Tag Archives: sissy cuckold

Sissy Cuckold Exposed

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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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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
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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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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