Posts9

I got a call from Amber, my ex girlfriend who got me into crossdressing, a couple of days before New Years saying Caroline was looking again for some help hosting for New Years eve. With New Years eve being a Saturday night she was expecting a huge crowd. Amber and I had already made plans to go out bar hopping that night, dressed of course.. Amber and I had been going out once or twice a month for the last couple of months. Our relationship is a strange one. We sometimes go months without seeing each other then other times we do a lot together. Its probably I'm her go to when she is not… Read more

Amber, my ex girlfriend who got me into crossdressing, called me the week of Valentines saying she needed my help. A friend of hers, Caroline, had recently opened a restaurant and needed a couple of people to be hostess fro Valentine weekend. She was expecting a big crowd and wanted everything to go smooth. I had meet Caroline a couple of times through Amber and had hung out. She's a pretty cool person. At first I told Amber I would pass. She kept begging me. She said hadn't seen me much lately, we have a real love hate relationship, and that it would be a great time. I finally said ok… Read more

I got my start dressing at Halloween with an old girlfriend (that will have to be another post). Now that I dress on a regular basis and think I do I better good job off it what do I do? I have been invited to attend a work friends Halloween party where everybody dresses up and my old girlfriend (whom I'm still friends with and knows all about my dressing) has invited me to her party. So what do I do? Going to the work party would be good for work but wouldn't feel comfortable dressing as a girl so what would I go as. If I go to the old girlfriends party I could dress as a girl in some wa… Read more

Every couple of years a few friends and me get together to have 3 days of playing golf. This year we had at the beach. So I worked my schedule to see a few customers on the way and to get there a couple of days earlier than the rest of the guys. One of the guys has a condo there that we were going to be staying. I checked with him and nobody had rented so I was going to stay there. I wanted to have the extra day to dress. Something about being away from home and dressing is more relaxing. I guess at home I'm always worried about running into someone I know and getting recognized. Chance… Read more

I haven't posted in a while been real busy with work which has cut down on my dressing. As all of girls know it takes a little bit of work to make this happen. I guess I just got caught in a rut. I did go out several times Christmas shopping and had a blast. An old girlfriend of mine that I keep up with invited me to go to a Super Bowl party with her. Now you have to keep in mind that she is partially responsible for me crossdressing. Its a whole other post a will write one day. The short of it is that she supported and aided in the dressing. She really enjoyed it. We broke up over… Read more

I was on my way home the other night from a business trip. About an hour from home I had to stop for gas. As I was pumping the gas I was just looking around checking out the area around the gas station. I noticed a nation wide discount clothing store that sells clothes for men, women and c***dren that I have always seen advertisements for on TV. I began to wonder if the clothes were as good what is on the commercials. So being in no rush I decided to go check it out to see if there was anything worth buying. As I drove up I wondered if they were closed because there were not many cars in… Read more

This being my first summer really to seriously dress has been a challenge. In the past if I dress I didn't go out. Here are some things that have been a challenge: 1. Sun Tan Lines - I'm an outdoors person so I get a fairly good tan in the summers. Back early summer/late spring I got dressed to go the grocery store. I had just bought a new very casual skirt and blouse that I was going to wear flip flops with. I get all dressed and look down at my feet and saw how white they were compared to my legs. Also learned have to watch out for tan lines around the neck and shirt sleeves. I have h… Read more

I have been telling myself I needed to finish telling about my trip to Nashville but things have been busy since then. Well here it goes. When Kevin and I had finished having sex and gotten dressed we started to head back to the den with Pam. As we were walking back in Pam was smiling ear to ear. She motioned for me to come get under the blanket with her on the couch. She asked if had fun. I smiled real big and said I sure did I don't know about him. He looked over and smiled and said it was great. In a few minutes Pam said we needed to freshen up and took me by the hand to her room.… Read more

This is a follow up to my previous post about going shopping and meeting Pam. We made plans while having a few drinks the night before to go out on the town the next night. She asked me what I had always wanted to do when I thought about going out in public. I told her I had thought about anything from going to the movie, dinner, concert or just hitting some clubs. Although not some wild club. She threw out a couple of ideas that sounded good and that she would think about it more. She told me just to relax and come dressed and confident she would take care of the rest. I got through… Read more