Crossdressing PI

mikeinindy

Submissive bottom
Joined
Oct 7, 2023
Posts
56
I have dressed totally fem when I have traveled on business and seldom at home. But when a case I was working warranted it I decided that it would a good way to solve the question that my client wanted answered: is his son Queer or not.
A client in Florida hired me (licensed private investigator) to locate his son here in Indiana. He lost contact with him over the years a tofter he divorced his wife, the boys mother.

It took awhile but I discovered that the boy's mother threw him out of the house, where he lived with her. This boy was 18 and moms' boyfriend no longer wanted him around. So, I started out looking for him, not knowing anything about him. I left my card with a lot of people and finally had a lead that led me to a store where he was working. I did locate him and identified him as the one I was looking for and identified myself when I asked him to meet me outside the store.

He was very happy to know his father was looking for him. So I put them in touch with each other. Dad said he would send him an airplane ticket and he could come stay with him. Now all I had to do was follow the kid around and see what I could find out about him. It did not take long before I followed him to a gay club one evening, where crossdressers hang out. This gave me the opportunity to dress up myself and go into the place, something I had always dreamed of but could not get the courage.

I went to my office in a hurry and put on my outfit I had ready to wear: bra, panties, thigh hi hose, short dress, blond wig and 2" heels. I drove to the club, paid admission and started walking around. I was so surprised to see all the open sex taking place before my eyes. I was immediately turned on to see men on their knees satisfying other men, and some bent over being taken from th rear. I was in heaven sexually and so turned on. I had to find my clients son and it did not take long before I saw him at the bar talking with another guy. The other guy had his hand on the boys crotch rubbing him and soon was unzipping his pants and. playing with, stroking his hard on. That went on for awhile and then they went to a booth where they took turns stroking each other and soon the boy was going down on the other guy, an older (maybe 30) individual. I loved watching it all.
Then they stopped and walked to where I was sitting at the bar and started talking to me and asking if I wished to join them. I felt that I had overplayed my role but I wanted very much to have sex with this boy, and his friend. I was in no position to say no. The three of us went the the booth and my clients son was soon feeling me up and lowering my panities and stroking me. Gawd I was so hard and excited and soon was in his mouth. The other guy had the kid in his mouth. We soon stopped and the kid kissed me hard, deep as he stroked me. Then he whispered, "I know it's you Mr Wright and I want you".

I was shocked but turned on that this young man wanted sex with me. I kissed him and thanked him and told him I wanted him also. He told me when he saw me come into the place he knew it was me and thought it was cute of me to follow him. He said he was excited that I would go to all that trouble to follow him. Then he asked me to make love to him! Wow, I wanted him very much and it seemed that the other guy wanted to take me from the rear. So, Gary (my clients son) pulled down his pants and bent over in the booth and pulled me to him and I was soon inside of his smooth and very cute rear end as I began to give it to him. And soon I had someone inside of me too....pounding me hard, deep and rough. It did not take the guy inside of me very long before he exploded all over my backside.....and as I kept giving it to Gary I felt like I really belonged in this place. Here I was doing what I enjoyed so much, having sex with other men, and dressed like a slut. Anyway Gary was moaning and groaning and taking out loud about how much he enjoyed having me inside of him.....telling me to go deeper and harder. He begged me to "give it o me hard" as I thrust into him. Well, it did not take me much more time and I erupted all over his cute ass and he collapsed onto the cushions and then I stood up, only to have another guy bend me back over and take me from behind. It seems we had drawn a crown and others were watching. By the time the second guy finished using me for his pleasure, others were having their own fun.

I thank Gary and told him I would see him later. He walked me out to my car, kissed me, and thanked me for the pleasure I gave him. I thanked him too, knowing I was going to have him more before he left for Florida. Such a cute ass!
 
I have dressed totally fem when I have traveled on business and seldom at home. But when a case I was working warranted it I decided that it would a good way to solve the question that my client wanted answered: is his son Queer or not.
A client in Florida hired me (licensed private investigator) to locate his son here in Indiana. He lost contact with him over the years a tofter he divorced his wife, the boys mother.

It took awhile but I discovered that the boy's mother threw him out of the house, where he lived with her. This boy was 18 and moms' boyfriend no longer wanted him around. So, I started out looking for him, not knowing anything about him. I left my card with a lot of people and finally had a lead that led me to a store where he was working. I did locate him and identified him as the one I was looking for and identified myself when I asked him to meet me outside the store.

He was very happy to know his father was looking for him. So I put them in touch with each other. Dad said he would send him an airplane ticket and he could come stay with him. Now all I had to do was follow the kid around and see what I could find out about him. It did not take long before I followed him to a gay club one evening, where crossdressers hang out. This gave me the opportunity to dress up myself and go into the place, something I had always dreamed of but could not get the courage.

I went to my office in a hurry and put on my outfit I had ready to wear: bra, panties, thigh hi hose, short dress, blond wig and 2" heels. I drove to the club, paid admission and started walking around. I was so surprised to see all the open sex taking place before my eyes. I was immediately turned on to see men on their knees satisfying other men, and some bent over being taken from th rear. I was in heaven sexually and so turned on. I had to find my clients son and it did not take long before I saw him at the bar talking with another guy. The other guy had his hand on the boys crotch rubbing him and soon was unzipping his pants and. playing with, stroking his hard on. That went on for awhile and then they went to a booth where they took turns stroking each other and soon the boy was going down on the other guy, an older (maybe 30) individual. I loved watching it all.
Then they stopped and walked to where I was sitting at the bar and started talking to me and asking if I wished to join them. I felt that I had overplayed my role but I wanted very much to have sex with this boy, and his friend. I was in no position to say no. The three of us went the the booth and my clients son was soon feeling me up and lowering my panities and stroking me. Gawd I was so hard and excited and soon was in his mouth. The other guy had the kid in his mouth. We soon stopped and the kid kissed me hard, deep as he stroked me. Then he whispered, "I know it's you Mr Wright and I want you".

I was shocked but turned on that this young man wanted sex with me. I kissed him and thanked him and told him I wanted him also. He told me when he saw me come into the place he knew it was me and thought it was cute of me to follow him. He said he was excited that I would go to all that trouble to follow him. Then he asked me to make love to him! Wow, I wanted him very much and it seemed that the other guy wanted to take me from the rear. So, Gary (my clients son) pulled down his pants and bent over in the booth and pulled me to him and I was soon inside of his smooth and very cute rear end as I began to give it to him. And soon I had someone inside of me too....pounding me hard, deep and rough. It did not take the guy inside of me very long before he exploded all over my backside.....and as I kept giving it to Gary I felt like I really belonged in this place. Here I was doing what I enjoyed so much, having sex with other men, and dressed like a slut. Anyway Gary was moaning and groaning and taking out loud about how much he enjoyed having me inside of him.....telling me to go deeper and harder. He begged me to "give it o me hard" as I thrust into him. Well, it did not take me much more time and I erupted all over his cute ass and he collapsed onto the cushions and then I stood up, only to have another guy bend me back over and take me from behind. It seems we had drawn a crown and others were watching. By the time the second guy finished using me for his pleasure, others were having their own fun.

I thank Gary and told him I would see him later. He walked me out to my car, kissed me, and thanked me for the pleasure I gave him. I thanked him too, knowing I was going to have him more before he left for Florida. Such a cute ass!
That would be so much fun. I've always fantasized about having a couple feminize me into their maid to serve them and their close friends.
 
You want a man and woman to feminize you or just another CD?
My X knew exactly how to femininize me. I think women have a better fashion sense. My X would suggest several panties and tops for me and would coordinate colors and style. Soon I learned to do that myself. I love sheer white lace, purples, and of course black lace is very dramatic. When I am in a fun mood, pinks, and cute little girl panties with Lit' Ponies, or Care Bears are totally fun.
 
My X knew exactly how to femininize me. I think women have a better fashion sense. My X would suggest several panties and tops for me and would coordinate colors and style. Soon I learned to do that myself. I love sheer white lace, purples, and of course black lace is very dramatic. When I am in a fun mood, pinks, and cute little girl panties with Lit' Ponies, or Care Bears are totally fun.
You were fortunate to have help and an understanding woman
 
Back
Top