sissy boys Archives - Page 2 of 4

March 24, 2019

solid black leather on one side & red padded garment leather on the other side

Published by Diaper Sissy at March 24, 2019

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Sissy Spanking Needed!

You have misbehaved and been a naughty diaper sissy, haven’t you? Running around, flirting with all the men, flipping your skirt up around them like a little cock tease! That is simply not acceptable, and you know that you are going to be punished for your behavior. Go ahead and kneel next to the bed, resting your arms across it to get in position for your well-deserved paddle spanking. You will count out loud every time I bring the paddle down on your bottom and at the end of your discipline you will thank me for giving you your punishment. Even if you have to talk through your broken sobs and your face is covered in tears and snot you will thank me and mean every word. The only thing in question here, is whether or not I let you keep the diaper on during your spanking. Why don’t you call me for some sissy phone sex and tell me how much you would love this treatment? Tawny 1-888-430-2010 #sissification #paddlespanking #diapersissy

January 27, 2019

he is an adult baby sissy diaper boy; please humiliate him.

Published by Diaper Sissy at January 27, 2019

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Forever A Silly Sissy Baby

You will always be a diapered sissy baby. Everything that you wear will be lacy, frilly, super feminine and girly and sissified! You did try for awhile, and I know you wanted it to work, but there never was a chance that you could do it. So don’t feel ashamed about this, dear, it’s just your nature. There’s no fighting who you are, so you need to embrace it! Though you should always be horribly embarrassed with how your tiny sissy clittie always stays hard inside your diapers. I do like watching you blush and it really is something to be embarrassed by! I might tell you put on a little show for me and my friends, have you rub the front of your diaper until you make cummies while we watch. I might even open up the diaper to show everyone the sticky mess that you made! Call me for sissy humiliation phonesex! Mimi 1-888-430-2010 Click Here to talk with a phone sex Mommy! #sissyhumiliation #diapersissybaby #sissyclittie

November 18, 2016

This image depicts a pink A Sissy Dress that is both adorable and coloured pink.

Published by Diaper Sissy at November 18, 2016

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My Cute Little Sissy

What would a good sissy boy like you do for his favorite abdl Mommy? Would you wear what I want you to wear, do what I tell you to do? What if I want you to put on the prettiest, frilliest dress in your closet so I can watch you walk around all day long being the cutest little thing ever? I’ll put a bow in your hair, some lacy white socks on your feet, and a pair of shiny Mary Jane patent leather shoes on you to complete the look. I know you would look absolutely adorable like that. Oh, I almost forgot your diaper! I can’t let a little abdl baby like you toddle around without his nappy on, can I? Let’s put on a nice, thick one today, so that you almost waddle with every step you take…and I’ll put you in a pretty pair of panties to go over that diaper of yours. You’ll look perfect! Call me for some abdl phone sex and I would love to talk to you all about it! Brenda 1-888-430-2010 Click HERE to chat with a phone sex Mommy #sissybaby #adultbabymommy #sissies

April 20, 2016

A Barbie Sex The lady was dressed in a barbie outfit complete with stockings and was walking around in pink high heel slippers.

Published by Diaper Sissy at April 20, 2016

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Small Penis Humiliation

I saw what you were doing the other day and I think it’s going to make for a great small penis humiliation and sissifacation phone sex story. You thought I was out at work didn’t you? Well I came home early and boy did I come home to a sight to see. I was about to walk into my bedroom when I heard something in there. I saw the door was cracked when I clearly remember shutting it when I left for work. I peeked my head in only to find you standing in front of the mirror, butt naked with your tiny dick tucked inbetween your legs while you held up a pair of panties to your waist. I stayed quiet to see what else you would do and sure enough after a few minutes you even put the panties on! How dare you ruin my panties with your little dick that can only shoot precum. Do you know how much those cost me? If you wanted panties so bad and wanted to be a little panty sissy you should of came to me instead of ruining my panties. Now you need to learn your lesson… #sissyphonesex #sissificationmommy #abdlfun Crissy 1-888-430-2010 Click HERE to chat with the phone sex mommies

April 20, 2016

A girl is sitting on the edge of the bed and wearing black lingerie underwear.

Published by Diaper Sissy at April 20, 2016

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Sissy Phone Sex

Are you a sissy boy phone sex lover? Don’t try and deny it now! I saw you wearing my stockings around the house when I wasn’t home. I noticed all of my lingere was a little stretched out and even had some hair on it. That hair certainly wasn’t from me, so it had to be you. Still denying it? Well that’s alright because I have proof. I set up a little nanny cam in my bedroom before heading off to work this morning and sure enough when I came home I checked it and you were on video going through my panty drawer! If that wasn’t bad enough I kept watching how you held up all my panties and bras to your body to see how you looked in them. And when that wasn’t enough you even went and put them on you! No wonder they’re all stretched out you’re a man putting on womens panties! You’re such a little slut for sissification phone sex aren’t you? #abdlmommy #sissyphonesex #sissytraining Ava 1-888-430-2010 Click HERE to chat with the phone sex mommies

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 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 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