Category: sissy phonesex

                                 young boy                                   Anna 844-332-2639 EXT. 203

Miss Anna had gotten a new neighbor. He was a tall, dark, handsome man and had a young son, who was in his 20’s. He often worked long hours, but Miss Anna would try and catch him any time she could, while gardening outside, smoking, or simply bringing in her groceries. One day, that tall, dark handsome man had to go away for a couple days and asked Miss Anna if she could watch over his son. Simply pop in to say hello, make sure he was going to school and eating properly, as well as doing his chores.

Continue reading “Miss Anna’s newest recruit” →

Mercedes 1844-332-2639 Ext. 423

Some days your sissy self may feel a little down, and there may be a day you won’t pick up the makeup brush…. But don’t you worry, I can make sure to help you feel as great, and beautiful as you deserve. Maybe you were looking forward to going shopping, but couldn’t muster up the courage to go out and look your best. Well, let’s put on that make up together and start turning heads, cutie!!!

Continue reading “Encouragement for Sissies” →

Sherry 1844-332-2639 ext 399

I whispered into his dreams putting him at ease. As I turned him into the little girl he wanted to be he giggled even though my friends startled him. He was still happy. I looked over to my son when he finished twirling I said Baby your girl’s name is going to be Tiffany. Today is your birthday to become a little girl. How do you like your new name? Tiffany ran to me with open arms, giggled, and just gave me the biggest hug and said thank you, Mommy, I love my name.

Continue reading “Chronicles of Sherry- Training Day – Part II” →

Miqala 844-332-2639

Every PSO has calls they really enjoy. I had an amazing call recently, and I want to share. I love Breastfeeding my Baby. Sometimes I get babyboys, other times, babygirls. My recent call was a babygirl.

He came to me as a man, so I started by stripping away his clothes one item at a time. Reminding him how I am stripping away his adulthood and his manhood. I could feel him surrendering to my soft Mommy voice, his voice becoming softer and lighter, and I started seeing the babygirl coming out.

Continue reading “Breastfeeding my Baby” →

Mila 1-844-332-2639 Ext. 220

As I am sure most of you noticed, I was on a little vacation! And to nobody’s surprise, I never stop hunting for a silly little boy to play with. Where do I look for these boys? Everywhere! You know the drill. But of course, I had to take a little trip to the beach for some me time, and I can spot a sissy from anywhere. Her little bikini did a poor job of hiding her little clitty! Sissy sluts in itsy bitsy bikinis get me going, of course. So I was going to have my fun! I ended up being able to lure her to my towel quite easily.

Continue reading “Vacation Specials For Sissy” →

bob

Anna 844-332-2639 EXT. 203

I called my Sissy Slut Bob over. I patted the bed and signaled for him to come sit. ‘’What is it, Mommy Anna?’’ said my Sissy Slut. ‘’We’ve been invited to a Swinger’s Party, and you’re going. I’m going to dress you up in something special, because I have to show you off as MY Sissy Slut. Sissy Slut Bob became overjoyed. I reached into my boudoir and dressed my Sissy Slut in a mini skirt, fishnet stockings, high heels, a top to match,  and my Sissy Slut’s favorite dark-haired wig. The top was patterned with upside down pineapples, the known symbol of swingers.

Continue reading “Sissy Slut Bob’s Swinger’s Club Party” →

Sherry 1844-332-2639 ext 399

It’s in the middle of spring walking along the parkway. I am wearing a stunning purple strappy sundress and tan wedged heels. My hair was all curly and pulled up in a sexy bun wearing my glasses. I can smell the manly musk in the moonlight air, wondering where it will lead me too. The night is still so young, should I give in to my urge or should I wait?

 

Continue reading “The Park Bench” →

Rita and Avery Put You In Panties

Robotic Rita 1844-332-2639 Ext 413

As soon as Avery and I discovered you had a tiny little stiffy, we forced you into panties. We couldn’t stop giggling because you were so flustered and nervous by two hot brunettes pushing you around. It was easier than it should have been, honestly.

When Avery said you were cute and I touched your arm, we almost thought you would cream your undies before we put you in panties. It was my idea to peel off Avery’s panties; I just slinked them down her legs under her short skirt without revealing any of her sweet pussy. Even though you wanted to see it so badly! You know you’d never even have a chance with either of us, so you let us bully you!

Continue reading “Rita and Avery Put You In Panties” →

Dinner Feast

Posted 6 months ago by Writer

Sherry 1844-332-2639 ext 399

It was a brutal day at work and I needed some stress relief.  I decided to gather my friends for a dinner feast.  I picked up sushi and some other finger foods to enjoy. When I got home, carried all the groceries in and called my little pansy to come over. I started thinking about the dinner feast as I got in the shower.

Continue reading “Dinner Feast” →

Summer Fun

Avery 1-844-332-2639 ext. 228

I am so ready for some summer fun this year! And since it’s officially summer that means you need some sissy dress up time so we can update your wardrobe. It’s the time of year for pretty summer dresses, bikinis and super, tiny shorts. Just think about how many guys you could attract by showing off those sexy legs of yours.

Do you wish a pretty girl like me would dress you up and teach you how to be a sissy slut? One of my favourite things to do is totally transform someone from a masculine guy into a pretty woman. I mean, you won’t be as pretty as me when I’m done with you, but you’ll definitely be passable once I work my magic.
Continue reading “Summer Fun With My Sissies!” →