Tommy (And His Manhood)

What with it being a New Year, I have been putting a lot of thought recently into how my kinks have evolved over time, and what kinds of sticky scenarios I hope to find myself in over the next few months. I am sure that I will post the customary list in due course, but for now I want to focus on one very specific one - formerly referred to as 'little one'.

I have decided that my 'little one' is a boy. At least, that is what he wants everyone to think. He behaves like a boy, dresses like a boy, and refers to himself as 'him', but is missing one important part of his anatomy. He is only eight, so he doesn't really find that this bothers him too much. He is called Tommy (bonus points to anyone who can work out why). I have been craving intense humiliation as part of my play for a long time now, and I think that, through roleplay as Tommy, I may finally be able to find it. At this point I think that, as a disclaimer, I should highlight that I am talking about roleplay between consenting adults.

As Tommy, I could use forced feminisation as a form of humiliation. Tommy HATES dresses, especially pink frilly ones, and being made to dress as a girl would mortify him. Particularly the fact that his body would reveal that he is secretly enjoying it. And, of course, someone else discovering how much his body is enjoying it would be even more mortifying because he doesn’t have the anatomy that one would expect of a boy. Tommy would therefore never tell anyone anything about what may happen, and there are all sorts of naughty possibilities…

Recently, Lilith and I created a scene in which my inner little girl discovered her male tendencies. Rather than taking the parental role, Lilith became my older brother who I walked in on whilst he was trying on female underwear. We made it into a very innocent game of dress-up. I helped my brother to become a girl, and he helped me to become a boy. I found this process of transformation hugely exciting.

The thing that surprised me most was my reaction when the time came to give me a cock. We used a realistic looking strap-on, which I wore underneath my shorts. This, plus the way in which my boobs were strapped to my chest, made me fall very deeply into the role of Tommy.

The scene then progressed into something more sexual, and I consequently withdrew from being a young Tommy and reverted to being my submissive self. However, I still really enjoyed the feeling of the strap-on. People often associate strap-ons with dominance, however I found that, whilst playing with Lilith, the opposite was true. I was using it to give her pleasure, whilst at the same time engaging in my gender-bending fantasies. For a long time, I have felt an urge to truly ‘make love’ to her – to be inside her – and this may be the way forward.

Of course, nothing works perfectly the first time, and we did struggle slightly with the power dynamics within the scene. Grown up Tommy would very much like to explore the sexual side of the play more. In fact, I’m not even sure that that is Tommy – I think that may need resolving. Regardless, I would like to be a submissive with a cock sometimes.

However, the most pertinent conclusion that I came to following that scene was that I would like to enter far more deeply into the role of Tommy as a little boy. A boisterous little boy who can go and make dens and dig holes and collect frogspawn and stick insects – who can fully immerse himself into innocent childhood and forget about the adult world before coming home to his Mummy for cuddles and love. But also a little boy with a pretend cock who is horribly abused by his very own ‘wicked Uncle Ernie’ for being such.

Here’s to a gender confused 2012!