Category: sissy phonesex

Trinity 1-844-332-2639 ext 285

When I say The Interview: Breaking In My New Sissy was unforgettable, I mean it started the moment he knocked on my door—nervous, dressed like the desperate little toy he is, and already dripping through his cage. He wanted this. Begged for it. Said he needed to be broken in properly, to be humiliated, used, trained. I just smiled and set the stage.

“Let’s pretend you’re applying for a position,” I told him. “Personal assistant. Required skills: obedience, silence, and taking it like a good little sissy.” He showed up wearing a tight button-down barely covering his lacy pink bra, a black mini skirt, and kitten heels he could barely stand in. His lips were glossy, cheeks flushed, thighs trembling from the plug I’d told him to keep in all morning.

I let him stand there like a fool while I looked him up and down. “This is what you wear to an interview? Pathetic.” He tried to answer, but I cut him off. “Strip. Now.” He did, shaking the whole time, until he was standing in front of the mirror in nothing but his cage and his shame. I circled him like prey, tugging the leash I’d clipped to Continue reading “The Interview: Breaking In My New Sissy” →

behave

Anna 844-332-2639 EXT. 203

Mommy woke up early and made sure to feed Sissy Baby Tami her formula. Only it wasn’t regular formula, but a concoction mixed with laxatives, hormones and aphrodisiacs. When Tami was done her bottle, Mommy gave her another bottle of formula, then another. She wanted to make sure Tami was over the moon horny, happy and full. Tami told Mommy that the cupboards were bear and so Mommy decided it was time to go grocery shopping but she made Tami promise she would behave.

Continue reading “Sissy Baby Tami goes to the Grocery Store” →

The Whole Gym Knows

Goddess Rita 1844-332-2639 Ext 413

Oopsie! I forgot today is back and bi’s. Sleeping through my alarm had me darting out of the house without a single thought other than how late I was for work. It completely slipped my mind that I’d forgotten to unlock Michael’s cock cage this morning. Michael is a good sub and rarely complains except when he has to wear his cage to the gym.

Because he is so good, I compromise, and every Tuesday, Thursday, and Saturday morning, I unlock his cage before I leave for the day. He hits the gym (to keep his body perfect for me) and stops by my work on his way home to get his cage back on. Today, however, I was scheduled for meetings that I was already late for and there would be no way for me to unlock Michael before his workout and this is how the whole gym found out the fittest dude in the gym wears a tiny pink cock cage for his Goddess.

Continue reading “The Whole Gym Knows” →

roommate

Anna 844-332-2639 EXT. 203

Miss Anna took on a new roommate. He was very shy and quiet, but she always secretly had the hots for him. When night fell, she could swear she heard him stroking away in his room. She was so tempted to knock on the door and ask if she could lend a hand.

There was of course, one thing that really bothered her about him: Every time she went out and came home, she noticed that things from her room would be misplaced. Her shoes, her clothes. She confronted the roommate, asking him if he had guests over. He claimed that his girlfriend had been by and was fixated by her closet, to which Miss Anna stated she didn’t mind, so long as his girlfriend put everything back where she found it.

Continue reading “Miss Anna’s Roommate” →

Crossdresser Caught In My Closet

Goddess Rita 1844-332-2639 Ext 413

My roommate decided to throw a house party. She promised it would be like ten people max, but the house was crowded when I got home from work. Loud punk music played through the speakers, and before I could even push through the door, I had to shove through a cloud of stoner smoke. To say I was angry was an understatement. Finding her through the horde of people would have been impossible, so I stomped my way up to my room.

Honestly, I half expected to walk into some random couple fucking on my poor bed but to my surprise, my bedroom door was shut and it was quiet on the other side. I flicked the lock and threw down my things. Annoyed and exhausted, I moved to my closet so I could get out of my work clothes and at least be comfortable, but to my surprise, there was a crossdresser in my closet!

Continue reading “Crossdresser Caught In My Closet” →

Big Strappys

Avery 1-844-332-2639 ext. 228

Everyone knows that sissies love big strappys. And really, can you blame them? You’ve been a shy sissy for far too long, so it’s time to get naughty. We both know that you’re ready to let go and finally feel the real pleasure that only big strappys can provide.

I bet you’re sitting there now thinking about what it would be like to get really fucked, aren’t you? Well, I don’t blame you. And I’m sure that thinking about having me pound your ass with my fat strap on has gotten your little sissy dick hard. That’s how I know you’re ready to take it.
Continue reading “Good Girls Need Big Strappys” →

sissy girl

Posted 1 month ago by Amber

sissy

Amber 1-844-332-2639 ext 404

I smirk as I walk into the bedroom, my sissy girl already waiting for me on the bed. She’s wearing a tight pink dress that barely covers her ass, and her long blonde hair is pulled up into pigtails. I can see the nervousness in her eyes, but there’s also a spark of excitement. She wants this, and I’m more than happy to oblige.

“You ready for this, sissy?” I ask, my voice dripping with amusement. She nods, her cheeks flushed. “Yes, Mistress.” I chuckle, walking over to the dresser where I keep my toys. I pick up the sleek, purple device and wave it in the air. “This little thing? It’s going to make you scream, like a sissy bitch.” She whimpers, her hands clutching the sheets. I can see the wetness already staining the crotch of her dress.

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spoon

Anna 844-332-2639 EXT. 203

Mommy Anna was organizing a special birthday surprise for Sissy Baby Tami. After all, it was this little Sissy Baby’s birthday. She was going to be a year older, and all the more naughty, slutty and filthy! Mommy Anna was preparing things in the nursery. Mommy Kayla, Mommy Amber, and Mommy Zoey all came to set up the decorations, they managed to find the most poofy pink dress for Tami, with matching pink stockings and little Mary Janes, and let’s not forget Tami’s most favorite hair bow toe that was in a shape of a little mini cock barrette!

Continue reading “Happy Birthday Sissy Baby Tami!!! Pt. 1” →

Trinity 1-844-332-2639 ext 285

My favorite sissy was already kneeling when I walked in, hands resting in his lap like the obedient little doll he was. Silk panties hugging that useless bulge. Lips glossed, eyes wide, eager. My favorite sissy. “Good girl,” I purred, running my fingers through his wig. “You’ve been waiting patiently, haven’t you?” He nodded quickly. “Yes, Mistress.” I leaned down and kissed his cheek—soft, slow. Then slapped the other one. Just hard enough to make his lip tremble. “Speak when spoken to, baby.” He whimpered. God, I loved that sound.

I made him crawl behind me to the bed, swaying my hips just to watch him squirm. He was already leaking through his panties—so easy, so desperate. “Take them off,” I ordered, and he did, revealing that pathetic little clit of his. I giggled. “Oh baby… still small. Still so useless. But you’re so pretty, aren’t you?” I dragged my nails down his chest.

“You’ll never fuck me like a man. But that’s not what you’re for.” He moaned as I pushed him on the bed, straddling his face. “This is your purpose, slut. You serve. Must worship and satisfy.” I lowered my pussy onto his mouth and he moaned Continue reading “My Favorite Sissy” →

Diana 1-844-332-2639 Ext. 248

I received the most interesting letter today from one of my favorite submissives! I hope you enjoy reading about how he craves being my sissyslut whore!

“My dear Mistress Diana,

I come to you today full of yearning and desperation. Beneath the façade of the strong, confident man I must be, a submissive, aching need has been growing and consuming me. I am so tired of always having to be in charge, of never being able to truly let go and surrender control. My job demands a leader, but my body and soul cry out to be led.

Continue reading “My Sissyslut Whore” →