Dad has always been a gambler and I guess everything happened because he heard me make a bet with a friend on the phone. My name is Ryan and I am sixteen, dad had two friends that were neighbors with hot daughters. They were always together and I heard them bet on sports all the time. I guess it was a do as I say and not as I do type of thing.
My mom Jade was hot but her and dad were always fighting. Anyway, dad wanted to teach me a lesson. After I hung up he cleared his throat and I looked at him and his two friends, “Betting can get you in trouble Ryan.”
I grinned, “I always win.”
They looked at each other and dad smiled, “Would you like to bet with me?”
I snorted, “I don’t want to bet for money. If you had something I wanted I would bet all the next weeks games on it.”
He pulled out his wallet, “Your allowance for the coming summer. I’ll match it with a hundred.”
I shook my head as I turned to head back to my room, “I already won five hundred from the guys at school.”
He called after me, “Two hundred.”
I looked at him, “I’m going to be stuck at the cabin all summer. Where would I spend the money?”
I went back to start studying since we only had a week of school left. I could hear dad and the other two men arguing and then they went quiet. They came to the door and dad grinned, “Your five hundred for your mother.”
I looked at him and he grinned almost evilly, “You can fuck her whenever you want if you win.”
I sat back as the idea made my cock hard, “And if I lose?”
He smiled, “I get the five hundred.”
The other guys cleared their throats and I glanced at them and then smiled at dad, “deal, but if she refuses you pay me ten times my bet.”
Dad laughed, “Done.”
Mr Johnson cleared his throat, “I want in on this.”
I opened my drawer and pulled my check book out, “I have a thousand in the bank. What did you have in mind?”
He smiled sweetly, “My daughter for the thousand.”
Mr Thomas pushed him, “Hey!”
Mr Johnson glanced at him and then shrugged, “Okay, my daughter for five hundred.”
Mr Thomas nodded, “Me too.”
I smiled again, “Same deal as dad, if they refuse you pay me ten times my bet.”
They nodded and I pulled up the listed games for the up coming week. They came to look over my shoulder as I began selecting teams to win. When I finished I printed four copies and handed the list to each of them and stuck mine on the wall above my desk, they left whispering that I was a sucker. I smiled because I had selected my teams from a betting service.
Each day I checked off the teams I had bet on. By Friday dad, Mr Thomas and Mr Johnson were grumpy and growling at everything. I had managed to speak to Sofia and Cara, both were fourteen. Sofia was half Spanish, she had short red hair with green eyes. Cara was half Irish and had golden blond hair with soft blue eyes.
When I told them about the bet they had been pissed, at least it was directed at their fathers. I slipped into the kitchen where mom was making dinner. I sat and thought about how to ask her if dad had told her about our bet. Mom glanced back a couple of times before turning, “What’s wrong Ryan?”
I blushed, “did dad tell you about the bet we made?”
She glanced towards the other room where dad, Mr Thomas and Mr Johnson were yelling at the TV, “What bet?”
I was tempted to shut up as my face heated up even more, “He had me put up five hundred and he bet... you.”
Mom blinked before narrowing her eyes, “Me?”
I looked down, “I wouldn’t bet for money and... well...”
I glanced at her and sighed, “dad knows I think you are super hot.”
She smiled and then grinned, “So he found something you really wanted.”
I blushed even more, “Yeah, I had to pick a team from every game through Sunday.”
I looked towards the doorway as dad yelled again, “So far I have won all the games.”
She laughed as she turned back to the dinner she was making, “I’ll cheer your teams on.”
I grinned, “Mr Thomas and Mr Johnson put up their daughters too.”
She laughed again as she looked at me, “and you think you can service the three of us?”
I shrugged, “At least I won’t be at the cabin alone.”
She smiled as she went back to making dinner. After dinner mom slipped out as I went to pack. I was going to spend a couple of nights with a friend. Mom was supposed to take me up to the summer cabin on Monday which meant I had to be home Sunday night. I waited until after eating dinner before coming home. There was only one game left and it wouldn’t end until late.
Mom grinned when I slipped in the back door, “trying to avoid your father?”
I smiled, “I don’t think he is going to be happy to see me.”
She came to kiss my cheek before walking back to my room with me. I started packing my small trunk and she cleared her throat, “What happens if I or one of the girls refuse to go along with the bet?”
I grinned, “Than they will each owe me five grand.”
Mom blinked and then laughed, “they won’t pay that.”
I shrugged, “Than I tell everyone they welched on a bet.”
She grinned, “They won’t like that either.”
I glanced up, “think dad will be mad?”
Mom came closer and caressed my cheek, “leave room in the trunk for my stuff.”
I looked at her quickly but she turned and walked out. It didn’t take long to finish packing and I did leave room for mom. I woke when dad started shouting and then I heard mom. I heard them arguing and then dad pulled my door open. I sat up and he glared at me before turning and walking away. Mom walked in wearing a sheer night gown with her arms full of clothes.
I slipped out of bed and took the clothes from her before turning to the open trunk. I split the clothes and carefully put them in the trunk. I straightened and turned to see her in my bed. I hesitated before climbing back under the covers, “what about dad?”
She snuggled against me, “maybe this is the lesson for him.”
I tentatively reached out to cup one of her breasts and she sighed and covered my hand before moving it down. She pushed my hand under the night gown so I was touching her skin and then she moved my hand until it was cupping her breast again. I shuddered at the feel of a real woman’s breast and started feeling and rubbing her nipples.
It was a moment before mom shuddered and moaned. I grinned and caressed down her body to her pelvis. She shifted and opened her legs as I began feeling her pussy. She shivered when I slipped a finger into her pussy and through her slit. I slowly fingered her and slipped my middle finger into her.
I rubbed her clit with the palm of my hand as I started finger fucking her. She was lifting her hips and pressing against my hand as she kept shuddering and shaking. Her warm, velvety pussy was constantly squeezing my finger and mom finally pulled on me. I moved over and settled between her legs as she pushed my pajama bottoms down.
She guided my cock to her pussy and pulled on me as I thrust into her. It was amazing and I shuddered and moaned as I kept thrusting into her deeper. When I hit her cervix, mom jerked and gasped, “fuck!”
I kissed her as I pulled back and started to fuck her. I went slowly because I wanted the feeling to last. Her hips lifted to meet mine when I thrust back into her and her pussy tightened to squeeze my cock. She shuddered and hugged me as I pulled back again. It was a few minutes before I pushed harder and mom jerked hard as my cock opened her cervix.
I grunted and held her as I felt myself suddenly cumming. I shuddered and jabbed as I began to spew a huge, gushing torrent of cum. Mom tilted her hips as she convulsed and wailed, “CUMMING!”
I pumped spurt after spurt as I held her and flooded her. When I stopped cumming she was shuddering and twitching as she moaned. I humped and started fucking her again and she shook me and laughed. I grinned sheepishly and she pulled my face down to kiss me, “Save some for Sofia and Cara.”
I looked at her, “Do you really think they’ll do it?”
She wrapped her legs around me, “I told their mothers about the bet and we all talked, the girls are eager and horny. Tomorrow morning we are going to the cabin. I can stay for two weeks before I have to come back for work but the girls are planning to keep your balls drained.”
I grinned and kissed her, “You’re coming back on the weekends though right?”
Mom smiled as her pussy squeezed my throbbing cock, “we agreed, I get you to myself on the weekends.”
I couldn’t help it and started to fucked her again. She shuddered as she thrust up, “okay, one more time baby.”
I grinned as I kissed her and started to fuck her slimy pussy with long thrusts. Mom shuddered and her pussy squeezed my cock each time I pushed into her. A couple of minutes later she started convulsing as she wailed. I buried my cock and humped against her as she hugged me tight and kept shaking.
I finally pulled almost out of her before fucking her hard and deep. She lifted and spread her legs as she howled and jerked. She kissed me hard as I kept fucking her and thrust up to meet my cock. By the time I was ready to cum she was bucking and shaking violently. I thrust into her and held her as I grunted and began to spew another huge torrent of cum.
She jerked as her pussy gripped my cock. I pumped large spurts into her over and over until I was finished. I sighed as mom dropped her legs to the bed. Sofia and Cara giggled from the door, “That was amazing Jade.”
Mom blushed and then grinned as she hugged me and looked past my shoulder, “it sure felt amazing. You girls are early.”
They came in and Cara cleared her throat, “Our dads are pissed. Mom sent me over, she told dad he wasn’t losing five thousand dollars.”
Sofia laughed, “Mom told my dad that I’m a horny bitch and Ryan can fuck it out of me.”
Mom laughed and I grinned as I pulled out of her, “more like into you.”
They were both staring at my hard cummy cock and mom grinned as she slipped out of bed, “Since you are here we can leave now instead of waiting.”
I didn’t even see dad as I loaded mom’s car. She did go into her bedroom though so she may have talked to him. Sofia and Cara pushed me towards the front seat as they opened the back door and mom grinned as she slid in behind the wheel. It was only an hour’s drive up to the cabin but when I looked into the back the girls were asleep.
When mom stopped beside the cabin I let the girls sleep as I carried everything in. She helped me roll out the sleeping bags and zip them together. I set the three pillows I had brought down and mom smiled as she folded one corner of the sleeping bag back, “Okay Ryan, go bring the girls in.”
I grinned as I went out and opened the back door. I lifted Sofia in my arms and she opened her eyes and leaned against me. I carried her into the house and set her on the bed before going out for Cara. She was like Sofia and only opened her eyes to see me before relaxing against me. When I set her on the bed Sofia was already naked and in the sleeping bag.
Mom was naked as she reached for Cara, “Make sure everything is locked up and come to bed Ryan.”
I went out to lock the door and came back to see all three of them waiting in the bag. I shut the light off as I undressed and set my clothes on my trunk. I slipped into the sleeping bag and Sofia pulled me against her, “Fuck us in the morning Ryan.”
I grinned and cupped one of her breasts before giving her a kiss. I spooned behind her and she reached between her legs to straighten my cock under her pussy. I shivered and held her as I caressed her hip. It was a long time before I fell asleep, I woke to mom slipping out of bed. There was bright light coming in the window so it wasn’t early morning.
I looked at Sofia as my cock hardened under her warm pussy. I moved and gently laid her on her back. I moved down in the sleeping bag and pushed her legs open. I leaned in close and licked through her pussy and she shivered before I felt her hands in my hair. I kept licking her and started using my tongue on her clit.
She began to shudder and jerk as I used my lips and nibbled. A moment later she stiffened and then twisted as she pushed my face away. I moved up and kissed her, “How was that?”
She grinned and put her arms around me, “Good.”
I lifted up and reached between us to guide my cock to her pussy. She lifted her hips, “Go slow Ryan, I haven’t done this before.”
I looked at her quickly, “Do you still have your cherry?”
She smiled and shook her head, “I broke it riding a bike.”
I nodded and slowly started forcing my cock into her very tight pussy. She groaned as her pussy was stretched open and lifted her hips to help me push into her deeper. I started to fuck her slowly and she began to lift her hips. Cara reached out to rub my back, “Do me next.”
I grinned and kissed Sofia as she panted and shuddered. It was a few minutes before she gasped and stiffened and then started bucking and struggling as I kept fucking her. She clutched me as she wailed and her pussy spasmed around my cock, “aaaahhhhh!”
She thrust up wildly and continued to thrash around as I began fucking her harder with deep thrusts. A couple of minutes and she was incoherent as I shoved into her and grunted. I held her tight as I began to spew huge, gushing spurts of cum. She screamed and tilted her hips as warm cum erupted and spewed through her cervix.
I pressed against and into her hard as I pumped spurt after spurt. When I stopped cumming mom chuckled from the door. Sofia dropped to the bed with a big sigh and Cara grinned. I kissed Sofia before pulling out and moving over to kiss Cara. I slipped down her body and pushed her legs open before starting to lick her pussy.
She shivered and spread her leg more and lifted her hips. I pushed my tongue into her and looked up her body, “You don’t have your hymen.”
She grinned, “Mom broke it so I could use tampons.”
I grinned and sucked on her clit before using my tongue to tease it. It took a few minutes before Cara started shuddering and jerking. She finally twisted and pushed my face away. I grinned and moved up as I pushed her onto her back. Sofia giggled and rolled out of bed before walking out.
I pushed into Cara and held her as I slowly forced my cock deeper into her extremely tight pussy. She groaned as her pussy squeezed my cock and I began to fuck her. It took a minute to get all the way into her. I kept kissing her as I slowly jabbed and humped while grinding against her. It was a few minutes before Cara wailed and began bucking and thrashing around.
She squirted and lifted her legs into the air as her pussy contracted around my cock, “RYAN!”
She jerked and convulsing as I began to fuck her with deep thrusts. After another couple of minutes I fucked her hard for a minute and then buried my cock. I humped and pressed into her as she howled and squirmed around under me. I kept kissing her as she hugged me and kicked in the air. It was more then fifteen minutes before I needed to cum.
I thrust into her at the last second and held her as my cock jerked and began spewing a stream of cum into her. Cara screamed when she felt the surge of warm sperm pumping into her, “yyyeeeessssss!”
I kissed her as I kept spurting and pumping cum and she sighed and slowly relaxed. When I was done I pulled out slowly and laid beside her to caress her, “thanks Cara.”
She grinned and turned to kiss me quickly before rolling away, “gotta pee!”
She ran out as I grinned and climbed out of bed. I opened the trunk and grabbed a tee shirt and my swim suit. Mom and Sofia were in the kitchen when I came in. Mom walked to me and kissed me passionately, “we’re going to stay naked so we can get an all over tan.”
I grinned as I caressed her hips, “I’ll put lotion in you later.”
She grinned as Sofia giggled and I let her go, “I need to get the gas tanks out and the canoe.”
We spent the morning setting the cabin up and then we took a canoe ride. By the time we came back they were whispering and grinning at me. I pulled the canoe up on the shore and turned as mom walked to me and pushed me down in the grass. Sofie and Cara helped her pull my shirt off and then my swim trunks. Mom kissed me as she laid on me and then sat up.
She lifted and reached down to position my cock. She slowly impaled her warm pussy before putting her hands on my chest and starting to thrust back and forth as she looked at Sofia and Cara, “Start slow and roll your hips.”
She looked at me with a smile, “you can also use your muscles to tighten your pussy and squeeze his cock.”
I groaned as her pussy grasped and milked my cock and let her keep telling the girls what to do as I reached up to feel her breasts and rub her nipples. It was a few minutes before mom began shuddering and jerking as she became erratic. Sofia grinned, “and Jade has left the building.”
Cara laughed as mom started to convulse and howl. Her pussy spasmed and rippled around my cock as she wet me. I pulled her down and rolled over before I started to fuck her with deep thrusts. She lifted her legs into the air as my cock started pushing her cervix open. She was thrashing around and bucked as her pussy milked my cock.
I lasted another few minutes before burying my cock and kissing her. She clutched me as I started gushing cum into her, “oooohhhh!”
I spewed and pumped and spurted until I was done and mom was more than full. I kissed her again as she panted and slowly pulled out. I grinned and helped her up and she blushed as she looked at the girls before grinning, “Ryan is a stud so I better get used to that.”
Sofia and Cara laughed and took her hands as we walked back to the cabin. Mom seemed like a different woman when she left two weeks later. Sofia and Cara weren’t acting like girls anymore, they acted kind of like mom. We had a lot of fun, holding hands as we waded along the shore or swimming in the lake. Each morning they showed me their birth control before taking it.
That was something mom started. I fucked Sofia and Cara a dozen or more times a day until mom returned Friday afternoon. We wadded in the lake and swam before getting dressed. She was tightlipped as she drove us down to a store. While we were checking out I had a feeling and asked mom to buy a lottery ticket and told her what numbers to pick.
When we returned to the cabin they stripped while I started making dinner and pushed mom towards the front room. She actually smiled as she went to sit with the girls. She had told me their parents were coming up tomorrow morning. We were eating when mom told me dad had filed for a divorce.
I didn’t know what to say and just held her hand. The girls cleaned up as I pulled mom outside to the wide hammock I had made. I held her against me as she caressed my chest. I finally pulled her into the house and to bed. I undressed and just laid beside her to hold her. Sofia and Cara snuggled against us a little later and I relaxed.
It was a long time before I fell asleep because I was worried about what was happening. Mom and the girls were up early and put on bikinis so when Cara and Sofia’s parents arrived they didn’t say anything. Their dads didn’t really speak to me for a couple of hours. When they did they seemed hesitant and I realized they had changed.
After they left that night I used my laptop to check my e-mail and went on the lottery site. Mom sat beside me and kissed my cheek as she leaned against me. As they began to read off the numbers she started looking at me. I had picked the numbers and they were calling them. Her scream and yell after the fourth one brought Cara and Sofia.
They were almost bouncing and mom was in my lap as they read off the rest. This was one of the biggest lotteries in the state’s history. When they read off the last number mom was screaming as she pulled me up and danced around. I grinned and reached out to pull her bikini off, “you are getting so fucked before you have to go back.”
Mom grinned and started helping me, “I’m only going back to quit and tell your dad to suck his own cock.”
Cara and Sofia laughed as they helped mom undress me and pull me back to the bedroom. I pushed her down on the bed and moved between her legs to kiss her before sliding down. She laughed and lay back as I started to lick her pussy and tease her clit. Sofia and Cara giggled as they lay on each side of mom and started sucking on her nipples.
It was a couple of minutes before she was shuddering as her hips lifted and a couple more before she began to wail and spasm. I finally moved up and kissed her as the girls moved and then I pushed into her slowly. I kept kissing her as I began to fuck her slowly with long strokes that pushed my cock against the back of her pussy.
Mom jerked and a minute later howled as her pussy milked my cock. She bucked and thrashed as she clung to me and I kept kissing her passionately. I buried my cock and started to hump, press and grind. She arched her back and screamed as her pussy contracted around my cock, “RYAN!”
Sofia and Cara laughed and Cara rubbed my back, “did you miss it Jade?”
Mom wiggled and jerked as I went back to fucking her with deep thrusts, “YES!”
It was ten minutes before I shoved into her as she squirmed and twitched erratically. I kissed her as I peed a gushing stream of cum into her and she lifted her legs into the air. I spewed and pumped ten huge thick spurts of cum before stopping and mom shuddered hard and dropped to the bed. I kissed her, “I still have tonight and tomorrow to fuck you.”
She grinned as Cara and Sofia snickered and hugged me, “that sounds good baby.”
I fucked mom until way past midnight and she fell asleep on me. Sofia kissed me awake in the morning and whispered, “we’ll fix breakfast, you take Jade to the bathroom for a shower.”
I smiled and pulled her back for a kiss and looked at Cara, “thank you.”
They slipped off the bed and I looked at mom and shook her, “morning sexy lady.”
Mom lifted her head to look at me, “again?”
I grinned, “after breakfast. Sofia and Cara are making it and said to wash you.”
She smiled and kissed me before sliding out of bed, “that was nice, I’m really cummy.”
As I washed her in the shower mom told me dad had filed for divorce the day we left for the cabin. I grinned and held her hips, “how long before it is final?”
She stroked my cock, “I already signed it so probably Monday.”
I tilted her head to look at her, “good, he can’t try to get the money.”
She smiled, “there is that.”
I rubbed her nipples to make her shudder, “go back tomorrow morning instead of tonight.”
She grinned, “you want to fuck me all night again.”
I fingered her pussy and she spread her legs, “did dad let you have custody of me?”
She shuddered and leaned against me, “yes.”
I lifted her and she wrapped her legs around me as I lowered her and impaled her on my cock. I turned to put her against the wall as I began to fuck her and shut the water off to save the hot water. Mom grunted and moaned as she hugged me and her pussy squeezed and milked my cock. It wasn’t long before she was wailing and howling as my cock pressed into her as far as it could go.
It was only five minutes before I grunted and held her as her pussy tightened and I began to pee a fountain of cum up into her. Mom jerked and screamed as she shuddered hard, “RYAN!”
I kissed her passionately as I pumped and spurted. When I was done I sighed and held her for another couple of minutes before I lifted her off my cock. We finished showering and I dried her off before we went to join the girls.
Mom’s divorce was final that next week. We went home with mom and dad tried to play the better man but I smiled as mom glared, “want to bet mom lets me get her pregnant this summer?”
He shut up and looked at mom before turning to leave. Mom grinned and then laughed before pulling me close, “you are in for a long night honey.”
Cara and Sofia laughed before helping mom pack everything. We ended up spending the night in a hotel as mom claimed the lottery. We spent the whole summer at the cabin and mom did get pregnant, twice so far. Sofia and Cara waited until their last year in high school before getting pregnant.
Mom got the cabin and the house in the divorce and the girls live with us. Their parents spent a lot more time with us to and their dads even laughed about losing their daughter to me in a bet.