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My Biggest "What If"

a cross dresser posing in a blouse, short skirt, suntan pantyhose, and high heelsI've found that one of the greatest benefits of sharing my story on the web is that it has allowed me to connect with other girls just like me. These girls share their stories, dreams, struggles, fantasies, pictures, etc. with me, and it has solidified the feeling that I've always had: there has to be at least a million people out there just like me. And while we all take our cross dressing activities to different extents, I believe we are mostly of the same mind.

I believe it is a common practice for most of us girls to lie awake in bed and review our lives both past and present with regards to our cross dressing and ask that eternal question "what if?".  Nearly every night as I fall asleep, I think of opportunities missed or ways that I could have done something different or new strategies that I can implement now in order to take my cross dressing to a new level, and then I inevitably drift off asleep with some sort of cross dressing fantasy on my mind.

Every year at the end of April, I can't help but to recall the biggest "what if" of my life as a cross dresser. This is a true story that happened to me exactly 16 years ago and could have changed my cross dressing life forever.

Just before my senior year in college, I was working at the department store that I mention in other places in my diary. A few weeks before the fall semester began, I was at work one day when in walked a girl from my home town who was just about to begin her freshmen year at the same college. I knew this girl quite well growing up as several of our social circles crossed paths and since we attended the same schools. And though we attended the same schools, we never attended junior high school or high school together since she was three grade levels below me. Due to this difference in ages, you could say our relationship was more along the lines of older brother and younger sister. She was an extremely cute girl growing up, but she was just young enough that it wouldn't have been appropriate for the two of us to go out.

But now as we stood face to face together for the first time in three or four years in that department store, I felt an immediate attraction to her, and the feeling from her was reciprocated. Sometimes you can just tell, and this was one of those times. The one roadblock to our beginning a romantic relationship, however, was that I had a serious girlfriend at the time. This is the same girlfriend that I mention on my history page who went home for the summer and left some of her dresses and boxes in my closet for what she thought was safekeeping. I had been dating her for most of the previous year, and I even took a week off of work during the summer so I could fly to her home and meet her parents. We hadn't arranged to live with each other our final year of school, but the relationship was heading in that direction quickly.

So in the midst of this situation, a darling girl who I knew from my hometown walks in, and I am immediately attracted to her. This girl, whom I will call Amy, knew about my girlfriend as she had asked around in an effort to locate me, and in the process she found out that I was in a serious relationship. Still, we knew each other from way back; she was a new girl in a new town; I had a car and she didn't; so it was natural for us to associate with each other in an asexual way, the same as we had always done growing up. I took Amy grocery shopping, and we visited several sites in town together, and she'd make me dinner, and we'd go to the movies together all the while knowing that I was in another relationship with a girl who would be arriving back in town just before the start of school. Looking back, it was such an interesting dynamic because we were obviously both attracted to each other, but she was intent on not breaking my girlfriend and I up, and all through my life I have been completely loyal to my partners, and this time was no different.

Amy and I continued this strange association for four or five weeks until the beginning of September when my girlfriend flew back into town just before school started. She already knew about Amy because on one occasion when Amy was making dinner for me at my apartment, my girlfriend called and Amy answered the phone (this was still in that day and age before the internet and cell phones). I was completely up front and honest with my girlfriend, but I knew she didn't like the situation, and I can't blame her at all.

After school started, I saw Amy less and less due to my girlfriend being back in town and occupying much of my time coupled with the rigors of a full class schedule. Amy still reached out to me when she needed a ride or needed help with something, but our contact was limited to several times a month. In early October, Amy called me up one day and said that she had a boyfriend. This didn't surprise me at all because she was so cute, and with her meeting all those new guys in her classes, it was just a matter of time. I never went out on a double date with Amy and her new boyfriend, but I did meet him on occasion, and we had quite a bit in common and became pretty good friends considering the strange dynamic in place.

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My Crossdressing Relections

My Cinderella Story

Autumn Photo Shoot

Mommy memoirs from the ballpark

Psychological need for bras

Crazy night at the ballpark

In the mood for pink

Long overdue photo shoot

A girl and a flower garden

Signs of a Girl

Challenges of being a girl 24/7

Quiet Picnic as a Girl

Why My Bra and Panties Rarely Match

Dimensions of being a girl

Pantyhose here and there

Connecting with my cross dressing roots

My slip is showing

Crossdressing and Halloween

Sunday Morning Walks in a Dress



My Biggest "What If?"

Mornings as a Girl

My Mother and My Crossdressing

Motherly Feelings While Crossdressed

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