One Week in Heaven

Anal

— Fairly extreme brother-sister story. No one is under the age of 18

Rewritten and elaborated on since the story came to fruition with full consent. It is now almost completely accurate.

*

Here’s a true story that happened to me a few years back. Call me a pervert if you want. I regret none of it and both of us have gone back to normal relationships. Every now and then we act on it, but for the most part, we just accept it as what it was.

It was Christmas time and my entire family took a trip to my grandmother’s in Arizona. Everyone was assigned a room. I would have roomed with my little brother but he was put in the same room as my cousin, so I was to share a room with my older sister. No big deal, all things considered. We’d shared beds before. This was a few years ago. I had just turned 18 and Michelle was just a year and a half older than me. The perfect girl, in so many ways. I’d always secretly found her attractive.

The place was a ranch style house and we were given a room with a double bed. For anyone who’s tried to share a double bed, it’s not that easy. A queen bed you may occasionally bump into each other. A king you can pretty much sleep on your own side, but a twin, every movement you make you end up touching each other. After a long day riding horses with the family and a heavy dinner, we were both sent to our rooms early. I was used to going to bed late night, so Michelle and I lay in bed both unable to sleep. She looked incredible. Throughout our teenage years, I started to look at her in a new way. I often would make excuses to see her naked and masturbate later thinking about it.

This night I remember so vividly. She was in bed with a top and bottom next to me. The moonlight was pouring in the room. I could see her every curve in the bed. She was moving around in the bed and I was only getting more turned on. I decided to relieve myself hopefully without her noticing. If I didn t, there was no way I could possibly sleep. I put my hand on her stomach and left in there for a while my left hand slowly pulled on my dick. She is a deep sleeper and didn’t notice as my hand slowly worked its way onto her breast. Every few minutes I was worried she’d wake so I’d put it away, but I thought I had a built in excuse – If she caught me, I’d pretend I was asleep. It sounds stupid, but it actually worked. I moved my hand up to her nipple and kneaded her soft breast as I touched myself. No movement. My tension only kept me going longer. After a while, I got bold and moved my hand down her dress to her trimmed pussy. I touched the warmth as I took care of myself. I must have got careless cause she grabbed my hand and took it off her, but she seemed to still be asleep. I finally climaxed into a tissue from a box next to the bed. To this day, I don’t think at this point she noticed anything.

Either way, this continued the next few nights. But the problem was me. I was getting more and more careless. I would put a finger inside her and stroke myself. And I’m sure anyone reading this can guess what happened next. I got caught. She grabbed my hand and took it away from her pussy and looked over at me. Michelle has these big green eyes and I was so confused, so embarrassed. She whispered softly in my ear – “We can’t do this.” I asked her why not and we had a brief talk about incest and why it could never happen. To her, it was wrong.

But she knew I was too wound up to sleep. “You might as well finish” she said and I asked how. She thought about it and turned her back to me so we were spooning. “Just take care of yourself. It’s not that big a deal” she told me.( ( I took my dick out of my boxers and rubbed it against her ass through her underwear.

“Is this alright for you?” I asked.

“Sure, just don’t go inside me. It’s not that big a deal.” I rubbed myself against her ass crack til I came. “Do you feel better?” she asked.

“A lot. Can I do anything for you?”

“No, I don t even know what to think about what you just did..”

The next day I avoided her for a while. When the family was playing board games, I went outside and just watched the moon. After a few minutes, Michelle came out to meet me. “You ok?” ataşehir escort bayan she asked.

“Yes. I was just thinking about last night.”

She laughed in her own strange way, reflecting on what happened. “Don’t worry about it. But we can’t make it a habit. It’s just the circumstances. I’m sure you do that all the time. We just happen to be sharing a bed.” I agreed with her and gave her a hug, thinking about what might or might not happen that night.(

After we both washed up, we were in the bedroom alone, left to purportedly sleep there. I started playing with a deck of cards knowing full well I couldn t sleep. I have a feeling you’re not sleeping. You want to play a game?” she asked me.

“Sure” was my answer. I could see her full breasts taking over her shirt. “What did you have in mind?”

“We’re both grown ups. Maybe we should take some time getting to know each other” she answered. “As lame as this may sound, how about truth or dare?”

“Sure,” I answered, “as long as you go first.”

“Truth,” she said. She was kind of bouncing up and down on the bed.

I really had no idea what to ask or where to start. Should the first question be sexual or about something else? While I was thinking about the perfect question, she sort of helped me out. “Ben, I have no idea what the future holds, but ask me anything you’ve been wanting to know. I’ll be honest. You might not have another shot.”

I hated that she said that. She knew she had all the cards, but there was nothing I could do.

“How often do you masturbate?” was about the best I could come up with.

“Depends. Sometimes rarely, like when I’m busy and I have stuff going on. But when I’m bored, there have been days where I may just keep going and going and going.” She laughed. “I get off extremely easily, I think.” “How many times do you do it?”

“It’s not your turn,” I told her.

She laughed and then gave me the truth or dare question. Being a little uptight about all of this, I went with truth.

“Have you ever fantasized about me when you’ve um, played with…”

“Masturbated?” I finished her question for her.

“Yeah, but masturbated seems so clinical.” She sat there a second. “So have you thought about me?”

I really was lost in what I should say. I got up, going for my suitcase, which had a bottle of cheap booze in it.

“Get back here. You can’t avoid the question.” I took the bottle of tequila and sat back on the bed. I drank a quick swig. I handed it to her and she did the same, then put it down.

“Have you ever thought about me when you’ve touched yourself? Aside from last night, of course.”

I couldn’t look at her, and I still don’t know what I was thinking. I said yes, barely able to make eye contact with her.

Michelle got so excited, not in a sexual way, but more like a kid who just heard a big secret. “Really, tell me!” she demanded.

“It’s not your turn,” I said. This was the first time as to what was happening was dawning on me.

“Truth or dare?” I asked.

She thought it over for a second. “Dare” she said.

“Take off your shirt,” I told her knowing that she had nothing on underneath. I’d been staring at those rock hard nipples for the entire evening and needed to see them. Although it was a bit bold of me to ask, it felt completely natural.

She took off her shirt in a quick turn and I stared at her perfect breasts. They were round and so incredible my entire attention was fixed on them. “Your turn” she said.

I said “Dare” more out of curiosity of what she was going to ask me than anything else.

“If you’ve been lusting over these, come here. You can suck on them if you want.” I wasted no time but wanted to make it look like I was still playing the game. I took her left breast in my mouth and played around with areola and then moved to the second. I was fulfilling my adolescent fantasy. I sucked on her right breast for a while. This was something I had wanted to do for ages. I never wanted this to end. She moaned a bit, but I could see she was getting anxious.

“My turn” she said as she pushed off me off her breast. “Truth.”

“What is escort kadıköy the kinkiest thing you’ve ever done?” I asked. I truthfully wanted to know just how much she had done in her life. I wanted everything. This evening could never end, as far as I was concerned.

“Probably this.” She answered. “Your turn.”

That didn’t work for me. “Besides this.”

She did the same thing she did earlier, kind of bouncing up and down in her seat as she was thinking over what she was saying.

“This may come as a shock to you, but there is probably nothing I haven’t tried, and I don’t just mean the usual.”

“That’s not an answer. You have to elaborate.”

“Why don’t you ask me more specifically? I love to try new things, so I’ve probably done a lot of stuff that would downright shock you.”

One of my oldest fantasies has been anal sex. My current girlfriend is against it, but I’ve had plenty in the past who have liked it.

“Do you like anal sex?” I asked her.

“You know what’s funny about that? That used to be such a taboo, but now it’s completely accepted in our society. You know my friend Bonnie? She still considers herself a virgin even though she lets her boyfriend do it to her.”

“But you didn’t answer my question. Do you like it?” “And tell me some personal experiences with it. Not just yes or no.” I really wanted to know.

“Actually, this sounds weird, but I love it. I think I sometimes prefer it to real sex. The first time I did it was with Paul. I didn’t like it, but didn’t consider it real sex, so I let him do it all he wanted. It’s one of my favorite things. I’ve even used my fingers to go up my ass every now and then. How’s that for personal? Now your turn. Truth or dare?”

I was starting to get bold. “Dare” I replied.

“I want you to take out your package and play with yourself.”

I was so hard it wasn’t much of an issue, so I pulled it out and did just that. “Your turn, truth or dare?”

“Truth.” I was surprised but was fine with it.

“Have you ever thought about me when you’ve played with yourself?”

She thought it over. “Just so you know, I love to touch myself. Even when I’m with somebody. But yes, I have. That time we were living together. You’re a great looking guy. Sometimes things as simple as kissing. Sometimes very, very perverse stuff.”

“Give me an example.” I told her.

“It’s not my turn,” she said. “What about you?”

“Truth” I said. I was still playing with myself and enjoying it very much.

“If you could do anything you wanted to me. No repercussions. What would you do?”

“It depends on my mood,” I said which was the truth. “Sometimes things pretty tame, but I like very dirty things. My mind goes in some crazy directions.”

“How about now?” She spread her legs and started to play with herself over her underwear. “And to save you a question, the most common way I touch myself is over my panties, but I do it all.” I hope you don’t mind if I touch myself. “And, if you were thinking about it, I am incredibly orgasmic. I can cum from simply having my nipples touched. I could have if you kept sucking on them.”

“You want the most perverse thing I would do to you?” I asked.

“Yes, you’re supposed to give me truth. So tell me.”

I looked her over a bit. “Can you take those off? I want to see all of you.” She took off her underwear, which were pretty much not there anyway. She had pubic hair, which seems to have gone out of vogue lately.

“I would turn you over and fuck you up your ass.”

She turned over and showed me her tiny ass. Fuck, she is a small girl. Taking her fingers in her mouth, she pushed them up one by one.

“I have 3 fingers in my ass. What would you have me do next? Pound me until you came?”

“No,” I replied. I would pound you for a while. But just before I was ready to cum, I would take my cock out and put it in your mouth.”

“Like this?” She started sucking on her fingers one by one.

“Yes.”

After sucking on my fingers, she turned over and sat back down as if nothing had happened, smiling. “I guess it’s my turn. Truth again.”

“Tell me the absolute most disgusting, bostancı escort crazy thing you’ve ever done. Even if you wouldn’t do it again.”

She thought it over, once again bouncing again. It was hard to believe that this was the same girl who just sucked on three fingers coming out of her ass.

“It’s pretty bad.” She said. “Definitely not conventional.”

“I don’t think any of this entire night is conventional.”

“That’s true. Ok, I’ll tell you. Brad, the DJ guy I used to date, took things to another level. He enjoyed peeing on me. Eventually, he convinced me that urine was sterile and I would drink his pee. It still grosses me out, but I did it.”

“I was expecting you to say you had a threesome or something” I said as I laughed.

“I’ve done those too. He would take those pretty far too. So I’ll tell you cause it’s kind of on the same tip as what I just said. This totally grossed me out, but I did it for him. He worked in entertainment, as you know, and these girls used to come by. As he loved anal, many let him. He loved it when I would suck him off after he was inside her ass. I try not to think about it, but I did do it.”

“Wow” I said. “I thought I’ve done some crazy shit.”

“I’ve told you a lot. So truth or dare?”

“Truth.”

“Time for a two parter. I just gave you that. Sound good?”

“Sure. What do you mean?” I asked.

“Truth and dare, ok? But you have to be as honest with me as I’ve been with you.”

“Deal” I said eagerly.

“The truth part is first. If you could do anything you want with me. Your ultimate fantasy, what would it be. No restrictions and knowing what you know now. No judgments. You have free access to do anything you want.”

“Total truth?” I asked, just making sure.

“Nothing but it. Anything.”

I thought it over for a second. “I’d like to spank you a few times so it hurts, then fuck you hard up your ass. Every few minutes I’d take it out and have you suck on it. If you are really into it, I’d like to piss in your mouth and have you swallow it. I know it’s gross. I don’t even know why I’m thinking about it.”

“Cause I brought it up. So now it’s dare. I dare you to do all those things to me right now.”

“Are you serious?”

“It’s a dare.” You can’t back out now.

I walked over to her. There was a different look in her eye. One of pure lust. She looked up at me. I pushed her down and spun her legs down. Her ass was right there. It looked so small. I couldn’t believe all she told me.

“Don’t be shy. Do it exactly how you would want to do it.”

I pushed my dick in her dry ass. She yelped and grabbed the bed. I started pounding away but it didn’t feel so right. “Stop” she said. I pulled my dick out and she turned around and sucked on it. “Isn’t this what you wanted too?” We need to get it moist. She sucked my dick like a pro.

“Can you taste it? Do you like it?”

“I can taste my dirty ass. I’m your whore tonight.”

She smartly slobbered all over my cock and turned over. I pushed it back in a lot easier. “Slow” she said. There were tears falling down her cheeks as I pounded her.

“Play with yourself,” I told her. She started to touch herself. I love the feeling of how it felt when she put a finger inside herself and I could feel it up her ass. She got more and more turned on.

“I’m about to cum. Sit down” she told me. I did as she said and she ground her ass all over my pelvis. I could feel the muscles contracting as she came.

I pulled out and brought my dick back to her lips. “Mmm, so good. Where do you want to cum?”

I thought about it for a second and put my dick back in her ass. This time I pounded away as hard as I could. She almost was screaming. As I felt my orgasm his, I pulled out and put it in her mouth. She swallowed all and then licked my dick clean with those huge lips, never even letting the cum escape.

“How was that?” she asked.

“The best ever.” We walked to the bathroom together to clean up.

“Whenever you are ready again, I’m right here.”

I thought about what she told me earlier and told her to get on her hands and knees. I took my half hard dick and put it in her mouth. After a second to get used to it, I started peeing. She drank it up without spilling anything, just smiling the entire time.

I was half hard again instantly. “I think this is going to be a long week” she said.

To be continued…

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