The Crossdresser In Therapy

Billy had been seeing a psychiatrist for almost a year, and was no closer to figuring anything out than he was on day one.

Three times a week he would come in and say pretty much the same thing: “I like to dress up as a girl but I feel guilty about it.”

Both he and Doctor Gestalt realized that not only was he making no progress, but that he had spent close to $30,000 so far. Billy was frustrated, and often thought he would have been much better off if he just bought that motorcycle he wanted instead of telling his deepest secrets to a complete stranger, and paying him a lot of money just to listen.

Finally out of desperation he told the doctor this and asked what he thought he should do. Much to his surprise the doctor was sympathetic and had a suggestion.

“Why don’t you just buy a dress? I know where you can get a gorgeous spandex mini dress for $30, and if you need a custom size its only $5 more.”

Billy considered that for a second, and was about to discuss the available colors when it stuck him as odd that the doctor knew this.

“Wait a minute-wait a minute, how do you know where to get a cute mini dress? Holy crap, you must be a sissy!”

Doctor Gestalt took a hit from his cigar and smiled. “No Billy, I’m a crossdresser. There’s a difference you know?”

“Are you fucking kidding me? Why didn’t you tell me? I spent a fortune here and you just sat there asking me what I think and smoking that stupid cigar?”

“Doctor Gestalt wiped the ashes from his $2,000 slacks and said: “For one thing you never asked me, and more important what I do in the privacy of my home is none of your business. By the way, I’m selling my BMW GS and I can give you a great deal on it.”

Billy considered everything that was said in the last ten minutes, the money he spent, the hours in the smokey office, and took a couple of deep breaths as taught by a previous therapist. Then he calmly got up and hit Doctor Gestalt so hard that he fell off his $8,000 antique chair and lay moaning on the floor.

“OK Doctor Sissy, how much for the GS?”

It took Doctor Gestalt a minute to catch his breath and pick himself up off his $14,000 berber carpet.

“Its Doctor Crossdresser Billy, and if you really want it make me an offer.”


Billy ended up buying the mini dress and the bike and is paying the doctor in weekly installments.

Note: You never see a motorcycle at a psychiatrist’s office. Unless its a very happy guy in a shocking pink mini dress on a BMW R1200 GS.