Randy had to breathe deeply five times before opening the door for Chelsea, his Cuddle Buddy for the night. It was a first for both of them. She hadn't stayed overnight with a client before, and he'd never paid someone to sleep in his bed. The few cuddle sessions they had, he'd been most satisfied with her service and the easy access to her unconscious body when she accidentally fell asleep.
"Randy!" she squealed and threw her arms around his neck. He pressed her trench-coat-covered body to his sturdiness and inhaled her sweet vanilla scent.
"Hi, Chelsea. Welcome back," he said, rubbing her back firmly.
They parted and she turned back to the door to grab her overnight bag from the hallway. "I brought coffee to help keep myself up," she said holding a giant to-go coffee cup. "At least, until actual bedtime so you can get all the cuddling you need before we hit the hay."
The giant gulp she swallowed made Randy smirk. Though he'd prefer she fall asleep sooner, there was something he'd put together before she arrived. A hidden camera in the toilet would capture her pissing out all that coffee throughout the night. His ex-girlfriend never let him explore any fetishes or kinks that interested him like piss play. She was very vanilla while still being extra controlling. He wasn't into femme dommes--she ruined that for him.
Chelsea removed her coat, revealing a pair of jean shorts and a tank top. Randy stood before her ready for bed in his boxers and T-shirt.
Seeing his furrowed brow, she said, "Don't worry, silly. I'll change into the silk nighty you requested after we eat."
While they slurped down the spaghetti he'd made, she shared that her hobbies of reading and painting were the reason she needed this side hustle as a Cuddle Buddy. Randy nearly fell off his stool when she showed him a photo on her phone of her latest painting--a self-portrait, nude.
"So," he said after choking on his water, "you're into realism then?"
His eyes slowly appraised the brush strokes of her pillowy breasts with one arm above her head. A slender finger from her other hand rested comfortably between her delicately parted lips and--
She snatched her phone from him and slid it down the bar away from them, her cheeks deepening in color.
Looking anywhere except his direction, she said, "It's my first self-portrait. Do you think it's any good?" She sipped her coffee and dribbled a little onto her tank top before he could answer.
She jumped off the stool and excused herself to the bathroom with her bag.
To his disappointment, she didn't use the toilet before exiting. Her black silk night gown hit her mid-thigh and tented at her nipples with thin strings over her shoulders.
They got comfy on the couch to watch some TV, sharing their favorite shows with each other. She draped her smooth legs over his lap, and he massaged her tender feet. Kneading her arcs made her moan enticing his cock to stir. He wondered how it would feel to rub her soft soles over his hard shaft.
During the last show she climbed behind him, to his dismay. Her legs spread wide against his waist and wrapped around to rest on his thighs. She held her arms against his chest, her face pressed into his back, and told him to lean into her.
"Won't I crush you?" he asked, not budging from the edge of the couch.
"No, it's okay. I like feeling weighted down." She pulled him toward the couch, toward her. "Just try it."
Slowly, he allowed his weight to distribute over her little figure. She hummed relaxing sounds and ran her hands over his shirt, relishing his abs and chest.
This position didn't give him much opportunity to feel her up or feel her much at all. The anxiety of crushing her bones and squishing her organs kept him tense, despite her roaming hands. She softly stroked his throat and traced a line through his sternum and ribs to his belly button. Just when he was getting a little relaxed, she stiffened.
"Oh. I guess you're squishing the pee out of me. Gotta tinkle!" She tapped his shoulder asking him to release her.
The thought of keeping her pinned while she struggled and making her piss down his back gave his cock life. It took all his willpower to let her go.
When she closed the door, he dove for his phone on the coffee table and opened the hidden camera app.
The lid opened and her ass hovered over the seat, bare and beautiful. Her folds were puffy and bursting from between her thighs. At first only a dribble released. He grabbed his hardening cock through his boxers. He was such a bad guy. This was such a violation.
Her stream steadied and he heard a sigh come through the bathroom door. The coffee seemed to go right through her with the help of his 200 pounds on her bladder. She ended with a few squirts before sweeping toilet paper over her bits and flushing. He quickly exited the app and put his phone back on the coffee table.
"Shall we move to the bedroom for the night?" he asked when she opened the door.
"Sounds good to me!" She grabbed her overnight bag and brought it to the bathroom to brush her teeth.
He joined her and felt a familiar comfort. The domesticity of brushing your teeth with someone else was another kind of cuddling. Like an emotional support person...who later turns into a sex doll.
She climbed into the bed with her ass in the air before bouncing into a comfy position on her side. He could swear she was being seductive but knew that wasn't part of the service. He took off his shirt, leaving only his boxers. Getting into bed on his back, she curled up beside him. One of her silken breasts rested heavily on his ribs and her head curled up under his armpit. A leg lay over his thigh and an arm across his abdomen caressed his side all the way down to his thigh. Her forearm grazed his resting cock and on her next pass she seemed to aim at brushing against him again. And again.
He moaned and brushed her hair with his fingers. She nuzzled him, flattening her breast against his body unknowingly tugging her top down slightly. He was rock hard, and it was difficult to miss hitting him now. But she didn't ask if he "needed to take care of it" this time. He wondered if she was having dirty thoughts like he was. He wondered how many of her clients she is this sexual with.
When her breathing deepened and movement ceased, he shook her shoulder and whispered her name. Her response was the same--deep breathing, no movement. He steadily took her hand and wrapped it around his cock, still in his boxers. Making her jerk him off was just the tip of what he had planned tonight. It could be his last night with her if she woke up, so he was determined to make it count.
He gently manipulated her body to face away from him for a spooning position in case she did actually wake up. He doubted it. She was the heaviest sleeper he'd ever encountered. The last few times she was over he was able to explore her breasts and finger her to orgasm without waking her up.
Her silky gown lifted easily from her flesh, sliding under her light weight. Her thong was lacy under his fingertips--so easy to move aside to make way for his rod. Without hesitation he rubbed his cockhead up and down her gash before finding her entrance.
