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I don’t recall the exact circumstances that swayed me into trying on my first female garments but it started around the time I was 17ish. A lot of the things I tried on were my sister’s cloths which worked out cause most of the time she was at college an I was able to sneak into her room and try on a few things. It wasn’t until she decided to donate a lot of her cloths that I took the opportunity to take a few for myself. I had a small box of things, a dress or 2 a pair of heels and some under garments. I had these for a couple of years wearing them for a thrill now and again.
It was maybe 2 years into college I was ashamed of what I was doing and purged everything because I felt really bad and was wondering why I was doing it. During college I still had a part time job I did when I came home for vacation and during the summer months to have some spending money. I worked next door to a Walgreen’s and they used to throw out all sorts of random items, from towels to dispensers many useful items and im not proud of it but I did dumpster dive, and one day a while after I purged my girly items a lady dumped a huge bag of cloths and shoes into there which got me very excited and ended up taking the whole bag back home to try them all on to see if anything fit. I also got a nu-bra a while later so I had a slightly larger collection of cloths and items I really enjoyed but regrettably i ended up purging a second time and that was difficult to do.
I finally graduated from college and had a good steady income and my now collection of cloths was started. I ended buying tons of different types of shoes all kinds of dresses in different materials. While living at home I ended up with so many thongs I bought 3 huge storage bins for under my bed to hide all my girly items. This has now become a hobby of mine. It wasn’t until around this time that I shaved my legs for the first time. Which as most of you know feels fantastic with a new pair of pantyhose. I ended up slowly trying out more things like ways to get my boobs to look right and fake nails but very little makeup nothing really crazy in that regard.
About 2010 or so I told my friends I was going to dress up as a girl for Halloween. I got as far as shaving my legs and even going to the party but I couldn’t find anything to wear and I chickened out. I enjoyed the party but was extremely nervous about doing that in public even among people I know. Since living at home I was very limited on when I would dress up, I had to be careful no one would be home or bother me while I was dressed so I didn’t have to change in a hurry back to boy cloths.
Things really changed for me when I moved out at 25 to my own place where I really got to have fun being dressed. I had the freedom to do it whenever I wanted, I played with makeup wigs and everything it was fantastic. I still kept this side of my life locked up Ina tight safe, I truly thought this is something I would NEVER tell anyone. It was in 2012 where I had a lot of bad things happen to me, just life happened and it wasn’t fun. What really helped was that Halloween I was going to do it and go out as a girl. It was my mission, I became determined. I practiced my makeup and put it all together myself. One thing stood in my way, for 10 years I had a goatee a very distinguishing feature that I had to get rid of. It was very difficult to do one of the hardest things to do. I actually mentioned shaving it several times at work so no one thought anything other than I did it for the hell of it.
I had to make the trip from Queens where I lived to Brooklyn in an area I never been dressed as a woman. The whole experience was surreal, I finally had the nerve to leave my apartment and waited at a bus stop since I didn’t want to walk the long distance to the subway in my wedge boots. I sat there for 20 minutes until I had to ask someone and the store was open behind me. I walked up to the door and the guy inside actually thought I was a woman til I spoke. I was thrilled inside I got that reaction, it only got crazier from there. That guy I asked for directions ended up closing the store and giving me a lift to the subway. Most bizarre conversation I ever had. He did ask me what my name and that’s when I said Vanessa. I thanked him for the ride and as I got out of the car the grabbed my butt. I was in shock but at the same time was feeling fantastic. I ended up turning quite the few heads no knowing if I was a guy or girl. It wasn’t until I spoke that they knew. I didn’t try to do a female voice but its something I am trying to work on. I did end up getting lost and having to touch up my makeup. The biggest payoff was at the party when I saw my friend, it took him almost a minute to figure out it was me. The expression on his face was priceless and the best part of the night. I had a blast was out for about 6 hours that night and it was something I wanted to do again, but hated having to wait until Halloween to do it again.
The end of the year ended on a very terrible note, on December 21, the day the world was suppose to end I got hit by a car. I got a hip contusion and fractured my front tooth in 3 places. It could of been far worse but I did lose my front tooth and still am trying to get it fixed almost 2 years later. It was a hit and run which makes that situation all the more fun to deal with. Up until this point, except for a select few of people who were not at the party, no one knows I even did that and even those people who saw me don’t know I enjoy to do that on a regular basis.
Everything for me changed for me in a big way when I met my current girlfriend. We met from my sister working for her father who set us up. She lived far away but seemed to have similar interests and we started emailing back and forth. When we first started talking on the phone I mentioned the Halloween story and showed her pictures which she loved. Then I was feeling so comfortable with her I told her that I enjoy doing it all the time not just a Halloween thing. She shared something very personal wih me after that and we really connected together. One thing about my previous relationships I never mentioned this to any degree but with her I was completely honest I didn’t want anything to be a secret.
It wasn’t until I met her that I even felt comfortable to even consider myself a cross dresser. She has been so supportive and we get to talk about anything together. The irony is, I’m more of a girly girl than she is. Not that she is a full on tom boy but would rather be casual than dressed up. We ended up swapping cloths and she helped me do my makeup and gives me pointers. Being able to fully share this with her has been the best thing that happened to me. I thought I would have to keep this secret with me forever, but now because of her I actually want to tell more people because of how she makes me feel. We end up talking about both half’s of my personality as 2 people. So in essence she is a part time lesbian. So many time people would take a statement like guys don’t know what women go through or something stupid like that and she just laughs cause she knows the truth.
I apologize for the long post but I wanted to share this story with everyone here because of how supportive my girlfriend is to me. She has given me the confidence to say I’m Vanessa and I crossdress. I feel bad for those who have to keep that part of yourself hidden from the world or not even able to share it with your significant other.
I am happy to be a part of such a caring community, in that way we are truly never alone.
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