Well, I guess it's probably good to follow-up some long-term instrospection with some more every-day topics...
Lately my Mistress has been wanting to take things a bit further. She has been wanting to integrate pegging into our play time for a long while now. I had resisted for a long time but in the past few months I have agreed to go along with things as long as she is gentle and works things in gradually. She has, in turn, slowly brought some anal play into the mix and it is quite difficult to bear since it tends to bring up feelings of panic and desperation rooted in trauma from my past. However, I have not been the sub I wanted to be when we first entered into our relationship and I feel like I owe it to her since I have made her progressively less and less happy the longer we have been together.
Over the past few months we have been slowly gathering items that will become the focal point of our play sessions when we have a few free weekends. Her plan is to turn me into a whore. A micro skirt, tight fitting top, go go boots, stockings & garters, heavy make-up, a cropped fur jacket, and a chastity device to top things off. I am assuming that there will be no panties since she prefers direct access to my buttocks and no bra since it shields my nipples from her teasing. I'm never allowed a wig since I'm never supposed to actually pass for a woman... just a sad man in drag. I'm almost certain she will "throw me a bone" and probably add a pair of fur earmuffs and some fur-trimmed mittens and there's always the possibility of a very feminine (borderline silly) hat. These will serve dual purpose: to increase my humiliation and to "add fur" to the equation but in a way that I will not be able to feel it nor garner any pleasure from it... at least that is how things have often worked in the past. Either way she knows that will get me struggling inside my chastity device.
She hasn't decided yet how she wants things to play out but I know she has interest in both acting as a client, a pimp, and a cop, which basically means I might be in for a hell of a night if she chooses all three. The one thing I can be certain of is that she plans to violate me as much as possible and she has gone over several of these fantasies while teasing me in bed. Being a client that uses me to pleasure her and then violates me and sends me on my way. Being a pimp that smacks me around and then violates me. Lastly, being a cop that arrests me, beats me, and then violates me. I'm guessing the chastity device won't come off until she has put me through the gauntlet so I'm not sure if I would prefer having all three instances happen in one night or if I'd rather have it spaced across three nights.
In any case I know that this will not be for my pleasure. It will probably hurt and I will probably cry a lot. While this completely terrifies me I feel like I owe it to her to prove my devotion and also to keep the train rolling down the tracks. At the same time I'm disturbed that the thought of this turns me on. This is definitely one of those cases where fetishes trump common sense.
I think what scares me most is that I feel like I will be a different person when this is done and I'm not sure if that means I will have gained something or if I will have lost something precious.
I'm sure there are subs/sissies out there that are probably envious of this position and wonder why I'm fearful but at the same time this is one of those cases where a fetish activity is being twisted into an activity that is unpleasant in certain ways.