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Gender questioning: in the beginning - first contact

First contact with a real girl that is. 

Apologies that this post will contain some reference to mild sexual experiences but I will try to be delicate. 

As I have mentioned in other posts, in my teenage years I was as attracted to girls as the next boy, but I was also very much attracted to the idea of being them, although at the time I had no idea this was not “normal” and maybe signified something about me. 

Unfortunately I had little to no success in getting a girlfriend. Ok, let’s be honest: no success. At all. Maybe I wasn’t masculine enough! Hmm. 

I was fourteen before I first kissed a girl. We met at the ice rink, skated together and chatted and then before she had to go home, we “snogged”. I had zero experience so had to follow her lead and she was rather vigorous in her kissing. Forceful even, and pushed her tongue well into my mouth. Frankly, I feared she might eat me. Nice to get a score on the board, but I cannot say that I enjoyed the experience. You have to start somewhere I suppose. 

My second encounter could not have been more different. And I mean good different. We met on a summer camp weekend, sailing and sports and atuff. She was from a different school although still in the same county. Her name was Katy and she was beautiful, tall, slender and with long blonde hair. So far out of my league we might have been playing different sports. Somehow, we got chatting during the day, got along well and on the Saturday evening, left the dancing in the marquee to go for a walk by the lake. Walking became walking hand-in-hand, which after a while became sitting by the lake and watching the sun go down. This became kissing. Kissing Katy was nothing like kissing Claire had been. Where Claire had been firm and forceful, Katy was so soft and so gentle, kissing her was the nicest thing ever. After a time, it got dark amd turned colder so we qemt into one of the tents amd lay down, still kissing in this soft lovely way. She asked me to stroke the back of her neck under her hair, gently with my fingernails because she liked that. She did the same for me, it was tingly and felt nice. All the time, kissing one another. At some point I touched her breast, still kissing, still playing with her hair and tickling her neck. Her breast was the most deliciously soft wonderful feeling. Through her t-shirt I could feel the shape of her, her softness, the small proud nipple and the fabric of her bra. She allowed my hand inside her t-shirt, directly touching her bra, which was soft and satiny, no wire or padding. Touching her softness through the satin and stroking the nipple felt divine. It was beyond anything I had ever imagined. Now a normal teenage boy would when he got home spend a lot of time "thinking about" the kissing and the breast fondling. As we have already established, although I did do that, I was not normal and there was more to it for me. I longed to know what it felt like to her. I put on one of my mum's bras and tried to cup and stroke my own chest, and to find and stimulate my own nipple to feel what that is ike through the satiny bra material to feel like Katy. But I knew I wasn't feeling it quite the same. My chest was flat and hard, none of her beautiful softness; my nipple tiny and flat, not rounded and raised. It felt nice, and sexy, but in my heart I knew I wasn't feeling it for real. Nevertheless, this remains one of the most influential moments of my trans life. That feeling, of my breasts being touched is still something I long for. It is why brassieres more than any other garment define what it is to feel feminine for me. It is why the ritual of putting on a bra is key for me when I dress to be Nicola. Fastening the band, covering myself with the cups and then securing it in place with the shoulder straps is so important to me. That first contact with beautiful Katy shaped my vision of feminity, but more than that, how I see myself as female.  

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