I am not what usually gets called a sissy. Perhaps when I was younger, not sure. But I have alwaya felt more natural and comfortable in women's clothing.

6 years

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I am not what usually gets called a sissy. Perhaps when I was younger, not sure. But I have alwaya felt more natural and comfortable in women’s clothing. A couple of years ago my (now) fiancee’ encouraged it and actually enthusiastically incorporated my love of wearing tasteful lingerie into our s** life a few times and seemed to love it. But she made me get rid of my small number of bras and p****** that I routinely wore under normal male clothes. I missed them often but accepted it. About a week ago I was trying to figure out why I felt so out of sorts, and realized why when I realized what a reaction I had to a random ad/banner to a new sports bra line. Without hesitation I ordered one of them. It came today and I immediately closed my office door and put it on. It is the most natural and comfortable I have felt in months. I have agreed to only wear it and p****** under clothing, never in a situation where she has to see them, never in bed (despite how I find sleeping in a snug A cup bra and snug p****** the most natural and comfortable way to sleep). I honestly do not know why i feel the most comfortable and natural in women’s underthings instead of men’s but it is true for completely non s***** reasons.

New Confession

I slept with my male best friend knowing that he just recently impregnated his long-term girlfriend.
He even slept with her afterwards.
She is currently dealing with an ectopic pregnancy.
I have a lot of regret. It just felt so good during the time.

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I like this girl E*f*** L**** but apparently she’s a lesbian all this time. Man what a waste. I loved her tomboyish style. Damn I wanted to f*ck that girl, so bad. I can just imagine hugging her from behind and teasing her. Then in private times, I would unbutton her pants and make out with her while unbuttoning her polo and taking her cute shoes off. Maybe even have a taste of her socked feet. If only I didn’t have a moral compass.