Maddy gets sent to her Uncle's farm for the summer. She had no idea what was in store for her there.
Maddy was pissed she was being sent to her Uncle’s for the summer. He lived out in the country in the middle of nowhere. The cell reception was terrible, they didn’t have internet, and the house itself was over a hundred years old. All her friends were spending the summer between high school and college traveling to cool places, meanwhile she would be lucky if the town had a public library. On the day of her departure she reluctantly got into her Uncle’s pickup and waved goodbye to her parents.
The drive felt like it took forever. The first half hour Uncle Doug talked up all the fun stuff she’d be able to do, like hiking and swimming in the creak, and County dances. But with Maddy acting uninterested Doug eventually stopped talking. Maddy dreaded the very thought. She had hoped that at the very least she’d have been home this summer so her and her boyfriend could finally find a time to do it. Maddy and Rob had dated all senior year, but things just hadn’t lined up and now it was summer and she was still a virgin. She hadn’t even seen Rob’s dick, just felt it a bunch through his jeans. As Maddy thought more and more about Rob fucking her she realized her panties where getting wet. She pushed the bad thoughts out, just like her mother taught her, and focused on the scenery.
They pulled up to the house and Maddy realized this was her reality for the next three months. She gulped and they unpacked the car and Doug called for his son. It was hard to believe Bliss was Doug’s son. They were both over six feet but Bliss was rail thin whereas Doug had a much heavier build. Maddy absentmindedly thought that Bliss was looking a lot cuter than she remembered. As soon as that had popped into her mind she pushed it out.
She got settled in and the first week was pretty uneventful. She went on short walks every day and then would either read or try to chat with her friends through the bad reception. Bliss and Doug worked during the day so Maddy didn’t see much of them except at dinner. When her first Saturday rolled around Maddy was woken up by a knock on her door. “Hey cuz, I don’t think you’ve been to the swimming hole yet, I was thinking it’d be a great day for it.”
Maddy figured there was nothing else to do, so might as well swim. Maddy got out of bed and found her swimsuit. She hated the two suits she had brought but they were all she really had. Her body type was not great for a two piece but she looked much worse in a one piece. Maddy looked in the mirror as she pulled on her swimsuit bottom. The high waist helped hide her chubby belly, but her ass poured out the back. The top was a lot cuter and supported her E breast perfectly, but at the end of the day she still felt like a pig. Maybe this summer would be the one where she’d lose weight. She shrugged and finished getting dressed.
Bliss was waiting for her at the bottom of the stairs with a backpack on. “I made a couple sandwiches and have water and stuff for lunch.” He beamed at her with his big goofy smile.
Maddy thought again about how cute he was and wondered what he thought of her. She wondered if he’d like her top showing off her juicy tits. Maddy pushed that back down, she couldn’t have any of those thoughts.
The swimming hole was much farther away than Maddy had thought, but after an hour of hiking Bliss finally announced they were there. It was a really cute meadow that had a decent sized pond on one side. Bliss quickly dropped his pack, stripped down to his boxers and ran into the water.
Maddy took her time and walked to the water’s edge. Bliss was about fifteen feet away treading water. Maddy called out, “How is it? It looks really cold.”
Bliss smiled at her again, “It is really cold, but it’s the best ever. Come on in, or do I have to make you.”
Maddy could feel herself getting horny at the thought of Bliss forcing her to do anything. She’d love to have him manhandle her a little. Rob had always been so gentle and worried so much about hurting her, Bliss on the other hand seemed to know how to push limits. Maddy barely noticed Bliss get out of the water and cried out as he grabbed her, “What the fuck, you asshole!” She was laughing as she yelled though and didn’t resist as Bliss picked her up and carried her into the water, unceremoniously throwing her the last bit.
The water was freezing cold and as soon as Maddy had resurfaced she charged up to bliss and started splashing him. The two of them rough-housed a bit in the water until Maddy was tired and got out. She spread out a towel and started to dry off. Nobody had ever been that forceful with her, and she absolutely loved it. She couldn’t push down the thoughts any more, she wanted Bliss. When Bliss finally got out of the water he laid a towel down next to Maddy’s and started routing through the bag. He produced a bottle of water and then a jar of shine. Opening the shine he took a small sip and offered it to Maddy. She politely refused.
They sat there talking for a bit before they got on the topic of relationships. Bliss wasn’t too serious, and was doing whatever felt right. Maddy explained her situation with Rob. Bliss pushed to hear about the physical side and could hardly believe how little was there, “You mean you haven’t seen his dick yet? Not even a picture?”
Maddy blushed, “No, he wasn’t into that stuff and the timing was never right.”
Bliss laughed and took another swig of his shine. He then stood up and dropped his boxers. Maddy stared intently at his cock. “See, that’s all there is to it. Don’t know what took him so long.” Maddy looked away. Bliss pulled his boxers back up, “I mean fair is fair, even though this Rob guy is too chicken I’m going to. I showed you mine, how about you show me yours?”
Maddy looked at him in disbelief, “You think I’m going to show you anything just because you whipped your dick out?” Maddy was surprised though that she was trying to figure out a way to show him something but still save face.
Bliss grabbed her by the hands and helped her to her feet, “Come on, at least let me see those tits. I mean god damn they look beautiful.”
Maddy feigned reluctance and she lifted her swimsuit top off, “There, are you happy now?” Maddy felt so free, and so horny. She’d never shown a guy her breast but here she was, standing in a meadow showing her handsome cousin the goods.
Bliss stared intently, “Fucking A, those are outstanding, I don’t get how they can be that big but still be perky.” Bliss had stepped forward and reached out his hands. As he grabbed her fat tits, Maddy felt electricity course through her body. She didn’t move as Bliss kneaded her Es and began sucking on her nipples. She couldn’t help herself and let out a quiet moan. She could feel the juices rushing to her pussy.
Bliss took a step back and dropped his boxers again. His cock was now fully erect standing at a healthy seven inches, and Maddy was relieved to see it was kinda narrow. Maddy felt like she was in a dream as she grabbed the high waist of her swimsuit bottom and exposed herself to her cousin. Bliss took in his chubby eighteen year old cousin. He’d fucked his fair share a girls, but he always loved how hard the slightly ugly or fat ones tried. Bliss helped Maddy down onto the towels. He got on top of her and started kissing her aggressively. He held himself up with one arm but grabbed the back of Maddy’s head with his free hand. Maddy had trouble processing all the feelings coursing through her. Bliss’s body was so warm and muscular, and the way he gripped her head made her feel like she was the only thing in the world. At the same time the way he forced his tongue into her mouth reminded her that he was looking for much more.
Bliss adjusted himself so one of his lean thighs was right against Maddy’s clit. By rotating his hips he began dry humping his cousin with more precision and control than she’d ever felt. She couldn’t imagine getting off through a pair of jeans, but this was so intimate she felt an orgasm building within her. If Bliss hadn’t been paying attention he’d have missed the silent cry from his cousin and her going limp.
He pulled off her mouth and smiled at her, “Little better than rubbing a cock through his jeans?”
Maddy could only whimper in response. Bliss took her silence to mean that he was free to proceed. He moved between her legs and told her to grab her knees. She did as she was told and quivered in anticipation. Bliss rubbed her juices around her hairy cunt until he was pretty sure she was ready. His head pressed against her hole and slowly he drove into her. He’d only gotten his head into her when she cried out, “ow, this hurts, please, it really hurts.”
Bliss paused, “I’m sorry, but there is no real way around that unless you want to stretch yourself on your own.”
Maddy felt Bliss’ pulse through is penis and even though it had hurt she knew that was part of losing your virginity. She nodded.
Bliss wanted to be crystal clear, “Can you say it? Just so I know I’m not violating you?” Bliss loved this power play. He’d used some form of it on several chicks in the past. Make them beg for it.
Maddy couldn’t find the words so she shut her eyes tight and blurted out, “Please fuck me, no matter how bad it hurts or what I say.” Her eyes were still shut when she felt him pull out a little and push back in. There were multiple sources of pain that Maddy had trouble placing. Her vaginal walls felt like they were being ripped apart, and then there was another more dull pain from what she could only guess was her hymen. She cried out again.
Bliss couldn’t believe how tight his cousin was. It was like fucking a girl’s ass when she suddenly decided she didn’t want to. There was plenty of fluid in her and his cock slid in and out with ease, but the pressure was mind blowing. By the time he’d bottomed out in her he was ready to burst. He stopped thrusting and instead ground his pelvis into hers. This change had it’s desired effect and soon Maddy opened her eyes and let out a moan. He concentrated hard on not cumming just yet and continued his movement until Maddy started to hyperventilate. Unlike her last one, this orgasm was loud and obvious. Bliss gave her three quick pumps and released in her.
He rolled over and collapsed on the ground, “Holy shit, you have the tightest pussy ever. I just, I just don’t even know.” He was shocked at how great she felt. He’d never have guessed it, normally big girls like her had big old pussys.
Maddy was still recovering from her orgasm as she felt cum running out of her tiny sore hole. She shook again, accidentally squeezing and forcing the rest out. She felt the warm fluid run down her asscrack and pool on the towel.
After that first fuck, the next two weeks were a blur for Maddy. Every chance she got she was sneaking off with Bliss to get fucked. She was relieved that her pussy loosened up a bit and although it was still like a vice grip for Bliss she wasn’t in as much pain. Maddy was incredibly disappointed when she heard that bliss was going to be going out of town for a week to go hunting with the guys. She figured she could masturabte or something but it wouldn’t be the same. Bliss left on a Saturday morning, and by lunch time Maddy was feeling horny again.
She decided she’d grab a snack and then go to the barn to “read”. In the kitchen she bumped into her Uncle. He was quieter than normal but Maddy was on a mission. As she was leaving Doug finally spoke up, “I know what you and the boy have been up to. You dumb kids think you’re so smart. I have half the mind to punish you for acting like I’m blind.”
Maddy’s heart had stopped, if Doug knew, he might tell her Mom. Maddy felt like her best bet was to play dumb, “What are you talking about?”
Doug got up and grabbed Maddy by the arm, he gripped her hard enough to hurt. Maddy was frightened but oddly aroused. Before she knew what was happening Doug had brought her over to a chair, sat down, and pulled her across his lap. Maddy screamed, “What the hell are you doing! You can’t do this!”
Doug ignored her, lifting up the back of her sundress. “Little whores like you need to be taught a lesson sooner or later. Just like that mother of yours.” He aggressively pulled down her panties, ripping the cheap fabric. Before the first slap landed Maddy was already crying. The pain shot through her body, but the burning sensation stayed longer. Ten slaps in Maddy’s ass was cherry red, and although she’d been crying the whole time, she was ashamed to admit her juices were flowing.
Doug took a break and grabbed Maddy by the hair, pulling her head back, “You ready to admit what you’ve been doing?”
Maddy sobbed as she choked out, “Bliss has been fucking me, he took my virginity by the swimming hole, I’ve let him fuck me every chance we get.”
Doug released her hair and lowered his hand back down to her ass. He slowly caressed her sore cheeks and then ran a finger down her crack, gently pushing on her asshole before moving on to her dripping wet pussy. “Well look at this, you were a virgin a month ago and now you’re creaming over getting beat.” Doug got her off his lap but didn’t let go of her. Without saying a word he bent her over the kitchen table and lifted her dress again.
Maddy didn’t resist. She eventually felt her Uncle’s cock press against her hungry lips. As he pushed in, Maddy was hit with a panic. She hadn’t seen his cock but it felt like it was already tearing into her and he’d barely even started. She cried out in pain as Doug tried harder. “God damn, I’ll be. Tightest pussy I’ve ever seen.”
Maddy was a little disappointed that she wasn’t going to get fucked but knew her Uncle’s cock would have broken her. Doug cleared his throat, “well now I don’t want to rip my little niece apart, but you need to learn your lesson. Come over here and get on your knees.”
Maddy complied and was looking down at her Uncle's thick girth. It had to be about the same length as Bliss’ but it was easily as wide as Maddy’s wrist. “Well what are you waiting for you little tart?”
Maddy hadn’t sucked a dick before and tried her best. The head of his cock would fit in her mouth and when she tried that she got smacked across the head, “No teeth you bitch.”
Maddy decided on licking and jerking and hoping that’d be enough. It took her a whopping twenty five minutes before she could feel her Uncle was about to cum. Maddy had never tasted cum before but the precum she’d just licked from his dick wasn’t too bad so she decided to go for it. She locked lips with the tip of his penis, tonging him slightly, while she gripped his base and jerked his shaft. She didn’t mind the taste, but the quantity shook her. He must have been saving that load for a while. Two gulps later Maddy thought her embarrassing nightmare was done.
Maddy got up and was about to exit the room when Doug piped back up, “Where do you think you’re going? Go under the sink and grab the shortening. Also the turkey baster from the drawer.”
Maddy hesitated but complied. Returning the objects to her Uncle. “Now bend over that table again, lift your dress and spread your legs.”
Maddy did as she was told. She had an idea where this was going but didn’t fully understand. “You’re not the first woman who couldn’t handle my cock. It’d be a shame to ruin your pussy by stretching it out, and there’s nothing I can do about your mouth.” Maddy felt the oily substance spread over her puckered ass hole. “Your cute little rectum though, that can be stretched out a whole lot and nobody would mind. Hell, your mom once got piss drunk at Christmas and showed us all what she could do with a wine bottle.” Doug chuckled to himself as he thought of his sister, to bad the dumb girl stopped drinking and got herself married.
Maddy had trouble believing what she heard, her mom had been sober for ages, maybe it was back when she was much younger. She focused on these thoughts to distract from the feeling of a greased up finger sliding into the virgin asshole. She’d never imagined she’d let somebody do this to her. It wasn’t as bad as she had thought though, and as she relaxed she found it oddly enjoyable. She kept feeling like she needed to shit but that was oddly soothing.
The second finger changed things. Maddy tensed up and couldn’t relax. It felt like when her pussy was overfilled. Eventually Doug pulled his hand away. “Ok girl, get up on the table facing me.” Maddy awkwardly sat on the table and positioned herself on the edge. Doug pulled a chair up. “Damn, we’re going to have to do something about this hair, can’t be choking on fur balls. Go ahead and spread your lips for me.”
If Maddy could still feel embarrassment she’d be crushed right now, but since the spanking she just didn’t have any real fight left in her. She learned she got off from pain, and humiliation, what more was there to be embarrassed about. She reached down and pulled each lip apart with her hands. Her uncle didn’t waste time and drove his finger back up her asshole. It went in surprisingly easily. As he pumped his finger in and out of her he also began licking her clit.
Bliss hadn’t gone down on her, he’d just fucked her wet pussy, so this was a new mind blowing sensation. With everything that had happened this afternoon she was soon cumming against her Uncle’s tongue. She didn’t even notice that there was a second finger in her ass. “Now this is a trick I learned with your Aunt.” Maddy felt the fingers pop out and the greased up end of the baster enter her. The measuring marks were surprisingly pleasurable and although the baster was larger than two fingers it slid in easily enough. Soon only the rubber bulb was sticking out of her.
Doug leaned back and Maddy released her lips. She felt full and like she needed to poo. “Some new house rules while I train you. Today it's the baster, who knows what it’ll be tomorrow, but whatever I put up your ass stays there. If you need to shit let me know and I’ll supervise. To make it easy for me to check you can’t wear clothes inside. In fact, strip down right now.”
Maddy removed her dress and bra, dropping them to the floor next to her tattered panties. It felt weird having something so big in her, but she felt hot all over. She knew when Bliss came back. She’d have him fuck her ass. Doug got up and put the shortening on the counter, “The other rule is that until I can fuck that ass of yours, every morning you’re going to be down here at eight sharp to give me a blowjob and to receive your slaps.”
Maddy nodded and scurried out of the room. As soon as she was in her bedroom she thought about removing the baster. Although she was a little excited about the punishment she knew he could tear her holes apart if he wanted, and she knew she’d obediently let him do it.
When she was ready for bed she went to her Uncle's room and knocked on the door. She heard some shuffling as he came to the door. Before he could say anything Maddy blurted out, “Can I pump the baster in and out if I’m masturbating?” She was staring intently at her feet.
Her Uncle smiled, “I’ll allow it.” Maddy hesitated before leaning up and kissing her Uncle’s cheek and leaving for her room.
The next morning Maddy was on her knees at eight sharp. Doug let her suck him dry, and Maddy noticed although he still had a huge load it was much smaller. After that she bent over his lap. He removed the baster and watched as her hole slowly closed back up. He enjoyed the ten hard slaps. She relished the feelings swelling in her pussy with each impact. After the last slap she waited for Doug to reinsert the baster. “Get off me, we’re going to the garden.”
Maddy knew they didn’t have any neighbors but it still felt weird walking outside. They walked around to the back of the house to the raised gardening beds. Doug pointed to the cucumbers, “Pick out your next trainer, if it’s too small then I’m going to pick one and give you a severe punishment.”
Maddy looked around, there were several that were the same size or smaller than the baster but she knew those were off limits. The more she looked the more she realized none of them were that much bigger, and if she’d already gotten used to the baster why not go big. She found a big one that was probably two inches in diameter and a foot long. What excited her about this was that it was covered in these little bumps. Doug approved the choice and they returned to the kitchen. Maddy got right to the edge of the table and held her lips open.
It was much slower going this time but two orgasms and thirty minutes later the cucumber was all the way in. Maddy hurried to the bathroom to get her toothbrush, she didn’t close the door as she closed the toilet seat and squeezed the cucumber out and bit, she turned on the toothbrush and sat, pushing the cucumber back up. With her toothbrush on her clit and the cucumber pumping in and out of her, she was in heaven.
The next two days were similar except that Doug was at work all day and Maddy masturbated to her heart's content. She was sure to not violate the rules even though her Uncle was away. That Tuesday night once dinner was cleaned up, she got up the courage, “Uncle, can you please fuck me up my ass?”
Doug knew she was probably ready, and was planning on fucking her in the morning, but he couldn’t say no to her.
“Give me your cucumber and go up and grab that toothbrush of yours.” In a moment Maddy was back. Doug bent her over the table and turned on the toothbrush. It took some adjusting but soon it was under her, gently massaging her clit. The first slap caught Maddy off guard and she cried out. The next nine were what she’d come to accept. Within moments of the pain from the last slap dissipating she felt the large warm member pressing against her rosebud.
There wasn’t as much sensation as she would have liked, but between the toothbrush and the understanding that she was finally satisfying her uncle she felt full. She came pretty quickly as he gripped her fat hips and pounded away. With the waves of pleasure gone and the fun but repetitive motion in her ass, Maddy was starting to lose focus. Doug sensed this and released one hand from her hips and grabbed her hair. He pulled hard and lifted her head and chest off the table. Maddy cried out but loved every second of it. During her second orgasm she felt him release. He lowered her head back to the table and sat down. “Well fuck, you’re definitely your mother’s daughter.” He gave her a hard slap.
They didn’t say much the rest of the night but before going to bed Maddy returned to her Uncle’s bedroom. He opened the door and looked at her, she quietly piped up, “Can we talk a little? I can suck your dick while we do it.” Over the last couple days Maddy had been getting her bearings and Doug couldn’t say no. He let her in and laid on the bed, Maddy followed and began licking his dick, after a minute of silence Maddy opened up, “What you said earlier about my mom, can you tell me about her?”
Doug chuckled. This little slut had earned a good story so he laid it out for her. Doug and Maddy’s Mom Melissa, grew up in this house, and they learned a lot about the world from each other. Up until Melissa’s wedding day Doug would still regularly fuck her, but only up the ass. Melissa had a bit of a drinking problem and it got to the point that Doug thought she’d spill the beans or get herself hurt, and so he reluctantly helped his parents and sister get Melissa the help she needed. It was a family effort and it worked, Doug wasn’t really that involved but he’d gotten the ball rolling. Melissa still kept their secret. Doug took the story to the present day, “Your mom called me up a couple months ago about you visiting. I thought it was a weird idea and I made it clear what I thought about female family members and she still pushed for it. I guess she thought it’d be better to learn like she did than from some drunk frat boy in college.
Maddy was stunned but kept sucking. Doug piped up, “I mean damn, when I told her yesterday that it was cucumber season this was her reply.” Doug leaned over and pulled up his phone, after a couple of minutes Maddy was looking at a full body shot of her mother with a cucumber sticking out of her ass, cunt, and mouth. Maddy’s pussy was flush. Doug looked at the picture as Maddy finished him off, swallowing his load.
“Thank you for sharing this, I honestly feel much closer to her now.” Maddy had gotten up when she stopped and turned back to her Uncle. “I have an idea, I’ll be right back.” Maddy rushed to the garden and returned with three cucumbers of her own. She’d picked ones that maxed out each of her holes and had soon stuffed herself. Doug laughed as he took the picture of his niece. Maddy caught him before he hit send, “Wait, send her a video instead,” Maddy ran and grabbed her toothbrush. “Start shooting before I cum.” Maddy put the cucumber back in her mouth, spread her legs, placed the toothbrush on her clit and started to pump the vegetables into her ass and pussy.
When she was done they had a great picture and a two minute long video of her choking on a cucumber while cumming. Doug gladly hit send. Maddy went back to her room and went to bed, thinking of all the fun things she’d do this summer.