Category: Sissy Training Phone Sex

Sissy Phone Sex with Brooklyn: Boxers or Panties?

I am a size queen because I am a Goddess; because I am perfection. Look at me. You can recognize perfection when you see it. So why would you for a moment think I would want to fuck you if you are packing less than 8 hard inches in your jeans. If you are lacking in inches then you belong in a pair of my pretty panties. I make no exceptions. You got to give me something I can feel.  And, for me, that is more than what you have in your pants, isn’t it?

Take a peek. I bet I am right. My last caller thought he could fuck me with 5 inches. Really 5 inches? The dumb ass thought 5 inches was above average. Maybe for a garden gnome, but not a man. So I told him to go put on some panties because he did not deserve to be in boxer briefs. He is a good sissy. He put on his girlfriend’s panties and sent me this pic. Now this made me smile.  A clit stick belongs in panties, especially pink panties.

I love a caller or a guy who doesn’t fight; who gets his place and accepts it. I mean a sissy is pathetic, this is true. But, there is nothing more pathetic than a dude with a clit stick who is convinced he can please a woman. Do you know your place with me? I am a dominant bitch size queen and I live for small dick humiliation and sissy phone sex.

Cuckolding Phone Sex with Brookyln and Marissa: Training Our Sissy Brother on Family Vacation

I don’t come from a big family. I have my brother and my sister Marissa. The girls got the looks in the family and the kick ass bodies. Our brother didn’t fare so well.  He has the tiniest dick ever. It’s not even a dick. It’s a clit stick. Our parents are deceased, but as siblings we try to do a family vacation each summer. The three of us went to Aruba this year. Marissa and I love our brother and he is incredibly wealthy. In fact he pays for the vacation every year. But every year he also tries to fuck his sisters.

Marissa and I are both goddesses who understand size matters. We love him, but we can’t fuck him. Regardless of how much money he spends on us. We always tell him he should feel grateful we are even seen with him.  I mean really, he should be. He has a big wallet yes, but that is the only thing big about him.  We were walking around the beach together and he was in a Speedo and I swear even the native islanders were looking at him and shaking their heads. They knew there was nothing in his bathing suit.

On the last night of our family vacation, we all went clubbing. Marissa and I picked up two well hung studs. I mean there was likely 36 inches of pure man between the two of them. We brought them back to the suite to fuck. Marissa and I share real men together on occasion.  And these were two real men. The problem was our brother. He is delusional at times and thinks just because he is family and has money, we will eventually fuck him. We did not want him to ruin our good time, yet we also wanted to send a clear message that small dick guys have their place, it is just not in our pussies.

Marissa and I decided we would make our worthless pecker of a brother watch while we entertained each other  and our two studs. I got him drunk, and we brought him back to the room where Marissa tied him to a chair with her panty hose. We then paraded our studs in front of him. We pulled out their cocks and told him in unison, “This is what we deserve.” His eyes got wide with disbelief. Honestly, I don’t think he thought cocks came that big. Our fuck dates were enjoying the fact that we had him tied up and in girl panties no less.  Marissa’s idea. She told him, “Clit sticks belong in panties.” I thought our brother was gonna die of embarrassment when he saw us swallow those big cocks in front of him. One of the guys said to him, “I hope you didn’t think these hot bitches would waste their time with you.”

He did, but we didn’t. We fucked like porn stars in front of our brother. We took those big dicks in our cunts, mouths and asses. We shared the cocks too as sisters share everything. We even licked the cum out of each other’s pussies telling our brother that real men have tasty cum and big loads. Marissa went to kiss him and spit a little of that man batter in his mouth. He was red from embarrassment.  We fucked our well hung companions and each other all night long. And we made our brother watch and stay tied in that chair. He even peed himself. Such a pathetic sissy.

The next morning after we said goodbye to the real men, we untied our brother. Marissa explained to him that although we loved him, and appreciated the vacation he took us on, he had to understand that as goddesses we have standards and he just doesn’t measure up. We were prepared for an onslaught of sissy histrionics, but he said he got it. Seeing those big thick cocks and how well they fucked us, made him understand our worth, our needs. He promised to never try to fuck us again. In fact he suggested next summer we take a vacation to an island with nothing but big dick so he could watch us get what we deserved all the time. Marissa and I couldn’t believe he was finally seeing the light, but he was.  

Between now and our next sibling getaway, he promised to learn about fluffing. Turns out he wants to help us get the cock and pleasure we deserve. Our brother is now not only our sissy bitch, but our wing man on family trips. He promised to help guide big cocks to us and in us! This may have been the best family vacation ever.

Sissy Phone Sex Training with Brooklyn: Are You a Man or a Sissy?

Sissy training phone sex is one of my specialties. I have a new sissy in training named Wendy. Doesn’t she have the cutest most pathetic little clit stick you have ever seen? Her little clitty belongs in my panties, not my pussy. I am a hot size queen and I have to maintain standards. So, when a pathetic pin dick loser tries to pick me up, they go in my panties not my pussy. I explained to Wendy, that she could purchase some of my sexy under garments and wear them herself, but that was the closest she was getting to being “in” my panties. She loves to wear my garter belts because they help center her and make her feel like the pretty princess she was born to be.  See when you have a tiny pee pee, your only purpose on this earth is to amuse and pleasure me. You cannot pleasure me with  your pathetic pecker, but you can pleasure me by being my panty boy, my sissy bitch, my clean up boy or my fluffer slut. Some very special losers get to be all of the above. Look between your legs right now for me. And tell me, are you man or sissy? If you have 8 inches or more of rock hard meat between your legs, you are all man and get to fuck me. You packing less than that, you get to wear my panties and be my panty boy, my sissy bitch, my clean up boy or my fluffer slut. So what’s it gonna be?

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?

 

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!

Ho Down at the Bar

I am wearing that little black leather mini skirt with matching leather corset. A pair of lace thong panties underneath. I push you down on the couch and straddle you.  I tell you to undo my corset and suck on my titties.  You do of course, you want this, and you want to be my little sissy fagot.  I rub the now growing bulge under my skirt against your ever growing cock. I hold your head hard against my titties.  I grab your hand and shove it under my skirt.  You try to draw back.  I release my cock from the confines of my lace panties.  The head already wet with pre-cum.  I grab your hand again,”Fucking stroke my cock, you know why I am here!” I command you.  With a moan you grab the head of my cock and begin pumping it.  “Yes that’s it sissy, pump that cock!” I moan.  I begin to fuck your hand, fuck this isn’t enough. I stand up where my cock meets perfectly with your sissy mouth. You know exactly what to do.  You take my cock into your mouth, taking deep down your throat.  I hold it there choking you. You flail against my body, I then begin pumping in and out of that sissy mouth.  I pull out, flip you over, tear your pants off, spit on my cock.  Just then you scream for me fuck your sissy asshole. I thrust forward and fill your asshole full of my big dick. I grab the back of your hair and ride you. I reach around to grab your cock and I begin working your cock with my hand. Your moaning so fucking load a neighbor knocks on the door.  You tell me to be quiet it’s the black guy from down the hall. I smile and yell for him to come in. He just smiles and says,” I always knew your liked cock. Hmm what about this one?” He pulls out his big ass cock and starts fucking your mouth.  He’s ramming his cock in your mouth so hard his balls are just bounding off your face.  I’m still pumping hard in your ass then I shoot a load deep into your sissy ass.  Your neighbor takes his big black cock out of your mouth and takes my place fucking your sissy faggot asshole.  I get under you and have you slip your cock into my tight pussy.  Fuck I can feel him thrusting in you.  Soon you are both picking up your pace fucking harder and harder balls bouncing everywhere.  Then he screams at you,”Take my cum you little sissy fucker!” Then he buries his cock deep in your ass and let’s jet after jet of cum fill you sissy fucker asshole.  Just when he cums and so do you.  It turned you on so much to have some big black cock up your ass.  We simply leave you thoroughly used on your couch, cum leaking from your asshole.

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?

 

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.

Sissy boy on loan

One of my friends went on an all-paid vacation from her sweet Sissy Boy; and, she asked me to look after him.  I told him that his homework was to memorize all of the songs from Oklahoma!, one of my favorite musicals; then, I told him to meet me at my office.  When he got there, he took off his robe and had done exactly as I asked: he had on a pretty little yellow skirt and a pink top.  I bragged on his wardrobe choices.  Then, I told him to come out on the balcony…this is where he was going to sing his little sissy heart out!  He looked terrified and asked if anyone could see him.  I said, “Of course.  The people who have balconies and even the people below the building.”  I had to coax him, but he relented; I told him that I was going to tape his performance and send it to Mommy.  He cleared his voice and adjusted his hair…and he was ready!  He went out on the balcony and began with the title song; and, before long, he was prancing.  After he had sung the entire track of songs, he started making up his own.  I was so proud and rewarded him by touching his little clitty while telling him that he was such a good sissy, that Mommy was going to be so proud when she saw the video, and that Auntie Monika was so impressed!