Helping Each Other Out

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As these things so often do, it all began over a few beers.

I was sprawled casually on one end of the couch that afternoon, watching some game on the TV and working on my second bottle of beer. My wife was out doing her Christmas shopping meanwhile and I knew there was no point in expecting her to come home anytime in the near future as she was such a very careful shopper. I was not alone however as my sister-in-law had come over to stay with us over the holidays rather than go home and have to deal with her very conservative, bible-thumping parents.

I sympathized with her completely — I’d met my in-laws, after all — and did not object to her practically moving in with us for a few weeks.

What surprised me was that Emily had taken a seat at the other end of the couch and was at least pretending to watch the game. I knew full well that she had absolutely no interest in college football and was noticing how she kept shooting sidelong looks at me without ever saying anything. I would later suppose that she needed a little time to work up the courage … or for the booze to lower her inhibitions enough.

Finally, she leaned over and gave me a nudge.

“Hey, Will” she said casually, as if this was the most normal thing in the world to ask someone. “Aren’t you kinda into anal?”

Naturally, she’d managed to say that just as I was taking a gulp from my beer so that I choked on it, coughing and sputtering as I nearly dropped the bottle. Wiping my mouth with the back of my hand, I gave her an astonished, even incredulous look. “I beg your pardon?!”

She shrugged, pretending to be innocent of just how odd it was to ask someone a question like that right out of the blue. “I just thought you might be. Brenda was telling me that you must have asked her a hundred times if she would let you fuck her ass. Just between you and me, she thinks you’re a little bit of a freak on that subject.”

I grumbled softly to myself, not for the first time wishing that my wife would learn to keep her mouth shut. That woman had a very bad habit of telling her little sister absolutely everything no matter how private or personal. My cheeks reddening, I knew there was no point in trying to tell Emily to mind her own business.

“Fine. I have fantasies of … doing stuff with my Brenda’s bottom. So?”

She raised her bottle and had another gulp. “But she won’t let you. She thinks it’s gross and nasty. That’s what she was telling me anyway.”

I raised my bottle too, hoping to hide some of my embarrassment over this weird conversation behind it. “Yeah, that’s what she told me, too.” I tipped my bottle back one last time, finishing it off, before asking again, “So?”

She shrugged again, keeping her eyes on the TV and carefully avoiding my gaze. “I just found your situation sorta interesting …”

As her voice trailed off, I set my empty bottle aside and took a closer look at my sister-in-law. She was nervous about something, I noticed with a start. He wondered again where she was going with this weird and awkward conversation.

“Oh? Why is that?”

She took another gulp of beer, keeping silent for a moment. “Rain can be kinda slutty and is always bragging about what she does with her guys. I mean, she just cannot shut up about it! Anyway, she says she loves it when the guys eat her ass or stick their dicks in it.”

I knew who she was talking about, of course.

Like Emily herself, Rain was a junior in the local college and my sister-in-law’s roommate in the dorm. The young woman’s real name was Lorraine, but she hated her given name with a passion as she thought it far too traditional, far too normal. She was covered with tattoos and piercings and had quite an attitude, all of which was a real turn off for me. Not even her porn star-sized tits could make up for so many shortcomings.

Emily continued, “Anyway, she’s spent so much time gushing about it that I’ve gotten sorta … curious about anal.”

I nodded slowly. I was starting to get an idea of where she might be going with all of this, but I just could not believe it. No, it simply wasn’t possible. I had to be mistaken. So, instead of jumping to an impossible conclusion, I ventured the more obvious ones first.

“So, you’ll be having a little talk with your boyfriend then? I’ll bet he’d love to try something new with you.”

She groaned, sounding annoyed. “You would think so, wouldn’t you? But no! That idiot George agrees with my sister, says that anal sex is nasty. Sure, he’ll grab my butt all day long, but he won’t so much as stick a finger in it.”

“That’s too bad.”

Well, that was one of the two obvious solutions down, I thought. Now to try the other. “Why don’t you tell Rain about your problem? You can’t tell me that a girl like that would have any problem with it. She’s probably got a nice selection of toys, too. Or you could ask her to introduce you to one of her more anal playmates.”

She scoffed. “Will, Rain may be one of my best friends, but I’m not about to get busy with her. She says she always and only has safe sex, but that woman almanbahis gets it so often that I cannot believe that she doesn’t have some kind of … germs floating around in her. And if she does have something, I’ll bet all her men have it as well.” She took a drink from her beer. “And dildos? What would be the point? I mean, sticking something inanimate up my ass isn’t going to tell me what I want to know. I’m looking for the real thing, you know? There’s nothing that can match the real thing.”

A heavy silence fell over the room then, each of us lost in their own thoughts.

That sort of left me with only the impossible option. Since we both had the same problem, could she really be working her way towards suggesting that they sort of … try it out … with each other!? Surely not! She and her sister were so very, very close that it was just unimaginable that she would ever even consider fooling around with her husband. No, I had to be missing something here.

“Hmm. Sounds like we have the same problem then.”

She took a deep, calming breath, gulping down the last of her beer for some of the ol’ dutch courage. Setting down her empty bottle, she turned to face me at last. “So …” Her voice was soft and hesitant, her manner nervous and cautious. “So, maybe we could … help each other out?”




I gave her a very startled look. “Em …!”

“Don’t get any ideas!” she said quickly, waving a warning finger in my face. “I’m not trying to suggest we have an affair of anything. I wouldn’t do that to my sister. Not ever!” She took a deep breath to calm herself, then added, “All I’m saying is that we try this once and only once so we can both find out what it’s really like. After that, everything goes back to normal and we never speak of this again.”

I just stared at her blankly, my mouth hanging open, hardly able to believe that she had really just proposed such a plan.

“And we don’t do anything except the anal. That’s what this is about, after all.”

Pulling myself together as best I could, I shook my head at that. “Can’t be done. It’s not like I can just snap my fingers and suddenly have an erection that I’m ready to stick into someone.” She looked more than a little doubtful at that claim. Her experience with men told her that they got hard and were ready to go at the drop of a hat, but she could hardly argue with his next comment. “Come on, if we’re going to do this, you cannot tell me that this wouldn’t go better for us both if we were … aroused.”

Emily hesitated, clearly hating the idea of betraying her sister and yet consumed with curiosity. “What exactly are you suggesting?”

“Just that we should start with a little oral to get us both in the mood.”

“And then the anal, right?”

“Right. And then we never speak of any of this ever again.”

She hesitated for another long moment, then nodded firmly. “Okay then.” She looked to the clock on the wall. “Well, if we’re going to do this, let’s do it now. We should have more than enough time to do this and get cleaned up before Brenda gets back.”

I needed a moment to think, The idea that I was sorta kinda being propositioned by my wife’s younger sister was simply unbelievable! The prospect of finally being able to make my fantasy of having anal sex was just incredible. And the thought of actually fucking this cute college girl’s tight little ass was … okay, ridiculously hot.

“Okay. I’m in.”

She climbed to her feet and started unfastening her belt and opening her tight pants, her hips swaying right and left as she started slowly pushing them down. She then bent forward to slide them down her legs.

I didn’t even try to hide how closely I was watching all of this. I’d seen those long, smooth legs plenty of times before of course when my sister-in-law wore shorts or her swimsuit, but they had never incited much of a reaction in me before. Emily was just my wife’s little sister after all and I was far too in love with Brenda to even think of running around on her. Now though, those long, smooth legs were especially fascinating somehow.

It made my cock start to stir to life and naturally I used every trick I knew to keep myself from getting hard. The last thing I wanted was for her to see me with a full erection and imagine that we didn’t actually need to have the oral we’d agreed on. No, I wasn’t fighting myself to have a sexual experience with a woman other than my wide, just trying to avoid a misunderstanding.

Instinctively, I reached out to help her pull her pants off, my fingers brushing against her bare skin. That made her yelp and jump a step out of my reach, swatting at my straying hand.

“NO! I can take off what I have to all by myself. You just get your own pants off!”

I immediately withdrew that straying hand with an apologetic wince, chastising myself for not thinking. I was not having a romantic encounter here, not having an affair, and really I was not cheating on my wife. No, this was just two friends doing each other a little favor and nothing more.


She almanbahis yeni giriş turned to give me an expectant look then, crossing her arms as she waited for me to follow her example. I just smiled and unfastened my jeans, lifting my butt off the couch briefly to push them down. I had been doing some working out recently to stay in shape for my wife and so Emily’s breath caught when she got a glimpse of how how much it was benefiting me. Or maybe, it was because of the size of the bulge she saw in between those muscular legs?

Either option did nothing but good things to the ol’ ego.

She had gone first when it came to our pants and so I silently insisted that I should go first in the removing of our undies. Lifting my butt again, I scooted my tighty whiteys down and slid them off, tossing them over onto the pile of clothes that was growing beside the couch. My semi-hard cock came springing out into the open then of course and I noticed with a wide, pleased smile how she was staring at it, licking her lips.

“You like it then?”

She gave a little start at the sound of my voice, looking a little guilty. “Well,” she hedged awkwardly, suddenly trying to look anywhere but at my dick, “it’s not as thick as George’s, but it looks like it may be a little longer.”

I almost laughed. “Just this once, it’s perfectly okay to look at your sister’s husband’s cock, Emily. It’s about to be in your mouth and then your butt, after all.” She gave me a little smile and laughed at her own silliness as her eyes did go back to my manhood. “And I suppose it may be a good thing for I’m not so thick. Maybe it means I’ll go in easier and it won’t hurt.”

I could have kicked myself for saying that. The last thing I wanted to do was scare her off by reminding her of all the tales out there of how much it could hurt to be fucked in the ass.

She just nodded absently though, her eyes never leaving my dick for a moment. “Yeah,” she breathed softly. “Maybe …”

“Emily?” She didn’t react at all to my gentle voice, so I tried again. “Emily, it’s your turn. Time to lose those panties.”

She shook herself free of the spell she’d been under with a self-deprecating laugh, running her fingers through her hair. “Sorry, Will.” she said shyly, meeting my eyes again. “I was just thinking …” Her face went a bright red and she was quick to shut her mouth and get to work on her underwear.

My cock jerked happily at all this flattery, getting harder no matter how hard I might have been fighting it.

Turning away from me as she grabbed both sides of her panties, she bent forward as she pushed her panties down her legs, turning them inside out in the process. She obviously wanted me to look at her bare bottom and I took full advantage of the opportunity. Her bubble butt was impossible to hide using only a pair of pants of course – especially the snug kind my sister-in-law preferred — but the sight of it exposed in all it’s glory had me drooling.

So tight, I panted. So sexy. So much nicer than Brenda’s, especially since my wife hadn’t yet joined me in working out …

I shook that thought out of my head determinedly. This wasn’t a competition! Brenda was the woman I loved with all my heart and Emily was just a friend. My sister-in-law and I were just doing each other a favor, nothing more. We were absolutely NOT cheating on Brenda by doing this, merely helping each other out.

However, thoughts of my wife were soon driven from my head when I finally tore my gaze away from that perfect ass and spotted the damp spot on the inside of her panties. My eyes moved slowly up her legs and spotted a couple of droplets on the inside of her thigh. Taking a deep, steadying breath, gripping the arm of the couch firmly, I let my eyes drift even higher to see her cleanly shaven cunt. The labia already protruding.

Yeah, she was just as aroused as I was …

There was no way I could keep it down anymore and my cock was suddenly as hard as a rock. It didn’t help at all either when she looked back and took in my erection with a very happy grin and echoed my earlier question.

“You like it then?”

“God yes,” I replied in a low moan. “So very, very much.”

Emily was obviously pleased as her cheeks went a warm red and her grin transformed into a bashful smile. She thanked me by reaching back with both hands to spread her other cheeks apart to give me a better look at her little asshole. A low, hungry moan was pulled from my very soul and I really had to work to keep from jumping up and grabbing her.

It was clear to us both by this time that my claim that we needed some oral to get ourselves into the right mood was simply wrong — we were both not merely ready to go right now, but actually straining at the bit. Even so, neither of us were at all interested in suggesting that we should skip the oral.

She straightened up at last and turned to face me again.

“Um, so …”

“I guess we should …”



It was sort of uncomfortable to arrange ourselves into a sixty-nine there almanbahis giriş on the couch as it wasn’t long enough for us to really stretch out, but we managed somehow. I was on the bottom and had my head between her legs while she had my hard cock right in front of her face.

Suddenly, Brenda and George were the last things on either of our minds.

Reaching out, she ran a single fingertip slowly down the full length of my erection and couldn’t help but giggle when she heard a muffled moan from behind her, my cock jerking toward her eagerly. I was way too excited to play the tease too and responded by running my tongue slowly along her lower lips, separating them and dipping inside her. Emily’s giggles suddenly dissolved into a gasping cry when she felt that wet caress, but returned when she heard a murmured “Yum” come from between her legs.

Taking hold of the base of my shaft with one hand and cupping my heavy balls with the other, she started swirling her tongue around the head of my cock. She would next lavish a lot of attention on the shaft, licking and kissing it lovingly while at the same time stroking it up and down. She had me twitching and squirming happily beneath her well before she took the tip into her mouth to suck, much less before she lowered her head and took more and more of me into her mouth.

Again, I was much more direct, spreading her swollen lips apart with my fingers so that I could drive my tongue in deep for the tastiest nectar. I made sure to lick her pussy both inside and out, stroking and caressing her erect clitoris with my tongue, making her tremble with pleasure and excitement.

When I began to suck on that fat clit, her back arched and she was obviously straining to hold back her orgasm, especially after I sank one and then another finger deep into her honey hole and started pumping them in and out. Twisting my fingers to the left and to the right, curling them to tickle her G-spot, thrusting them in and out harder and harder, I gave her clit a playful little nibble and was pleased to hear her squeal.

It was I who had to beg for mercy though when she impressed both me and herself by sucking my entire dick down her throat and kept it there.

“Em? We gotta stop, Em.” My face was flushed with excitement and wet with her cum as I pulled it out of her cunt at last. “Emily? You’re gonna make me cum.”

For a moment, she didn’t see the problem. Taking my dick out of her mouth, she jerked it good and hard as she answered, “So? I don’t have a problem with swallowing, Will.”

I hesitated briefly, thinking how great it would be to just shoot my load down her throat – or even better, maybe all over her pretty face. My wife would never in a million years let me give her a facial and it was extremely tempting to find out if her sister was more open to the idea. Like she was more open to the idea of anal, you know? With a little groan of frustration though, I knew it couldn’t happen if I didn’t want Emily and I to come away from this with regrets instead of happy, pleasurable memories.

“Em, we really gotta stop. This isn’t about cheating on Brenda, remember? We just wanted to try anal.”

She sighed heavily and stopped what she was doing a little unwillingly, not releasing her firm grip on my meat at first. “Okay, okay. You’re right. I was getting carried away.” She climbed back off of me, looking back with a smile. “I was really enjoying what you were doing to my cunt, by the way.”

i thought better of admitting to her that I’d been doing the things that never failed to get her sister off, but returned the compliment. “Your no slouch at giving oral yourself, Em. I’ve never had a girl deep throat me before.” Rising unsteadily to my feet, i gave her a grin. “Your guy George is a very lucky man.”

She was obviously pleased. “Thanks.”

With her legs weak and her pussy thoroughly used, she didn’t even try to move very far. Moving around behind the couch so that she could bend over it’s back, she stuck her ass out invitingly, her legs apart. “Come on then, Will. Come and fuck my tight little ass.”

I had been waiting since puberty to hear a woman say that and it sent me lurching around the couch at top speed in my desperation to finally bury my meat in some ass. She laughed out loud at my enthusiasm, but it did nothing to diminish her lust to have her ass plowed. She looked back over her shoulder with a wide smile as I took up position behind her.

I just couldn’t resist and moved my hands in a gentle caress over her ass cheeks. It was so great to be able to touch a woman like this and not have her tense up. My wife knew my interests all too well by now and would always react with discomfort when I touched her butt, making me nervous and overly cautious. On the other hand, Emily just cooed with pleasure and instead pushed her butt back to get more of the same.

I was a very happy camper indeed.

Rather than try to stick my dick into her ass right away, I went down on my knees back there and took hold of her by the hips. I kissed her cheeks all over, working my way closer and closer to her crack as she sighed happily and started to wriggle helplessly. Breathing hard, her heart pounding furiously in her chest, she let out a little cry of pleasure as he next started to lick his way down that crack towards her sphincter.

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