Category: sissy slut phonesex

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!

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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” →

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” →

spit roast

Anna 844-332-2639 EXT. 203

Mommy was determined to bring Tami back to the nursery, she grabbed Tami and carried her there, Tami twirled Mommy’s hair while being carried, and when they entered, Mommy made sure to shut the door, behind them, lock it and even double bolt it. Mommy brought Tami over to the change table and told Tami that she had to diaper her. No regular diapers for this baby, only plastic scrunchy ones, and Mommy put on little socks on Tami along with a pink, short frilly dress, that was short, one could see Tami’s diapies underneath if she so much as sneezed.

Continue reading “Mommy Anna brings Sissy Baby Tami back to the Nursery” →

sissy

Amber 1-844-332-2639 ext 404

My sissy, Stella. She keeps me constantly on my toes (and occasionally reaching for the headache medicine). Let’s be clear, I adore her. I truly do. But sometimes, dealing with her is an interesting process. Now, the allure of having a sissy is obvious, isn’t it? The delicate dresses, the painstakingly applied makeup and perfect hair, the eager-to-please attitude. It’s all very appealing, if you know what I mean. She’s a blank canvas ripe for artistic expression and lets me do anything and everything to her holes. And believe me, I’ve been expressing myself.

But here’s the kicker: my little darling? She’s still got a few…Um…Glitches in the system. There are days when she’s the epitome of feminine grace, fluttering around in fancy dresses and stockings and lace, batting her eyelashes with the precision of a seasoned professional. Then, BAM! Out comes the “boy voice.” You know, that deep, gravelly rumble that belongs on a construction site, not coming from a vision swathed in pink chiffon!

Continue reading “My sissy, Stella” →

Diana 1-844-332-2639 Ext. 248

My boyfriend Bob and I were dreaming of an epic vacation to Hawaii – thought we’d soak up the sun, sip Mai Tais, and fuck like a pair of honeymooners. It was going to be bliss!

But leave it to that dummy to go and mess things up for us. He got himself fired from his cushy office job. Can you believe it? I was furious! All my daydreams of palm trees and piggyback rides on the beach were dashed. So I decided to take matters into my own hands.

I had a plan – a deliciously wicked plan. Poor Bob was bewildered when I marched into the bedroom brandishing makeup, wigs, and a heap of slutty outfits. “What the hell is all this, babe?” he asked, eyes wide as saucers. I just smirked. “It’s time for you to pay for our trip, one way or another.”

Continue reading “My Boyfriend Bob” →

slave

Anna 844-332-2639 EXT. 203

Miss Anna wanted to go shopping, so she summoned her slave. He came diligently running. ‘’Yes, Miss Anna?’’. Come with me, she said. We’re going shopping, I need some new clothes. ‘’Yes Miss Anna, I’ll do whatever you say.’’ ‘’Wait!” said Miss Anna. You’re not accompanying me like that, put on some of my slutty clothes, that way we can match. ‘’Please Miss Anna,’’ her slave pleaded ‘’I can’t possibly wear that, Ill be so Humiliated!’’ ‘’That’s the whole point!’’ replied Miss Anna ‘’Now hurry up and put these on.’’ And with that, Miss Anna handed him a pair of fishnets, a slutty short skirt,  a tight-fitting top, and a bra and thong to wear underneath. She made him slip into her high heels and off they went.

Continue reading “Miss Anna’s Slave” →