THIS IS A LONG READ , SO DON'T COMPLAIN IF U WANNA GET OFF QUICK lol! Srry it took so long, but here it is. I decided to turn this short story into a longer type of story, so I put parts 2 and 3 together so it's not too much dialogue. Constructive criticism only please and enjoy :) (Plz read part 1 first)
“Oh… Shit. Mom, I can explain!” I said as I looked down. Jessie was in shock; still on her knees, and her face and tits were totally covered in my cum! “Okay, Matthew. Explain.” Mom challenged. Fuck! “Okay mom; it’s exactly what it looks like. But you always say we should get along more, right?” I said. I had to think of something, no matter how lame it may have sounded. “Not like this! Jessica, how could you do this to your brother?! You’re the eldest, so I’m holding you accountable!” Mom stated. We were in deep shit, but I couldn’t take my eyes off of my mom. She was what Jessica will look like in 20 years, and I was getting excited again. Right now, she was wearing a white Terry cloth robe and her hair was tied up in a bun. Now Jessie was kind of a troublemaker in school. Mom just told her two weeks ago, one more problem and she would be in deep shit. Near tears (and obviously forgetting she was covered in cum), Jessie said “Mom, Mattie and I-” “Shut your slut mouth! You’re out of here!!!” Mom screamed loudly, and Jessie began crying. This was going bad. I had to do something. That’s when I thought of something. I pulled up my shorts, stood up and said, “Mom, Jessie had absolutely nothing to do with this. I came in her room and forced myself onto her. I told her if she didn’t do what I wanted, I would kick her ass. I’m to blame.” “Mattie, you couldn’t kick-” Jessie started, but I gave her a serious look to shut her up. Mom looked at Jessie, then me. She had such a disappointed look in her face. She waited a moment before she spoke again. ”…I’m sorry for calling you what I did, Jessica. Go clean up. Matthew…pack up your shit. By the end of the week, you’ll be in boarding school.” Mom said coldly as she left the room with Jessie. I fell back on the bed, and started quietly crying. I had no idea she’d react like this. Jessie ran back in the room a moment later after cleaning up and hugged me tightly. “I’m so sorry Mattie! I’m gonna go tell mom this was all me. I’m not letting you take the fall.” She whimpered. “Hey, it’s okay. I can take care of myself. You’re on your last strike. I had to look out for you.” I replied as I stroked her hair. “I’ll wait for you…” Jessie whispered as I chuckled. “You already have a boyfriend. How can you wait for me when you’re already taken? Hey, I’ll go and maybe mom will get me out before term is over?” I said.
That definitely wasn’t the case. By the time I got out of boarding school, I had just turned 16. Three fucking years! Mom elected for me to stay there for summers as well, so I never got to go home. Mom’s driver came to get me from the airport, and I had to get his attention because he didn’t know how different I looked. I was now proudly nine inches taller at 6’2’’, 180 pounds of pure muscle. 250 push-ups and sit-ups a day will do that to a person. Plus my blonde hair was jet black and gelled up in a fauxhawk like the stars of Jersey Shore. You’d think I hated my mom, and for a long time I did, but now I didn’t. She’s a traditionalist, and I understood her freaking out like that. I’ll just be happy to see her…and Jessie. I got frequent secret letters from Jessie because I only got to see her two weeks a year on required breaks between class roster changes. She was still seeing that tool Mike, and the longer time passed the more her letters went from a lover back to a sister. I told her about my girlfriend Amy, who went to the academy as well, but she got out 6 months before I did. Amy lived about an hour away, and I couldn’t wait to see her either. As our driver pulled up to the family estate, I was so nervous. I walked right in, and there they were in the family theater with their significant others, watching a movie. “I’m home!” I yelled, so they could hear me over the surround sound speakers. When Jessie got up, her crystal blue eyes locked in on mine. She looked like she saw a ghost. She immediately broke into tears and ran to me. Thinking she was going to hug me, she charged me, knocked me down and started wailing on my arm. What a welcome home, right??? But this time was different. I was way bigger than her, and at school I became very good at Greco-Roman style wrestling. I easily worked out of her hold, and pinned her arms over her head in submission. I was so close to her face; she smelled like lavender and vanilla. She was more beautiful than ever. And, remembering where I was and where the hell I just came back from I jumped off of her. She looked at me in total shock, like I was a new man. And I was. “Jesus bro! You’re a fuckin giant! You made me jump when I heard that voice- so deep!” she stated as she rubbed her wrists and finally hugged me. She was shaped exactly the same, except she seemed a little more toned and her hair was cut into a bob the length of her jaw bone. I laughed a little and said “I guess I did get a little bigger.” “Hello, Matthew. I take it your flight went well.” My mother interrupted and stepped in between us. “Hello mother; and yes, it was just fine.” I replied as I bent down and kissed her on the cheek. “Matt, let’s start over please. Keep the past behind us?” she asked as I smiled. I’m no fool; I knew this was a ploy so she wouldn’t have to act like something happened between her children two years ago. “Of course, mother. Who’s that guy with Mike?” I asked as I gestured to the men staring at me like I shouldn’t be here. “That’s Grant, son…My fiancé.” Mom replied. I nodded and walked over to the guys and shook both of their hands as I was taught in school. But I gave them the coldest stare I could muster up. A very territorial look, like the Alpha Male was back. “Well, I’m sure you’re tired from your flight, Matt. Why don’t you go get a quick nap and get out of that uniform, ok honey? Dinner will be ready in about an hour.” Mom suggested as I nodded and said my goodbyes, and then headed to my room.
I decided to walk around the house the long way to my room. My family was very well off. Our house has maybe ten bedrooms in it. As kids, we all slept in the same wing so mom could keep an eye on us (which got me in trouble in the first place), but now mom sleeps on the other side of the house. To take the long way, I’d eventually have to pass her master bedroom. Everything seemed the same, then I had to remind myself I’ve only been gone for three years; it wasn’t like I had left for war or something. I said hi to some of the house staff, including Isabella, the housekeeper. She was a pretty lady, maybe 50 or so. As I passed my mom’s room, I thought about truly trying to bury the hatchet, but apparently Grant had other plans for my mom. Her door was wide open, and there was my mom on her bed, getting the holy hell drilled out of her from behind by her fiancé! I ducked behind the door and looked around. Well, in their defense Jessie and I were on the other side of the estate so there’d be no way we could hear them even with the door open. I’m sure they weren’t expecting me to take the long way to my room. I had to make a mental note of that fact though…
Really quick, let me tell you about my mom Kristin. She’s a gorgeous woman at 38. Mom’s¬¬ a very stylish, high class woman. She always wore the best clothes to do justice to her body and curves. She stood about 5'7 and was I'd say about 130 pounds. She had long bleached blonde hair. She was the kind of woman that turned heads in every room she walked in. Her tits were awesome; perfect perky c's. She was always wearing blouses that let just enough of them show to keep you wondering what lies beneath the fabric. But at this moment she wore shiny leather boots that came up to her thighs, a black leather corset and her hair was tied into a ponytail. Grant was about 6’4 with a slender build and salt and pepper hair, maybe 45. This guy was really pounding my mom! She was screaming at the top of her lungs! “Fuck your Mistress, you fucker! Fuck me harder!” she wailed. “Yes, Mistress!” Grant replied. It took everything I had in me not to laugh. It was a sight to see. But my head was right back in the game when mom yelled “That’s right; put it in my ass! Your Mistress loves it in the ass, doesn’t she?!” “Yes, Mistress! Do you like it when I-” Grant started, but Mistress, I mean mom, cut him off. “Shut the fuck up, and speak when you’re spoken to! Now lay down, so I can ride your dirty fuckstick until I cum!” He lay with his feet towards the door, and mom rode him cowgirl style with her head facing the door. I was impressed! She rode him like a woman possessed, telling him to pull her hair and smack her ass. This was an entirely new side to mom, and I was so turned on. Then suddenly, she looked up and saw me. I had that deer in headlights look on my face. Fuck. It looks like I’m going back to boarding school. But, she just smirked and rode Grant even harder and faster without taking her eyes off of me. “Fuck, Matt, I’m coming!!!” she screamed. Was I hearing things, or did she just say my name?! “I’m coming too, Mistress!” Grant said as he dumped his load into my mother. Holy hell that was hot. Grant spoke up first. “Hey babe, it sounded like you called me Matt a second ago.” Red in the face, my mother replied. “Did I? I’m sorry lover; I just have my son on the brain with him coming home today. I’ll make it up to you later. But right now, I have to go check on dinner.” I guess that was my cue. I quickly made my way to my room.
My room was exactly the same; even the bed was messy, like I just slept in it. I thought about going to bed, but sleep was the last thing on my mind. All I could think about was Jessie, and that look in her eyes a moment ago when I had her pinned to the ground. And mom riding grant… And I was in a room alone for the first time in months, so I wanted to take advantage of it. I immediately stripped off my clothes and laid on my impossibly soft bed with thoughts of my sister on my mind. Now I was proud of my cock at 13, but now? Even I was impressed. Now I was at a whopping 8 inches, and still extremely thick. (Amy made me measure one day at school) I started to stroke it fast; at this pace there was no way I could last very long. I was really getting into it, when my door blasted open and Jessie walked in. “Hey, bro. I was wondering-holy mother of God!” She said as I covered myself with a blanket. I cannot believe this is happening- again! “Nobody fuckin knocks in this family?!” I said, as she stared at the tent in my blanket. “I’m so sorry Matt! I’m such an idiot!” she replied as she finally covered her eyes with her hand. “It’s cool, sis…but what did you want?” I asked. “Um…Oh yea; Mike’s going home now, so I wanted to know if you wanted to ride with me. But, I see you’re…um…previously indisposed. I’ll just see you in a bit.” She stated as she rushed out of my room. I sat in silence for a while, and after deciding against finishing, I laughed for what seemed like forever.
Dinner with mom, Jessie and Grant was totally uneventful. Jessie wouldn’t even look at me, and Grant was kissing my ass something hardcore. I guess he’s a cool guy, though. After we had dinner, mom asked if I wanted to join them for a movie, but I politely declined, saying I was jet-lagged. I went into my room and fell asleep. It was about 11 that night when I awoke. Jessie had to be in her room by now... It’s been so long since that night, and I wanted her now more than ever. But I was still unsure if she wanted me in that way anymore. Well I was about to find out.
I walked over to my sister’s bedroom and quietly stuck my head in. She was on the phone with her boyfriend. But the real news was that she was totally nude! Her tummy was flat and toned, her perky tits (which did look bigger) sat high on her chest, and she was totally shaven downstairs. I never got the chance to go down on her before, and with Amy I’ve become a master at it. Her eyes were closed and she was slowly rubbing her clit. I’m guessing they were having phone sex, but she totally sounded like she was faking it. “Oh yes baby. I wish your enormous cock was here inside of me…Yes. You’re the man. Ooh.” She said quite unenthusiastically. I figured I already did three years at boarding school; I could do another two if I got caught. But I had to have my sister NOW! I quickly crawled into bed with her and dived face first into her folds. She jumped so violently that I thought she was going to fall off of the bed. She opened her eyes wide and tried to squirm away from my tongue, but I held her hips in an arm vice. She wasn’t going anywhere. She started moaning loudly. “Ohmygosh your tongue is godly!!! Please suck my clit; please!” Jessie moaned as she started grinding her wet pussy in my face. She was so wet, and my face was drenched almost instantly. I moved up to her clit and inserted two fingers. “Oh God! It feels so good! …What?? Oh, um yea Mike. Ur the best! God I wish you could see how wet I was right now!” she said. I guess she forgot she was on the phone with her boyfriend. It kind of bothered me that he thought he was the reason why she was moaning so much, but I knew the truth so it was okay. I decided it was time for her to cum, so I increased suction on her sensitive clitty. “Oh Mike!!! Your tongue feels too good! Suck my fuckin clit! More fingers, I need more of you!” she whimpered as I withdrew my fingers. It was time for my signature move. As I was sucking her clit, I extended my tongue and started licking and sucking simultaneously. This one drove every girl wild, and Jessie was no different. She grabbed my head and pushed me into her pussy as far as she could and threw her phone down. “Fuck Mike! Oh Mattie, I’m gonna cum! Shiiiit!!!” she said as she grinded her wetness into my face. She rose her butt off the bed, shook violently, then fell back down. She had a look of total satisfaction on her face. I climbed off of her bed and started wiping her cum off of my chin and licking my lips. “Shit, I hung up on him. I’ll call the dumbass in the morning… Mattie, that was…Amazing. And unexpected! What about your girlfriend?” Jessie asked as she covered herself up with a blanket. “What about her?” I asked. “She wouldn’t get mad that you just tongue fucked another girl? Let alone your sister?” Jessie asked and I chuckled. “Something tells me you’ll keep a secret, sis… Call it a hunch.” I said as I winked and left her room. Round one definitely goes to me.
The next morning, I awoke to a tongue sliding up and down my cock. Man, Jessie has gotten really good at this! She started kissing up and down my shaft to my balls, and she gave them a good lick as well. “Oh shit! That feels so fucking good! I missed this so much!” I moaned and she giggled. “I know, lover…Six long months without me…” She said as she continued to suck me. Yeah, six…wait a second. Six months??? “Amy?!?!” I said as I opened my eyes to my beautiful girlfriend. When the hell did she get here? Amy Alvarez, my goodness this woman RAN our school-including the faculty. She really shaped me into the take charge guy I am now. 5 feet, nine inches of sex on heels. This 18 year-old Brazilian goddess had long black hair down to her shoulder blades and golden bronze skin. She looked like Cleopatra in my opinion. If only her brain matched her looks… All curves, 34C tits and an ass that makes grown men suck their thumbs. Perfect in most guys eyes, but she just wasn’t Jessie. “Of course it’s me, Matthew! Who else would be sucking on MY cock- your sister???” she said as she laughed, and I chuckled. If only she knew…She suddenly stopped sucking me off and got off my bed. Dream girl or not, giving me blue balls was not in my day planner. I tried to grab her but she wiggled out of my hold. “Baby, don’t leave me like this!” I pleaded but she winked and left the room. In the hallway I heard her say “I was only told to wake you up!” Fucking bitch. After a very cold shower, I threw on a black tank top, black shorts, black sandals and a black visor (why the hell not?) and flew downstairs.
I decided to pass the kitchen and go for a run. It was a perfect morning so I ran kinda far, but it gave me time to think about things. Amy was in my house right now. A true slut for my cock, there was nothing she wouldn’t do for me. But at the same time she managed to come off as purely sexy and classy. I was coming to realize that, at only 16 I had what every man dreamt about, a woman who would do anything… And Jessie. No matter what I did, she has never left my thoughts for too long. It was her that occupied the majority of my thoughts as I pounded the pavement. Amy was very similar to mom, in that they were always in control, had great figures and were very easy on the eyes. But I was really curious about how far my sister wanted to go, and was excited to see what would happen if I could get her all alone again. I had gotten really hard really quick, so I concentrated on running home and breathing so I could get home without catching a cramp. When I arrived home I had another quick shower and a shave, put on just a pair of shorts, and finally went into the kitchen.
When I got to the kitchen, Jessie and mom were eating. Conspicuous by her absence was Amy. Jessie’s face lit up like a kid on Christmas. “Hey, Mattie! Met the chick you’re fucking! Just left to run errands or some shit! She’s dumber than a bag of rocks!” she said excitedly, obviously imitating Amy. I couldn’t help but laugh. Mom chimed in. “Don’t talk like that, young lady! Matt, you need to go shopping. You can’t fit anything in your wardrobe. So I invited Amy to take you.” She said. Hell no. “Um, no offense to Amy, but she drives like a mildly retarded monkey. I’d rather chill with Jessie today. I haven’t seen my sister in forever.” I replied as I winked at her. Mom shrugged and went back towards her room. “Hold on one second! I had plans with Mike!” Jessie said as she shot me down. I suddenly had an idea, and it was crazy enough that it may work! “Well why don’t the four of us make a day of it then? Shopping then a movie?” I suggested. Jessie thought about it for a while, and then nodded. “We can do that. Just put a muzzle on your dog!” she replied. “I was gonna mention the same thing about your tool boyfriend!” I said, starting getting defensive. She stood up and got in my face.
“You wanna go, little bro?”
“You couldn’t handle it, sis!”
“”You’d be surprised.”
Maybe it was just me, but I felt like the sexual tension was thick enough to cut with a knife. I couldn’t take it anymore. I lunged for her and kissed her greedily, and she kissed me back just as strongly. “Your room, little brother. 20 seconds.” Jessie giggled as she sprinted up the stairs. Not one to be outdone, I darted behind her and actually beat her to the door. I pushed her on my bed. She was wearing a long SpongeBob T-shirt. She always loved her cartoons. I got on top of her and we resumed our make out session. She pulled down my shorts, revealing my cock, glistening with pre cum. “Mattie, you’re so big now… I don’t know if I can take that!” Jessie said as she grabbed it; she couldn’t close her hand around it. I chuckled. I pulled her tee off of her and threw it down, revealing the sexiest pair of lace pink boyshorts. I kissed her again, and said “Oh my goodness you’re perfect…Jessie I need you. I’ve dreamt about this every day for the past-” “Shhh…” she replied with a wink, cutting me off. She may be smaller than me, but she easily flipped me over so that she was on top of me. That was ridiculously sexy to me. She kissed me on the lips softly. With a flip of her blonde hair, she kissed my ear and whispered “I wanna fuck your brains out, stud…” before she stuck her tongue in my ear. God, electric jolts ran through me. I was experiencing something new; something never experienced with the girls I’ve been with. Jessie was on the verge of making me cum without touching me! She let her kisses fall into slow, deliberate trails along my neck, making sure to linger for an extra moment and plant a few nibbles. She was planting shallow kisses on my chest and using her tongue to set me on fire. She abandoned my nipples after a while, and let her tongue trail down my abdomen. She kissed every abdominal muscle I owned. God it felt so good, and I was leaking pre cum everywhere I had to close my eyes and imagine my mom catching us again to calm me down, but it didn’t work. At all. She kissed my bare skin leading up to my shaft (I kept it bare) and I couldn’t take any more of this sweet torture. “Fuck Jess I gotta cum!” I said as I looked down at her. She winked again, and covered my cock head with her warm mouth. I pumped rope after rope of cum in her mouth, and she just took it all while staring me in the eyes. She got off of me and walked to the door. “Wait…I’m not done!” I pleaded. But, she opened her mouth like a kid at the doctor’s office, revealing her mouthful of my cum, swallowed and reopened, revealing an empty mouth! “Yumm Mattie. Your cum always tasted the best. But alas, we don’t have enough time for me to ride you mercilessly like we both want me to do... Mike and Amy are on their way here. But, if you’re a really good boy tonight, when they leave I’ll make it worth the wait. 3 years’ worth, actually. Oh…And let’s get one thing straight. Amy’s just for show. I’m your girlfriend now. See you in a few, little brother…” she said as she picked up her shirt and left my room. …Well, who the hell was I to complain?