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Once a Loser Always a Loser

With the awesome rewind weekend rate special, it took me back to the beginnings of my phone sex experience. And one of my first losers. Who, by the way still is. His name is Mikey, and we have had an amazing journey over the years.

Mikey first started calling me as a jerk off junkie loser

Addicted to stroking while being laughed at and called a loser. Why? Because Mikey was and still is pathetic and unable to find women. I know some girls will feel bad for poor saps like Mikey. However, the real problem was he couldn’t even get it up for a girl if he tried. Trying to date women out of his league certainly did not help. I remember one time he went on a date to a ball game. The poor girl. She told him she was going to use the restroom never to return.

Did I feel sorry for him?

No fucking way. Men like him should be ridiculed and laughed at for the spineless bitch that he is. I can remember his poor pathetic voice sounding like Eeyore (the donkey from Winnie the Pooh)confessing how he sits at home. Jerking off to porn and spending all of his money on phone sex. When he told me how huge his porn collection I busted out laughing. In fact, my stomach would be sore after giggling so hard it was like a 30-minute abdominal workout. As always this would make Mikey even harder. Sometimes blow his sad spew.

Throughout the years, Mikey had changed

No, he didn’t gain his manhood. He never was a man and never will be. He has finally accepted that. Mikey is now a full blown panty wearing, glory hole cock sucking faggot bitch. I mean, if you are not man enough to get a woman, you may as well be trained to suck dick.

He used to tell me he would never be turned into a sissy, never even think about putting a cock in his mouth. He still calls to this very day. In fact, I just introduced him to Mistress Brighton.

Another pathetic pussy turned. Go Casey go!!

So to all of you out there who ask, “Mistress, am I always going to be this way?” Yes. Yes, you are.


10 comments to Once a Loser Always a Loser

  • mike

    i know any female i get i alway want her to control and domanite me and punish me with spanking

    how do you feel about guy who love and alway want spank or female to give them spankings

  • Casey

    I am glad you know your place, Mike. 😉 I feel that men who beg for spankings, are whiny little bitches who deserve to be spanked. I absolutely love tuning an ass into pretty colors of reds and purples.

  • mike

    thanks you Miss Casey my ass would love being pretty color of red and then deep Purples as you laugh i alway know my place when female like you is around once i see them i jump in line the bheave line i dont beg for spankings well try not to i know i desver spankings or be place over knee or bend over for them from female i make angry

  • LOL Ms. Casey losers are so fun and can always be amusing! Mikey sounds like a wanker loser I have. They can’t keep their stubby little fingers off their loser peens lol. Why they insist on dating I have no clue other then they are gluttons for punishment and love the humiliation that comes with the rejection! LOL

  • mike

    LIsa if you female were not so hot and tempting in your way we be able keep stubby fingers off loser peens or give our penis attention we be better off but iam willing accept punishment from you or any female if i disobey or female is not please with me but punishment from them or they punishing me please them smile on their face while spanking going on i will admit iam a wanker loser i do touch myself alot so spank me

  • I didn’t even realize just how much of a pathetic loser Mikey was until I got on the phone with him and he confessed that you had turned him into a glory hole, cocksucking, panty wearing sissy, and when he got us both on the phone and you totally outed him for trying to withhold just how much of a loser he was, I had a good laugh. He really tried to convince me that he wasn’t a cocksucking loser, which made me laugh even harder. Thanks for posting this, Casey, he is hilarious!

  • Ha! Now Mikey, you should count yourself lucky that we Ladies give your sad useless peens any attention. But to be honest whether we did or not you’d still be unable to keep your stubby fingers off of it lol.

  • mike

    Ha Miss Lisa i will not use my stubby fingers not sure how u know the stubby i just use my tongues or some other object rub my penis with or use female panties. i know no female would want give my penis attenion now my balls iam sure would along with my pale white butt you free join in my torture any time want Miss Lisa i bleong to you as well

  • mike

    Miss Lisa and Miss Casey i feel lucky real lucky when any female pay me attention tell me what they would do to me as well too real turn on in sexy voice or hear them sayi been naughty boy and hear word spanking how you both will give me something i should had long time ago a good old fashion spankings so will you please both spank me over your lap double times

  • cuckoldscottie

    M-Mistress Casey, th-thank You for allowing me to respond to Your post, Mistress. i kn-know first hand the need for a Mistress to spank Her bitch bois. As my Cucky Sitter, i know that You need to keep discipline over me while my Wife is out with Her man, or over at his place for the night or week-end. i am obedient to both Her and You, but i know that should either of You decide to discipline me, i would be stripped *blush* and spanked *whimper* as long and hard as You or She think necessary, Mistress Casey. If You think i need a spanking, then i must deserve it, and i’ll try to be a good boi and keep still while You teach me a lesson, Mistress, and thank You for Your correction.

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