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Chapter 2
by Sacremas
Who is the next Client?
Chloe, the transgender of Mistress Daria
Frank arrived at Mistress Daria's large house, the place was luxurious with fine art hanging on the walls, and a large staircase that led to the bedrooms. Frank was excited for this job, Daria had paid him a large sum of money, and the picture of Chloe wearing only a collar and a chastity cage on her small cock had him rock hard in his pants. He knew that the cock and balls he was blessed with was a gift and a curse, most women were intimidated by their size, and it had left him alone for most of his life, until he had started working as a gigolo. He had met all kinds of women through his job, but Chloe was unique.
Daria greeted him at the door, dressed in a dominatrix outfit. She was a tall, mature woman with long blonde hair, and she had a commanding presence. Next to her was Chloe, kneeling on the floor with her head bowed, naked except for a chastity cage on her cock and a collar around her neck.
"Chloe, go suck his cock," Daria commanded, and Chloe quickly scrambled to her feet and approached Frank. She looked up at him with her big brown eyes, and Frank could see the fear in them. He wondered if it was because of his size or because she was transgender. Either way, he was here to please her, and he wasn't going to let his own insecurities get in the way.
Chloe took his cock in her mouth, and Frank couldn't help but let out a low groan. She was good, really good. She took him down her throat, and Frank shuddered in pleasure. He looked down at her, and he could see the tears streaming down her face, but she didn't stop. She kept sucking him, and Frank couldn't help but feel a little guilty. He didn't want to hurt her, but he couldn't deny the pleasure he was feeling.
"Chloe, get on the bed and spread your legs," Daria commanded, and Chloe quickly complied. Frank watched as Daria pulled a huge buttplug out of Chloe's ass, and Frank couldn't help but feel a little intimidated. He had never seen an ass so stretched before. Daria then motioned for him to come over, and Frank approached the bed.
Chloe looked up at him with fear in her eyes, but Frank could see the desire in them too. He positioned himself at her entrance, and he slowly pushed himself inside her. Chloe let out a low moan as he entered her, and Frank couldn't help but feel a sense of satisfaction. He had never been able to fit his entire cock inside a woman before, but Chloe was different. She was flexible, and her ass was able to accommodate him.
Daria sat next to Chloe and started petting her, whispering gently in her ear. Frank couldn't hear what she was saying, but he could see the comfort it was bringing to Chloe. He started fucking her harder, and Chloe let out a loud moan. Frank could feel her prostate, and he knew he was hitting it just right. Chloe suddenly squealed and shouted for her mom, and Frank was shocked to realize that Daria was Chloe's mom.
Chloe had a powerful prostate orgasm, her petite body shaking as she came. Frank pulled out, and Daria made Chloe suck his cock until he came in her mouth. Daria then kissed Chloe deeply, sharing his sperm with her. Frank left the house confused but satisfied, it was the most unique sexual experience of his life. He couldn't help but wonder what other secrets Daria and Chloe were hiding.
AN: Ran the prompt 7 times, this was my favorite, it's unedited from what the AI came up with. This was the only output where it decided to detail Daria's home.
What's next?
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The Adventures of a Gigolo
The AI-generated stories of Frank's big dick exploits
A series of AI-generated stories, all of them featuring the same main character, a gigolo with a huge dick.
- Tags
- MILF, Dominatrix, BDSM, Trophy Wife, Anal, Strippers, Cuckhold, Cheater got caught, Redhead, Queen of the Night, Vampire, Wonder Woman, Goddess, Muscular woman, Female Bodybuilder, Huge Cock, Male Prostitute, Gigolo, AI Generated, Single Mom, Cervix Penetration, Student, Spectators, Bulging belly, Hot Nerd, Cock Worship, Transgender, Chastity Cage, Buttplug, Bimbo, Goth Girl, Thicc, Occultism, Sex Ritual
Updated on Jan 21, 2025
by Sacremas
Created on Jan 6, 2025
by Sacremas
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