Category Archives: sissy boys

You Look Like You Would Enjoy This Phone Sex

Be my sexy sissy boy

1-844-332-2639 ext. 222

I had chosen him from an online dating service because I thought that he had that certain something I was looking for. After our first date I was even more sure that he would want to play the game I was interested in playing. We were sitting on the patio having a few drinks when I sat my glass down and told him I had bought him a present and I hoped that he would like it. He said I didn’t have to do it. I told him I wasn’t entirely sure he would like it.

One more drink and I sent him to my bedroom to find the gift wrapped box with the big pink bow on it. On the Tag it said “I hope they are your size”. Inside was a beautiful classic black lace bra and panties wrapped in delicately scented tissue paper. I had put a little note in there that said  “If I’m wrong and you don’t like these just come back to the patio for another drink and we will forget that this ever happened. But if I am right and you do like them, go down the hall to the bathroom more is waiting for you there. Xoxo SadieContinue reading You Look Like You Would Enjoy This Phone Sex

His Wife Turned Him Into Her Sissy Bitch Phone Sex

He can’t let go of his life as Little Sissy Bitch Cuckold. She has long since moved on having married a real man with a nice big cock.

He used to be made to get dressed up in her clothes and make-up and watch as she was pleasured by that big beautiful cock…..

Continue reading His Wife Turned Him Into Her Sissy Bitch Phone Sex

My Stoner Sissy Is A BBC Cock Sucking Cuckold Slut

After he has smoked a nice blunt he likes to watch my hot pussy get filled up and stretched out, knowing he could never satisfy me like the real men I play with. I let him lick the cum mixed in with my pussy juices off that Hot Hung BBC‘s cock after I have been fucked really good and hard. I always make him beg for it, lol.

Continue reading My Stoner Sissy Is A BBC Cock Sucking Cuckold Slut

Sissy Whore Christmas Card Photo Shoot Phone Sex


You thinking of making a special Christmas Card to send out to all your family and friends? No?

Well too bad you cock sucking little bitch, we are going to make one anyway!!….

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My Sissy Boy’s Special Snowflake Dance Phone Sex

Sissy snowflake dance

1-844-332-2639 ext 222

The Snowball dance was coming up at my son’s high school. My sweet boy. It tore me up inside to watch him try and act like all the other boys. But I knew and have always known my little prince was not like the other boys. He is so soft and delicate. I just couldn’t resist this opportunity to give him a chance to become who I knew he was truly meant to be.

I spent all day shopping finding just the right things. When he arrived home, I was waiting for him in his bedroom. On the bed lay the prettiest icy blue shimmering party dress. Beside it were white stockings and little blue slippers and on top of the dress was a little pink and black striped bag. I could see his confusion on his lovely little face when he looked at the clothes I had laid out for him. Continue reading My Sissy Boy’s Special Snowflake Dance Phone Sex

Let Me Humiliate Your Sissy Ass Phone Sex


Elaine 844-332-2639 ext 250

I get great pleasure when I treat my sissy boys to a Humiliation Sissy  Phone Sex call. There you are dressed in your cute little panties. You really are a Sissy loser and you know it. You have a tiny little clit dick and you know it isn’t good for much. You may think you are sweet and cute but you aren’t, you are a good for only one thing…….

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Phonesex Prepping For The Pretty Boy Pageant

Aunt Sadie's Sissy Nephew

1-844-332-2639 ext. 222

Halloween was weeks away but it was time to start his training. On Halloween night my friends and I had decided we were going to hold our own Pretty Boy Pageant. We were each to find our contestant and dress and train them to perform by Halloween. I had chosen my sweet young nephew. His lithe body and beautiful eyes were a great foundation to build from. I began by inviting him to lunch.

At lunch I told him that I needed his help. Being my sweet nephew who adores his Aunt he said he would do anything to help me. I took him to my bedroom and laid out a pair of panties, a corset, garter belt and stockings to dress him in. He asked me if it was necessary with a pretty little blush on his face. I told him that this was just the beginning. I knew I had chosen well when he finally stripped away his boxers and I saw his little cock. It was made to be in a pair of panties. Continue reading Phonesex Prepping For The Pretty Boy Pageant

Mommy’s Special Boy Phonesex

sissy boy mommy boy phonesex

1-844-332-2639 ext. 222

It’s so hard to sit and wait. Every day I would send my precious boy off to school, his darling little face, his curvier than average body, that sweet fragility of his, and watch him struggle so hard to be one of the boys. He would come home upset that the boys in his gym class tease him and give him such a hard time. He is so precious. He has his little “girlfriend” but I see the way she looks at him. She sees him as a friend not as a boyfriend. My sweet boy has no idea that in fact he is and always has been a precious perfect little sissy boy. Continue reading Mommy’s Special Boy Phonesex

The Ultimate Sissy Phone Sex Experience

                Sissy Mistress Elaine   844-332-2639 ext 250

No matter what kind of Sissy you are, a Sissy Slut, a Feminine Sissy,  Sissy Maid, Cuckold Sissy let me take control of you. I will emasculate you and make your phone sex call one you will never forget…….

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Turning My Son Into My Daughter Phonesex Makeover

My sissy son makeover

1-844-332-2639 ext. 222

I had always known that my son was much more like me than his father. I had never said anything to him about it before but I knew there would come a day when he would want to talk about it. I took his laundry hamper to the laundry room and while I was separating out the clothes I found a pair of panties in there. For one moment I thought maybe he had been fucking a girl in his room but then I found another and another pair and I knew that these were no girlfriend’s panties.

I thought it was time to confront him. I walked to his room and found him working on his homework. “Jay, I was wondering, whose panties are these?” I asked him, holding the them up for him to see. He thought about lying for maybe a second and then he said they were his. “Yours? Are you wearing panties now?” I feigned surprise. He shrugged “I just like the way they feel better.” his face reddened and he asked if I was mad. I told him I wasn’t mad at all. I had expected this for some time now and was all prepared. Continue reading Turning My Son Into My Daughter Phonesex Makeover