Category: cross-dressing

Doggy Style

I have interviewed hundreds of sissy boys about their favorite sexual position when being penetrated. I am sure you will agree that the answer is no surprise. Their submissive nature, desire to be women and submit as a woman, and need to be taken by a man or woman leaves a sissy with minimal choice.

Doggy style is perfect. It lowers the gurl into a sub position, reduces any control to almost zero, and affords the individual experiencing the penetration the ability to be fully clothed and yet exposed. This idea of vulnerability is hugely exciting to the sissy boys, and their need to feel exposed and humiliated is a large part of their subby nature. Continue reading “Why Doggy Style?” →

shopping together

Zia 1-844-33CANDY ext 402

Hey, girlfriend. You are one of my favorite sissy girls and we are going to have a wonderful day of shopping together. I’m so excited to buy so many fun and slutty things for myself and for you. I have the best taste, you’ll see.

We are going to have so much fun together! It looks like you need everything so we’re going to get you everything from heels to lingerie to tops and skirts. I’m going to help you look like the perfect slutty sissy girl and then we can paint the town red.

Continue reading “Shopping Together” →

TS Alexus 844-332-2639 EXT 349

After all day preparations, we’re finally ready to head out to the swingers club. A Mistress and her toy. I love that I’ve dressed you as a mini-me. Same dress, same lingerie, same makeup, and hair! You look almost just like me. Except you keep your eyes down, and your tits are much smaller. It makes me tingle as we walk into the club.

There is a large bed in the middle of the dance floor. It took so long to get you ready that couples are already fucking on the massive bed under all the flashing lights. Music pulses through the speakers, and I move you in front of me. My hand is cupping your tits as I kiss your next and grind into your ass to the beat of the music.

Continue reading “Swingers Club Show Off” →

GIGI 844-332-2639 ext 299

My best sissy slut is my mom’s new husband! What can be better than some family fun? These dirty little secrets, hiding in the corners and manipulative lies and all just to protect your perfect on-site fucking. But even the best things could be improved. For example, when your mom brings her new husband in the house and he, who technically becomes your stepdad, is getting an eye on you. At the beginning I did not pay attention much: this is not the first time, when old fucker is having a crush on me. But it is definitely the first time, when he asks me to fuck his ass! Continue reading “My Best Sissy Slut is My Mom’s New Husband!” →

Cross-Dressing Sissy Boy

Lyla 1-844-332-2639 Ext 264

It surprised me to find out my big brother was a Cross-Dressing Sissy Boy.

It all started when I arrived home from school early. I caught Cory red-handed, or should I say red, dressed in our mom’s sexy lingerie. He was so embarrassed, but he became my cross-dressing sissy boy from that day on. I reassured him that this would be our little secret, for a price, of course. This began my fascination with cross-dressing, feminization, and sissification. I love dressing men like the perfect little girly boys. The days of playful dressing and teasing with Cody still go on to this day—time to slip into something sexy and explore your kinky cross-dressing fetish with me. Continue reading “Cross-Dressing Sissy Boy” →

TOM 1-844-332-2639, extension 342

Lots of guys will say oh no, stop, that is “exit only”. But you can’t say that can you? We both know what you are and that you love taking it up the hershey highway. That little dumper sees lots of action. In fact, me just talking about it makes you involuntarily push your faggot ass out in anticipation of my big dick. You are well versed in what rear entry is all about.

You should always be face down, ass up and assuming the position – the position to get fucked by yours truly. I will top you and force you to embrace your inner faggot. Filling your fag cave full of my man cream. Of course, you will be begging for more because we both know you are an insatiable anal whore.

Continue reading “That Ass Is Not Exit Only” →

GIGI 844-332-2639 ext 299

What can be better than a sissy slut that pleases five married men?! It is so delicious to see, how you trying your best at pleasing me night by night. You cock is always hard and ready and your lipstick is always on its place. I love to put you on your knees and push you down on my dildo. You take it so deep by now; almost no gag reflex, it makes me feel so proud for you. You also take it so well in your ass: I love to take you from behind, spread your legs and push your back down to arch it.

You love my cock so much, but I know your little dirty secret, my lovely sissy girl: you need a real cock in your slutty mouth. You want to suck it so hard and so long, to make sure poor guy will cum inside or all over your face. As much as you want to suck it, you must have it inside your ass, Think, pulsing and hot. Stretching you all inside and making you scream, while he pumps you with his cream. Continue reading “What Can Be Better Than a Sissy Slut that Pleases Five Married Men?!” →

GIGI 844-332-2639 ext 299

I love My Men Leashed. I hold your hand, while we walk, enjoying some free time and a nice weather outside. You go a bit behind me, following my directions and keeping your head down. People looking at us: the notice how beautiful I am and how average you are. They think what such a perfect sexy doll like doing with you. They think that you are shy and afraid even believe that I am here with you. But we both know that is not true: you are horny like hell and your cock is so hard, that it becomes hard to hide it. In the morning I put a white collar on your neck, lock it tight enough for you to feel it, but not too much that will make you chock on the way. I also zipped the short leather leach to your new accessory, thin enough to hide under your shirt, but pretty strong to hold you. Continue reading “I love My Men Leashed Phonesex” →

Avery  1-844-332-2639 ext. 228

Panties, panties, panties! That’s all a panty boy phone sex slut like you thinks about, isn’t it? I can’t say that I blame you though. There are so many cute and sexy styles that you can wear a new pair every single day and never repeat. Add all the different colors and you’re going to be serving up new looks all the time.

But I have a question for you, panty boy. Who is it that you’re prancing around in your panties for? Is it just you and your full-length mirror spending time all dressed up? Or do you have a special someone you wear those panties for?

Continue reading “My Sweet Panty Boy Discovers His Kinky Side” →

~~~Olivia ~~~ 844~332~2639~x~226~~~

Today is the day; I was thinking about how things were going for a caller today; wondering how his first steps into becoming the sissy he yearns to be are going.  For a few sessions now he has been expressing to me his desire to not only dress the part but to become his true self.  He told me about his love for the smooth silkiness of women’s panties, the way a bra formed his perfect female chest, and the signature scent we decided best.  Through hypnosis, I have let him experience how sexy it is to be true to himself. To be the sissy he is. I let him feel the soft silky panties as they move with him as he walks rather than just hang on him as his boxers did. Continue reading “Today Is The Day” →