How Did I Get Here
As long as I can remember, I have had the desire to dominated, first by girls, and as I grew older, women. I never had much opportunity to do anything but fantasize. I remember sneaking around as a kid, playing with my mom's and sister's underwear, using towels as diapers, punishing my genitals with a heating pad, and maybe the strangest to understand, sticking a plunger to the wall and fucking my bottom with it. Finally, when I was 21, I had my first and only sexual encounter. Wonder if she thought it strange that I only desired for her to be on top. Even stranger when I coaxed her to tie my hands behind my back and ride me to she wore out. What I really wanted was for her to ride my face and turn me over and spank my bottom. To require that to see her I must wear her panties. Alas, those things never happened and the relationship ended and with it, any opportunity to live my fantasies.
A few years later I began to date the woman who would become my wife. She was and is very conservative and dated a long time before there was any thought of sex, but we began to progress closer and closer. For her graduation she was given to very pretty pairs of panties. Of course, they were not her style and I never saw them on her. The temptation was too great, so I took them from her underwear drawer. I began to wear them when we went on dates, fantasizing that it was under her orders and that one day she would force me to show them off to her friends. That never happened, but one night she slipped down my pants and discovered where her panties had went. She did not freak out and I had the most mind-blowing orgasm ever. Now I bought more panties and other types of lingerie. Sex became better than I could imagine. I never was with her when I did not have some kind of feminine attire.
Maybe the highpoint was when I bought a French maid outfit for Halloween. By now, I was regularly on my knees before her, worshiping her feet and licking her to orgasm, always dressed for the occasion. I now got her to spank me on occasion, though I could tell her heart was not in it. I thought she might me coming around though when she told her roommate that there was a trunk in her closet that if something happened, to make sure she got it out of there. Always wondered if Missy ever opened my trunk. Especially after Karen spanked me one afternoon while Missy was in the apartment. She could not have helped but hear, but to my chagrin, she never mentioned it. But my fantasy life cranked up.
Eventually marriage did happen. What I thought would be a glorious escalation never materialized. I wore panties twenty four seven, but my wife's heart was just not in it. She was cooperative for 7 or 8 years, but our interactions just slowed. I could still force the issue by tying myself to the bed, sometimes diapered, sometimes with panties and bra, always having clamped nipples and blind folded anticipating being discovered. More and more it just depressed me. Married almost thirty years, affected by ED, nothing really excited me anymore and the prospects seemed dim. I was still playing some and more and more my wife would roll over to me in bed, slide down my panties, pinch and twist my nipples, while I unsatisfyingly wanked myself to an orgasm. To get there, I would relate some fantasy or another that was never going to happen. Becoming her personal maid, being fed my sissy cum, being fucked like a girl. Never the ones that really excited me. I was contemplating giving up all of my fantasies.
On a couple of occasions over the years, I had thrown all my accumulation of lingerie, clothes, toys, props, pictures, and stories away. Only to regret what I had lost and start over. Once or twice I took the less drastic approach and boxed everything up and put it in the closet. I have always found my way back into it. I suspect to my wife's disappointment. These actions led me to the last year or so. I have left Karen, or Mischelle as I like to call her when I think of the dominant woman I I craved her to be, numerous letters over the years. Normally they are left where she can find them and know that I am restrained somewhere for her to find me. Submission contracts, fantasies, confessions, and the like. I have a 2TB memory stick filled with pictures and videos of me, stories I have written, and similar things I have saved off the internet. So, kind of at the end of my rope, I wrote one with a different proposition.
I got ready by wearing a light blue pair of satin panties which are emblazoned with cock sucker across the front that hold in a nice size butt plug in what I like to think of as my boy pussy. I added a lacy purple bra that encases a pair of hard biting nipple clamps. Really they are just very small wood clamps that I have added a rubber band to keep them from completely closing. Over them, I slipped on a silky pink short gown. I felt I was now ready to write what might be my last letter.
Dear Mischelle,
I know the past thirty years have been crazy with my fetishes that you can't understand I can't seem to break away from. I find that I can't sleep in the same bed with you and not have those desires and neither of us want to sleep in separate beds. I have a proposition for you as a last chance for either, you to embrace the possibility of you fulfilling my desires, or me laying them to rest once and for all. As you might expect, you will find me in the guest room tied to the bed, likely in some discomfort. You will notice a paddle, cane, switch, paint stirrer, and a flexible ruler. I will also be blindfolded with a dildo in my mouth. I will be completely at your mercy, or lack thereof. I propose, that beginning today you attempt to push me past my limit. You can punish me, force me to obey your every command, humiliate me, and use me as you see fit. Realizing our work situation, I know it will not be 24-7, but timing is completely up to you. Your goal will be to force me use a safe word to end this experiment. If you force me to that point, everything goes away, never to return. I completely give up every prop that goes with every fantasy. I hope you might grow to enjoy your power over me and we find common ground to enjoy the rest of our marriage in this fashion. But you will have the opportunity to prove to me that I really don't want to be your slave and that I will have to relinquish those desires. I believe a good safe phrase would be, "I am over this." I am also leaving you a memory stick which might have some useful information.
Completely Yours,
Annie
Almost a year later I wonder how I got here. There are some stories to tell, but earlier tonight I found myself in the same attire, nipples clamped and butt plugged, massaging and kissing Mischelle's feet.
Mischelle: What do you want Sissy?
Me: I want to be fucked like a girl. Please Mistress Mischelle show me how it feels to be fucked like a girl. Please, please, please. I will do anything you say.
Mischelle: You will do anything I say anyway, unless you want to give up and try to be a man. You think you could be a man.
Me: No Mistress. I don't think there is any chance I will ever be a man. I could never please you with my worthless dick. I never even dream about in any more. I need you to teach me how to cum like a girl.
Mischelle. Ok sissy, if you can prove you want it. Go get me a paddle and a cane, and bend over the end of the couch.
Mischelle lifts the back of my gown and tucks the back of my panties under my cheeks, but leaves my little clitty encased in the front of my panties. She pokes the butt plug in and out of my boy pussy causing me to moan.
