Archive for the 'Crossdressing Phone Sex' Category

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I caught you in my panty drawer

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Imagine my surprise when I caught you looking at my pretty panties. At first I thought you wanted to be close to me and see if my sweet scent was on them. I watched for awhile as you got out of your boxers and put on a pink lace thong. Giggles. You pranced in front to my full length mirror as you rubbed your ass and made kisses in the mirror to yourself. I got closer but you didn’t hear me as you were so caught up in looking at your sissy self.  Is that a wet spot I see from your man clitty?  Do you know what? If you want to be a little panty boy then you need a whole makeover.  I see you already found the lace bra for that pretty thong. I will get you a pair of pink stocking with the pretty lace band at top and find a pink cami.  Now all we need is some shiny pink lipstick and you are all set!

 

Is that the door? My boyfriend is here, but then you knew he was coming over. I wonder what he will think when he sees my daddy dressed like a little sissy boi?  It is okay daddy, I won’t tell mommy that you like to dress like a girl. Are you flirting with my boyfriend?  You are a naughty daddy and I think you need to be taught a lesson.  Don’t worry, you will love it before we are done with you.

 

xoxo Teen Princess Delaney

Daddy Was Dressed Like Me

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I came home from school early today and saw Daddy’s car was in the driveway.  I thought it might be fun to sneak up on him, and make us both giggle. I walked through the house and he was not in his office, den, living room or even his bedroom. What I walked in on I could not believe!  Daddy was wearing my silky blue panties and matching bra.  He was standing in front of the mirror running his hands up and down his body. Daddy, I yelled What are you doing?  His face turned bright red and I looked down to see a little bulge from my daddy in my panties.  I listened to daddy try and explain but I wasn’t having any of this. I decided if he was going to go all sissy boy on me, he needed to go all the way.  I took daddy to the bathroom and waxed his legs. LOL, did he scream like a little bitch.  I had him put on a pair of my knee high socks, a tank top and I found a pair of pink tennis shoes that were way to big for me.  “Look at yourself in the mirror now, daddy” I said.  I tossed a tube of my pink strawberry lip gloss at him and told him to use it on his cock sucking lips.  There now you look like a little sissy boy slut.  Now if daddy is going to look like a girl, you must act like a girl. I told him to get in the car and drive us to the nearest adult book store.  I told him to find an empty booth and I would be right there.  I explained the hilarious situation to the man behind the counter and told him to send as many men our way as he could.  Well, I don’t mind telling you that my daddy sucked a lot of cock that day.  I even made him take one up his ass.  When we were done, I made daddy lick the walls and floor of any jizz he missed with this mouth and tongue. My mind was going in all directions, I mean I want to go to Prague with my friends when I graduate and that will take a nice amount of money.  Well you can see where this is going, my daddy is now my whore!

Your Big Night Out

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You are in the mood for something hot and kinky tonight.  You know me; I am ALWAYS in the mood for hot and kinky.  We meet at my apartment, so we can get you ready for your special night on the town.  You know that I am the ULTIMATE party girl.  The party can’t really get rocking until Dani is there.

We go through my closet.  I find some sexy lingerie and an ultra-short and slutty little cocktail dress for you to wear. You need my help with those little girly details that complete your whore look.  I help you with your make up, hair, jewelry to complete your look.  Last thing we do is put a second coat of cocksucker red lipstick on your kissable lips.  You look so fucking hot. Wait until the guys see you tonight!  They won’t be able to keep their hands off you!  They are all going to want to fuck you tonight!

I take you to an Alternative Dance Club up on North Avenue.  It has a secret party room in the back.  Since you are with me and looking so utterly fuckable, you are allowed into the secret room with me. Once you get inside, you see why it is so exclusive, a perfect sexual playground for your big night out.

I send you to the bar to get us a couple of girly pink cocktails.  I see guys are already checking out your ass and one guy is staring at your mouth and rubbing his cock through his pants.  He wants your lips wrapped around his cock, but I have someone else in mind for you tonight.

I bring over a black guy who has a reputation of having the BIGGEST cock in Chicago.  I make the introductions and see him checking you out.  He is smiling.  He wants you.  I pull you aside for a second while he is taking off his shirt.  I tell you “Pleasure him and make me proud.” I like reminding you what you are. My little bitch slut! u are in the mood for something hot and kinky tonight.  You know me; I am ALWAYS in the mood for hot and kinky.  We meet at my apartment, so we can get you ready for your special night on the town.  You know that I am the ULTIMATE party girl.  The party can’t really get rocking until Dani is there.

We go through my closet.  I find some sexy lingerie and an ultra-short and slutty little cocktail dress for you to wear. You need my help with those little girly details that complete your whore look.  I help you with your make up, hair, jewelry to complete your look.  Last thing we do is put a second coat of cocksucker red lipstick on your kissable lips.  You look so fucking hot. Wait until the guys see you tonight!  They won’t be able to keep their hands off you!  They are all going to want to fuck you tonight!

I take you to an Alternative Dance Club up on North Avenue.  It has a secret party room in the back.  Since you are with me and looking so utterly fuckable, you are allowed into the secret room with me. Once you get inside, you see why it is so exclusive, a perfect sexual playground for your big night out.

I send you to the bar to get us a couple of girly pink cocktails.  I see guys are already checking out your ass and one guy is staring at your mouth and rubbing his cock through his pants.  He wants your lips wrapped around his cock, but I have someone else in mind for you tonight.

I bring over a black guy who has a reputation of having the BIGGEST cock in Chicago.  I make the introductions and see him checking you out.  He is smiling.  He wants you.  I pull you aside for a second while he is taking off his shirt.  I tell you “Pleasure him and make me proud.” I like reminding you what you are. My little bitch slut!

You unzip his pants and out pops the thickest and longest cock that you have seen.  You think of that tiny little dick in you panties and feel so inferior to this big black man.  You lick and suck his cock while I warm up your little ass to get you ready for his cock!

Dani

Trip To The Truck Stop

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Who gives a fuck about your feelings, your desires, or that teeny little cock of yours? Certainly not me. I don’t care who you want to fuck, how you want to fuck, or what you want to fuck in. Take your panty wearing, cock sucking submissive ass to the truck stop with a sign on your forehead that says, “Free Fucks Here.” All I’m going to do is laugh at your stupid ass anyway, so make sure the story is interesting when you call me afterwards. I’ve heard “he slapped my face with his cock then made me gag on it” too many fucking times. Surprise me with something a bit more original sissy whore.

Trying New Things

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I’m the type of girl who likes to try new things. I would say I am defiantly on the kinky side and love to experiment with everything. I had an idea that I wanted to try out on my Moms boss. I’ve been fucking him since December, when my mom dragged me to her Christmas party. I didn’t want to go but it ended up being a pretty good night. My moms boss and I have been fucking in unique places lately, we use different toys and I love to wear different costumes for him. He’s been married for 22 years and he defiantly needs a hot, sexy fuck toy like myself to keep his cock entertained.

I wanted to try something different and told him I wanted him to dress like a women. We went shopping to pick out the hottest lingerie, stockings and heels for him.  We even stopped at a beauty supply store that sold wigs and we picked out a long, brunette silky wig for him to wear. Every sales lady thought we were shopping for me and it made me wet knowing it was for my moms boss.

We went to a hotel and I had him go into the bathroom and try everything on. When he was done, he came out in a long white terry cloth robe with black high heels and black thigh highs. His wig looked amazing and he even surprised me and put on eyeshadow and lipstick.

I told him to come over to me and to lift my skirt up. There was a 9 inch strap-on waiting for him under my skirt. He looked surprised when I grabbed a hold of it and starting stroking my strap-on right on front of him. I asked him to slowly take of his robe for me and to get on his knees. I took a handful of his long brown hair and forced his head onto my long, thick strappy. His lipstick was getting all over my cock and it turned me on that he was very much enjoying being my whore for the night. I couldn’t believe how good he sucked cock and he took all 9 inches down his throat. It seemed like he’s done this before but he swears he never has.

I couldn’t wait to fuck him. I had him take down his panties so I could penetrate his tight fuck hole with all 9 inches of my cock. It was such a turn on fucking him from behind and pulling on his long, brown hair. When he was ready to cum, I told him to turn around and cum all over my strap-on. I had him get on his knees again so he could taste his sweet juices and cum all at the same time.

I love trying new things and I would love to try something like this with you or something completely different. I’m creative and I have zero limitations.

Girl Time

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You don’t have to hide it from me anymore. You can let it all out when we go shopping. We can share all of our dark secrets *winks* I take you shopping with me for a reason, ya know. I know you can’t help yourself but to stare at all the fabulous clothes when we walk around the mall. I love when I drop my bags in a crowd of people and make you get on your hands and knees and pick everything up. While we all watch how your pink panties are sticking out of your pants. I glance around at the crowd and give them a wicked smile. I want everyone to know that you are a full blown sissy boy. The next store that we’ll be going into you will be asking the woman to open up the ladies fitting room for you. This is just the start of our journey. With my impeccable taste with fashion and your sissy ass. You’ll be the woman that you’ve always dreamed of.

Just think about all the girl time we get to spend with each other.

Kiss Kiss,
Zoe

Sissy Boy Blowjob Lesson

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A sissy boy belongs with a cock in his mouth and that’s exactly what my sissy boy is doing right now. I sit down on the couch with my short little dress on. I slide up my little dress, and staring my sissy in the face is my strap-on. My sissy knew right away what he had to do. He leaned over, and took the fake cock into his hand. Then lowered his cock sucking girlie lips down on the tip of my fictitious dick. He can’t help but moan with pleasure. He loves the feeling of a big dick in his mouth. I put my hand on top of his head and push it down onto my strap-on. It makes me laugh when I see him choke on the silicone. He is having a hard time breathing I push him down so hard and long. I like seeing his eyes tear up..haha! I am teaching my sissy boy to suck a cock properly and so far he is taking his blowjob lesson well. The more cock my sissy boy sucks the better he will become at his duties. I think my sissy is ready for the real cock. I am going to bring him the fattest, longest, hardest cock I can find. He will take it like a good sissy if he knows whats good for him.

My Submissive Sissy

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Finding you standing in my bedroom all dressed up in my panties and my nightie, and some of my jewelry. I could even smell some of my expensive perfume on you. You’re dressed just like me. I watched you from the door way as you admired yourself in the mirror. Prancing around, practicing to walk like a woman. Your erection was a little hard to hide. I do have to say, I was a little surprised but I knew exactly what I was going to do with you from this point on. I walked into my bedroom wrapping my hands around your waist, whispering in  your ear “what a naughty boy you’ve been.” I’m thinking you need to be punished now. Making you crawl up onto my bed laying face down spreading your legs. Making you wait with anticipation as I pulled out my strap-on. Making you feel so helpless as I pushed up your silk nightie and ripped off your panties. Rubbing my strap-on along your tight aching hole. Watching you squirm all over my bed with pleasure as I started to have my way with you. Stretching that little fuck hole wide open. Teaching you a lesson not to go through my girlie stuff with out asking me first. I’ll be the one dressing you up and fucking you like my whore.

Charlie

You like the feeling!

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I know that it is hard to ignore the feeling you get when you put on pretty, silky, lacy outfits. The feeling of high grade silky pantyhose and real silk panties against your skin. The thought of it makes your little bitch cock get hard. Don’t worry my bitch, I understand and here to help you. I would love to degrade your sissy bitch ass. Take you out and make you put on some beautiful clothing. I think you should model the slutty outfits in the store, I’m pretty sure everyone will be laughing at you! Oh, then what is my plan for my sissy boy? Guess you will have to call and find out.

My Naughty, Slutty Panty Boys!

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Happy Halloween to all my naughty little panty boys!

I am in a very nasty mood and want to dress you up, super extra slutty and whorish tonight! It is time for some more sissy lessons!  Time to humiliate you!

Turn you out all dressed in sheer black lace lingerie, stockings, heels.  Turn you into that whore that you can only be for me!  Take you to a Party and let you service my friends and let that little bottom of your ass be used and abused. Pass you around like a toy!  Force you to suck big cocks and force you to  worship my pretty lady ass!  I give all the ladies a lipstick and watch them write a naughty word on your body!  I love to degrade you and humiliate you, my whore panty boy! Look at all the pretty ladies laughing at how much of a whore you are!

Halloween is the perfect opportunity to go the lingerie store for the first time. You can tell a little lie.  You can tell the sales lady that your little slut outfit is for your Halloween costume.    ha ha!  Only you and I know the truth, don’t we? We know you are a slutty little panty boy!

Skylar