Holiday With the Jamesons

Stacy had had a lot of strange sexual experiences by the time she was sixteen. She'd been seeing an older gentleman down the street since she was eleven, and having sex with him regularly since she was thirteen. And she was known to all the boys at school as a perfect hussy, a "sure thing." It seemed like half the freshman class had lost their virginity inside her, and plenty of the older boys, too. And it wasn't just the boys at school; Mr. Robertson, the math teacher, had taken to putting his stubby little dick in her on a regular basis during tutoring sessions after school.

But none of this could really prepare her for what was going to happen during the week she spent at her friend Kelly's cabin in the woods.

Kelly's family was rich. Stacy was dirt poor, although you wouldn't have guessed it by the way she dressed--her older friend down the street loved to give her lots of presents, particularly fancy clothes. But Kelly's family had tons of money, and it showed. They had this incredible "cabin" in the woods, with their own beach and everything, and during the summer between their freshman and sophomore years in high school, Kelly invited Stacy to stay with her for a week.

When Stacy got to their cabin, Kelly took her out to show her around. They went to the beach first, which was pretty much right in front of the house. As they were walking there, Stacy noticed that a boy, probably Kelly's little brother Steve, was down at the beach, taking his shirt off. Stacy had never met Steve, but she knew he was twelve, and from the back, he pretty much looked his age. He was tall, but skinny as heck. As she watched him, she was amazed to see that he simply dropped his pants and underwear and was completely naked.

"Oh, god," she says, "you're brother!"

"Yeah," Kelly says. "Since this is our private beach, we usually don't wear anything when we go swimming. Hey, Steve!" she shouted to him.

Steve turned to look at them. "Hey!" he yelled.

"This is Stacy," Kelly said as they walked up to him.

"Hello, Stacy." Steve extended a hand to shake hers. Stacy was feeling a bit bewildered as she reached out and shook his hand. "Hello," she said, a bit uncertainly. Then Steve just stood there, buck naked, in front of her, just like he was intentionally showing off his pre-teen dick to her. And she couldn't help but stare; he might be a scrawny twelve year old, but he had some pretty impressive meat, a big ol' hairy dick, balls hanging two inches down and a cock that even though he wasn't hard was at least three inches long. He was grinning at her, he knew she was staring, and he loved it.

"Come on, let's swim," he says.

"Um," Stacy says.

"We can go get our swimming suits if you want," Kelly said quickly.

Steve was still grinning at her, and Stacy suddenly decided she wanted to see what the kid looked like with a hard-on.

"No, that's all right," she says. "I'll just take my clothes off."

If there's one thing that Stacy knew how to do, it was strip. She'd been doing it since she was eleven for Chris, her boyfriend, the older guy down the street, and she had no inhibitions at all. So she just stood there right in front of Steve and pulled her shirt off. Then she unhooked her bra and took it off, too. Stacy wasn't exactly what you'd call "stacked," but she had a nice set of breasts and she was well aware that guys liked them plenty. And they had exactly the effect on Steve that she was hoping they would--his dick was already standing up before she'd even got her bra unhooked, and by the time he was staring at her naked tits, he had a full, raging hard-on, five inches at least sticking straight out from his scrawny body.

Kelly, who was undressing as well, started laughing. "Look at that! He's got a boner!"

The grin was completely gone from the kid's face and he was beet red. He reached down with both hands and covered himself up.

"Oh come on, don't be embarrassed," Stacy said. "It's perfectly natural." She gave her tits a little shake, then pulled her pants and panties down. Now it was Steve's turn to stare, and Stacy's turn to grin. He still had his hands down, covering his meat, but Stacy noticed that his fingers were twitching a bit and she knew that what he really wanted to do was start jacking off.

The three of them swam for a while, and Stacy noticed that every time the boy thought the girls weren't looking, he had his hands down in the water and he was beating off. This made her smile, and she would pretend she didn't notice but give him a good look--make sure he could see her breasts really well, even make them shake and shimmy a bit. She was pretty amazed, actually, when she realized after a little while that the kid had every intention of getting himself off, right then and there. Stacy whispered to Kelly, "I think you're brother's about to shoot his rocks off right in the water," and Kelly's like, "Yeah, I'm not surprised, he jacks off constantly." When Kelly was pretty sure he'd got himself to the point where he was ready to blow, she turned and faced him and smiled right at him. His eyes went wide, because he knew he'd been caught, but what could he do? She knew he was coming right then. His face was all red, and she knew he was shooting off.

OK, so that was a little weird, watching Kelly's kid brother beat himself to orgasm right in front of her. But it was nothing compared to what happened that evening. They had settled down for a movie, the kids sitting on the floor with some popcorn, when Kelly's mom walked in the room. Stacy was a bit amazed, because she was wearing a little silk outfit, the shirt was tiny and low-cut, so that it showed off her ample bosom, and the shorts were tight. The whole thing was more or less transparent, and she could see the woman's large nipples fairly clearly, and she could see her pubic hair as well. She walked over to the bar and took out a bottle of coke and some rum.

"You girls want a drink?" she asked.

Stacy raised her eyebrows at Kelly, who gave her a quick grin and said "sure!"

She mixed four drinks, handing two of them to the girls. It was a stiff drink, to be sure. Stacy wasn't very experienced with liquor and it burned as it went down. Kelly's dad walked in the room, and he was wearing silk as well, a robe that he had tied very loosely and a pair of boxers. Stacy thought it very strange that the man would be hanging out in his underwear. The two grown-ups snuggled up on the couch and drank their liquor fairly quickly, and Mrs. Jameson got them two more.

Half-way through the movie, she happened to look over at the grownups sitting on the couch, and she realized that Kelly's mom had her hand down her dad's underwear. She looked away quickly--it took a lot to embarrass Stacy, but this was close. But, she couldn't help but look again, just to make sure she wasn't seeing things, and sure enough, not only did the woman have her hand down his shorts, but she was pretty clearly jacking him, and he had his arm around her and his hand up her shirt, squeezing her big tit. Then Stacy realized that Kelly's mom was looking right at her, that she knew she was watching. The woman gave her a smile, then pulled her hand out and fished her husband's dick out of his fly. She held his shaft up and gave Stacy a grin, just like she was showing off her husband's shit to the girl. He had a surprisingly large cock, even bigger than Chris's, and his balls, which the woman had fished out as well, were hairy and hanging down, looking quite big as well. Kelly's mom leaned over and kissed the tip of his cock, looked back at Stacy and gave her a smile, then took his head in her mouth and started jacking him.

Stacy was definitely embarrassed now, but she couldn't look away. It was fascinating to see another woman's technique. Stacy noticed that the other two kids were paying no attention at all, and she wasn't sure if they weren't aware of what was going on, or if they were just intentionally ignoring it. The woman sure knew what she was doing, and it didn't take long for her to get her husband off. He grunted, rather loudly, and Stacy knew he was coming. Kelly's mom took the whole load in her mouth, squeezing his balls while he shot off. When she pulled away from his dick, she gave Stacy another smile, then opened her mouth and showed the girl her husband's junk. She smiled up at her husband and he handed her his drink and she took a big swig, washing down his come. Then Stacy noticed that he was staring right at her, his big dick still hanging out of his fly, giving her a big smile. Fuck, he knew she was watching, too. He reached down and lifted his whole package and sort of pointed it in her direction, like he was saying, next time is your turn, girl. Then he stuffed it back in his shorts.

The next day, the kids all went for a bike ride, riding over to a nearby town for lunch. Stacy didn't mention to Kelly what happened the night before, she didn't want to embarrass her, although she kind of thought that her reaction might be something more like nonchalance- "Yeah, they do that all the time" or something like that. That would freak Stacy out even more. Steve was being sweet; he was obviously embarrassed by the fact that she'd caught him jacking off, but he also obviously doted on her, looking at her all the time whenever he thought she wouldn't notice, with that longing sort of look that only a virgin boy can have. She had a lot of fun with him, leaning over and letting him look down her shirt and stuff like that.

When they got back to the cabin, the grownups had taken a couple of lawn chairs down to the beach. Kelly's mom was swimming, and her dad was sitting on one of the chairs, wearily a terry-cloth robe, sipping a drink, and reading a newspaper. Kelly's mom saw them and gave them a wave.

"Come on in, kids, you must be really hot!"

Kelly and Steve just took off their clothes and ran into the water, but Stacy hesitated. She could feel the man's eyes on her, she knew he wanted to see her naked. She turned and looked at him, and he was sipping his drink and staring at her.

"Come on, Stacy," he said, fairly quietly, "why don't you go for a swim?"

Oh, what the fuck, she thought. This family is so weird, his wife probably doesn't even care if I strip for him. So she turned to face him, spreading her legs open a bit in a sort of "stripper" pose, and started taking her clothes off. He just sat there, sipping his drink and watching her undress with a little grin. When she was naked, she just stood there in front of him, giving the horny old bastard a good long look. She noticed that he had a big hard-on, his thick purple head sticking out of his robe. He saw her looking, and he opened his robe, showing his whole dick to her. God, he has a big fucking dick. She shook her head at him with a little grin, then turned and ran into the water.

That evening, Kelly's parents went out and Kelly and Stacy were in their room, playing on the computer. Stacy went to the bathroom and she heard a strange noise from downstairs, like a woman moaning or something.

"I think your brother's watching porn," she said to Kelly when she got back to the room. They quietly sneaked downstairs and sure enough, he was sitting in the TV room with a porn video on. They couldn't really see him but they knew he was jacking.

"See, I told you," Kelly said when they went back to her room. "He's always jacking that little dick of his."

"It's not so little," Stacy said.

"Really? I think you like him!"

"No, I'm just saying..."

"Well, he's got a big crush on you, I know that."

"Yeah," Stacy said.

"Hey, I have an idea. I dare you to go in there and give him a handjob! Wouldn't he love that!"

She had to admit, she liked the idea. "OK, I'll do it!"

Kelly had a big grin as they snuck back downstairs and then walked right into the TV room. The poor kid was sitting there with his pants around his ankles and he quick tries to pull them up, but Stacy sits down next to him.

"Don't worry," she says, reaching down and taking his pecker in her hands. "I was just gonna help you out."

"Yeah, Stevie, she's gonna give you a handjob!" Kelly says.

His cock was big and hard and she had a good time massaging it. He watched, wide-eyed in fascination. She stopped right before he was about to blow. "You've got a nice big dick," she says.

"Yeah, she likes your dick, Steve. She told me."

"You want me to make you come?"

All the poor kid could do was just nod his head. Just a few more strokes from her expert hand was all it took, and the boy started to explode, big shots of come firing into the air and landing on the floor.

"Wow," she said, "that was a big load!"

After they went to bed, Stacy waited until she was sure Kelly was asleep, and then slipped out of the room. She walked down the hall to Steve's room and went inside.

"Hey, Steve," she said, waking him up. He looked at her, confused. "I thought maybe we could do more than just a handjob, if you wanted."

"Um, OK," he said, still sounding confused.

She climbed on the bed and slipped her panties off. "Are you a virgin?"

"Y--y--yeah," he said, his voice trembling.

"Do you want to lose your virginity tonight?"

"Y--y--yeah."

She lay down and spread her legs open. "You can fuck me, right now."

He fumbled as he pulled his underwear down, and then she pulled him in towards her.

"Come on, big guy, put it in me." She reached down and directed his cock into her pussy. "Oh," she said sweetly as he slid into her, "you have such a nice cock!"

Stacy loved fucking virgins. For one thing, they get it over with quickly. Steve was no different, he'd barely got the hang of what he was supposed to do when he was obviously about to come.

"Give it to me," she whispered to him, "give it all to me!"

"Oh God!" he said, quite loudly, as he started orgasming. Right then, the door to his bedroom opened, and Stacy was mortified to see Kelly's mom standing there. Steve didn't even notice, he was in heaven, shooting off inside her.

"Well, what do we have here?" Kelly's mom says.

Steve's eyes went wide with terror and he pulled out and rolled off of her, spurts of come still shooting out of his cock.

"You two were having some fun while we were out, weren't you?" the woman said, smiling as Stacy pulled her nightie down. "OK, finish up, kids, and then get to bed. It's late." She pulled the door closed.

The next day the kids were down swimming, Steve was acting really strange, too embarrassed to even let her see his dick when he undressed. She thought that was funny, usually a guy is all high-and-mighty after he's fucked her, like now that he's had his dick in her, he owns her or something. She was glad Steve wasn't like that. So they're swimming around and Kelly's dad comes down to the beach.

"Stacy," he says, discretely enough that the other kids don't hear him, "can I speak with you for a moment?"

She felt pretty self-conscious as she climbed out of the water, naked, the man's hot stare on her body. "Sit down for a sec," he says, gesturing to one of the lawn chairs. He sat down in the chair next to hers. She felt his eyes on her breasts, then he looked up at her face. "Jenny told me what she caught you and Steve doing last night."

Stacy didn't know what to say; "Sorry" didn't seem quite right, so she just sat there.

"Are you using birth control?" he asked.

"Yeah, I'm on the pill."

"And what about STDs? Have you been tested?"

"Yeah."

He put his hand on her knee. "You're a nice girl, Stacy. That was a very nice thing you did for Steve." Stacy was surprised by this reaction, although she knew she probably shouldn't be. Nothing in this family should surprise her. She just looked at the man and smiled. He slid his hand further up her leg. "You know," he says, "Steven is not the only man in this family. You come on up to the house in a couple minutes, and you can be nice to me for a while."

She told the other kids she had to go to the bathroom and went up to the cabin. He was sitting in the living room, reading the paper, and he smiled at her. They went to his bedroom and she lay down on his bed and spread her legs open. He dropped his drawers and knelt between her legs and she saw his huge dick, standing out at least seven or eight inches, before it disappeared inside her. His dick felt huge inside her, it almost hurt, but luckily he was all business, he just wanted to get off inside her as quick as he could. Maybe he was worried that his wife would show up, although he couldn't be too worried, because he left the bedroom door wide open.

He was laying on her, holding her down, working himself up to his orgasm, when Stacy saw Steve standing in the doorway. She smiled at him and gave him a little wave, but he didn't really respond, he just stood and watched. He stood there the whole time, even when his dad grunted as he began to orgasm, watching as the man unloaded into the pussy that he had been enjoying just the night before.

When he finally pulled his big dick out of her, she noticed that Steve was gone. She got out of the bedroom as quickly as she could and went to Steve's room. He was laying on his bed, looking at the ceiling.

"Hi, Steve," she said.

"Hi." He looked at her and she suddenly felt odd, realizing that she was still buck naked.

"Hey, I'm sorry about that. He just..."

"It's OK, I know what my dad's like."

"Look," she says, "you never really got a chance to finish last night. You want to try again? Right now?"

She was wide open and sloppy from the fucking she'd just gotten from his dad, but he didn't seem to care, or even notice. He was just happy to be getting pussy again. He fucked her like he was still a virgin--all he wanted was to come, and that was OK with her. She encouraged him--"Come on, big guy, give me your come! Give it all to me!" It didn't take long, two minutes at the most and the boy started emptying his balls. This time, he got to fire it all into her, and he was obviously very happy about it, grinning ear-to-ear when he pulled out. She went in the bathroom and cleaned up, then ran down to the beach and finished swimming with Kelly.

That night, they played card games and drank more rum and cokes. Kelly's mom kept the drinks flowing freely and the girls were pretty drunk by the time they staggered off to bed. As they turned into Kelly's bedroom, her mom grabbed Stacy by the arm. "Come on with me for a minute," she said with a little smile.

She led Stacy to the master bedroom, where Kelly's dad was sitting in this silk boxers and nothing else. "Mr. Jameson is looking for a good time tonight," the woman said to her, "and I thought you and I could show him one." Stacy was too drunk to really object, and she just followed the woman up onto the bed. The woman got up on her knees and pulled her top off, baring her big tits. "Come on, Stacy, tits out!" she said. Stacy pulled her top off. "What he really likes is to watch 'em bounce," the woman said. "Let's give him a show." She started bouncing on the bed, and Stacy joined in, watching in fascination as the woman's large breasts shimmied and shook. "Look at him," Kelly's mom said. "He wants to start jacking off. Let's encourage him. Come on, big guy, get that dick out and start stroking!"

"Come on," Stacy joined in, "show us your cock!"

The man stood up and dropped his shorts, his big dick standing out straight. As he started jacking off, Kelly's mom turned toward Stacy, reached out, and started squeezing her breasts. "Oh, you have nice tits," she said. "Doesn't she have nice tits, Carl? They're so firm!" Stacy was a little freaked out at having a woman squeezing her tits, but not nearly as freaked out as she was a second later, when Kelly's mom slid her hand down Stacy's pants. "Oh, you're wet!" the woman said. "Carl, she's soaking wet! You want a cock in you, don't you, sweetie?" Stacy had to admit it sounded like a good idea. "Let's get those pants off, and Mr. Jameson can give you what you want."

Kelly's mom helped her take her pants and panties off, and then she lay down on the bed and spread her legs open. "Look at her, Carl," the woman said as she took her pants off as well, "what a little slut, huh? Ready for a good fucking. Come on, get yourself some teenage pussy." Mr. Jameson grabbed Stacy's knees and pulled her towards him so that she was laying with her legs off the bed, then he slid his big dick right in her.

The woman was up on her hands and knees, leaning over Stacy's face, her big tits hanging down and swinging. "There you go, sweetie, doesn't that feel good? Doesn't he have a nice cock?" Stacy wasn't sure if the woman was aware that this was the second time that day that she'd had his dick in her. Probably not, she figured. Then the woman leaned over and started kissing Stacy, right on the mouth. A few seconds later they were tonguing each other and the woman was squeezing one of Stacy's tits. They kissed for quite a while, and Stacy was surprised to realize that she was really pretty turned on by it; her heart was pounding and her pussy felt great, with that big cock sliding in and out at a nice steady pace. Then the woman moved up, so that her big tits were hanging in Stacy's face, and Stacy couldn't help herself, she latched on to one of the woman's nipples and started sucking. Her breasts were soft and warm and motherly, and the nipple felt wonderful in her mouth; suddenly Stacy understood why guys liked tits so much.

"OK, Carl," the woman said, "it's my turn now. I need some cock too, you know." She lay down on the edge of the bed next to Stacy, spread her legs, and the man pulled out of Stacy, moved over a couple feet, and rammed his dick into his wife. Stacy lay next to Kelly's mom and they kissed while her husband fucked her, then he pulled out and went back to Stacy and fucked her some more. He switched between the two of them a few more times while they tongued each other and played with each other's tits, and then, when he was enjoying Stacy's cunt for a little while, Kelly's mom got up on her hands and knees and looked back at her husband. "I need your cock in my ass," she said. The man pulled out of Stacy and went behind his wife; Stacy couldn't see what was happening, but she could tell from the look on the woman's face, her eyes were squinting tight almost as if in pain, then she let out a couple of moans, and Stacy knew that big dick was in her ass.

Kelly's mom opened her eyes and gave Stacy a feeble smile. "He really likes fucking ass," she said. Then the woman reached a hand down to Stacy's puss and slid a finger into her, then pulled it out and reached down further, rubbing it around her anus. "Have you ever had a cock in your ass?" She pushed her finger into Stacy's bottom, rubbing her sphincter in a circular motion.

All Stacy could do was shake her head. She was pretty worried about where this was going.

The woman smiled. "Carl, you've got a virgin asshole here!"

The man pulled his dick out of his wife. "I don't know," Stacy said, but it was too late. The woman had climbed up so that she was above Stacy's head on the bed, and grabbed her legs behind her knees and pulled them towards her, so that her knees were practically in her face. She felt the man's dick against her anus, and then felt a searing pain as his huge head forced its way into her, forced her sphincter muscle open to allow its girth inside her bottom.

"Oh god," she said in almost a whisper, looking up at Kelly's mom, "it hurts!"

"I know, sweetie," the woman said, "but he likes to do it, and a girl does what the man likes to do." She felt him start to slide his cock in and out, the pain almost unbearable, particularly when his head left her and then pushed back in, stretching her anus open again. The woman must have known that she needed comfort, because she leaned over and put her big breasts in Stacy's face. Stacy latched on to one of her nipples and sucked, feeling the wonderful motherly love of the breast.

She doesn't know how long it lasted. She just sucked and sucked, and gradually the pain subsided. Eventually he pulled out and climbed up onto the bed and started jacking off with his cock right in her face. She knew what this meant, he was going to blow his load on her. She didn't want him to, but it was a relief to have him out of her bottom so she didn't really care. Kelly's mom lay down so that their faces where next to each other and they started kissing as the man jacked off above them. After a little while, he reached down and grabbed Stacy's chin and pulled her face over so that she was facing his cock, point-blank range, aimed right at her mouth. She pursed her lips together tightly as she could and he fired his first shot, a giant load, right at her mouth, so strong that some forced its way into her mouth despite her best efforts to prevent it. Then he aimed his cock at his wife's face and let go of another big shot, much of which also landed on Stacy. He continued to unload on the two of them for some time.

Kelly's mom was giggling when he finished. "God, he always unloads so much!" she said. Then she leaned over Stacy and started kissing her, sliding her tongue into the girl's mouth. Stacy could taste the man's come on the woman's mouth, could feel his come, slippery and sticky, in between them as the woman pressed her face against hers. Then Kelly's mom lifted her face, stuck her tongue out, and started licking come off of Stacy's face, rolling it on her tongue and then swallowing, or getting a nice sticky glob and then kissing Stacy, putting her come-covered tongue into the girl's mouth. Then the woman reached up and wiped some come off of her own face, then reached down to Stacy's pussy and started rubbing her clitoris, using the come as a lubricant.

It felt great to have the woman masturbating her, she certainly knew exactly what to do, and shortly Stacy felt herself losing control of her body as she began to orgasm. Kelly's mom knew she was beginning to come and sat up a bit and placed her big breasts right in Stacy's face. Stacy latched onto one of her nipples and sucked hard as her body began to shake and she orgasmed. She never wanted it to end, it felt wonderful to come for the woman and to have her soft, warm, motherly breast in her mouth as she came. The woman knew perfectly what to do and was able to keep Stacy in orgasm for quite a while, slowing down and then speeding up, causing her to come over and over. Eventually Stacy was exhausted. "Thanks," she said feebly to the woman. It was the finest orgasm she had ever had.

Stacy was quite sore the next day, particularly her bottom. She felt relieved that this was her last full day at the cabin. Kelly's brother was in a good mood, and doted on her continually. He was obviously hoping he'd get some more pussy before she left, and even though she was very sore, she thought it was cute and wanted to give him a little bit more fun. But, it turned out, not much to Stacy's surprise, that she'd have to give a bit more fun to his father as well.

They drank again that night, and Kelly's dad took Stacy by the arm and led her to his bedroom. He told her to undress and get on the bed and he would be right back. When he returned, he had Kelly's brother with him as well. He dropped his pants, grabbed Stacy behind her knees and pulled her to the edge of the bed, and started fucking her, not even caring that she was still dry. After a while, he pulled out.

"There you go, Steve, she's good and ready for you." Steve looked at her a little sheepishly, but she smiled at him. "It's OK," she said, "go ahead." So the boy dropped his pants and slid his dick into her.

"Take your time," his dad said, "enjoy that little pussy as long as you can." Then the man climbed on the bed and put his big dick in Stacy's mouth. She could taste her pussy on his dick, and it was unpleasant, but she knows how to give a good blow job and started working her magic on his dick. It was fun, actually, to have one big cock in her mouth and another one in her cunt.

"Steve," the man said, "you ever had a girl suck you before?"

"No," the boy said, still working on her pussy. He'd actually gotten fairly good at it and was able to set a decent pace.

"Oh, you gotta try it. This little tart is really good at it, too." The man pulled away from her and climbed off the bed, while the boy pulled out of her pussy and climbed onto the bed in his place. As she started sucking the twelve-year-old's dick, she felt the man slide his big nasty into her. He gave her a really good, hard fucking, and she knew he was going to unload inside her this time. When he was finished, he pulled out. "OK, Steve, your turn. Come over here and let's fill that little womb with Jameson sperm!" The boy's dick slid right in and it was only about ten good hard thrusts before he started unloading as well.

All in all, Stacy thought to herself on the car ride home, it wasn't a bad vacation. She was a little sore, to be sure, but she had a good time.