Day 4 – Mission Accomplished!

FINALLY. I have knocked out Day 4’s mission: Approach at least 3 women, ask for recommendations on places to buy cool men’s clothes, and get at least 1 recommendation.

It was relatively uneventful, to be honest. I met some friends over at Metro (a cool bar across the street from my apartment). I decided to rock the skirt and heels again (that is becoming my personal ‘brand’, for lack of a better term. More on that later).  The approach was a couple of girls, one very cute, the other not so much. Both seemed happy and friendly though. I said Hi, introduced myself, and just asked, “I have a random question…”  She suggested Uptown Cheapskate, a trendy second hand clothing store just up the street from my place.

The next approach was similar. 2 girls. One is hot, the other not. She suggested Spark, which is a more edgy boutique type of store on State Street.  It is a place for trendy girls, gay guys, and straight guys with a sense of adventure to shop.

The third approach was a little more protracted. It was a guy and a girl – the guy was dressed kind of trendy (affliction shirt, piercings, a few tats, kind of a meat head type… but acted kind of gay – the girl was rather unattractive).  One of the regulars at Metro is a very tall transgendered asian girl. From a distance, this person looks like a super model. 6″ tall, lengthy blonde hair,  exquisitely long, perfectly formed legs that lead up to an ass that is small, tight, and perfectly proportioned to her waist, creating curves that make a man’s engine rev.  Upon closer inspection, 2 things become apparent. “She” is deaf, and, “her” cheek bones and jaw line apparently are the last things on her body to respond to hormone therapy. They still tell tales of the days in which she was a he. “She” is a fascinating phenomenon because from a distance, every man with even the slightest predilection for pussy will get excited looking at “her”. In that moment where you realize what you are ACTUALLY dealing with… it’s some what of a come-to-jesus moment where you have to ask yourself some revealing questions about your own sexuality.  On this night, her tiny tube dress was failing to cover her completely. Emerging areolas were a perfect conversation piece to start chatting up this 3rd set.  They were not at all helpful, but at this point, I did not care. I just needed to make the third attempt in order to pass off this mission.

I invited the girls from approach #2 to come back to my place for some drinks, which they did. We stayed up till 3am drinking beer and talking about funny but inconsequential things like astrology and their deep, abiding love for  local band, the Suicycles.  (side note: I hate any business that uses a reference to a dog in it’s name, and any band that references suicide in it’s name. Such a lame, protracted, semi cry for attention).

I’d like to thank my friend Ryann. He has also embarked on the Sylelife 30 Day Challenge. We are helping each other out by holding one another accountable. It makes the process even more fun, and provides a very welcome added dose of motivation.





I’m going to say it’s a girl because she has a AMAZING legs and ass, huge fake boobs, always is dressed in a tiny dress  that barely covers her all up. It seems that the hormone treatments have not yet smoothed out some of her facial features. Her cheek bones and jaw line still tell a tale of the days when she was a man.

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