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Tuesday, January 25, 2011

SL Letter of the Day: Real Or No Real?

Posted by Dan Savage on Tue, Jan 25, 2011 at 10:58 AM

I really need advice on how to get out of a terrible mess. I’m a straight, single, 23-year-old male-to-female cross dresser. Or at least I used to be. The straight part has recently gone out the window.

Okay, um... I'm about to get on a plane—I'm actually on a plane—and I don't have time to bust out an answer for this guy before they close the doors. And after reading his very, very, very long letter, I'm not sure I should. Seems like an obvious fake to me: it has that Letter-to-Penthouse-Forum-circa-1977 quality about it, and almost all letters from straight guys who find themselves being blackmailed into... well, read the letter. Debate its truthiness in comments, offer whatever advice you think the guy needs/deserves, treat it as a good hypothetical if you like, and if anyone has a contact with those Taiwanese CGI animators, I think this letter would make a great short video.

The rest of the letter after the jump.

Like most CDs, I love to get all dolled up in my feminine best—dress, heels, hose, lingerie, makeup, jewelry, wig, etc. Overall, I manage a reasonably good female portrayal. On weekend evenings, I like to go out and about when dressed, doing some light shopping in my feminine form. I have kept this aspect of my life a secret from everyone. None of my family, friends, or co-workers knows that I cross dress — and I really want to keep it that way. I especially want to keep this from my parents, as they would never, ever understand. As I live alone in an apartment, I have tried to be very discreet when coming or going from my complex — I didn’t want any of the neighbors to know about my ‘hobby." For the most part, this wasn’t a problem - except for my next-door neighbor. He’s a 30-year old man named Brett. One day, when I was returning to my place while dressed, I literally almost ran into him as he was stepping out. As you can guess, he was shocked to see his male neighbor completely dressed up as a woman. There was no denying the situation — I had to admit to Brett that I am a cross dresser. We didn’t have much time at that initial moment to get into it too much, but I knew there would be more questions to come.

The next time we saw each other, I was dressed as my normal male self. He took the opportunity to ask me about this unusual aspect of my life. I expanded a little about my cross dressing and asked him to keep it between us. I was relieved when he said he would, and that he seemed to be very understanding. There were the inevitable questions like, Why do I cross dress?, How often?, Where do I go?, Do I have a lot of women’s clothes?, Do I want a sex change?, Am I gay?, etc. I answered all his questions, particularly clarifying that I simply liked to portray a woman, and didn’t want to become one. Also, that even though I liked dressing as a woman, I am straight. He was really very good about it, and even suggested that the next time I went out dressed that I stop by his place to show myself off to him. I appreciated his support and felt good thinking I had a friend who had my back. I told him I’d be going out that coming Saturday evening and that I’d stop by before heading out. So, the next time I got all girlied up, I knocked on his door. He greeted me with a warm welcome and asked me to step inside so he could get a good look. When I did, he told me how great I looked and that I really made a pretty woman. It made me feel terrific! As I prepared to leave, I experienced a bright flash of light — Brett had pulled out a little camera and started snapping pictures of me. At first I was a little uncomfortable with this, but he kept snapping and talked me into doing a little posing. After our impromptu photo shoot, I was on my way. Later on, he caught up with me and gave me prints of the photos. I really liked how they turned out and thanked him for the shots. This became our little routine the next few times I went out dressed — I’d take about 20 minutes to stop by his place first, get a little critique on my look, and then a few pictures for some sassy fun.

Then, during one of our ‘fun’ photo sessions, Brett tells me he wants to talk. He tells me that he tracked down my mother and he has become a regular at the coffee shop where she works as a waitress. He made a point to mention to her that he and I are neighbors. So, every time he went to the shop, I was usually the topic of conversation. Brett tells me that he planned to tell her about my cross dressing if I didn’t give him what he wanted. He proceeds to tell me that he wanted me to give him a blowjob. Of course I refused, but then he threatens to tell my mom my secret if I didn’t comply. I told him I would simply deny the accusation, but then Brett reminded my of the many photos he took of me — on several occasions — in several different outfits. I was totally crushed — I didn’t see anyway around his blackmailing. So, I did the only thing I thought I could — I dropped to my knees and proceeded to suck him off. To make things worse, unknown to me, he had a small video camera running to capture the whole event digitally. To make a long story longer, he has leveraged this situation into ongoing free oral sex from me. Almost every evening for the past three months, I have gotten dressed in various feminine outfits, gone over to his place, and have blown him, per his instruction. And I see no end in sight. I have essentially become his sex slave, forced to give him blowjobs against my will, dressed en femme, nearly every evening. And much of our sexual activity has been well documented on film and video.

How do I get out of this nightmare without giving up my secret of cross dressing?

Completely Devastated

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