Josie the Insecure BBW

In the heart of the city, Frank, a man of average stature with an extraordinary endowment, arrived at Josie's modest apartment. The door creaked open, revealing a sickly sweet smell of garbage, a stark contrast to the woman standing before him. Josie, a 26-year-old woman with a glandular disorder that had made her obese, was a sight to behold. She was dressed in a large sweater and baggy pants, her pale skin peeking out from the fabric. Her brown hair was pulled back into a messy bun, and her green eyes were filled with a mix of nervousness and anticipation.

Frank, a seasoned gigolo, was not deterred by Josie's appearance. He had been in her shoes once, wallowing in self-doubt and depression. He was determined to give her a night she would never forget. With a confident stride, he closed the distance between them, pulling the surprised Josie into a deep, passionate kiss. His hands roamed over her body, feeling the softness beneath her baggy clothes. He pulled off her sweater, leaving her in just a large, unappealing bra that struggled to contain her huge breasts.

Frank had been worried beforehand that he might be turned off by Josie's obese body, but her large breasts were a nice compensation. The ability to sink his hands into her soft body felt strangely comforting. He caressed her breasts, unclasping her bra and freeing her ample assets. He suckled on her nipples, eliciting a soft moan from Josie. Meanwhile, he worked to remove her pants, revealing her large, soft body.

Once Josie was naked, Frank reassured her gently, telling her not to worry. He then removed his own clothes, revealing his huge cock. Josie's eyes widened in surprise and pleasure as she saw his dick was already half erect and clearly not disgusted by her. She carefully grabbed it, feeling the warmth and hardness in her hand.

Frank led Josie towards her large bed, where he lay down, inviting her to explore his cock as much as she desired. Josie, a virgin who had lost her hymen through the use of sex toys, was eager to experience a real cock. She ran her hands over his shaft, marveling at its size and girth. She took him in her mouth, sucking and licking him, feeling him grow harder in her mouth.

After a while, Frank told Josie to lie down. He spread her legs wide and began to lick her pussy. Josie had never felt anything like this before. Frank's tongue danced over her clit, sending waves of pleasure coursing through her body. He slid a finger inside her, preparing her for his huge cock.

When Josie had a nice orgasm, Frank carefully inserted his cock into her. She was tight for him, but she stretched nicely, accommodating most of his length. Frank admired the way her huge breasts moved with the sway of his thrusts. He sucked on her nipples, caressing her body, and making love to her as best as he could.

Josie had several massive orgasms under Frank's skilled touch. She had never felt so desired, so loved. Frank's huge cock filled her in a way she had only dreamed of. She wrapped her legs around him, pulling him deeper inside her.

Frank could feel his orgasm building. He pulled out of Josie and had her kneel before him. He came in her mouth, watching as she swallowed every drop of his thick cum. Josie thanked Frank for treating her well, for making her feel beautiful and desired.

Frank smiled at her, telling her it was just part of the service, and part of being a decent human being. He left Josie happy, ready to make a new attempt at enjoying life. As he drove away in his old car, he thought about Josie and the other women he had helped. He may have been a gigolo, but he was also a healer, helping women find their confidence and sexuality.

And so, Frank continued his job, helping women find pleasure and confidence in their bodies. He was not just a gigolo with a huge cock; he was a man who cared about the women he was with, who treated them with kindness and respect. And in doing so, he found his own happiness and fulfillment.

AN: Story is unedited from what the AI wrote based on my prompt, unfortunately I didn't save the prompt for this story either. Written using Smitten Plus.