High School Harem Pt. 07

"Ok" I responded.

Don't worry, it was not lost on me how weird it was to be receiving instruction on the proper etiquette for having anal sex with my sister, from my sister. I tried not to think about that too much. So I just heeded my sister's sage advice and began rubbing my cock along her pussy lips. And she wasn't lying about being plenty wet, she was practically dripping. I guess the prospect of getting nailed by her brother really turned her on, this whole thing certainly had me turned on. I was rock hard and it took all my strength not to just shove my cock in her pussy and have my way with her as I ran my member along the length of her dripping wet slit. And her constant sexy moaning certainly wasn't helping my resolve, though I assume it must've been just as difficult for her.

When I finished, my cock was absolutely soaked in her fluids. I realigned my cock with her puckered asshole and began slowly pushing my tip inside. Ashley let out a sharp yelp as her tight asshole stretched around the tip of my cock, I stopped for a moment to make sure she was ok.

"It's alright, just keep going, bro." she said, looking back to reassure me.

I continued my slow steady push, inching more of my cock in her little by little. The natural lubrication provided by her dripping wet pussy was certainly doing its job but her ass was tight, way tighter than any pussy, it felt almost like my cock was being held in a vise-grip. She continued moaning and grunting as inch after inch of my cock squeezed its way into her narrow anal canal. The pleasure I felt as her asshole constricted around my shaft was unreal, I'd never felt anything like it. With all 9 inches of my cock buried in her tight asshole, it was equal parts pain and pleasure for me, but for Ashley it seemed she was feeling more pain than pleasure.

"You okay, Ash?" I asked, trying not to move a muscle.

"Yeah... just.. give me a minute.. I think I underestimated your size, it'll take a bit to get used to." she panted as she spoke.

"Well look Ash, we can quit anytime you want." I said, not really wanting to quit, but willing to for her sake.

"Don't you dare, Alan. We're doing this." she said, turning back to look me in the eye.

I could see the determination in her face, I knew not to argue with her. That determination in all things is partly what made my sister so attractive. What? Who says you can't admire a girl just because you've got your cock buried in her ass? Hell, if a girl's willing to put herself through that kind of discomfort for you, you better admire her, treat her like the goddess she is.

"Ok" I replied simply.

I held still for several minutes, waiting until she became acclimated to my girth. When she finally gave me the go ahead, I could feel that she had loosened up a little bit, not much though, but at least she didn't seem to be in pain so I assumed it was enough. I began by slowly pulling my cock out almost all the way before slowly pushing it back in. I repeated this several times, Ashley letting out high pitched moans with each push. I was completely dumbfounded, her I was, I was actually doing it, I was actually fucking my older sister in the ass. I could hardly believe it.

"mmm... fuck.. your big cock feels so good in my ass, bro" she said between moans.

I took that as a sign of encouragement, so I upped my pace.

"ooh yeah.. fuck my ass! Fuck my ass, bro!" my sister exclaimed.

With even more confidence, I grabbed my sister's hips and held her in place as I began thrusting my cock into her tight ass faster and faster. Her moans turned into cries of pleasure, as my cock slid easily in and out of her asshole with increased vigor.

"ahhh.. fuck yes! You like having your big cock in your sister's asshole, don't you little bro? I bet mom never let you do anything like this." she said as she panted and cried out in pleasure.

"hnghh.. Only you, sis!" I exclaimed with a grunt as I continued thrusting.

"Yeah? ...not even those little sluts at school let you fuck em in the ass?" she continued questioning me amidst her moans.

I wanted to correct her and tell her the girls at school aren't sluts, but now was not the time for that.

"No! ..You're the only one, sis!" I cried out.

"mmm.. fuck.. that's cuz no one can take care of you like your big sister can" she responded.

At this point I was pounding my cock into her asshole as fast and hard as I could. The bed was shifting and screeching against the hardwood floor with each powerful thrust, if I hadn't been holding her hips, my sister surely would've taken a nosedive off the other side of the bed. I held her firmly in place and her tits shook violently as they hung beneath each time I drilled into her. On my part, the pleasure was so intense, there was no way I'd last much longer.

"hnghh.. fuck.. I'm gonna cum soon, Ash!" I warned her.

"That's good, baby. Fill your big sister's tight ass with your cum!" she cried out.

With that, I came to complete stop, my whole body tensed up and with a guttural moan I began shooting my hot load deep inside her asshole. My body jerked violently with each shot. After about 4 shots of cum, I'd completely emptied my balls into her ass. I let my limp cock fall from her puckered hole and collapsed onto the bed, panting and trying like hell to catch my breath.

"So.. this is what all that racket was when I walked in the house." a voice said from the doorway.

Startled, Ashley and I simultaneously turned our heads to see whose voice it was. We were both surprised to see that it was none other than mom, still in her gym clothes, standing in my doorway with a weirdly self-satisfied grin on her face. The room was completely silent, with exception of me and Ash's labored breathing. I don't know about her, but I was scared shitless. Our mother had just caught us doing something no mother should ever witness their kids doing.

"What? You didn't think I could just let you keep him all to yourself, did you?" Ash spoke up first, moving from her bent over position to a seated one.

Mom was silent, a slightly surprised expression on her face. She had no idea that Ashley knew about us. She just stood there with her arms crossed in front of her, how would she react to this? I wondered.

"Yeah, that's right. I saw you two in the garage last night." Ashley said, nodding her head with the same self-satisfied grin our mother had just a moment ago.

"So, what? You thought you'd move in on my territory?" mom quickly countered.

I was speechless, were they fighting over me? Although, it didn't sound like a real fight. I was so confused and I couldn't help but feel a little worried.

"He's not yours anymore, mom." Ashley said, reaching over and firmly grasping my softening cock in her hand.

I gasped as she grabbed my cock. My mom and sister were having this back and forth, like they were fighting over me, only it seemed more playful than anything else. Where was this going? It's obvious that Ashley was baiting my mother, but what did she hope to accomplish?

"hmm.. is that so? Sounds to me like someone is being a naughty little girl and needs to be punished." mom said, uncrossing her arms and taking a step forward with a mischievous grin.

Then it hit me, me and Ashley's earlier joke about her being naughty. This is what she wanted, she wanted mom to "punish" her. But what exactly did that entail?

"Get back on your hands and knees, Ashley." mom said.

"Oh? What are you gonna do?" Ashley responded, leaning towards me with her mouth open, making like she was about to start sucking my cock.

That was the last straw. The mischievous grin vanished from mom's face. She looked serious now. She was no longer in "mom-mode" this was mom the headmistress, the HBIC.

"Ashley Marie Campbell. Do not make me tell you twice." mom said sternly, now standing at the edge of my bed.

Mom never used our full names, except for when we were in trouble. And it must've worked, because without another word Ashley let go of my cock and once again assumed the position on her hands and knees. Mom placed one hand on Ashley's lower back, then wound her other hand back before bringing it down hard on my sister's bare ass. Ashley let out a yelp as the clapping sound of mom's hand impacting her flesh echoed off the walls.

"Have you learned your lesson? Or do you need another?" mom asked, winding her hand back again.

"What lesson?" Ashley said, looking back and smiling at mom.

"I wasn't aware I raised such a smart ass." mom said as her hand crashed down on Ashley's ass once again.

This time, mom didn't say anything else, she just wound her hand back for a third time and smack Ashley's ass again. Then a fourth time, and a fifth, a sixth, and a seventh time. Ashley yelped and cried out with each slap, but the look on her face said she was enjoying it. I was dumbfounded, I had no idea what to make of this.

"Yeah.. you've been a bad girl, haven't you?" mom said, slapping her ass again.

Ashley didn't respond, unless you count a smart ass grin as a response. Mom continued spanking her, again and again, each time just as hard as the one before it. To be honest, amidst my sister's cries of pain and pleasure, I lost count of how many times mom had slapped her ass.

"Yes! Mommy! I've been a bad girl! Please punish me!" Ashley cried out as mom's hand collided with her ass again.

"Yeah? And whose is he?" mom asked, unleashing a flurry of slaps.

"He's yours, mommy!" Ashley exclaimed.

"You're damn right he's mine. Are you sorry for taking something of mine without permission?" mom asked, continuing to spank my sister's now blood red ass.

"Yes, mommy! I'm sorry!" my sister cried out.

They were no doubt talking about me. Talking about me as though I wasn't lying in the bed next to her, much less in the same room. I just watched, utterly shocked by what I was witnessing.

"Did you like having his cock in your ass?" mom asked.

"Yes, mommy! I loved it!" Ashley responded.

"You loved what?" mom asked, spanking her ass again and again.

"I loved having Alan's big cock in my ass!" Ashley cried out.

"I bet you did, you little slut. Alright, I think you've had enough." mom said.

Mom had finished spanking Ashley, who looked to be in pure ecstasy. Then just when I thought it was over, mom grabbed Ashley's asscheeks and spread them, I could see my cum leaking from her puckered asshole. Mom then leaned in and began licking her asshole. I was still in disbelief, this had just got a lot hotter. Ashley moaned as mom licked and sucked my cum from her ass. Mom kept at it for several minutes, swallowing every bit of my cum as she cleaned it from my sister's asshole.

"Alright, you two come with me, this bed isn't nearly big enough for the 3 of us." mom said as she finished up.

Mom left my room and made her way downstairs. Once again it was just me and Ashley alone in my bed, we just sat there staring at one another. Ashley left first, she climbed out of my bed and almost sprinted down the stairs in pursuit of mom. Meanwhile, I was still frozen in place, I didn't quite know what to do. There's no doubt I was turned on, but that little voice in my head who told me how wrong all this was kept telling me to just stay put. But I also remembered what my sister had told me, that I needed to stop playing the martyr and feeling guilty about everything, that I should just have fun with it. I admired my sister's free-spirited attitude, she didn't seem to worry about anything, I wished I could be like that.

I thought on that for a while, weighing all the options. I compared the pros and cons of my sister's differing lifestyle to that of my own. I was only 18, still a kid in the grand scheme of things, I still had time to change the way I lived. I needed a change. I had to come to terms with who I was at my core, otherwise it'd kill me.

I am a pervert. Time to stop fighting it.

In the end, I decided to take a page from my sister's book. I got out of bed and began making my way downstairs and entered the hallway leading to mom's room. I heard subtle moans coming from my mother's room, they'd already gotten started. I approached my mother's room at the hall, the door was already open and I could see that mom was naked, laying in her bed making out with my sister. I entered the room and walked over to the bed. They were naked and I was still naked, so I just climbed into bed with them. Mom and Ashley stopped kissing as they finally noticed me.

"There you are, I was beginning to worry you wouldn't show." said mom as she and Ashley scooted away from one another making space for me to lay down between them.

I laid down on my back in the space they'd made for me. Mom leaned her face in towards mine and began kissing me, parting her lips and allowing my tongue access to explore her mouth. We kissed like that for a couple of minutes, my tongue in her mouth and hers in mine.

"He's mine, but I suppose I can share him with you for now." mom said to my sister, breaking our kiss.

I then began kissing my sister in much the same way I kissed our mother. I spent the next several minutes switching between the two, making out with both of them. They then leaned over me and began making out with each other. As they made out I began caressing their bodies with my hands, eliciting a moan from each of them. I began sucking on my sister's nipples as I continued to grope mom's tits with my hand.

After a couple of minutes mom broke her kiss with Ashley and changed position so she was straddling me. She then used her hand to guide my rock hard cock into her dripping wet pussy. She let out a sigh of pleasure as my cock slid easily into her hot pussy. I grabbed mom's hips to help steady her as she began impaling herself on me, taking my full length deep into her snatch. She threw her head back and closed her eyes and kept her hands planted on my chest as she steadily raised and lowered onto me over and over again, letting out high pitched moans each time she descended on my thick cock.

Ashley, surely feeling left out and in desperate need of release, began straddling my head and lowered her soaking wet pussy onto my face. I reflexively opened my mouth, and she began moaning as soon as I started licking along her trench. This was the first time I'd gotten to eat my sister's pussy and I gotta say the taste was magnificent, indescribable really. I quickly found the narrow opening of her pussy and inserted my tongue, I began licking the inside of her pussy as she began moaning louder. Ashley then started grinding her pussy on my face, forcing my tongue to go deeper, and she only ever let up to so I could breath every once in awhile.

Ashley was positioned so she was facing mom, and the two of them began making out as they used me to pleasure themselves. I didn't mind being used by them, who wouldn't want to be used like? There we were, my mother and sister french kissing and caressing one another as mom quickly impaled herself on my cock and my sister ground her pussy against my face. We were all connected in one way or another, it was almost like the 3 of us had become one person, each of us moaning and breathing heavily in unison, making our own quick and disjointed movements. To an outsider, I'm sure it probably just looked like a sweating moaning writhing pile of flesh, but to me it was easily the most erotic experience of my young life. It may not have looked pretty, but damn if it wasn't hot.

As I moaned in response to the mutual pleasure my mother provided, I continued licking my sister's hot soaking wet pussy, both mom and Ash moaning into each others mouths. After a while I stopped tongue fucking Ashley and went back to licking along her slit, enjoying the taste and feeling of her juices as they coated my face.

"ahhh fuck yes!" Ash cried out in pleasure, breaking her kiss with mom as my tongue discovered her clit.

I flicked my tongue across her sensitive clit and sucked it into my mouth, as my sister moaned and writhed in response. My sister hadn't cum yet, even after I fucked her and mom ate my cum out of her ass, and when her climax finally did come, it hit her hard. With a scream of pleasure, she stopped grinding and just sat still on my mouth, her tense body began tremble and convulse uncontrollably as her delicious sweet tasting hot creamy cum poured onto my face. I mean, she'd released the literal floodgates on me, I had to lick up and swallow as much of her juices as I could just so I wouldn't drown in it. And when she was spent she just collapsed to the side, one of her limp legs still stretched across my chest as she lay there panting.

It wasn't long after that, that I began to feel my own release approaching.

"Mom, I'm gonna cum!" I cried out as she continued riding me with reckless abandon.

"ahh fuck! Baby, that's good! Fill mommy's pussy with your cum!" mom exclaimed, not slowing down one bit.

With a deep inhale and quick exhale, my body convulsed then went limp as I began shooting my load deep into mom's soaking wet pussy. I came even more than I had earlier, coating my mother's insides with my hot sticky jizz.

Mom suddenly stopped riding me.

"hngh.. I'm cumming too, baby!" mom cried out with a grunt as her juices washed over my buried member.

Mom went limp and collapsed on top of me as a mixture of our cum leaked from her pussy onto my shaft and pubic region.

After several minutes mom rolled over and laid next to me. When Ashley finally regained her composure she moved so she was laying on the opposite side of me as our mother. As they both cuddled up next to me, they immediately began to fall asleep. Soon enough, I too fell asleep. My face, neck, and chest still coated in my sister's creamy cum; while my softening cock and pubic region was still coated in a mixture of my own and my mom's cum.

It was the middle of the day, yet we slept like babies, cuddled in each other's arms.

To be continued...