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Chapter 49
by Conan The Librarian
How do you answer?
Stay quiet, be a good and obedient husband (Lily's Dark Ending)
"I... Lily knows what is best for me."
"I didn't ask you that." She answers, her eyes frowning just a bit.
"Of course... I'm sorry... I'll like to be with you." She seems pleased by that. She smiles with her lips, but not with her eyes. For a moment you feel bad about her, feeling that you should be more assertive in expressing your feelings and your love, but then she kisses you and it all feels fine. The doubts are quickly forgotten.
It is a discrete and short wedding, with not many guests and expensive and refined food, much in Evelyn's taste. Lily choses the place and your weeding dress: A traditional white that looks so wonderful, making you feel like a prince from a fairy tale. Evelyn looks so radiant at the altar when you walk up to her, so beautiful when she says "yes", you dance together under the sound of corny songs, and the scent of flowers and apple trees and for a moment you think this could all end well. But just the next day, in your honeymoon, the first problem arises.
"Why did you tell her she could come?" She asks you in your private suite. Her dress half undone.
"S... She said that... She needs to make sure I drink my milk... And that..."
"Mark, I don't mind sharing you. I really don't..." She says in a conciliatory tone.
"Sharing? What do you mean?" That is such a silly word. Lily is here because she worries for you. It's only natural for her to look after you!
"...But I am your wife." Says Evelyn. "I just... I want to feel special... I want to feel beloved and treasured... And sometimes, yes, I might want you all for myself. Is that too much to ask?"
"No, it's... Of course I love you. You are so cool and smart."
"Am I?"
You say yes, of course. What else could be said to that beautiful woman? She may not believe you fully but she wants too, she wants to believe and she loves you. She tells you not by way of words but with a kiss. That night you make sweet love under the stars, alone but together. Her pussy folds grab you like magnets, she pleads you to stay inside her. The next night, Lily enters the room without asking. Evelyn gives you a quick look but doesn't say anything else. You think that if she wanted her to go away she would say it, right? So, it must be ok for her to stay. What you don't gather is that she wants you to be the one to say no, the one to say I love you more than I love her, to prove her that she is your wife, but you don't say that.
Because you don't like lying.
That second night you made love the same way, but do so under the gaze of Lily. She didn't say anything, no words of encouragement, no teasing. She just stared. At one point, her hands undo her trousers and she shows you both the humidity of her pussy, the origin of her lady musk, which now possessively invades the room. She doesn't masturbate, she just pats it like a good pet and stares. Whenever you look at her, her eyes are set on you and it makes your dick so much harder, it makes the sex with Evelyn feel even more better. She is always smiling, always pleased. As your love stick goes in and out of your wife, you feel like you are pleading two women.
For a year you are quite happy as husband and wife, or at least you think so. Evelyn always gets you to cool places and knows so many things, she plays the piano and teaches you to sing along. You feel wonderful around her, and you always want to listen what she haves to say, no matter the subject. You two go to operas, to museums, art galleries, to the theatre, book presentations, concerts, anything. And she always knows so many minute and curious things about everything. Whether it is a bel canto from the XVI century or an 20 years old rapper, she shows appreciation for all forms of art, and her enthusiasm is contagious. At one moment you take her hand and tell her. "I'm married to the most beautiful and smart woman in the world" and again, she believes you. She wants to believe. A tear falls from her eye as she kisses you. She whispers in your ear "I can wait to get home and make you mine".
One day though, a storm came to your love nest: Lady Cassandra Barton has died over the night, apparently by a mix of **** poisoning and **** overdose. She died alone in her mansion, all the maids and servant that remained had been fired the night before by her order. The body was found by one of Lily's lawyers. The news hit your heart like a hammer. Why couldn't she learn to be happy? Why couldn't she...? You run and run across your home, **** to scape anywhere, and there you find Lily. She knows, she understand, you find confort in her bosom. She hugs you back and tells you that everything is going to be fine, that she loves you so much and that she would never let anything bad happen to you.
You never noticed that by her side was Evelyn, that she had opened her arms too, to offer the same comforting hug, but you didn't even look at her. You never saw the look the two women shared, the way Lily smiled to her friend, with such cruelty, with such assertion of superiority... And Evelyn could do nothing. When the hug ends you ask for your wife, but she is already gone and Lily tells you not to worry. You never hear them argue about you, she never has an argument with you herself, you never have a scene. It all just slowly drift away.
You never get divorced officially, you just stop seeing each other. She starts to travel and her travels keep her away from you for longer and longer. She calls you everyday at first, but then once a week and then she stops calling. One day, she no longer comes back. It doesn't seem more important or dramatic than other days, it was as if she just didn't feel like coming back. That night, you run to your sister again, to the sweet relief of her arms, and she is so willing, so nice and caring. You don't give much of a thought to the fact that she was waiting for you, that she is naked and smells like a recent shower, with maybe a bit too much of perfume for a woman. Her skin always feels so nice.
"I know it hurts, Mark... But things like this happen... We will find you a better woman next time."
"But she was... She was perfect..."
"I know she seemed to be... But women can be deceiving... Even the better ones can hurt you, but not your onee-san..." She says that last word playfully. You have started to watch a lot of anime together lately, and she sometimes likes to imitate some things from them. It all seems so innocent and fun.
"No, you will left me too..." You say, drowned in grief.
"Oh you silly... I would never ever leave you... You are my prince, my sun, my boy. Don't you remember?" She hugs you with even more strength. "Am I not your mama? Is my bosom not warm?"
"It is..." The tears don't let you speak more coherently.
"Then, give it a kiss and it will make you happy, like I always do... Come on, kiss my nipple, sweet brother, it has all the answers to your grief." You do just that, you kiss that engorged thing, and it produces the first jet of milk, directly into your mouth, so warm and tasty, she makes a happy chip when you do that. "There, there... You might recognise the flavour... Don't be shy... I have to milk them everyday, because I produce sooo, sooo much... But it is all for you... Only you."
You drink and drink... You are so used to the flavour, so addicted to it after years of daily exposure... Just as she expected.
"My lovely brother... Women are all deceiving, untrustworthy and mean... A wicked flock, the whole of them. But we are more that that, ours is a link of blood and duty. I will never leave your side, I will never stop loving you and no one will love you like I do. Drink brother. Drink me. I will sing you a lullaby and put you to sleep, but you must drink me..." As you fall into sleep, her last words become blurred. "Drink me and be all mine..."
The next morning, you wake up with the feeling of a hangover, even if you don't remember drinking anything. You are naked and alone in her bed, a gentle shade of sweat covering you. Your cock feels weird, is all reddened and sore and it's coated in sticky and smelly liquids. You touch it just bit, but it hurts and so you try to ignore it for a bit. A glass of milk waits for you on the side table, next to a small white card with a red heart drawn over it. You gulp it in one go before even thinking about it.
As you turn on the TV, you see a familiar set of a familiar morning show, the one where you once heard lady Cassandra be interviewed. Lily is there now, and she looks so beautiful. She always was a busty woman, but seeing her on TV makes you notice how much she has actually grown up. She wears much more solemn clothes, all black. "Lady Liliana Barton, welcome to our show" says the interviewer.
"Please, call me Lily. I'm not as worried by etiquette as my mom." Her smile looks as radiant as ever, even on TV.
"I was hoping you will talk to us about that. It's being three years since she left us. The Barton Conglomerate has been eerily silent since you took control of it."
"I prefer the term modest. It's still hard to talk about this, but my mother was a sick woman, she carried a lot of sadness in her life and she didn't always managed that grief in a healthy way. We all miss her, even if she was a difficult woman."
"What do you have to say about all those rumours and conspiracy theories that circle around her ****. Many of them seem to involve you, specifically..."
"I think it's sad that so many people are willing to make fun of such a tragedy and play with the grief her family and friends carry to this day. Look, many of you remember Cassandra for her **** and her late years of scandals and untreated dementia, and she did say terrible things, but I also remember a strong and good hearted woman, I remember a loving mother, who always had a smile on her face and who taught me all I know, and value. That's who I want to remember. Her research into genetics, as misguided as it was in its conception, gave us groundbreaking advances on which our labs still work on to this day. The Barton Conglomerate is now a full supporter of men rights and racial equality, but it never stopped being a spear of innovation and research."
"You were recently featured as the Times Magazine Person of the year and by the way, you just look gorgeous in that photo."
"Oh, thank you. That's really kind."
That day, before she returns, you enter the internet and search for 'Cassandra Barton theories.' You end up in a weird youtube channel that insist of showing photos of Lily shaking hands with some Georgina Soros, who they say is the devil. You quit the silly thing when they try to convince you that she is somehow a lizard. Lily is not a lizard! She is also not an evil person. How could she be?
Since you started living just with her, things change slowly, day by day. You notice that your cock is always hard, even if you are not having dirty thoughts. Something seems off about the word, like it's so hard for you to think properly. You had to ask her something... Something about... Well, If you have forgotten about it so soon it must not be that important. Right?
A month later you manage to stay awake for enough time, you run to her studio. It must be here, in her computer, you find the folder, is not really that well hidden. The first video shows you a recording of yourself, as you sleep. Lily is taking off your clothes, she get on the bed and... Her milk tastes so good... No, you have to look. Don't loose your focus. Lily is naked too in the video, she jumps on your cock like mad, riding you with fierce determination. She forces you to eat her pussy, she rides your face... There's more videos, there's hundreds of them. She doesn't skip a night.
"My silly brother." Her voice sounds as sweet as always. "What are you looking at?" She sounds so worried, she loves you so much.
"You... We are... Fucking."
"Of course not, my sweet boy. That would mean that I'm not better than Amelia or our mother... Why would you think that of me?"
"I'm sorry, mommy. I was..."
Her hand moves quickly to your forehead. "Oh my goodness, you are just burning with fever! Did you catch a cold, my sweetie?"
"I'm sorry, mommy... I don't feel..."
"It's ok, it's ok... You just need a bit of pampering and rest and it will all feel fine. Aren't you just a bit thirsty?" Her engorged Nipple is already kissing your lips, your instinct makes you open your mouth. The last thing you feel before falling asleep is your bulgie being undone by anxious hands. Something warm and humid touches the tip of your dick.
It's another day now. The sun tells you that it must be early in the morning. Lily is not home, you could so easily... What you actually do is go through your morning duties, like you are supposed to. The last thing you do is collect the mail. Lily likes her letters and packages to be properly ordered when she arrives and she doesn't trust the maids to do so. Amidst the voluminous boxes you find a mysterious letter, handwritten in dark ink. It's cover only says: for Mark. Opening it brings back a forgotten smell.
"Mark, my brother, my dirty peasant, my beloved. I know we won't probably see each other again. It took me a lot of time and tears but I have accepted that already. I have no power to defy Lily and her decisions. Sometimes I **** myself with the thought that something could have been different, that maybe I should have stood against her, but I didn't and the past is already set. I don't know if you think of me, but I wanted to tell you that none of your efforts were in vain: you told me that I deserved to be happy, that I was more than a broken girl and I will honor those words to my grave, even if not having you by my side makes it so difficult, even if you no longer think of me. I haven't tasted a drop of **** in nine years and I have pursued my carrer as an artist, although only recently I've been able to make a living out of it. It's still far less that what Lily offered me, which I never accepted, but it is honest money.
My art heals my wounds, is through it that I honor your words and that I remember you. It cleanses the void and emptiness inside me and leaves me with a calm and clarity I never thought I'll be able to possess. I'll never be able to express my gratitude, and so I will remain silent. I just hope you too managed to find your own happiness, the one you too deserve.
I just wish that one day I'll be able to create something as beautiful as you.
Always your bitch, Amelia.
The words feel hurtful. Why would she want to hurt you? Lily never hurts... She... You take a piece of paper. You write in it as quick as you can. "Please, you have to safe me. She is evil, she..." ...but why would you write that? Lily would not like that. You wouldn't do anything that Lily does not want. It would hurt her. You don't want to hurt her... She makes you... happy.
Four years later.
"Ah, good. You came just in time for your breakfast."
You find Lily in your kitchen. She is finnishing milking her left breast. She does these things much more openly since she is done with your conditioning. That seems to make her happy, and you love that she is happy.
"Uhg... I know you prefer it directly from the source," she says, delivering the last drops. "But we must not let our pleasure make us forget our duty. You must have a fully nutritious breakfast."
"What does it have today?" You ask.
"I'm testing a new strawberry flavour." She says as she starts mixing the milk with her other ingredients. "I really hope you like it. And of course it has the usual mix to make you produce much more cum and keep a larger hard-on. I think we will need it tonight."
"Are your friends coming?"
"Are they not your friends too? I thought they might be with how good they tread you." She winks at you playfully. "That reminds me that it's past nine o'clock. You have had a good night rest but it's time for you to be caged. Come here."
You dutifully walk to her and present your naked cock without question. She gets your custom cockcage and slowly puts it on your member. She does so with her usual love and care and her smile. She first introduces the urethral insert, penetrating your own cock with her gentle fingers, she then closes the rest of the cage around it. Your balls are left free and hanging. She always likes to have easy access to them.
"There, there. You look so beautiful, my little brother, and this will make sure that not a single drop of your tasty cum gets wasted. We don't want you to spoil your seed too soon. We want you to produce a big and sticky load, to make your mommy proud in front of her friends. You are still a bit flaccid, though, so you better start drinking that milk already!"
The party goes as always. the sun is already set and there's like fifty women in the celebration room. Lady Liliana is the queen of the event, and the others refer to her with respect and admiration. She parades you around the room, dressed with your cockcage that makes it so difficult to contain your impossible hard-on. A collar surrounds your neck and she handles the end of its chain. Those are all your clothes. She herself dresses in a corset that covers only her tummy, leaving both her pussy and her humongous breasts exposed. Impossible high heels sustain her toned and pale legs, obscured by a black garter belt. Her beautiful smile never leaves her face. She is so proud of her boy toy and she shows you off to all her friends without shame.
A slender woman of importance approaches the royal couple. She carries another younger woman, at the end of a chain. "My lady Barton, I must congratulate you on another wonderful evening. Everything looks... exquisite."
"Are you perhaps talking about my boy's cock?" Asks Lily.
"Oh, am I that obvious? Is just... It's so big and jummy... Such a shame that you insist on keeping him in that tiny cage. I would..."
"Caged he stays for now, I'm afraid. But please, do tell us what you would love to do with him. We would like to hear it."
"Oh I would ride him until he begs me to stop. Uncreative, I know, but I have a taste in minimalism."
"Classics are classics for a reason. I'm afraid he still not set to cum for a few hours more but please, if you would like to, you are free to stimulate his cock and his balls are all accessible. I would love to know that part of cum production comes from you."
"A tempting offer, but I have here someone who would be happy to take my place in humiliation. Marian." She says to her own toy. "You know what to do."
The three of you wait with expectation as the woman lazily gets on her knees. She lifts your cock over her face and proceed to chew on your balls without a hint of passion, but a well refined technique. Her eyes are cold and uninterested, half dead, but her mouth feels like pure heaven. She makes you moan really quick and you feel another orgasm being frustrated by the urethral insert. You feel like cumming constantly, but your mommy's devices do not let you. You somehow know that one day Lily will task you with fucking both of these women for her pleasure.
"My daughter here felt she had the right to usurp my possessions and I thought it was time to teach her a lesson." Says the older one.
"A fine choice." Says Lily. "It seems she is learning her place fast. My boy looks very pleased."
"How often do you let him cum?" Asks the mother as the daughter chews on your balls.
"Once a month. More than that gives you diminishing returns and less than that... It just doesn't taste the same."
An hour later, all the women form a circle, a few of them carrying her own and caged boy-toys. The priestess raises her hands to the congregation in a sign of love. "Sisters, we are here reunited to share among us the gift of seed. Those of you who seek the prize have presented an ejaculator and his prowess shall be judged. A cup will be positioned for him to fill. He who fills it to the largest amount shall be crowded our king and her owner shall choose what to do with all the seed: To eat it in gluttony or to share it in friendship. Let the feast begin!"
As you all get in line for the process, a woman comments with scorn. "My Robert here has been disappointing as of late and so he would not join the others in the cumming. He would just watch and yearn what better behaved men get."
One by one, each woman approaches and uncorks her own toy. Some start cumming immediately, moaning and whining, others require more stimulation, probably first timers. Some women insist on stimulating, even when it doesn't seem necessary. Some user her fingers on the prostate, others jerk off the cock or kiss the male with passion. The biggest of their creampies fills half of one the cups, which produces a thunderous applause from the congregation. You are the last one to go, as expected.
You hear Lily's voice in your ear, her voice is so sweet. "I love you baby brother, I love you so so much, I always wanted you to be mine, only mine. You make me so happy... All my friends are watching, they wish they have a lover as manly as you... But you are mine." As she speaks, you feel the tip of the rubber cock poking your asshole. Knowing your place, you lower your back and get on all fours to allow her an easy access. You are used by now to be pegged, but it always feels different when in front of a crowd, maybe because your mommy always chooses the bigger dildos for such occasions. Lily grabs your ass with fierce strength, she fucks you without pause or rest, going in and out of you with lubricated ease. Soon, the whole crowd of women is cheering at the royal couple, clapping to the rhythm of their pegging. Your cock hurts so much in its cage, it feels so liberating when she uncorks you, and then you start cumming and cumming, half the cup and more. You fill it to the very edge as Lily keeps fucking your ass to make sure you don't hold back anything, and not even your loud moans can silence the cheers of the sisterhood. You could hear a loud 'pop' as you fall onto the floor and your mommy's cock leaves you.
"Oh, queen and owner of the champion. What shall we do with such portentous offering?" Says the priestess.
"The cum of lesser men shall be shared among us all in friendship, for we are sisters in gluttony, but the cum of the champion is mine and mine alone, for he is my boy, my beloved, and I yearn and life for his taste." She lifts the heavy cup with both hands and in one sole go she gulps the entire thing. She gulps and gulps until there is not a single drop left, her throat makes such a delightful sound, and when she lowers the cup, only her smile remains.
Her beautiful, beautiful smile.
THE END
My, that was a long and fun chapter. Please show your support and opinions in the comments. This took a lot of effort, so don't be shy to share the love! More endings are coming and this one is not the craziest!
THE END
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The Fairer Sex
A world of strict gender roles, reversed
Explore a world where the roles of each gender are still strictly enforced though societal and social pressures, only they are the opposites of those we know. Women are expected to take the lead in almost every situation, with the men in their lives as meek followers, and scorn and mockery awaits anyone who steps outside these boundaries of good behavior. This is clearest of course in the world of romance.
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- Mother, Mother-son, Discipline, Bondage, Spanking, Femdom, Training, Alternate Universe, Gender Role Swap, Crossdressing, Personality Change, threesome, femboy, Proposal, Romance, Pussyjob, Humping, Female Supremacy, Male Sub, Gender Roles, Marriage, Cuckquean, Pegging, Love, Cum eating, spank, pretend couple, interracial, Outercourse, mommy, CFNM, Nursing Handjob, Gentle Femdom, Wife, Boobs, Handjob, father, daughter, panty sniffing, Striptease, Punishment, Fdom, Domestic Discipline, Comfort, Tears, Househusband, 1950s, Mommydomme, MILF, Doctor, Nudity, Choosing, Older Sister, Amazon Position, Riding, Rough, Muscles, Amazon, Workplace, Stripping, Domination
Updated on Jun 13, 2025
by Conan The Librarian
Created on Aug 13, 2020
by Haoro
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