Jennifer Evolving

I am a hetrosexual crossdresser
My crossdresing started at about 11 or 12 but I knew I was different even earlier in life. I hated sports and most activities  boys love. I had much rather play house, pretend or even play with my sister's dolls. One night, I was 11 or so, I was getting ready to take my shower. My sister had just taken hers and left her clothes in the bathroom floor, as usual. As I was getting undressed I saw her panties and bra in the floor and wondered what it would feel like to wear them. After looking at them for a few moments curiosity got the better of me. First thing you know I had her panties on as well as her bra. From that moment on I have been hooked! I couldn't get past how wonderful they felt on me, but more important it just felt right to be wearing them . Needles to say, my sister was short a pair of panties and a bra, and I never got round to taking a shower that night as I intended. I snatched a few other pairs of her pantes and bras over my teen years and put them on as often as I could. Thru my 20's 30's and early 40's I continued to dress once in a while, mostly in just lingerie. Many times there was days weeks and sometimes months between my dressing episodes.

At about age 44 or 45 something inside me changed. I started to want to dress fully and very shortly after the desire to go out dressed emerged. On one of my days off I decieded to go shopping. I already had most of the lingerie items, so I bought a couple of skirts a pair of pantyhose and a couple of tops, just enough for a starter wardrobe.  I sat at my computer for hours each night researching make up and reading make up tips. After I thought I had it down, I ordered a couple of pair of heels and a wig from an online store. After getting my starter make up kit heels and wig I was so excited, I could hardly wait to become the woman I felt I was inside. After putting every thing on and appling my make up I saw really fast I wasn't as skilled as I had hoped.  At this time I was dating this GG who sometimes poped in unannounced. Well she poped in and cought me in a pink mini skirt. After the initial shock wore off she started helping me with my make up, and pointing out what Iwas doing wrong. This helped me greatly! Unfortunatly our relationship wasn't long after that,she told me she didn't think she could deal with my "issues" on a day to day basis. It was at about this point I was just sitting watching tv (dressed of course) when I thought I must pick out a name for the woman that I am fast becoming. After a few days of thought I settled on Jennifer for my first name. I have always loved that name for a girl and it was the name of my first real girlfriend, we dated throughout high school. I now had to think of a middle and last name. I didn't want some of the "play on words" names that some cd's take, but rather a somewhat common name. After coming up with a few names in which I quickly rejected I chose Morris, which is my real middle name.  I choose Lynn for a middle name simply because it sounded good with the other two.

Since then I have ventured out on many occasions, and seem to pass pretty well. I do still have a major problem in the lovelife dept. When women find out my secret they run like I had the plague. I seem to be two different people, one personality in guy mode, and another as Jennifer. In guy mode I am very shy and not at all a people person. I hate crowds and go out of my way not to attract attention to myself. As Jennifer I am just the opposite, I am far far from shy and love being the center of attention. Seems I am Jennifer more and more as time passes. About the only time I am in guy mode now is when I go to work. I am afaid I won't have a job anymore if I come out at work, and in times like now I can't afford to risk it.

jennifergurl jennifergurl
51-55
4 Responses Mar 2, 2009

I too have felt the urge to completely dress up since I turned 45. My wife draws the line at wearing regular clothes, but has let me wear nightgowns and panties while having sex. She allowed that for several years, but has asked me to stop wearing her nightgowns when she can see it. I still wear panties every day and she is fine with that. She thinks they are sexy. I think that a woman has to be very understanding and open minded, but not necessarily bi to allow it. Some women are turned on with wearing their own type of clothes and lingerie.<br />
<br />
It is unfortunate that most women cannot understand it or tolerate it though.

I to have been dressing since an early age but I was and still am into cars and I never thought that I was in the wrong body. Then as I was about 8 I had this compulsion to put on a pair of knickers and I have had this compulsion ever since, now I am still trying to figure out what drives this compulsion because although I love dressing en femme I don't know how to feel feminine, because I know deep down that I am a man .I to live a life on my own I would love to find a girl in Australia that would except me for who I am because I love the feelings that I get from my dressing and they are not sexual as they are for most ,sorry for the generalisation but this is what I have seen.

Hi MY LOVE well Darling you are no different than all of us here at EP. We all had similiar ways of getting into our women's clothes. I am Samantha and I am 61 and I as you have been doing this all my life. All of our stories are just about the same. I take it for granted that you are in North America so you will find that most women from this continent do not have very much staying power when presented with a cross dresser and I believe that for a women to really stay with her man as a CD'er she has to have Bi tendencies. So we enjoy our lives alone or together as you may discover in time. Take Care Samantha

Congratulations Jennifer for having the courage to follow your dream. I'm sorry you're having trouble finding a woman to accept you. We are out there. My lover has loved lingerie since small kid time. He looks good in it and totally enjoys it. He enjoys being made love to while wearing it and it allows him to fantasize about having a male lover (do strap ons count as cross dressing *wink*) As part of his love for lingerie he's gotten very familiar with it and what he chooses for me is gorgeous! He has turned me into a total lingerie *****! We dress up in our 'pretties' and totally get off on making love to our altnernate personas.