Hello everyone, I'm new here and new to the world of cross dressing. Sorry about the long post, but I would like to tell you a little about myself. When I was young, i remember my sister and her friends would often dress me up and put makeup on me, and I remember likeing the idea of it. Of course I was young so I really didn't have a clue what was really going on. Fast forward to my teens year and I started getting interested in cross dressing, but never really pursued it due to the fear of getting caught since I lived with my parents.
I went through a period where I pretty much forgot about cross dressing, until my girlfriend at the time moved in with me. Now I had an arsenal of clothes and makeup at my disposal. I often tried on her clothes when she wasn't home, but was to intimidated by makeup to try it, so I never did. We eventually broke up and she moved out, and I never told her my secret.
Fast forward a while, I had been dating another girl for a while. To keep the story short, she was a very close minded person, and did not support some other things about me, and often made fun of me about it, and eventually told her friends. I never told her about wanting to cross dress, I knew she wouldn't be supportive. In fact I had mentioned about guys cross dressing to her once and she basically said you would have to be really messed up in the head to do that, and if I ever dated a guy that wanted to do that, I would dump him so quick. So the choice was fairly obvious. Not to long after that, we broke up for unrelated reasons, and I'm so glad we did. However, the way she treated me made me retreat even further into the closet about my secrets and made me uncomfortable to even think about it.
Fast forward to present day. I've been dating my current girlfriend for over 3 years now, and up until a month ago a just have kept cross dressing out of my mind. I frequent Reddit often, and I stumbled upon a cross dressing sub, which reignited the spark in me to try again. It was wonderful to see the amount of support the community offered and made me feel confident enough to try. At this point I didn't know what to do. Things had been going great with my girlfriend, and I worried what would happen if I told her. I ran the scenarios over and over in my head and concluded it's best to just bite and bullet and do it, so I decided to just text her a question. I asked her if she thought I would look feminine in makeup, girls clothes and a wig. I worried that her response was going to be snarky and rude, but much to my surprise she responded by saying she didn't know, but we could give it a try. It opened a whole dialogue, which led to her going out the next day and getting me clothes and makeup. She looked for wigs and order me a wig, and has been watching tutorials. Long story short is she is 100% supportive of me crossdressing and it honestly is the best feeling in the world.
My goal is to be able to go out in public dressed, and she is completely supportive of going out with me, we even joked about going to bars to see if we can get guys to buy us drinks. At the end of the month we are going to the beach and i plan on showing off my shaved legs, shaved armpits and shaved chest as well as my painted toenails, it will be my first step in the right direction.
I hope that I can get some feedback, support, constructive criticism and tips from you all, and hopefully make some new friends!