While Bill is in New York City on business, Allison Moore, the girl escorting him to his room, observes that he doesn't have a wedding band on, so she makes a pass at him by petting his penis! Bill tells her, shocked, that he recently got married and isn't wearing a wedding band because they're still getting fitted. However, Allison doesn't care because all she's doing is measuring his enormous cock to see how it would fit in her mouth, between her tits, and up her hot pussy!
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Billy meets Riley Reid at traffic school, and they flirt. Billy requests her daily ride to school, but she agrees to fuck her until she cries, likely to sleep on it.
Mia Gold takes Bill, her husband's coworker, out of his job to discuss her partner's affair. Bill initially resists, but eventually admits to her affair with a stripper. Mia refuses to have it, but wants Bill's sex.
Professor Holly West discusses his relationship with his tennis student Bill, who becomes upset when she advances. Bill promises not to cheat, but his teacher threatens to flunk her class and take away his tennis scholarship unless he fucks her.
Holly confronts Bill, her friend's brother, who spreads rumors about her. Bill admits his feelings for her and feels gratified, demonstrating his crush on her by giving her a runaround.
Rilynn Rae seeks support from her new neighbor Billy after her abusive partner leaves her. Billy invites her to hang out and offers her help. Rilynn Rae expresses her love and passion for him, making him feel loved and supported.
India Summer returns to school, becoming the cougar of the classroom. She seeks help from Bill, the teacher's assistant, but becomes preoccupied with fantasizing about putting Bill's cock in her pussy. This leads to Bill being tempted.
Sadie Holmes discovers an arts and crafts fair and invites her friend Bill to join. She finds Bill alone, and she experiences his large cock, which she eagerly awaits to try firsthand. She is determined to never let it pass her by.
India Bill, Summer's student, is troubled by excessive testosterone. India believes she knows the problem and offers help, but she resorts to fucking Bill to alleviate his troubles.
Mia Gold takes Bill, her husband's coworker, out of his job to discuss her partner cheating on her. Bill initially resists, but eventually admits to her affair with a stripper. Mia refuses, but Bill's sexy appearance is desired.
Bill, his wife's designated driver, enjoys a party while his wife is bored. Sovereign Syre, finding Bill attractive, takes him to a private room, causing Bill's spouse to feel unfairly excluded.
Jasmine Delatori visits Bill's house to groom his dog, feeling attracted to him as his replacement for a sick colleague. She enjoys sitting on Bill's dick, but Bill is unsure about it.
Veronica Avluv is upset with Lexi Belle, her boss's new secretary, for not being qualified for the position. She demands her boss can Lexi stay. Bill defuses the situation by apologizing to Lexi and using his dick to destroy her pussy, resulting in a successful outcome.