I'm new here, but I thought I'd post a fun night out I had in heels a few months back.
I think it was a Friday night, and I was feeling tired of only wearing my heels in the house, So I decided I would dress up a little and go out for a night of dancing at the club. I wore a very simple tight fitting navy blue long sleeve dress that went down to about my mid thighs, with a pair of reasonably opaque black tights, and a pair of 5 inch platform stilettos. I don't think anybody was mistaking me for a woman, but I am a pretty tall, thin, young guy so I think it was actually a good look for me. I decided to go to a LGBT/Latino club in Phoenix that is known to be a popular place for transvestites.
I got to the club pretty earlier actually, and it was pretty dead inside which made me feel pretty nervous. I was hoping to blend in with the crowd, but for the first hour or so this was not the case. No one was really dancing at this point so I went outside to sit on the patio, and a guy and a girl approached me. They told me they were from Colorado and that they were cousins. They were very nice, and made me feel a lot less nervous about the situation. They told me how much they loved my outfit and wanted to know if I was straight or gay. I told them I was straight, and the girl cousin said she figured as much, but the guy cousin continued to hit on me, which I didn't mind so much:) I eventually exchanged numbers with them, and they told me they wanted to dance with me later inside, and I told them I would.
In the meantime I continued to sit on the patio for a little while longer, at which point an entire group of bearded transvestites came up to me and started talking to me. They were pretty obnoxious to be honest, but they all LOVED my outfit, especially my heels. They complimented me on how well I walked in them and gave me a reference of a make up artist who they said could help me with my look.The leader of them all laughed because she was amused by the fact that someone was actually taller than her, but was very nice about it.
Eventually I made my way back inside and met up with my two Colorado friends I met earlier and began dancing. The heels I was wearing were about 5 inches tall and have about an inch platform which makes walking in them very manageable. The only problem is though that they are about a half size too small, so it didn't take long before my feet really started to hurt. Despite the pain however, I was having an amazing time. Both the cousins were very good dancers and were very out going and having lots of fun.
Eventually though I could bear the pain no longer and I had to say goodbye to my new friends. I didn't bring a change of shoes so I had to walk back to the car which was in an uneven dirt parking lot. I was talking really small steps at this point and wasn't sure that I looked attractive at all, but alas I made it back to my car and took my shoes off for the drive home. I wish I could say that it was sweet relief, but my feet were still throbbing even after I took the shoes off.
Overall though it was an awesome night out. I'll have to do it again.