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SISSY CUCKOLD STORY

  

  

The day I met Sara I knew she was the girl I would marry but I didn't think it would end up like this?

 

We had your typical relationship up until a few months after our wedding. We stopped having our usual sex every day and went to about once a week. She said she was just stressed out at work. A few days later I came home from work and she was waiting there in a sexy pink teddy and we made love all night.

 

Little did I know that would be the last time I was ever going to have sex.

 

Sara had a present for me later that night. She said it would spice up our sex life. I would agree to anything to get back to the way it used to be. She handed me a box an in it was a chastity belt. She said she had it made special for me and if I would try it on to se if it fit. So I agreed. She said she just wanted to know if it fit because it was for special occasions. So I put it on for her like she asked and it was a perfect fit. I modeled it for her and asked for the key so I could take it off. Sara said I would have to wait for the key till tomorrow because she left it at work. I agreed it was no big deal tomorrow was Saturday I didn't have to go anywhere so I went to sleep.

 

 

I woke up Saturday morning with my penis straining to become erect in the confinements of the chastity belt. Sara had already gone in to work. I looked down at my new chastity belt and tried to figure out a way to get it off. After a few minutes I knew it would be impossible without the key. So I called Sara to make sure she would bring the key home. When Sara answered the phone she said she was really busy and couldn't talk right now she'd call me back. So I went and took a shower.

 

I was done with my shower and came back to my bedroom to get dressed. I opened my dresser for some underwear and all I found was panties and a note. This is what the note said:

 

 

To my dear sissy husband Jack,

I replaced all of your boxers with panties. I know how much you like trying mine on when I am at work and out with my friends. You didn't think I knew about that did you? I also know how you try on my lingerie and wear it around the house. For now on the only thing you will wear under your clothes at work are your new sissy panties. And at home you will wear the new sissy maid uniform that is hanging in the closet. If you don't like these new rules. Remember that videotape I made of you that night you were drunk when you were dressed up in my clothes sucking on that dildo? Well I might just have to send a copy to your office. Now go to the closet and put on your new uniform!

Love,

Mistress Sara

 

I had no idea what to think about all of this but I knew if I didn't do what she said she would send that tape. So I opened the closet and saw a frilly French maid's uniform hanging there, there was also a large box under it. The box contained a brown shoulder length wig, a pair of fishnet thigh highs, five-inch locking stiletto heels, and a leather locking corset with attached garter belts. I grabbed everything and started to put it on. I could feel my dick trying to get hard again in the belt. It took me a few minutes to figure out how to put everything on right. When I snapped the locks I knew things would never be the same. I was now Sara's sissy maid Jack.

 

I sat there and wandered how Sara knew I wore her lingerie? I was always careful to make sure I put it back where I found it. I just couldn't figure it out. I'm sure she would tell me when she got home.

 

Then the phone rang. I just knew it was Sara. I stumbled over to answer it. This was the first time I ever wore heels so it took a few rings. I answered and it was my Mistress wife. She said "it took you long enough you fucking pussy. You should have answered it on the first ring. What if it was somebody important like a well hung stud that wants to fuck your wife's dripping pussy?" I couldn't believe this was the same girl I married. I tried to tell here I couldn't walk in the heels and she told me that I better learn fast. Then she told me to shut up and listen. I knew when I first met you were going to be my cockold sissy husband. I cheated on you three times when we were engaged and you always took me back without saying a word.

 

You are a pathetic excuse for a man. I will be home in an hour and you better have learned to walk in your shoes by then. By the way you will be meeting a new friend of mine tonight so be prepared.

 

Was she really going to bring somebody home to see me like this? She surely was just trying to scare me I hoped. I started to practice walking in the heels after about 30 min or so I was getting pretty good at it. I kept walking and then I heard the key in the lock and in walked my wife Sara.

 

I see my sissy has learned to walk. I asked her why she was doing this? Because it is what you want you just don't know it yet. I am only doing this out of love for you, not to hurt you. You will understand. Now enough talking get your ass over here down on you knees and worship my pussy sissy! This will be the first thing you do when I get home for now on. Do you understand? I answered OK and her hand slapped me across my face.

 

You will always answer me by the name Mistress Sara for now on! Do you understand? I answered yes Mistress Sara. Good now get that tongue to work and bring me to an orgasm.

 

I was so confused, humiliated, and aroused by what Sara was making me do that I forgot all about the friend she asked to come over. What was I going to do? I couldn't really let another person see me. After my new Mistress climaxed I asked if she was really going to let some body see me like this?

 

Of curse I am you are my sissy maid now. You have to entertain all of my guests. Now come in the bathroom we have to make you more presentable. I'm going to unlock you know. Strip and stand in the bathtub.

 

 

She handcuffed me to the shower head and covered all of my body from the neck down is a pink flower scented lotion making sure to rub in all my body hair. She then took off my chastity belt my cock immediately sprung to attention. She slapped it a few good times with her hairbrush to make it go limp again then started to shave my pubic hair.

 

When she was done she told me to take a cold shower, making sure to get the hair remover off. I started the shower and by the time I was done the only hair I had left was on my face and head. I stepped out of the shower and Sara was standing there in a tight little red dress. My cock was throbbing at the sight of her.

 

I see the cold shower didn't do you any good maybe a few more hits with the brush will tame that thing. Lets see how may is it going to take?

 

Eight hits later my cock went limp and I was almost in tears.

 

She handed me my chastity belt and told me to put it on. I managed to squeeze my dick in it just as I was starting to get hard again. I just couldn't stop thinking about the sexy red dress Sara had on. I have never seen her wear anything like that before.

 

Doesn't this dress just scream fuck me? To bad you will never get to put your worthless little cock in my beautiful cunt ever again. I thought of tonight when I bought this dress. I got it special just for you. Don't worry Jack I am really doing this out of my love for you. It is for the good of our marriage. You'll get laid tonight, just not by me.

 

I didn't know what she meant by me getting laid. I didn't have time to think about it now. Sara ordered me to put my uniform and wig back on and shave extra close. When I finished shaving she started to apply the makeup. She said don't worry, tomorrow you will learn how to do it all by your self. But we are in a hurry now so I will do it for you. I couldn't believe my reflection in the mirror when she was done. I truly looked female. I had become my wife's sissy. We got finished just in time as the doorbell rang.

 

Don't just sit there, answer the door! I never felt so degraded and humiliated in my life as I did when I answered that door. I was truly my wife's sissy cockold for life when I opened that door and it was my boss Dan. He walked in and said I always knew you were a sissy. Then he started kissing my wife like they were lovers.

 

Your boss Dan and I have been fucking for months now. Why do you think you go on all those business trips? We met at the office party back in January. He fucked me on your desk when you were out their drunk telling stupid jokes. The chastity belt was Dan's Idea. He has the only other key so if you ever want to have an orgasm again I would treat him like you treat me. That means when he walks in the first thing you do is get on you knees and service his cock. Get on your fucking knees and suck his dick Jack or do you want to get slapped again?

 

I got down and reluctantly wrapped my lips around his cock. It was more then twice the size of mine, it had to be ten inches long! I couldn't believe I was sucking my boss's dick dressed up like a fucking sissy maid. I was so humiliated yet so turned on at the same time. Maybe Sara was right, this is what I always wanted.

 

While you are giving Dan your first of many blowjobs let me tell you the rules in order for you to have an orgasm:

 

You are allowed to orgasm when you are five up on us.

An orgasm can be given to either on Dan or myself.

For every orgasm I give Dan you must match and give him one.

For every orgasm Dan gives me you must give me three. After all, you are my husband.

The cycle restarts every six months.

If you are allowed to have an orgasm it will be in a way we specify.

We add new rules when we deem it necessary.

It looks like Dan is getting close to cumming. You better stop Jack, we can't let you get one up on us so soon. Come here Dan, put those ten hard inches in my wet pussy. Come fuck me like Jack never could.

 

Dan pulled up her skirt, leaned her over the back of the couch and rammed that ten inch cock deep into Sara. I have never seen my wife scream and pant like she was. I could never pleasure her the way Dan could. Maybe she is right about this being good for our marriage. She laid there for a minute over the back of the couch with Dan still inside her.

 

Dan, that was the best fucking I ever had in my life. Jack could never even come close to that with his tiny little pecker. Speaking of Jack, it is time for him to go to work. Sissy Jack my cockold husband, it is time to come clean a real mans cum out of my pussy. Don't be shy, you tasted him in me before. Remember that edible lubricant you liked so much? Now you know where it comes from. Just think I gave you the pleasure of watching a real man fuck me. And just think you may get lucky and give me an orgasm while you are down there. Then you will only be three down, but the night is still young. When you are done with me get Dan nice and lubed up, and get ready to bend over.

 

 

I managed to eat Sara to another orgasm and started to lube up Dan's massive cock. I can't believe that ten inch monster was going to penetrate my virgin ass. Sara came over and kissed me passionately and told me this was going to bring us closer together.

 

You see Jack honey, this way we can share lovers. You get to feel what I feel. You get to experience what I experience when that big throbbing cock is thrusting in and out harder and deeper on every thrust of his pelvis. You get to share what most men can't with their wife. You get to experience the feeling of loosing your virginity with a real man.

 

 

  

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