Category: Sissy Phone Sex

Sissy Phone Sex with Brooklyn: The Sissy Pity Fuck

I make no apologies for being a size queen. Look at me? Perfection. Beautiful body, gorgeous face and smart to boot. I deserve only the best in life and that includes cock. I have many men try to hook up with me. When it proves that they are nothing but a little boy, they become nothing more than a sissy or fluffer boy. Case in point, Sissy Christina below. Look at that pathetic excuse for a dick? You might have to get a magnifying glass to see it. That’s a clit stick at best and belongs in panties not boxers, or briefs nor even boring tidy whiteys. Hell, it should be in a fucking diaper at that size.

Well this particular Sissy is a fucking whiny ass bitch. Annoying as hell. Took years to break her and get her  to stop begging me to fuck her. Just about the saddest creature on earth. Why did I put up with her pleas and begging and overall pain in the ass antics? Because she is my brother and loaded. A computer software genius. What she lacks in dick, she has in brains. But no one wants to fuck just brains. It’s sad; I got both beauty and brains; she got just brains.

Ever since we were little, my brother tried to fuck me. I was the hottest woman he had ever seen. Well of course, when you are a short dicked ugly loser, women like me are not gonna fuck you. For 20 something years, my brother begged to bust a nut in his sister.  And, one night, in a total moment of weakness and shear alcohol consumption, I gave him a pity fuck at a family reunion at a beach house in Florida. I didn’t want to be there to begin with, but our mother guilted me. So, I drank like a fish the whole week. On the last night, my brother who was in his 30s at this point, came into my room and started crying. He admitted he was a virgin. Yes, like the movie only a 30 Year Old Virgin.  The girl he was seeing for months and whom he thought was “the one” laughed and ended the relationship on the night they were about to fuck for the first time. An unattractive, book worm, troll of sorts even rejected his little baby dick. I was tired and he wouldn’t leave. He was just so fucking sad and pathetic. I caved.

I said, “I will fuck you this once. But you tell anyone and not only do I castrate you but I disown you. And it will never ever happen again.” He promised. I was still drunk and only have awake. He fumbled to get his shorts down and when he did, I swear I burst out laughing so hard I nearly cried. He got on top of me, oblivious to my laughter and obviously not accustomed to foreplay. But, that was fine, no way I was cumming. I kept asking if he was in yet. I mean I couldn’t feel it at all. AT ALL. Just his sweaty body on top of me and his grunts. I started counting in my head until it was over. I got to 6. Literally three strokes and he was done. He claims he came, but I didn’t feel anything but shame for having given in.

After that horrible night, my brother became my sissy. My first sissy actually. I told him he needed to give up on trying to get laid cuz he was just gonna face rejection every time. I explained there are other ways to please women. He can be a cleanup bitch; a fluffer boy; a procurer of big cock; a source of entertainment; a sugar daddy. But he could never be a lover. He has accepted his fate. He is the best sissy a size queen cuckolding mistress sister could ever hope for. Have you accepted your fate yet?

 

Scat and Fries

There’s nothing worse than having a boss that feels that they are better than or above you. In my boyish days I used to work at McDonalds flipping burgers and worked under the WORST manager imaginable. It got to the point where I quit the job and never looked back. Now, I’m in a totally different situation and feel as though I should give my last employer a visit. I parked across the street from his house and waited for him to finally kiss his wife goodbye. Apparently the bitch brings home the bacon because he didn’t leave the house all day! I got tired of waiting so I banged on the door and as soon as he opened the door a tased him in the neck. While he was on the floor pissing his self and screaming like a little bitch I dragged his ass upstairs. This fat bastard was going to find out what it felt like to be “below” somebody. He was kicking and screaming as if fighting back was going to help. I hit him again with the taser and zapped him right into submission. I told him to get on the bed and to not say another fucking word. With all my strength I tied his wrist and ankles to each end of the bed. With my 6 inch pumps I reigned over him and he knew I wasn’t meant to be fucked with! I’m surprised he didn’t remember me but either way he was gonna remember this day! I unbuckled my skirt and let my dick swing in front of him. His eyes got wide for he knew exactly what I planned on doing with it. For the next 8 hours until his wife pulled into the drive way I was stuffing him with my big black cock and making him my bitch. I spread his mouth wide open and made him scream out, “Ding fries are done Mistress” for my own entertainment. When I was done with this pathetic fry flipper, I pissed all over him and the bed he fucks his wife in. The sheets were stained with his ass blood and my pungent yellow piss. I made him swallow it, and open his eyes so that he could really feel the burn. I walked out of the house as soon as his wife was trying to walk in. I left without saying any words and let that cunt assume whatever she wants. As long as she knows that from here on out that I’m the boss!

Painful Lover

There once was a man named mike
That always wanted to put up a fight
When his cock got hard
And started to thumb just at the mere sight

The mere sight of a man named Tom
Who’s ass hole was too bomb
He sucked cock all night
Made mike feel just right
And brought him right out the closet!

Now mike goes by Mika
Instead of boots she wears stillettos
And got tits that jiggle like jellos!
She makes you worship her goodbar
And shake in fear in the car
On your way home
To the bitch you call “Dear”

But you can’t say that to mika
Anything other than mistress, madame, or master
Or else you won’t like what happens after!
She’ll bend that ass over
You’ll wish you had a four leaf clover
Hoping you’ll get some luck
And no longer be a cuck
Or gain mercy from this painful lover.

But, Mistress love’s you like no other
Nobody will make you beg like this
Or make you moan and hiss
From the pain and pleasure
From this 9inches to measure

So go ahead and grab some knee pads
And even a bottle of lube
Cus’ Mistress Mika forgot to add
She’s going to made you hurt real real bad!

You submit to me and no other
Unless you want to lose your painful lover!

Flashbacks of a Sissy Phone sex

Before I was the dominating Mistress that I am today I used to be just like you. A pathetic little fag boy jerking his cock at the thought of being owned and possessed. Not being able to control how much pain you get or how long you get it is the best part right? WRONG. For me I had to learn the hard way that shit was not for me. When I let my master from a previous life dominate me I was his bitch. I did everything he told me to do and however he told me to it. I loved my Master and he treated me like he loved me so I never went against him. However, one day during bloody anal play I was letting him stretch my asshole wide open until it tore apart. It hurt too badly after a certain point and I had to use our safe word to stop. The first time I yelled it I thought maybe he didn’t hear me. Wider and wider he was pulling my asshole apart and I couldn’t even stop him. With my hands bound to the headboard I screamed as loud as I could. That is when I knew he didn’t give a fuck. It did not matter how far he stretched my asshole, he wouldn’t stop until he killed me. I was in the hospital for 2 weeks going through anal reconstruction due to all the damage done. When I walked out of the hospital I walked out a new woman. A woman that would never bend over for another cock again. A woman with a vengeance!

Magic Sissy Phone Sex

I got the magic stick! I know that once I show a sissy or gay boy my magic wand they always come running back. When I swing this shit around for some reason everything I want magically appears. When I say the magic words, “open wide”, my bitch boy does as he is told while jerking away at his cock. I love learning new tricks and spells to make a sissy drop to their knees in submission. Just the other night I fisted my sissy so long and hard that I almost pulled the rabbit out of the hat! He loved the feeling of making my arm disappear while I reach deep down inside. What was I looking for in there? I couldn’t tell you but I know one thing.  I wasn’t coming out empty handed! My magic wand was standing straight up at attention as my arm appeared to be getting shorter and shorter. I wandered what else my special helper could make disappear. This is why for my final act I went balls deep down his slippery, wet, throat. For this trick, however, I was going to need to use extra focus if I was going to get it off (if you know what I mean). I had my helper lay flat on his back with his mouth wide open. As I squatted inch by inch my dick started to disappear. Before I knew it my asshole was on his nose and my cock and balls were getting the lick down of a lifetime! The end of the show was about to cum but not without making a mess. I made my sissy say the magic words, “Please let me have your cum Mistress” as I let off all over his fucking face. Damn, that really was a magical moment for the both of us.

Check Your Pride At The Door Bitch

I see right through your act, you look so masculine and strong but admit it you crave a sexy, sensual sissy trainer like me to humiliate your pathetic ass.

You had better be willing to check your ego at the door, because if you want me to spend my time with you, your pride is going to be shredded. Do you want to be my sissy lover, suck lots of cock, dress up in pretty silky, frilly dresses or watch your Princess get fucked by real men with really big, thick dicks?

I can train you in any and every aspect you crave most of being my little fuck toy. I bet you would just love it if I strapped you down and took control of your cock. Let me massage and milk that dick of yours, make you cum harder than you ever have in your life.

I can even show you the right way to masturbate with your sissy clitty and make you shoot a big load of creamy cum all over yourself. Does any of that sound like a good place to start, pet? Just remember, check your pride at the door and listen to my every instruction about how to be the perfect little “Fem Bot” for your sexy, sensual Princess Paris.

Small Cock Humiliation Phone Sex with Brooklyn

Look at me. I’m fucking hot as hell. See this dildo? I think that is on the small size for how I like my cock. Now look at the picture below. You may have to squint to see it. That is the pathetic wiener of a guy who emailed me today. Yes, some poor losers have clit sticks for dicks. It’s not even half the size of a toilet paper role. I was laughing so hard, I snorted ice tea out my nose. I’m a size queen and I make no apologies for needing big dick. I deserve huge cock. My husband recognizes that. Yet, I still get emails all the time from tiny dick losers with pics like this. This sissy boy at least was smart enough to know what was between his legs was nothing more than entertainment fodder for me. But some dudes be like, come on baby, you know I got what you need. If I need a good laugh, then yes, those ken doll pee pees, are just what I need. But if I need a good hard fuck, then I need something I can feel; something no smaller than my 8 inch dildo. My pleasure is not to be taken lightly. And a small one can’t give me pleasure.

The size of your dick determines how we play. Got a dildo sized cock, well I will be your bitch and suck and fuck that monster cock all night long. You got an itty bitty thing, well I am gonna laugh and share your photo with my fellow hot bitches who deserve big dick. Now, this sissy boy who emailed me today belongs in panties and a bra as he has a click stick. Cocks belong in boxers or boxer briefs or my mouth! But, little clits belong in little cotton panties with hearts or flowers on them! I’m gonna send my newest sissy boy to a lingerie store to buy something appropriate to wear. I wonder what I should make him buy? Any suggestions?

 

Attn: Mistress Levi’s Sissy

Dear Sissy Fairy Fag:
You know that you are running out of time, pathetic pitiful paypiggy! I remain optimistic that you will do as you should, little one.The generous deadline of Friday, July 18th is coming up soon. You know that it is your place to provide a luxurious vacation for Mistress Levi and her girls; this is not a request, but your duty for all the loving attention and humiliation that we provide. Otherwise, you will suffer serious consequences. Of course, you will be shamed on television and radio broadcasts. We will all hang up pictures of you everywhere, along with words that describe your unforgivable actions and demands that you be taunted whenever seen in public. You will not want to leave your house because you everyone will know about you. We will be forced to announce your sissy ways to the world; and your career and reputation will be completely ruined.  Perhaps most importantly, you will disappoint Mistress Levi, who will instruct us not provide you with the attention that you crave! So, please pay your dues and continue to be chastised, humiliated, and loved like you need to be by Mistress Levi and us girls; it would be such a sad loss for us if we could not ridicule our sissy whore anymore; so, please know your place and do what you are required to continue to be Mistress Levi’s sissy fairy fag and our beloved mascot!
Hoping pathetic paypiggy does what she should so she can remain our favorite sissy fairy fag!
Lacey

The Way It Is

In this world, my perfect round ass is the prize to be worshipped. Sissies like Goddess Levi’s pathetic pitiful paypiggy have to beg to be able to worship the ass of a Superior Female. You want to know something funny? This little tinkerbell fairy is being blackmailed by her Goddess into paying for our WBMT vacation! YAYAY! That means all of us girlies get to sit by the beach in St. Augustine, Florida and sip cocktails while dipping our toes in the water. Meanwhile, Levi’s blackmail piggy will be footing the bill for our oceanside rental house. It will be so funny to see the trepidation and nerves play out as she realizes that big consequences will follow if she does not pay up! This sissy fairy fag has until Friday, July 18th to send Goddess Levi all the money for our vacation. If she doesn’t pay up, our sissy can kiss her career as a big shot lawyer goodbye! We have incredible SEO rankings, and if all of us girlies blog about the identity of this pathetic pay piggy’s cross dressing antics and silly sissy ways, she will be ruined forever on Google! In fact, everyone looking her name up to try to find her law services, and they will instead learn the fact that she is a total pansy, fake-man who loves dressing up in pretty frilly lace clothing! This will be very funny to see. I can’t wait for the drama to play out. Will she be a good blackmail piggy and pay up for our vay-cay, or will everything come tumbling around her?! 😀 We will have to wait and see.

Prissy Sissy

I love it when my sweet sissy comes over to play. She loves to wear my prettiest panties and silkiest nighties. She will go through my entire closet and try on everything I have flaunting it and twirling around for me in her feminine way. She is such a prissy sissy! She loves to be my pretty girl, to have me put on my strap on and pull my pretty pink panties aside with her legs way up in the air and fuck her like the girl that she longs to be. Sometimes she wants to wear diapers and be my real little girl. She is so cute when she wants to be little like that for me. She will hold me tenderly all night long after we are done, caressing my hair and cooing my name. Thanking me for letting her be my sweet girl. Thanking me for letting her wear all my pretty panties and clothes. She is always so grateful for being able to be my girl. I really love my sweet little prissy sissy.