Sister Fister

"You up? I need a favor" read the text.

It was past midnight, and my younger step-sis Holly was evidently awake too. I'd been lying in bed chatting with my college girlfriend Sam, who I was missing dearly over the Christmas break. I'd come home to have a family Christmas. It might be our last together as a family, as Holly had just turned 18 and graduated, and was about to leave home to spend some time in Prague, and at 20 I had already been gone a couple years at NYU doing my engineering degree. Being back in my old room was nostalgic, but I sure missed the perks of independence, which Sam was doing her best to remind me of.

Holly's room was through a shared bathroom, which I could have easily walked through to talk to her, but I was feeling lazy and didn't appreciate my conversation with Sam being interrupted, so I texted back abruptly.

"Can't it wait until morning?" I tapped.

"NO IT CAN'T" came the reply.

I didn't feel like responding. She was always asking me for favors, to do little tasks and errands that she thought only her big step-brother could do, but she was old enough now to do stuff herself, I figured. Ever since Dad moved in with her mom, she had treated me like her provider and protector, with a side-order of personal servant. To be fair, I loved her for it anyway.

A minute later she texted again.

"Please? I need you to go downstairs," read the next text.

"What for?" I wrote, rolling my eyes to myself.

"I need you to get me the tongs from the kitchen."

Huh? I thought.

"Huh?" I wrote.

"PLEASE, just do it, and be quiet! You're the best, Chris, will you please just do me this one favor?" she replied.

A classic line, that one.

"OK but WTF? Why do you need the kitchen tongs?" I wrote back.

Another minute passed.

"Look, please, will you just sneak down and get them? I'll explain in the morning," she pleaded.

With a sigh, I rose out of my bed, standing in my boxers with a stretch, and tiptoed out into the corridor, trying not to wake our parents. Although, they'd had a lot of eggnog so I figured it would take something catastrophic to wake them. I went downstairs, rummaged around in some drawers, and went back upstairs holding what I thought she was looking for.

I knocked gently at her door, and went inside.

We shared a converted loft space, so the only light in the room was the moonlight streaming through the skylight. Holly was curled up on her side under her blanket, with just her face showing.

"Thank you so much Chris!" she whispered. "Just put them on the desk please."

I wondered if she cared that I was standing there in my underwear, or whether she could even see me clearly. I placed the tongs down as instructed.

"No! Chris, no, not those!" she said suddenly, when she saw them up close. "The ones with the smooth ends!"

I thought for a moment then realized what she was talking about.

"Uh, these are the only ones we have. I tossed the others a couple weeks ago. Remember, the handle was broken?" I explained.

I could see clearly enough in the moonlight that she looked crestfallen.

"But those ones have sharp skewers on the tips!" she said, becoming more agitated.

"They sure do!" I commented. "So?"

Holly broke down crying.

I immediately moved to her and sat on the side of her bed.

"Hey, Hol, what's up? What's going on here?" I said, trying to provide some comfort. She was sniffling and trying to keep quiet. I put my arm on her shoulder, and she initially recoiled, but then relaxed and accepted it.

"I can't... I... it's just..." she stammered, trying to compose herself.

"Holly it's alright, whatever it is, we can talk about it. You want me to get your mom? I mean, mom?" I offered.

"NO!" she said instantly.

"No, you mustn't... no..." she said enigmatically.

I was becoming more and more confused by the second. Had something happened to her? Had someone done something to her? What were these damn tongs for?

"Holly, it's OK. If you don't want to talk, that's OK. I can sit here with you for a while, or I can leave if you'd prefer. But I think I should stay, Hol. This isn't like you," I said, worried about her.

I sat for some time, my arm still on her shoulder. She hadn't moved position. She was still on her side, still hugging the blanket tightly and exposing only her face. Gradually she relaxed and stopped sniffling.

"Chris, I... oh, Chris, I don't know if I can..." she started.

"Hol, you can. I'm worried about you. I want to help." I said.

She stared at me intently, considering her next move.

"If I tell you, you have to promise you won't judge me," she said seriously.

"I swear it Hol," I said, truthfully.

"And you've got to swear you'll never tell another soul," she continued.

"Hol, I want to promise that, but if you're in trouble or hurt or something I might need others to help me help you," I said, cautiously.

"Swear it, Chris!" she insisted.

I thought for a moment. This sounded serious. If I didn't agree, she seemed likely to shut me out completely.

"OK, Holly. I swear it. Whatever this is, it will just be between me and you," I promised.

She stared at me. I was sure she was considering whether to trust me.

Finally, she opened up.

"I've lost something, Chris," she began.

"OK, go on?" I prompted.

"I've lost a... a toy," she said, with expectant arched eyebrows, as if I was supposed to know what she meant.

"Uh, a toy?" I said.

Her face morphed into exasperation.

"Yes, a toy! God dammit Chris, a sex toy!" she blurted out.

Holy shit, I thought.

Not in a million years did I ever think my little step-sis would acknowledge to me the existence of sex toys, let alone that she owned one, let alone that she needed my help finding one. Don't get me wrong, she had a stunning body and flowing blonde cheerleader hair - any red-blooded man could acknowledge that. Even though she was my step-sister, there was no denying reality. But she had always been my little step-sis, and despite her now fully-grown adult body, I had never for a moment thought that she could be a sexual being. My mind had always just put a polite "no entry" sign up in front of that thought process.

"Um, wow... huh. OK," I said, trying to stay neutral and non-judgemental. "So you want some help finding it?"

Holly stared at me again.

"In a manner of speaking..." she said, choosing her words carefully.

The awkward silence continued.

"Oh Chris," she said, breaking down somewhat, "I've done a

stupid

fucking thing."

"Hey, you wouldn't be the first. Don't sweat it. Just tell me what's going on Hol, I'm getting more and more confused," I said, honestly.

"I was... playing... with it..." she said, trailing off.

This too was a blindsiding new thought for me. My little sister Holly playing with a sex toy. When had she grown this far up?

"OK," I said, again trying my best to stay nonchalant.

"I was playing with it, and it got... stuck," she finally explained.

The pieces of the puzzle were starting to come together in my head as my brain rapidly went through all the possible types of sex toys and all the possible ways they could get stuck.

"I think I understand," I said slowly, still only half-way there. "And it's still in there?"

"Yes!" she said, like I was a complete idiot.

"So you need to pull it out?" I continued.

"God damn it, yes!" she hissed.

I continued thinking about my little step sister's intimate anatomy and the mechanics of how something could get stuck up there. My cock began to stir under its single layer of thin clothing. I felt ashamed at my own reaction.

"Uh, OK. So I think I get what the tongs were for. And I think I get why you wanted the smooth-ended ones," I said, my words catching up to my thoughts.

"Exactly!" she exclaimed, seemingly happy that I had validated her reasoning, or perhaps it was just that she had finally broached the subject and I hadn't freaked out about it.

"I mean, if it's stuck, can't you just... you know... grab it and pull?" I asked.

"Don't you think I've tried that?! I can't! It's gone inside!" she said.

"Huh. Wow. I didn't know that was possible," I replied. "But still... surely it can't have gone that far into your pussy?"

She stared at me with a stony face.

Finally, she rolled her eyes and sighed.

"Fuck it," she said. "No use trying to hide it. It's not in my pussy," she admitted.

What the fuck? My little step-sis had a sex toy stuck up her ass? My cock continued to grow.

"Jesus..." I let out, accidentally. "Sorry, I mean... wow. OK, OK, I get it now."

"You get it? Finally?" she said, a little unfairly. It's not like she'd been up-front with me.

"Yeah... so. Well, fuck. I mean, we've got to get you to the ER right? I've heard about this kind of thing. People "slipping in the shower" and all that... not an uncommon thing. They've seen it all before," I said.

"No fucking way. Sandra works at the hospital. There is NO fucking way I'm going to that emergency room. She'll tell mom! I know it!" whimpered Holly.

Sandra was our next-door neighbor - a trauma doctor, and mom's best friend. Holly was almost certainly right about Sandra's ability to keep her mouth shut.

"Maybe she's not working tonight?" I offered.

"It doesn't matter, even if she's not there, she'll find out, I know she will!" Holly said, her panic growing at the thought she might have to reveal her predicament to strangers.

I decided not to pursue that suggestion.

"What about if... we tell mom ourselves?" I said, unconvincingly.

"Are you out of your goddamn mind, Chris?" she exploded. " 'Hey mom, sorry to wake you up, I sat on a dildo and it got stuck up my ass, and I need you to drive me to the hospital!'"

So it was a dildo was it? The thought of her sitting her ass down on a dildo down to the hilt and it popping inside fuelled the growth in my underwear. I shifted my position to try to hide it.

My mind was reeling at the language she was using. What happened to the sweet little girl whose biggest craving - or so I thought - had been for pink tiaras?

"Yeah, OK, I guess that is not what you want to say. I was just thinking if you were the one to raise it with her first, it would be like you were doing it on your own terms, rather than being found out?"

"I am

not

getting found out Chris, you hear me! This does

not

leave these four walls! You promised!" she said, with a mixture of pleading and threatening.

I sat and thought a while.

"So, uh... I don't have another plan, Holly. You want me to go buy a new pair of tongs? The smooth ones? I could do it in the morning, as soon as the stores open," I offered.

"The morning?!" she replied desperately. "Chris, I can't keep this thing up there all night! Isn't there some place open that you could try?"

"At half past one in the morning on a Sunday? At this time of year? Shit, I don't even know if they'll have cleared the snow off the roads," I said.

She had no reply, and resumed a thoughtful, despondent expression. All I could think about was her lying there with a dildo up her ass. Her dejected attitude put a damper on my cock, but not enough to get it back down.

"Chris," she said quietly.

"Holly?" I asked.

"You need to help me," she said.

"I know Hol, I'm thinking, I'm doing my best to think of something," I responded.

"No, Chris. You need to help me. You need to help me... get it out," she said.

I looked into her eyes and my damned disobedient cock was immediately back in action, tenting up a shameful bulge right in front of her.

"Wow Hol, that's... I mean..." I said, lost for words. "Don't you think that will be a little... strange?"

"No shit!" she exclaimed. "But I'm out of options! Chris, if you help me, I will be forever in your debt, but you ever mention or breathe a word of this to anyone after tonight, including to me, you're a dead man."

"Fuck, Hol, I can't believe you're asking me to..." I wobbled.

"I am. I need you to do this for me, Chris. But remember: one word? Dead man." she said, resolutely.

I steeled myself, wondering what exactly I was going to be able to do.

"So, uh, can I take a look then? See what we're dealing with?" I said, reaching for the bedside lamp.

"No light! You don't need to see! Just... feel," she said.

The lack of electric light felt like a polite fiction - a piece of plausible deniability that we could both call upon later - but in reality, the moonlight was more than enough for me to get a very good look at her. Perhaps she wanted to pretend she couldn't see me, sitting there in my bulging pants.

"OK, OK... you're at least going to have to get out from under that blanket," I said.

Slowly, the blanket uncurled from her grip, and she wriggled it down. As she exposed her neck and shoulders, she suddenly stopped.

"I'm... not wearing anything, Chris," she said, as if to excuse what I was about to see.

"It's OK, I'm barely wearing anything either," I replied, in a possibly ill-judged attempt to lighten the mood. I saw her eyes flick towards my crotch and back up. There was no way she couldn't spot what was happening down there.

Gradually, she resumed shuffling out of the blanket. She tried to cover her breasts with her arms, but largely failed to contain them. It was all I could do to avoid letting out an audible

damn

.

With one final motion she kicked off the blanket and I looked down on her fully naked body, curled in a foetal position towards me, her arms trying to cover herself, and her legs pressed together to prevent me seeing anything.

"Go on," she said.

In truth I wasn't sure how to start.

"Uh, you want to lie on your front, I guess?" I suggested.

She seemed to agree with that, as it would hide her front from me. She rolled over and put her face in a pillow.

I took this opportunity to readjust my cock in my pants, to make it more comfortable - at the cost of making it a lot more visible, should she turn to look.

"I'm going to... uh, touch you now, Hol. Is that OK?" I asked, trying to be respectful.

"Do it," she said, muffled by the pillow.

I moved fully onto the bed, climbing over her, and putting one leg either side of hers, sitting up and looking down at her incredible ass. It was muscular and round, and her cheeks were pressed tightly together. I couldn't get a good look at her asshole.

"Hol, I'm going to have to..." I said, not knowing how to describe my upcoming manoeuvre.

"Less talk," she said, curtly.

I pressed my thumbs into her cheeks and spread them apart to reveal her very well lubed up slippery little sphincter. My cock was at absolute full mast by this point, directed up at the ceiling in an obscenely dominating pose. I couldn't believe I was this hard while holding open my step sister's ass cheeks and staring into her tiny little puckered hole.

I did the only thing I knew how to do in this situation. I began to play with her butthole. Circling one finger around it, I rubbed her gently to try to relax her. This is what I would have been doing to Sam, had she been sleeping over. Sam enjoyed anal a lot, particularly the slow build-up, foreplay and fingering. I tried to imagine it was Sam in front of me. I plunged a finger inside.

Holly startled.

"It's OK, Hol, I'm just trying to be as gentle as I can," I said.

"It's fine, keep going... I just want... it out," she said.

I began to saw my forefinger back and forth into her hole, in a gradual fucking motion. Her asshole opened up willingly around my finger, and I could have sworn I felt her rock back against it.

I brought a second finger into play and massaged her rosebud before sliding the two of them inside together. I was still just warming her up. Suddenly when my first and middle finger were pressing into her ass at full depth, I felt it.

"Hol, it's there, I can feel it!" I said, excitedly.

"Thank fuck. I was worried it had gone too deep already," she replied, her body visibly relaxing. I felt her muscle relax around my fingers too.

I pushed harder and a little further inside her ass. Although I could just about get my fingers to the soft silicone edge of the toy, I had no purchase.

"Hol, it's there, it's so close, it's just... I can't grip it," I said.

"Put your thumb in," she commanded.

My little step-sis, folks. Asking me to put my thumb up her ass. I could barely resist the urge to start touching my burning cock with my other hand.

"Well, at least you're well lubed up," I said, immediately regretting it.

To my surprise, she didn't tell me to shut my mouth.

"At least I did something right, huh?" she grunted, as I began to press the cluster of thumb, forefinger and middle finger into her ass, stretching her out even further.

I pushed hard, and she grunted deeply again.

"Oh, fuck," she said, in a tone I couldn't quite read.

"I'm sorry. Is it hurting?" I asked.

"No," she replied. Hot

damn

.

Onwards I pushed, getting three fingers in up to the first knuckle, but it felt impossible to go further.

Holly wriggled her ass back towards me, willing me on.

"Keep going," she insisted.

I paused to consider.

"You know, I think this isn't the best position," I said. "Your ass cheeks are kinda pressed closed. Can you get up on all fours?"

She raised her head.

"But then you'd..." she began.

Then I'd what? See her pussy? I thought.

"Can't you just keep trying like this?" she asked.

"Yeah, but I think it's going to start hurting if we can't get you spread open a little more," I said.

With a resigned sigh, she slowly shuffled her legs forward and raised her ass, getting into a doggy style position in front of me. She turned and looked at me, and I was suddenly aware that my very hard cock was poking forward right towards her most intimate area. I wasn't sure how much she could see over her shoulder, but her gaze lingered for a moment.

I moved my legs inside her legs and pushed them apart, spreading her ass open in front of me, and revealing her very wet pussy. I couldn't tell if it was wet from lube... or just her natural reaction.

"Quit staring and get on with it," she said, turning back and putting her face back down in the pillow.

Interesting - she had acknowledged that there was more than enough moonlight for me to see by. I wondered what she had seen.

I resumed my probing of her anus, stealing looks at her pussy on the side. From this angle it seemed to be smooth-shaven, with maybe a short runway of hair on her mons, just barely in view. Her inner lips were splayed out and completely slick, and a little puffed out with engorgement. Her clit shone with wetness, peeping out like a glistening pea from a tight pod. She must have been deep into a masturbation session with this toy. I started to understand how she might have lost control and shoved the dildo up her ass with reckless abandon.

I dutifully pushed my fingers further into her ass, getting a good way inside, rocking them back and forth, trying to stretch her wider and wider. There was absolutely no denying it now - she was rocking back against my fingers, in time to my thrusts.

"Well?" she said, looking up, with flushed cheeks. "Any... ugh... progress?"

"You're loosening up. That's progress. I need to make sure I can get a real good grip on this thing. I don't want to push it in any deeper," I explained. "Try to relax. You're doing great."

"Bit hard to... ugggghhh... relax, with my... hnggg... brother's hand up my ass," she panted out, becoming audibly hot under the collar.

"Forget whose hand it is. Just try to... enjoy it, I guess," I said, floating the possibility that this wasn't a clinical rescue mission but something that she might actually get some pleasure from.

"Yeah..." she said, not denying it. She began humping back at me, and a gossamer thread of clear liquid drooled from her pussy down onto her bed, staying connected at both ends, and swaying back and forth in time to my finger-fucking. I desperately wanted to pull my cock out. My animal hind-brain was taking over. She was only my step-sister, right? No blood relation, right?