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 Sydney Lovekiss

Click on Sydney’s portrait below to go to her Facebook page.  Click here to go to her website.


   I was born in Hollywood, CA in the fall of 1971.  Mt father was a struggling actor and my mother had literally moved out of the house of her 18th birthday.  Their marriage was a disaster and they eventually ended up separating.  During that separation my mother cheated on him and became pregnant with me but told her husband I was his.  I didn’t find out until I was 19 that he wasn’t my father.  They got divorced and later remarried.  Although, he didn’t do it at home, he was also a cocaine addict.  During the years that they were separated my mother committed welfare fraud.  She eventually was caught and rather than facing justice chose to run.  We spent several years living in a hotel in Hollywood hiding from the police.  During this time, we literally lost everything we owned.  My mother attempted suicide twice.

During the time they were divorced my mother was gone working during the day.  I was often left home alone.  I would frequently go into my sister’s room, go through her things and just hang out when I was home alone.  She had a white four poster bed with a lace canopy.  Tons of collectible dolls.  A toy kitchen that I loved to play with.  I would try on her clothes and just lay around in her room basking in the femininity.  Eventually they got remarried and I didn’t really have alone time like that anymore, plus we eventually lost all those things.  

As I went into my adolescent years, I wasn’t able to spend any femme time, but I never forgot it.  Even into my young adult years I was never really in a situation where I was alone enough to indulge my femme side.  I never really developed any masculine interests though, like sports, and many of the things I did enjoy were always viewed as somewhat feminine.  I was never viewed as gay, but I had a huge feminine side that was obvious to everyone who knew me.  Once, during college, I was cooking for a group of friends from church and my minister joked, “You know, you’re going to make someone a really good wife someday”.  I didn’t feel offended at all.  I said to myself, “I think I would like that”.  

I got married in my late 20’s and when I was thirty, we had our first child.  I got laid off two months later.  My wife had to either go back to work or take an unpaid leave of absence.  We mutually decided that I would stay home while she went back to work.  I loved it.  For a whole year I was basically a housewife.  I did all the cooking, cleaning, shopping and the laundry.  We never saw me as the woman in the relationship, but I definitely felt that I had stepped into that role in many ways.  I felt it was the best year of my life up until that point.  Eventually I started a business that allows me to be home full time.  My wife has since quit her job, 10 years now, and we are both home together.  Even though she doesn’t work, I still do most of the cooking, shopping, and the laundry.

During those years of being home alone again I would sometimes put on my wife’s clothes.  I loved how they felt but not how I looked I them.  For that reason, I didn’t do it a lot and I never left the house.  As years went on, I developed a growing desire to cross-dress to the point I would often lay awake at night unable to sleep, because I couldn’t stop thinking about it.  I had never shared the dressing with my wife.  I had always done it in secret when she wasn’t home, which wasn’t often.  I didn’t like all the sneaking around, and I knew I was never going to be able to dress the way I wanted to in secret.  So, one night while lying in bed I came out to her very casually.  I told her, “Sometime I think about dressing like a woman”.  She said she didn’t mind as long as I’m not going to start living as a woman full time.  I immediately jumped in with both feet.  I bought wigs, breast forms and other shape wear.  She took me to Wal-Mart and helped me pick out some foundation and other makeup that matched my skin tone.  She even helped me put it on.  I watched lots of online tutorials and practiced and experimented with different looks.

I started dressing at least twice a week and after a couple of months I stepped out for the first time.  I was scared, but it was wonderful.  Most people didn’t even notice me, so I assumed I was passing.  The few that did seem to notice I was a man didn’t seem to care.  I asked my wife to name me and she named me Sydney after the character Sydney Bristow from the television show Alias.  I made up the last name Lovekiss because I thought it sounded fun and I was the only Sydney Lovekiss, and I liked that.  I started spending time out as Sydney a couple time a week.  Sometimes my wife would meet me for lunch or something.  As I did, I realized that this was much more that “Cross-dressing”.  I realized that when I was Sydney that I wasn’t pretending to be a woman.  I was a woman.  There was a woman inside of me that I had kept bottled up and when I let her out, I felt free, SO FREE.  I don’t feel uncomfortable as a man, but I definitely need my Sydney time.  I have come to accept that I am a genderfluid / bi-gender person, and that is who I always have been.  I love the male roles that I have in life as husband and father, but I also love my female side.  Becoming Sydney has been one of the most wonderful experiences of my life.