Going in (Darien pt 15)

Andrew had heard what Emily said. Heard the seductive croon in her voice, the near desperate sounding plea for him to do… what she wanted him to do.

But could he really do it?

Standing there staring at her butthole, her cheeks held apart by those red lacquered nails, he wanted to do what she asked. His cock wanted it too.

He’d just never done it before.

“Take your time,” Emily said, as if she was inside his head. “If you need some lubrication, spit in your hand. It’ll help.” She turned her head slightly to address him again. “Don’t worry about it too much though. I’m tight… but not that tight.”

She shifted her position, her butt moving appealingly as she did.

Andrew hawked up as much phlegm as he could, especially considering how dry his mouth felt, and spat into his right hand. He took another tentative step forward, close enough now that he could touch her – in places that she hadn’t allowed him to touch before.

Carefully he reached out and placed one hand on her ass. He squeezed it, and she giggled. “Go ahead baby. Play with it. Give it a good squeeze.”

Andrew did just that, delighting at the feel of her ass, which seemed very pliant.

“Do you want to give me a little slap, Andrew? Hmm? Would you like that?”

He was shocked. “I don’t want to hurt you.”

She nodded and laughed. “Don’t worry. If you don’t want to give my ass any more attention though… why not get that dick of yours in me, hmm?” She gave a little moan, anticipating his next move.

Slathering the head of his cock with his own spit, Andrew took hold of the tip and guided it directly to her asshole. It looked like his cock would never fit inside.

Then she said “Hold still, lover,” and backed up, her asshole seeming to open and engulf his cock – or perhaps it was penetrated by his erection, he couldn’t be sure.

All he knew was that suddenly his cock was being held tightly by a woman’s asshole, and that it felt absolutely amazing.

“Oh my god!” he exclaimed. “Jesus – fuck!”

She laughed, a knowing, throaty sound. “Doesn’t it feel good?” Moving her feet slightly, she bent her knees, bouncing a little, heightening his pleasure. “Some women are all about the cunt, but me… I prefer to get fucked from behind whenever possible.” She laughed again, as if she was in on a joke Andrew couldn’t know.

Something made Andrew’s hand come down, some buried instinct that had been awakened by her. He slapped on the meat of her ass, making her squeal in delight. “Ooh, Andrew, you’re definitely getting warmed up! Now, give me a really good thrust.”

Andrew pulled back, glancing down to see his cock glistening as it slid out of her ass – then pushed back in, feeling her yield in response and finally groan in pleasure.

“That’s it,” she purred. “That’s just what I wanted, Andrew… oh yes, you’re doing so well. Your cock is so fucking hard for me, isn’t it?” Andrew could only nod in response. “It feels so fucking good, trust me. Now give me another thrust, baby. Grab my hips, really give it to me hard!”

Andrew did as he was told, grabbing onto her, feeling himself slide out – then pushed back in, harder than before. As he kept doing it her asshole seemed to become looser, more accommodating as she kept talking to him.

“That’s it, that’s right baby,” she said, “keep sliding that cock in and out, keep fucking me, yeah that’s it, that’s it, get in a rhythm for me!”

Andrew did just that, hands gripping her harder, his thighs beginning to slap against her ass, his balls feeling air pass over them as he moved.

“Oh my god Andrew, oh my god, yes!” she screamed. “Are you sure this is your first time? It feels like you know what you’re doing, fuck yes it does, that’s it, keep going…”

Andrew wasn’t that conscious of what he was doing now, he was just thrusting and thrusting, feeling his cock slide in and out, slapping her occasionally, barely aware she was laughing and bouncing on his cock. He felt incredible, powerful, a real man, like he’d conquered this woman and she would do anything for him.

“Fuck oh FUCK Andrew – are you going to cum baby? I feel like you might be ready to cum – fuck yes, yes – and you can cum in my ass baby, I want you to cum in my ass, I want to feel your hot cum in my fucking tight hole…!”

Barely hearing her voice, Andrew kept pumping, kept thrusting, feeling his dick slide in and out of her so easily now. He wondered for a second what her pussy might feel like, whether it would be this tight, this yielding, but he didn’t care because she was somehow squeezing his cock, her ass muscles doing something to make his dick feel like it was going to burst.

An undeniable sensation began to grow in him, every muscle in his body beginning to tense. It was going to happen, he was going to cum inside this woman, this hot, sexy as fuck woman who’d walked into his life, who’d seduced him with this clothing, he knew that now. It might never get better than this, but that didn’t matter, he was going to fucking cum and that was all he cared about.

“Andrew, oh, Andrew,” Emily yelled. “Fuck me now baby, give me that big dick in my ass!”

Letting out a yell that would have gotten him fired on any other day, Andrew exploded into the mystery woman’s ass, feeling the hot, wet and sticky sensation of his cum gushing into her just as she’d begged him for. He didn’t stop, just kept thrusting, feeling his cum back up and drip over his cock and balls, an apparent waterfall from her ass.

Finally, he slowed, the energy of youth ultimately failing him. There was a ringing in his ears; he felt light-headed, as if he might topple over. He barely registered the sound of Emily laughing gently, or that she’d straightened up, letting Andrew’s cock slide easily from her ass.

“Was it – was I okay?” he asked, suddenly concerned. “Did it hurt or anything?”

“Hurt? God no,” she said with another chuckle. She pulled up her hose and panties, then smoothed down the back of the dress, returning herself to some semblance of ‘normal’, not that Andrew would ever see her as that. “It was fantastic.” She kissed him then, another deep, sensual kiss that Andrew could barely believe. “You’re a natural, baby,” she whispered to him as she drew away. “Some girl is going to get very lucky in your future.”

She turned him around, urging him to sit. “It looks like you’re the one who needs a breather.” Leaning against the back of the dressing room door, she looked down on him slightly, a mysterious smile on her lips. “So. You enjoyed yourself I assume?”

Andrew nodded, still getting his breath back. “Did you?”

“Such a gentleman,” she said, leaning down to kiss him as a reward. “Why yes, thank you – I had a very nice time with your dick in my ass.”

Andrew felt his face flush – hearing that still seemed incredible to him. “I’m glad,” he said. “I didn’t really–”

“Know what you were doing? It’s okay, lover. You did great, especially for a first-timer. Plenty of guys get weird about ‘ass stuff’, even if it is with a woman.”

Andrew felt quite proud in that moment. “Thanks.”

The question he wanted to ask, and that she likely knew he wanted to ask, hung in the air unsaid. Would he see her again? Was that even possible?

Instead of anticipating his thoughts however, she leaned in close to him, close enough that he could smell her perfume, mixed with the tell-tale scent of sex. “I only have one criticism,” she said, with a wry smile. “You didn’t let me finish.”

Andrew’s eyes widened. For some reason he’d assumed… well, he wasn’t actually sure what he assumed. He just thought that maybe she had…?

“Don’t worry,” she said. “If you picked up anal that quick, you’ll be great at oral in no time.”

She pulled up the hem of her dress, with a smile on her face and a gleam in her eyes.