A bored hacker modified an Eliza programme to act as an IRC sex-chat bot that impersonated an eighteen year old girl (or, rather, impersonated a sex-chat afficianodo of indeterminate gender impersonating an eighteen year old girl). He assumed that people would try to have cyber-sex with his bot and get bored, but in fact a surprising number were convinced and even got off with it.
This is a plot element in Bruce Sterling's brilliant "RU486?" a short story collected in Globalhead -- feminist hackers finance their RU486-running operation with a phone-sex line staffed by automated chatterbots.
It turns out that pornbots are among the class of Eliza-derivatives that can pass a Turing Test (or rather, horny sex-chat boys are among the class of human beings that can't tell a chatterbot from a person -- other groups include psychotherapists, who, in one experiment, couldn't distinguish actual transcripts of therapy sessions with schizophrenics from simulated therapy with schizophrenic chatterbots; and the university student who mistook a chatterbot for his prof in the middle of the night when he IMed same for permission to extend deadline on a late paper).
'eliza' is a program that talks to you, pretending to be a psychologist. its script of possible responses is super tiny, so it doesn't fool anyone. or so i thought.
IRC is a network full of chat rooms (or "channels") where a lot of scary internet people (or "perverts") hang out. my friend reduz found a version of 'eliza' that could go on IRC. he put it on IRC. a lot of people from other countries thought it was a real woman, so naturally they tried to have sex with it. they got frustrated quickly. reduz is a bad man...
so i replaced eliza's tiny, boring script with a massive dumb blonde script that has like 3,800 responses on all sorts of topics, but mostly sex. jenny18 is very horny and she loves talking to horny guys. and everyone knows the best place to talk to horny guys is on dalnet irc sex channels.
Link (Warning, contains links to transcripts of IM-based sex, NSFW)
Update, Zed sez, A bot on a MUD was horndogged by an individual for two weeks
without him getting it. Note that while the bot was designed for a
modicum of verisimilitude, it was not designed to fool anyone, or
targeted to fool horny boys.