A submissive married man posts an ad seeking a dominant woman to enslave and humiliate him for an evening, and finally receives an enticing response.
#online-hookup
68 stories tagged with this.
An older writer recounts being contacted online by an 18-year-old self-styled Pagan Sex Goddess from Colorado, leading to a charged email flirtation.
A man in his 60's answers a swinging ad and connects with a woman in her mid-20's who prefers older men, leading to their first encounter.
A man meets a married exhibitionist woman online who wants to fulfill her fantasy of fucking in her office.
A man recalls meeting a woman through a Craigslist NSA ad and the passionate, love-without-strings connection they shared.
A nervous 23-year-old man meets a gorgeous shemale from a dating site for his first sexual encounter with a trans woman.
A young white stud answers a sex ad from an older, heavier-set Black woman seeking a hung partner for a night of intense, no-strings encounters.
A 30-year-old bisexual man visits a 51-year-old man's apartment wearing women's clothes for an intimate encounter.
A man working in Alaska recounts his first experiences hooking up with older women he met through Craigslist casual encounters, focusing on his larger-than-average anatomy.
A man exploring his attraction to other men goes on his first date with an Irish guy he met online, nervous about the encounter but hopeful about the connection.
A true autobiographical account of a man who secretly enjoys dressing as a girl and servicing men, chronicling an online hookup with a stranger who turns out to be genuinely interested.
A self-described straight man creates a profile on a gay hookup site and becomes unexpectedly aroused by another man's photo, sparking a journey of sexual curiosity.
A young woman becomes addicted to anonymous online hookups while grappling with guilt and seeking connection.
Two men meet in an online chat room, exchange fantasies, and one arrives naked at the other's condo for an anonymous sexual encounter.
A male author recounts his first sexual encounter with a woman named Chloe, presented as instant messenger logs featuring anal sex and a finishing blowjob.
A user posts a raw transcript of a cybersex chat with an anonymous partner, escalating through increasingly rough and varied sexual acts.
A woman replies to a traveler's suggestive email proposing a passionate stranger-to-stranger encounter at her door.
A raw chat log between two gay men, one Black and one white, engaging in mutual fantasy and cyber-sex culminating in a blowjob scene.
A submissive white bottom begs his black top over Skype to dominate and breed him in a raw, chat-log style exchange.
A raw IM chat log between two gay men escalating quickly into explicit sexual roleplay and spit-filled fantasies.