Category: sissy phonesex

Jessica's First Breeding

Mama Felicity 1844-332-2693 Ext 270

There are milestone moments in every Sissy’s life that should be celebrated. Her first pair of panties, when she gets her first set of tits, even the first time she kisses a boy. All of these accomplishments should be shared in delicious girl talk with someone who supports her and always cheers her on. That’s exactly what Jessica and I enjoy together. I was with her in that sex shop where she got her first clitty cage. Over the years, I’ve almost felt like her Girl mom! We shop and gossip together. Now and then, we cry together; No one makes me cum harder than a sissy girl who knows what Mama needs.

At this point in the game, Jessy is no novice. She’s an experienced woman who isn’t afraid to tackle any sexual challenge! So when her new boy toy asked to breed her, my smart cookie called to tell me all about Jessica’s First Breeding!

Continue reading “Jessica’s First Breeding” →

slut

Anna 844-332-2639 EXT. 203

Tami was being especially naughty and bratty on Easter Sunday. Mommy told Tami, to behave and that she had a surprise for her. A special Easter egg hunt that would even make the sluttiest sissy blush. Mommy brought Tami to the nursery, carried her and dressed her in her special Easter outfit: a special dress that was different easter egg colors, and beautiful frilly trim.

Continue reading “Sunday, Tami Easter Sunday! Pt. 1” →

Roped Up Sissy

Posted 3 weeks ago by Alex

Alex 1-844-332-2639 Ext. 425

For a long time I had a sissy sub who was always so obedient. Did everything I asked, a real dream for me. And I have a very fond memory of one night I finally tried out one of my favorite playtime activities with him… or her shall I say. Shibari. If you haven’t done it, you have to live more! There is nothing more fun than getting a little… roped up. But she had never done it with me, and I wanted to see how she reacted to it. And I ended up being pleased, I must say. I’ll describe how I tied her up and made her my pet that evening.

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Sissy Shopping Spree

*LUCY* 844-332-2639 xxx- 221

I know you love wearing panties but when was the last time you really gave into your desires and had a sissy shopping spree? Because I definitely think you need to do it more often. I love all things lingerie so filling my closet with new, sexy things to wear is the best way to spend the day. So tell me, are you an experienced panty boy or are you one who’s looking for a new mistress?

I adore panties too and I would love to discuss your favorite styles, colors, fabrics, and all of those fun things. I wonder if we have some of the same favorite types. We could totally wear them together on calls. I have a very extensive lingerie closet so I’m sure we have a few of the same panty sets. I guess we’ll find out when you call me, and we get to know each other.

Continue reading “Come With Me For A Sissy Shopping Spree” →

Laylene and Anna

XXOO Laylene 1-844-332-2639 ext 419 – XXOO Anna 1-844-332-2639 ext 203

It was almost Easter and Tami insisted her mommies take her to see Peter Cock N’ Tail. Tami even marked on the calendar on the fridge. Every day Tami would cross off the date and open a little box to sneak a chocolate. Finally, that day was here. Mommy Lay and Mommy Anna dressed Tami in her very best. A frilly dress with pink trim, matching stockings, little Mary Janes, and diapies underneath.

Continue reading “Tami Meets Peter Cock N’ Tail Pt. 1” →

Zesty Zoey 1-844-332-2639 Ext 403

Gender-swapping Part 1 here

I leered at him the way he would at me and made a sexual joke.  Offering to fix that for him with my cock.  My body rolled my eyes at me and told me I was being crass.  I grined and told him I very well knew I was.  Then I asked how did it feel to be on that side of the crassness?

Continue reading “Gender-swapping Forced Feminization Role Play Part 2” →

deal

Anna 844-332-2639 EXT. 203

Mommy Anna went to her Sissy slut bob and told him that she needed to talk to him. She pat the mattress and signaled him to come sit beside her. When he sat down, she told Sissy Slut bob that she was the only on with a real job as the man of the house and she needed to win over a few of the male leadership team to close a big deal at work. Sissy Slut bob was very supportive and encouraged his mommy Anna saying that he knew she would do it and she’s been working so hard. But that’s not why I called you over, said Mommy Anna. You’re going to help me.

Continue reading “Sissy Slut Bob, Mommy’s Executive Slut” →

Vivian 844-332-2639 ext. 254

Diapering my sissy next door neighbor is not how I thought I would be spending my Monday morning yet here we are. I wonder if his wife knows how naughty he is. He is usually so quiet and reserved yet he sure is a closet perv.

All I wanted was a cup of sugar to make a cake. I went next door expecting the missus to open the door and instead the hunky husband welcomed me in instead. The wife was out of town and Bobby decided to play hooky from work.
He’s a big flirt and as we did the whole small talk thing he peppered me with compliments. I came over in a robe covering sexy pajamas but when the robe slipped open I didn’t bother to close it. He had quite the view of my cleavage and my nipples were rock hard.

I didn’t want to tempt him too much. I am a naughty neighbor but I don’t want him to report back to his wife that I was disrespectful. I got up to leave and “accidentally” tripped spilling sugar all over both of us. As he jumped up and started to wipe sugar off his pants I heard that all too familiar crinkly noise.

Instantly I get excited. It’s been too long since I’ve played and I am going to take advantage. I apologize profusely and attempt to help. There goes that sound again and this time he knows that I know. Continue reading “Diapering My Sissy Next Door Neighbor” →

Sissy Saves The Crops

Ronnie 1844-33-CANDY Ext 443

Now that daylight savings has begun, it’s time for me to plant my own little garden. Daddy allows me one chance every year to show him I’m responsible enough to take on more chores around the farm. And every year, I fail. See, he gives me this plot of land and expects me to harvest the crops I’ve tended over months since daylight saving, but nothing ever grows!

Nothing ever grows because of the little devils with wings! They pick the earth clean of my seeds before the little darlings can sprout roots! Not this year, though! I have a plan to stop them from holding me back!

Sissy saves the crops!

Continue reading “Sissy Saves The Crops” →

dresses

XXOO Laylene 1-844-332-2639 ext 419 – XXOO Anna 1-844-332-2639 ext 203

Tami’s mommies had bought a whole bunch of new dresses for her. It isn’t every day one gets to transform their little sissy slut into a full-fledged baby girl. Some of the dresses were white with green trim, others green with white trim. But the crème de la crème was a green shamrock dress they had found for her. When Mommy Lay and Mommy Anna got back home to the nursery, they were shocked to have found that Tami was not herself, but her bratty self…

Continue reading “Tami’s cumming out party Pt. 1” →