Amazing Night

Well, I really did it. I had to go out of town for two days and decided that I would try to do it right. I went out and bought myself a new dress to go with the heels that I already have. I also bought a new bra, panties, and a garter belt with thigh highs. As I packed this all up, my wife was in the next room sewing and I was getting excited trying to push the limit. I even snuck in some fingernail polish from her. Leaving, I kissed her and told her I would be back late Friday and not to wait up. As I drove out the drive with all my femme things in bag, I became excited thinking that I only had three hours of real work on my two day getaway. It was a two hour drive to the city, but I stopped along the way at an adult book store to purchase a strap-on. My plan was to get to the hotel, shower, dress in drag, and try to find an escort service that had a transsexual for hire to spend the evening with. I wanted her to treat me as Stephanie and treat me like the woman I want to be. If they were to have no transsexuals, then I would hire a girl that would do the same, but use the strap-on while treating me as I am dressed. I prepared myself, painted my toenails and fingernails, and applied makeup, which I had taken from home. Once dressed in my new dress, I walked in front of the mirror and was overtaken with amazement and excitement. It was getting late and I decided to take a drive as Stephanie to pass the time. I took a quick drive around the neighboring streets of the hotel and, in all the excitement, took a wrong turn and ended up getting lost. I was so excited by this time; feeling free and knowing that no one would know me. It was almost an hour before I found my way back to the hotel. As I walked down the hallway to my room, I passed a clean cut young man returning to his room. I started to tremble uncontrollably as he approached me. I was thinking he would know I was in drag. I said hello and as I did, he stopped. I realized we had neighboring rooms with a connector door in between. We exchanged a greeting and entered our own rooms. After I was in my room, I began to pleasure myself from all the excitement. I heard a slight knock from the connector door. I quickly regained my composure and opened the door slowly. He said, "Sorry for disturbing you, but I had this bottle of wine and did not want to have a night cap alone." After we both had several drinks, he kept explaining about wanting a discrete relationship with someone that understood the way. All along, I still thought he was two drunk to realize I was in drag, but he came out and said he new I was a man but what we do is our own business. It turned out to be what I had hoped for. He treated me as a lady the rest of the night and into the morning. I had never thought of myself as gay or even wanting to experience all this with anyone other than a female, but this made me rethink my sexual role. I realized I am in love with being a cross-dressing gay and this will lead to a lot of amazing nights. The next day we exchanged numbers and he left. The remainder of my stay did not compare to that first amazing night.

— Stephen, 41

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