Tag: sissy

Julie 1844-332-2639 Ext 453

Josh and I were assigned the task of planning the company brunch. We had become close friends over the past several months of working together. I invited him over to brainstorm and come up with the theme for the brunch. We work well together, and within no time we had the perfect plan. Ready to celebrate the completion of our project, we decided to order a pizza, and have some drinks. Soon we were deep in conversation and confiding our innermost secrets. He confessed that he and a coworker had been flirting. He had a major crush, and needed my help. He wanted me to teach him how to suck cock. So we went into my bedroom and I gave him a lesson on a variety of dildos. By the end of the night he was an expert. Continue reading “The Company Brunch” →

Diana  1-844-332-2639 Ext. 248

I was reminiscing about my first sissy recently. There’s something undeniably seductive about exploring power dynamics in a relationship. For me, stepping into a dominant role with a partner isn’t just about control—it’s about trust, vulnerability, and the intense connection that blooms from those moments. One of the most exhilarating experiences, the first time he wore panties, often makes me smile. There’s nothing hotter than kinky twists on traditional roles.

I won’t lie, watching him surrender his masculinity to me was beyond thrilling. I picked out a silky pair of pink panties, with delicate silk flowers embroidered on the edges. He whimpered as his cock felt the soft fabric for the first time. Continue reading “My First Sissy” →

Girl Talk Confessions

Mama Felicity 1844-332-2693 Ext 270

One of my favorite types of calls is girl talk confessions! I love hearing what you naughty boys do when you’re dressed up as sexy sissies. Some of you are filthy sluts, and your stories leave my jaw dropped!

A few of my lovelies likes to call me while getting dolled up. As they roll up their stockings and clip on their padded bras, they dive into the slutty details that they can’t tell anyone else. I mean, hello, who else but me knows how much of a sissy whore they are? Just the John’s they swallow, I guess.

Continue reading “Girl Talk Confessions” →

Body Envy

Robotic Rita 1844-332-2639 Ext 413

Oh, you have a bad case of body envy! I mean, it reeks. Most men look me over with sexual desire, but the green-eyed monster shines through your gaze. You don’t want to fuck my face or impregnate me. No, you want to be me. It’s obvious; I don’t understand how you’ve managed to hide your secrets from your wife for so long.

Is she just stupid, or does she not care about you at all? All the signs are there. Why can’t she see how badly you want to be a woman?

Continue reading “Body Envy” →

Zesty Zoey 1-844-332-2639 Ext 403

I love shopping with my sissy.  It’s so fun to find outfits and accessories to turn you into the most perfect feminized sissy you can become.  We’ve spent hours together training you up.  You’ve learned how to be a good little cock sucker.  So, now you’ve earned a reward.  It really does pay off to suck cock like a champion.  You’ve worked really hard to emulate the behaviors of a proper sissy.  Now it’s time to make you look like one.  It’s sissy shopping spree time!  We’ll go to all the best stores and shop together for some sexy little outfits for you to complete your transformation.

Continue reading “Shopping with My Sissy Phone Sex” →

Sissy Jerk Off Competition

Mama Felicity 1844-332-2693 Ext 270

I love getting my sissies together and making them compete for my attention. Not only is it entertaining for me, but it amps up the humiliation level of both bimbos. Yesterday, I brought in two girls who didn’t know each other. Sissies meeting for the first time is so cute. They try to be polite, but each has a hidden agenda. Wanting to be Mommy’s favorite girl.

Jessy and Britney, dressed in matching lingerie sets (minus the panties) and tall heels, stood in my living room as I lounged back on the couch. Jessy’s clitty was bigger and harder than Britney’s as it stood out proud and tall from under her garter belt, but I know Brit has a quick trigger clitty, so the jerk-off competition was going to get interesting.

Continue reading “Sissy Jerk Off Competition” →

Naughty Naomi 844-332-2639 ext 216

Welcome sissy faggot, it’s time to start your training.  Do you know the best place to properly train a cock sucker like you?  My favorite place to take you to practice is the local glory hole.  Tonight is glory hole training! But first, we have to get you presentable.  Guys aren’t going to want to get their dicks sucked by that. *waving vaguely at you

So, it’s time to femme you up a bit.  Time to do your hair, make up, and to dress you like a proper slut.  I’ll transform you into something men want to stick their dicks into and get off.  Pout those lips sissy, time for that lip gloss so your lips slide smoothly up and down the cocks you suck tonight.

Continue reading “Sissy Faggot Glory Hole Training with Miss Naomi” →

Zesty Zoey 1-844-332-2639 Ext 403

Welcome to Zoey’s University of Femininity!  Things are going well with the development of my training program.  My first set of students has gotten off to a great start.    From sissies to fembois, no one is turned away.  If you’re willing to put in the time and effort to learning how to become your best feminine self, there’s a place for you here.  So many classes to reach your feminizing goals.  I know you’re going to find exactly what you need and are looking for here.  Classes are offered in fashion, deportment, and even improving any and all sexual activities.

Continue reading “Zoey’s University of Femininity” →

Mommy's New Office Secretary

Mama Felicity 1844-332-2693 Ext 270

Awe shucks! My secretary quit on me at the last minute! I have an incredibly important board meeting with the founding female committee members today, and I will need a second pair of hands to take notes and keep everyone on task! As we all know, finding good help is near impossible these days, so I’m going to have to turn you, my little submissive loser, into my new office (sissy) secretary!

I’ll dress you in the whole nine: thick, suntan nude pantyhose, a pencil skirt, heels, of course, and a button-up blouse. A blonde wig so no one knows who you are and, of course, lots of makeup to define your feminine features. Hurry and get ready. You don’t want to be the reason we’re late to the meeting and then have to explain to the other ladies, do you?

Continue reading “Mommy’s New Office Secretary” →

 

Triggering TSA

Mama Felicity 1844-332-2693 Ext 270

Summer is nearly here! I’ve been dreaming about taking a tropical vacation with my favorite sissy, and now is the time! I booked a quick trip to Jamaica and had my girlie pop meet me at the airport. Of course, she was still caged, and the key to said cage dangled from my throat. “Can we unlock me before we go through security?” She wrung her hands together in front of her nervously. Her metal clitty cage would sound the alarm and trigger TSA to do a further investigation. My head shook as I looked at my watch.

“We don’t have time. We’ll just have to chance it and hope for the best.” Her shocked and worried face gave me tingles. I love publicly humiliating her, and as we stood in line waiting with our passports in hand, I KNEW this would be the best way to kick off our vacation.

Continue reading “Triggering TSA” →