Humiliation Phone Sex Archives

October 7, 2015

A Sissy Pegging woman can be seen standing in front of a man while she is pegging him while wearing the sex porn toy.

Published by Diaper Sissy at October 7, 2015

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Sissy Pegging Phone Sex

If you have any lube I suggest you use it now! I want you to bend over for me and spread em. It’s about time for some strap-on phone sex! Being a closet fag such as yourself, you don’t have many options as far as sissification training, so I’ve decided to take a step and be your guide. My strap on is going to open up that little ass of yours so that it’ll be taking all sizes of cock in no time! I’ll use my big black strap on you every night to pound that little hole of yours. You’re going to become my pegging bitch while I teach you how to take cock. And when I think you’ve earned it, i’ll start bringing in real cocks for you to please. With some pegging phone sex you will soon be the biggest cock whore around. All of those holes of yours will be filled. As they should be. So do you think you have what it takes to be my sissy student? Can you get through my training? Well there’s only one way to find out isn’t there. Candy 888 430-2010

September 11, 2015

The boy was dressed in a pink sissy adult dress, high-heeled slippers, and stocks.

Published by Diaper Sissy at September 11, 2015

Teacher Takes Control

It was a normal day for me; I was in my classroom and working on the last of my paperwork when one of my students knocked on the door. I waved him in and couldn’t help but laugh when he entered the room wearing a frilly pink dress. He slowly walked up to me and started fumbling through some excuse about how he had lost a bet but I knew better.. He was a sissy, and no doubt, he was sent here for the humiliation he would endure walking through the halls. I stood up and walked over to him, lifting up his head so I can see his face, then giggling when I notice the bright pink lipstick and red blush on his cheeks. I lifted up the back of his dressed and couldn’t help but smile when I saw a thick, pink diaper on him.. This was going to be fun. I took him by the hand and sat him down in one of the empty desks, then I handed him a pop quiz I had written up the day before. Let’s hope he passes, or life is going to get a lot harder for this little sissy bitch. Brittney 888-430-2010

September 6, 2015

A Hot Girl is in a nude pose and she appears to be hot and sexy.

Published by Diaper Sissy at September 6, 2015

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Mommy’s Dirty Panties

Well what do we have here? I was just about to finish putting your laundry away like the caring mother I am. But then I got to your underwear drawer and I was in for a surprise. I moved some of your briefs to the side to make more room when the back of my hand brushed up against something silky. I closed my fingers around the fabric and low and behold there are my pink panties I wore last night. I’m certain this isn’t a mistake because I put those panties in my dirty hamper last night before taking a shower. Why would you have mommy’s panties in your drawer? Dirty ones at that! Do you like to sniff your mothers dirty panties? Or maybe you even like to wear them. What a poor excuse for a teenage son you are. Well you’re going to be in for a shock next time you open up that drawer young man. If you like wearing panties so much then I shouldn’t have to keep wasting money on those expensive boxers of yours. Adult baby Mommy is going to get rid of them all and fill that drawer with all sorts of frilly silky and even lacey panties that you love so much. That’s what you get for stealing my panties.

August 24, 2015

Unclothed during the photo shoot, the blindfolded boy looks incredibly attractive and seductive.

Published by Diaper Sissy at August 24, 2015

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Don’t Tell Mommy

You have been such a good little sissy, that I’ve decided it’s time for a surprise. Your mommy and daddy are going to be gone for a while, so your wonderful ABDL babysitter went out and picked up a special outfit that I want you to wear tonight! After I strip you naked, I’m going to put a cute little diaper on you and help you into your new, tiny, lacy maid dress. I’ll help you slip into your new white stockings, slowly pulling them up on each leg, before I put you in your new black heels. After getting you dressed, I’ll let you pick out your favorite wig and make up; after all, you want to look your best for our company! When I finish with your makeup, I’ll take you by the hand and lead you downstairs for your big moment and you better make sure you behave! I’ve got a whole closet full of new toys to punish you with: paddles and whips, gags and riding crops, it’s going to be a fun night.. and your big surprise? I invited my boyfriend over, just for you! And looking at the bulge in his pants… I’d say he’s happy to see you. Have fun, you little slut, and remember… Don’t tell mommy! ~ Babysitter Brittney 888-430-2010

August 22, 2015

A Nude Ava Lady is posing for the photographs while sporting a stunning black attire.

Published by Diaper Sissy at August 22, 2015

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Cuckold Sissy Hubby

I bet you think your dick is great… well its NOT! It’s a tiny, little pee pee, and you are a pathetic little cuckold bitch! I’ve eaten fries BIGGER than your puny little pecker. And I KNOW you touch it a lot. There you are diddling your dick in the corner, how PATHETIC!!! But what I can’t understand is how you find the fucking thing! What do you use for a jock strap? A thimble and some thread? Oh wait… you have to be a jock to use a jock strap. You can’t even hold a cup! Your dick is soooo small; I can’t even use it as a toothpick!!! I have to go and find a REAL man to satisfy my appetite. You know, someone whose dick is bigger than a hummingbird? A real man who knows what to do with his cock. Someone who won’t be a waste of my time. Someone who WON’T dribble out his cum. Someone who can keep it HARD for more than 2 minutes. Someone I don’t have to PITY fuck or FAKE my orgasms for. You need lessons to even think about fucking ME! The only thing your good for is fluffing my lovers, and being a good little sissy fag!

August 5, 2015

A Sissy Girl is standing there wearing the pink robe and holding a purse.

Published by Diaper Sissy at August 5, 2015

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Calling All Needle Dick Sissy Boys

I’m Miss Ava and I have always had a special fondness for little needle dick sissy boys like you. I know just how badly you need a confidant, sexy cuckold mommy like me. I know just what a big man baby like you needs. I mean lets face it your little inch worm sized dick is not of any use to me, but I do enjoy tucking your little nub between your thighs to form the perfect camel toe pussy. I love stripping you of what little dignity you have and turning you in to my little diapered cuckold slave. I will dictate your daily chores and turn you in to my sissy maid and kitchen bitch. You will take care of all my domestic needs, and even fluff my lovers for me and get their dicks hard with your mouth so I don’t ruin my lipstick. With your little penis in chastity and a diaper you will be forced to sit and watch your mommy get fucked by a real man…..

July 30, 2015

Published by Diaper Sissy at July 30, 2015

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Mommy for Diaper Girl

I have so many wonderful sissy boys in my nursery and I just love getting to play with them. I think it would be fun to have some time playing with a sweet diaper girl. She can join us while we play dress up and with all the toys I have for us. I can buy new outfits for my adult babies, the pair of them will look so pretty in their dresses and adult baby diapers! I would hold them to my chest and have them each latch onto one of my big tits so that they can adult breastfeed until they are full. Snuggles together will never be so much fun as they would be with a diaper girl to join us. When my babies made a mess in their diaper, I’d take my time wiping them down and powdering them so that they were nice and soft and clean. I’d love to rock my baby girl to sleep while I hold her and kiss her softly and gently. Hope I find my diaper girl soon! XOXO, Barb 888 – 430 – 2010