Creepypasta Lemons

Sissy (Toby x Clocky)

femboy, sissification, humiliation/degradation, femdom, pegging
MxF

Toby came out of the closet wearing a pair of black and pink thigh highs and a short miniskirt. He had some pretty clips in his hair to match the socks and looked like an embarrassed, shy, little sissy.
Clockwork looked up from her phone and grinned. "Wow." She exclaimed, "You look like such... a girl." Toby blushed and itched his right arm with his left hand. Clocky strutted over to him, softly touching him. "I feel like the tiniest thing could hurt you, bruise you, break you." He felt her hot breath on his ear. "I want to break you."
She roughly grabbed his arms and pulled him to the bed. "Wait here." You could clearly see Toby's bulge through his skirt, but other than that you might honestly think he was a cis girl.

Clocky came back with a collection of dildos, ranging in size, color, and style. There were a few realistic ones and a few that looked like monster/dragon dicks. There were thick ones and slim ones, long ones and small ones. Toby's eyes widened in embarrassment and the blush on his face grew.

Clocky rubbed a few of them up and down, maintaining eye contact. "Which one do you want to fuck you, Toby?" Her voice was light, sweet, innocent. Toby pulled up his shirt and hid his face in it.
"I-is thi-s n-nece-ssary?" His stutter worsened with the embarrassment.
"I want only the best for my baby girl." Clocky took a tuft of Toby's hair and twirled it in between her fingers. Toby looked at the collection and studied it. He pointed at one that was shaped weirdly. It had lots of weird bumps on it and was a bright pink color. "You want that big one inside you? Feeling greedy today, hmm? I can't wait to see how good you'll look when it's in you." She cooed, putting on the strap.

She grabbed some lube out of a drawer and kissed Toby. "Such a pretty girl." she trailed her kisses to his neck. "Such a good girl." Toby let out a breathy whine. "You like it when I kiss your neck? How about when I touch your girlcock?" She softly stroked up and down.
"M-mommy~."
"Mmm, yes, baby?"
"To-touch me more pl-ease mom-my." She grabbed the lube that she had set down earlier and squirted a bit onto her hand.

She rubbed Toby's little hole. "Are you ready, baby?" Toby shook his head softly, then closed his eyes in anticipation. She stuck a finger inside of him. As he moaned, she added more fingers and speed. "Mmm, is my baby girl ready for me to fuck her? Huh? Does my little slutty girl want that?"
"Y-yes mo-mommy please!" 
Toby couldn't handle the feeling, "Please ma-ke me cum m-mommy." She grabbed hold of his dick and pumped it up and down while fingering him.
"I want to see my baby cum first."

"F-fuck mommy~." he moaned as he came. It got all over his chest and some even got on his face.
"You look so cute like that." She positioned the dildo, looking Toby in the eye.
"W-wait I ju-st came. I c-can't ta- hgnnnn." He moaned as she stuck it inside him.
"Oh~ I love it when you make those noises. Such a good girl, my good girl." She thrust the dildo in and out of him. Toby's brain was blank. He couldn't think. His eyes were closed, and he had completely succumbed to the pleasure. Soft, but loud, moans escaped his mouth and he couldn't hold back. She was fucking the brains out of him. "Do you like this? You like me fucking you like the girl you are? Huh? Being treated like a sissy? Such a dumb whore, aren't you? You can't even think, you're just getting fucked so good."
With every thrust, she went deeper and faster into Toby. He finally came again, the sticky warm cum coating his stomach once more.

He breathed heavily as she took her strap off. "Get in the shower, you're so filthy," she chuckled, "I'll cuddle with you in bed when you're done." She set the lube back in the drawer and cleaned up. Toby took off the feminine clothes and hair clips and walked into the bathroom.