Category: sissy phonesex

Punish My Pet

Posted 3 days ago by Kara

Kinky Kara 1-844-332-2639 ext 306

My pet Paul has been my submissive for a while now, and he knows if he disobeys my directions, there will be a price to pay. Today I will be punishing my pet, and he has no idea what I have planned. He arrived dressed in a white polo shirt and black slacks. I greeted him at the door with a devilish smile. Immediately, I’d instructed him to strip naked and drop down to all fours. I twirled a spiked collar around my finger as I watched. I looked down at my naked pet on all fours, unsure of what I would do to him as I bent forward, buckling the leather collar around his neck. I attached the leash and gave it a nudge. “Follow me, doggie.” Continue reading “Punish My Pet” →

maid

Anna 844-332-2639 EXT. 203

Mistress Anna was throwing a lunch party and told her slave to dress up as a French maid. ‘’Please, Mistress Anna, this is so humiliating!’’ said the slave. But Mistress Anna wouldn’t have it. She ordered him to put it on and he obeyed: a French maid’s dress, fishnet stocking and high heels. Just then, there was a knock at the door.

Continue reading “Mistress Anna’s Lunch Party” →

My Sissy Neighbor

Posted 1 week ago by Kara

Kinky Kara 1-844-332-2639 ext 306

My neighbor was a vibrant, loquacious sissy, with a knack for doing hair.  I’d invited him over to get me ready for tonight. My man was coming over in less than an hour, and I wanted to look my best. Once my hair was finished and I was feeling as fierce as I looked, we decided to play in my closet. I recruited my sissy to help me find the perfect sexy outfit for a night with my man. He loved it when I let him help me get dressed. I think he secretly wanted to be a designer as well as a hairstylist. Once we found the perfect look for me, I decided to surprise him with a little makeover of my own.

 

Continue reading “My Sissy Neighbor” →

Julie 1-844-332-2639 Ext 453

“Miss Julie, we need your help with the sissy scout fundraiser again.” I heard the desperation in the sissy scout leader’s voice, and I couldn’t say no. Besides, I always have so much fun with the sissy scouts. I couldn’t wait to hear about how they were going to raise money this time. It’s always something exciting. They’ve never done anything boring and common like selling cookies. But then I realized why the sissy scout leader was so desperate. She didn’t have a plan and wanted me to come up with the fundraising idea. That really got me excited and the ideas started exploding in my mind. And I had an idea.

A friend had recently gotten the listing for the old “Best Little Whorehouse in Texas”. She said it’s being rented out for events. Perfect! I thought. All it took was a quick call and the venue was secured. Then I had a sign made. It read “BEST LITTLE SISSY SLUTS IN TEXAS”. I was ready to put them to work. I just knew it was going to be the most successful fundraiser in sissy scout history.

Continue reading “Sissy Scout Fundraiser” →

Cory 1-844-332-2639 ext 407

My sweet‑talking, ever‑ready sissy confessed something to me recently. She confessed that she’d been dreaming about the feel of something firm and solid pressing against her delicate, eager asshole. Something like my 10″ strap-on. She explained that being pegged was a secret fantasy that had been bubbling beneath her perky tits and talented tongue for far longer than either of us cared to admit.

Without a single hesitation, I slipped the sleek, polished strap‑on from its velvet pouch and admired its gleaming curve. I slipped the strap around my waist, feeling the weight settle against my hips. The sissy, perched on the edge of the bed, clutched the sheets with trembling fingers. “I’ve wanted this so badly, Cory,” she whispered.

Continue reading “My Sissy Confessed She Wanted To Be Pegged!” →

My Pretty Sissy

Posted 3 weeks ago by Kara

Kara 1-844-332-2639 ext 306

There is just something about dressing up a sissy boy that delights me. I guess all girls loved to play dress up, but dressing up as sissies is so much more fun. Surely I could play in my closet, trying on all the sexy dresses and heels I’ve acquired, but I’d rather dress up my sissy boy. He gets so excited when I call him over because he already knows what to expect. Today was slightly different, but I’ve decided to surprise him once I’ve dressed him all up.

 

Continue reading “My Pretty Sissy” →

Amber 1-844-332-2639 ext 404

The night I first saw my new little sissy girl, Chrissy, she was perched on a cracked stool with her legs crossed so tightly that she seemed to be holding herself together with nothing but sheer will. Her hair was a clumsy knot of pink and violet extensions and her makeup was more of an attempt than it was a success. She had thick eyeliner that drooped, lipstick that was smeared, and her blush was in all of the wrong places. Her too‑small dress clung to her body like a second skin. She was, indeed, a bit of a hot mess.

We got to talking and she nervously asked me the magic question that all of my sissy girls eventually ask. “Do you think you could help me become beautiful?” There was something raw in the way she asked, though. She was very clearly yearning to be seen by a different kind of audience. She wanted not just beauty, but the kind of beauty that opened doors. The kind that turned the heads of men whose pockets were fatter than their morals.

Continue reading “Sissy Chrissy Wants To Be Beautiful” →

secretary

Anna 844-332-2639 EXT. 203

Mistress Anna hired a new secretary. He was overqualified, and very capable, but most of all he wanted to work for Mistress Anna more than anything in the world. She said she expected him to act, work, and dress a certain way. Without even asking, he agreed to all the terms.

Continue reading “Mistress Anna and her Secretary Slut Slave” →

Cory 1-844-332-2639 ext 407

There I was, perched on the edge of a plush velvet sofa in Kayla’s living room. Sammy, our sissy girl was excitedly describing the man she’d chosen to marry. He was a team lead at her workplace and he already had a fiance, but that wasn’t going to stop Sammy. Especially, with Kayla and I there to encourage our little homewrecker virgin whore.

As Sammy talked about how she could see the shape of her future husband’s thick cock through his dress pants every morning, Kayla nudged me and whispered, “We should help her choose her bridal lingerie for the wedding night her pussy will never forget!” I laughed, because even just the thought of our sexy little Sammy bouncing up and down on that cock in virginal lingerie was deliciously mischievous in and of itself. “You’re on, babe,” I whispered back.

Continue reading “Sissy Bride Sammy Steals A Husband” →

Kayla Cumsalot 1844-33-CANDY ext 357

My sister is getting married this year, and I get to be her maid of honor! With us being in different states, it’s been hard for me to decide on a dress that will match her other bridesmaids’ gowns. She asked me to go to a bridal shop here in Vegas and send her some pictures of the dresses I tried on.

Off I went to this fancy smancy bridal shop downtown with my friend Terri in tow. Terri is five feet nine inches tall, TRANSGENDER female with a cock that most men would envy. She’s very masculine in appearance but identifies and dresses as female.

Continue reading “Trying on Wedding Dresses for a Sissy” →