7 years
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My therapist has said that she is fine/not a problem in the world for me to come to one of my appointments cross dressed. Simply so I can feel more comfortably and naturally myself. Since it has always been about my gender identity, not anything to do with s********, I am looking forward to it very much for all the right reasons. She has been exposed to the inner feminine me, but said she would like to see/talk to me in that mode because she feels that the need to smother/hide it from the entire world makes me instinctively keep a wall up to some degree with her anyway. I am genuinely thrilled that I was able to ask her if it were permissible for me to come to an appointment dressed, and I was so happy she reacted so encouragingly about it. This will be the first time I have ever been seen dressed as a woman by anyone, ever, it has simply been something I allowed myself to express when home alone. As thrilled as I am to have the safe nurturing opportunity to be fully myself loke this, I am also very nervous about it. Not because someone/she will see me dressedas my true self, but because she is a very classy, well dressed woman. And I am actually worrying about whether she will be judgemental about my choice of wardrobe/style.

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.