Shotacon (also Shota) is a Japanese and anime term for a sexual complex where an adult, usually male, is attracted to an underage boy. Traditionally written or drawn by women and for women, shotacon fanservice or hentai basically includes depictions of characters under high school age, sometimes with a partner who is usually older. Because shoutacon art tends to emphasize cuteness, common themes are yaoi, crossdressing, or even incest with an older sister or relative.

Boys are stereotypically perceived as being more interested in sex at a young age than girls, so shotacon used topically, especially as a source of humor, is usually more well-received and less stigmatized than the lolicon counterpart. In addition, many male fans enjoy mild shotacon themes as a form of wish-fulfillment due to the use of older, attractive women in a sexually dominant position or as a romantic/sexual instructor. This runs against the typical view that hentai (or anime in general) idealizes virginal, submissive girls and portrays men as overly aggressive partners. Thus whether a situation reflects josei-con (e.g., Onegai Teacher) or shotacon (Haunted Junction) is largely up to the author.

The phrase derives from "Shotaro complex" (Shotaro is a hero character from Tetsujin 28-go and is a popular generic name for young male characters in anime) and is sometimes contracted further to shota. Shotaro, in those anime and manga, often outwitted and was never afraid to say what he had to against ungainly grownups. Except for few occasions where his physical limits failed him, he had everything that could be had for an adult. His appearance was also deemed cute.

Where this shotacon concept developed is hard to prove but one of the earliest root of this syndrome can be traced to readers responses to detective series written by Edogawa Rampo featuring a cool detective Kogoro Akechi. In it, Yoshio Kobayashi and his friends form "Shonentanteidan" (Junior Detective Group, similar to the Baker Street Irregulars of Sherlock Holmes) to aid Mr. Akechi. Kobayashi was written as a perfect young teenager who, some might say, had a strong "dependency" to Mr. Akechi. Every time he appears, he is either worried about Akechi's well-being or helping Akechi set the trap for criminals. On the numerous occasions that he was captured, Akechi swooped in for a timely rescue. He even lived together in the Akechi's house who happened to be not married. In short, he acted almost as though he was Akechi's wife and no doubt few female readers had not read the stories picturing themselves to be in Kobayashi's position.

Bridget, a crossdressing young boy of the video game series Guilty Gear became infamous on image boards like Futaba Channel and 4chan as a shotacon sex symbol, whose cuteness was lauded by otherwise vehemently straight fans. Usually depicted in his blue nun habit, he became instantly recognizable even when his origin and sex wasn't. Canonically, he dressed as a girl to avoid the supersitious persecution of twins, and has an honest desire to become more manly, fanworks usually depict him in a feminine or even lolicon style of dress, although still anatomically male.