A few years ago at a dinner party with friends we made aware that their son then sixteen had come out to them. Distraught and angry his father to this day does not acknowledge his homosexuality. He loves his son and they work together in the family business, but his gay life is not ever discussed.
Fast forward six years and I run into young Jerry at the airport. Turns out we are both attending separate conferences in Las Vegas. I was in first class so I invited him to join me and used some of my miles to upgrade his seat. We had a few drinks and Jerry began to soften his protective shell. I point-blankly told him I had no problem with his sexual orientation and we got on well the remainder of the flight.
He accepted my offer of a ride to his hotel and we jumped into the back of the limo. I immediately turned on the privacy screen and pulled out my cock. His eyes went wide. Just semi-erect it looks like a beer can. He was all over it, giving me a mind-numbing blowjob and swallowing a massive pent-up load. We went straight to my hotel and I had the bellman take his bags to my suite. I had a massage lined up after the flight so I told him to go up to the room and dress for dinner.
About an hour later I got to the suite and was pleasantly surprised when Jerry greeted me in a tight red mini-dress, spiked heals, and full makeup. He was nervous that I wouldn't approve. To the contrary I assured him. I would prefer that he dress as woman. Other than his time at the conference Jerry was en femme. I convinced him to stay through the weekend with me. My cock was in his mouth or very cute ass most of the time.
We both agreed that what happened in Vegas should stay in Vegas...but my wife is taking the kids to her mom's beach house for a month...a month is a long time.