Caribbean vacation

Jack's mother washed him from an early age and he had become accustomed to her nakedness. Only in recent years did she shave her pubic hair, and he now looked at her childlike‐looking slit with new eyes, he wasn't a baby anymore. After his shower, he stood in the bathtub and masturbated without squirting, every day. She sat on the edge of the bathtub and watched him, she was getting horny. She usually masturbated for a long time and in a horny way because the little boy only stopped rubbing his cock when she was shaking and trembling in orgasm.

Her eyes shone and glittered when he squirted for the first time in thick jets. He looked at her, helpless and confused, as jet after jet splashed into the water. "Finally, now you're a real man!" she said happily, lathering his cock carefully and washing it. "You don't have to stink of semen!" she commented.

The next day he didn't want to masturbate anymore. She looked at him questioningly. "I saw you fucking a stranger the day before yesterday!" Jack said cheekily. He was 13 now and he had already fucked some of his classmates in the asshole because they were concerned about their hymen. His mother had thought about it for a long time in silence. "And now you want to fuck me too!?" she murmured and continued playing with her clit as usual. Jack nodded uncertainly and squinted at her clit. "Okay, then" she sighed deeply and sadly after a while, "okay, then!" She stood up, bent forward and leaned her hands against the small box. She stuck her ass out towards him and said, "okay, then! Come on!"

Jack held her ass cheeks wide apart and penetrated her. She laughed loudly, "you're in the wrong hole!", reached between her legs, grabbed his cock and stuck it in her pussy hole. There it was so fine, warm, wet and soft like silk. She wasn't as tight as he had thought. He began to thrust carefully. She nodded, "that's right" and her finger found her clit. He fucked her, but not for long. "Mom, I have to squirt! Can I??" She nodded and gasped, "Yes, of course!" Jack squirted much too soon. He waited motionless until she had finished masturbating, he was already familiar with her masturbating. Then she sat down next to him.

"Daddy hardly ever fucks me anymore, maybe once a month. At first I thought he had someone else and I fucked other men every day, being terribly angry. I'm too young to live like a nun, you understand that, right? But I did him wrong, he never had anyone else. He had simply lost interest and his sexual lust, that was all. I hugged and kissed him because we love each other very much. I rarely cheat on him anymore, only when the sexual pressure really gets too great." Jack nodded understandingly because she was a good Mom and he was a good Dad.

From now on he fucked her every time after a shower. She taught him to hold back his squirting until she had reached her orgasm. It was best when they came at the same time. She hadn't fucked other men since then, Jack did a wonderful job.

Jack was now 16, almost 17. He fucked her every morning after he showered and it was very pleasant and satisfying for both of them. Then his mother won a 10‐day cruise in the Caribbean, she extended the vacation so that they were away for 3 weeks. A friend let her have her housekeeper for the 3 weeks, who would look after Jack. Ulrike came the day his parents flew away. Jack carried Ulrike's travel bag into the parents' bedroom because he had decided to fuck the new girl before he had even seen her.

Ulli, as she wanted to be called, was a small, fat woman with large breasts, about 60 years old and she had a radiant, friendly and engaging smile. Jack was a little disappointed with her appearance, but he would fuck her, whatever the cost. He quickly found out that the illiterate woman had never been to school, could barely spell a recipe and could count the change when she went shopping. She was extremely friendly and would look after him with joy and love; for her he was the master and she his servant. She was naive, simple‐minded and very easily influenced. There seemed to be nothing she wouldn't have done for the young master. As soon as his parents had left, he told Ulli that she should only wear panties and a bra in the house and Ulli took off her clothes without a question; it was more comfortable, said Jack. He looked at her body shamelessly, she looked so cute and somehow sexy in her underwear. Jack was now even more determined to fuck the small, fat woman, no matter what the cost! He was tempted to simply order the simple‐minded, stupid woman to let herself be fucked, but that seemed unfair to him. He wanted to have fun with her seducing. Ulli made a good dinner, then they watched a bit of TV and then he said he would take a shower before going to bed. She should soap him up and wash him a bit; his mother did that every evening. "Yes, of course, Master Jack!" said Ulli. "Mother always comes into the bathroom naked," said Jack as casually as possible, "then her clothes don't get wet," he added. He could see the wheels slowly turning in Ulli's head. "So, naked, without a bra?" asked Ulli with fear and wide eyes. "Yes, of course, Ulli!" said the seducer, "naked, she comes without a bra and without panties, fully naked!" he continued and smiled kindly. Ulli had to think about it first. "So, without a bra and without panties, I'm completely naked, and I'm not used to that." She pondered. "Do you really not mind if I come in naked?" she asked worriedly, "You know, I'm already 64 and not as pretty to look at as I used to be when I was a Photomodel."

Jack pursed his lips. "Photomodel?" he asked slowly. Ulli nodded. "Yes, when I ran away from the orphanage at 18, I lived with a photographer for almost a year. I was allowed to live with him for free if I let him fuck me and take naked photos of me. He took lots of naked photos of me because I was so sweet as candy to look at, he said, and he also made films."

Now Jack just had to ask more. "He filmed you?" Ulli nodded again in agreement. "With strangers, with men." She kept her eyes downcast, they had reached a sensitive point. Jack didn't press. "I'm sure it was fun, you and the men." She looked up briefly, Jack was such a nice boy, he was just friendly and curious, there was nothing bad about him. "Yes, at first he filmed me masturbating alone and faking an orgasm. I just had to quickly slide the foreskin back and forth over my clit, but that soon wasn't enough for him. He gave me very precise instructions to pull back the foreskin and rub my clit with my fingertip like Mom did. I kept running to pee in between, but he didn't care. I was now having hundreds of real orgasms and he liked that more. Then there was a new setting. He filmed me as a stranger fucked me, then another and many others. Some days he filmed me all day, I fucked 6 or more men and had really enjoyable fucks and lots of orgasms, damn it! And at night Huber fucked me too! He filmed us very close up, we had to fuck according to his instructions and really let loose, that was very important to him! Most of the men fucked me very, very well and brought me to orgasm easily, he had to film that in close‐up. I didn't really think anything of it, there were only short but pretty dirty lines to recite, I didn't have to talk while fucking. Most of the men fucked me very, very well and brought me to orgasm easily, which he had to film in close‐up. And to fuck a man or to be fucked was then pretty normal for me." Jack waited and later asked how it went.

"Then I had to fuck several men, but I didn't like that very much. My Dad taught me how to fuck and I let myself get fucked quite often at the time, that wasn't the problem. But that there had to be several men at the same time. It reminded me too much of the gang banging in the orphanage, one squirting in my asshole, one in my pussy and one in my mouth, all at the same time. After having fucked in a dozen films with a bunch of men, I went to Mr. Huber. The photographer, Mr. Huber, understood my resistance. He now brought girls with him, filmed us making out like pigs and the girl masturbating my clit with her hand, her finger. I was supposed to show my horniness openly and scream when I climaxed.

I did it, even though no woman had ever kissed me with her tongue or touched my clit before. But this one made me incredibly horny and I didn't have to pretend anything, I screamed my heart out when she brought me to climax. I didn't have to pretend. All these girls masturbated me the same way Mom had masturbated and they made me scream like crazy when I orgasmed. But overall I found it uncomfortable and filthy, I didn't think it was right that she masturbated my clit. I stopped after a dozen girls and then Huber was really angry and I left. So I became a housekeeper." Ulli looked up at Jack very shyly, but he smiled. "I understand very well that you were fed up with the whole thing and that you left," said Jack and nodded, "Huber just went too far, the stupid guy!"

Jack fetched two glasses and a bottle. "I'm grateful that you listened to me," said Ulli after they had drunk to friendship, "I don't really have anyone I could tell about it." Jack poured more wine. "I actually want to know everything about you, I'm interested in how your life has been. I don't have anyone who would tell me everything either," Jack said. They drank and chatted, then Jack said he was going to take a shower.

Ulli actually came into the bathroom naked. Jack noticed that she only had sparse gray pubic hair and that her melon‐sized breasts hung down low without a bra. He stood in the bathtub and she stood next to him, lathered him up and washed him. She made a big detour around his cock, but he said nothing. Ulli got out of the tub and sat down on the stool. She sat down so, that he could stare directly at her pussy, which she didn't seem to notice. He began to masturbate while standing and sometimes looked at Ulli, but she just watched silently. He looked at her as he squirted into the water. Ulli shuffled restlessly on the stool and finally said, "I saw that when I was a little kid, Dad squirted into the sink until we ... until he didn't do it anymore." Jack waited a bit and asked how it had come about. Ulli told him all.

"I always slept in my parents' bed, the children's room was a junk room because Mom couldn't throw anything away. I watched them fuck night after night, that was just as normal for them as it was for me. Dad would sometimes squirt in the sink, I found that very exciting too. But the idyll didn't last forever. There was more and more screaming when Mom caught Dad fucking very young girls in the living room. I had no idea, I was upstairs in the children's room playing with my dolls and letting each one fuck each other. Mom didn't let him fuck her so often anymore, she was angry with him. She was pretty mad when Daddy showed me how to ride him, but now I had to make sure he could squirt in the evenings because she didn't like letting him fuck her. He lay on his back and his cock lay like a thick sausage on his stomach. I had to press my pussy onto his cock and swing back and forth. "Fuck me, princess, fuck me powerfully!" he said, because he called me princess. I had to swing back and forth and fuck him until he laughed and squirted. When I pushed my pussy all the way forward, it looked like I was squirting. I loved this riding very much. Mom was always angry with our riding and would turn to the side and masturbate in secret. Dad went to prison and that made me very sad. He had fucked a 10‐year‐old girl and was locked up. Mom masturbated every night and I asked, "What are you doing?" But she swore angrily and replied, "It's none of your business, mind your own business!" I tried to do it too, but it didn't work. I had to run to pee immediately, so I stopped trying.

Dad came again, thank God! On the very first night he fucked Mom again, even though she kept pushing him away. This annoyed him very much and he grabbed me. "Do you want to fuck me, little princess?" Yes, and how much I wanted that! Mom couldn't stop him. He quickly deflowered me and then fucked me. He fucked me until I had an orgasm, then he squirted inside. He didn't argue with Mom very often anymore.

When she didn't want to fuck, Dad fucked me. I was very proud that he fucked me like an adult, even though I was only 13. Mom turned to the side and masturbated in secret. At the time, I thought that things were going well for all three of us. I was wrong.

One day, Mom said she wanted to do something about Dad's constipations, he was suffering a lot, but he didn't go to the doctor. She would mix a powder into the semolina porridge today. We would both feel it too, but not as much as diarrhea. I agreed, because I knew how much Dad was suffering from constipation. In the evening, before I went up to the children's room, I looked in the kitchen, but the bottle with the powder was still there. I thought Mom had forgotten it and mixed it into the semolina porridge. I had wasted time and was late for dinner. Mom and Dad were lying with their faces in the plate. I shook them both, but they didn't move. I ran to the neighbor, who came and called the ambulance, who called the police. The parents had been poisoned, Mom had left a suicide note. They committed suicide together.

I was 16 and I was put in a city orphanage. It was pretty bad there. I was fucked every night by one or more inmates, although I rarely flirted with anyone. Often there was a group fuck, I was very ashamed and humiliated because I was fucked in public, in plain view and in front of everyone, by one after the other. Everyone stared at my cunt during the fucking. I eventually left, after a year or two. That's how I came to meet the photographer Huber."

They were silent for a long time, then they went to bed. The next day Ulli got into the tub with him again and washed him. He touched her skin, it was old and wrinkled and got goose bumps when he touched her large breasts and nipples. She was very excitable there, her legs trembled a little and the goose bumps got stronger, as he caressed her teats for minutes. He remembered that. She sat down on the stool, but Jack didn't masturbate. He asked her if she masturbated often? Ulli shook her head, no, never since she was a teenager. Didn't she need an orgasm? She thought for a long time and decided to answer. "Yes, every night I ride my pillow like I did when I was a child, riding my Daddy's cock, and doing so I always get an orgasm!" She was breathing heavily because she found it difficult to reveal this secret. "Can I masturbate you now, Ulli?" asked Jack and Ulli took a sharp breath.

"Why?" she asked timidly. Jack said he had done it many times and was quite good at it. That was a blatant lie, of course, he had been allowed to watch his mother and some of the girls at school, but not touch them. His mother didn't make such a fuss as the girls did, she let him watch if he wanted to. It had always been like that, ever since he could remember.

"Like the girls at the photographer's, with their fingers?" asked Ulli timidly and he nodded, "Yes!" Ulli thought for a moment. "But you're not filming!" was the last hurdle she saw. Jack replied that he wasn't such a scoundrel like Huber, he didn't exploit her and sell the films like that bloody scoundrel. "I only do it for my own pleasure, because it makes me really horny," added Jack. "I haven't been horny for a long time!" shouted Ulli. She thought again. "With an orgasm?" she asked, because it was beginning to dawn on her that this was what was going to happen. Jack nodded again, "until orgasm, of course, that's the whole point." "I haven't been masturbated since I was 19, I've had screaming orgasms, back then." Ulli remained silent, there was nothing more to say.

Jack came out of the tub and knelt down in front of her. She closed her eyes as he rubbed her nipples until her legs trembled. He pushed her knees apart, pushed aside the sparse gray pubic hair and looked at her pussy up close. She had a fairly large pussy hole, that was the first thing he noticed. Maybe that was because he had made her very horny. Her clit was longer than his mother's, at least 4 centimeters long. It had already come out slightly from under the foreskin and was throbbing very lightly in her pulse. He rubbed her clit very gently, for over 10 minutes, and only then did he notice from her breathing that she was ready. He increased the speed and the pressure. Ulli opened her eyes, staring in his eyes with horror. She couldn't avoid that he made her orgasming so easily. She threw her head back and the orgasm broke over her, rolling and surging in her hips and in her fat ass. Then it was over.

"This orgasm is much stronger than the one from pillow riding!" she exclaimed. Jack asked if she liked it and she nodded. He said he would like to do it to her every time after he showered. She said nothing, but she looked at him for a long time. "And now I want to fuck you!" Jack shouted and stood up, his stiff cock bobbing. Ulli laughed, "I'm 64 years old, fat and wrinkled, why do you want to fuck me!?" Jack said, "Because I don't like rubbing myself and because I much prefer real fucking!" Ulli looked at his cock bobbing right in front of her face. He's ready, she thought, he has to fuck now! One last try. "I'm 64 and the last time I fucked was when I was 19. The last time I fucked Huber, over and over again, so I could stay a few more days. He filmed that too, he had to film everything!" Jack didn't wait any longer and let her stand up. He would never kiss that wrinkled mouth with the ugly teeth, but he would definitely fuck her. Now.

He had her take the same position as his mother. She had to stand with her back to him and bend forward, she could support herself with her hands on the small box. He spread her buttocks. So he could see her thick labia and the huge hole. He penetrated her large cunthole, but it seemed to adopt it's size to his cock. Her cunthole was dry and soft, much wider than his mother's. She didn't react, she stood simply there with an indifferent expression on her face. Like a sheep she looked in his eyes, her mouth half open. She didn't react a bit and he fucked her for a very long time. Although her pussy hole seemed very huge to him, it was just as enjoyable to fuck as his mother's, whose pussy hole seemed much smaller and tighter to him. He fucked and fucked and Ulli didn't make a sound. "Is it good?" she asked worriedly several times and he nodded each time, "Yes!" He felt it rising and he didn't have to wait for her orgasm. He squirted inside, he squirted until he had finished. They straightened up and he hugged her warmly. "After you shower, you'll do it with your finger on my clit and then you fuck me, will it be like this from now on?" asked Ulli and he answered, "Yes, we'll do it exactly like that!" The days flew by in a flash.

The parents were back and now standing in front of the house. Jack heaved Ulli's travel bag into the taxi and gave her a kiss on the cheek. "Thank you, Ulli, thank you!" He stepped back next to his mother. She knew immediately that Jack had fucked Ulrike.

"Was it okay, Jack?" she asked, putting an arm over his shoulder.

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