Feminization Obsession

Out of all of my fetishes, feminization is the one I have the toughest time accepting. From the time I was a kid and wished for feminine items in the Sears mail-order catalog or trying on some of my mom’s clothes, there has been shame involved.

As a young adult, I would acquire panties, pantyhose and other feminine items. I would go a period of time with them and eventually toss everything in the trash, due to the shame issue.

In my previous marriage, my wife condoned and even facilitated forced feminization, but it was mostly with a slutty, trashy take on it which does push a lot of my buttons, but it also kept the shame involved.

Fast forward to my current marriage to my Mistress. As soon as she found out about my feminization fetish she embraced it.  Mistress had me get all of my feminine clothes and try everything single thing on for her. Mistress made me throw away anything that was gaudy, trashy or didn’t fit.  Mistress purchased me 3-4 nighties in addition to a couple I already had.  I still wear these to this day.  Mistress took me to the salon for pedicures and manicures. Mistress had me dress up on different occasions and we’d have date nights. She took pictures which I still occasionally run across. I looked pretty damn good. She blended my feminization kink with my bondage kink and I was hooked on this new take on my fetish.

Over the years I have acquired a half closet of women’s clothes as well as several drawers of lingerie, stockings, silicone breasts, makeup, heels, etc. We have gone on shopping trips together and she has occasionally sent me out alone to buy something for myself (always a mind fuck). There have been streaks of daily feminization and streaks of nothing at all which is what happens in real life.  I still have some troubles accepting this fetish. Mistress had been amazing at not only accepting and accommodating it but actually pushing me deeper into it which I absolutely treasure.

So here I am today. It’s been over 6 weeks since I’ve had an orgasm. I’ve been locked in chastity for almost 6 weeks. My cock has had zero stimulation in that time. I’ve had dreams the last few weeks of being dressed in public. Mistress just bought me some very feminine lounge pants and had me pair them with a pink tank top that she had me wear last night around the house.  I like the outfit so much that I put it on again this morning along with my perfume and I am over the top in feminization mode. As I woke this morning I could not get feminization out of my mind. My mind raced.

I thought about being dressed up and made up. Being on my knees and sucking on a strap on Mistress was wearing, lipstick smearing up and down the cock. Deep-throating it with tears in my eyes.  Once Mistress decided I sucked well enough she would take me with it.

I fantasized about Mistress telling me I would stay locked until I came from an anal orgasm.  I would try my prostate stimulator to no avail. Mistress would try fucking me with a strap on and I would not be able to cum. Eventually, I would turn to our fucking machine and that would end up giving me my first anal orgasm. In my fantasy Mistress would tell me that since I can now have orgasms with my cock locked up, there would never be a need to unlock me. We could both use the fucking machine for satisfaction and that I should move it into the bedroom.

In another fantasy, Mistress has me dress up and we lay in the bed together and make out like girlfriends.  Soft, gentle, making out, touching, rubbing, licking, etc. I would stay dressed up and locked and give Mistress as many orgasms as she could handle as she verbally pushed my feminization buttons.

In closing, I want to thank Mistress for helping push me more and more in this direction.  For taking what used to be true shame turning it into something erotic and fun.  For taking what I’m comfortable with and making me take it even further.  I am so much better with her pushing my buttons and pushing past my pre-conceived limits.  My feminine brain is spinning.


Pics of me and my Amazon cart.