After another moment of silence. “Well, I have recently become interested in watching cross dressing and shemale porn.”
“Can you tell me about those fantasies?”
“I can’t explain it but seeing a man dressed in women’s clothes and submitting to either a woman or male really is exciting to me. Perhaps it makes the reality of having sex unreal so therefore it’s ok. I once tried wearing some of my wife’s clothes just to see what it felt like.”
Sean looked at me, “How did that make you feel?’
At this point, I felt totally free to share my feelings about something very personal and which I would have never thought I would tell anyone. “On one of her trips I tried on some of my wife’s clothes. I enjoyed wearing her bra, panties and nylons. Looking in the bedroom mirror I fantasized about kneeling before a master as he ordered me to remove my panties and put my head down and ass up. He would then play with my ass before fucking me. That was crazy.”
Looking like a true professional Sean said, “Not at all that is not an uncommon desire. Have you ever really wanted to act on it?’
I immediately said, “NO, of course not.”
At that moment Sean moved his hand to my crotch. “Your truth detector is telling me a different story. Now tell me the truth!”
It was funny when Sean moved his hand to my crotch, I made no attempt to pull away or protest.
After a moment of silence, Sean whispered. “Jim, undo your belt and unbutton your pants.”
His firm voice commanded my respect and without resisting I unbuckled my belt and unzipped. I did what he said but was uncertain what would happen.
In a few seconds I found out. Sean’s right hand slipped under the waist band of my underwear and my cock and balls felt his touch as he rubbed them. Although our table was dimly lighted, I saw a smile on Sean’s face as he pulled his hand back.
“Jim, if you are willing to trust me and spend a few hours with me tonight I can liberate you from your repressed feelings and fears. All you need to do is follow my instructions. I can make you a new person able to find peace and satisfaction with your life. Are you willing?”
At this point my emotions were swirling. My logical mind kept say “no don’t go” but my emotional self-kept saying, “You have suffered this guilt and frustration long enough go!” This internal debate went on for several minutes as we finished our beer in almost silence.
“Jim, are you coming with me or staying with your fantasies and frustrations?”
“Sean, I don’t know what this means but I am going with you. I only hope this won’t be the biggest mistake of my life.”
He smiled, “It will be one of the best decisions. It is time for you to pay for my professional services so pay Brent and let’s go”
After I paid the $35.00 bar tab and left another $10 tip for Brent, we walked out to the parking lot. Sean said, “I live only about 5 minutes from here.”
As I started to move towards my car, I said, “I will follow you.” “No, I want you to ride with me. Your car will be safe here. ”
Sean drives a black Mercedes with tinted windows. “Get in Jim. I will get us there quickly and you can relax. Let me ask you. Of all your fantasies does submitting to a woman or a dominant man or woman or being a naked sub submitting to humiliation to either of both have the strongest appeal?”