Diana and Her Mom by Linda Jensen

The classic story of a crossdresser’s early years is of a very young boy one time being urged on by an older sister, playmate, an eccentric aunt or his own curiosity to play dress-up in girls’ clothes. If others see him he may be praised for his efforts. He feels strangely attracted to this usually forbidden fruit. The occasion passes but the feelings linger.

Years pass but those feelings remain and as the boy passes in to puberty the feelings often become more sexual. However, if discovered, the praise that came to the little boy is often replaced with scorn and shame for the one who is not ‘being a man’. Usually if a young man wants to dress in feminine clothing and act like a girl he must do so in private.

That is more or les my story but that is not Diana’s story. I recently came across Diana over the Internet. We exchanged messages. I was fascinated and not just a little jealous about her youthful experience and what happened when she confessed her crossdressing to her mother. Here is how it unfolded:

In the 1970s Diana/ David was an outwardly typical teenager living in upstate New York. With a stay-at-home mom and a dad who was often on the road, two brothers and two sisters David describes his teen years as,  “I was fairly slender and only 5’7″. I was into running at the time so I developed a more athletic figure but not muscular by any means. I was blessed with a fair complexion and I had wavy shoulder length light brown hair which I really took great efforts to let grow out and wear in pony tails.”

As a teen David was not sure why he liked to wear feminine clothing but he did remember at the age of six willingly being her sister’s dress-up doll. However in his teen years David was on his own when it came to dressing. He found himself more consumed with being Diana.

“I found the opportunities to sneak out to the woods with my sister’s or Mom’s clothes to spend the day sunning on the edge of a secluded field reading magazines like Cosmo and also finding my brother’s Playboys where I dreamed of being a pin up bunny! At the same time it was arousing and stimulating as the fear of discovery kept me always on my toes. I was pretty sure I could always hear someone coming but not sure how I could explain why I was there.”

Like many teens Diana soon wanted to push her limits.

“At 16 I ventured one Sunday summer night out of the woods to a near by shopping plaza to go buy cigarettes at a 24 hour laundramat which had a machine. Everything was going well till I was walking back behind the plaza to head back to the woods when a local police car came around and the officer stopped me. He was wondering what a teenage girl was doing at dusk behind a shopping plaza. I was panicked by it all and surprised the officer, confessing that I really wasn’t a girl after all. He was really taken back. He told me to get my butt home right away which I did.”

Diana did not think that would be the end of it. She was convinced the officer would show up at their door to tell her mother about the incident. She decided to be pre-emptive.

“I finally got the nerve to pull my mom off to the side late that night and told her what had happened. She listened as I just let it all come out — the urge to dress, taking some of her clothes to the field, going to the mall and being confronted by the officer. It all came out in a rush. It must have been quite a shock for my mom but at the time she said very little.

“She called the police station and talked to the officer who was coming off his shift. She then came back and said that nothing more would happen and that she would talk more to me in the morning.”

Diana did not know what to expect as she spent a restless night thinking of what trouble she might be in.

“The next day my brothers and older sister were off to do their summer jobs and my younger sister was at day camp. My Mom sat me down and started to ask me questions about what I was feeling inside.

“I told her that I had this very strong desire to dress and be accepted as a girl. I told her I felt very awkward as a boy and did not feel I could relate to what I was supposed to like as a boy.

“By now my parent’s had separated and were heading for a divorce so Mom was having to deal with me on her own. She asked me if I thought I needed to see a therapist, but knowing the expense of that I said no. I told her I would get over this and that she should not worry…it would never happen again.

“She looked at me and I can still remember her saying, ‘You deserve to be happy and live your life in the way that makes you happy. It is different and will be filled with such challenges, but if it is what you think you want then you should go explore and then decide if it is really you or just something of a whim.

“With that she told me come with her in the car. We drove to our local K-mart. She took me around and bought me my own clothes from bras and panties to several skirts, jeans and tops. We then stopped at Sally’s Beauty Store for makeup.

“My head was spinning all day. I was part self conscious that people in the store would see that mom was buying these girly things for me and part with my head in a cloud knowing that mom was buying these girly things for me.

“When we arrived back home mom said that I could experiment when the others were not home and that if I needed any help to let her know.

“I was completely dumbstruck by this all…Sure I was relieved from one perspective but now also quite unsure what to expect going forward.”

Thanks to a one-in-a-million mother Diana was able to comfortably and without guilt explore her feelings of femininity and learning the secrets of living life as a girl.

“The bras were a 34B and padded and the skirts were just your ordinary denim and the tops were all prints with catchy verbiage of the day. I never went for the ‘drag queen’ look.  My older sister soon discovered what was going on between mon and me. She was a big help especially with my make up. I spent most of the first summer dressing at home and reading Glamor and Cosmo mags. The following summer I actually began to venture out.”

Her life changed in other ways, too.

“That was a small side benefit to all this for my mom and sis. Ours had been a very macho household. Our dad had set the example that men did not do housework or help with meals or dishes. As my Diana persona developed I became far more inclined, even as David, to work with the other women in the home. My brothers were not amused.

“But no, mom and sis never thought it a good idea that we go around town together with me as Diana.”

Did her mother wonder about Diana’s sexual orientation?

“The first discussion it really didn’t come up, but following talks it did and we went over the challenges and what little we knew of the subject. Mom went to the library and picked up some books and I contacted the local Gay and Lesbian association and found a counselor but did not actually go see her till I was 19. We had quite a few discussions about sex and I was able to be quite open about my attraction. I am not sure the counselor really understood but she listened and she did provide me some helpful information on things I did not know.

In school Diana found herself quite attracted to guys from an early age…not as a guy to guy but as Diana.

“I would fantasize quite often about being intimate with a boy and that finally led me to exploring…and I just knew it was right! My first boy was actually a young man. He was from the Philadelphia area and his family had a cottage near our town. It was the summer before I went away to college. I was out as Diana browsing through the K-mart. He approached me and asked me if I would like to have coffee with him. I agreed. The cup of coffee lead in to an early dinner date. We had a nice conversation and he seemed genuinely interested in me. We talked about sports and my track career. He had also run track in school and college. He told me about participating in big meets like the Penn Relays. When he asked me about my best events I had to fib a bit as the times David was running in the 880 and mile would have been close to the girl’s state records of that era.

“He asked me to go to a drive-in movie with him that evening. I agreed but said that I had to call my mom.

“Needless to say mom was concerned for my safety but typically did not want to prevent me from having an important learning experience. We devised a safety plan; as soon as I got to the drive-in I was to phone her to relay my date’s license number and then tell him how ‘my silly mother insists I do that.’ He was okay with that.

“I honestly don’t remember the movie but I will never forget the night. The movie had barely started when we began kissing. I was nervous about what he would do if he discovered my secret but I was too excited to stop. Also, from track team locker room talk I had learned that that if I used the ‘time of the month’ line my date would probably back off.

“Several times he put my hand on his lap and I pulled it away but not before I could feel that he was VERY aroused.

“Then I felt ‘what the heck; its now or never’. I gripped his zipper and opened his pants. He pulled out his penis. He moved the car seat back so I could get my head down on him. You will know the rest…
It didn’t last long and when it was over he became quiet and apologetic. We left without seeing much of the movie and I had him drop me off a little way from home. I never saw him again and to the best of my knowledge he never knew I was anyone but Diana.”

Did your mother say anything when you got home?

“I wasn’t surprised to see her still up but I was a bit taken aback by her continuing concern about my safety. In the ‘David’ part of my mind I was pretty confident I could have handled any situation. Mom was seeing me as Diana and she was not so confident. But as we talked about my date and how nice he was and how nice he treated me I think she came to realize that I had been careful and that this man had made me feel very good even if just for one night. She didn’t ask how ‘far’ we had gone but she knew.”

When you went to college did Diana come with you?

As my first year was spent in a dormitory Diana was put away. It was very frustrating in some ways but it also allowed me to develop relationships with girlfriends. In fact for a number of years I thought I might be over the Diana phase. I married and we raised a family. However whenever I went home Mom always found a time to ask about Diana. I guess she knew there would come a time when Diana would come back. Now I wish Mom were still here to meet her again.

Category: Transgender Body & Soul