Letter to Cuckold - Your Wife & Sis

Story Info
Adam admits to fucking Jason's wife and marries his sister.
6.9k words
3.18
73.3k
96
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

*Note: If you enjoy the idea of being a cuckold, imagine this is being written to you. If you enjoy the idea of being a bull, imagine you are writing this letter.*

*****

Dear Jason,

Thanks so much for everything you did for the wedding last night. Your sister Ashley and I really appreciate it. I am writing this to you because I know how protective and watchful you were over her during this whole process. You weren't sure if I was the right guy, or if I was the best person to take care of her. I remember you feeling a little aggressive sometimes over your doubts about whether or not I should marry her. I thought I'd write you this and let you know how her first night of marriage went so that you could feel at ease. But I have a lot more to confess to you, and some of it involves your wife. Please read this whole thing.

After we got to our suite, I carried your sister into the room and sat her down in bed. Getting her our of her wedding dress took sometime, but it was worth it. After all the layers were off, we finally got down to the sexy pair of bridal lingerie she was wearing. What's amazing is, it was pretty much wearing nothing. It was a pair of crotchless panties and a bra that showed her tits. She was absolutely beautiful. She has these almost brown areolas that surround her nipples that just beg to be sucked on and kiss. I sat next to her and started kissing her. I felt the heat on her breath, all she wanted was to get fucked.

I had specifically asked her not to wear antiperspirant so she had her sweaty, sexy smell. I don't know if you know it, but I do. It was intoxicating. I took her left breast in my hand and laid kisses on it. Then I worked my way to her neck and upper chest and made sure I kissed and sucked and licked until I left huge hickies all over her neck and chest. You'll see them in the morning when we come over. I sucked her tits. Jason, your sister's tits taste like heaven. The sweat, the skin, everything is perfect. I just sucked them till I left them red, while I fingered her eager pussy.

Your baby sister got down on her knees and freed my huge cock from the pants and boxers I was wearing. It was absolute heaven to see her beautiful, incomparable face take my dick into her mouth, and suck, and suck, and suck. Ashley's lips were dripping saliva as her lips and tongue took me to amazing places. I watched her perfect face as she pleasured me by taking my penis into her pretty mouth. Those same lips that call you brother, were wrapped around my cock. I thought about that and reveled in the fact that drop after drop of my pre-cum was making its way down your sister's tongue, throat and into her mouth.

I gave her the signal to stop and I lay her down on the bad. I ripped her lingerie off of her and then I saw it Jason. I saw Ashley's pussy. Your baby sister's cunt. Oh my God. It is the most beautiful pussy I've ever seen in my entire life. It has these outer lips that curve and twist and are raised to perfection, and inner lips that are like little flower petals. She had honey dripping out of her pussy because she wanted me inside so badly, and I started to lay kisses on her pussy petals and proceeded to lick and suck her cunt. She tasted like paradise. I've never had pussy like that in my life. I could lay there for hours just licking Ashley's pussy and drinking every drop of pleasure that flows out of her.

But I had my needs too. I got her to a point where she was involuntarily moving and gasping for breath, and then I stopped. She was a virgin and I wanted to make sure she was aroused enough to take me. I got on top of her, and kissed her, letting her taste her own juices on my lips and tongue. I took my cock, now fully hard, and 8 inches long. I was so thick she couldn't even get her whole around my girth. I placed it at her opening and just rubbed the head of my cock up and down, and up and down between her cunt lips, soaking me with her previous private fluid that no man before me has ever known.

I looked into her eyes for the last approval, to be sure she was ready for me. This is when you joined us in a way. I asked: "Are you ready Ash?" She said: "Adam, you know how my brother was being so mean to you so many times because he wasn't sure we should get married? He even tried to stop us once by talking to my dad?"

Uh oh. Where was this going, I wondered? "Yes." I said. But I was confused.

Why was she bringing up her brother? You? Then she told me. "You are about to take my virginity. When you break my hymen and enter my pussy for the first time, when you get your massive cock into my cunt, I want you to remember, you are fucking Jason's little sister. You are violating Jason's baby sister's pussy. You are taking me and making me yours forever. You're going to pound me and own me and fill me with you. You won Adam. You won and I'm your prize, and you're going to use me and fuck me and pound me and fill me. And nothing my brother does can ever undo the fact that you are about to conquer his baby sister's pussy."

"Ashley, god damn that is hot. But I want to think about you. About us." I replied. She had my hard-on turning into a fucking beam of steel the way she was talking.

She continued to betray you. "I love my brother." she said. "But he can be an asshole sometimes. I want tonight to be your triumph. Your victory. I want you to feel like you won. And it turns me on. It turns me on that you are about to fuck your friend's little sister, almost against his wishes, and that my body, my ass, my pussy, will always be yours. Now shut up, and fuck your friend's baby sister. Fuck your wife. Make me yours."

I couldn't resist. I grabbed her hips, kissed her one more time, and then I thrust myself, at once, into your little sister's vagina. I broke her hymen, and she screamed at the top of her lungs, but only once. I saw tears in her eyes as I bottomed out against her cervix, gently. I stopped and wiped them. I kissed her. "Are you ok Ash?" I asked her.

She nodded yes and just kept whispering: "So big. So big Adam. You're so big. You're so big." I held myself inside her, not wanting to move even one bit, afraid I'd hurt her. Finally, I felt her pussy contract around me length. It was almost as if it needed to come to life and recognize that it had been finally completed. She wrapped her legs around me. "Pound me. Start slow, but when you feel me pull you in, pound my pussy. Pound it like I don't even own it. Because it belongs to you now. Always to you." she said. Your sister is perfection Jason. I don't even know how to describe it.

I slowly pulled out of her and saw the traces of blood. But along with that, I saw globs of white, thick, pussy juice. Coating my entire cock. I was showered in her most intimate honey. There isn't even a word to describe how I felt. I felt like my whole penis was screaming: "This is where I belong!".

I went back into her, and slowly started to pick up the pace. Her breathing quickened as she started to smile. She started encouraging me as her heels pulled me deeper. "Fuck your wife." she said. "Fuck your slave". "Fuck your woman." "Fuck Jason's sister." "Fuck my pussy." over and over again she repeated these as I increased my tempo.

"Slow down and take me from behind" she demanded. She got on all fours. I paid homage to her perfect pussy as it stuck out in the air by licking it clean and then I placed all eight of my inches back into your little sister's body. I began to fuck her. Hard. Her buns rippled the shock waves from my hips into her lower, middle, and even upper back. Her whole body was being fucked. "Fuck your slut." she said. And I just got to a point where I was thrusting the fastest and hardest I could.

This is when I realized all the things she was saying about you wasn't only for my feeling victorious. She has a fetish. She wants you to see her get fucked. She wants you to see me lay an onslaught onto your Sunday school teaching, perfect GPA achieving, volleyball champion little sister. She is getting off on it. She said something that confirmed it.

"Imagine if Jason was here watching us" she said as I slowed down my pace so I could grab her hair from behind. "What do you mean watching us?" I replied.

Imagine Jason sitting next to us, on this bed, watching you absolutely violate my body. Pull my hair like I'm your slave. His little sister that he protects and adores and takes care of so much, imagine him seeing me beg for your cock, and call myself your slut. Imagine him seeing how big your cock is and how he could probably never compare to you. Look at me, I'm drooling as you fuck me because you're so goddamn big."

"Ashley, do you wish he was here?"

"Yes." she replied. "I wish he was here." She spoke through the thrusts I was laying down on her pussy from behind. "I know he has an incest fetish and a cuckold fetish."

"He does?" I asked in amazement. "How is that possible? He's so masculine and alpha!"

"He's not. He pretends to be. Inside he just wants to fuck me if he can, and he wants men bigger than him to fuck his wife and get her pregnant with their stallion cum."

"Damn" I responded. I didn't know this about you Jason.

"Turn me around, let me talk to you." she requested. I pulled out of her and she pushed me down on the bed and mounted me, my entire length sliding back into it's home, into Ashley's perfect pussy. I felt every inch inside her grabbing onto every inch of me. Refusing to ever let me go. Her honey coated my entire pelvis.

"I know about you and Jenna." she said to me. Looking into my eyes as he squeezed my cock with her cunt muscles.

"Jason's wife Jenna?" I asked. "What about her?".

"I know you've been fucking her since we started dating. I know you fucked her the morning she got married. I know you fucked her the night she got married after Jason passed out after their drunken wedding night sex. I know that you've been fucking her for five years. I also know that both of her kids are yours. I know that you love her in your own way, and that she loves you."

"Ash, it's not what you think." I told her. I was fucked. Oh Jason - everything she said is true. All of it. I've been making love to Jenna since about a month after I started dating Ashley after asking for your bromission to do so.

"It's not what I think, it's what I know." Ashley said.

"Ash, I love you, look..." I really wasn't sure what was going to happen.

She put her hand on my lips as she rode me, gently up and down. "Shut up and listen." she started.

Ashley continued: "I've always known because Jenna tells me everything. I know you've had more sex with her than her husband has. I know that Jason was turned on once that her pussy was so wet all the time, not knowing about the near daily trysts she and you were having and the wetness was just load after load of your cum mixed with her cunt."

Jason, that's true too. The wetness was just me. I'm glad that you liked the effect, and hope that if you really are into being cuckolded, that you like the fact that it was my cum inside your wife that entire time. The fact that Jenna is my secretary has made it really, really easy to pull this off for five years. The truth is, she isn't really my secretary. I have another secretary that actually does work for me. I pay that secretary 60k a year.

I pay Jenna 170k a year to do nothing for the company, besides have the title. I wanted to make sure it was high enough that there was no question about her leaving for better opportunities in case you ever brought it up to her. But more importantly Jason, I pay your wife Jenna 170K a year to be my "executive assistant" because I'm the father of both of her children. Of your children. There's a reason her insurance is so damn good that it pays for all of your needs, you've never wanted for anything despite you making half of what she does, their many private kid activities and fees have been paid "through scholarship" and she gets to take you and the kids on "work trips" to amazing places where she goes to meetings. You even get an assistant that helps you guys with stuff on these trips. I do send her to represent me in meetings in those instances, but we make them five-day vacations because I genuinely want to do right by those children, take care of them, and make sure they want for nothing.

Jenna's been coming to the office everyday, because we fuck just about every day. She goes to lunch with her friends sometimes, or hangs out with me in the office. Her MBA is helpful because she works with me to help out on projects sometimes, but it is just advisory. She's smart so she's actually saved the day a few times. But mostly, in the afternoon we get together in my office suite's bedroom to fuck and sleep the afternoon away. You've seen it before, the huge master bedroom suite attached to my office? It's large enough to be a studio apartment so I can sleep there during really tough work days or nights. What you never knew is that there is a closet of her clothes there. Clothes you've never seen, lingerie you've never experienced her in. The only thing you'd recognize if you were to go there, is her toothbrush. You know the ones you guys buy in bulk? She has one of those there, and her favorite mouthwash. She also has a picture of you, her, and the kids on her side of the bed.

"Don't you feel guilty? I had asked her once. "No." she said as she had mounted me. "Jason told me he really likes the idea of cuckolding and even me getting impregnated by another man. He mentions it every month. So I did everything he said he likes. Falling in love with you was an after-effect, but he said he likes this. I just haven't told him yet because I don't know if he's really ready. I love him, but I wanted to ease him into this. But make it too late for him to turn back."

You know how your wife is never available between 1-3pm and it's because that's the most important time of the day for her? That's because she's usually in bed with me, butt naked with my cum just flowing out of her pussy or ass. Usually we are asleep. She falls asleep in my arms every afternoon, but about once a week, one of her favorite things to say to me as she falls asleep on my chest, sometimes with my cock still deep inside her is: "You're so much bigger than Jason. So much bigger in me." Almost a whisper as she drifts off. So Jason, she basically goes home at 530pm to be your wife till 730am. Then she comes to work to be my personal slut and girlfriend from 8am to 5pm. I think I officially have about three to four times as many cock-hours in your wife Jenna's pussy as you do. You have sex twice a week with her I think. For me, its five days a week.

Back to your sister. So yeah, I basically lay there totally shocked that she knew all of this.

Ashley continued: "Look. I know what you are. I know you are a man who is extraordinarily successful, who is used to just having what he wants. I know that you love me and that if I asked you to stop being with Jenna, you'd do it. I also know that this huge cock of yours just can't be satisfied with one woman. I married you knowing this. So here's the rules. You can fuck ANYONE you want as long as you don't bring any STDs home. You have to tell me everything when you come back to me while you fuck me. And of course, my sexual needs, my emotions, our relationship comes first. Me first. Jenna second. And I mean Jenna second. You need to honor that woman like you are married to her because she is the mother of your children. She beat me to that. Anyone else you want after that."

I felt like I was in heaven. "Are you serious? Is this a test?" I asked her.

Your sister responded back, while gyrating her hips a little with my cock inside her. "No, it isn't a test. I'll prove it. I know for a fact, that five days ago, you had sex with Jenna, on her marital bed, in Jason's house. I also know that you left your watch there. I also know that you thought he was home early when you heard something downstairs so you pulled out while you were coming and instead of filling her up, you got cum all over the outside of her pussy. You got out of the house. What you didn't know is that the noise was me, and that I was there because YOU were running late and were supposed to be gone by then. I came because something Jenna and I love to share, is the aftermath of your fucking her. You just took my virginity now, but I've tasted load, after load, after load of your cum as it floods out of her pussy. I had to lick the outside that day because you had sprayed it all over her labia.

I was floored Jason. I had no idea. You probably are too. Your sister has been drinking my semen out of your wife's pussy. This was the best wedding night I could possibly have imagined. But I didn't know what Ashley's endgame was.

"So what does this mean Ashley. I'm, for the first time, a little unsure here."

"This is what this means." she said before she made the parameters clear for me.

By the way Jason, this is one of the reasons I married your sister Ashley. Jenna is an amazing woman, but she's a little submissive, at least with me. She doesn't take charge during appropriate opportunities. Does she take charge with you? You can tell me about it later.

Anyways, Ashley continued:

"You get me and Jenna as your lovers for life. But we have to tell Jason everything. Everything. This undercover fucking thing is hard for all of us, and Jason deserves to know. My brother is a good man, and even though Jenna doesn't see these things as betrayals, if she keeps them from him any longer, they will be. She and I talked last night while she helped me get ready for the wedding and ate my pussy."

She was absolutely right man. We had to tell you. Ashley leaned forward. "We want you to tell him. This needs to be man to man. Write him something, sit him down, whatever. But it is only fitting that you tell him, confess to him everything that you've been doing."

"You're right." I told her. "I will."

"Tomorrow." Ashley said.

"So soon?" I asked.

"Tomorrow. He should have known years ago but now that Jenna, me, and you are on the same page, he should know immediately. It's not fair that he doesn't." she replied.

"What if he wants to join this? Watch this?" I asked her. What are your thoughts?

"So Jason's has a five inch penis, it is about half of yours in girth. Jenna tells me everything. There's no way it will really do a lot for Jenna anymore, nor for me either. So if you are OK with it - and that's totally up to you - I want to let him know he can join. That he can fuck me if he wants to, or Jenna. That he has the privilege but not the right to have sex with me. It won't even compare to you, but I have a little incest fetish. He's my big brother and he's really close to me and I wouldn't mind giving him my pussy sometimes as a consolation prize for the fact that you've basically been cuckolding him this entire time."

"I don't know how I feel about you being with another man." I told her. I wasn't a fan of this.

"I want you to understand that with you, I'm your slut, your whore, your wife, your woman, your slave. You own my body and my heart. You can revoke his access by a word, but he can't revoke your access to Jenna. You own Jenna's body and heart too. She will fuck you regardless of what he says and if he gets too tough on her she will leave him for you."

I turned over Ashley and started fucking her missionary. We had been talking so long, and so intensely it was almost easy to forget that I was balls deep inside her. There was so much white thick frothy pussy cream on my cock and pelvis from all the thrusts that my entire erection was basically covered in a layer of her cunt juice.

I kept going slow even though all I wanted to do was unload inside of her the gallon of cum I felt like I had inside me from hearing how quickly my entire life was changing.

12