisley pattered, kaleidoscopic colours...

"Uhh... Oh M-Mother... P-please" He moaned as she continued, deliciously torturing him with her manicured fingertips, roaming and dancing, tickling his bare, hairless skin but staying away now... She only touched his stiff little dick the once, just to set him off, lure and temp him without going too far.

Margaret, knowing of his quick trigger, or of Adrian's status as a 'preemie' a 'cummer-too-sooner' she knew enough to stay way as she kept her long, sharp nails and fingers tips well back from his throbbing little member, fearing this come to an all too early conclusion.

Teasing him in other ways but then coming out with it, Margaret let slip her intentions...

"I know how excited you are and I am going to let you cum for me Adrian" She said over his shoulder as she held on with her hands moving higher, making him curl further into her as she attacked his little pebble sized nipples this time through his nightie. The sensation so strong, she had his eyes going wide as he gasped again, taken and surprised with this turn of events...

Hearing Margaret say that she was going to let him cum... It was nearly enough for him already...

"Yes... That's right Adrian, this is turning sexual... After all, why should Barb and Keith be the only ones having fun? And on New Years Eve no less" Margaret declared letting the frightened and certain overly stimulated Adrian know that she, his Mother-in-law... She was going to take this further... Much, much further...

"Oh...Oh gosh Mother.... Please... Don't get me wrong, I... I want to... Oh God, do I want to... But it, it's not right.... We, we shouldn't... Barb would get mad at me if we... If you and I... If we were to have s-sex... I... I mean, make...make love" Adrian cried back, saying he did want to take this all the way with her, but they couldn't...or they shouldn't... Thinking of Barb, he knew this was also wrong...

"Get mad?... No dear, I don't think Barbara will be angry or up-set... But I promise you, what we will be doing? It certainly won't be 'making love' and neither will you and I be having sex... Oh my Adrian, you are a very naive young man aren't you?" Margaret replied nearly laughing at his suggestion, or where he thought this might lead...

"No... You see dear, I have your wife's permission to do with you as I please, and yes, I did say that I will let you cum... But believe me... At no time will your little-guy be anywhere near my body" She added moving away from him she stood with her hands on her hips.

Looking to Adrian as he appeared heart broken, his face in a contorted knot, feeling like a fool and as well, looking like one too, or so he though... Standing there with his Mother-in-law after having dressed him in 'his' new nightie as well as the pair of admittedly amazing feeling nylon stockings...

"Now come along, let's head back down now that you're dressed for the evening... We still have a few things to take care of before we ring in the New Year, and yes... Letting you have some fun, or have your jollies as my own Mother used to say... But anyway, that aside, you cumming and draining those pent up little balls of yours? It is rather important, and not just for your sake either"

Feeling queasy and unsure, Adrian didn't know what to think, confused more than ever he wasn't even sure that he did want to cum, or have her 'let' him, and what her idea of this might just entail...

"Oh! Oh please Ma'am... Sorry... I... I mean Mother... Please, can we not go so fast? This plug, it's killing me and especially on the stairs... When can I take it out? Ohh! Oooff!" Adrian begged while moaning and grunting out his disdain, wanting Margaret to slow down on the stairs as well as wanting to know when he can have the damn thing out...

"Soon enough... It will help us later, at mid-night, when the clock strikes twelve, or not long after I promise... Now be good and come along... I want you as you were before please, down you go, kneeling at my side... You know your place Adrian" Margaret answered, but again she was being cryptic and vague about these New Years 'activities' she had planned...

"Ohh Ohh... Okay...Uhhh but please it's... It's not nice" He pled the one last time as he followed Margaret's instructions, struggling but sinking down to his place at her side as they came back into her living room

On his knees again and sitting as he was earlier with his legs folded under him and off to one side, trying as best he could to find some or any comfort.

Wearing her long gown, Margaret took up the material in her fingers at her hip, raising the wispy garment up and staying on her feet with Adrian there, looking up to her, his eyes full of wonder and pain she felt a special extra thrill with her stocking wrapped legs coming into view, but yet still, Adrian had no idea what she wanted, or what she was going to do...

"I told you I was going to let you cum... But first... We're going to do something different... Or something different for me, but maybe not for you... Because from what I also hear, and what I'm going to find out for myself is just how good you are at servicing my daughter... Your pretty, adulterous wife"

Declaring as she continued, Margaret raised her long flowing nightgown revealing her stocking covered legs, the black lace-topped nylons she'd slipped into when changing, and loving how they looked, making her feel all womanly and sexy, full of power and in control.

However hearing her, Adrian sat watching wide eyed and feeling like he shouldn't be looking at her like this again, seeing the sexy woman in his Mother-in-law coming out as this time, her night clothes... They were coming off...

Lifting the satin gown and keeping it bunched in her fingers, Margaret turned then, moving in front of an amazed and shocked looking Adrian, as she stood for a moment before sinking down, taking up her seat... Her 'throne'... Her favourite wing-back chair...

"Mother we...we shouldn't, or I mean, I shouldn't" Adrian cried, knowing already...

"You are a smart boy after all aren't you? Barbara has told me all about the one thing you are good at when it comes to pleasing a woman... And yes Adrian... Yes we should, and yes I want you to... Understand?" Margaret replied, echoing her same refrain of wanting him to acknowledge that he understood and would obey as she sat with her bare ass propped up near the edge of her cushion-topped perch.

With her gown gathered up all around her and her knees spread in a lewd fashion... Seeing her like this, it was all Adrian could do from looking away.

Keeping his eyes cast downward and yet still believing this was all so wrong, however reluctantly nodded his assent. His eyes unable to avoid seeing his Mother-in-law's dark, bushy looking, exposed pussy so close before him.

Close enough for his nose to catch her aroused, mature, womanly scent... Fragrant and pungent, it sent him reeling both in his own arousal and with the same shame filled angst...

"I know that you're good with that little tongue of yours, but Barbara said it was your devotion, your caring and wanting to please her... That's what makes you so good, and I hate to admit this to you, but... You Adrian, you will be my first... No one had ever been where you are right now and I want you to consider this an honour... Okay?"

Asking after telling Adrian that he would be Margaret's first and that if he understood her correctly, meaning that no-one, not even her husband had pleased her this way... No-one had ever gone down on her, giving her oral sex... It left him just as terrified as he was puzzled...

"You? You mean n-not even your hus-husband?" He asked fearful and feeling like he was indeed in over his head...

"No... No he hasn't and I don't feel ashamed or like I've missed out, and I certainly don't need any pity... Especially from you" Margaret replied sounding stern while trying to hide a little of her own embarrassment...

"But what I do want is to experience this, and you my little treasure... Our cuckold in the family... This is where your privilege comes in... Now, you're going to do this for me and then maybe, and I mean maybe, I'll let you have your fun"

Looking up to her and feeling himself shake, party due to where they were and how frightened he was, but also... Adrian's tremors and flush, fevered feelings, they were rooted elsewhere...

Being so close to Margaret, his Mother-in-law with her long, thick stocking covered thighs parted before him, her arousal and scent so evident and so strong, the pheromones of her womanhood, hitting him... It was like a trip wire, a trigger.

Smelling a woman, breathing in her aroma, her turned on pussy... It was automatic with Barb having trained him so well... Adrian, he knew what he had to do...

With his eyes closing and rolling upwards in their sockets, he took a deep, inward breath while moving his head in a gentle back and forth, letting her scent gather and collect in his nose as he sat up, moving slowly but soon centred in front of her with Margaret, smiling and watching, together they said nothing as Adrian leaned in placing a first, gentle kiss to her nylon covered inner thigh and leaving the older woman to sigh with her right hand coming up, running through his hair and settling at the back of his head...

"Mmm... Yes, that's nice Adrian my pet... Go slow, take your time and kiss me everywhere... Show me your respect and treat me the way you know how, my sweet, sweet boy" Margaret hummed then with her terse attitude shifting as her own stomach flipped, watching and feeling Adrian's lips touching and kissing her left thigh and leg, letting his tongue dart out, tentative at first, just to taste her skin...