A young man continues his spring break hookups with his boss, boss's wife, and dorm mate in an explicit bisexual encounter.
#first-time-anal
33 stories tagged with this.
A clandestine lover arrives for an evening of champagne, roses, and first-time anal play with their secret partner.
A straight-presenting married man explores his latent bisexual submissive desires after his wife encourages him to seek out a recently-released ex-convict who wants to dominate him.
The male camp nurse carries his injured young lover through the mountains after their first anal encounter.
A young woman recounts losing her anal virginity to her boyfriend and her preparations for anal sex with him and his friends.
Hazel and Kate continue their relationship as Kate introduces the inexperienced brunette to anal sex.
A woman recounts her first anal experience with her demanding flatmate, who insists on taking her roughly despite her hesitation.
A man gradually introduces anal sex to his partner who initially viewed it as a moral sin, through patient communication and mutual exploration.
A teenage boy narrates his first sexual experience with his innocent boyfriend Aron, who eagerly asks to be penetrated for the first time.
A ranch husband guides his curious young wife through her first enema and anal experience with humorous banter and eager preparation.
A young woman begs her daddy to take her anal virginity in a taboo father-daughter encounter.
A polite contractor seduces an older female client after a wine-soaked lobster dinner, with anal and fisting on the menu.
A teen girl reconnects with her ex-boyfriend at a Starbucks and the encounter leads to passionate intimacy.
A lonely, self-described 'slut' teen manipulates her teacher into taking her in the ass as part of a revenge scheme against her ex-best friend.
A lonely teen girl diary entries detail obsessive self-harm, masturbation with toys, and first-time anal as she mourns her lost lover.
A man fulfills his long-held fantasy by taking his little sister anally, describing the act in graphic first-person detail.
An exhausted woman comes home to her partner who gently initiates her first anal experience after a long day, blending tender massage with sexual exploration.
Michael teaches Silk how to masturbate and they share their first anal experience together in a continuation of their lifestyle education.
A curious young man follows through on a promise to return the favor, leading to his first experience with anal sex.
A gay college freshman continues his sexual relationship with his straight roommate, who asks to practice anal sex on him before a winter break tryst with a girl.