Tag: sissy

Valerie 844-332-2639 Ext 243

My favorite friend to play dress up with called again today! We’ve been having so much fun trying on different girlie outfits and exploring how they make my friend feel. Remember, he’s little, and I’m his babysitter. I love how much he trusts me to guide him through our fun.

Today I thought it would be exhilarating to let him dress up as a pretty sissy Ballerina! His whole face lit up when I held up the pink tutu. “Have you ever worn tights like this?” I asked, and his little head shook excitedly. I had him remove all his clothing and boy undies, then rolled the toe of the pink pantyhose up his legs. The waist rested at his belly button, and I noted how cute his little bits looked all wrapped in soft pink.

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Babysitter Secrets

Valerie 844-332-2639 Ext 243

Over on phonesexcandy, I shared with you how I became someone’s diaper chastity keyholder, but here, I wanted to not tell you about the babysitting secrets I learned on my first day! In an age regression session, a boy a little younger than me was interested in playing dress-up. However, he didn’t want to explore his mom’s or sister’s closet; he wanted to see what I brought in my bag of fun.

I showed him some soft nylon pantyhose and a bra and panty set I’d brought just for him. As I started to help him put everything on, I realized how uncomfortable the stockings would be if he didn’t shave his leg! We agreed it would be best If I taught him how to shave his legs so he could fully enjoy the secret we were sharing. It wasn’t long after he was silky smooth and dressed that he confessed another secret I probably shouldn’t tell you.

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Taste How Delicious Life as a Sissy Will Be

Shemale Alexus 1844-332-2639 Ext 349

Would you like to know a secret about women? We like women better than men. That’s so nearly a universal truth. Sure, plenty of women are attracted to men or only have sex with men. But deep down, most of them like women better as people. Women support each other and lift each other up. They develop real, meaningful friendships so much faster than men do. Trust me. I’ve lived on both sides. Everything about being a woman is better, except for the way men treat us.

So, I’ve made it my personal mission. My self-assigned duty. My life’s journey is to find every questioning boy I can and show them the joys of being a woman. I’ve seen your side, and I’m living this side. I can walk you through all of it. Now, maybe you aren’t a woman inside. Perhaps you are just a sissy, but there’s nothing wrong with that. Let me show you how fun dressing up as a sissy can be!

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Mommy Daugther Date

Felicity 1844-332-2639 Ext 270

Hello again, my little ones. So many little boys come in here needing a mommy, but mommy has needs, too. In fact, it’s basically all little boys that come in here. I need more little girls, and since they just aren’t visiting, I’m just going to have to make a few. You see, Mommy really needs some Mommy/Daughter time.

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She bounced up and down in her heels excitedly.  My sissy worked hard and earned herself a special trip.  I promised her that if she was diligent in her lessons that we’d go to the panty store as a treat.  She’d kept her nose to the sissy grind stone and earned that trip in record time.  I called the store and made special arrangements for our trip that day.  We’d have the store all to ourselves with only the store attendants there.  We arrived and were ushered in, the door locked behind by us by the manager just as I’d asked.

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TS Alexus 844-332-2639 EXT 349

I love being invited to the lake on a hot weekend. Floating around under the sun, sporting my tiniest bikini for everyone to gawk at, makes me feel so sexy and, oftentimes, slutty. Plenty of boys have always overindulged all day in cheap booze mixed with a little heat stroke, and that opens up plenty of play time for a sexy girl like me.

However, your friends were teasing you pretty badly about how your shorts seemed in a constant tent today. I guess the little bikini holding my cock in was too exciting for you to keep your composure. You joked it wasn’t a hard-on,  just that you were so big, and since the fabric was wet, it clung to your massive man meat. I knew better but kept my thoughts to myself. The longer they teased you, the more I got sick of hearing it. I decided to show them and humiliate you at the same time. Playfully, I bet you I could chug a drink faster. Stupidly, you fell into my trap and lost yet another bet.

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Using a Fucktoy

Ashley 1-844-33CANDY ext 273

Using a fucktoy can be taken all number of different ways. Me and Zoey are taking it to a whole different level and using YOU as our fucktoy and you aren’t allowed to stop or complain until we’re satisfied. And you better not cum without permission.

You signed up for this when you called us, and you better make it a good show. You don’t want to disappoint us, do you? Such a good little fucktoy. Now, show us those toys that you’ve got there and let us pick which one you should use first.

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Sissy Humiliation

Ashley 1-844-33CANDY ext 273

Sissy humiliation is one of the best times of the day – once per day, every day is the best way. Sissy boys need it, and I’m happy to oblige. Today, I decided to bring out my 10 inch strap on and show my little sissy slut who was boss.

Walking into the room, I was happy to see my sissy boy on his knees, ready for me. He was practically begging to suck on this big cock but not before I walked up and slapped him in the face with it. Grabbing the back of his head, I shoved it into his mouth, slowly working my way to the back of his throat and hearing him moan the deeper I went.

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•CANDICE 1-844-332-2639, extension 233•

I have a little boy here who loves to be humiliated. He is so sweet to me, like my own special toy. Sadly his little dick isn’t anything to write home about. Poor guy is so pathetic in the pants that no one can even do anything with it. That’s okay though because even if he knows he’s small, he knows that he can still please me in other ways. Mistress like’s to be spoiled and there are many ways that he has been able to spoil me. You know who you are little one. My useless little pussy slave.

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Put it in Deep

Phonesex with Felicity 1844-332-2639 x 270

The problem with Mama playing with so many sissies and babies is that when I wanna get dicked down deep, there often isn’t anyone around to fill me up. Sure, I could go find some local big dick or some tasty BBC, but I wanna make love with my toys.

There’s something special about stripping a man of everything that makes him masculine and putting him in feminine lingerie, and then asking him to fuck me. The power shift is so heady it makes me horny. No one can blame me for wanting to make the connection that much better. However, it’s a rare sissy who carries a worthy clit, so I’ve made it a habit of putting my girls in hollow strapons.

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