Sissy Boy Phonesex Archives - Page 3 of 8

January 18, 2016

In this image, a lovely girl stands in the room, wearing a lizabeth print dress and looking cute.

Published by Diaper Sissy at January 18, 2016

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Sissy Baby Fun

I love spending time with my favorite little sissy baby. Do you want to spend the day with Mommy? Lets get you dressed first. I pull out a pretty pink babydoll dress and you raise your arms so I can put it on you. I pull out a blonde wig and place it on you and a pink headband to match. You tell me you want to look pretty like mommy so I place some pink blush on your cheeks. I put on your shoes and socks and we’re ready to hit the mall for some shopping. Everybody is staring at us but you don’t care. You show off and twirl in your pretty pink dress. We go to the women’s department to pick out some new panties for you to wear over your diapers. We find a silky lace pink thong and you beg me to get it for you. You’re my favorite abdl-baby, so of course I do. We leave the mall and you can’t wait to try on your new panties. Liz 888-938-7382

December 10, 2015

There were numerous Christmas presents on the ground for the people.

Published by Diaper Sissy at December 10, 2015

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Christmas Surprise

Mommy was so excited Christmas morning. She and you had spent a lot of time putting strings of bright lights and pretty ornaments on the tree, and now there were big boxes wrapped in paper sitting beneath it. Mommy pulled out one of the boxes, one covered in long curls of ribbons, and handed it to you. Her face was radiant as she waited for you to tear off the paper and see what she had for you inside. You tried so hard to smile when you looked at all the pastel pink fabric. You held it out in front of you, this dress made of satin and lace ruffles. Oh no, it’s a dress for sissies! Mommy clapped her hands, eagerly chanting for you to try it on. It was nice to see Mommy happy, and you wanted to please her. Pulling off your pajama top and bottoms, you slipped into the dress. Your face flushed with embarrassment. What would your friends think if they saw you now? They would tease you for crossdressing, at least! But Mommy couldn’t be more pleased to see you in the pretty outfit. Call Mommy Lauren at 888-938-7382

December 4, 2015

Published by Diaper Sissy at December 4, 2015

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You Big Sissy

You are a big sissy aren’t you? Always wanted to wear dresses, but never told anyone or ever tried one on until that first day in December. You saw me getting dressed for my Christmas party and I saw you peaking at me through the half opened door. I asked you if you liked my pretty, pretty, party dress and your eyes got real big and you nodded your head yes. You walked over to me and started feeling the pretty red satin material with your hands rubbing up and down my back. I could see the pleasing look you had in your eyes as you watched me slip my silky, black thigh high stockings on. You watched me put on the finishing touches to my jewelry and make up. I turned around sitting at my vanity and asked you if you would like to try on a pretty dress. You looked at me with amazement and said is a shy, little, tone “yes mommy I do”. I walked over to my closet and pulled out the dress with the most ruffles and lace on it and told you to get take off your shirt and sit on the bed. You held your arms up and I slipped that pretty dress over your head. I buttoned it up and asked you if you would like a nice pair of panties to wear with your dress and of course you said “yes mommy I do”. I made you take off your pants and you slipped on a nice pair of silky, pink, panties. Oh the look on your face as you admired yourself in the mirror…..you really like that don’t you honey? You nodded your head in agreement with me and then I said you are Mommy Candy’s big sissy aren’t you? Now, you big sissy give me a call so I can make YOU a big sissy! Candy 888*430*2010

November 28, 2015

A Pink Princess Dress The doll was dressed in a pink princess gown. It's standing close to the window.

Published by Diaper Sissy at November 28, 2015

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You’re Mommy’s Little Girl

Oh no! Mommy caught you trying on her pretty bra and panties set and now she’s decided that she’ll turn you in the baby girl that she’s always dreamed up. What started as a bit of curiosity is now going to become a lifestyle. Everyone is going to find out that you’re a big sissy! You only wanted to try on her sexy pink bra and panties once. That’s all! You liked looking at mommy as she got dressed because she looked so pretty with her big, milky white tits spilling over a tight bra and her ass revealed with a little thong. Mommy won’t hear anything you say though. She’s going to send you to the lingerie store to get a proper bra fitting. She’ll throw away all your pants so you have to wear the frilly dresses she buys you. You are going to get your hair done in ribbons! You’re innocent fetish has turned you into a proper sissy. Lucky you! Call Lauren at 888*938*7382

November 12, 2015

He is a handsome man wearing a black clothing and wearing makeup.

Published by Diaper Sissy at November 12, 2015

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Forced To Be Pretty

You’re in big trouble now! Mommy Lauren caught you in the bathroom, playing with a lipstick she had left on the counter. She had always thought you were a big sissy and now she knows for certain. She’s not going to let you off the hook so easily. Mommy Lauren tells you to sit down on the toilet and stay still, she’s going to make you so pretty. She takes the lipstick out of your hand and tells you to pucker your lips. She applies a thick layer of hot pink and then puts a shiny gloss on top. She orders you to close your eyes, and then you feel one of her soft brushes rubbing back and forth over your eyelid. Opening your eyes, you see her leaning over you, brushing a bright rouge onto your cheeks. She orders you to look in the mirror. Don’t you look just lovely! She tells you that she’s still upset with you so you need to leave the house and play with your friends. She pushes you out the door with a full face of makeup. Will the boys be surprised when they see your sissy face! Call Mommy Lauren at 888*938*7382

November 1, 2015

A Sweet and Seductive Lady The woman was just partially clothed. And she has the appearance of a candy doll.

Published by Diaper Sissy at November 1, 2015

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Sissy Whorehouse Halloween

Oh man did I have the best halloween ever. There’s never a bad time to add humiliation phone sex to your holidays! This year I got to dress up my little sissy sluts and boy did we have some fun. Instead of a little haunted house we decided to turn our garage into a little Halloween sissy whore house. Instead of passing out candy we passed out blowjobs! My little sissy sluts all stood in a line on their knees as one guy after the other started coming up and pulling their cocks out to get sucked by my sissies. There was this really hung guy in a Zorro mask who was so hot he kept looking at me while my little sissy cock whore made sure his knob was well polished, bobbing it all the way down her throat. So many guys of all shapes and sizes started lining up. There were black guys with their big cocks, a couple of white guys and one Asian guy. My sissies were really put to work tonight at our Halloween sissy whorehouse. And that’s why I love sissy whore phone sex. Ava 888 430-2010

October 29, 2015

The lady had a pair of sexy bosoms and was dressed in a western attire.

Published by Diaper Sissy at October 29, 2015

Strap On Training

I think it’s about time for some good ol fashioned pegging phone sex. You lubing up that ass for me you little pegging slut? Mmm I’m going to stand behind that little ass of yours and put on my nice thick strap on. It’s the big black one just like you like it. I’m going to rub my big mushroom head all over that little puckered hole of yours. Are you ready for my cock? This is your training you little slut. You need to learn how to take my cock if you ever want to be able to take a real cock up that ass. Just imagine a real man grabbing onto those hips of yours and stuffing his big thick rod inside that hot little hole. Are you ready for a real cock? I’m going to keep pounding that ass of yours until you can take it like a good bitch. Stick that ass out for me so I can slap it . Are you ready to cum? You better be rubbing that little pecker between those legs of yours. Be a good little bitch and have some strap on training phone sex. Candy 888 430-2010

October 27, 2015

A Sissy Barbie Girl the lady was dressed in an extremely deluxe version of a traditional white southern belle attire.

Published by Diaper Sissy at October 27, 2015

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Halloween for Sissies

It’s that time of the year! That enchanting smell that comes with fall weather, pumpkin spice lattes, and Halloween. What better opportunity is there for a sissy to go out on the town in the frilliest of gowns? Imagine how much fun you can have just preparing for the event. Going to the store and finding a Barbie pink dress with a full skirt so that you can wear a diaper underneath with no one the wiser. A trip to the makeup counter for a bright lipstick to match. After that, returning home and trying it all on in front of your mirror, looking at what a beautiful sissy you are. That’s so exciting! I love hearing about sissies dressing up in girly clothes and hiding a diaper underneath. Maybe with lacy underwear over it! Are you planning on going out in your sissy wears? Call Mommy Laura and tell me all about it. Lauren 888*430*2010

October 25, 2015

The lady was dressed in a white western costume dress with panty, and she was showing off her ample assets.

Published by Diaper Sissy at October 25, 2015

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Sissy, Sissy

Well what have we here? A big whinny sissy boy! Do you really think that I will let you get away with this naughtiness? Bad behavior does not get rewarded! You will come over here right this minute. Stop that whining now. Where ever did you get that dildo from? Don’t try and pretend that I didn’t see you in the corner with your hand in your diaper, and playing with that big dildo. I saw it and now you will pay for it. Come here! Where did you get this dildo from? Oh my! Not the babysitter when she stayed last weekend with you. Now let me check that diaper first. Of course as I suspected you made a big mess in your diaper from playing with that pecker. You came all in it and now you need to be cleaned up. But first things first, bend over my lap. Yes that is my leather paddle you see. I am going to use this leather paddle on your bare butt. Stop whining, sissy boy! I am going to show you where this dildo goes for you, sissy boy. Call Tawny (888) 430-2010