Sissy In The Making: The Intense Femdom BDSM Transition of a Man to a Sissy

For a time, Olivia massaged his lower legs, then his knees, and then his thighs. Tim could smell the floral scent of the lotion. Normally it enticed him, but tonight he was feeling a little sick to his stomach. What was she doing to him? Olivia began to massage his inner thighs, then closer towards his groin. His clitty bobbed around eagerly, and a gasp escaped his lips as she wrapped her slick fingers around him. She stroked up and down a few times and just as he was accepting her rhythm she withdrew and moved her hands to his balls. She gently massaged them as well.

“Mmm…” Tim said. “You can call me sissy all you want as long as you keep this up.”

Olivia was silent as she continued her erotic massage. She moved about, concentrating on his clitty, then his balls, then his inner thighs. After several minutes, she ventured down further, to his perineum and then she did it… she brushed against his hole.

“My gosh, what are you doing, umm… Ma’am?” Tim asked.

“Be quiet, sissy. I don’t want to hear another word from you.”

Olivia pressed gently against his hole, then rubbed his perineum for a few moments before returning to his most sacred area. Tim tried to relax and let her have her way, and as he did he felt her fingertip enter him. The feeling was totally foreign, but blissfully exciting. He moaned deeply as she pressed in further. Within seconds, her entire finger was buried in him.

“Do you like how this feels, sissy?” she asked, using his new name.

“Yes. Yes, Ma’am,” Tim replied, moaning and breathing hard.

“Good. I’m glad you enjoy having your pussy fingered.” Did she just say pussy fingered? It all seemed too much for Tim. In just a couple of days he had gone from being businessman to housewife and sissy.

Olivia began to withdraw her finger, only to plunge it in again. It felt abrupt, and Tim found himself wishing she would go deeper. Of course, he was far too ashamed to ask for such a thing. Still, it was almost as if Olivia read his mind. 

“I have your surprise now,” Olivia said proudly. She held aloft a small buttplug. It was thin and narrow, but about four inches long. It was clear that it would go much deeper than her finger.

“Hold your legs up in the air so I can fuck your tight pussy, baby,” Olivia purred. Tim immediately reached back behind his knees and lifted his legs. As he pulled his knees in to his chest, he pondered his situation. She asked him to expose his hole for something that looked all too much like a cock and he didn’t even think twice.

“Now, here comes to cock,” she teased. And with that, she plunged the plug deep into his hole. Tim gasped, both out of shock and extreme desire. It felt so good deep inside him. He felt aroused as he never had before. Tim began humping the air wildly, thrusting his hips around.

“Oh, I see my sissy likes it. Say it! Say, ‘I’m a sissy and I like it!’” she demanded.

“I like it,” Tim admitted.

“That’s not what I said,” she cried, smacking his exposed ass again. “Now say the whole thing. ‘I’m a sissy and I like it!’”

“I’m a sissy, and… and I like it,” he said, feeling his manhood disappearing. He felt worthless, like a sissy. He felt pathetic and used, and yet oddly so aroused.

“That’s right,” she said as her hand moved down to her pussy. “You are my sissy, and this is just the beginning.”

... The above excerpt is from my latest publication, "Sissy In The Making: The Intense Femdom BDSM Transition of a Man to a Sissy" 

Read it today!