Memoirs of a Crossdresser                by: Alyssa Davis

 

I'm not sure when it started. My earliest recollection was at about age 7. Sarah, my sister, who was then 9, and I commonly played together when there was little else to do.

We did get along very well, even then. The usual board games kids play, occasionally toys or doll play which upgraded to tea parties, and they evolved into dress-up tea parties. She was always the "mama" and I played either the "papa" or the "son" depending on what she chose to wear. Eventually, that got boring…too much like reality… so, for variety, we tried a "ladies" party with me obviously being the other lady. I didn’t care. It was harmless and a lot of fun. Just some old dresses and jewelry of mom’s to begin with, then adding more things for realism such as scarves, shoes, hose. Sarah considered it a real challenge to make me into a "proper lady," and I didn't mind it one bit because I admired the pretty clothing ladies wore and actually had wanted an excuse to try things on. I remember the first time she put me a girdle with garters, bra and hose. A feeling evolved within me that I cant describe! A long, silky, slip with string straps convinced me, this was for ME…I loved it! It was like a long gown on my small body. I wanted more.

Becoming my favorite activity, this went on for a long time. If she didn’t suggest it, I would ask to be dressed. We outgrew the tea parties and progressed to Sarah making me her personal "Barbie Doll" having me model her clothes in different combinations, complete from lingerie to shoes. I willingly submitted to her doing that to me because I loved it, she enjoyed dressing me, and as a fringe benefit to me, I was learning how to properly select and wear girl’s clothes and makeup, something I had developed a strong interest in. Sarah, in turn, coached me in female mannerisms.

Mom frequently saw us at "play" and didn't seem to mind either, as long as I didn't complain, it didn’t matter to her. Complain? I’d have begged to do it! And, it kept us occupied and not bothering her.

One Saturday afternoon, when Sarah, now a teenager, asked mom if she could join her friends and go to a movie, mom replied,

"Yes, if you take your brother with you. I don't want to leave him home alone."

"But mom, I'm going with my girlfriends...he'll be the only boy. They wont like that. They'll go without me if he has to tag along," Sarah whined.

"I don't care, Sarah...you'll have to work it out. I have several errands to run, I cant bring him, and I wont leave him home alone."

I was 13 at the time…I could’ve stayed home. I didn’t know why she felt otherwise.

Sarah anguished for a while, then quietly asked me if I'd consider dressing up and going as a girl, maybe a "cousin", since she'd dressed me so many times while we were playing, and she knew how good I looked, I think she was sure I wouldn't say no.

"But Sarah, I've never worn your clothes outside the house. What if someone recognizes me as a boy?"

I had to offer some resistance for effect. The idea excited me very much.

"No one will recognize you...I promise. You can easily look like a real girl. Are you willing to try? Please?" she begged.

She was really desperate to be with her friends. Thinking it might be fun, I agreed, I did enjoy wearing her things and had become totally comfortable in them. So she told mom about her plan and asked mom for help.

"Well, I have noticed you two playing as girls many times, and I've seen you, Alan, completely dressed in Sarah's things and they fit you very well. You're kind'a cute too. Are you really willing to do this for your sister? I know she's desperate to go with her friends to see that movie."

"Sure mom," I said, "it might be fun. I hope her friends don't find out, get angry, and send us both home."

So, Mom and Sarah went to work on me and transformed me into a girl. Wearing Sarah's clothes, a touch of lipstick to look more convincing, and my longish hair brushed and styled effeminately, I became passable as a 15 year old girl. Of course, at that early age, that wasn't much of a challenge. This time I looked better than I ever had before, and to my own surprise, I really liked what I saw in the mirror, especially since I looked older, in fact more like Sarah's twin.

"My gosh, Sarah, you have a twin sister," Mom exclaimed. She was amazed that I was so willing to do this. Willing...I was delighted, but I didn't admit it.

"Wow, Mom...you're right," as she looked at me from different angles.

I had never been so completely dressed. Panties, padded bra, full slip, hosiery, skirt, yes, but now with my hair done, lipstick, nail polish.

"Alan, you're beautiful. I think I'll call you Alana."

I didn't care what she called me...maybe I should've been embarrassed or at least uncomfortable as any boy would dressed like this, but I wasn't. I felt so good about looking like this and about what we were going to do. In my mind, I was a real girl!

"OK Alana, so here’s the story. You're supposed to be my cousin so don't spoil it for me or my friends will never speak to me again. All right? If they ask, you live across town and don't visit very often."

I promised to cooperate. I wanted to see the movie anyway, and I especially enjoyed the gender swap. As planned, I was introduced as Sarah's cousin, from another part of town, and generally acted as a shy young lady with good manners. From all the times we had played together as two ladies, I had learned how to act, and I patterned my behavior after the other girls...after all, they were my peers and role models. In turn, they were all friendly towards me and welcomed me as their new friend. We had such a good time together that I was invited to join them again at future outings of which I readily agreed to do. Even Sarah was very pleased at my behavior, my acceptance by her friends, and my willingness to do it again. She had never seen me so friendly and high spirited in a group and having so much fun. I was no longer an abhorrent little brother, something she fashionably grew to consider me to be when I, as Alan, was with her friends. Of course, when we were alone, I was her imaginary "sister." She reported back to mom, and mom was surprised and pleased. I guess being in the role of a girl did that to me. It was a side of me that no one had ever seen. I was another person, a nicer person.

"Alan, do you really enjoy being a girl? I heard you had a lot of fun with the other girls," Mom asked. "As a boy, you always made a pest of yourself with Sarah’s friends, but now I only hear good things."

"Oh yes, Mom, it was fun! I loved wearing Sarah's things in public," I admitted modestly, "And I was treated very nicely by the girls since they believed I was a real girl too. This was a lot more fun than going out with my boyfriends. They usually always want to get into trouble. I even told the girls I 'd join them again."

"Well, it looks like Sarah's "cousin" is going to be visiting us more often," Mom said, smiling and winking.

That was the beginning of my real public crossdressing experience. What began as a simple hoax, grew into more serious happenings. After that first movie afternoon, Alana was invited to a birthday party with Sarah’s friends where she was immediately accepted by the other girl's mother... then occasional all-girl shopping expeditions, and more parties. They insisted that Alana accompany Sarah. Everyone accepted Alana as her feminine personality evolved into a perfect lady..

Sarah continued to be very helpful with seriously showing me how to behave like a young lady in different situations and dress in her clothes until I was able to pick my own outfits perfectly. At first, Mom assumed I was only doing this as a favor to my sister so as not to let her get caught in the lie she had concocted, but eventually she realized that I seriously enjoyed being a girl, especially when I started to wear some of Sarah's things and makeup routinely around the house.

Mom consented to letting me wear my hair even longer… shoulder length. It looked better when I dressed as Alana and saved her money for haircuts. Sarah wore her hair the same length and we practiced doing various hairstyles on each other. I got very good at it. She treated me as her real sister, and I played the part well and loved it. Mom eventually bought me my own lingerie so I could stop wearing Sarah's. She came to accept my crossdressing as I wore girl's clothes more often than my boy things. I went for an androgynous look. Mostly jeans and tops, but always girl's underwear including a bra which made me feel more feminine and kept everyone guessing . I liked to have a little bosom showing in the front and straps slightly visible in the back.

Mom frequently took her two girls out shopping or to dinner where we had a wonderful time. Our whole relationship changed. Alan had never experienced this. Dad was gone so much, either he didn't know or didn't care.

By the time we were in our late-teens, I had learned how to look and act as naturally feminine as Sarah, and had mastered the application of cosmetics and hair styling. We wore each other's clothes at random and routinely. Being physically small for a boy, we remained the same size so her things fit me perfectly. Except, she was able to wear mine openly to school while I could only be Alana on special occasions. As Alan, my hair was kept in a ponytail as many boys wore theirs, but Alana wore hers in a variety of feminine styles which I created for her. A few of Sarah's closest friends knew about Alan and still accepted me as the girl I could become. I was brought into their confidence and trust and even invited to slumber parties. I preferred the company of girls, socially, more than that of boys, that is, I preferred to be Alana more than Alan. I desperately wanted to be a real girl.

I had a few male friends as Alan, but we had so little in common, the friendships were very casual. I was more of a scholastic type and maintained good grades, but had no interest in sports or other typically male activities. As long as my grades were good, my parents didn't care what I did. My real interests were more into things such as women’s clothing, hairstyles, makeup, and domestic things. And music. I loved music.

At one of the slumber parties, I (Alana) was dared to date a boy. Sitting there in lace trimmed, "baby doll" pajamas, with my shoulder length, well styled hair, looking every bit as feminine as the real girls, (and feeling it), they teased me until I accepted the dare. I was set up for a blind date with a boy, a senior from a different high school. At that time I was a junior.

I was confident that I could pull it off. With Sarah's assist, I dressed for the event. I wore my padded bra, panty girdle to conceal any unexpected "growth", pantyhose, a long full skirt, and a form fitting sweater. My hair styled into a French braid, I wore full makeup, but lightly applied. I had on a gold necklace and matching dangling earrings (my ears had been pierced years earlier). I knew I was beautiful.

My date arrived at the prescribed time, and introduced himself. He was very handsome.

"Hi Alana, I'm Bill."

"Hi Bill...well I guess you already know my name," I said in my effeminate manner, something I'd learned to do as my voice started to change. I could make it sound sultry and sexy.

I behaved as a perfectly well mannered lady. We went to dinner, then a movie where I allowed Bill to put his arm around me. I was completely at ease with him and felt like a natural woman out with her boyfriend. After the show, he took me straight home where we sat for a while and talked before he walked me to the door. I did a lot of listening, as a lady should, and bolstered his ego whenever possible by asking him questions. Thing's I had learned from my hours of feminine training. We kissed goodnight, at first a light kiss, then another more passionate, and I went in. It all felt so right. I completely put out of my mind that I was a boy and I returned his kiss without guilt. I secretly hoped he'd call again. Was I gay? I don't think so. Feeling every bit like a woman, I naturally acted as one. I felt good about being with a handsome young man as any woman would, and at that moment, I was a woman.

I had to report back to the girls in the group about my date. I told them everything.

"Did he kiss you?"

"Yes." Silence.

"Did you kiss him back?"

"Yes" More silence.

"Did you enjoy it?"

"Yes," I confessed, rolling my eyes to their squeals of delight.

"Did he do anything else?" they pumped with expectations.

"NO! He was a perfect gentleman," I replied, to their disappointment.

"Do you want to see him again?"

I was afraid they'd ask that question. What could I say? I didn't want to lie.

"I think so, yes. If he calls me, I'd go out with him again," I admitted.

They all screamed again and hugged me.

The group was very proud of me for going through with the date. They were so sure I'd back out. It just brought me closer into the circle of my girlfriends. I was one of them now...all sisters. Where I wanted to be. Where I felt I belonged.

Bill did call again, and we dated a few more times. We had a few heavy petting sessions which I enjoyed, yet he never found out I was a genetic male. I enjoyed his kisses but I was very careful where he put his hands though I wasn’t so careful where I put mine. I didn't consider myself a man, but I didn’t forget I was a male. He was the only boy I ever dated but I could have easily fallen in love with him. I felt a strong physical attraction.

Sarah and I had developed a very close relationship. We continued to play the brother-sister/sister-sister role until I graduated high school. Sarah went away to college, our group of girls split up and each went her own way except for Barb, one of our friends who knew the truth about Alana. She and I continued to see each other and grew very close. We became like sisters; she fully approved of Alana, and eventually we became lovers. We rented an apartment and lived together while I went to school to become a fashion photographer and designer. She studied to be a model. I spent all of my time either dressed as a woman or at least, androgynous. Either way, I always passed as a woman...I had gotten too effeminate to be taken for a man any longer, especially since I had electrolysis for my beard and body hair and ultimately, breast implants. It was good for my career since I worked with women models all day long in various stages of undress where a man would be out of place. In fact, I had pretty much forgotten how to be manly.

Barb and I were married in a small civil ceremony since my parents didn't want their social circles to know about me. When asked, they said I had left the country. Barb and I are very happy with our lifestyle. She only wants what makes me happy, and I'm happy living as Alana.

I built up a reputation as a successful woman photographer in the fashion industry working with top models. It’s a real asset to have access to them in their dressing rooms for setup and last minute details.

Sarah and I stay in touch. We'll always be sisters. It was my decision and I blame no one. In fact. I thank Sarah for our "tea parties". I believe it was my destiny to be transgendered...I certainly am happy.

 

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