Category: sissy slut phonesex

Stripping Lessons

Avery 1-844-332-2639 ext. 228

One of my favourite sissies recently asked me for some stripping lessons. He lets me do whatever I want to him and dress him however I like, so I figured it was only fair to fulfill his wish.

I wasn’t sure if he would ever actually go through with it until the other night when he called me and said he needed some Avery time. He then asked if after I make him femme he can have his first stripping lesson. Absolutely, I said! I told him I was going to take him out and to come over around 4 pm so that I could get him ready.
Continue reading “Stripping Lessons For A Shy Sissy – Part 1” →

Sissy Mistress Janine 1-844-332-2639 ext 462

I identified him for what he truly was the moment I laid eyes upon him.  It existed in the sway of his hips, the delicate manner in which he held his hand out, and the soft, effeminate tone of his voice.  First, I let him know that I knew his secret even if he wasn’t aware of it himself.  Then I tucked his hand into the crook of my arm, patting it reassuringly.  I told him to put himself in my very capable hands.  His sissy training started right then and there.  When he didn’t put up even a little bit of resistance, I knew he was truly ready.

Continue reading “Sissy Training with Mistress Janine” →

Stephanie 844-332-2639 Ext 454

Pt. 1

“Tami, Mommy Stephi’s got a special surprise for you!” I said walking into the nursery. “special surpise? Oh Mommy Stephi whats the surprise?” I could already tell by the sound of her voice Tami was extremely excited. I smiled, a devious grin on my face. Sissy baby Tami had no idea what was in store for her. 

“Oh you’ll see baby Tami, but we have to get ready to go, the surprise is located somewhere else…” I giggled slyly. “lets get you ready to go” I said walking over to the changing table. I grabbed the diaper change bag and started to pack all the necessities. “I don’t know Mommy you seem to be very secretive about this surprise. I think you may be planning something bad.”

I laughed “you’ll just have to wait and see Tami, I’m not going to ruin the surprise.” After picking out a cute purple dress and purple socks I laid a very fussy Tami onto the change table to get her ready to go. 

“Mommy Stephi, why do we have to travel for the surprise. I wanna know I wanna know now!” Tami started fussing more, she just had to know what Mommy had in store.

Continue reading “Sissy Baby Tami & Mommy Stephi’s Secret Sex Dungeon” →

ABDL

Anna 844-332-2639 EXT. 203

Mommy Anna had brought Tami back to the nursery. She placed Tami in her crib and as Tami laid there all happy to be back in her happy place, she gazed up at what Mommy had left her with; a spinning mobile. But this wasn’t just any mobile, it was adorned with cocks all around. Big ones, small ones, BBC’s. Tami gazed at them in awe.

Continue reading “1 on 1 ABDL with Tami” →

sissy

Amber 1-844-332-2639 ext 404

In the early days, before we truly peeled back the layers of each other, his fascination with my past was almost insatiable. It wasn’t a judgmental interrogation, but a soft, probing quest for intimacy, as if understanding my pussy’s history was the key to understanding me.

“Your First boyfriend. What was his name?” he’d ask, his voice a low hum against my ear as we lay tangled in sheets, my fingers tracing the line of his jaw. I told him, a name I hadn’t thought of in years. He listened, rapt. Then, “How old were you when you fucked him for the first time?” His eyes searched mine, not for shock value, but for the story behind the number.

Continue reading “his fascination with my past” →

Mistress Janine 1-844-332-2639 ext 462

The only way you’re getting into my panties, sissy, is my doing my laundry.  First, I’m going to dress you in a proper service outfit.  You’re destined to be my service sissy maid today.  Now that you’re dressed properly, you can start your chores.  Gather up all my dirty clothes and take them to the laundry room.  That’s a good girl.  Make sure you sway those sexy little hips as you walk from place to place.  It’s important to practice being alluring.  You won’t get a real man with unsexy hips.  When you lean over the edge of the washer, be sure that your skirt flips up to show off the panties you’re wearing.

Continue reading “Janine’s Service Sissy Maid” →

Stephanie 844-332-2639 Ext 454

Pt. 1

I had only just started my job as a secretary three months ago when my curiosity got the best of me. Working at the office was great but there was something about my boss I just couldn’t put my finger on. Tim seemed so dominant and in control but I was convinced he was a total submissive sissy slut. 

I wanted proof and so I slipped into his office after he left for lunch. I started going through his office desk when I found undeniable proof. A fucking pacifier? Yes a pink little paci, I giggled staring at it before tucking it in my purse. 

That weekend there was a work related dinner party at Tim’s residence. Dinner and drinks, the perfect setting for me to set my trap for my closet sissy boss. I slipped something into his wine glass when he looked away, too busy gossiping with his many other secretaries. Gossiping, just like a woman, I giggled watching him take a drink from his spiked glass of wine.

Continue reading “Sissy Baby Tami’s Popped Cherry pt. 1 & 2” →

Steph

  Stephanie 844-332-2639 Ext 454    Anna 844-332-2639 EXT. 203

Mommy Anna was hanging out with Mommy Steph. Anna approached Steph and confided in her, telling her that she hadn’t seen Tim in a few days at the office and she began to suspect something was wrong.

Continue reading “Tim to Tami once and for All” →

Rachel 1*844*332*2639 Ext 457

He wanted to be one of us. At first, I thought he wanted one of us. He kept staring at us and our little outfits. I thought he was lusting over us. But he was really lusting over our outfits. He finally asked me how to apply for a job. After I explained the process, he asked me if he could try on my outfit. I giggled because I didn’t think that he was really serious. But then I realized that he was. So I had a plan. I told him that he could come over to my house to try it on.

When he got there, I not only had my work uniform, but I also had lots of lingerie ready for him to try on. He looked like a kid in a candy store when he saw everything. First, he tried on the work uniform. He wanted me to take some pics of him. I agreed, but I never knew that he was going to want so many. He told me that he had a large social media following. So I helped him get dressed up in lingerie like the little sissy that I knew he was.

Continue reading “He Wanted To Be One Of Us” →

Mistress Janine 1-844-332-2639 ext 462

Confess to me, sissy.  Tell Mistress Janine exactly what you’re craving and need.  He came into my office with a shy look on his face.  I asked him to sit down.  Then I assured him my office was a safe place to admit his desires.  He leaned across my desk and whispered low and slow.  I crave dicks to suck.

I leaned back in my chair and smiled at him across the desk.  Then I told him he’d confessed to the right woman.  He’d complete his transformation into his true self with me.  I stood up and came around the desk to take his hand.

Continue reading “Sissies Confess Their Desires to Me” →