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National Sissy Day Phonesex

I have a question… Do sissies love Halloween better than any other holiday? I mean really it’s the one day of the year (or month if you have tons of parties to go to *giggles) that you can dress to impress in your favorite girlie clothes and no one asks WTF.  You will get kudos for being creative and impressive as a girlie. I think we should petition that Halloween be a national Sissy Holiday. Don’t you? Wouldn’t it be cool if there was a national sissy day? I hereby deem Halloween National Sissy Day… Just between you and me my sissy dressing friends. So enjoy your holiday all my favorite little sissies and bring it on! Send me pictures of your efforts and make my blog next week.






Sissy Brandi Is A Phonesex Slut

Sissy Slut Brandi called me and need to confess what a slut she is, how she loves to frequent adult bookstores and theater gloryholes wearing her silky lingerie hiding under male disguise until she gets in the booth or the theater then she strips down to the cock sucking sissy she is. It was very enlightening hearing her many naughty confessions. She is well aware of what a slut she is and like a good whore keeps a stash of her sissy supplies hidden from her family. I am sure they would be very surprised to hear just what a dirty fuckhole she is.

Brandi, shall I tell them about how you came to be your pussy all plugged dressed in a black chemise and couldn’t wait to stuff your mouth with that big dildo? Yes the cock hungry cunt wanna be has 3 different sizes of toys that she made use of and she worked them all like a cheap corner hooker. As soon as one was done being used it went right back into her purring mouth as she moved up to the next size. You should have heard the slut moaning as her sissy cunt was fucked harder and harder it was a beautiful thing. Seems like her step daddy taught her well, and oh yes her half-brother too, they started her cock craving that still rages inside her slutty belly. It was a pleasure to use you Brandi you are a real dirty slut.






Sissy Son Treated like a Little Girl Phone Sex

I always wanted a little girl! Yet, I was stuck with a boy…..until one day I caught my boy in my panty drawer. That’s when it hit me, if he liked panties, why not go all out and teach him how to be the girl I always wanted.

He’s turned into such a sweet little sissy, always wanting to please and be mommy’s perfect little girl.

Mommy has been teaching Robbie so many different things, naughty things. Mommy makes him dress up like a little slut and uses him hard, showing him what little girls were born to do. I love making him my bad girl, doing nasty slutty things. Of course, once I get him all dressed up, we no longer call him a him. Right then, once he’s transformed, she becomes my sweet and spicy little Rhonda. I love whispering in her ear all the depraved things I’m going to do to her….It’s so much fun having a girl! Are you ready for me to whisper in your ear too?







Lets dress you up and Trick or Treat Sissygirl Phonesex

Trick or Treat… worship at my feet
If you don’t… have a care!
I’ll make you wear my underwear!

Halloween is the best of holidays for my sweet lil sissy sluts. The one day of the year you can dress up exactly as you want and wander the streets and while you might be snickered at, it would seem perfectly normal to everyone that you were in “costume”.

Lets play dress up sweetie. I will dress you up in everything from Marilyn Monroe, to Lady Gaga and make you feel like the sexiest or the most humiliated girlie girl in the world. Once I’m done dolling you up and making you into my little girlfriend, I’ll take you around to all my college parties. Show you to all those frat boys and sexy jocks and get that little clitty nice and wet. Before the nights over you’ll be begging me to let you take some college cock in that tight little girly hole.

Ready or not… Trick or Treat!




I will feed your addictions” Sissy Phonesex “Teen Tease Sophia

I know your secret addiction. You love girl clothes. Everything about silky, slinky, fitted, lacy and girl clothes has you turned on. It has created a new fetish or should we call it an addiction? You have a shopping addiction. You are melding the two fetishes begging me to push your envelope. Make you feed both addiction humiliation and shopping.

You’re itching to shop for sexy girl stuff. You get such a humiliation buzz form me forcing you to go shop and try things on. Your face turning flushed and your dickie getting hard in your pink panties you feel like you’re going to faint. Wouldn’t that make you look like a girlie puss?

*giggles* I love making you blush.







Silky Young Sissy Phonesex

It was quite a surprise to run into James at Victoria’s Secret. He is friends with my best friend’s son and we have met on many occasions. I stayed back to see what he was up to, first I thought maybe he was buying lingerie for a girlfriend, but I saw the way he caressed the silky chemise before he picked it up and casually held it to his body. I watched him a little longer as he moved to look at the panties. I made my way over to him and picked up a beautiful deep green pair of panties and handed them to him. These will go with your skin tone and coloring really well.  He was too shocked to defend himself he just blushed and took them and put them front of him.

I explained that it wasn’t that unusual for boys to like the feel of women’s panties and that if he wanted to come to my house I would help him figure it all out. He followed me home and we spent the rest of the afternoon with him trying on and modeling his new silky purchases for me. I let him fuck me with his cute panties on his silky chemise sliding against my body was so sensual. Next week I am going to show him my new purchase, my big black strap on cock.





Panty boys phone sex

I knew he stood out at when we had family parties at the pond.  He always knew just what to say and always dressed in the latest fashion.  I decided to find out just where he disappeared to.  I was looking for him and heard some moaning coming from the boat house.  There he was; on his knees sucking off one of the party members.   He is a cum slut!  I bet he’ll even love my strap-on.

Phone’s ringing; is it YOU?



Ms Libby Knows What NancyBoi’s Need Phone Sex

Do ya look at me wish you were as beautiful as I am. Sensual, sexual and so very feminine.  Luscious curves, perfect breasts and the most delicious pussy you could ever find. A body every woman wants, even sissybitches like you.  You look at me and know how wrong you are, how pathetically worthless you are in my shadow.  But, fear, not, there is hope for you yet. All ya need is the right Lady, the perfect Goddess, to take you and train you.  Dress you like the slut you are and show you what your holes are for. We’ll lock away that little clit because no one wants to see that disgusting little thing. Then me strapon will stretch you wide until you scream for me to stop, and beg me for more.

Be good for me, little sissy, and maybe I’ll even share you with some BBC that I know ya drool for.  Never let it be said I don’t know what a cocksucking little nancyboy needs.

British Mistress Libby




More Than Just a Phone Sex Sissy

Some sissies want more. They want to be more than just a sissy for the rest of their lives. Some want to be transformed completely. I am very familiar with the sissy that isn’t content with simply being a sissy girl, they want to be a real girl to be a real woman and are prepared to take the extreme steps to make that happen. I am here to guide you to that next level. Are you ready for me to guide you toward the world of womanhood? You must be completely sure, no doubts because once we start taking these steps into transformation there is no turning back.  The dress, the walk, the hormone replacement therapy and then finally *snip*snip*. Like I said there is no turning back but I am here to help…

Temptress Melissa




He Wants to Be A Hooker Phonesex

It was the cutest thing, Richard, my husband’s buddy came home with him after a day on the golf course and then caught me alone in the kitchen. I am used to being flirted with by his friends and Richard has been in that number before.  Not this time though, this time he asked if I would do him a favor, could I help dress him up as a hooker for Halloween?  Wouldn’t it be hilarious, no would expect him to dress up as a slutty woman.  A few months ago I probably would have innocently have helped him but now I recognize some signs I wouldn’t have before. His eyes a little too excited the smile a little too happy.

I told him I would need a practice run, he said he wanted me to go shopping with him to help him pick out the perfect slutty whore clothes. So we went to the local sex shop to see what we could get for him. We also found a short tight hooker red dress and some fishnets to rip up and of course the bra and panties and a cheap blonde wig to complete the illusion. He had to order some heels off the internet but we were able to practice his make-up with the full outfit on. The funniest thing though once he was all dressed he suddenly had to use the bathroom.  He has the look next time we work on the skills.