I guess it all started as it has for most of us - sneaking into the hamper to get some of mom's things to put on when I was a kid.  I never really understood why I liked it, but I just knew it felt good.  I kept it to myself and would dress only when I was sure I would be alone for a few hours.  But even then, I would only do it occasionally.  More or less when the mood struck me, and the opportunity presented itself.  This pattern continued through my high school years until I graduated and moved on to college.

     For the first year of college, I basically put my desire to dress on the shelf. Living in the dorms and having a roommate made it pretty much impossible anyway.  But in my Freshman year, I began dating a girl that was about to change everything for me.  My girlfriend and I were dating for a few months, and were getting pretty close.  She was a senior, and had her own apartment, so I was spending alot less time at the dorm.

     She was a member of a sorority.  One Halloween, they had a party at the sorority house.  My girlfriend put the proposition to me that we go dressed as the opposite sex.  I was a little nervous about it, but given my love of dressing anyway, I could not pass this up. On the day of the party, we spent most of that afternoon getting me ready.  We were fairly close in size, so picking out an outfit was not really a problem.  I'm only 5'6", and in fairly good shape.  

     We picked out a nice little leather mini skirt, an angora sweater, some thigh-high stockings with garter, and padded up the bra.  To show her what a good sport I was about the whole thing, I even shaved my legs!  (Not that I had much hair on them to shave anyway.)  I had always worn my hair very long back then anyway, so I didn't even need a wig.  She just styled my hair and did my makeup.  I must say, I did look very good.  And she looked really cute dressed as a man, with a little eyebrow pencil mustache and everything.

     The party went well.  My girlfriend did such a good job on me, I was receiving alot of complements.  I was also receiving some pretty strange looks from some of the guys that were there.  Maybe I looked a little too good.  But, I didn't care.  I was loving all the attention!  We had a really good time.  After the party, we went back to her place.  I started to get undressed, and my girlfriend told me not to.  She said that she was extremely turned on by the way I looked in her outfit.  Without going into all the details, we had an amazing night.

     We both enjoyed it so much, that my dressing became part of our relationship.  She had told me that she found it very sexy that I was willing to dress and show a side of me to her that no one else was able to see.  She also awakened in me the realization that this was more to me than just sneaking on some underwear when my mom wasn't home.

     Unfortunately, at the end of that year, she graduated and we eventually lost touch.  Throughout the rest of my college years, I was forced to hide my desires again, never having found a girlfriend as "open-minded" as she was.  Plus, either sharing a dorm room or an apartment with friends made privacy a very rare commodity.  I finally graduated, and began my life after school.