Night Out at the Pinky Finger Ch. 03

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Ken is confused.
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Part 3 of the 5 part series

Updated 06/07/2023
Created 10/15/2015
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He felt a little dizzy going over the night in his head. She is a he, but she...he...it...is really cute. And it felt so good holding...her, he anchored that word firmly in his mind, in his lap. He was starting to get a headache trying to process everything that had happened in the last...how long had it been.

Before he could lose himself even further down the rabbit hole, Cindy grabbed his shirt with both hands and kissed him deeply, pressing her nipples into his chest.

Pulling away from him she leaned in to whisper in his ear.

"You need to relax, baby. You're getting nervous again. I can feel your heart pounding."

He craned his neck forward and kissed her again, but she pulled away and looked down.

Following her gaze, he found his hand resting on her legs with his fingers stroking the inside of her thigh.

"Go ahead, baby. It's alright."

He moved his hand up and cupped the bulge in her panties. It didn't fill his hand, and he pushed up on it, feeling the heat of her package.

She giggled again, and he looked up at her quizzically.

"What?" she said.

He struggled to find the words and finally said, "You're still soft. We've been making out and feeling each other up for a while, and you haven't gotten hard this entire time."

She screwed up her face and tried to look serious for a moment, but it only made her look cuter. "Rule number one: A good sissy does not let herself be distracted by her little clitty. The customer always comes first."

Seeing the confusion on his face, she kissed him again and said, "Relax, baby. We're having fun."

He sat back a little bit and stroked her little bulge through the satin. She was still looking at him intently, so he slid his hand under the waistband of her panties and felt the soft skin of her "clitty."

He traced his fingers along the limp shaft and to the head, rubbing it with his thumb and stroking down the shaft with his fingers.

She gave him another quick kiss and a sly grin. "It's not going to get hard, baby. A good sissy doesn't get hard, and I am a very good sissy."

She took his other hand and moved it to cup her ass again, and he found himself tracing her waistband around to the small of her back. She adjusted herself in his lap to give him better access and giggled when he looked up at her again.

"Relax, baby. We're just playing, and you haven't finished exploring yet."

He had one hand down the front of her panties, and with the other began to trace the crack of her ass.

She rolled her hips and pressed herself into his fingers, helping him find her tight asshole and letting out a pleased sigh when he did.

He massaged her entrance with a fingertip and teased her crack before returning to tap it lightly, producing coos of delight. He repeated this several times until she rolled her hips again and slipped his finger inside her.

He stopped and looked at her for guidance, but she had her eyes closed and a look of bliss on her face. He wiggled his finger and pressed into her further.

She made a quiet humming noise as he twisted his finger around inside her, pressing against her ring. He stopped there and withdrew his finger, sliding his hand out of her panties.

She opened her eyes and looked into his face. She looked down and whispered demurely, "Please don't stop."

"What was that?"

She looked back up at him and said, "Please don't stop." She paused for a moment and then added, "You don't have to worry about it being dirty. I keep it clean, baby."

He couldn't think of anything to say, so he slipped his hands back under her panties and slid his fingers down her crack until he found her asshole again. He slipped his finger inside her, pressing past her sphincter and deep into her ass. He was amazed at the spongy, velvety texture of her ass.

He wriggled his finger insider her, listening to the sounds she made as he probed her insides. When she responded to a certain spot, he drew his finger almost all the way out of her ass before sliding back into her, seeking out the spot. She moaned low in her throat at this new stimulation, but Ken had trouble working just one finger into her and keeping up a steady rhythm. He pulled out of her and added a second finger, opening her up more and allowing him to reach deeper inside her.

She pressed herself tight against him, and he could feel her breathing increase. She started making quiet "uhh" noises as he quickened his pace, and he began rotating, curling, and wiggling his fingers as he drew out of her, sending her over the edge.

She twitched against him, letting out a quiet squeak and dribbling cum into his other hand.

As she stilled in his arms he gently pulled his fingers from her ass, drawing another gentle sigh.

He withdrew his other hand from her panties and found it covered in watery, white cum. He looked around for something to wipe his hand off with.

Feeling him move, Cindy opened her eyes and, seeing his hand covered in cum, sat up.

"Let me clean that up for you, baby."

He could only stare in amazement as she leaned forward and took his fingers into her mouth. She dutifully licked each of his fingers, lavishing special care on the task. With his hand clean she swallowed her own cum, giving him a shy smile.

He didn't respond for a while. Totally overwhelmed, his eyes had unfocused and he seemed to stare at her and past her at the same time.

He was having trouble collecting his thoughts, and it didn't help that he could feel Cindy's warm, wonderfully cute body pressing into his. His thoughts kept returning to how amazing this beautiful assgasming sissy was. He felt so confused. He was a guy...and guys are interested in girls. Cindy was...something else, but she looked like a girl and she acted like a girl. His head started spinning again as he wrestled with definitions, trying to put his world in order again.

He blinked as Cindy's voice finally penetrated the haze that had muddled his throughts.

"Baby?"

He focused on her and for a moment the world seemed to snap back into focus. Her worried eyes were searching his face, and as he focused on her again she offered him a soft smile.

"Relax, baby. You did great."

He felt the tension leave himself as her words settled deep inside him. He was enjoying himself, and Cindy was happy. He couldn't figure out why he had been so worried.

Seeing him relax, Cindy leaned in again and teased his lips open with her tongue.

Ken surrendered himself to the feeling as their lips met. His hands eagerly caressed her body, and he felt her quiver and press herself against him. This felt so good...so right.

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