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Writer's pictureLady Phoenix

Cuckolding the Sissy


She was about to be cuckolded by a hot brunette T-girl and her delicious blonde Mistress.
She was about to be cuckolded by a hot brunette T-girl and her delicious blonde Mistress.

Chris was as beta as they come. An emasculated simp unworthy of satisfying any woman. And here he was now in my Lair, begging for my attention. This was not entirely surprising as I was dressed in a short black figure-hugging leather dress, high-heeled boots with fully-fashioned stocking tops temptingly visible just below the hem of my dress. With my cascading wavy blonde hair and luscious red lips on show, he didn’t stand a chance. There was only one thing for it: Chris needed to be completely sissified, fully feminised and learn his place in the pecking order.


A partial transformation was necessary, moulding this pathetic specimen into a form that was easier to humiliate and degrade. The pink satin was out in force, with white nylon stockings and a silky suspender belt at hand to remove any trace of masculinity in this very silly outfit. I placed a pink collar around his neck with the word “Sissy” spelt out in diamanté letters. With a pink wavy ombré wig on, Chris had become Christina, and the game was only just beginning, down this rabbit hole of emasculation. And speaking of holes, I wanted to make sure that Christina knew how her genitalia and anus were to be used now: her cock caged in a small pink pussy-shaped chastity cage, and her ass as a tight little sissy hole, purely for my entertainment and amusement. The cage was tucked away in a pair of ultra-shiny pink satin panties.


I pushed Christina over my spanking bench and restrained her wrists, bending over her and whispering in her ear as I did so. “You’re going to get what you deserve for clearly being a bad sissy slut. But also you’re going to learn that you can’t have everything you want, no matter how hard you try to impress.” I viciously pulled down Christina’s panties, leaving her exposed and helpless, and slipped on a latex glove, smearing my fingers with lube. I began to finger her tight hole, first with one finger then with two, paving the way for something even bigger. Stepping into my leather harness and fastening it securely around my hips, I selected a dildo of an appropriate length and thickness to stretch Christina’s sissy hole and to show her who her owner was. I spat into her hole and began to slide seven inches of strap-on cock inside her. She moaned as my strokes grew deeper inside her greedy hole and she begged for more. My thrusts grew faster and harder until Christina cried that she could take no more. “You can take no more?! Well that’s a damn shame as I really could do with being filled by a big hard cock right now! I thought you were better than that and could take a good pounding! Clearly I was wrong!”


It was just at that moment that there was a confident knock at the door. “Come in,” I answered. The door to my Lair swung open and there she was. A beautiful slim brunette dressed in heels and a short red shiny dress strided in and said “Hi!” very warmly.


I moaned as Ama’s strokes inside my tight wet pussy got faster and faster, my pussy juicier and juicier.
I moaned as Ama’s strokes inside my tight wet pussy got faster and faster, my pussy juicier and juicier.

“Well,” I smiled at the gorgeous brunette. “How wonderful to see you!” We embraced as she glanced at Christina. “Oh, just ignore that one. I had high hopes for her, but sadly she’s nowhere near as hopeful as I first thought. No promise whatsoever. I would suggest the two of us just carry on…as we want. And I do have to say that you look incredible today Ama,” I said as I touched her shoulders and planted a lingering kiss on her lips. Ama reciprocated passionately. It was all about me and her. The sissy was not of interest to us sexually. A pathetic attempt at femininity. There was only one thing for it. Ama and I would have our fun while Christina watched.


“Let’s restrain her to the bed!” I commanded, as I clasped the sissy’s wrists and tied them down tightly while Ama dealt with her ankles at the other end of the bed. A spreadeagled sissy getting just what she deserved: an extremely hot erotic show of what she could have had but wasn’t quite good enough to get. Once secured well enough, I climbed over the sissy in my lingerie and stockings and manoeuvred myself so that my pussy was hovering just above her face. I grasped my panties and pulled them to the side. Ama positioned herself behind me, ready to fuck me doggy-style, and began to feed her thick 8-inch cock into my horny pussy. Horny, but not as horny as the sissy below me, with my pussy just inches from her makeup-smeared face. She was about to be cuckolded by a hot brunette T-girl and her delicious blonde Mistress.


I moaned as Ama’s strokes inside my tight wet pussy got faster and faster, my pussy juicier and juicier. The sensation of that cock sliding in and out of me was almost as divine as the forlorn, dejected expressions on Christina’s face. She wished so much she could be involved in this salacious spectacle, but all she could do was watch and wish I was her. Or she was Ama! We were both having a great time, my cunt practically dripping with excitement onto Christina’s face. Ama’s cock felt incredible inside me, with every thrust of her hips bringing me closer and closer to a shuddering orgasm. The sissy whimpered as my cries of ecstasy crescendoed to a fabulously loud volume, extolling the pleasures of Ama’s meaty dick. My pussy was bursting with sheer pleasure, my juices showering the sissy, giving her a taste of what she’d been missing. As I came, my clenching pussy was about to bring Ama to a simultaneous climax, and she sighed as she exploded inside me, into the condom. That condom was completely filled with cum! So why not give Christina another taste of what she had missed?


Ama’s cock felt incredible inside me, with every thrust of her hips bringing me closer and closer to a shuddering orgasm.
Ama’s cock felt incredible inside me, with every thrust of her hips bringing me closer to a shuddering orgasm.

Ama and I laughed at our frustrated sissy as we prised her mouth open and emptied the contents of the condom down Christina’s throat, a wonderful way to complete the humiliation! Our sissy opened wide and devoured every single bit of her treat with gusto. Christina had been cruelly denied cock and pussy, but at least had had a taste of our supreme enjoyment.


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