I read a confession under My Family about a boy who has been dressing like a girl for several years and that prompted me to post this here.

Last year I was introduced to a girl named Mandy at a company Christmas party. She was petite, with dark hair and HUGE eyes. Being geeks, we hit it off talking about Comicon, SXSW, and MMRPG we played. One thing led to another and we ended up leaving early and making out in my car. I dropped her off at her house (tried to get in, but was politely rebuffed) and we exchanged numbers.

After the holidays I hit her up for coffee after work. She was game so we hit the Bucks and had a couple frozen buzz builders, then went walking downtown around the Old Port area. It was getting late, so I suggested dinner - my treat - and we ended up at a local brew pub I like. A couple beers and burgers later I walked her back to her place and kissed her on her front stoop. Nothing radical, just a delicate kiss.

I don't know if it was the beer, or the way I kissed her, but she suddenly asked if I wanted to come up for a night cap. Who was I to say no?? Her apartment was small and very conservative, very well decorated in a feminine sort of way. We sat in the living room and channel surfed for a bit while sipping on some Mike's Hard Lemonades over crushed ice.

After a bit we started making out and my hands began moving up and down her sides until I worked up enough courage to handle her breasts. They were small, but very puffy and she was extremely sensitive. When I tried to move lower she told me her Aunt Flo was visiting, but that she didn't want me to leave with blue balls on her account. She was no beginner at blowjobs, and worked my cock with complete concentration until I exploded. Mindy wasn't much for swallowing, but she jacked me off all over her face and blouse and made sure I was really empty before excusing herself to the bathroom to cleanup.

I texted her over the next couple days trying to setup another date, but she didn't return any. This worried me, as I felt like maybe I'd pushed things too fast and didn't want her to think I was just some a-hole looking for a FWB situation. I actually liked her, we got along well, and I had hoped she liked me. I ended up tracking her down using the company directory and went to her cubicle.

She was a bit embarrassed to see me there and asked me to meet her after work. It seemed weird. Like she didn't want anyone to know that I knew her, much less that we were together. Feeling a bit let down and cautious I met her back at that Starbucks that night after work. She apologized for ignoring my calls and text and being a spaz at work. Then went on to tell me she liked me, but that we could never see each other again.

I figured it was something I did, so I apologized for my behavior. Told her if I had gone too fast I was sorry and we could certainly slow down and start over. She broke into tears and ran out of the coffee shop - talk about totally embarrassing, the baristas looked at me like I was some kind of dirt bag for making her cry. The next day I sent her a couple yellow roses with a card again apologizing and telling her if she would give me another chance I would make up for whatever I had done.

Maybe two weeks go by before I run into her at a meeting. We end up sitting directly across from each other and through the 2hrs of BS I keep catching her looking up through her bangs at me. Once the meeting was over I hung back and asked her point blank - what did I do?? I never meant to hurt her, and was willing to make up for it if she would just tell me what I had done wrong. That's when she lays it on me that it wasn't me, but her. That she liked me and was afraid I would dump her, or worse when I found out her secret.

I had no idea what could possibly be such a big, bad secret that I would dump her "or worse" (whatever that might be??) if I ever found out. So I closed the door to the meeting room and asked her straight out - tell me your secret. If it's so bad we can't deal with it we just stay broken up. So she opens up and tells me she was born a boy, but had thought of herself as a girl ever since she was 11 or 12 years old. Her parents had been very progressive, so they took her to therapists and doctors who all encouraged her to look into that side of her personality. Over the years she had slowly grown out her hair, learned to wear makeup, watched how other women walked and mimicked them. When she was in college she saved her money for hormone therapy and was considering a breast implant if her b-cup sized breasts didn't fill out any more.

This was all a bit much for me. This hot looking girl I had made out with and let blow me was some kind of shemale. I wasn't really put off by the idea, but I had no experience with guys (never had an urge that way) but was all for gay rights and marriage and all that crap. I told her I wasn't angry with her, but needed to think about the implications a bit so I went back to my desk.

I ended up sitting there for the rest of the day, and just about 4:30pm decided to ask her to dinner. I rang her extension, but it forwarded to her cube mate. She told me Mandy had gone home sick for the day after the morning meeting. I left the office and hit a local florist for a bouquet of red roses, grabbed some Thai takeout (who doesn't like pad Thai??) and walked down to her place.

I knocked and knocked until finally, in a small squeaky voice she asked me what I wanted. I told her I brought dinner and wanted to talk. When she opened the door and saw the flowers I was almost bowled over as she jumped into my arms. That was my first night with another man. We've been together now for almost a year and I haven't regretted a moment of our time together. As far as anyone is concerned we're a happy, normal, couple.