I had three friends over to celebrate – or mourn – the end of the Christmas break. John, a mild mannered friend from childhood; Sam, whom I’d known for a few years and a pretty decent guy; and Mike. Mike was closer to the other two than he was to me and a bit arrogant, but he meant well and we got along so it was never a big problem. All four of us were 18 years old and right now we were gathered around the living room TV, playing a game my sister had bought me for an all night session.

So where was my sister in all this?

She was turning 20 next week and right now was off on a pre-birthday bash. She said she was off with her friends, but I knew her party actually consisted of three girls (including her) and two of their boyfriends.

In other words, chances were high she and her beau would be taking a detour on the way home.

It was just when John cheered and exchanged high fives with Sam for a point well scored when the door bell rang. Being the host, I went to open it and was surprised to see my sister stumble in.

“Woah, you okay Jess?”

She looked down at me, tossing wild strands of her dirty blonde hair behind her head. I’ve heard people say guys usually have a height advantage but I guess she’d had an extra growth spurt since she was an inch or two taller.

“Yeah…”

She leaned and threw out an arm for support against the wall. I took the chance to glance over her body. She was wearing short shorts and a tank top, pretty standard fare for a party. It was now that I noticed she’d splashed something over her top making her collarbones show through and at that point I looked away; I didn’t want to see anything else.

“Bit too much to drink?” I asked, recognizing the smell of the liquid over her top.

“Yeah…” John cheered again and she looked into the house. “Your crew’s still here?”

“Well, yeah. All nighter, remember?”

“Oh yeah. I’ll just go say hi then.”

I followed her down the corridor and overtook her in time to enter the room as she leaned against the doorway. “Hi, guys!” she called.

Mike and John turned at once. Sam paused the game while I leaned against the sofa positioned by the door.

“Hey, Jess.” John waved.

“Heya,” Mike held finger pistols up to her for some reason.

“Thanks for the game!” Sam waved with the controller and my sister smiled.

“Glad you enjoyed it guys. Anyone beat my record yet?” we all shook our heads and she laughed before rubbing her forehead. “Well, you have a few hours left ‘til Mom comes home so good luck.” She beckoned me to join her outside the doorway.

“Yeah?”

“Matt, I really need to go sleep this off. What time is it?”

I leaned into the living room to check the clock and my eyes went wide. “Quarter to two?! Shit, I thought it was 11.”

Jessica sighed and rubbed her forehead again. “That would have been nice. I had way too much fun at that party. I got a lift home right after Sarah called me out on it.”

“Huh.” Sarah was the resident drunk in Jessica’s friend circle, so if she’d said Jess’d gone too far, Jess had definitely gone too far. “You’re not gonna throw up are you?”

“Course not! Just, cover for me if Mom says something in th’ morning, yeah?”

“Sure.” Mom would calm down as soon as Jess said she didn’t spend time with Simon anyway.

“And…” Jess sat at the foot of the steps to take her heels off. “You guys have fun, but don’t get too loud.” She tossed her heels to the line of shoes by the door and bounced off the stairs to the living room again. “Night guys!”

“Goodnight!” They called as one.

Sam was speaking over his shoulder from the screen, but now that I was standing behind Jess I could look straight at Mike and John and saw what she was too drowsy to. It made me grit my teeth.

Mike’s eyes had gone from her face to her bare feet and was now fixated somewhere beneath her waist, while John was pretty blatantly staring at her tits. I remembered the beer on her top and hoped he wasn’t seeing too much. I didn’t even know who to be madder at: Mike, for being the perv he always was in my house or John, who’d known us for so long Jess was practically his sister too?

All of these thoughts had come to me in a second and by the time they registered Jess had turned to the stairs with a “Goodnight, Matt,” behind her shoulder. I watched her climb the stairs and noticed that her shorts ended about an inch beneath her ass, so Mike would have gotten quite an eyeful of her bare legs.

I shook my head to clear that image (which was tricky since she was climbing up and thus bringing her ass closer to my line of sight) and marched into the room. I sat on the arm of the chair until I heard her enter hers and closed the door.

“Guys! Can you not make eyes at my sister of all people?”

Mike snickered. “Are you kidding me, man? I wish I had a sister like her.”

“I do too, and then you might know how awkward it is!” I stood over the trio on the floor with my arms folded.

“Matt, go easy on the guy.” John spoke while concentrating on the screen, “can’t blame him for your sis looking like that.”

“Or dressing like that.”

“Wish she hadn’t been wearing a bra.”

The two grinned at each other and I groaned.

“She looked pretty messed up,” said Sam, still watching the TV. I fixated on the normalcy of his question.

“Yeah, she got wasted apparently.”

“No shit, Sherlock.” That was Mike, of course.

“A-anyway,” I looked back at Sam’s dark brown hair, “she just needs to sleep it off. She’ll be fine.”

“You sure? She doesn’t throw up or anything? My cousin does that a lot.”

I shrugged. “Well, I’ve never seen her throw up. Then again, apparently one of her friends told her she’d overdone it so she probably did it there. She does go out like a light though.”

“Really?”

“Yeah,” interrupted Josh. “You could sound a horn by her head and she wouldn’t even notice.” He grinned at me and I grinned back. He was referencing her second hangover. I had gone to grab a pair of scissors from her room, only to have the alarm he’d set on my phone as a prank go off at max volume in her doorway. I could have sworn I’d stopped breathing for a second before realizing that she had, as he said, not noticed a thing.

Mike chuckled. “Really? So we don’t need to be quiet or be on our best behavior then?”

“Nah, but hey; she’s cool even when she’s awake. But Mom will be home at, like, 7 or 8 so we need to at least pretend we’ve gone to sleep by then, k?” I would have sat on that info a while longer but after realizing my mental clock was at least three hours slower than I thought it was I decided against it.

—

Sam stopped playing a few minutes after that and 5 minutes into Mike’s session he tapped me on the shoulder. “Hey, I need to go to the toilet.”

“Uh…sure? Why are you asking me that?”

“The downstairs one reeks, so I wanted to check if I could go upstairs.”

I raised an eyebrow. There was nothing wrong with the downstairs toilet in my opinion, but Sam was fussy over a lot of things so I shrugged. “Go for it.”

“Thanks, man.” He clapped me on the shoulder, told the others where he was headed and left.

—

“What the hell is taking him so long?” I was sitting on the arm of the sofa, tapping my foot as I glared at the roof. It had been another 3 minutes and now it was John’s turn at the controls. Mike pivoted on his butt to face me.

“Maybe he got lost?”

I rolled my eyes, but froze as a thought came to me. “Oh yeah, he was complaining about his stomach last week wasn’t he? Is that still bothering him?”

Mike smirked. “Yeah, that’s gotta be it. You hear anything about that John?”

John shrugged. “Maybe one of you should go check.”

“I’ll do it,” said Mike at once. He clapped me on the shoulder too. “Who knows, John may screw his game up sooner than later.”

“Hey, fuck you” laughed my best friend as Mike also left.

—

Mike turned out oddly prophetic as John lost within 5 minutes after a fumble even I could have avoided and I was horrible at the game. He held the controller out to me, now sitting on the sofa proper. “It’s your turn, Matt.”

“Yeah, thanks.” But I waved it away. “What on earth is going on up there?”

“Maybe they’re playing Cave Story?”

I frowned. Sam had caught me playing it in class before the Christmas break (yes, I’m an old-school gamer, sue me) and I had promised he could have a go on it today, but “Bit of a dick move for Sam to start playing it himself. That’s something Mike’d do.”

“Eh. I think I can understand where he’s coming from.” He placed the controller in my hand. “How ‘bout I go upstairs and take a look?”

“Yeah, thanks man.”

“Hey, I won’t let them keep anything from my friend.”

He clapped my shoulder on his way out too.

—

I’m sure everyone reading this is smarter than I was at the time so it should come as no surprise that John didn’t come down either. I lost my game session in five minutes as expected and stared at the ceiling and a few seconds of thought later I had turned the console off and climbed the stairs – quietly for Jess’ sake – to see how absorbed the three of them could really be in fucking Cave Story.

The first room on the left after climbing the stairs was the bathroom and it didn’t surprise me that it was empty, so I turned right. As I got closer to my room I began to hear muffled voices and chuckles. I suppose logic was overriding my senses at this point since it wasn’t until I peered into my lit bedroom that I realised the sounds weren’t coming from there. I turned the light off and looked ahead.

The only room in front of me, at the end of the floor, was my sister’s and its door was closed shut.

I tiptoed towards it. Yeah, that was definitely Mike and Sam, though I couldn’t make out what they were saying. I assumed they were looking through Jess’ phone and I could only hope she hadn’t been sexting anyone.

As you may have guessed, when I opened the door I saw something far worse.

My sister’s quilt had been thrown to her feet, most of it spilling onto the floor. With a shock I noticed the vivid blue of her shorts beside it and, further along, her panties. I looked up and gasped.

I saw those long legs of hers that had transfixed Mike so badly, bent towards my left at different angles as though she were taking a step. My eyes followed them up and saw the flesh exposed by the loss of shorts all the way up to her waist. I saw the curve of her left thigh into her ass though my view of her core was obstructed by the hand floating above it.

Mike?

He hadn’t even noticed me, still leaned over my sister’s pussy, his body blocking my view of hers, though I could see Sam’s body further along. A single syllable escaped my lips. Mike and Sam didn’t notice, but:

“Matt?”

A third figure stood up from behind Sam. It was John, my best friend. Mike and Sam noticed me at last. I stared at all of them for a second before they beamed.

“Hey, you’re here!” Mike beckoned me with the hand that had been stroking my sister’s vagina. He waved the other at John and Sam. “Hey, step back guys! Let him see what we’ve been up to so far!”

They stepped back, and so did he. I looked at the bed between them and my jaw somehow dropped even lower.

I already spoke about her long legs. I could now see both of them and the opening between them. She must have shaved recently, since the skin around it was bare. My eyes trailed to her waistline as it dawned on me that they’d taken her top off too. I saw the V of her stomach centring at that slit and the navel above it. My eyes went up, almost in slow motion, to the bottom of her rib cage. Further up still and…

As her brother, I’d seen Jess wear looser clothes and knew that tank top was holding her back, but I had no idea her breasts were this big. I could easily fit one in each hand and it made me furious that these three had seen her before me.

What?

I shook my head again and tore my eyes away from the light brown nipples perfecting those mounds. There was the collarbone I had spied earlier and, facing right, Jess’ face.

Someone had been working on her head because that dirty blonde hair was strewn behind her, yet she remained unconscious and at the mercy of my friends, eyes closed shut.

“What…the…fuck?”

I looked at Mike, who was grinning at me, then at Sam and John who also thought this was the greatest moment of their lives. Behind John, in the corner of the room, I saw where someone had thrown her top and bra.

“Come on, you can’t honestly tell me this doesn’t turn you a little on?” Mike reached his hand out again. “We’ve been waiting for you, come on.”

“You can’t be serious. What the hell are you guys doing?”

“Isn’t it obvious?”

“You’re raping my sister! What do you mean, you were waiting for me?”

“Oh, come on!” Sam held his arms out, “Our pants are still on idiot; of course we haven’t raped her.”

They were on, but I continued. “You’ve been here for 20 minutes and I’m supposed to believe you didn’t do anything to her?”

He had the nerve to look embarrassed. “To tell the truth, I was actually too scared to take her clothes off.”

“You were having lots of fun groping her though!” Mike interrupted and the three of them laughed.

“So did you when you came up! Anyway, safely stripping a sleeping girl without waking her is a two man job.”

“Three man job if you want to get anywhere,” John shrugged and looked at me. “Can you believe by the time I’d gotten up they’d only taken her shirt off? If I hadn’t promised them she’d sleep through anything they’d probably still be working on her bra!”

I ground my teeth. “What the fuck, John. Why the hell are you going along with this? You’ve known her way longer than these two!”

“So what? You have any idea how long I’ve wanted her to be my friend with benefits?” He stepped forward and stroked her hair, trailing a handful down the side of her face and traced a pattern on her shoulder.

“Don’t touch her!” I took a step forward. “I can’t believe this! For Christ’s sake, we were just playing a game she bought us!”

I cringed as soon as I said it. My former friends glanced at each other before bursting into laughter, covering their mouths. I hoped Jess would wake from this but John was right – she would sleep through anything.

“With an excuse that horrible I think it’s obvious you want her as much as we do.” Mike stepped towards Jess and placed his palm on her navel. “So come on; her pussy’s right there for you. Haven’t put anything in her yet.”

He proceeded to scratch her stomach as the other two chuckled. Sam got on his knees and began to suck on Jess’ left tit while John, gripping her right, walked around the bed to do the same there. Fighting my hormones I took another step forward but Mike stuck his right palm in my chest.

“Come on man, the three of us are gonna have her whatever happens. Now you can either join in or you can go down and miss out on all the fun. If you try and stop us, well.” He looked me up and down. “We could easily take turns holding you down while the other two fuck her. Can’t we?” He looked down at the two sucking on my sister’s nipples and they mumbled their assent. Sam looked up while biting hard and smirked. “Besides,” Mike looked down again at my crotch, “from how hard you are it’s as though you aren’t wearing anything under those shorts.”

I jumped back with my hands covering my dick and he laughed. My face turned red but I had to admit my dick felt harder than it ever had before. He motioned back to Jess’ pussy as his left hand began snaking a path to her pussy. I put my hand over it, meaning my thumb passed the line of her waist.

“Stop!”

“And?”

I didn’t want to give in, but I also hated the idea of being held down or missing out on anything so before my brain could kick in my dick answered for me. “I’m in.”

He grinned. “Nice!” He slid his hand out from beneath mine and stepped back. Horrified by myself I looked down at Jessica’s smooth skin. Mike’s finger must have dug into it when I stopped him because there was a small pink patch beneath my hand. I placed three fingers over it. I was aware of the other two stopping their assault on her breasts to look at me and felt even worse as my fingers moved up to her navel. I swallowed and moved my hand down.

I passed the pink mark and felt a series of slight pricks. Surprised, I moved my fingers back up and peered closer. It seemed she had shaved, but the tiniest hints of pubic hairs were growing back. I continued my descent down, letting them tickle my hand, and stopped right above her opening.

I’m being forced to do this. That’s why I’m doing it. I glanced up at the three and their greedy faces and back down in an instant before sliding my fingers down…down…

I could feel the small mounds on either side of her core pushing against my middle finger as I ghosted my hand down. We were all virgins of course and with how new this felt I begun to understand why Mike had taken so long to start fingering her.

But they got to see her naked and touch her tits before I did, so it was about time I claimed something too, right? I turned my hand upside down and ran my three fingers up and down the gap between her legs, my middle finger passing up and down her slit. I smiled, trying to hide my nervousness and then looked at them with my finger poised beneath a bump I felt under the surface of her lips.

Their mouths were hanging open. A part of me, possibly the part disgusted by them, told me my biggest challenge would be to look at my sister as I defiled her and so I looked down at her face, noting that Sam was still lightly squeezing her left breast.

Jessica was as oblivious as ever. She looked as though she was sleeping and as clichéd as it sounds, her hair really did look like a brown and yellow halo with how it cascaded around her head and shoulders. Whatever held me back snapped as I gazed into her eyelids and slowly pushed my middle finger in.

Holy fuck was she tight!

Maybe I had always wanted to fuck my sister as John had but now all I could do was revel in how good it felt to have her pussy suck my finger in past the nail, the first knuckle, the second knuckle, to the base. When I pulled out, all I could feel was the resistance she put up, as though she needed me inside her. And all I could think was “If she’s this tight on my finger, how tight is she gonna be when I’m raping her?”

A small part of my brain screamed at that but my dick overpowered it. I licked my lips as I drew my finger back out to the tip and admired the faint glisten on its underside. I placed my left hand at her waist and slid it over that flawless skin at her side before it came to a rest on her right breast. I was right; it did fit snugly in my hand with flesh to spare. I grinned as I spread my fingers over it, letting the hard nipple poke my palm. I brought my thumb down to rub circles around her rubbery areola before tilting her nipple up, down, left, right like a joystick. My eyes skimmed over her left breast still worked on by Sam before coming down to my finger still positioned at her entrance. I slid it back in, scraping the underside of her opening with my finger.

Did her pussy just tremble?

It felt like it. I cocked my head to the side and continued trailing my finger up to the base. Then I scratched my way back down.

I think it did!

I licked my lips again. I couldn’t wait to see if I could replicate that feat with my dick. As if he had read my mind, Mike clapped me on the shoulder again.

“So, you wanna fuck her first? You’re her brother, after all.”

John and Sam snorted, but I stayed smiling. “Of course. And as her brother I want everyone to back off.”

The three guys raised their eyebrows but did as I told them.

“Wait, you should totally cum in her man!” This was Sam and I looked at him.

“What?”

“Cum in her!”

“What? I don’t know if she’s on protection!”

“Dude, don’t pass this up!” John held his arms out. “You’re the only one who can cum in her!”

“Yeah!” this was Mike, “Think about it! If she gets pregnant from this, she’s obviously gonna go after her boyfriend, right? And even if she does remember collapsing here, who the fuck would DNA test the brother?!”

That made sense. I didn’t fancy getting her pregnant, but at the moment all I cared about was getting more of Jess than the three before me and if that included me being the only one allowed to put my spunk in her, that was great.

I got on the bed and straddled poor Jess.

Of course, I wasn’t gonna put my dick in her right away; I was gonna savor the moment. I put both hands on her hips and pressed deep into her sides as I dragged them up to her tits. I noticed the leftover saliva on them now and rubbed it off as I explored those vast mounds before bending down and taking her left nipple into my mouth.

I wasn’t going to have anyone else’s spit on my big sister. Or anywhere else. I looked up.

“Hey, any of you make out with her?”

They all chuckled and shook their heads. I bent down and pushed that breast to the right so I could admire it from the side. I had been expecting a deep bite mark from Sam on her nipple, but could only make out a faint line. I shrugged and ran my tongue from the bottom right of her breast to the top left before fixing my lips over her nipple again. I squeezed her right between my left thumb and forefinger and twisted it gently. Then I twisted it in the other direction as I heard them chuckle.

I switched sides, sucking her right nipple and twisting her left. I repositioned myself so my left hand could snake its way down from her breasts, over her navel and tiny pubes to her entrance and pushed my middle finger in hard. I pulled out and forced it in again. The third time I used two fingers and I could have sworn her crotch shook. I was going primal now. I needed to be in her.

I brought my head up and began biting her neck as I lay atop her body. One hand keeping me up, the other unzipped my pants and fished in the gap, pulling out my rock hard member. I wanted to be naked and press my body against hers, but I couldn’t do that with an audience. I rubbed my head up and down her entrance twice before pulling my body back and positioning before it.

My audience squealed with impatience as I finally began the act of penetration.

Fuck, she really was tight!

I bit my lip at the pressure her entrance put on my head and placed a hand on her ass to keep the two in line. I groaned quietly as my bulb was slowly, slowly swallowed up and couldn’t stop a moan escape at the euphoria when it was finally fully inside her.

“How is it?”

Ignoring John, I began edging deeper and deeper inside her, trying to angle my dick at the top of her love canal. I kept both hands at her waist now, not even caring about the audience as I watched my penis slowly disappear inside that pussy, connected to that perfect slender body with those perfect tits and innocent face with those full pink lips.

I pushed further. I felt a spike in resistance and fell on top of her. I gripped her shoulders from her back and used her body as leverage to defile her. Even through my shirt I could feel her pert nipples poking into my chest and buried my face in her neck as my pelvis finally met hers.

I laughed into her ear then I raised my head and bit my lip.

“Feel good?”

“Fuck yeah.”

“But weren’t you just playing the game she bought you?”

Mike and Sam started laughing but I looked John straight in the eye. “Yeah, but I suck at it, remember? She probably just bought it for herself.” I placed my right hand on her breast as he asked another question.

“Probably?”

I just grinned. “Do I look like I care?”

The trio laughed again as I tugged the mound in my hand gently in every direction. My sister was such a lovely creature and right now she was mine. It was her body beneath mine, her breast in my hand and my dick sheathed in her pussy. If there was one problem, it was that she was already soaking wet.

Of course, it was to be expected after 20 minutes of foreplay, but the thought that those three had gotten her wet and not me made me furious. I began to slide out of her, the skin of my dick rubbing against her innards as I pulled back. Eventually her opening stopped my head from leaving completely.

It was as if she didn’t want me out of her.

Needless to say, this thought made me primal again. I gave a toothy grin as I pushed inside her and this time her whole body shook. Too bad those idiots couldn’t notice. I pulled out for a third slam. I was speeding up, though she was still throwing up beautiful resistance. I pulled back to the head for a second when

“…Simon?”

Everyone froze. A part of me wanted to cover Jess’ eyes as they flickered and pound her senseless but my brain took over at last. Jess continued blinking, but her eyes would only open halfway.

“Oh…Simon…”

She smiled and pressed her feet against my ass. My brain went into overdrive and I pointed at Mike. Thank goodness he understood what I wanted in a snap and stepped forward, bringing his face close to mine.

“Yeah, babe?” Both he and Simon had deep voices and I was betting on Jess’ stupor that she wouldn’t tell the difference.

“Ffuck…me…” She pressed the side of her face into her pillow.

“Oh, you’ll get fucked alright.” Mike winked at me and backed off again. I grinned and pressed her feet further against me. So, not only was I gonna rape my sister but she was gonna help me do it? I bent over her and she wrapped her arms around my back. I pushed in slowly and felt her pressing me with her feet. I kissed her neck as I fondled her breast and she moaned in my ear.

“Oh…ff…ck…”

My left hand was back over her shoulder and I gripped it as I gave her nipple an extra squeeze. She sighed in response. I pulled back and thrust into her and felt her body shudder beneath me, her free nipple brushing my shirt. I pulled back. Thrust again. And again. With every slam a faint gasp left her lips. With my next slam I raised my head and licked them. She brought a hand to the back of my head and kissed me. I let her handle it to the best of her ability and even as she struggled to raise her tongue I pulled my dick back and pounded her, letting her moan into my mouth.

I swapped arms, now groping her right breast. I swallowed her moan as I twisted her nipple and went up for air. I dove back to those pink lips that floundered without me. She began whining and moaning louder and louder.

“Si…Si…mon!”

Her pelvis began to shudder and I laughed in her face. I tried to kiss her again but she was panting too heavily. I settled for leaving gentle bites in her neck as her moans grew higher and higher pitched until

“Aahh!”

Her juices shot out of her. I buried my head in her hair and grit my teeth, desperate not to cum as her fluids washed over my member, even slowing my thrusts. I felt her breasts heave despite flattening them with my body until her breath settled. My dick was currently halfway inside her and I tried to finish my thrust but when my base touched her opening I knew I was going to cum too.

All I could do was pull back once more and release all my sperm in one final slam as I groaned. She moaned loudly too. I rode out my orgasm and collapsed on top of her.

“No…condom? You’re…dangerous…” I looked up in time to see her lick her lips and turn her head to look at me with those glazed eyes. “Let me finish you off…”

I didn’t know what she meant until I felt her arm snaking between our bodies. I raised myself a bit and the joint between her thumb and finger stopped against my base. I took a sharp breath at the sensation and, not knowing quite what to expect, began pulling myself out of her.

We both moaned and pulling my head out felt like torture, but I managed it. My half-hard dick fell onto the back of her hand and that vacant face gave me a smile as her hand rotated.

“Come…clos…er.”

She held my dick in a loose grip and I followed it up her body on my knees. Was she gonna give me a handjob, or…

When my dick reached her face, she reached her head out and licked the tip. I shuddered and her smile widened.

“Let me…clean you off…”

She opened her mouth and of course I obliged, waddling closer a little more to let my head sit on her tongue. She closed her mouth over it and it felt like I would cum immediately. She began to suck, slowly at first. She was still out of sorts so her tongue work was sloppy, but I helped by placing my hands behind my head and thrusting into this new hole.

I didn’t need to look at my friends to know how jealous they were that I’d gotten the first fuck and the first blowjob out of our toy. That joy was only exacerbated by knowing she was currently “cleaning” up both my cum and her own juices and the moans she punctuated each of her sucks with only added to the euphoria. I felt my dick growing with each and every one.

If only I’d done this sooner! I thought to myself as she trailed saliva over my dick like the waves on a beach. She’d been hungover so many times in the past two years. It made me ashamed to think I had Sam and Mike to thank for the opportunity right now and it almost impacted my growing erection. Thankfully another moan from my clueless sis and I was back to how I should be.

I looked up at the impatient trio and smiled, noting Mike’s eyes staring at her available pussy and biting his lip. Right now Jess thought she was having sex with Simon, so it didn’t make sense for it to turn into the orgy those three wanted it to be. I turned back to Jess’ closed eyes determined to make this last as long as possible even as my dick grew to stroking the back of her mouth.

I kept pumping in slow motion and when she began to gag directed my dick sideways so that it glanced off the inside of her cheek, making it bulge with every thrust. The deformation of her face was so sexy. With one hand behind her head the other went back to her left nipple, my forefinger tilting it in different directions until she moaned louder than before. Her tongue shot up straight into my sensitive head and I hissed. The mental barrier keeping my cum back broke and I began firing into her cheek. As my dick pulsed the second load fired into the back of her throat and she choked, but I pressed down on her forehead and held her mouth closed as I resumed firing into her cheek. Though she coughed and her eyes flared open for a split second, she was able to keep it all in her mouth. I felt her swallowing around my dick but waited until she tried to move it aside herself to take it out. I placed my hands over her ears and bent over her and spoke as deep as possible.

“Did you swallow all of it?”

She nodded.

“That’s a good girl. Now get some sleep, alright?”

She nodded again, licked her lips and turned her head to the side. Her half open eyes closed.

No one moved, even me with my dick still poking into her neck, until I could be sure she’d fallen asleep. Even then I waited a few seconds longer just to spite the queue.

“She’s ready,” I grinned, tucking my dick back into my pants. They crowded around me and whispered praises. I chuckled as I got off her. Mike called dibs on her pussy and clambered atop her legs as I had. He flexed his fingers and slid his middle finger inside her facing down. I guess the orgasms that had just taken place in there had removed some of the friction – and thus fun – since he went a bit faster than I did. Meanwhile, John was tracing the line of her face and I got the impression he had wanted to be closer than just FWBs as his finger traced her lips before entering.

I decided I wanted to immortalize this so grabbed my phone from my pocket and started recording. Sam noticed and scrambled in his pockets for his to no avail. Before he could complain, I cut him off.

“I’m the brother, remember? I get recording privileges.”

“You’re gonna share with us though, aren’t ya?”

“We’ll see.”

“Come on!”

I shrugged and nodded to Mike who had just unzipped his pants and stopped.

“Hey, since we can’t cum in her, where do we put our loads? Oh! Why don’t we let the brother decide?”

The three of them laughed and shrugged again. “Why not on her? In fact, why don’t you all cum on her? We can see how much you’re really packing and we can just clean her up after we’re done.”

“Clean her up, he says! What a good brother!” Sam and John laughed at Mike’s quip and I let them have it. They agreed with the proposal and I centred the camera on Jess’ pussy as Mike violated it.

I wondered if I had another reason for recording all of this and putting the four of us in danger. Blackmail? But what was the point? If I did film my sister getting raped by these clowns, all they needed to do was point out I was the one filming and I’d get dragged down with them. As Mike sighed with his first full penetration he looked at me.

“Hey, you sure she’s not a virgin? Bitch is tight.”

“I’m sure. Simon definitely fucked her on Christmas.”

“How can you tell?”

“She came home without underwear.”

Mike and Sam laughed. John was too busy pressing his finger in and out of Jess’ mouth. “So you have been perving on her!”

“Well, we’ve all gone well past that at this point, haven’t we, so why are you laughing?” That shut them up. “I’d say they’ve fucked once or twice before that as well. She was really happy coming home once.”

“Well, hear that?” Mike looked at Sam and John. “That means she’s gonna be fucked more tonight that she has her whole life!”

I smirked and turned to Jess’ face. The way her lips caved in and out with John’s finger was hypnotic and I couldn’t help notice (again) how helpless she was. I’d already cum twice but that thought was making me hard again. That was definitely blackmail worthy, but damn was that intense material. Why the hell would I blackmail my sister and what the hell would I blackmail her for?

…well, duh.

If both my hands weren’t currently holding a phone steady, I’m sure one of them would have slammed into my face. I pictured myself holding her naked body down on the bed as I raped her over and over, laughing at her face of horror. I was looking forward to that.

I watched as John unzipped his pants on camera and pulled out his dick. I stepped closer to the action as he fed it to her. I watched on the screen as his member disappeared inside her mouth only for it to emerge beneath her cheek a second later, taking pride in knowing that I was the only one Jess had helped do that. Here John would be doing all the work.

And speaking of keeping the best of Jess to myself…

“You know you shouldn’t cum in her mouth, right?”

“Huh?”

“You’ll wake her up!”

“Oh yeah,” he smirked at her peaceful face deformed at the mouth “think she’ll appreciate a new face cream?”

I actually found that pretty funny. “That would probably wake her up too. Why don’t you cum on her stomach? Or her tits.”

“Hey!” Sam, who was evidently a fan of Jess’ breasts if his current actions were any indication, looked up and scowled at me and I shrugged.

“Aren’t you a good brother, Matt? I never knew you were so sentimental,” John spoke with his eyes fixed on the face devouring his cock. Mike let out a loud moan and I turned to him.

“Hey, don’t go too deep or you’ll wake her up too. I don’t think she’ll buy the Simon shtick twice in one night.”

“Spoilsport. But look at you, wanting to make sure your big sis stays clean and gets her beauty sleep.”

The three guys laughed but I let them have this one too. After all, not only was I forcing them to cut corners in their little gang rape, they would only get to fuck her this one time.

But me?

I’d be fucking her forever.

---