Author Archives: SissyCuckoldTrainer

Feminized Sissy Cuckold

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Sissy Cuckold Phone Sex
888 – 464 – 6465

The two women stood behind him in the full length mirror while he looked over their work, turning him into a totally feminized sissy cuckold. His skin was fresh and smooth, and he couldn’t believe how feminine his face looked. His eyelashes seemed to go on and on, and each one perfectly coated in dark mascara. His lips were plump and rosy and he held them in a pout just as they had directed him to.

“Your new face would have been finished a long time ago if your eyes hadn’t watered, and you hadn’t been so fussy”, one of them told him.

She was right, it took some time to get this look, but he knew that now that they had gotten him there that they wouldn’t let it go to waste. The same women who spoke to him walked off to set up the camera and he got nervous all over again. His girlfriend had decided on the corset that she wanted him in, and started dressing him in his blush colored satin corset. Once she had him laced in she added the matching evening gloves over his freshly waxed arms.

“Don’t you worry, you’ll be getting laser removal of most all of your hair, and in time you won’t need waxing or shaving at all.” she told him.

She guided him to step into the leg holes of his g string panties. He noticed when she slid them up over his thighs and over his sissy clitty that it looked swollen inside of the tiny crotch. His girlfriend was getting excited, and enthusiastically got him into his thigh high white stockings and then into his pink spike heels.

“Not bad for your first day as a feminized sissy cuckold.” she said as she smiled at him. “Now we have to document this wonderful event.” read more

Sissy Cuckold Exposed

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Sissy Cuckold Phone Sex
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I sat holding a lacy push up bra in one hand, and a key in the other. He had decided that denial was the best way to handle his predicament. “Look, I know that your wife’s breasts would not fit into this bra, there is no way. This is like an A cup, maybe.“ He only blushed and hung his head like the humiliated sissy I was sure he was. So I said “drop your pants, and we will see if this key does go to the chastity device that I’m guessing you have on.” Silently he unfastened his pants and revealed that he was wearing panties and a locked chastity cage. Of course the key fit perfectly into the small heart shaped pad lock holding his chastity device in place.

I immediately locked back into the closed position, and looked at him. I knew that I was right. He was a sissy in chastity and probably a sissy cuckold too. Or maybe he wasn’t yet. Maybe his wife wasn’t even involved in his sissy games. I decided to try and find out. read more

Sissy Cuckold Video

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Sissy Cuckold Phone Sex
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His eyes were locked on the video playing in front of him showing him what his wife had been up to since she started hosting her new “book club”. She was busy hosting something alright. He sat on the sofa stroking his cock while listening to the sounds of her moaning and panting while this big, muscular dude was pushing his big thick cock into her mouth. She was licking and slurping on it expertly and then suddenly she stopped, looked up at the camera and smiled.

“Hi, honey. I hope you like what you’re seeing because this is how it’s going to be from now on. THIS is the kind of cock and the kind of MAN I’ve been missing since I settled down with you. I’m so tired of faking orgasms with you and finally decided that I’m not going to,” she said, as she continued to stroke and lick the massive cock in her hand.

“Look under the bed and take the first step into your new life as my humiliated cuckold,” she said and then blew a kiss at him through the video. He hit pause and scrambled to his feet to see what she was talking about. Underneath the bed that they shared he found a gift bag with pastel pink tissue paper closing off the view of what was inside. He pulled the paper back and found pink satin panties and shimmery pink lipstick along with a note that said “No more men’s underwear for you. Your cock is barely bigger than a clit so I want it covered with panties from now on. I saw the lipstick in the store when I was buying the panties and it seemed like something a sissy cuckold should wear. So take off your clothes, put on the panties and the lipstick and finish watching the video. I’ll have another surprise for you when I get home.” read more!

Cuckold Sissy Cocksucker

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Sissy Cuckold Phone Sex
888 – 464 – 6465

The man was fucking his mouth furiously, smearing his deep red lipstick
all around his face, and onto the man’s cock. He reached and felt his
nipples, they were so hard inside of his frilly pink lace bra. The man, his wife’s lover, removed his hard huge cock from his mouth and told him “You’re not bad for a sissy cocksucker. Now I want you to jerk me on your face and let me feel how much you admire the big cock that keeps your wife happy.”.

He started rubbing his shaft with both hands. He’d never felt so humiliated and vulnerable in his life before and yet his own little cock was throbbing inside his pink lace sissy panties. The subtle sound of his wife’s heels on the floor behind him brought him back into the whole moment. He heard her giggle. “He’ a born sissy cuckold, isn’t he?” she said. read about the rest of his humiliation

Sissy Cuckold Wedding Night

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Sissy Cuckold Phone Sex
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She was the hottest girl he’d ever dated so he hadn’t resisted too much when she started making him wear panties long ago. He knew his small cock didn’t satisfy her so he pretended he didn’t know that even after they got engaged, she cheated on him with other men. He flushed with humiliation every time she laughingly called him her sissy cuckold.

She’d made it very clear when she agreed to marry him that that his married life would be all about her needs. But he never knew that he would really see the woman he had just exchanged vows with enjoying her wedding night with another man. No, not another man, but a MAN. She tossed her head back and purred as her lover filled her in a way that he never could. read about the rest of his humiliation

Sissy Cuckold Phone Sex Training

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You might think that being a humiliated cuckold is as far as it might go during a cuckold phone sex call, but there is another level of cuckolding that you are going to experience when you call one of us at Sissy Cuckold Phone. Because we are not just going to cuckold you, We’re going to turn you into a sissy.

It’s a natural progression to become a sissy cuckold. Most cuckold phone training Femdoms see no
point in you cucks trying to cling to the last threads of your supposed masculinity and dignity. Sissy training will turn you into a panty and lipstick wearing sissy cuckold who will be kneeling by the side of the bed ready to fluff dick or lick creampie for your wife or girlfriend and her stud.

You will be doing all the household chores anyway, like cooking, laundry and cleaning, so you might as well be dressed like a French maid. Your wife or girlfriend will appreciate that you are no longer just a cucky, and that you are now a sissy cuckold who she can order around like a housekeeper. Don’t be surprised when her stud shows up with all of his laundry that you will be expected to do while he is taking care of things in bed, something you were never able to take care of.

At Sissy cuckold Phone, what we do with our cuckie boys goes beyond cuckold phone training. Our cuckolds learn to embrace their new lifestyle of becoming a sissy cuckold. You may not think you want to be a sissy, but it will feel natural once you are, because our sissy training program is very clever and subversive at reprogramming your cuckold mindset. Of course, some verbal humiliation cuckold phone sex will help break down any mental barriers you have about giving up all your manly underwear, watching sports and anything else in your life that will not fit into your sissification. It’s time to begin your sissy cuckold phone training now!