Memoirs of a Crossdresser - A story of a Crossdresser 💕💕👗

Memoirs of a Crossdresser 

I'm not sure when i began to Crossdressing. My first remembrance was around the age of seven When i was Crossdressing. Sarah, my 9-year-old sister, and I used to play together when we had nothing better to do.

Even back then, we got along great. The typical board games that youngsters play, occasionally toys or doll play that grew into tea parties, and then into Crossdress in tea parties. She was always the "mama," and depending on what she wore, I was either the "papa" or the "son." That eventually became tedious...too much like reality... So, for a change of pace, we tried a "ladies" party, with me as the other lady. 

I didn't mind. It was completely innocuous and a lot of fun. To begin, I used some of my mother's old gowns and jewelry, then added other items for realism such as scarves, shoes, and hose. Sarah thought it would be a tremendous challenge to turn me into a "proper lady," and I didn't mind one bit because I liked the gorgeous clothes females wore and had wished for an opportunity to try them on. I recall the first time mother put on a girdle with garters, bra, and stockings for me. I had an emotion that I cannot describe! A long, silky slip with string straps persuaded me that this was for ME...It was fantastic! It seemed like a lengthy gown on my petite frame. I desired more.

This became my favorite activity and lasted a long time. I'd beg to be dressed if she hadn't suggested it. We outgrown the tea parties and Sarah turned me into her personal "Barbie Doll," having me model her outfits in various combinations, from lingerie to shoes. I happily agreed to her doing it because I enjoyed it, she enjoyed dressing me, and as a side bonus, I was learning how to correctly pick and apply girl's clothes and makeup, which I had acquired a keen interest in. Sarah, in turn, instructed me in female manner.

Mom saw us at "play" all the time and didn't seem to object; as long as I didn't complain, it didn't matter to her. Complain? I would have urged you to do it! It also kept us engaged and kept us from disturbing her.

When Sarah, now a teenager, asked her mother whether she could go to the movies with her friends one Saturday afternoon, she was told, "Yes, if you bring your brother." I don't want to leave him at home by himself."

"But, Mom, I'll be there with my girlfriends...he'll be the only boy." That will irritate them. If he needs to accompany them, they'll depart without me," Sarah grumbled.

"I don't care, Sarah...you'll have to figure it out on your own."

Mom saw us at "play" all the time and didn't seem to object; as long as I didn't complain, it didn't matter to her. Complain? I would have urged you to do it! It also kept us engaged and kept us from disturbing her.

When Sarah, now a teenager, asked her mother whether she could go to the movies with her friends one Saturday afternoon, she was told, "Yes, if you bring your brother." I don't want to leave him at home by himself."

"But, Mom, I'll be there with my girlfriends...he'll be the only boy." That will irritate them. If he needs to accompany them, they'll depart without me," Sarah grumbled.

"I don't care, Sarah...you'll have to figure it out on your own."

You can easily pass for a real girl. Are you willing to give it a shot? "Please?" she pleaded.

She was keen to spend time with her buddies. I consented because I enjoyed wearing her clothes and had grown quite comfortable in them. So she told her mother about her plan and requested for her mother's assistance.

"Well, I've seen you two playing as girls a lot, and I've seen you, Alan, completely dressed in Sarah's clothes, and they fit you perfectly." You're also rather attractive. Are you sure you want to do this for your sister? I know she's dying to see the movie with her buddies."

"Sure, mom," I replied, "it could be fun." 

"I'm hoping her friends don't find out, become enraged, and send us both home."

So Mom and Sarah set to work transforming me into a girl. I passed for a 15-year-old girl by wearing Sarah's clothes, a bit of lipstick to look more convincing, and my longish hair brushed and styled effeminately. Of course, that wasn't much of a challenge at that age. This time, I looked better than I had in a long time, and to my surprise, I liked what I saw in the mirror, especially since I appeared older, more like Sarah's twin.

"My gosh, Sarah, you have a twin sister," Mom said. She was astounded that I was so eager to accomplish this. Willing...I was overjoyed, but I didn't say anything.

"Wow, Mom...you're right," she said as she stared at me from various angles.

I had never been that well-dressed. Yes, I'm wearing panties, a padded bra, a full slip, hosiery, and a skirt, but now I'm wearing lipstick and nail polish.

"Alan, you're stunning. "I believe I'll call you Alana."

I didn't care what she called me...I shouldn't have been embarrassed or even uncomfortable dressed like this, as any male would be, but I wasn't. I felt great about how I looked and what we were going to do. In my mind, I was a proper lady!

"All right, Alana, here's the story. Don't ruin everything for me because you're meant to be my cousin, or my pals will never speak to me again. Is that correct? If they inquire, you reside across town and rarely come."

I pledged to assist. I still wanted to see the movie, and I particularly appreciated the gender switch. As planned, I introduced myself as Sarah's cousin from another part of town and pretended to be a bashful young girl with good manners. I had learned how to act from all the times we had played together as two ladies, and I modeled my behavior after the other girls...after all, they were my classmates and role models. 

In turn, they were all friendly and welcomed me as a new friend. We had so much fun together that I was requested to join them on subsequent outings, which I gladly accepted. Sarah was delighted with my actions, her acceptance by her friends, and my willingness to do it again. She had never seen me in a group so welcoming and upbeat, or having so much fun. I was no longer an odious little brother, as she had grown to regard me as when I, as Alan, was among her friends. Of course, when we were alone, I pretended to be her "sister." Mom was shocked and happy when she reported back.

I guess playing a female character did that to me. Nobody had ever seen this side of me before. I was someone else, a kinder person.

"Alan, do you like being a girl?" "I heard you had a great time with the other girls," Mom inquired. "As a boy, you were always making a nuisance of yourself with Sarah's friends, but now I only hear good things about you."

"Oh, Mom, it was great fun!" "I enjoyed wearing Sarah's clothes out in public," I said modestly. "And the girls treated me very nicely because they thought I was a real girl as well." This was far more enjoyable than going out with my boyfriends. 

They are continuously looking for ways to get into trouble. I even promised the girls that I'd return."

"Well, it appears that Sarah's "cousin" will be visiting us more frequently," Mom added, smiling and winking.

That was the start of my genuine public crossdressing adventure. What began as a simple hoax evolved into more serious events. After that first movie afternoon, Alana was asked to Sarah's friends' birthday party, where she was immediately embraced by the other girl's mother... then infrequent all-girl shopping outings and other parties. Alana was required to accompany Sarah. Alana was accepted by everyone as her feminine demeanor developed into a lovely lady.

Sarah continued to be quite helpful in showing me how to behave like a young lady in various settings and dress in her clothes until I was able to pick my own outfits correctly. Mom initially felt I was only doing this to help my sister from being caught up in the lie she had devised, but she soon realized I really enjoyed being a girl, especially when I began to wear some of Sarah's clothes and cosmetics about the home on a regular basis.

Mom agreed to let me wear my hair longer... shoulder length. It looked better when I dressed as Alana and saved money for haircuts for her. Sarah wore her hair in the same length as mine, and we practiced different hairstyles on each other. I grew rather excellent at it. She treated me as if I were her genuine sister, and I enjoyed playing the part. Mom eventually got me my own lingerie so I wouldn't have to rely on Sarah's. She eventually accepted my crossdressing because I wore girl's clothes more often than guy clothes. I chose an androgynous style. I mostly wore trousers and blouses, but I always wore girl's underwear, including a bra, which made me feel more feminine and kept everyone guessing.

I enjoyed having a little bosom showing in the front and straps showing in the back.

Mom frequently took her two daughters shopping or out to dinner, where we had a great time. Our entire connection shifted. Alan had never encountered anything like this. Dad had been gone so long that he either didn't know or didn't care.

I had learned how to look and act as naturally feminine as Sarah by the time we were in our late teens, and I had mastered the application of cosmetics and hair style. We donned each other's outfits at random and on a regular basis. We stayed the same size despite being physically little for a male, thus her clothes fit me well. Except she could openly wear mine to school, whereas I could only be Alana on rare occasions. As Alan, I wore my hair in a ponytail, as many boys do, but Alana wore hers in a variety of feminine styles that I designed for her. Sarah's closest friends were aware of Alan but still embraced me as the girl I could become.

I was put in their good graces and even invited to slumber parties. Socially, I preferred the company of girls over that of boys; that is, I liked to be Alana rather than Alan. I wished I could be a real girl.

As Alan, I had a few male acquaintances, but we had so little in common that our friendships were quite casual. I was a scholastic type who had decent marks but had no interest in sports or other traditionally manly hobbies. My parents didn't care what I did as long as I got excellent grades. My true interests were in women's clothing, haircuts, makeup, and domestic matters. There's also music. I was a big fan of music.

I (Alana) was dared to date a boy at one of the slumber parties. They taunted me until I took the dare, dressed in lace-trimmed "baby doll" pajamas and with shoulder-length, well-styled hair, appearing every bit as feminine as the actual girls (and feeling it). I was set up on a blind date with a senior from another high school. I was a junior at the time.

I was certain I could pull it off. I dressed for the occasion with the help of Sarah. I donned a padded bra, a panty girdle to cover any unexpected "growth", pantyhose, a long full skirt, and a form fitting sweater. 

I wore full makeup but applied it lightly and wore my hair in a French braid. I was wearing a gold necklace and dangling earrings (my ears having been pierced years before). I knew I was stunning.

My date showed up at the appointed hour and introduced himself. He was quite attractive.

"Hello, my name is Bill."

"Hi Bill...well, I guess you already know my name," I said effeminately, as I'd learned to do as my voice changed. I could make it sound sensual and seductive.

I carried myself like a proper lady. We went out to supper, then to the movies, where I let Bill put his arm around me. I felt perfectly comfortable with him and like a natural woman out with her partner. He drove me straight home after the show, where we sat and talked for a while before he escorted me to the door. I did a lot of listening, as a lady should, and boosted his ego by asking him questions whenever feasible. Things I'd learned from my hours of feminine education. We kissed goodnight, first lightly, then more passionately, and I went in. Everything felt so right.

I absolutely forgot I was a male and reciprocated his kiss without hesitation. I hoped he would call again. Was I homosexual? No, I don't believe so. I naturally acted like a woman because I felt like one. I felt as wonderful about being with an attractive young man as any woman would, and I was a woman at the time.

I had to tell the girls in the group about my date. Everything was shown to them.

"Did he ever kiss you?"

"Yes." There was silence.

"Did you give him a kiss back?"

"Yes" There is more silence.

"Did you enjoy it?"

"Yes," I admitted, rolling my eyes at their delight.

"Did he do anything else?" they wondered, their hopes high.

"NO! To their dismay, I said, "He was a perfect gentleman."

"Do you want to go see him again?"

I was scared they'd ask me that. What could I possibly say? I didn't want to tell a falsehood.

"I believe so. "I'd go out with him again if he called," I said.

They all screamed once more and hugged me.

The gang was quite pleased of me for following through on the date. They were convinced I'd back out. It merely moved me closer to my girlfriends' group. I was now one of them...all sisters. That's where I wanted to be. Where I felt at home.

Bill called again, and we went on a couple more dates. We had a couple intense petting sessions that I enjoyed, but he never discovered I was a genetic man. I appreciated his kisses, but I was cautious about where he put his hands, whereas I wasn't so cautious about where I put mine. I didn't consider myself a man, but I never forgot who I was. He was the only boy I had ever dated, and I could easily have fallen in love with him. I had a strong physical attraction to her.

Sarah and I had become very close friends. We played the brother-sister/sister-sister role until I graduated from high school. 

Sarah left for college, and our group of females split up, with the exception of Barb, one of our friends who knew the truth about Alana. She and I kept seeing each other and became quite close. We became like sisters; she adored Alana, and we finally fell in love. We shared an apartment while I attended school to become a fashion photographer and designer. She trained as a model. I spent the majority of my time dressing as a lady or androgynous. In any case, I was usually mistaken for a woman...

I'd become too effeminate to be mistaken for a guy, especially since I'd undergone electrolysis for my beard and body hair and, eventually, breast implants. It was beneficial to my profession because I worked with female models all day in various degrees of undress where a man would be out of place. In fact, I'd almost lost how to be a guy.

Barb and I married in a tiny civil ceremony since my parents didn't want their social circles to be aware of my existence. When I was questioned, they stated that I had fled the country. Barb and I are really pleased with our way of life. She simply wants what makes me happy, and I'm content with my life as Alana.

Working with prominent models, I established a reputation as a successful female fashion photographer. Having access to them in their dressing rooms for setup and last-minute details is a huge benefit.

Sarah and I maintain contact. We're sisters for life. It was my decision, and I hold no one responsible. In reality, I'm grateful to Sarah for our "tea parties." I believe it was fate for me to be transsexual...I am certainly pleased.