There was no lewdness in Kylie’s expression or posture as she asked the question, no bitten bottom lip, pout, ass wiggle, or striptease. Just a simple invitation given in a voice soft as goose down.
They had met online three months ago, in September, and she had flown to a city halfway across the country to visit Tom. She had been kind enough not to comment on the small, old apartment and secondhand furniture, the best a fresh out of school Tom could do on the bottom rung at the ad agency. He’d scrambled to buy more dishes and glassware so it didn’t look like he managed with just the one of everything.
He was a perfect gentleman from the time he picked her up at the airport, offering her his small bed while he slept on the couch the first night. He’d agonized over whether to kiss her at the baggage carousel, or if she would think it was too forward. He had opted for a hug.
Now, on the second night of her stay, these eight simple but seductive words.
Tom was speechless. She was beautiful, and he was smitten with her bright, positive spirit. But any sex would be his first in years.
He’d lost his virginity to a stranger while in yet another faraway city while he was on his internship, with an older woman who plucked him out of a bar crowd, an obvious nervous virgin she could have her way with before he went back home.
She had been aggressive in bed, grabbing, jerking, bouncing, and speaking filthy, and Tom hadn’t had the chance to do much more than let her use his body, as if he just happened to be a support system for a cock.
There was no way he’d have that done to him again, and no way he’d do it to this sweet woman from the Spin the Bottle dating site, as gorgeous as she was.
And just what the hell was she doing here, a woman on her own, visiting a man she’d only talked online or over the phone for three months? A man she knew was anxious, cranky, and depressed most of the time? A man his coworkers and friends back home had called The Fun Killer?
He realized he hadn’t said anything, just let her stand there at the entrance to the living room in her PJs. He had fully expected to sleep on the couch again.
“Um, yeah,” he said, and hated the sound of it the second it was out of his mouth. Too detached, as if she offered him a sandwich. But a sandwich didn’t come with a cargo hold’s worth of emotional baggage. “I mean, it’s only a double, I don’t want you to be crowded…”
“We’ll manage,” she said. “Come on.”
She turned and started down the hall to the bedroom. Tom shut off the living room light and followed, his mind scared stiff, his cock just stiffening.
The bed was against the wall, and Kylie had already got in, moving so she was against it. Tom climbed in as well, not sure what to do.
But she took care of that for him, in her sweet, simple way.
She scooted closer to him, and put one leg over his. She cupped his jaw and pulled his face to hers. Then her lips, soft as cashmere, were on his. She was firm but not urgent, parting his mouth and sliding her tongue along his. She kept her hand on his jaw, and used the other to seek out his hand- he had them clenched together on his chest — and pulled it towards her, until it rested in her hair, on the back of her head.
Slowly but determinedly, she explored his mouth with her tongue, taking her time as if she was a feeling out every detail of his teeth, gums, and tongue, to memorize them.
Tom’s dick was fully hard now, and pressing against the thigh she’d draped over him. There was no avoiding it. He kissed her back, not sure what to do with his tongue, so he mirrored the movement of hers.
He’d never kissed like this, and his mind was reeling. He was still anxious — plenty of opportunity still to disappoint her — but worry was giving way to desire.
He pushed gently on her head, deepening their kiss, and she let out a small moan. It was the most beautiful sound Tom had ever heard.
They kissed like that for what felt to Tom both an eternity and an instant, once Kylie broke it off. She looked into his eyes and smiled.
“We are both wearing too many clothes,” she said. “Don’t you think?”
Tom gulped.
“Yeah, I guess we are.” Jesus Christ, he thought. So cool, so sauve.
“Then let’s fix that,” she said, and rolled on top of him so she was straddling his stomach. “Up.”
Tom sat up, and she pulled his T-shirt off him, then looked at him expectantly.
Tom was shy and anxious, but he wasn’t stupid.
He unbuttoned her pyjama shirt, revealing her plump breasts, the nipples hard. Tom realized he was staring.
“It’s OK, Tom, touch them,” she said. “I want you to.”
He did.
He traced down the outside of one breast, and then under it to her centre, and repeated the outline on the other. Then, using his palms, he ran his hands over both. He was trying to figure out his next move when she put his hands in hers, and guided them over her breasts, squeezing them by squeezing his fingers. She stopped when their hands were over her nipples, and then squeezed again.
“Just like this,” she said, removing her hands. “Squeeze them, pinch them a little.”
His dick strained against his pants as he did it, squeezing each nipple, twisting them slightly, rubbing them with his thumb.
She sighed as he did it, and Tom felt a jolt shoot from his chest to his cock. He decided this was a perfect time to show some initiative, and he leaned further and took one nipple in his mouth, circling it with his tongue, then sucking gently. Encouraged by another sigh and a hand on his head, he grazed it lightly with his teeth.
“Uhm, yes,” she whispered above his head. “Yes, that’s lovely.”
He moved back and forth between her breasts, squeezing one and rubbing the nipple while he licked and sucked the other. She smelled sweet, like vanilla ice cream.
Then she released his head, he leaned back. She was still smiling, but her eyes had taken on a sheen of lust.
“We’re still wearing too many clothes!” she giggled. She rolled off him, and then hooked her fingers into the waistband of his pants and boxers. Tom was almost too shocked to lift his hips off the bed to let her slide them down and off.
His cock sprang up once freed, and he was surprised to see pre-cum at the tip.
“Much better,” Kylie said, and took him in her grip, moving it up excruciatingly slowly until the heel of her hand was all the touched the tip, collecting the pre-cum, and using it to ease her way back down, even more slowly.
Tom groaned.
“It’s a lovely cock,” Kylie said as she started her leisurely way back up his length.
“Thanks, I work out,” was all Tom could manage in the moment. It’s not funny time, shithead, he admonished himself. He was so overwhelmed with lust and love, he needed the hard shell of humour to hide behind.
But she threw back her head and laughed, and squeezed the tip of his cock, forcing more pre-cum out.
“Mmmm,” she murmured, and tossing her hair to one side, lowered her head to lick it off. The faint, brief touch of her tongue made Tom groan again. ‘You’re funny when you want to be, Tom. Let’s have fun.”
Kylie slid her hand down to make room for her mouth, taking him in as slowly as she had stroked him, until Tom thought he would go mad. He resisted the urge to thrust, forcing all of himself in her wet, warm mouth.
Gently and casually, she sucked up and down. Tom collapsed back on the pillow as she savoured his cock. The sensation of her lips and tongue on him, mixed with the knowledge that this was Kylie, a woman he knew already he loved and would ask to marry, was quickly going to be too much, he knew. He would explode before even entering her.
“Oh my God, that’s amazing,” he said, gently lifting her head. He nearly came anyway when he saw how wet her lips were, and the shine in her eyes.
“But you’re cheating — you’ve still got clothes on!”
“So I do,” she said, and moved up his body to kiss him. “What are you going to do about it?”
He kissed her again, rolled her over onto her back, and returned his lips to hers. He couldn’t get enough.
Then he started down her jaw, her neck, to her breasts, taking each nipple in his mouth and sucking gently before kissing his way down her stomach, marvelling at the softness of her skin. He was no brute or idiot, going straight for the pussy like an animal. He’d read enough steamy sex scenes to know that just wasn’t the gentlemanly thing to do.
When he got to the waistband of her pants, he straightened and pulled them and her panties down, leaving her only in her woolly socks. He returned to her belly button, and kept moving south. Under his lips, he could feel the rise and fall of her tummy increase in frequency. He kissed down her mound, stopping short of her clit, and moving first right to kiss around her lips, her inner thighs, and then back to the centre again before repeating on the left.
Kate sighed and moaned as he travelled. He revelled in the sound of it, and in her clean, musky scent. He was grateful she didn’t rush him toward her folds, letting him explore, inhale, and enjoy her.
When he was ready — it had been years since he’d gone down on a woman — he kissed her lips before licking them, slowly, softly, as she had stroked and sucked him. She was so wet, and it made his cock throb in She gasped when he first made contact with her clit. He licked it and circled it with his tongue languidly, as if his tongue was the second hand of a clock.
She put her hands in his hair, clutching it, pushing him down with tender pressure as he licked and suckled her clit and her folds.
“God, I’m going to cum, Tom!” she gasped suddenly, taking him completely by surprise.
She is? From what I’m doing?
He sped up and applied more pressure, focusing on her clit — he paid attention when he read — and in a few moments she tightened her grips on his hair, jerked her hips, and screamed.
“Oh fuck! Yes! Yes! Keep going, Tom, keep going!”
He did keep going, trying to move with her bucking hips as her orgasm tore through her. Tom was absurdly proud, and happy he was making her happy.
After a few minutes, she released his hair and was still, still breathing heavily.
When Tom looked up, and she was smiling down at him.
“That was amazing, Tom,,” she said. “You must be a pussy-eating expert, and didn’t tell me!”
Tom blushed at the word and the praise. He didn’t trust himself to not say anything stupid this time, so he just smiled.
“Now I want you to fuck me with that nice cock of yours.”
Her words sent flames to his cheeks and electricity through his dick. He sat up and started to shuffle closer to her.
“No, I want to ride you,” she said. “Get on your back. Let me sink down on you.”
He was vaguely aware she was saving him from his awkward shuffle on his knees, and what was surely to be even more awkwardness trying to line up his cock. He was so out of practice. His embarrassment was eclipsed by his excitement, though, and he quickly lay down again.
She rolled over on him, chest to chest, kissing him deeply, shocking him. Did she not mind the taste of herself? Did she like it? He barely had to time to wonder though, as he forced to concentrate on kissing her back, his tonguing sparring with hers as they both moaned softly.
Finally, when Tom was about to beg for her to sit on him, ride him, give him release and relief from the boiling cum in his balls and his aching cock, she sat up, slid her ass back, and sunk down on him.
“Oh God!” they said together. It was funny and kind of silly, but neither of them commented on it. This was their first time, and first times are always serious business.
She stared down at him, eyes wide with pleasure, her mouth open. Tom avoided eye contact at all costs, but now he was lost in those eyes. It helped that his brain didn’t have much processing capacity for his optic nerves anyway; most of it was concentrated on translating the exquisite, long-forgotten sensation of his cock being squeezed by Kylie’s warm, wet pussy.
She placed her hands on his chest, and started to ride him, once again saving Tom the anguish of deciding: to thrust or not to thrust?
He closed his eyes and concentrated on not cumming too soon. He’d been doing OK so far, definitely a C+, maybe a B-, and he didn’t want to screw it up now. Well, at least not screw it up any more than he had. Casanova or Peter North he was not.
But goddamn did it feel good, the wet friction as she bounced up and down, groaning softly with each motion. He didn’t know why she liked him, why she had flown five hours to visit him, or why she wanted to fuck him.
But she did, and he had known long before tonight that he was in love with her.
He groaned softly, and that was all he would allow to escape his lips. He didn’t want to sound pathetic or cheesy, like the guys in porn, their exaggerated and over the top dirty talk, their theatrical moans and grunts. He knew Kylie might take this to mean he wasn’t into it, but he couldn’t bring himself to voice his pleasure.
And God, it was pleasurable, her slick cunt milking his cock, her effort making him feel desired, sexy, and sexual in the first time since forever.
He compensated by reaching up to squeeze her heavy breasts, circling the nipples with his thumbs.
“Mmmmm,” she panted. “Fuck, Tom, that feels so good!”
He fought back the goofy grin he could feel coming, the expression he knew disfigured his face when he was ridiculously proud of something, and when he knew it was ridiculous.
He also knew he had to say something now.
“God, you’re so great!” he said, and kicked himself mentally. He tried again.
“You feel so good!”
Better, but not A+ material. But he couldn’t think of anything else as he felt his orgasm coming. Was it too soon?
For the final time, Kylie rescued him, throwing her head back and steadying herself with her hands on his chest as she came.
“God!” she yelled. “Oh my God yes, fuck!”
That pushed him over the edge too, and he bucked his hips as he came, as if to force his cum as deep as he could. He couldn’t help but let a grunt escape as he gripped her hips hard.
When he opened his eyes a few moments later, she was smiling down at him, and she looked satisfied, like the cat that got the cream.
She lay down on his chest, as his cock softened inside her.
“That was so great, Tom,” she breathed into his ear.
“You were great,” he said, rubbing her back.
They lay like that for several minutes, and Tom thought he had never been so happy. A beautiful woman with a beautiful spirit was lying against him, still connected by their sex.
He knew then a few things: that she accepted him for who he was, the most intimate, fulfilling bit of knowledge he’d ever had; that he would, at some point, ask her to marry him; and that he was going to have to work on his sex game.
Get it up to a B+ at the very least. She deserved nothing less.
And maybe more real dishes. And new furniture. And make sure he got promoted at work. And-
“I have to pee and find my pyjamas,” Kylie said, rolling off him and padding out the door.
This time, Tom couldn’t hold back the goofy grin as he looked up at the ceiling. He was on cloud nine. Then he got up, found her pyjamas, and stuffed them under his pillow.
She could sleep naked with him, or wrestle him for the PJs.
Either way, it would be fun.
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An Uncomplicated Entanglement appears in Good Company,a collection of intimate, emotional, and playful erotica about lovers, strangers, and the things people do to and for each other.