“Loooosseerrrr”
My world came crashing down on top of me, my chest tightened and a black void was closing in around me.
I was stood in the middle of my high school corridor, I had just done the unthinkable and asked Vanessa “the heartbreaker” Pollock out to prom. Vanessa was your typical popular high school girl. Tall, blonde, amazing figure, piercing blue eyes, ample chest and big firm ass. Her naturally beautiful face and that captivating smile were now directed right at me. Her finger pointing right in my face. In life we all have moments that we regret, this one was a major one of mine.
“Go to prom with you??” She shouted aloud to make sure everyone around could hear as a small group of teenagers gathered.
“No way on earth would I go to prom with a fat ass like you!!” She continued to laugh in my face. Why would the most popular girl in this school go to the biggest night of her school life with a small dicked virgin like you?!”
Everyone around me was laughing and pointing, muttering to themselves. I was frozen solid, I couldn’t move. I was speechless. My life was over, I wished for the gates of hell to just open beneath me and for me to fall into its firey furnace. Even an angel to flash a bright light and I could disappear forever. Instead my saviour came in the form of my best friend, Logan. His face appeared in front, he was saying something but I couldn’t hear him.
Logan was my only real high school friend, he was slightly smaller than me at just under 6ft tall. He was of much better build though. No body builder but had a decent amount of muscle about him. He had short black hair, brown eyes and a bit of facial hair growth about his face. He was still saying something to me as I slowly came back to my senses.
“Jacob?! Jac mate?!” He continued to say in my face, I snapped back to reality. The noise of dozens of teenagers laughing at me and the chants of “looosserrr” fillingu the corridor.
“What did I do?” I asked completely bewildered.
“You just asked Vanessa out to prom you idiot!!” Logan said snapping his fingers in my face. He had managed to push me away from the group that were still pointing and laughing at me.
I was speechless again. I looked back up towards the group and to Vanessa. Who was still laughing and now had her hand on her forehead in the snap of a L. I turned away from Logan and the group and darted for the exit. As I hurried down the corridor I passed my younger sister of one year. Only god knows how we are related.
I’m 6ft tall, shaggy brown hair, hazel eyes and yes as Vanessa has already so kindly pointed out, i’m a bit overweight. Ache was quite the feature as well. My sister on the other hand, I don’t like to admit it but she is drop dead gorgeous. Brown hair and hazel eyes like me but her figure is one a girl would kill for. Her boobs were getting bigger by the day it seems and she had the peachiest firm ass I’d seen.
“Way a’ go brooo” she said sarcastically as I scurried out of the school.
———
So that all happened about a year ago. The end of my high school life ended in complete disaster. For the rest of my days I hid away from everyone, finished my exams with decent grades and not a chance in hell did I attend prom.
After I left school, I still felt I had to get away and so I went to a different college than everyone else. Best decision I’ve ever done. It’s completely changed who I am. I have a new found confidence in myself, I’ve been able to recreate who I am. I’m doing well in classes and making new friends. Even managed to loose my virginity thank god. I’ve turned a new leaf as well and my figure is completely different. I even go for runs now and can do more way more than five press ups.
I’ve been at college for the past 10 months and Ive got some time off before exams so i’m coming home. I’m going to surprise my mom Audrey, as she has no idea i’m coming back.
I park my black Ford Focus RS, an inheritance funded gift, a couple of houses away so she’s doesn’t she the car outside. I walk up the few steps in front of our house and drop my bag onto the porch. I take a deep breath and ring the bell.
A few seconds of silence pass before I hear my moms voice “hold on a sec, just coming!”
A few moments later the door swings open and she begins to speak “Hi, hello there, how can I….. OH MY GOD, my booyyy!!” My mom lunges out of the house and leaps towards me grabbing me into a tight hug. I quickly return the favour and hug her tightly back. I hold onto her and she begins to shake as the tears of joy and happiness roll down her face. I just hold her close and enjoy the embrace. My mom was a fairly short woman but I have to admit she was a very attractive woman. She was a natural brunette but she had dyed her hair a dark red now. It was tied into a pony tail, which left an open view of her massive chest. DD’s at least. She looked after herself and had a well toned body but her ass was a sight to see, nice and plump.
After several minutes she’s broke the hug and wiped her face “why didn’t you tell me you were coming home!!” She demanded.
“Thought I’d surprise you Mom” I smiled back.
“Oh my god, just look at you!” She stepped back and admired me. “In less than a year you’ve already turned into a handsome young man, not like you weren’t before” she corrected herself. She continued to stare at me up and down and if I wasn’t mistaken I could swear she was checking me out. “Anyway c’mon in and get yourself comfy! Your sister will be home soon!”
We went inside and I dumped my bag by the stairs. The house was still the exact same as it was when I left. My moms dad left her quite a bit of inheritance so we were seen ok. However her ass of a husband liked to drink most of it away and had the nerve to cheat on one of the greatest woman on this earth. Thankfully he left us quite a while back and we haven’t heard or seen from him since, good riddance.
My mom and I sat chatting away for the next half hour or so. Just catching up on what had been happening around town and how I was getting on. I didn’t go into too much detail of all my college life but how much it helped turn my life around. Our conversation was interrupted when my sister, Kaylee, came flying through the front door.
“Mooom, i’m home” she announced, not like the whole street couldn’t hear her slam the door.
“Kaylee honey, come into the living room there’s someone hear to see us!” My mom shouted through to her.
“Unless it’s a tall, dark, handsome man or a prince to whisk me away then i’m not interested”
She complained as she stepped into the lounge.
I turned to face her “Hi Kaylee”
“Mom who the hell is ….” She cut herself short as she narrowed her eyes at me “fatso is that you!”
“KAYLEE!! That’s no way to speak to your brother!” Moms anger filled the room.
“I’m … sorry,” she slowly walked towards me “Jac is that really you??”
“Yup one and only” I smirked as I stood up. My sister used to always tease me about my weight but I knew deep down inside she loved me and especially after the incident last year it must have looked bad on her too.
“When did you get back?” She asked as she held out her arms and I pulled her in for a hug.
“Only been home about half n hour!” I replied, squeezing her tightly before letting her go.
We were a family again. We spent most of that night laughing and joking as family’s do in front of the tv. Eventually it got late and everyone headed off to bed. I went upstairs and into my old bedroom. Switching on the light and it was like I never left. Everything was exactly how it was before I left, maybe just a little tidier than before. Mom must have given it a clean now and again. Just as I was putting some of my clothes away and tossing my t shirt into the laundry basket, a small knock came at my door. I turned to see my mum standing there with some towels.
“Thought I’d give you some fresh towels incase you wanted to clean yourself up at any point” my mom said from the door as she stepped in towards me.
“That’s great mom thanks, could do with a shower soon” I smiled as I took the towels from her grasp and placed them on my bed. I could feel my moms eyes lingering on me and fixated on my body. “You ok mom?” I asked.
“Huh? Yeah sure son” she snapped from her trance, “sorry just been a long day.” She smiled. “Goodnight my boy, love you!” Mom moved forward and pulled me into a hug.
“Goodnight mom, love you more” replied, returning the hug.
My mom held on for a little longer and I could swear i heard a moan or two escape her mouth. She gave me a quick kiss on the check and scarpered out of my room.
———
I slept pretty well that night, only a couple of weird dreams that shook me awake. The main thing on my mind was my mom. What the fuck was wrong with me. I was lying awake that morning and couldn’t get her off my mind. I was imagining her standing at the end of my bed in nothing but a matching pair of purple lace bra and panties. Her 36 DD boobs were begging to be set free. Her hands on her hourglass hips and wanted a handful of that big ass of hers. For a woman in her late thirties she was a vision of pure beauty.
I couldn’t help but start rubbing my morning wood to the image of her. I slowly started to stroke my shaft up and down. It has been a while since I’ve been able to relieve myself and it was staring to feel really good.
“NO!!” I shouted at myself. “You’re not some randy teenager that will jerk off over anything, certainly not your own mother.” I jumped out of bed and grabbed a towel and headed for the bathroom.
Our house had one main bathroom that my sister and I would share. My mom was lucky enough to have her own private en suite.
Luckily the bathroom was free and I could grab a shower. It was just what I needed to cool off and feel fresh.
After my shower, I got dressed and headed downstairs. The house was empty and there was no one to be seen. There was a note on the kitchen table with my moms hand writing on it.
I’m off to work honey, Kaylee’s at school.
Foods in the fridge and all that, just help yourself.
Be home around 5
Love you Jac x
“Oh well house to myself” I said. I headed to the refrigerator and fixed myself some breakfast. Bacon and eggs with some toast. Perfect start.
The next few hours consisted of me mindlessly watching tv, I couldn’t even tell you what crap I was watching. I tried to do some studying for my exams but it felt like nothing was sinking in. It was around three o’clock and I decided that I needed to go for a run, needed some fresh air. Over a year ago I would have happily sat in front of the tv all day long and eat snacks. Not now, now I had the urge to keep active. I put on some loose shorts, trainers and a tight tank top on. I didn’t have any set destination or route, I just set off and ran about town.
I was out for about an hour or so because when I came back my sisters car was in the driveway, an old silver Volkswagen Polo. As soon as I stepped into the house, I could hear the unmistakable laughs and giggles of a group of teenage girls. I entered the lounge and there was silence as the three of them turned to stare at me.
Kaylee’s friend Melanie broke the silence first by whispering to her “who the hell is that hottie?”
Melanie was one of my sisters best friends. 5ft6”, black hair, emerald eyes, small cup chest but still a handful. Her ass was definitely her best feature.
Kaylee turned to her with a small growl on her face and turned back towards me “girls you remember my looser brother, Jacob?”
“No way!” Riley spoke up. Riley was Kaylee’s other best friend. She was the shortest of the three but I would say she had the biggest chest. Whilst I have to admit my sister was the hottest overall. Riley had a certain allure about her. Shiny brown hair in a plete, brown eyes and the most luscious lips I’ve seen.
“The loser got smoking hot” Melanie teased.
“Shut up Melanie” my sister barked.
“Hi girls, Kaylee i’m going for a shower. Girls it was nice to meet you!” I said as I turned away to head upstairs. The whole time I was standing there I could tell that Melanie and Riley couldn’t take there’s eyes off me. Hell I think my sister was even checking me out as well. Oh how times have changed.
Just as I headed upstairs my sister shouted up to me. “Moms gonna be late tonight so dinners on you!”
“Hmph, yeah sure” I said to myself. Once at the top of the stairs I could hear the girls chatting and giggling again.
I stripped off in my room and grabbed an other shower. As I was in the shower and was washing myself. I thought I heard the door creak open. The window to the walk in shower was all steamed up so I couldn’t see out properly but the door was defiantly open a little now. I was about to speak out before I stopped myself. It was kinda turning me on. I don’t know who it was that was watching me, I couldn’t make out who it was but I was certain there was a figure in the doorway.
I tried to make it look like I wasn’t aware they were there but I turned myself so they could see the rough outline of me and my cock through the shower window. I started to soap up my cock and slowly stroked it. After a few strokes and the thrill of someone watching me, even the chance it was my sister, my cock was growing to its full length.
“Holy shit” I could hear a female voice whisper from the doorway.
“Hello” I called out, teasing whoever was there. I didn’t get a response but I hear the door close. I chuckled to myself. I finished cleaning myself off in the shower and headed back to my room.
I dried myself off and threw on a loose t shirt and shorts but I was still feeling a bit horny. In all my life I never thought someone would be watching me, if anything it would be the other way around. Which I must admit I have done to my sister a couple of times. Probably should be ashamed but I was a young horny teenager that wasn’t getting to see any girls in real, any time soon. Online porn was my only real release.
Thinking about it again my cock started to twitch and I had to let loose. I went over and closed the door. Then an idea came to me and I opened it back up slightly. I then went and sat at my desk and positioned myself so if someone did watch again they could see everything but I wouldn’t catch their eye.
I got my computer running and put my headphones in. I went onto my favourite free porn site and started watching some videos whilst I slowly played with myself. After a while of browsing through different videos, I found myself watching a mom and sister threesome. It was hot as fuck. You couldn’t tell from watching it that it was mom and sister but with the sound on the story set it up that way. I was really turned on now so I picked up the pace. Stroking faster and harder along my shaft.
I had one headphone in and one ear free, and sure enough I could hear someone at my door. I didn’t want to turn around and scare them away so I moaned louder and worked my shaft faster. I turned my head slightly to get a glance. I couldn’t make out the face but someone was watching me. I slyly turned down the volume on my headphones and I heard soft moaning. I wanted so bad to turn around and see who it was but some part of me told me not too.
Knowing I was being watched now I really turned up the act. I increased my pace and moaned louder so my watcher could hear. I closed my eyes and started to imagine that it was Riley sucking my cock, her red luscious lips working their way up and down my shaft. I could feel my balls start to tighten and I knew I was close. I now imagined It was Melanie sucking my cock faster and faster. Just before I was about to cum, images of my mom and sister started to fill my mind. The image of these four amazing woman sent me over the edge and I exploded. Shot after shot of cum shot out, I was lost in the moment to even realise where my cum was going,
“Fuucckk” I gasped. That felt really good. As I came back to reality, I couldn’t help myself and checked the door. It was Riley that was watching me, her hand down her pants. She was so lost in the moment she hadn’t realised I was looking at her.
“Shit” she whispered as she disappeared behind the door, followed by footsteps running away. I smiled to myself then turned my attention back to my computer.
“Fuck me” I said, there was strips of cum over my desk and on the floor. Even some on my tshirt, there was quite a lot.
I made quick work of cleaning it all up and chucking my t shirt into laundry basket. Throwing a new one on, I headed downstairs to get a drink and see what the girls had to say for themselves.
When I got to the bottom of the stairs my sister shouted at me from the lounge “Jacob, did you say anything to Riley?”
“Eh no?” I replied, “why?”
“Well cause she came back downstairs and just made the excuse she had to leave in a hurry!”
“How’s that my problem?”
“Was just asking dickhead!” She huffed back.
“Maybe you should ask her then” I shouted as I made my way to the kitchen.
“Fuck you, I’m taking Melanie home” was all I heard, followed by the front door slamming.
“The fuck is wrong with her?!” I said to myself.
I grabbed a bottle of water from the refrigerator and downed about half of it. Then there was tapping sound coming from the back door. I went over to check through the window, it was Riley.
“Riley?! What are you doing?” I asked as I opened the door.
“I’m here to offer an apology ‘cause i’m so embarrassed” she shyly replied.
“Apology for what?” I fained ignorance.
“Well for me watching you like ten minutes ago as you played with yourself. I couldn’t help it. I had seen you in the shower but wanted a better look.” She went on “I just got carried away when I saw it and it was so hot that I couldn’t resist touching myself.” She confessed.
“So you spyed on me in the shower?” I grinned.
She simply nodded.
“Then you wanted to see the real deal and ended up getting carried away as I stroked my big hard cock” I said.
She nodded again and bit her lip.
“So what can I do for you then?” I smirked
“Can I see it again?” She quietly pleaded.
“Hell why not” I simply dropped my shorts and let my cock hand free. I was full of unfounded confidence.
“Her eyes widened, it’s so big” she let out a small groan.
“It’s get bigger” I told her with a wink.
She just stared at it with amazement and began to reach out her hand but was stopped when I pulled my shorts back up “heeyyyy” she cried out.
“Not here” I said, her face went sad “in my room” I quickly replied.
Her face grew a big grin and we closed the back door and skipped up stairs.
Up in my room I closed the door behind me as Riley took a seat on the edge of my bed. She was wearing tight denim jeans, a cute white tank top and a denim jacket which she took off and placed on the bed.
I walked over and stood in front of her. “You can pull them down this time” I winked at her.
Riley bit her lip again and reached forward. She didn’t go for the waist band but ran her hand over my crotch. My cock twitched at her touch. Her hand pressed against my bulge and she just stared at it in a trance.
Riley then reached her hand into my shorts and grabbed my cock, a moan escaping her mouth “it feels so thick.” She used one hand to pull my growing member out and used the other to pull my shorts down with a bit of help from me.
As my shorts feel to the floor, Riley just held my cock in her hand and admired it with amazement. Her hand slowly started to move and I found a moan of my own escaping. Even after just jerking off no less than fifteen minutes ago, my cock was growing quickly in size.
Riley squeezed it in her hand as it grew to full length of about 9 inches. “It’s so big” she moaned. “The looser has a massive dick” she teased.
I just chuckled, as an other moan escaped my mouth as she slowly stroked up and down my length.
“It’s so impressive” she said, stroking it a little faster. “It’s so much bigger up close then watching from the door” she confessed.
“How big did you think it was?” I questioned her.
“From what I could see through the steam and in your room, it looked like the biggest I’ve ever seen.”
“I knew someone was watching but didn’t know who.” I told her, “it turned me on though”
“Really?” She sounded surprised.
“Yeah why do you think I left my door open slightly when I jerked off.”
“You knew someone would watch?” She asked.
“I didn’t know for sure if someone would or who it would be but the thrill of one you girls watching me play with myself was a big turn on. I wasn’t disappointed either! Did it feel good?”
Riley’s face went a shade of red as she looked down shyly. “Yeah it felt really good” she finally spoke “but this is already feeling so much better.”
A few moments of silence passed as Riley stroked my cock. Her hand was soft and tight on my shaft and it was feeling really good.
“Suck it baby!” I half told her, half wished she would.
Riley looked up to me with her brown eyes and with a wicked grin took the head of my cock into her mouth.
“Fucckk” I gasped. Her big luscious lips wrapped around my cock felt incredible. Her head started to move up and down my cock. I’ve had a few blowjobs but this was the best so far. Those lips were giving even better suction.
She reached her hand up and started to cradle my balls in her hand whilst she worked the shaft with her other. Fuck this was feeling good. She could only get about three quarters of my cock in her mouth before she gagged to much and let go. My cock was covered with salvia and her eyes were watering slightly.
“Fuck baby, it’s so big” she said catching her breath, still stroking me.
“It feels so good” I told her and with that she took my length back into her mouth. Sucking harder and faster than before. Working as much of my shaft as she could. Looking up at me in the sexiest way as she tried to take me deeper.
She broke off again trying to catch her breath. I grabbed her and pulled her up into a kiss. It was sloppy and it tasted slightly salty from my dick being in her mouth. We kissed with heated passion as our tongues fought against each other. My hands were roaming all over her body. Grabbing handfuls of her ass as she stroked my cock between us. I was horny as fuck now and need to fuck this little cock teaser.
I broke the kiss and started to kiss her neck as I unbuttoned her jeans and fumbled to pull them down. She helped me by standing out of them and quickly pulled her white panties off too. I stood back up and clashed lips with her as my fingers found her sopping pussy. My hand was drenched instantly as I found her clit and teased her.
“Mmmmm fuck Jacob” she moaned as her head fell back. “It’s feels so much better with your hands instead of mine.”
I turned her around and bent her over the bed. She quickly stood back up “have you got a condom?”
“Shit, eh yeah” I didn’t even think about that. Luckily I had one in my wallet and pulled it out. Riley got back down on her knees and sucked me harder before reaching for the condom and taking it from me. With my cock still in her mouth she tore open the condom. She slowly placed it on and whilst looking up to me, stroked it a few times.
I didn’t like to use condoms but if needs must I will. I grabbed Riley and pulled her up again and bent her over my bed. Even though she was the shortest of the girls. Bent over my bed she was the perfect height for me to sink my cock inside her. I rubbed the tip of my cock against the entrance of her pussy a few times before I slowly pushed in.
Riley threw her head back in pure pleasure at my intrusion. I pushed my cock deeper and by god her cunt was tight. I felt it hugging my full length and slowly stretching as I pushed all the way in.
“Mmmmm fuck baby, you’re cock feels magical” Riley groaned as her pussy got used to my size.
Once I felt she could take it, I started to pump into her faster. Our bodies clashing against each other as I slammed into her. The condom was masking some of the feeling but I was still getting so much pleasure out of fucking my sisters friends tight little pussy.
Riley balanced herself on the edge of my bed as I doubled my efforts. Fucking her harder and deeper. My balls slapping against her every time I bottomed out inside her.
“Oh my god Jacob, yes fuck me, fuck me!” Riley groaned loudly as my cock continued its assault on her teenage pussy.
Suddenly I heard the front door slam, I stopped in my tracks and Riley stood up. My cock was still inside her and I covered her mouth with my hand. We heard footsteps coming up the stairs followed by my sisters voice.
“Jacob that’s me home!” She shouted through my door.
“Sssshhh” I whispered to Riley as I slowly started to fuck her again. “Ok Kaylee” I yelled back. Riley squirmed in front of me and was moaning against my hand.
“Can we have dinner soon?” My sister asked.
“Mmmm sure” I replied, holding back moans of my own as I fucked Riley deeper at a agonisingly slow pace. “What do you want?”
“Pizza will do”
“Ok i’ll run out in abit and grab us some.” Riley moaning harder against my hand.
“Thank you” she paused “Jac, it is really good to have you back!” She said sincerely.
“It’s good to be back sis” I replied as I heard her walk away.
I pulled Riley close to me and whispered into her ear. “We need to wrap this up. Can you behave and keep yourself quiet?”
She whined and nodded as I let go of her, bending her back over the bed. I quickened my pace again and fucked her hard. She reaches down between her legs and starts to rub her clit.
With my continual fucking her with force, I feel my balls about to tighten. I slam deep inside her as I explode inside the condom.
Riley let’s out a low groan of her own as she has her own orgasm. We do our best to hold in our screams of pleasure as I fall onto her, my cock still deep inside her.
“Mmmmmm wow” Riley moaned from beneath me.
“Not such a loser anymore” I teased.
“Oh fuck no, far from it” she said, working her way from underneath me. I stood up of her and helped her to her feet. We shared another heated kiss, not as passionate as before but just as hot.
“Let me get that for you” she smiled and she pulled the condom off my limping dick. “Quite a load there” she smirked as she showed me the used condom. She tied the end and chucked it away into the bin.
“You’ve done that before” I joked.
“A girl has her needs too” she winked as she gave me an other quick kiss.
We then got changed quickly and quietly. I snuck Riley downstairs and shouted up to Kaylee that I was away.
“Ok please hurry, love you” was all she shouted.
“Love you too” I shouted back as I ushered Riley out of the house and into my car.
I drove Riley back to hers, the chat in the car was actually pretty mellow considering we had just fucked. Just about how college was and how her last year of high school was.
We pulled up outside her house and she leant across and planted a warm wet kiss. I parted my lips inviting her in. Her tongue found mine as we kissed with more passion.
She broke the kiss “give me your phone number please” she asked as she pulled her phone out.
I gave her my number and we kissed again briefly before she got out and ran into her house.
“What a welcome back” i said to myself as I drove off, heading for the local pizza place.