sissy phone sex roleplay with your kinky dominant roommate sexy Sadie

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Meet your new feminizing roommate Sadie

I’ve been looking for a roommate and it can be tough when you have men looking for a female roommate. Now believe me, I love men, I just don’t want to share a bathroom with one that I am not sleeping with. So I’ve been looking for a female roommate. Sometimes men will respond to my ad and I think about making them the offer of feminizing them and letting them live here. In reality I know I’d have no problem finding a man wanting to be feminized by his female roommate, but I like the fantasy. Can you imagine that you aren’t a sissy, and you’re looking for a place to stay. You find the perfect apartment, perfect location, lots of space, great rent price, quiet neighbors and just everything that you’re looking for. The only thing is that your roommate wants a female and a female only and tells you that by moving in you are agreeing to her feminizing you to make her feel more comfortable.

You think you’ll just do it until you find a better offer, you can tolerate her playing dress up with you a little for a place that nice. So you get there and she is unpacking your stuff and tossing your male underwear into a storage tote. “You can’t have these here, I’ll deduct the price of panties out of your rent this month” she says as she sorts out your clothes. She lets you keep a week’s worth of men’s clothes and the rest is going into storage. No problem she says as she explains that you’ll get dresses, skirts and things to wear around the house with her.

“ Why don’t we just get it all started now” she tells you as she pulls out a few pairs of panties. “I’m sure at least one of these will fit you just right.” How ahrd would your dick be as you modeled your new panties for her?

for feminization phone sex call and ask for Sadie
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sissy phone sex with taboo role play kitten Autumn for little dick men

 

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Want to be my sissy slut?

Taboo roleplays are my favorite and Ian had one for me when he called the other day for sissy phone sex. He wanted to be busted for having a little dick and made into a sissy slut, but the taboo part was who caught him. I was his sweet girl that had always looked up to Daddy. He was so strong and powerful and I had so much respect for my Daddy. Then one day I came home early and Daddy was jacking off his tiny sized penis in the living room. It was so small that at first I couldn’t even tell what he was doing, but the fact that his pants were down and his face was all red were a good indication that Daddy was whacking his dick. At first I ignored him and went on up to my room. A few minuets later though here comes Daddy to talk to me about what happened.

As he’s trying to explain why he was doing it I interrupted him and said well I have a question. If you’re so old why is it so small. He looked stunned but I went on and told him that he was smaller than any of the boys I’d seen and been with. I saw my hamper and said you know, it’s so tiny that I bet you could wear my panties couldn’t you? I grabbed a pair of rose colored lace panties and said here put these on. When I saw his baby boner getting pushed into the panties I had to giggle, this made Daddy’s itsy bulge grow a tad bit. At least I guess it grew because he told me so, but it was way too small to see any movement. I told him that he could wear pants to work and around his pals but when it was just he and I he would be dressing like a girl and more or less becoming my personal sissy slut.

Yours,
Autumn

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Sissy Phone Sex with bitchy entitled trophy wife and arm candy Harlow

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spend it all on your trophy wife to keep your secrets a secret

You’re a great big sissy fag, everyone’s going to know..unless…

Sissy! I have so much dirt on you. You didn’t think that anyone saw you blowing the pool boy did you? I did, and I filmed it. You probably didn’t think anyone saw the pictures you took on your last business trip. You know, when you spent your nights keeping a certain tranny’s cock warm. Does that ring a bell? I know that we talked about counseling but the truth is I am pretty much over it, all of it. It would be pretty devastating to you if everyone knew what a whore you are though, and you wouldn’t have me around to distract everyone from what a pussy you really are either. Your trophy wife wants an increase in her allowance. Actually, I think it would be a pretty fantastic idea if I had access to all of your financial accounts and you got an allowance from me.

I think that is going forward in our marriage that you will be asking me for money to buy your panties, to get your hair done, to upgrade your electronics and whatever else you need. In between sucking the help’s dick and trying on mini skirts and high heels you can learn to budget so that you can afford all of the things you need while I have everything I need and want. You’re a pathetic sissy husband and I’ll let you have your fun, but you are going to compensate me for having to deal with your miserable ass, do you understand? Nobody will ever know that you’re a cum connoisseur so long as you keep me satisfied in the only way that you’re able to. The secrets are safe with me for as long as you can afford it.

Harlow
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Sissy Phone Sex with beautiful supportive fetish friendly GFE babe Lola

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Want to be my sissy boy?

The girlfriends that you had in the past might not understand your love of panties and lingerie, but I do. I’m Lola, the sweet sexy woman that wants to give you the best of two worlds. Sissy play and the girlfriend experience. I suppose you could call it the girlfriend girlfriend experience since we would kind of be girlfriends and also boyfriend and girlfriend. We would make out and share lipstick, go shopping for lingerie for both of us and then spend evenings having smoking hot sex. Have you tried to open up to other women about how you want to wear panties around them and not just when you’re getting it on? Panties feel good, I like lounging around the house in my sexy panties. I don’t see why you shouldn’t join me in that by wearing your sexy panties around the house too. I’d like afternoons pressed against you as you hold me and feeling your cock stretching inside of your panties as you got so hard.

Do you know what else you can do with your sissy phone sex girlfriend? We can have girl’s nights in together. You get into something cute and sexy and I will too. We can talk on the phone and do our nails, talk about the adorable shoes we can’t wait to wear out, play truth or dare and then slide right into dating mode for some mutual masturbation sissy phone sex style. Yeah, I want to hear you jacking off into the soft slinky panties that you wore for me. I’m unlike any girlfriend that you’ve had and that’s because I let you be the you that you want to be. You can express yourself however you like and never worry about being judged for the articles of clothing that you like to feel against your skin.

Lola
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Sissy phone sex with the adorable and cruel small penis humiliatrix Cici

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sissy phone sex with SPH Princess Cici

Well it’s no wonder that you love being in panties so much. You look like maybe you should have been called a girl from day one. That little bitty penis is hardly enough to call a cock and it’s actually more like a clit. In truth my clit is probably bigger and puffier than your pretend penis. Since you have been living like a boy and sneaking around to get into panties I think it’s time I put your troubles to rest and just started treating you like a girl. God, I can’t believe that my boyfriend used to get jealous of you spending time over here with me. I told him you were no threat, but once I send him these pics that I’m snapping of you in your tiny cotton panties with camel toe he’ll see what I mean. Well he might see it, he may have to zoom on in to see your clit.

Since you weren’t born with a cock sissy boy, have you ever seen one? Have you ever held one? No, perhaps I can arrange that for you. Maybe not, maybe I will just make you sit there in your panties while I fuck real boys and real men and you squirm around seeing what it’s like when a hot girl like me gets fucked by a big cock. If you keep squirming I will find you a “post” to sit on if you know what I mean. When I get finished fucking I might make you inspect my pussy and clean me up. I bet you’ve never shot such a load in all of your life, but you will swallow the hole bit of it down your throat while I watch it all. This is what I do with little dick losers that can’t make me cum. I expose you in front of real men and turn you into my total bitch.

Cici
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Sissy phone sex forced bisexual play with your dominant big sister May

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sissy phone sex vixen May

I never had a little brother to control and mess with growing up but I think about how it would have been if I had. I keep thinking about this roleplay idea I have of being made to take my younger brother out on a date with me because I had gotten into trouble coming in late from dates in the past. So I’m really not pleased to have my little brother tagging along. I promised our Mom and Dad that I would not be fooling around with my boyfriend and that yes, it would be too humiliating to do so in front of my little brother. You are kind of my birth control for the night. My date is not very thrilled to see you with me when we meet at the theater either. I explain to him that this was the only way I could get out of the house with him and he’s like well we can ditch the little brat, right?

I hand you some money to get lost with and you protest that no, Mommy told you to watch me and you’re going to. Your big sister does not like hearing you tell her no, and for that you’re going to pay. You try to listen as I whisper into my boyfriend’s ear but then all you hear is him moan and agree with me by saying Oh yes baby. I pull my panties off out from under my skirt and push them into your pocket. I order you to go to the bathroom and change ito them and meet us at the car. You start to protest and I remind you about how much stronger I am than you and you hop up.

When you get to the car we’re sitting in the backseat of his car and I tell you to climb back in there with us. I explain that I promised Mom and Dad that I wouldn’t fool around with him in front of you, and I tried to get you to take off. Since you wanted to stick around I thought about it I didn’t say you wouldn’t fool around with him. You reach for the door handle and I remind you that I will kick your ass and tell everyone what kind of porn you keep on your computer, so with that you realize your choices are limited. I mean, you have been looking at shemale and femdom sites, you might as well do as you’re told so that everyone doesn’t know what a cock curious boy you are.

May
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Sissy phone sex with the very hot and amazing fetish temptress Roxi

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beautiful temptress Roxi

Hey sissy boys. My name is Roxi. I like to think of panties as the gateway drug of clothing. Most every sissy I know started with just panties. It makes sense though, does it not? Depending on where you lived and who you lived with when you first started feeling the urge for feminization panties might have been easy to come by. Were you a sneaky panty snatching pervert when you first started wearing panties? You wouldn’t have been able to snag my panties away from me without being caught. I might let you believe that you were successful in getting those panties of mine while going undetected, but I would just be waiting for the right moment to pounce on you for a confrontation. You might be sitting alone settling in for panty sniffing and a jerk off session or wearing them over your hard cock while you look in the mirror, but I will confront you.

Like a cat after the mouse I’ll spring on you and sit on your chest while you look up at me confused but so aroused. I’ll tease you with the information I have and hold a newly scented pair of panties to your nose while you’re helpless underneath me. As you breathe in that smell you’ll be more and more likely to confess and submit to being my sissy boy. You’re such a dirty panty sniffing perv that you’ll do almost anything to get a regular dose of my sweet smelling panties. It starts with panties, but I will not leave it there. I’ll have you in heels, dresses, makeup and I’ll be pegging you with my sexy strap on cock too. You’ll be so addicted to the smell of my panties that I’ll just pull the strings and make you move for me. It will be wonderful, for me anyway.

Roxi
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Sissy phone sex confessions with gorgeous bratty teen domme Stefanie

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Call Stefanie and tell her your sissy phone sex confessions

Just when I think I know everything that there is to know about sissy phone sex boys one of you goes and surprises me. That’s good though, I don’t ever want to stop learning about sissies and kinky boys. Whenever you all tell me new things about humiliation and roleplay it gives me even more ideas to do to sissy boys and panty lovers. Being a bratty domme that has a lot of sissy phone sex gives me a chance to be creative and it’s so much fun. Confessions are super fun too. If you need to tell someone about your new pair of high heels or your newest shade of lip gloss you can tell me. We can even trade makeup secrets or have an over the phone sissy makeover date. You can get out your hello kitty stationary and take down the shopping list I give you and call me back for a sissy makeover.

The other kind of sissy confessions that I get during sissy phone sex are about when you are totally slutty, or sometimes even downright whorish in the things that you do. Do you need a young Domme to confess to about how you blew that man you met on the dating site? Do you want to ask for cock sucking advice and training because you want to see him again? You can tell me or ask me absolutely anything at all. I like hearing slutty sissy confessions. And helping to make sure that you have plenty more to tell in the future. When you feel that stirring in your panties because you can’t shake what a slut you are call me up and tell me about it. Don’t leave out a single detail either, sissy.

I might be young but I’ve talked to lots of sissies and I hope to talk to so many more.

Stefanie
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hot humiliating Sissy phone sex with your slutty cheating wife Sandy

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hot cheating wife Sandy

I didn’t have any intentions of cheating on you, but I also didn’t know what a complete sissy you were. Looking back I guess I should have noticed it, and maybe I did and maybe I was in denial. Now you’re here with me in your snug white lace panties, lace bra, white stockings, high heels, soft girly makeup and wearing a big butt plug while you wait in the other room. I’m being bent over and fucked well by my boyfriend, it turns us both on you know you’re just waiting like a sissy cuckold cleanup bitch in the next room. Sometimes I have you watch while he fucks me. I’ll sit you down at the side of the bed and laugh at your itty sissy clit that you rub away at while I get fucked. This time is different though, I don’t want you to see me getting fucked before we renew our wedding vows.

My boyfriend and I were talking about I decided that our original marriage vows just didn’t fit what we have now. Our relationship isn’t about that anymore so I rewrote our vows and we’re going to renew them on our anniversary. This time it will end with I now pronounce you sissy cuck and slut wife and you’ll kiss my cum filled pussy as you kneel in front of me. I can’t wait to see the look on your face when you lift my gown and go for my pussy to kiss it and find it is overly stuffed with cum so much so that it’s oozing through my bridal panties. As you try to figure out how many men contributed to the wedding creampie I will be getting even wetter. In addition to our wedding bands I’ll be placing your new cock cage on you and you’ll put the key around my neck too. I can’t wait to see your bitch ass crying later that night when you realize how bad it is going to be for you.

 

Sandy

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Sissy phone sex for naughty panty boys with ABDL dommy Mommy Carla

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Mommy’s sissy can’t stay out of her dirty panties.

Mommy has spanked you over her lap, put you in your crib in bondage and I’ve even made you wear thick diapers around my friends. I don’t guess I got through to you, or maybe you just can’t help yourself. Is that it naughty boy? Mommy’s dirty panties are so enticing that you can’t stop yourself from snagging them from her hamper and hiding them in your room? Well sissy boy, you’re going to get a little of all of the above with some extra humiliation added to it. First Mommy Carla is going to strip you down completely and put you over her lap for a good spanking with my hair brush. I’m going to get your vibrating butt plug and then put you in thick diapers with locking plastic panties on top. Your playpen is coming out to the living room and I’ll be tying you in it so that you’re just there in display for when my friends get here.

Above your playpen Mommy is going to hang her dirty panties just out of sissy baby’s reach, so you can smell them and almost taste them, but can not get to them no matter how you wiggle. I have a feeling my friends will join in and hang theirs up on the line too, in face why don’t I see if they have some dirty ones to torment you with. You can sit there in the playpen and hump your thick diapers while the plug tingles you from the inside out. You better not interrupt the grown ups either. I only want baby noises out of your mouth, naughty boy. You remember what embarrassing evening you had the last time Mommy Carla’s friends were over don’t you? You can blush and cry, but you can’t get out of this.

Mommy Carla
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