Category Archives: sissy boys

Conceited Sissy Faggot Britney Phonesex

This is my conceited little sissy panty boi, Britney. When we first met he was wearing his pink panties and dancing around his room to Britney Spears. Watching himself in the mirror of course… at first… but he knows he’s a hot little slut. We go through sissy magazines and he compares himself to all the panty bois and is absolutely positive he is hotter than all of them!! Well… I really don’t disagree. He IS a hot little minx and hey, he’s got it, he can flaunt it!! AND he is EXTREMELY obedient. So I let him get away with his self-admiration… as I’m making him shoot cum like a broken fire hydrant inside those pretty little panties!

xxx

*Nicole*
866-513-0833
BadLittleBitchNicole
Click It Sissy!

My Phonesex Lesbian Sissy

She was breathtakingly beautiful. Soft luminous skin, her curves shown to perfection in the tight dress she was wearing that I couldn’t stop watching her. We talked for a bit as the sexual chemistry between us sizzled. I was as eager to be alone with her as she was with me.

From the moment she kissed me I was wet. The feel of her slim body our breasts pressed together and her fingers on my pussy was enchanting. She laid me back on her couch and began licking my pussy. Her tongue sending waves of pleasure pulsing through my body, she ravished my dripping folds until I was screaming in orgasm. I couldn’t wait to taste her in return. I took my turn pushing her back into the corner of the couch. I pushed up her skirt and saw a bulge of rock hard dick snaking out the top of her panties. I looked up at her and she said “surprise, I come with a little extra.” It was more than a little extra but I eagerly licked her ass in her panties, licking up over her balls to the mushroom head of her clit.

I was expecting a night of incredible lesbian sex but instead had a mind bending night of transsexual sex. Feeling her fucking me while I looked into her feminine face, her cock better than any strap on I have ever experienced. It was the best surprise I have ever received.

Sadie

1-866-239-2972

www.sissyphonefantasy.com/sadie.html

www.candygirlphonesex.com/sadie.html

Silly Phone Sex Sissy! Let’s Put Those Stockings On Right!

Oh my goodness my silly sissy! Watching you try to put your stockings on is unbearable!! Adorable too because you are so clueless! But here… let’s show you how to put those on right! Now, first you take the stocking and bunch it down like this, from the thigh down to the toe. See? So your foot can slip right in! BUT! These are delicate silk. You don’t just jam your pretty little foot in like you’re shoving on a work boot! No. Point your toes. Yes! Arch that foot. Mmhmmm. Now feel me slide the stocking over those toes, up your calf and shin, over your knee… all the way up… Mmmmm. Doesn’t that feel soooo good?

Now you do the other one! 😉

Your BFF <3,
–Sherry–
866-679-3275
phonesexmamas.com/sherry.html
VoteHere :)

Dress You Up Pretty Fuck You Hard Phonesex

nicole103

Hey sissy bitch! Ready to play? Don’t come to me with your wishy washy unsure bs. Get ready and BE ready. I’m gonna get you dressed up all pretty like the nasty little whore you are. Lacy bra and panties, silk stockings, matching fuck-me pumps. Haha! Don’t fret, pet. You’ll get the hang of walking in them. Put on your favorite wig and we’ll paint your face like a perfect slut. I know how you love that cocklover-red lipstick and the mess you leave all over your huge dildo. And while you’re gagging on that, I’m going to fasten my biggest strap on around my waist and fuck you senseless. Hard and deep. I want to hear you scream like the sissy bitch you are… xxx

*Nicole*
866-513-0833
BadLittleBitchNicole
ClickItSissy

Phone Sex Sissy Slut Contest

I love it when you call me, all dressed up in lingerie like a nasty cum whore so eager to please me. You will do anything your Mistress requests of you because you’re aching to be my #1 Sissy.

Well guess what, you’re in luck. For 1 week only I’m holding a contest to see who can be the dirtiest nastiest Sissy Cum Slut. This of course will require an on camera session for me to take screen shots of you.

These sessions will be entirely up to you to pre-plan what you will do to impress me. Next Thursday the most creative Sissy Slut will be posted on my blog and get a permanent post on my tumblr page.

If you want to be remembered in my Sissy Hall of Fame you’d better dress to impress. Make sure there are lot’s of big beefy dildo’s involved as I want to see that boy pussy stretched to it’s limits!

Mistress Francie

1-844-332-2639 Ext. 208

http://www.sissyphonefantasy.com/francie.html

http://www.sinfullysexyphonesex.com/francie.html

Phonesex Watching The Young Sissy

My neighbor asked if I could watch her little boy for her. She was having a bit of an emergency. I was happy to have the sweet little guy to spend time with and assured her it was no trouble at all. We played games which included hide and go seek. He was a very good hider. I looked for him and couldn’t find him when I heard a giggle come from the back of my closet. I opened the door and found the most adorable face smiling up at me as he rubbed his face against the silk of one of my gowns. When I reached in to pick him up I found that he had taken off his shirt and had slipped a gown over his head as well. The sheer chunky square straps and stretched mesh of the satin gown gaped open as he squirmed to be set down.

“My, but don’t you look pretty” I told him and he giggled and turned in a circle. He told me he liked the way it felt so I indulged him pulling more of my soft satin and silk lingerie out for him to try on. Then He got bold digging in my drawer and pulled out one of my dildos and asked me what it was. Stunned I had no answer but “It’s a toy”. Then he asked if he could play with it, if I would show him how. How was I to say no to that sweet little darling face?

Sadie

1-866-239-2972

www.sissyphonefantasy.com/sadie.html

www.sinfullysexyphonesex.com/sadie.html

Well Hello My Pretty Phone Sex Sissy :)

Well hello my pretty pretty sissy boy! Come closer so I can get a good look at you! Oh, look at what potential you have sweet sissy boy. All we need to do is find you the perfect outfit (complete with sexy lingerie, of course) and make that face up a bit. Get out of those clothes. All the way. Don’t be shy! We’re just a couple of girlfriends having a makeover day! There. Look at that eager little clitty. Hee hee! I love to see your excitement! Now turn around and bend over for me so I can see your little boy pussy. I just want to see exactly what we’re working with. 😉 Perfect! I’m going to get you all dressed up, made up and ready to go in no time! Call me, sweetie! Let’s get started right away! We’re going to have so much fun!!

Your new BFF <3,

–Sherry–
866-679-3275
HotWifePhoneSex.com
VoteHere :)

Phonesex Sissy Fantasies And Confessions

He called for our first session wearing pretty pink panties. Knowing he was hesitant, maybe a little shy and/or nervous I let him start slowly.  We discussed his personal and professional life. We had a quick rapport and found many things to talk about before we got around to confession time. And what he had to confess–how vivid and sincere he was–actually turned me on as well as interested and intrigued me. His first time sucking cock was at University, and although he was sort of “scammed” into doing it, he was hooked.  So he did it again and again. And again. I can’t go into detail about our session as all my sessions are confidential without express consent to share. But I wanted to share this much. I look forward to our next sessions and pushing him back to where we both know he wants to be.

Do you have something(s) to confess? Fantasies  you need that push to fulfill? If you’re in denial, repressing, or otherwise holding on too tightly, maybe Hypnotrance is what you need. And maybe you are completely ready to spill right now. Come to me. Let’s see if we click. xxx

*Nicole*
866-513-0833
The Bad Little Bitch Nicole
Click Here

Phone Sex Sissy Gang Bang In The Locker Room

I helped my pretty little sissy boy get all dressed up in silky stockings and panties, lace bra, sexy high heels, and a front zip leather skirt with a button up vest top. We glued his eyelashes on, dark blue eyeliner with a white frost to brighten his eyes, foundation, blush, and a matte red lipstick with just the perfect amount of gloss. Perfect. Such a pretty little sissy. I told her I had a surprise for her and I could feel her apprehension! Heehee! It just added to the excitement. We drove to the local gym where every Friday all the biggest hottest black men get together for basketball pick up games. Of course, we arrived right at the end–right when all those beautiful sweaty men were heading for the showers. As I led her in the same direction she pulled back on my hand. “What are we doing?!” she asked. “Well, we’re going where those gorgeous studs are going, of course!” I answered. I practically had to drag her. But once we got there and she saw all those humongous, incredible cocks, I had to put my hand against the bottom of her chin to close her mouth! The four cocks–I mean guys–closest to us noticed us standing there. Their eyes went back and forth between us as little smirks crossed all their faces…

[To be continued]

Sissy’s BFF <3,
–Sherry–
866-679-3275
HotWifePhoneSex.com
Vote Here :)

You Will Love The New You Phonesex

You just can’t resist the allure of a sexy woman like me. Look into my eyes, look at my body, you would do anything for a taste of me. You would do anything to ease the swelling of your cock, anything to have sex tonight. Well I promise you’ll get laid tonight. Your eyes follow the stroke of my tongue over my lips. You lose yourself in the perfection of my makeup, the perfect color of my lipstick, my dexterous swipe of tongue, your imagination runs wild.

We are going to have such fun together. But see I am the kind of woman your mother warned you about, I will toy with you, just because I can, and you will love me for it Sissy. Oops did I just call you sissy? Oh I bet that hurts…. but don’t worry I will take wonderful care of you. Remember honey, I am perfectly organized, and I have the perfect little black book of secrets on you. Now I promised that you would get laid tonight, but no one is going to fuck you in those black sneakers, so hand them over, NOW Sissy! Let’s go get you that perfect pair of fuck me pumps, shall we? Remember my black book, I own you Sissy…

Sadie

1-866-239-2972

www.sissyphonefantasy.com/sadie.html

www.candygirlphonesex.com/sadie.html