One Night in Hoboken
In March of 2008, my wife went to Puerto Rico for a week to visit f****y. I decided to take the opportunity to fulfill a fantasy I had for a long time. It would end up going much farther than I anticipated.
Three months earlier I had found a small lingerie boutique in the downtown area of Hoboken, NJ that catered to crossdressers. It was only 20 minutes from my house so I visited several times, but never had the courage to buy anything. After 3 or 4 visits, the owner (Jessica) approached me and said she noticed I came in often. She told me there was nothing to fear and then offered to do a private fantasy transformation for $200. I decided to act on it.
I arrived for the 9pm appointment which was scheduled after store hours so we could be alone. Jessica was very attractive and met me at the door wearing a fitted white top with hints of lace along the plunging neckline that accented her large D-cup breasts. This has always been my weakness and she used them to take immediate control.
She told me to be a good girl and take all my clothes off. She had me shave my legs first. Then, I put on a pink rufflely pair of panties, a lacy pink bra and white thigh-high hose.
She then applied my make-up. I was shocked how much the make-up feminized my appearance. She did eye liner, mascara, foundation, lip liner, lipstick and gloss. My cock was so hard in my panties.
About that time, she told me her friend Carl was due any minute and she wanted me to take some pictures with him for her website. I started to freak out about this, but she put her hand on my cock as she thrust her boobs in my face and told me it would be ok. I looked into her deep brown eyes and seductive smile and felt my resistance melt away.
Carl arrived a few minutes later. He was young and good looking. She told me to be a good girl and unzip Carl’s jeans. He had a bulge already as I slid the zipper down amidst the flash of the camera. She told him to kiss me. I closed my eyes as I kissed a man for the first time. My hand instinctively pulled his cock out of his underwear and started to stroke it. Jessica giggled and called me a sweet little pervert as she continued to click away. This went on for several minutes until she had Carl masturbate himself until he came on my face. She took several photos of this before telling me it was time for my final humiliation.
My cock was still raging hard as she led me to the back door of her store. I was only wearing a bra and panties and I still had cum all over my face, but she wanted me to leave that way! I told her my car was parked 2 blocks away, but she said she wanted me to be a good girl and expose myself to the world.
As I walked out the door into the back alley, she told me to pull my panties down to my knees and stroke my cock openly while I walked to my car. I was hesitant at first, but there was no one in the alley so I did as she said. However, once I got to the end of the alley, I would have another half a block on the main street to get to my car. She said she would walk out her front door and watch me, and that it would be ok.
I was trembling with a mixture of fear and desire. I have never been more turned on or felt more exposed in my life. I just kept hearing her voice in my head telling me to be a good girl and do it. As I got to the end of the alley, I stepped onto the main street sidewalk. It was not too busy but there will still a few people walking around.
I walked about 10 feet toward my car, completely exposed, exhilarated and stroking my raging hard on. I heard Jessica and Carl laugh as she shouted, “Look at the pervert!”
At this point I came so hard that I was dizzy for a few seconds. I shot my load on the sidewalk and then stood there for what seemed like 30 seconds or more. Once I regained my composure, I noticed several people staring and pointing at me in complete disbelief. I sprinted to my car and drove home.
We lived in a condo complex on the second floor. Since I didn’t have any clothing in the car, I had to take a chance and run up to my condo in just my bra and panty. This was by far the wildest night of my life. Fortunately, I wasn’t caught.