Cuddle Buddy Services Pt. 01

Randy opened the door to find Chelsea standing on the other side in long-sleeved, footie pajamas of light grey flannel. Her soft brown hair was in a relaxed bun with strands falling on her face. The slender curve of her neck brought his eye to her barely exposed clavicle leading to the long zipper between her breasts that ended just below her waist.

She tucked a few loose strands behind her ear and adjusted her shoulder bag. "Randy?" Her wide eyes we expectant with eyebrows raised.

It took him a few moments to respond. "Uh. Er. Yes, come in, um, Chelsea. Right?"

She smiled a beautiful, full-teeth smile and winked at him. "You got it!"

Her walk was smooth and confident as she set her bag on the kitchen counter just inside Randy's apartment. Her little apple ass rocked across the tight fabric of her onesie making her way to the couch.

He followed and sat beside her perfect form, hands on her knees just perching on the cushion. "I thought we could start with some ground rules so we can get straight to the good stuff," she said.

Nodding he folded his body over and crossed his arms to conceal his erection.

"I remember from your questionnaire that this is your first time with a Cuddle Buddy, right?" She nodded along with him holding eye contact until he looked at the ground. "It's okay. Lots of people haven't tried it before, and human touch is so important."

She placed her hand on his shoulder scattering goosebumps over his back. He looked up at her and tried to smile.

"So," she continued, "a few things to keep in mind: 1. Our bottoms are always covered with fabric; 2. No kissing or fluid exchange of any kind.; and 3. Always let me know if you are uncomfortable--physically or emotionally--and I will do the same. And to be frank, boners happen. They are nothing to be ashamed of and shouldn't be ignored. You can excuse yourself to take care of it or we can change positions. We can even acknowledge it and let it be. It will be something we figure out together to find what works best for you."

His breathing quickened with her talking in such a direct and dirty way. Knowing his face was bright red, he averted his gaze again. She moved her hand from his shoulder to his hands. Apparently, he'd been wringing them. They were sweaty and red with irritation but splattered white where he drew the skin taught across bone and tendon.

Her touch on his skin calmed him. The knee he didn't know he was bouncing grew slow then still. His breathing deepened and he smelled her enchanting scent--jasmine.

"Why don't you briefly tell me why you reached out to Cuddle Buddy Services and then we can get started." She inched closer to him rubbing his exposed wrists and hands.

Closing his eyes helped him feel like he wasn't really admitting any of his problems. In the dark, he was alone, and she wouldn't hear him tell her that he hadn't been touched in over a year. That his ex-girlfriend used sex as a weapon and he hasn't experienced a woman's touch since he grew the backbone to dump her.

"Thank you for sharing that with me Randy. Now, do you have any questions or places you don't want to be touched?"

"Oh god, no. Please touch me everywhere. Anywhere. All the time." His desperation was humiliating but he didn't care. He didn't want her to stop, ever. She was so gentle and soft with him.

Without giggling, as he'd expected, she said, "No problem. And it seems skin-to-skin is very soothing for you?"

He opened his eyes to find her face close to his as he nodded.

"Okay. Places I don't like to be touched are my ears and my eyes. Other than that, have at me. Are you ready?"

Nodding vigorously, he sat up straight waiting for instruction. She asked about positions he wanted to start with, but he was at a loss, so she suggested a simple hug.

They stood and wrapped their arms around each other. She rubbed her hands around his cotton-covered back and he mirrored her motions. His hardon had disappeared while he revealed his embarrassing dry spell before, but pressing his groin against her now brought it back to life. Hoping his jeans kept him covert, he decided to ignore it until she said something first.

He looked at her ass sticking out from her frame and dipped his hands lower with each circle around her back. Eventually, his rounded movements included both of her ass cheeks being lightly grazed.

"Mmm, this is nice," she purred. "Why don't you go change into something more comfortable than jeans and maybe a tank top for more skin-to-skin opportunities? And I'll roll up my sleeves."

Randy just about ran to his room and shuffled through his dresser for some basketball shorts and an undershirt. Tearing off his clothes, including his boxers, he adorned his new outfit and tried to walk back out into the living room at a reasonable speed.

Chelsea had turned on the TV and found a movie. "Usually, watching a movie or show can help break the tension and awkward silence. How about this one? And then we can spoon on the couch."

She picked some action movie he'd never heard of, but he agreed, and they got into position. With his height at 6 foot and her at 5 1/2 feet, they naturally ended up with him as the big spoon, his back against the couch.

Using pillows and blankets he'd brought out before she arrived, she adjusted herself endlessly, rubbing her ass against his hardon. She pressed her body as close to him as possible to keep from falling off the couch and instructed him to wrap his top leg over hers to help anchor her. Then she used his lower arm as a head pillow and drew his upper arm across her tummy and onto her breasts.

He was stunned. "Oh, I thought the website said this area was off limits, same as genitals." Regretting his words, she sat up tugging her legs free of his hold.

Facing him, he had to look up at her seeing breasts then her face. "Sorry, I forgot to explain. I don't think that matters so much. Touch is touch and if our intention is not sexual, then it's fine. I don't personally feel arousal when my nipples are touched and understand that a hard nipple under fabric can be a stim for some people. If I can touch your chest, you can touch mine. Does that work for you?"

His jaw hung open as he nodded. This was a different experience than he expected. It sounded so freeing to be able to touch a woman without worrying about the inevitability of sex or if she'd smack him instead.

"As for genitals. Like I said before: they stay covered. Spooning for instance makes your genitals touch my ass so, what, are we going to get rid of the most popular cuddle position? No. So, if your hand or anything else brushes my genitals I will tell you if I am uncomfortable. And you can do the same. We don't always know where everything is laying, or uh, standing," her eyes darted to his groin, "so it's bound to happen. We don't need to make a big deal of it."

Randy found was lost for words and just kept nodding.

"Just please don't mention it in any reviews or to my employer because they are pretty strict about it." She rubbed his bare arm and squeezed up to his shoulders.

He rubbed her leg and tugged on her onesie to get her to lay back down. "Okay, I promise."

She got back into her extravagant pillow-couch-Randy bed and returned his hand to her chest. His mind raced with all kinds of things he could get away with. Could he just straight up masturbate on her? Or masturbate her over her silly pajamas? Make her cum without penetrating her? Could that be cuddling?

"Before I hit play," she said without turning around, "do you need to go take care of that?"

He was used to edging. It was one of his tactics he used to feel an intense orgasm while he was all by himself this last year. He'd tried a number of things to feel good again, but nothing worked. So far, Chelsea was working for him.

Pressing his cock against her ass he said, "No, I'm okay."

She pressed her ass back into him and said, "Okay," before starting the movie.

He didn't watch a moment of it. His eyes stayed on Chelsea the whole time. Admiring her slim form and wondering what she looked like naked. Did she have any birthmarks or scars? Maybe she was the kind who had tattoos and didn't want to show them when she first met a cuddle client.

Dragging his leg over hers, he cocked her body slightly in his direction. Her breasts lay prominently on her chest, the top globe seeming flatter than the bottom. With her hands tucked under her head, caressing his other arm, she left a clear path for him to fondle her plump tits. When he squeezed the bottom one, he realized she wasn't wearing a bra and groaned as he pressed his hips into her back, feeling her ass crease even through their clothing. Was she wearing underwear?

He played with her breasts and rubbed her tummy as the movie went on, noticing her nipples getting hard under the fabric. Taking her advice, he enjoyed the feeling as he slid his fingers back and forth across the little bump noticing that it flexed back and forth with the weight of his hand.

Her breathing deepened, steadied, and her fingers ceased dancing over his forearm under hear head. "Chelsea, you okay?" he whispered.

With a snore in response, he realized she'd fallen asleep. This was his chance to really feel her little titties. Slowly, he tugged the zipper of her onesie. It slid more easily than he expected, gliding over the teeth in silence. He was pleased to find the fabric parting ways to expose her smooth skin to him.

Not wasting time, he dipped his hand into her top and cupped her warm, soft breast. As if it was made for his grasp, every inch of his hand was covered by breast and none spilled through his fingers. If he could be her bra, he would hold her boobs up for eternity.

Squishing her titty tissue in his hand, he gently humped her backside. The tip of his dick wanted in so badly, but the fabric kept it at bay. He imagined the silky material of his shorts were her silky insides and the resistance from her pajamas was the pressure of her contracting walls. When he came in his shorts, he thought of decorating those walls for her. Splattering white across her pink secret sauna.

Knowing he was lucky she didn't stir at his suppressed pleasure grunts he quickly zipped her back up and placed his hand on her innocently covered breast.

The credits rolled and he tried to wake her up, but it proved to be a challenge. He had to shake her whole body like she was going through an earthquake to get her big eyes to flutter open.

"Oh, no! Did I fall asleep?" she asked, looking around frantically as she sat up. "What time is it?"

"The movie just ended," he assured her, covering his wet shorts with a pillow.

"Oh, thank goodness! If I go over time, I don't get paid for it."

"Don't worry. I would pay for it under the table if that happens with me."

"You're pretty cool, Randy," she said lightly punching his arm. "So, how was your first session. I'm sorry I wasn't more present for it."

"It was really great!" he said honestly. "I'd love to book you again soon."

"Oh, I'm so glad! Just go on the app and book me from there. And now that we've had our first session, and you've proven to not be a creep, you can also request an outfit. If there's something that I could wear to make you feel more comfortable and relaxed, I'm happy to do so." There was a customer service voice she put on while she recited her specials and add-ons like cooking for him or joining him in public for touch-comfort.

"Oh, wow. I didn't know Cuddle Buddies did all of that!"

"Yeah, some people do all of that, some don't. I'm sure there's stuff I don't do too. It's just up to the individual and their client, really."

She spoke so matter-of-factly. Like she knew he was thinking this was more of an escort service than it presented itself to be online. Maybe she hadn't actually been asleep? Can anyone really sleep that hard without drugs?

"Okay, I'll see you next time then!" She hugged him from a seated position on the couch before grabbing her bag and showing herself out.

--- --- ---

Chelsea showed up the next week in a black trench coat with her same bag. "Hi, Randy! Would you like a hug?"

She walked in and set her bag on the counter before turning to throw her arms around Randy's neck. She had to stand on her tip toes to get her cheek to touch his as they embraced. His hands roamed her body and unabashedly grabbed her ass.

"I'm excited to see you too," she said with a small laugh.

They separated and she removed her coat revealing a teal silk tank top and shorts with matching lace on the edges. She labeled it as one of her favorites in her list of outfits for her clients to choose from and he sure as hell didn't mind the possibility of snaking his cock up those little shorts if she fell asleep again.

"What are we doing today?" she asked.

He cleared his throat but did not stop his lurid gaze. "I thought we could go in my bedroom this time. There's more room for cuddling than the couch."

She shrugged and headed straight to his room where he'd changed clothes last time. This time he wore boxers and a shirt, ready for comfort and a little something extra.

Without prompt or pause, Chelsea crawled onto the bed, her ass in the air for him to watch as she made it to the headboard. She bounced lightly still on her knees. "Wow, nice bed," she said, her breasts bouncing loose in her top.

"Nice...outfit," he managed, folding his hands over his painful erection.

Her hair was down and floating around her face like a mermaid as she fluttered her eyes. "Thanks." A blush crept over her chest, and he wondered if he could get it to reach her nipples.

"Well, I'm definitely going to fall asleep in a bed like this. Do you mind if I set a timer, just in case?"

He shook his head and joined her on the bed, laying with his back propped up on pillows so he was reclined. She set her phone on the nightstand, again, showing off her barely covered ass. The fabric sucked into her precious folds, hidden from view.

"Okay. You look like you have a position in mind," she said after turning around.

He patted his lap, inviting her to straddle him.

"Like this?" It felt different with him taking the lead this time. He nodded as she sunk her crotch onto his, evidently not seeing his hardon. Her eyes widened as their genitals made contact, safely shrouded in her required fabric. "Or should we maybe do a different position?"

"No, I'm fine," he said, smiling dreamily. He was in heaven. Almost all of both of their bodies were exposed and her skin was a source of energy, of lust, of life.

Pulling her to him pressed her unsupported breasts against his chest. Even through both their tops he could feel her nipples, hard and digging into him. His hands ventured over every inch of her backside. Freely caressing her exposed ass cheeks as his circles gathered the material up into her crack "by accident". In the same vein he shuffled the back of her top up, feeling her smooth back and tracing her spine all the way to her tailbone.

She, in turn, pressed her face to his neck and brushed his sensitive skin with labored breaths. Her tiny hands trailed along his arms and chest, even toying with one of his nipples--rubbing and pinching it between her fingers.

"Sure you don't need to take care of that? It seems like it might be painful."

He insisted he was fine, but she wanted to change positions at least. When they did, he had to change his underwear because he'd soaked through his boxers with precum. Part of him wondered if it wasn't his arousal alone.

When he came back from the bathroom, she was sniffing her fingers but quickly played with her hair to cover up. His boner wasn't giving up and he found himself walking back to the bed with a massive tent, unapologetically.

"Really, you can take care of it. I don't mind. I won't look if you're not comfortable leaving me alone in your room for however long that takes."

He grabbed his cock. It never felt so hard in his life. If he hit a brick, he could probably break it with just the tip.

Jerking off with her in the room was intriguing but he wanted more than that. He needed her to fall asleep again.

"Really, I'm okay. I promise. Can we just spoon again?" He got into position on the bed and allowed his cock to continue tenting his underwear without impeding it. "I really liked that last time."

She crawled into his open arms and positioned her ass above his pole. Smart, it would probably feel like being poked in the back with a spear if she were any lower on his body. He had a great view of her slippery top falling open and revealing her cleavage nicely. His hand went straight to her breasts and fondled freely. Even when his thumb slipped inside her shirt, she didn't stop him or complain.

Her response was to rub his hand that was rubbing her nipple and caress the arm wrapped around her neck. He pressed his hips against her wishing he could rub his cock against something, but she knew just where to place it, void of any meaningful contact. His tip tapped her inner thighs but with her knees bent, it was just empty space ahead.

"I'll put on a movie," he said and reached for her nightstand, pressing her into the mattress which she didn't object to. His cock finally getting some traction and some fresh air finding its way through the slit. He grabbed the remote and turned on the TV sitting atop his dresser and leaving his cock out since she couldn't see it.

He put on a romcom, assuming that's what she would like and wasn't wrong when she said, "Oh, I love this one."

She wiggled against him and settled in for the film. He held himself still, edging himself, wetting his new pair of boxers. The only movement from him was his fingers inside her top fondling her nipples.

Halfway through the movie, he recognized her deep breathing and didn't feel her caressing him back anymore. He checked the timer on her phone and felt confident he could get in and out of her within the hour.

Venturing away from her nipples, his hand found the top of her shorts and slipped underneath to find she wasn't wearing panties. What did this girl think was going to happen? Offering her favorite lingerie to wear for perfect strangers in situations where she will most definitely fall asleep and get molested. It was almost too easy.

Not letting any doubts clear his terrible judgement, he stroked her pussy through the silk. She was puffy and soft. He couldn't wait to find out if that was all flesh or a well-kept bush under there. Since no pubic hair was poking through the fabric, he guessed she waxed or at least shaved.

To his delight, as his hand slipped under the elastic, his fingers never feeling a single hair. Her pussy was as smooth as her ass and already slick for him. He slipped between her labia and felt a nub under her folds. She took a sharp breath in, but he wasn't worried. It took so much to wake her last time--he was certain she wouldn't wake even during an orgasm.

He ventured forward dipping his middle finger along her slit from nub to anus. Retreating, he repeated his long path pressing harder on her clit and asshole with each pass until her hips responded. She pushed into his lap, wanting cock or wanting to get away from his intrusive touch. Either way he dipped his finger into her center and knew he hit gold. Hot, wet liquid spilled from her lips onto his hand.

He told himself she wanted this. That she wouldn't have dressed this way, wouldn't break the rules letting him fondle her breasts, wouldn't get into the bed with him while he had a hardon if she didn't want him to fuck her.

From inside her shorts, he pushed the bunched-up fabric to the side. His cock slid over the silk, over her slippery lips, and right into her pussy like an arm into a sleeve. The pointed tip of his cock fit easily into her hole. He pumped lightly, just jamming his head in and out of her entrance while he fingered her clit.