Sissy Phone Sex Stories.

The voice on the other line sounds young. 20 or 21 years old at most. He’s certainly not one of my regulars and judging by the slight hint of nervousness in his voice it might be the first time he’s called a number like this. He probably just Googled cheap phone sex to try indulging in this kink. He knows who he's called. I smile and lean back in my chair, scraping my fingernail across my dark red corset I’d chosen to put on to get myself into character. It was fun working with a new client. A sense of mystery and challenge in slowly unlocking everyone of his desires. “Oh don’t worry” I purr softly into the receiver. “You’re not here to be judged. I’m not here to make you feel bad, why would I?” “I know. I didn’t think you would, I just didn’t know what to expect---” “Why don’t we start off easy?” I interject, establishing a position of authority. “I know, why don’t we give you a name.” “I don’t know if I should give-” “I don’t mean your name silly. I mean a name to use just between you and me. That makes you feel special right here and now, and gives you and I a connection. How does that sound?” There’s a moment of silence. But then, as I expected… “That sounds good.” “Wonderful. You can call me Miss S whilst we’re on the phone.” “That sounds good. Miss S”. “Well done, you’re very good at this. “Thank you Miss S”. I grin despite myself. I am good at this job. “Now what shall we call you? You sound like a Jenny to me, do you like that name”. “Yes Miss S, I think I like that name”. “Wonderful. Now Jenny, how about we begin properly with this?” “Yes okay.” I pause. “Yes okay, what?” “Sorry. Yes okay, Miss S.” “It’s okay Jenny. I’ll forgive you this time. But I don’t want you making silly mistakes like that again, do you understand me?” “Yes Miss S, I’ll be careful not to”. “Good girl. Now I like the people who call me to be descriptive. I want to hear exactly what you’re doing, what you’re doing it with, and how it feels. I don’t just want one word answers, I want to know what effect I’m having on you. Are you up for that?” “Yes Miss S, I promise I’ll be detailed.” “Good, that’s exactly what I like to hear. Now Jenny, be a good girl for me and tell me what you’re wearing.” “Yes Miss S. I’m not wearing anything special, just jeans and a shirt that I wore to work. But-” “But” I pounce, “I’m sensing there’s more to this ensemble little Jenny”. “There is Miss S. I’m wearing a pair of panties underneath my jeans. I couldn’t resist”. I grinned. Not so new to this after all. “You naughty little girl. I bet you were constantly hoping someone would notice, weren’t you? That one of the real men at work would feel you ass, and find out that you chose to wear panties. Like a little sissy bitch, is that right?” “Yes Miss S. It would have been so good if they had noticed.” “Pressed you up against a desk, pulled down your panties, and made use of that tight fuckhole, would you have liked that little girl?” “Oh yes Miss S, that would have been so good.” “I think you should strip to those panties right now Jenny. Lie on your back, legs in the air, that’s just the right position for you, isn’t it little slut?” “Yes Miss S, give me just a moment.” I hear the sound of the phone being put down, and I imagine him hurriedly shedding his clothes, not wanting to waste a second until he got back to me. He was back on the phone in a matter of seconds, a telling sign that I could go further. “I’m just wearing the panties Miss S. And my legs are up in the air, as high as they can go.” “I’m glad to hear it. You take direction very well Jenny”. “Thank you Miss S, I was told that would be good for me to do”. “You were told correctly. I just wish I was there to put you in more pretty things, not just those panties. I can picture you in a tight little evening dress that shows off your legs, or a nice garter belt and stockings that leaves everything on display. Would you like that? To wear such nice things that show off how desperate you are to be used?” “Fuck, I would Miss S. I’m planning on getting some more clothes for me to wear like”. “I’m glad to hear it. You’ll have to call more when you do, I’d love to hear how you feel when you wear those clothes. All sexy, desirable, wanting attention and recognition for how hot they make you look, and the effect that they have on you.” “Yes Miss S, I will do”. It was never hard to secure a regular client. TIme to ramp it up more. “Well done Jenny, that’s what I wanted to hear. Now why don’t you enjoy yourself in that position. Run your hands along your body, feel free to touch the parts that you like. But leave your dick alone for the time being, that’s for good girls only, wouldn’t you say?” “Yes Miss S, I’ll be a good girl.” “I like imagining you touching yourself like that. Your ass in the air whilst your hands touch your chest, legs and face. Do you want me to come to you now?” “Of course Miss S.” “I’d be wearing my big strap on of course. A nice 10inch cock for me to lube up with your mouth, and then turn you over and pull your panties aside and stretch out your little boy pussy. Would you like that?” “Oh god, oh god, yes Miss S, I really would.” I grin. It was never hard to reduce these girls to this state. “Wonderful Jenny. That’s exactly what I like to hear.”