How Did I Get Here

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.

Mischelle: You really are a sissy slut aren't you?

Me: Yes, Mischelle.

Without warning I hear the cane just before I feel its bite. Mischelle no longer has inhibitions on inflicting pain on my bottom. Who knows how many times she strikes me with the cane and paddle. I am crying for her to stop, but determined to never use my safe word.

Mischelle: Now that your ass is warm you can now earn what you want. I am in a good mood so I am going to let you chose. Twenty strikes with the cane or forty with the paddle. Or of course you can end it with a word.

Me: I love being your boy toy too much. I will accept the forty.

Mischelle: Whose boy toy are you?

Me: Mistress Mischelle, I am Mistress Mischelle's boy toy. I am sorry.

Mischelle: Yes, you are sorry. Not much of a boy either. Forty strikes with the cane it will be.

I let out a sigh and brace myself for the worst beating I have ever endured. I am yelling out and begging with each strike. I cannot count anymore and trying to endure.

Mischelle: Such a pitiful little baby wimp. I will be surprised if all that blubbering does not bring the neighbors over here to check on you. Bet you would like that. Just ten more and you will get what you want.

I grit my teeth and try to be quiet, but that is a losing proposition. What kind of person would subject themselves to this. Finally she rubs my striped sore bottom signifying it is over. I hear her moving away but I know better than to move.

Mischelle: I had to get a picture of my handy work. I think you may have to consider wearing a diaper for a few days. Your ass is going to hurt for a while. I can't for the life of me understand why you would want someone to do that to you, but you have earned your prize. What is it that you wanted?

Me: (Struggling to focus for a second as my ass is on fire and I too am wondering why I took that and what do I really want.) Mistress Michelle, I want to know what it feels like to be fucked like a girl.

Mischelle: If that is what you really want. Go get the large dildo and harness that I sometimes let you wear and use on me so your little dickless self can wonder what it would be like if your dick still worked.

I return carrying the harness with the largest dildo we own. On a number of occasions Mischelle has hand fucked me with the two smaller dildos and over the years I have stuck them to the wall and floor and had my way with them. The head on this one is making me nervous. To my knowledge Mischelle has never worn the harness.

Mischelle: Did I send you for lubricant?

Me: No Mistress Michelle.

Mischelle: Girls make their own lubricant. If you want to know what it feels like to be fucked like a girl, you have to be fucked like a girl. Slide my shorts down, but leave my panties on. Slide to harness on me and tighten it up. Lift up your gown. That is really what you are, a sissy little cock sucker. I doubt you will ever know what a girl feels like when she is fucked. If you are worried about your little boy pussy, I will let you lubricate my cock like a girl.

I go to work licking and sucking Mischelle's cock, trying to salivate as much as could. All the Mischelle is egging me on by commenting on my skill or lack thereof.

Mischelle: You look good with a cock in you mouth. No wonder you parade around here in those panties. I am going to have to pay attention. I have been punishing you when I thought you were eyeing women's asses, when I should have been watching your eyes around men's crotches. I bet you have dreamed of a hot cock in your mouth your whole life. Now bend back over the arm of the couch.

She flipped up my gown and slid my panties down. Mischelle then twisted the butt plug and popped it out. I was alarmed that it hurt and seemed to have become dry. Mischelle sensed my alarm and laughed.

Mischelle: Something you want to say or maybe a safe work you want to use?

Me: Please Mistress Mischelle, start slow and be gentle.

Mischelle: Ha! Were you gentle or slow when you popped my cherry all those years ago. No. You nearly ripped my panties off. Of course, even though I did not know how big a sissy you were, you did not last long and it was over. You never really could satisfy me. Why do you think I let you use this cock on me. At least I could know what it felt like to be full. Now it is your turn. Have you thought about how this ends. I am not going to shoot my load and shrivel in a few minutes. No you are going to get a full and lasting fuck, unless have enough and give up. What do you want again?

Me: Fuck me like a girl.

Mischelle: Excuse me.

Me: (stammering) Sorry Mistress Mischelle.

With that, she spread my cheeks and rammed that cock into me as I screamed in pain.

Mischelle: You do scream like a little girl, but can you take a cock like a little girl.

As she began to pick up the pace, I began to adjust to meet each thrust. Though there was still some pain, I hate to admit it, but I began to get comfortable and feel some pleasure. At some point she stopped thrusting and reached around me. I thought she was going for my clitty but I was mistaken. By this time my throbbing nipples had become numb, but not for long. Through my bra, Mischelle ripped off my nipple clamps sending shockwaves of pain throughout my body. I cried out in pain and she laughed.

Mischelle: Had enough yet?

As she pinched and twisted my tender nipples, I bucked against her cock still buried deep inside of me. We developed what became a painful but pleasurable rhythm. As her breathing began to quicken, I realized what I thought would end this, her orgasm. Or so I thought. Normally when I make her cum, she is one and done, if I really make her cum. Not this time. After a slight pause, she released my nipples and began to seriously thrust. I began to wonder if I might actually be able to come like a girl as she sawed in and out of me. As soon as I had that thought she exploded with glee and hugged me tight. It felt good for her to withdraw her cock and rolled over on the flow. She drew me over and embraced me, caressing my extremely sore, striped bottom. I had no words, but was contemplating if I could call it quits. I had gotten what I had always desired. Maybe more. But could I take any more. But then she broke the silence.

Mischelle: Wow. I can't believe how good that was. I love you so very much. I can't believe you would endure that for me. And it was so good. I don't think we need a safe word anymore, do we?

After a long silence.

Mischelle: Annie, do you need a safe word any more.

Me: No, Mistress Mischelle. I am now your other pussy to do with as you please. Thank you for your willingness to take me as you very one sissy plaything.

Mischelle: Good. This experience has given me some ideas how to bring out your true nature and find some pleasure for myself.

How did I ever get here.