Headmaster Busted for Cybersex

NEW YORK, New York – Caught in a web of his own desire, the headmaster of a chic, over-priced day school in Manhattan's Upper West Side was arrested on two counts of sending pornography to minors.

John Dexter, the esteemed headmaster of the Trevor Day School, is being held on $25,000 bail for distributing porn content to undercover officers posing as teen girls in a chat room.

Dexter was able to pay his bail and has retreated to his home in Tarrytown, N.Y. for an indefinite suspension from his position as headmaster. Dexter is married with two children, said reports.

A graduate of Carnegie Institute of Technology, 60-year-old Dexter has been employed by the Trevor Day School for 24 years. The day school provides private education from nursery school through high school and also has a location on the East side of the city.

Trevor Day School's library was named after Dexter in honor of his many years with the school, and Dexter was a frequent source for education news stories published by the New York Times.

In the meantime, Dexter's computers have been taken as evidence and more charges could ensue once investigators have a chance to examine the contents of his hard drive.

The arrest of the headmaster was made by the High Technology Crimes Bureau's Undercover Internet Pedophile Stings unit, which with today's arrest, chalked up its 78th successful pedophile sting operation to date.

According to investigators, Dexter has been under investigation for the past four months for sending explicit porn pictures to teen girls and trying to lure them into sexual meetings.

Believing the officers to be teens and pre-teen girls, Dexter allegedly engaged in cybersex talks with the decoys and Internet masturbation, said Westchester County District Attorney Jeanine Pirro.

Dexter was finally arrested after he attempted to arrange an in-person sex meeting with one of the girls.

According to authorities, Dexter first made contact with an undercover officer posing as a 14-year-old in June. By October, Dexter was also engaged in regular chat with another officer posing as a fifteen-year-old. Dexter allegedly sent frequent emails to the teen girls describing lewd sex acts he wanted to perform on them.

School faculty and students are said to be in shock over the incident involving a trusted and long-time member of the school's administration. According to the Associated Press, students are planning on publishing a special issue of the school newspaper. The school has also sent emails and letters to parents to allay their fears over the arrest of Dexter.

Copyright © 2026 Adnet Media. All Rights Reserved. XBIZ is a trademark of Adnet Media.
Reproduction in whole or in part in any form or medium without express written permission is prohibited.

More News

Pineapple Support Partners with Better Life Science's 'STD Hero'

Pineapple Support has partnered with Better Life Science brand STD Hero.

Brazil Sets Enforcement Timeline for New AV Rules

Brazil’s National Data Protection Authority (ANPD) on Friday published a timeline outlining planned steps for monitoring and enforcing age verification under the country’s Digital Statute for Children and Adolescents (Digital ECA), which took effect Tuesday.

Utah Governor Signs 'Porn Tax' and VPN Rule Into Law

Governor Spencer Cox on Friday signed into law a bill to tax adult websites and make them liable if minors circumvent geolocation.

BranditScan Launches 'White Glove' Subscription Tier

BranditScan has launched its new White Glove subscription tier for creators.

German Court: Regulator Can't Block Creator's IG Account, Only Posts

A German court has ruled that while a regional media regulatory agency may block specific Instagram posts that include material deemed harmful to minors, it cannot ban an entire Instagram account due to such a post.

Brazil Lays Out Preliminary Guidelines for New AV Requirements

President Luiz Inácio Lula da Silva on Wednesday signed a decree establishing guidelines for new regulations requiring adult websites to age-verify users located in Brazil.

Senate Committee Debates Section 230 Reform

The U.S. Senate Committee on Commerce, Science, and Transportation held a hearing Wednesday on potential changes to Section 230 of the Communications Decency Act, which protects interactive computer services — including adult platforms — from liability for user-generated content.

Pearl Industry Network Offers Free Creator Memberships

Industry trade group Pearl Industry Network (PiN) has launched its free creator membership initiative.

Sam Bird Acquires Fanblast

Sam Bird, former co-director of global talent agency Surge, has acquired creator monetization tool Fanblast and named himself CEO.

'SheHerGirls' Launches Through Paysite.com

The braintrust behind PoleVixens has officially launched a new membership site, SheHerGirls, also through Paysite.com.

Show More