I Am Cuckolded – A Sissy Man Tale

I’m living the life as a sissy man.  I am cuckolded and my mistress has observed and recorded every one of my climaxes from the very first day we met to now. She has never allowed me to cum without her consent.

There is a calendar on which she has indicated the days of the years that she will allow me to ejaculate, whether it is by masturbation or sex.

She has some lady friends she meets with on the side. They are also allowed to note which days I am allowed to cum should they be so interested in using me. It is a very rare event indeed that I should be allowed extra days

Although that promise is always there for me when I do something exceptional.

I Am Cuckolded

My Sissification Training And Pegging Sessions

Each year, during the month of April my sissification training is undertaken. During that month whilst I’m at home I am only allowed to be dressed up in women’s clothing.

The only sexual contact I am allowed is when she pegged my ass or any of her friends.  During this month I can be fucked at any time but I am never allowed to cum.

Should I cum strict punishment will be inflicted upon me.

My Chastity Punishment For Being Caught Masturbating

In the past, I have secretly cheated by masturbating.  I was caught one time by my mistress.  She decided the only way to control my bad habits is to place me in a cock cage.

As she placed the cock cage on me and locked it with a key she told me this would be worn permanently for the next three months.  She placed the key on a necklace around her neck.

I realised, I was now at her full command and I fell to my knees.

Over those three months of abstinence I was not drained once. My mistress humiliated and degraded me continuously.

I now never want to displease her as that punishment was very difficult for me to cope with.  Have learned my lesson to never cheat on her again.  If I ever attempt to cheat on her I have to make sure I am not caught.

When I Was Finally Released From Chastity

When my mistress acknowledged the three months was up and had finished playing games on me when I was in chastity she finally removed the device.

My mistress told me that she would allow me to climax.  But, it was only to be done if I could fit the biggest and blackest butt plug that I had ever seen totally into my ass.

Then and only then would I be allowed to masturbate myself to orgasm.

I had to start of with a smaller sized butt plug

And work myself up to the biggest butt plug.  It was very difficult to put even the smallest of butt plugs inside me even when I was completely lubed up.

Took me upwards of half an hour before I could stretch my ass big enough to even think about taking this massive sex toy up my ass.

Finally, though with deep breathing and relaxation techniques I managed to get it all in there and I blissfully masturbated in front of her.  Within seconds, I was blowing my load all over myself and around me.

Never before had I spurted so much cum from my testicles.

When I was done, I was totally spent.

I was so spent that the butt plug was still up my ass and it was ten to fifteen minutes before I could muster the energy to remove it.  My mistress then commanded me to clean myself and the mess up.

Being Encaged In Chastity Helped Me Be A Better Cuckold

When I cleaned everything up and showered she immediately placed the cock cage back on.   She told me that I would be back to my regular calendar schedule when I was able to show her that I could be totally trusted.

But for now she would leave the chastity device on.

This remained the status quo for some six months before I was given the reward and freedom to wear it only on special occasions.

Wearing the chastity device allowed me to control my erections.

Anyone that has been encaged in a chastity device will know that getting an erection can be extremely painful.  This I believe has empowered me somewhat as now I do not get erection.

Even when I am asleep unless I mentally allow it to happen.

My Mistress Humiliates Me In Front Of All Of Her Friends

She will often humilates and devalues me in front of her female friends.  My mistress makes me take my pants off to display what she calls my pee wee cock.

She tells me that my cock looks like an overgrown clit.  Perhaps I would have been better off being born as a woman.

Sometimes this embarrasses me

But more often than not I am thankful that she stays with such a little man like me.  Sometimes when my mistress and her friends drink some wine she will say to me:

“Slave, present yourself to me!”

When she tells me this command I have to pull my pants down and get on all fours in the doggie position.

Then my mistress and her friends will take turns in butt fucking me with various sized strap-ons.

Funnily enough, this does not really embarrass me.  Rather it invigorates me and is a treat outside of the set times I am allowed to cum. My mistress often gets me to do not so nice tasks on her and her friends.

One of those tasks I find very distasteful.

She showers at night on a Thursday to go to work on Friday and then will not shower again.  Then on the Sunday evening she will make me go down on her.  She makes me lick her pussy and ass that have not been cleaned in three days.

Sometimes the stench makes me dry retch but I know this is one of the things she enjoys.

She will say to me:

“Lick my dirty ass hole clean you non man. This is all you deserve you retched cuck and this is your position in our relationship. You are no more than my ass wipe.”

Sometimes these words hurt

But I know how lucky I am that she stays with me and I will do anything to please her.

She often giggles after having one of these sessions.  And reinforces how lucky I am that I am allowed to even lick her dirty asshole.  I agree being the hot wife that she is.

She Told Me I Was Never Allowed To Place My Cock In Her Pussy Ever Again

When I was first in training my mistress was very cruel to me.  She had told me initially that I was never going to be allowed to put my cock into her pussy ever again.

Although being a man in chastity in some ways appealed to me.   What I did not know was how far she would go to show how little she needed my cock.

She laughed at me one night early in my cuckold training and said:

“I feel the need for a bit of dicking.”

At that particular time she had me in a Hell’s Couture surgical steel cock cage and she pulled out a massive strap-on.  She ordered me to strip, placed the strap-on securely around my waist and commanded me to use it.

I knew what was going to happen.  She laughed at me as I began to pound her beautiful pussy.

Below the strap-on I could see her juicy pink pussy tingling.

My chastity training took a whole new level of pain as I began to get an erection inside the confines of my cock cage.  I started to cry like a little girl as she ordered me to continue.

The pain was so excruciating it felt like my cock was being grated like a piece of cheese.

The more I cried the more she laughed. She orgasmed but I had to continue thrusting the strap-on into her wet pussy.

Finally, she was spent and ordered me off of her.

I laid in a fetal position for many hours after that. I cradled my damaged manhood and was not allowed to properly treat it.  Eventually, after about 4 hours she came up and unlocked the device.

I could see that my body was bruised and discolored with some lacerations to it.  She ordered me to bathe and rub some balm on it.

At that moment, she may have felt pity for me and perhaps she thought that she had gone too far.  That made me love and treasure her all the more.

I came to the realization that at that time I was her slave, her cuckold and her man-servant to do with as she pleased.

My Relationship With My Mistress Is Always Changing

But now coming back to the present, our relationship is still always changing at every command that my mistress makes.  She tells me to do things that I would otherwise never do.

I know it pleases her which in effect pleases me but I am scared as she has told me that she wishes to experiment with electro anal sex toys.

She has already purchased a bondage rack

That she has placed in the garage that can be moved to accommodate multiple positions whilst keeping me in place. She has also purchased a bipolar powered (two channeled) butt plug and discussed using it with her friends on me.

I was hoping someone out there has used one and could let me know what I am in for.  So that I can be prepared and help me overcome my anxiety of what is to come.

I would walk over hot coals for her.