Crossdressing Storieslatest

My First Real Kiss

My first kiss with a crossdresserWhen I was in high school I was a bit socially awkward and especially around girls. I’d been with a number of girls, sure, but many of them left a lot to be desired. One year, a new family moved into my parent’s building and my life changed. That was because within that family, there was a very effeminate young male that I found on the back porch in total drag.

I was just coming upstairs from track practice when I noticed him. I was immediately struck by how beautiful he was in girls clothes and makeup. He was Puerto Rican descent and had full sensual lips that were even more enticing by the matte cranberry red lipstick.

I was frozen when I saw him. When he saw me, he looked horrified and backed into a corner thinking that I was going to wail on him. I assured him that he was safe and contrary to his fears, I actually thought he was really cute. The words just came out of nowhere because I was so smitten.

We wound up sitting on the back porch steps talking well into the night. And it was obvious that we had a mutual attraction for one another. We decided to slip into the basement stairwell of a vacant apartment in the building so that we could talk more freely which led to hand holding, which then led to the moment where I leaned in to kiss him. That led to another kiss, then another, then another, then more prolonged kissing and caressing. The next thing I knew, he was sitting on my lap while we continued kissing.

Knowing that our families would wonder where we were, we reluctantly decided to part and head back to our apartments. But this felt too good to abandon so we would meet regularly at the basement stairwell where we would kiss for hours. The level of intimacy was unmatchable and no girl in the neighborhood could even come close to what I experienced with this cross dresser. Every night I would rush from the dinner table just to meet up so that we could share those sensual kisses.

Unfortunately, I went away to college and when I returned that fall, I was told that this family had moved to California after the father of the family found a job there. This was before email and social media, so we never got a chance to reconnect.

I did find some consolation in the fact that one of our neighbors talked about how the son in the family cried the whole time he was leaving. I could have been wrong, but I was hoping that those tears were because we would not be together again.

Sorry if this story does not end in this cross dresser and I fully making love, but our kissing sessions were filled with the most sensuality that I’d ever experienced and something that will always hold a special place in my heart.

Submitted by Jay Top

Facebook Comments


  1. No “happy ending,” but a beautiful memory nonetheless.

  2. No “happy ending,” sadly. But it’s a beautiful memory.

  3. What a beautiful story and sad 😢, I had the same sort of thing happen to myself when I lived in Exmouth Australia and John went back to the United States. I have kicked myself ever since for not being truthful to my feelings.

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