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My Sister's Special Request

My Sister's Special Request

by Strongnsensual
19 min read
4.69 (121000 views)
sisterbrothershared wifeanalanal sex
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Everyone is over 18 at every point mentioned in this story. It's a fantasy word folks - hope you enjoy it!

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"Scott wants me to cheat on him."

"What? That's nuts -- why would he think you're cheating on him?"

"I didn't say he thinks I am, I said he wants me to. He's practically demanding it."

"Um, wow, that's -- I don't know what to say. I'm so sorry Debbie. What are you going to do? Counseling?"

"Have you ever known anyone who was really helped by counseling?"

"No. So's this the end?"

"I don't want it to be -- he's my husband, and I love him! I just -- I don't know."

"Sheesh Deb. Wow. I -- wow."

"I just needed to tell someone I trust. I don't know how this is going to -- what's going to happen."

"Are you -- are you considering it?"

"Maybe. No. Fuck, I don't know. He really wants this, bad."

"Why? That's so weird."

"He says he was watching some show, and they used a word he'd never heard, so he looked it up. Then he turned off safe search, and now he swears it's the sexiest damn idea he's ever heard of. He keeps saying 'do it for him.' He says it's about being married to a woman so sexy she can have whoever she wants, an adventurous -- well, he says slut like it's a good thing. A very good thing."

"And how do you feel about all this?"

"I don't know. It's good to be able to talk it through. Thanks for letting me vent, even about sex."

"Well, I have heard of this, but I never knew for sure if it was real. And you're my sister, if you need to talk I'm here for you."

"Thanks Jason. So, have you played any golf yet, it's been nice and warm for a while now." She changed the subject, and I was relieved. I wanted to be there for her, I wanted to help, but holy hell was it awkward! Didn't she have a girlfriend she could talk to about it?

When the coffee was done Deb got up to leave. I walked her to the door. She gave me a big hug and said "thanks for everything -- it feels better having talked about it. Love you Jason."

"Love you too Debbie."

I closed the door, and stood there wondering if my sister was going to have an affair -- because her husband insisted! She'd never been a prude or anything, but this was pretty crazy. I needed to clear my head, so ten minutes later I was wheeling the bike out of the garage and heading for a good, twisty back road. It did me a lot of good.

I had just about forgotten that crazy conversation when Debbie called one evening. A few weeks had passed. Soon she was at my door.

"He's serious. He's obsessed, actually."

"Oh" I said. 'This again?' I thought.

"Can I have a beer?"

"Sure, I'll join you."

I grabbed a couple of Fat Tire beers and opened them. We sat down on the couch, and Deb took a long swig.

"Jason, I'm starting to consider it."

"Wow! I mean, okay. Tell me more." I had to force those last words out. She clearly needed to talk.

"Thanks Jason. God I love you. I really need to talk this through. He won't let it go -- he's been impossible to live with. He found some group on line, and he swears it will bring us even closer together, and I don't know about that but I'm sure he's completely convinced. I'm -- I'm thinking about it."

"I understand." 'Liar!'

"He says it's a gift he wants to give me, for me to have more pleasure, and it's about trust. He says if I do this he'll know I trust him, and he'll be showing how much he trusts me. He says he wants to watch me get dressed up, then wait until whenever I come home."

"And you can't just go out, mess up your hair and come back."

"No, that won't work. He -- he wants to see evidence."

"Well, you could throw away your --"

"He wants to see some very personal evidence."

"Um..."

"In my pussy."

I sat there and blinked a few times. I wanted to be there for Deb, but holy shit was this getting weird. Debbie finished her beer.

"Deb, I --"

"Jason, I want you to have me."

"WHAT!? Debbie!"

"Just listen, listen okay? He wants this, I know he's not going to give up, and I don't want this to ruin my marriage."

I chuckled at that before I could stop myself.

"Shut up. I'm not going to hang out in bars, I'm not joining some web site, I don't want to get a reputation, he doesn't want to watch, he just wants to wait for me to come home, and I love you and I trust you so please just do this for me?"

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"Do this for you? You mean -- Debbie, I just can't!"

Holy shit, her lip trembled. Oh fuck.

"You won't help me? Jason, I don't want to lose my husband, everything is consensual, and -- and I know you used to peek at me in the shower. Aren't I sexy any more?"

Fuck fuck fuck. I never knew she knew about that. I stared at my sister. She stared back through damp eyelashes.

"Is that it? I'm not sexy? I don't turn you on? Maybe that's why Scott needs this. I'm not enough for him just on my own."

She caught her breath a few times, like she was starting to sob. I put down my untouched beer and pulled her to me in a hug. Hopefully a very brotherly hug. She wrapped her arms around me and just held still. I tried to think. I wasn't going well -- my mind was racing. My sister actually wanted me to have sex with her! And she knew about the peeking when we were in High School!

After a few insane minutes she said "just tell me you won't push me away Jase. Please?" Her voice was thick with impending tears.

"Of course not! You're my sister!" She smiled, and gave me a peck on the lips.

Here's where it all went sideways. I should have turned my head, I should have -- well, I should have done absolutely anything but let her kiss me on the lips. But she was quick, and I was worried about her feelings. When she realized I wasn't going to reject her kiss, she took advantage of the situation. Her tongue slipped between my lips. But what shocked me even more was her hand; she grabbed mine and pressed it to her tit. I felt her nipple harden under my palm before I could pull away!

I leaned back. My head was spinning. Debbie was staring at me, her chest heaving. Then she swept her arms up, taking off her top! I realized I hadn't felt a bra as her gorgeous chest sprang into view. I couldn't help but stare. Who knows what I'd have done if I'd had as much beer as she had!

"Are they sexy?" she asked, pressing her breasts together to show off their luscious size.

"I -- uh, holy shit Deb, I --"

"Come on, did you peek just because you were curious, or because you wanted more than you saw when I was in a bikini?"

Holy fuck, she was reading my mind.

"Want to know something?"

"Uh, what?" I was still staring at her breasts. I couldn't help it. They looked even better than they had in the shower all those years ago.

"I liked it. I loved knowing you wanted to see me naked. I kept wishing you'd do more." She put her hand behind my head and pulled me toward her breast. The pressure broke the spell that locked my eyes on my sister's nipples.

"Deb, I love you to death -- but I can't do this! You're my sister! You're hot as fuck but you're my sister!" Oops.

"Hot as fuck? Wow!" She beamed, and suddenly yanked down her yoga pants. My eyes followed her motion and I saw her mound.

"Do you like it? I shaved it for you. No one else has seen it like this." She pushed her pants down farther.

"Deb, I -- this is crazy!" I said, backing up along the couch.

"Come on Jason, I need your help. And I don't have to ask if you think I'm sexy. Not any more."

I wondered what she meant for a split second. She reached out and rubbed my boner. Holy fuck, I had a raging boner. Shaved women always do that to me, but I'd have thought my sister would have been the exception. Apparently I was wrong. But this was wrong.

"Look sis, I love you, but -- I can't do this."

"Please? You promised you'd help me! You're not going to reject me are you?"

Fuck, had I said that? It was hard to think with that shaved vagina on display right in front of me. She knew it, too. She ran a finger between those shaved lips, teasing me. It was working. I had to do something. I stood up -- which was not comfortable in my suddenly tight jeans by the way -- and backed away, saying "I love you sis, you're gorgeous, but I -- I need time to think, okay?"

Her trembling lip had been replaced by a determined gleam in her eye. I should have realized how much trouble I was in.

"I suppose I can understand that" she said with a little smirk. She kept her legs spread, and her finger hadn't stopped moving. Her eyes hadn't left my zipper either.

"Thanks. I want to help, but I can't help this way."

"Sure, no sweat." She sounded casual and relaxed all of a sudden. She smiled, and pulled her pants back up. "Can you get me my top?" I looked around my living room. She must have thrown it when she pulled it off. It was draped over the arm of the recliner. I got it for her and handed it to her.

"You don't have to stay two arms' lengths away, I'm not going to jump you" she said with a grin.

"I'm not so sure."

"Stop it. You said you needed some time, that's perfectly reasonable." She pulled top on, found the remote, and turned on the TV. She patted the couch next to her. I sat down. It took a bit of time before relaxed. She hung out for a while. When it was time to go, I got a sisterly hug and a peck on the cheek. She didn't say a word about exposing herself.

I had trouble getting to sleep that night. An allergy pill did the trick, after an hour or two of tossing and turning.

I was groggy all the next day. Thank God for coffee. I stumbled through somehow, and was dozing on the couch after dinner when my phone buzzed. It was a text message from an unfamiliar number. I opened it, and there was a picture of a woman's breast, with a hickey just outside the areola!

I was starting to type "who is this?" when some text came through.

"He loved the hickey you gave me. He's so happy, and so am I! This is going to be incredible!"

"You have the wrong number. Really hot though!" I sent.

A few seconds later, another photo came through. This one was a woman's fingertips and pussy. Her red fingernails were shining as she held herself open for the camera.

"And now I'm really glad you have the wrong number hot stuff!" I hit send, and then my hands started shaking. I realized what was happening.

"He's so glad you're turned on, and so am I!" Wink emoji. "He loves not having the slightest idea who you are! I haven't seen him this happy in months, and I'm even happier!"

"You've got to stop this."

"You've got to get inside me."

"No."

"He can't wait to see you dripping out of me. I can't wait to feel you put it in. He's promised he'll never ask who you are, its perfect!"

"No."

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"Hang on he wants to say something" came the next text.

"Please fuck my wife. What do you mean no? do it. We both want you to. What's wrong with you?"

I tried to think of something to say. Finally I typed "she's married." There was no response for a long time, then another photo came through. It was my sister, full length, fully nude, in a running shower. Her hands were up in her hair, her breasts looked magnificent, and her legs were spread. She was staring into the camera, biting her lip. I moaned when I spotted a pair of white sneakers by the shower door, with a pair of feminine looking socks tossed in front of them. They looked similar to what my sister had worn in high school. Fuck, I realized I had a boner.

"She looks hot, doesn't she? I don't know who you are and that's perfect. It makes it easier to tell you to fuck my wife. I'll just stay home while she's on her knees for you. I'll dress her up for you and send her to you to fuck. No protection ever. Fuck her. You have it in writing. She was reluctant at first but now she wants it more than I do and I love that."

Holy shit was that a lot to digest. I scrolled back up to the shower picture again. I suddenly realized I was rubbing my dick. The phone buzzed.

"See you soon lover."

I set the phone down, then picked it up and turned it off. Then I went to bed. It was hopeless. I couldn't sleep. I took an allergy pill that always knocks me out. No good. I just laid there, wide awake and incredibly horny. I decided to take the obvious measures. I was already hard as steel, so I began stroking. I was severely tempted to go get the phone, and stroke to the pictures. That fucking phone was calling me! I pushed myself down against the bed, fighting the desire and started to feel like I'd won when I realized I was kidding myself. I didn't even need the actual photo -- I could picture every detail as clearly as if it were right in front of me.

As if my sister were right in front of me. I could picture those innocent looking shoes, her long legs, the swell of her hips, and -- oh fuck she shaved for me! For me!" I was cumming, jets of sperm shooting into the air. A few actually went over my head, I exploded so hard. I was picturing my sister as I exploded. Holy fuck was this wrong, but also incredibly hot.

I woke up a couple of hours later, I'm guessing. I got cleaned up, wiping some dried cum off the headboard, and crawling back into bed. I had some crazy dreams.

When I woke up in the morning, I had a cup of coffee and found my phone. I turned it on and saw I had several more messages.

"Can't wait to have you inside me lover" followed by a picture of her fingers inside her pussy. Then, a while later, "talk to you soon" and a kiss emoji. Finally "I. Want. You. To fuck. My wife."

Sheesh. They were all in on this. And obviously part of me wanted it to. Well, one specific part with very poor judgement and no morals....

A few days passed, and there was a knock on the door. It was early evening, and I was just about to fix some dinner. I was thinking my usual bachelor chow, cubed beef, rice, broccoli and brown gravy. Hey, if they called it "Qua Fae Sum" or some shit people would say it's cultural and classy, don't judge me. There was a knock at the door. Debbie was there, with a pizza and a six pack of beer. Good beer, too, a Kona Brewing lager she knew I really liked.

"Come on in!" I realized I was suddenly nervous.

"Thought I'd give you a little surprise!" she said, prancing in and setting the pizza box on the coffee table. "Here" she added, handing me a beer. It was cold. She got one for herself and I got out my pocket knife. When the beers were opened she clinked the necks and took a swig.

"So what's up?"

"Nothing at all, I was just about to make some dinner."

"My timing is perfect then! Hey, have you seen that new motorcyclist movie?" I had, but she seemed to want a dinner and a movie evening. "Happy to watch it again!" I said.

She found the remote and set about finding the movie. I got us some napkins and plates. When I came back, she was sitting on the couch with her legs on the coffee table. I recognized the sneakers she was wearing.

"Got it cued up!" Speaking of cues, I was taking mine from her, almost warily. But she acted completely innocent and sisterly-ish. So I settled in next to her -- close enough to show I was comfortable (liar!) but not far enough to seem like I was avoiding contact. I looked at her out of the corner of my eye. Apart from the very obviously deliberate choice of footwear, she was dressed very innocently. Shorts that weren't tight, a blouse that buttoned up the front -- and it was actually buttoned. Well above her cleavage. Well, where her cleavage would have -- fuck, really boner? Anyway, she was dressed like a girl coming to see her perfectly normal brother. Okay.

I opened the pizza box. Pepperoni, mushrooms, and anchovies on half. Boy, did she know her brother. I put a couple of fish-free slices on a plate and handed it to her. I got some anchovied goodness onto my own plate and settled in to watch. When she had finished eating, she moved a bit closer, but didn't make any suggestive moves. Good thing I'd already seen the movie, because I was not paying any attention to it at all. It must have been obvious, because after a while Debbie smacked me on the shoulder.

"Would you relax bro? It's like leaning on a fence post. A very tense fence post."

'Okay, fine. I'm not going to be the one to make this awkward' I thought, and pushed everything out of my mind as best I could. I must have succeeded. There were no more slaps or comments, anyway.

We'd each had a couple of beers by the time the credits rolled.

"That was good -- was the riding realistic?"

"Yeah, good enough for Hollywood. It's not a bad movie."

Deb got up, and carried the pizza box and leftover brews into the kitchen. I heard her open the fridge, shuffle some things around, and close it.

"I'd better get going. Thanks dude, this was fun."

'Really? That's it? Just a normal night together, brother and sister? Awesome.' I really felt relieved.

She gave me a peck on the cheek and she was out the door. I was feeling great. Very relaxed. I got a few little things done and was getting ready for bed when my phone buzzed.

"She's so hot, so happy -- thanks. I mean it." Text from the unknown -- but not really unknown -- number.

I couldn't come up with an appropriate reply, so I didn't respond. The phone buzzed again. It was Debbie. "Fun evening -- we need to do it more often."

What had she told Scott? Oh well, I was happy, she was happy, he was happy... why question it? Maybe she'd given up on this crazy idea.

When I opened the door the next Friday night, I was happy to see Debbie again. She had a paper bag in her hand, and another six pack of beer. Amber ale this time, with an alien on the side of the package.

"Got plans?"

"Now I do!" I said with a smile. I threw the door wide open and waved my arm to welcome her in in formal fashion.

"Is this going to be every week? Not a bad idea!"

"Could be, let's see!" She set the food on the table again. Once again, I got some things from the kitchen. We settled in, and she turned something on. On the TV I mean. After a while, some iced tea I'd had earlier conspired with the beer to send me off to the recycling center halfway down the hall.

When I came out of the bathroom I got an incredible shock. There was Deb, on her knees, completely naked. Over her shoulders I could see the white tennis shoes that had been in the shower photo. Before I knew it my shorts were down and I was growing in her mouth. I had no chance to object, must less react. My dick betrayed me.

I've had some great blowjobs before, but Debbie was making love to my dick with her mouth. She grabbed the base of my rod and had me deep in her mouth in no time. She sucked like she was trying to pull the air out of my lungs, and she did. I gasped, and clung to the door frame to avoid falling over. I was fully erect in seconds. I didn't spot her phone until she reached for it. She looked to the side with my shaft in her mouth, I felt something odd, and just like that she had photographic evidence.

She didn't even take me out of her mouth as she raised the phone so she could see the screen. How the hell could she type and suck so well at the same time? I realized she was sending the photo. Fuck. The phone rang. She answered it, still without breaking the liplock around my cock.

"Mm-hmm. Mmmmm, mm-HMM."

There was a pause while she listened to whatever he was saying. Her mouth didn't pause the sucking though.

"Oh, you want me to say it out loud? Absolutely. I'm naked on my knees. I'm sucking his dick. I'm going to swallow him. I'm his slut."

"Anything he wants. I won't say no -- anything."

"No, I'm his slut. His slut."

She stared up at me as she listened to the next question.

"Right. Down. My. Throat. No, because I am desperate to taste him. I'd swallow even if you begged me not to. Yeah? I told you, I'm his slut. That means I swallow for him."

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