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 © 2025 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

FSC 2026/2027 Board Members Announced

The Free Speech Coalition (FSC) has announced the results of its 2026/2027 Board of Directors election.

Report: AVS Group Beefs Up AV After $1.3 Million Fine

Adult content provider AVS Group has begun to institute robust age checks on some of its websites after U.K. media regulator Ofcom last week imposed a penalty of approximately $1.3 million for noncompliance with Online Safety Act regulations, the BBC is reporting.

FSC: Federal Report Confirms Unfair Banking Discrimination Against Adult Industry

The Free Speech Coalition (FSC) today announced that a federal report on debanking has concluded that several U.S. banks engaged in discriminatory banking practices against members of the adult industry.

Pineapple Support Names Natalie Pereira Executive Assistant

Pineapple Support has appointed Natalie Pereira as its new executive assistant.

AEBN Publishes Popular Searches by Country for October, November

AEBN has released the list of popular searches from its straight and gay theaters by country in October and November.

FSC Summit Event Schedule Announced

Free Speech Coalition (FSC) has revealed its slate of networking events and symposiums for its annual summit, set for January 15 during XBIZ 2026.

Pornhub Releases 2025 'Year in Review' Report

Pornhub has released its “Year in Review Insights” report for 2025, the 12th edition of the site’s annual statistics, data analysis, and infographic initiative.

Washington AV Bill Jumps on 'Health Warning' Bandwagon

A new age verification bill in the Washington state legislature would require adult sites to post notices warning users of alleged health risks, despite a previous federal court ruling against such requirements.

BranditScan Launches '25 Days of Christmas' Promo

BranditScan has launched its 25 Days of Christmas promotion.

MelRose Michaels Named Host of Online Industry Edition of XBIZ Honors

Performer and entrepreneur MelRose Michaels will MC the online industry edition of the 2026 XBIZ Honors, set for Wednesday, Jan. 14, at the Kimpton Everly Hotel in Hollywood.

Show More