Category: sissy

Julie 1-844-332-2639 Ext 453

“Dr. Julie, I think my husband is a closet sissy. He’s always hiding in my closet and trying on my clothes. He can’t hold a job or get a job because he’s so obsessed with being a sissy. I’m so sick of him not working. So I have an idea. I’m going to turn his obsession into money. That way we will both be happy. Can you please help me? Will you take him shopping for some slutty lingerie? Then take pictures of him in it? So that I can post him for hire?” she practically begged.

It sounded like fun to me. But I had to make sure it was the best thing for him. After having a long session with him, I was confident that it was. He was beyond ecstatic to go lingerie shopping.

So we went and picked out several sexy things for him to try on. Then we headed to the dressing room. He got more and more turned on as he tried each slutty thing on. I could see him getting harder and harder. And my instinct is, see a hard cock, make it cum.

Continue reading “Closet Sissy” →

My Sexy Pixie

Avery 1-844-332-2639 ext. 228

One of my favourite bottom boys, that I call my sexy pixie, has been extra dirty lately. I’ve always said that it’s the sweetest guys who usually turn out to be a total bottom bitches, and it’s the truth.

That’s exactly how I feel about my sexy pixie. He tries to come across as straight, but he has a total baby face and soft feminine features. His girlfriend works with me and I met him at one of our events a while ago. He and I hit it right off right away. He’s smart, funny and seemed like a great catch for my coworker. But I couldn’t help but think that something was a bit off. I just had this weird feeling about him that I couldn’t seem to shake.

Continue reading “My Sexy Pixie Is The Best Bottom” →

Julie 1-844-332-2639 Ext 453

His transformation has been amazing! We met through friends and hit it off right away. And it didn’t take him long at all to feel comfortable enough to open up to me. He told me that he had been curious his entire life and drawn to panties and girly things. He fantasized about what it felt like to be a girl. And I was so excited to show him!

First, I took him shopping for panties. He was so freaking excited that he was dripping in his underwear. I informed him that it was the last time he would ever be dripping in boy’s underwear. From here on out, it’s only panties for my newfound sissy. He was overly excited by this and looking at all the different girly girl panties. They were so frilly and feminine. Pinks and pastels, hearts, lace, and bows. By now he had exploded in those underwear.

Then it was time for more. He yearned for cock. All he knew was that he loved the taste of his own cum. But he fantasized about tasting other’s cum. And he desperately wanted to feel a hard cock in his mouth and ass.

Continue reading “His Transformation” →

Tami

Amber 1-844-332-2639 ext 404

Mommy Anna and Mommy Amber were up to some mischief this morning! It’s not every day you get to celebrate a birthday, right? The mommies went shopping beforehand to make sure they had everything they needed to celebrate their special birthday girl, none other than the biggest Candy slut of all, Sissy Baby Tami! Tami, sweet little Tami, she’s always such a good sport when it comes to the mommies’ surprises. And even if she doesn’t LOVE the ideas at first, once her mommies stuff her holes and tell her she’s a good little sissy, she will do anything they say.

The first order of business this morning was changing Tami’s diaper, which is always a bit of a production. Mommy Anna and Mommy Amber are meticulous about keeping their little sissy clean and fresh and, as soon as they got Tami into her naughty nursery, they wasted no time getting down to business. They had a surprise in store for their little sissy whore, and they weren’t about to let her wriggle out of it! They held her down (gently, of course) and, instead of stuffing Tami full of birthday cake, they proceeded to stuff her full of suppositories!

Continue reading “It’s not every day you get to celebrate a birthday” →

pump

Anna 844-332-2639 EXT. 203

‘’I love birthday Pumps!’’ exclaimed Amber, as she grabbed the lube for all of Tami’s Mommy’s big, thick strap-ons. But then, Zoey said that we shouldn’t use lube, that Tami was a big girl now and she could handle alllllll of her Mommies’ cocks well on her own. All of the Mommies looked at one another raising an eyebrow or two and grinned simultaneously. They signaled Mommy Mercedes and Mommy Diana to spread and hold up Tami’s little legs. ‘’With pleasure!’’ said Mommy Diana and Mommy Mercedes.

Continue reading “Happy Birthday Sissy Baby Tami!!! Pt. 3” →

Summer Suckfest

Avery 1-844-332-2639 ext. 228

It’s finally beautiful outside which means one thing, we need to get you ready for a summer suckfest. Have you spent the winter sucking off hung men? Or at the very least practicing on dildos? Because you don’t want to go into this summer lacking skills, do you? I didn’t think so.

Having a little dick sucking refresher is good every now and then. Especially when we’re on the verge of unlimited cock during this year’s epic summer suckfest. Even the most experienced sluts can always get better. Just think about how many cocks you can show off your new skills to.

Continue reading “It’s A Sissy Summer Suckfest” →

Glory Hole Master

*LUCY* 844-332-2639 xxx- 221

We both know you love a good glory hole, but would you call yourself a glory hole master? Or do you need some help to reach that level? The truth is, you frequent the local glory hole even though you try to hide your cock sucking obsession. You don’t need to deny it with me.

Have you been thinking about going down to the local adult bookstore and sucking some cock? I honestly love that these glory holes masquerade as “bookstores”. It makes me laugh every time I see one of these bookstores with men walking out licking their lips. I’ll get you into one of those “bookstores” so we can start your training. You’ll be a glory hole master in no time.
Continue reading “Let Me Make You A Glory Hole Master” →

Julie 1844-332-2639 Ext 453

Being a Sissy Scout Troop Leader had always been a dream of mine. So when the opportunity arose, I wasted no time. The Boy Scout Troop Leader informed me that there had been a large number of “Boys” that weren’t cutting it lately. There was an urgent need for more Sissy Scout Troops ASAP. I was so excited!

They looked secretly excited to be at Sissy Scout Orientation. I explained that they were here because they didn’t “fit in”. They were different than the other boys in the Boy Scout Troop. And we were going to see if this is where they belong. So I told them to take off all of their “boy” clothes. Then I gave them their sissy scout uniforms. They consisted of a white button up top and white pleated skirt that with a pastel plaid print. It was pink, yellow, purple, and green pastels. The sash was pink. And the panties were pastels. They had the days of the week on them with little flowers, butterflies, and princesses. And they were so frilly and girly. They had lace trim with little bows. White cable knee socks and black patent leather mary janes finished the uniform.

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Feminization Voyage

Avery 1-844-332-2639 ext. 228

2025 is a year of change, and this includes starting your feminization voyage with me. You see, it’s one thing to slip on a pair of panties every now and then but it’s totally different to commit to the feminine life.

I know a sissy, named Lexi, who has been desperately seeking real womanhood for a while now. At the beginning of this year we started our feminization voyage together and it’s been a wild ride. So sit back, relax, and let me tell you all about the fun we’ve had so far.
Continue reading “Are You Ready For Your Feminization Voyage?” →

sissy

Amber 1-844-332-2639 ext 404

I take immense pride in molding my little sissy into the epitome of femininity and obedience. It’s a journey, a transformation that requires patience, discipline, and a firm hand. And while she’s come a long way, I’d be lying if I said it was always smooth sailing. My sissy, bless her heart, is still a bit rough around the edges.

One of the most persistent challenges is her voice. Despite countless hours spent encouraging her to embrace a more delicate, feminine tone, that old “boy voice” still creeps in from time to time. It’s jarring, a stark reminder of the person she once was, the person she’s striving so hard to leave behind. Each slip-up is met with a gentle, but firm, correction. “Remember, darling,” I remind her, “a pretty girl speaks with a pretty voice.” It’s not about stifling her, but about guiding her towards the woman she is meant to be.

Continue reading “my little sissy” →