Category: social taboo phonesex

Diana 1-844-332-2639 Ext. 248

My third session with Dr. Jenson started off like any other. I laid myself bare, opening up about my deepest insecurities and anxieties. He listened intently, jotting down notes and offering words of comfort as any good therapist would. But then something shifted. His eyes lingered on my body just a bit too long as I spoke about my troubled past.

I felt vulnerable, my guard down in that moment. I know now that he sensed this, saw an opportunity to exploit my fragility. “Let me help you feel better,” he purred, setting aside his notepad to turn in his chair towards me. His hand slid up my bare thigh and I froze.

Continue reading “The Very Bad Therapist” →

Sissy Ballerina Maid

TS Alexus 844-332-2639 EXT 349

My little cross-dressing sissy complained that she had no time to dress up and feel girlie. I guess her wife really hates when she dresses up as a female and wants nothing to do with it. So, trying to give her a solution to her problem while solving one of my own, I told her to come over. She could tell her wife she was coming over to watch a game or something.

My little girl came over in her boy’s clothing and squealed like a slut as she dove into my closet. She twirled and danced and shimmied into this cute little ballerina outfit. Pink nylons under a pink leotard with a huge oversized tutu. I helped her lace up her little ballet flats and then did her makeup.

Continue reading “Sissy Ballerina Maid” →

Julie 1844-332-2639 Ext 453

“A man has needs Dr. Julie” Derek whispers, as if he feels guilty. He begins to open up to me, and he tells me that his wife grew up in a very strict, religious family. She feels like sex is sinful unless it’s for reproduction. They met when they were teenagers, married young, and went on to reproduce eleven times in fifteen years. He confides that the sex was always missionary, and purely intercourse. But at least he was getting something. It’s been ten years since she’s had any desire for sex. She sees no reason for it. To have sex for enjoyment alone wasn’t an option. He doesn’t even think she’s ever had an orgasm. But he feels guilty fantasizing about sex, and he even thought about going to a Happy Ending Massage Parlor once. Although he could never really do such a thing. He can’t even masturbate because she has made him feel so bad about his sexual desires. I assured him that his feelings, needs, and desires were all natural, and he had absolutely no reason to feel guilty. Orgasms are healthy and necessary for the body. They build the immune system and help prevent diseases.

Continue reading “A Man Has Needs” →

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.

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You Look Edible

Lea 1844-332-2639 Ext. 244

*Sucks my teeth.* Damn, boy, look at you. Skinny little white boy, lookin’ like a fucking snack. You look edible and Big Mama is hungry. I been thinking about dippin’ you in chocolate sauce all day and lickin’ every inch of that scrawny little figure. Yo ever heard of sploshing?

It’s a kinky little fetish where you slather someone in food or mud, chemicals, whatever. I’m not much into dirty stuff like mud but as a big girl, Mama can get down with making a feast outta you. I’ll have you laid up on my dining table like a smorgasbord.

Continue reading “You Look Edible” →

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” →

https://phonesexcandy.com/pics/mila/mila212.jpg

School Girl Mila 1-844-332-2639 Ext. 220

Now I am sure you all know my semester at school has just finished. And there was a class I was taking that was really kicking my ass. It wasn’t hard, but the Professor was always making insane assignments and quizzes, I couldn’t keep up with his demands for the class. He’s a total prick. Anyway, I took the final he did up for us and totally flunked it. And I was so mad about it, like who gives you the right to make your class like this when you know all of us are busy with other classes and projects? So I decided to make sure I passed in the end.

Continue reading “School Final Grade Fuck” →

A Side Of Cream

Trans Alexus 1844-332-2639 Ext 349

A hard and horny man called me up on his lunch break today. I asked what he was having, but I didn’t really care because all I wanted to do was serve him a side of cream. Shecock cum cream! He was all for it, even when I told him he was going to have to work real hard to milk out his extra delicious cum treat.

Boy, was he ready as ever! He gripped me and pulled me from my panties. I was hard as a rock when his mouth dropped over my cock. “Suck my balls. Work out that cummy goodness.” I grunted through my teeth when he nibbled along my sack before sucking me in deep. Oh yeah, he was gonna get that side of sauce, alright!

Continue reading “A Side Of Cream” →

My Little Assistant

Mama Felicity 1844-332-2693 Ext 270

I don’t know when life became so demanding, but lately, I have found myself needing an assistant more and more. Thankfully, this small science lab specializing in shrinking men emailed me and said one of my clients had successfully shrunk to three inches and was ready to go home with me.

I knew it was possible, but I didn’t think it would happen! What a blessing to be gifted my very own little assistant! Someone who could work silently at my desk while I take calls. No one would hear his little voice as I worked, and he could skip around my keyboard to juggle my appointments for me. Happily, I agreed and couldn’t wait for the team to bring him to the house.

Continue reading “My Little Assistant” →