[MF] Sister helps prepare me for prison

My older sister had got mixed up with a bad character who was dealing drugs and who had been killed in a drug deal gone wrong about 6 months before this story begins. I had been letting her stay with me until she could get back on her feet.

We were watching TV when the cops burst in and told me that an informant had told them that their were drugs in my Apartment and while I was trying to make sense of what was going on one of the cops came in to the room carrying a paper bag full of packets of white powder and said “Found this in the top of the hall closet”.
I looked at my sister, tears welling up in her eyes, and I said “the drugs are mine”. The cop said “That’s not what we heard, but if you wanna take the rap, put your hands behind your back”.
My sister later told me she had found the drugs in her husband’s stuff after he was killed and being hard up for money, she had tried unloading them on one of the guys her husband had hung out with. That dude had narc’d her out trying to cut a deal for charge his was facing.

My lawyer had got the trial postponed for 6 months but told me that I was mostly likely going to have to do a year. I was terrified. I was only 22 and having done some reading on the Internet I knew what I was facing.

—

My sister felt terrible about what had happened but there was no way I was going to let her go to jail. I did what I had to do.

I was sitting on the couch staring in my beer when my sister walked in, sat down beside me, and put her arm around me, and asked if I was OK.

I told her I had been doing some reading about what I was facing in prison. I said “It’s going to be bad. I’m going to get fucked.” My sister said “you don’t know that’s going to happen”. I shook my head and said “look at me. I might weigh 130 soaking wet, blonde hair, it’s not a matter of if, it’s just a matter of how. I can either agree hook up with a man who will protect me and be fucked by him or be gang raped and passed around until I pair up. But either way, I’m going to be getting fucked. A lot.”

My sister laid her head on my shoulder and held my hand. Neither of us said anything for a few minutes and then my sister said “It’s not so bad if you relax. I can help make it easier”. I despondently said “How”. My sister said “Let me start massaging you with my fingers. I’ll be gentle. I promise i won’t hurt you. Once you get used to my fingers, I’ll start using a small dildo, trust me, I know how to make this easier for you.”
I said “You really think that will help?” My sister nodded, got up, and turned off the TV, and told me to come with her, and led me to my bedroom.

“Face the bed” by sister said and then she put her arms around me and pulled down my shorts and told me “lay across the bed. I’ll be right back”.

My sister came back in a moment with a jar of Vaseline and dipped her fingers into it and began rubbing my asshole. “I want you to relax and when you feel me push I want you to push back, OK?”
I nodded and she slipped a finger into me. I gasped. More from the thought of what just happened than from the pain. My sister slowly pushed her finger in and out. I concentrated on trying to relax.

My sister said “Just let my finger fuck you. You’re dong great.” It wasn’t long before I noticed I was getting erect which was uncomfortable laying on my stomach. I was confused and embarrased why I was getting hard and why my sisters fingers were feeling so good.

My sister said “I know you’re uncomfortable. You are going to have to trust me. What’s happening is completely normal. All guys get hard if a girl puts a finger in their ass. I need you to turn over and pull your knees back for me, OK?”

I took a deep breath and rolled over. My cock was hard as a rock. My sister said “I’m going to put two fingers in you now, OK?” I nodded.

I moaned as my sister pushed two fingers into and began fucking me with them and it’s wasn’t long before I felt I was getting ready to cum”.

I gasped out for my sister to stop and said “I’m going to…”

My sister just kept fucking me with her fingers and said “It’s OK. Just let go. Let go.” and reached down with her other hand and gently squeezed by balls.

I arched my back and cried out as I exploded and shot a fountain of cum into the air. I felt my ass clamping down on my sisters fingers with each squirt.

As I lay there completely spent my sister slowly pulled her fingers out my ass and went into the bathroom to cleanup.

She came back in a minute later and laid down on the bed next to me.

Then she said “I know that had to be hard letting me do that to you and you cumming in front of me like that. You know I’m doing this because I love you, right?” I said “I know”.

—

My sister fucking me in the ass with her fingers became routine until one Friday afternoon my sister brought a bag into the bedroom and told me we were going to do something different that night.
She removed several life sized dildoes from the bag, a butt plug, and some lube.

My sister said, “I think you’re ready for for something a little bigger than my fingers and I need to talk to you about something else you may not have thought about. Getting fucked in the ass when you’re not used to it is bad enough, but getting fucked in the throat when your not ready is even worse.

My sister held up one of the dildoes and said “from now on, whenever i fuck you, I want you to practice sucking on this. And there’s one more thing. From now on, after I finish fucking you, I’m going to put this in your ass. It’s a butt plug. I want you to wear it all the time except when I am fucking you. When you get used to it I will put one in you that’s larger, OK?” I nodded.

My sister then reached into the bag and pulled out a harness, attached one of the dildos and slipped it on. The dildo looked a lot bigger now that she was wearing it. She noticed me eying it and said “I’ll be gentle. Take your shorts off and get on the bed”.

In the weeks that followed I learned to take a dildo down my throat and a dildo in the ass. One night, after fucking me especially hard, my sister lay next to me with her head on my shoulder and asked me “Do you feel any better now about what you’re facing? Am I helping at all?” I put my arm around her and said “Yes. I don’t know what I would do without you”.

My sister then said “I don’t want those men to hurt you. The dildo I am using on you is normal sized but there are going to be men in prison with cocks way bigger than I have been using on you. The truth is there’s no way you will be able to take those kind of cocks without your asshole being ruined.”
I began to cry. I had hoped my sister could somehow save me from the brutal pain I was facing in prison but deep down I knew she was right.

My sister wiped my tears and said “Look. It’s not the end of the world. So you have wear a small buttplug the rest of your life. The question is how do you want it to happen. Do you want your ass ruined in prison or do you want to let someone who loves you do it?”

I looked down and said “I want you to do it”.

My sister lifted my chin up and said “We can get you drunk first and i’ll use numbing lube. It’s still going to hurt but not as much as it would the other way”.

I asked “So how big will…” My sister answered before I finished the question and said “about 10” long and big around as a Coke can. I paused a moment and then said “Maybe if you go really slow” My sister replied “that won’t work. If we go too slow your ass might be able to stretch without…”. She paused a monment and then said “There’s no easy way to say this. I’m going to have to tear the muscles in your asshole. Once I do that your asshole will never close tightly again. You’ll need to wear a very large butt plug for a couple weeks while you heal.”

I said “so will I lose control of my…”

My sister said “No. You will notice that your bowel movements will be a lot easier and you could have a little leakage if you strain or don’t eat enough fiber”. That can be solved by wearing a small plug or a pad. There are excercises you can do where you bear down that will help”.

“So when do you want to…”

My sister said “If I order it today it will be here by this weekend.”

I said “Go ahead. Let’s get it over with”.

My sister leaned over and kissed me on the cheek and said “It’s going to be OK.” And then said “There’s something else we need to work on I have been meaning to talk to you about that will make things easier for you in prison.

I know that is going to sound gross but I want you to start eating your own cum for me. You don’t want to puke in someone’s lap inside.

I grimaced.

My sister said “Most men have a strong mental block about eating their own cum, otherwise there would be a lot more happy women in the world. We’ll start off slow, just a drop on my fingertip, but it’s better for you to go ahead and get used to it now slowly instead of having to get used to it all at once inside.”

That night while my sister fucked me I licked my own cum off her fingers and before long I was cumming in her hand and letting her feed it to me every time I came.

—

When I got home that Friday my sister was cooking dinner for us. I sat down in the recliner and she walked over, handed me a jack and Coke, and pulled my shoes off and rubbed my feet.
I said “I guess it came in”

She smiled and nodded and said “drink up”.

By the time we finished dinner I was working on my 3rd Jack and Coke and my sister slid a small pill across the table and said “Take this. It will help”. I didn’t ask what it was. I trusted my sister more than anyone.
After about an hour and a few more Jack and cokes I was getting numb and my sister took my hand and helped me back to the bedroom, laid me down on the bed and began removing my clothes. The room was now spinning. I was definitely fucked up. I felt my sister put her fingers up my ass with something cold on them. My sister said “this is going to make your ass numb.” I laughed and said “I think my whole body is numb”.

My sister then said “I’ll be right back and went into the bathroom”.

She came out a minute later and I asked “Do you have it on?”

She said “Yes. Do you want to see it”.

I slurred out “I’m too drunk to sit up. Just fuck me”.

I remember feeling pressure against my asshole and my sister telling me to take a deep breath followed by a searing pain that felt like someone had stuck a hot poker up my ass. I remember crying out “It hurts!” right before I blacked out.

When I woke up I was laying on my side with my sister snuggled behind me. I could feel a dull ache coming from my asshole and my ass feeling really full almost to the point of pain. My sister felt me stirring and whispered “Good morning”. I asked “did you…” And my sister said “Yes. You’ve got a really big plug in. Just try and relax.”

I said “my head” hurts. My sister handed me a glass of water off the nightstand and another pill and said “take this”. It will help with the soreness and the hangover.

I then realized my balls were sore. My sister asked “What’s wrong”. I said “I feel like I’ve been kicked in the balls. My sister said “you were hard while I fucked you but you never came. You just need to cum. Do you want me to help? Just relax and let me do it”.

My sister reached around and took my cock in her hand and began to stoke it and asked “Does that feel good?”
I moaned “yeah but…”
My sister replied “But what…?”

I said “Everything else we have done has been you preparing me for prison. This is… different.”
My sister said “It’s just a hand job. It’s not like we’re fucking. It’s the least I can do after everything you’ve done for me.”

It wasn’t long before I came in my sisters hand and then drifted back off to sleep.

—

My sister had said my ass needed a few weeks to heal before she ass fucked me again and had been throat fucking me for the last few weeks. The huge plug my sister had me wearing for the last few weeks had taken some getting used to but I was used to it now.

That morning my sister told me that she needed to begin fucking me in the ass again and assured me that it would be a lot easier now.

It was now only about 3 months until the trial. That night my sister told me to have a few drinks but that I shouldn’t need to be drunk. She removed the plug and slipped her fingers inside me and ran them around the inside of my asshole and said that the couple small tears I had were healed up.

I felt pressure and then gasped as she slipped her hand into my ass and made a fist and said “you’re ready.” She withdrew her hand then positioned the huge strapon she was wearing at the entrance to my asshole and said “take a deep breath and push as I push” and a moment later she pushed the head of the dildo into my ass. This time the feeling was more of a intense feeling of fullness instead of pain.

My sister gave me a minute to get used to the dildo then asked if I was ready for her to put it all the way in. I nodded and then my sister, in one smooth motion, thrust the dildo into me, until her hips bumped my ass. It was all the way in and amazing it has not really hurt.

My sister asked “Are you OK?” I said “Yes, My ass just feels incredibly full, but it doesn’t hurt”.

My sister said “Good. I’m going to begin to fuck you now. If it gets to be too much, let me know”. And with that she began to thrust the dildo in and out of me. Slowly at first then faster and harder.

The huge head of the dildo was pressing down on my prostate every time she pushed it into my ass and in no time my cock was hard and I gasped “Omg! I’m Cumming! My sister said “It’s OK babe. Go ahead and cum for me.
Don’t be embarrassed. Let it happen.”

A moment later I started to cum. The first contraction pressed my prostate against the dildo so hard I thought it would burst.
Cum and prostate fluid shot nearly to the ceiling.

Before I could cry out another contraction slammed my prostate against the dildo again, then again, and again, and again, and again. As my orgasm finally began to ease my sister slowly pulled the dildo out of my and stood looking down at me with her mouth wide open unable to believe the amount of cum she was seeing all over my stomach and chest. I had never experienced an orgasm like that in my life. Nothing else had even been close.

The following day I got a call from my lawyer. The guy that had narc’d us out had been found dead from an overdose. My lawyer said that he told the DA that I was thinking about changing my story and saying I was just trying to take the rap for my sister and that my sister could just say that she didn’t know the drugs were in her dead husband’s stuff, and with the only witness to the contrary now dead, from all things, a drug overdose, the state was dropping the charges against me.

That night my sister and I celebrated and got drunk and watched a movie and when the movie ended my sister asked if I was ready to go to bed. I told her to go ahead, that I wasn’t really sleepy yet.

—

My sister said “I didn’t men go to bed to sleep. I was going to fuck you”
I said “You don’t have to do that anymore. I’m not going to prison”.
My sister said “We need to talk. I want you to tell me the truth. Have you ever cum as hard fucking a girl as you did when I fucked you last night?”

I looked down, embarrassed.

My sister said “I didn’t think so. I going to say some things now that are going to hurt but you have to accept. You are never going to be happy fucking girls again. You are not going to be happy now unless you have something up you ass and after what I did to your ass no man is going to want it. You were willing to give everything for me. I am responsible for what happened. And am now responsible for making sure you are happy”.
I said “I can’t ask you to do that. What about you? What about your happiness? I can’t fuck you. You’re my sister. You need someone who can make you happy.”

My sister said “I never told you this but I’ve never been able to orgasm from vaginal sex. I get off more from using my magic wand than I ever could from sex. I would be happy just to have someone to hold me and kiss me while I masturbate. I don’t want kids and you’ve said you don’t either. Can we at least try this and see how it works? Please?”

Everything my sister had said made sense. Maybe this could work. I looked at my sister and said “It’s going to feel funny the first time I see you with no clothes on”.
My sister squealed with delight and hugged me and then looked in my eyes and kissed me, then slipped her tounge in my mouth and kissed me hard. At the same time she unzipped her shorts and put my hand down her panties. I began to gently rub her clit. My sister began nibbling on my neck and then whispered in my ear “I am going to fuck you harder tonight than I ever have”
— The end —

Source: reddit.com/r/gonewildstories/comments/9a6htv/mf_sister_helps_prepare_me_for_prison