Tag Archives: crossdresser

Starting To Dress Up

 

 

Some of my guys I have talked to for years. This is one of my sissy guys that ordered some stuff off line.  It depends on the guy but some of them I enjoy making them go out to shop. Not every sissy can handle this because of the level of embarrasment so I have to adjust to personality. It is a lot of fun to shop online together as I generally do not live anywhere near the guys that I play with. I have had a few transgender and crossdressing girlfriends that were close to me. We would always enjoy taking some time and hitting the mall together. Most of the “girl” that I knew where more conservative in dress and most dressed 24/7 so it was all slacks, skirts, bras and panties. The guys on line that just dress for fun time tend to want the more slutty fuck me know look. There is nothing wrong with that and lots of fun to play with but getting fitted for it at the mall by a teenage girl is generally way over whelming.  If you would enjoy showing off some of your outfits send me a picture or two and tell me a little about it in an email. dianecallaway@gmail.com

skirt