The Babysitter Anna - Cover

The Babysitter Anna

by Rickyboy

Copyright© 2025 by Rickyboy

Fantasy Sex Story: Anna is a 22 year old 5 foot 2 inch, almost 200 pound chubby, actually obese young woman. She is a bit ashamed of her size and appearance and has never dated because of that.

Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa   Reluctant   Heterosexual   Fiction   Cream Pie   First   BBW   .

Anna is a 22 year old 5 foot 2 inch, almost 200 pound chubby, actually obese young woman. She is a bit ashamed of her size and appearance and has never dated because of that. Anna would like to meet men, especially since she reads a lot of romance novels and often gets aroused by erotic scenes. Often after reading, Anna masturbates with her fingers, massaging her clitoris. She has many times planned to buy a dildo to help her masturbate better. She’s wondered what it would feel like to put a dildo in her pussy because she’s still a virgin. Sometimes when she’s scrolling through Tinder, she’s thought about offering herself to someone to fuck, just to lose her virginity. But no one has approached her through the app, and Anna herself hasn’t dared to offer herself. She studied to be a nurse, and occasionally worked as a nanny to earn a little extra money. life as a student was hard and her studies didn’t allow her to have a full-time job. Last week Anna had been babysitting 3-year-old twin girls, but only for three hours, so the pay wasn’t great and she would need more childcare opportunities to earn more money. Anna has been dreaming of a vacation, somewhere warm in the south, maybe to a sunny Spanish beach.

Anna had been babysitting for almost two years, and the parents of the children at the nursery trusted her skills and ability to care for children of different ages. On her way to school, she always checks the notice board of the nearby nursery, because there are often jobs posted there for her. This time, a more special ad had come in. It wasn’t actual childcare, but weekend care for a 26-year-old man with a developmental disability. Anna read the offer carefully and the man’s mental development had fallen to the level of a 5-7-year-old. The offer was financially good and would greatly improve her finances. Anna called the phone number provided and announced that she would accept the job. It was the following weekend and there were only two days left. On Friday evening, Anna traveled by bus to her family, which consisted of a father and mother and a 26-year-old man named Tommy. The parents were going to visit their daughter and her husband for the weekend to see their newborn grandchild. As a result, Tommy needed a nanny because he didn’t want to travel due to his fear of flying.

Anna received good instructions from Tommy’s parents, and what Tommy’s routines are like. Before leaving, they said that the neighbor’s pensioner, Mr. Rothmann, might be coming to return some tools he had borrowed, and that he has a key to their apartment. He may come unannounced but knows you are babysitting their son. The parents left and Anna was left alone with Tommy. After dinner they played a couple of different board games, and after that Tommy played simple children’s games on the computer by himself. After the game, it was time for Tommy’s evening bath and Anna prepared the warm water in the tub. Tommy can undress himself, but Anna has to take care of his washing. When Tommy was undressed, Anna’s eyes widened in amazement. Hanging between Tommy’s legs was the biggest penis Anna had ever seen, and even then, only in porn videos on the internet. Anna couldn’t do anything else but stare at the huge organ. Tommy stepped into the bathtub, and Anna recovered from her shock and began to wash him. She also had to wash Tommy’s penis, which had begun to stiffen from the touch of Anna’s hand. Tommy’s penis was enormous, absolutely enormous. 99.99% of men in the world would envy Tommy’s penis. Now that it had stiffened to its full glory, it was It was 13 inches long, if not 13.5 inches. The circumference at its thinnest point is 2.5 inches, and the mushroom-shaped head of the penis is almost 3 inches. Anna didn’t know how to react to what she saw and Tommy’s body, so she decided to be professional and rinsed Tommy off and asked him to get out of the tub. Anna started to dry off the man. By the time she had finished drying Tommy and asked him to put on his nightgown, the big penis had already softened into a resting state. Now Anna felt her pussy getting wet and she had blushed when she realized it.

While making evening meal for Tommy, Anna couldn’t get Tommy’s big penis out of her mind. After Tommy had enjoyed his evening meal, he went to watch the children’s cartoons. Anna put the rest of the food in the fridge and while Tommy was watching videos, she went to Tommy’s computer, opened the browser and started searching the Pornhub site for videos with big cocks.

Anna got excited while watching and she slowly began to rub her pussy over the pants. And it wasn’t long before she opened her pants to better rub her clit. It felt so good, the big body he just saw in his mind, even though the video on the screen showed a big-cocked man fucking a woman from behind. As her orgasm approached, Anna began panting more and more. Suddenly Anna’s orgasm arrived as her fingers rubbed the clitoris inside the pants and she couldn’t hold back her moans as the orgasm shook her whole body. Anna almost lay down on the couch and at the same moment Tommy asked. -what are you doing? Anna hadn’t heard Tommy enter the room while masturbating and was startled by Tommy’s question. He couldn’t answer anything for a moment and Tommy asked the same question again. Now Anna answered, still panting a little in the aftermath of her recent self-produced orgasm.

“I made myself feel good. It’s called masturbation.” A video of a man fucking a woman from behind was still showing on the computer screen. Tommy looked at it with interest, and Anna noticed that the hem of the nightgown was beginning to rise. As Tommy watched the fucking, the large organ had begun to stiffen again. Although his spiritual development had remained at the level of a little boy, he was an adult, in his prime and a physically well-developed young man to whom God had blessed an enormously large tool for reproduction. After Tommy had watched the video for a while, he asked, “What are they doing?” Anna thought for a while about what she would answer Tommy’s question, she decided to say “They make love and feel good to each other.” Tommy was still interested in watching the video where the fucking couple had asked to be set up as missionaries. The man continued to fuck the woman hard on video and the woman panted almost the same way as Anna just now. Tommy’s big organ had already stiffened to its full extent, and the Houst of the nightgown was already bulging at the point of rupture. Tämmy looked at Anna and asked the question again: “Can we make love and feel good?” Anna was completely taken aback by the question and didn’t know how to answer right away. Thoughts ran through her mind, now there was a man next to her who already had his cock up. Her long-term wish could come true, someone would fuck her, take her virginity, which had already become Anna’s personal nightmare when she imagined that no one would ever fuck her. Finally he ended up saying. “Yes, we can make love and a feeling of well-being for each other”. Anna turned off the browser, cleared the page history, and got up from the computer. He looked into Tommy’s eyes and said, “When and if we make love, you must never tell anyone, not even father or mother. Will the little one agree to an oath and we can make love?” Tommy didn’t think for a second, he just held out his little rill and the oath was sworn.

Anna started to take off her clothes, first her shirt, then her pants. Tommy had already taken off his nightgown. Anna wondered for a moment if she was really going to do this, and Tommy, as a grown man with the impatient mind of a little boy, pushed Anna towards the bed, fully ready with his great organ stiffened to its full extent. Anna took off her bra and D size breasts swayed as she bent down to remove her panties. Tommy pushed Anna next to the bed and tried to press her into the same position as he had seen a voman in the video. Anna knelt on the edge of the bed, bent over, pressing her head into the mattress, poking her big ass in front of Tommy, offering her virginal hole for him to use.

Tommy didn’t know about foreplay, or how to excite a woman before you push her inside, but settled behind a wide ass of Anna with a big cock stiff. As the massive cock hit her small labia, Anna asked Tommy to be gentle because she will still be a virgin for a while. Tommy didn’t know what it meant to be a virgin so Tommy grabbed Anna’s hips as he had seen the man do in the video, pressed a mushroom-shaped big cock into the small hole. Since a woman’s anatomy has developed through evolution in such a way that a small hole can even expand so much that a baby can come out, the big cock started to sink into Anna’s small pussy. The lubricants produced by Anna’s orgasm earlier helped and Tommy forced his big cock inside Anna with the brute force of a grown man. Anna screamed when she felt her pussy tearing, the hymen burst like a handkerchief as the big cock pierced it easily. Tommy held tight to Anna’s hips as he pushed himself deep into the tight hole, tearing her pussy wider on the way.

 
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