Happy Trails (Part 2 of 2) [mF] [masturbation] [rubbing] [just shy of sex]

“Jonathan? Are you awake?”

Olivia stands in the doorway, an ethereal vision in the pale moonlight. She is wearing a white long-sleeved t-shirt that falls just below her hips and an odd expression on her face.

“I mean, I know you’re awake, I heard you talking. You’re not on the phone, are you? No, of course you’re not. Sorry for barging in anyway.”

He opens his mouth to answer several times, but can’t quite find an opening in her babbling. Not that he has any idea what to say.

“The others, Thomas and his floozy, they’re sleeping on the couch. I couldn’t sleep, not sure why. A bit cold, maybe. Guess I should’ve brought pants.” She grins.

Part of her is very nervous, that he can see clearly. But there is something else in her voice, in her stance.

“Can I come in? Can I …”

She walks towards his single bed. He gasps softly at the sight of her tiptoeing closer, her nipples hard and pronounced under the thin fabric. She sits down on the bed and he scoots backwards. It was an instinctive reaction, to give her more space and to get his erection, now back in full force, as far away from her as possible. But she takes it as an invitation. Throwing back the covers a bit, she lies down on her side next to him. The bed is not big enough for him to do anything other than spoon her. His heart is beating in his throat as he awkwardly places his hand on his own thigh, while trying to keep his cock, straining against his boxer briefs as it is, from touching her ass. His nose is nearly in her hair. Her scent is sweet and salty and intoxicating. She feels cool against his chest. He is sure he is breathing too loud.

“I saw you watching. I mean, I think you were, right? And I think …” She pushes back into him, into his erection. “I think I like it.”

His only response is a low groan.

“Hold me.”

With a jerky motion he moves his hand to her leg. She takes it in a firm grip and places it on her breast. Even through her shirt it feels perfect to his touch. She shifts her ass so his cock nestles itself between her cheeks, before she gently moves up and down.

“Just for tonight. Do you …” There is a slight tremor in her voice. “Do you want to?”

He squeezes her breast lightly, afraid that any answer would break this spell. Her breath hitches when he takes her nipple between his fingers.

“Wait. I want- Take off your boxers.”

She hitches up her shirt as he tries to pull his boxers down as quickly as he can. Her pale skin looks delicious in the faint light. Reaching back, she takes a firm hold of his cock. Tugging on it releases a trickle of precum, which quickly covers his entire shaft as she continues to stroke him.

“I saw you looking at my ass, Jonathan.”

He moans as she presses his cock between her cheeks again.

“Use it,” she breathes, “use me tonight.”

His hand goes back to her breast with more confidence, kneading it and pulling on her nipple. He pants into her hair. His erection, so hard it is almost painful, glides along the length of her cleft. Her breathy whimpers heighten his arousal. The sensation is unlike anything he ever managed on his own. A hand grazes his balls. She is touching herself. The thought is too much for him. He pulls her into him, panting quickly. Then he lets go. With a loud, low groan he comes, shaking and shuddering, his conscious mind wiped away by pure bliss, spurting his load onto her back and ass. Coming down, he finds her hand on his ass, keeping him pressed against her.

“That was nice, but now I really need to take care of myself.” She turns her head towards him. “Do you want to watch?”

He swallows hard.

“Sit up, at the end of the bed.”

Throwing the covers to the ground, he does so. She quickly pulls off her t-shirt and goes to sit on her knees, her head on the pillow, looking back at him. Her ankles lie against his knees. Her ass, glistening with his semen, is in the air, right in front of him, her pussy wet and inviting in the dim light. He can just see her eyes twinkling.

“Do you think I’m pretty?”

He nods. To his own astonishment, his cock is already stirring again.

“Is my ass better like this?” She reaches around and lets a finger trail down from her lower back, gathering his cum. “Wet.” Her other hand goes between her legs and rubs along her labia. “Bare.”

Without thinking, his hand wraps around his stiffening cock.

“Yes, touch yourself for me, Jonathan.”

With two fingers she strokes herself, pressing just inside her pussy before stroking upwards, around her rosebud. Her other hand is making slow circles around her clit. He matches her rhythm, stroking his slick, sensitive cock carefully. In moments he is hard again. Her panting and moaning fill the room as her hands speed up.

“Ooh, I love you watching me. I’m so wet.”

As if to prove it, she pushes two fingers inside of her with a long sigh. When she pulls them out, a thin strand of her juices hangs between her fingers and her pussy, catching the moonlight.

“You make me so wet.”

He is panting heavily, his mouth hanging open, one hand working his cock, the other squeezing his thigh, as if he is still unsure whether he is dreaming. She places both hands on her butt cheeks and pulls them apart. Even in the low light he can see everything clearly now. Her pretty pussy with its swollen labia and the slightly protruding clit, her dark puckered asshole, everything slick and gleaming.

“Come here. I want you on my ass again.”

In an instant he is kneeling behind her. She grabs his cock and rubs it against her pussy, moaning softly, before placing it between her cheeks.

“Grab my hips and take me.”

With her hand pressing down on him, his shaft is squeezed from all sides as he thrusts against her. His fingers dig into her flesh. She is circling her clit and moaning, setting the pace with her own movements. From this position, he can see her face more clearly. Her eyes are closed, her brow furrowed. She looks more beautiful than he has ever seen her, so open and willing in front of him. And yet somehow she is still in control and he is a servant to her arousal. A willing servant. Despite his earlier orgasm, he is nearing the edge again. Tensing up, he tries with all his might to postpone his climax. But she opens her eyes and looks him in the eye.

“I’m close. Come for me”, she pants, pushing down on his grinding cock. “Come now.”

Two thrusts are all he can manage before pulling her hips into his with a loud groan, spurting his semen over her back. The moment the first hot droplet hits her skin, she moans, wails almost, before she starts to quiver. Hesitantly at first, her body shakes harder as her moan crescendos, until she screams, short but loud. Suddenly exhausted, he collapses onto her, his shrinking cock still snug between her ass cheeks. They fall sideways, spooning again. He embraces her and she snuggles back into him.

“Good boy”, she whispers, “I think we can consider that favor fulfilled, no?”

He smiles into her hair. His breathing comes slow and steady and he feels at peace.

“Thank you, Liv.”

Within moments, they are asleep.

 

Jonathan wakes with the sun on his face, alone in his bed. For a brief instant, he is sure it was all a dream. How could it not be? But when he rolls over, the sticky, crusted juices that cover his abdomen and his pubic hair assure him that it was not. He chuckles, then frowns. Now what? Are they an item now? Will she avoid him? Despite the short night, he feels refreshed. Despite the uncertainty, he is happy. Grabbing some fresh clothes and toiletries, he heads to the bathroom in his boxer briefs. Olivia is sitting at the kitchen counter, an empty bowl and a mug of coffee in front of her. She smiles and winks at him. His stomach flutters and he grins, relieved. She nods towards the couch. Kacey is lying on top of Thomas, both of them partially undressed and snoring softly. Jonathan makes a shaking motion with his hands, but she shrugs and shakes her head. Again he grins at her, before entering the bathroom. The shower is a lot more relaxing than yesterday and when he comes back to the kitchen, there is a steaming mug of coffee waiting for him. He picks it up and then freezes, mug halfway to his open mouth. Olivia is bent over, unloading plates from the dishwasher. She is already wearing her walking boots, but has swapped out her jean shorts for a short, tight skirt. It is black and stretchy and has ridden up to expose the bottom of her bottom. His pants seem to tighten. He can see just the hint of her red panties. She looks back at him without standing up, her face lighting up when she sees him staring.

“You are incorrigible, Jones.”

He blushes but doesn’t look away. Only when she stands up, still beaming at him, does he turn his attention to his coffee. She goes to the living room, brushing past him and lightly squeezing his ass.

“Maybe,” she whispers in his ear, “maybe we can play again sometime.”

She walks over to the couch and slaps both hands on the backrest.

“Rise and shine, cupcakes!”

Kacey jerks upright, disheveled and confused. Thomas just groans, clamping his eyes shut.

“We’re almost ready to go”, she continues in a cheery tone. “There’s coffee in the pot, and the bedrooms have already been cleaned. So, you know, happy trails.”

Jonathan stifles a laugh at the deadly look Kacey shoots her. He assumes they will not see her again after today. Not because of anything anyone did, but simply because that has become Thomas’s MO over the last year. In this case, though, it is probably for the best.

“Are you coming?” Olivia asks, standing by the door with her rucksack in hand.

“I’m there”, he says and runs off to collect his own backpack.

When he returns, Thomas and Kacey are each nursing a cup of coffee, not quite ready to face the world yet. Olivia picks up her backpack and opens the door. He follows close behind, looking back with a smirk.

“Remember to be home before dark.” He feels dumb the moment he hears himself.

He steps outside still looking behind him and bumps into her. She smiles up at him, her skirt up above her butt and his crotch against her panties. She pushes into him. Her heat seems to emanate through his jeans and he gasps softly.

“Thanks,” she says, “I had a lovely time.”

With that, she takes a step forward, pulls her skirt down, hoists her backpack on her shoulders and starts walking. He just stands there for a moment, slack-jawed and awestruck. Then, shaking his head and closing the door, he hurries after her. Just before the door closes, he hears Thomas’s voice, just loud enough for him to hear.

“Assholes …”

Source: reddit.com/r/sexystories/comments/djlsl3/happy_trails_part_2_of_2_mf_masturbation_rubbing