Twin Hearts Ch. 02

"Was that what you've always dreamed of, Paul?" She asked with a grin, "the bigwig music exec, seducing naïve pop stars, getting a nice blowie whenever?"

"What? No!" He said, startled, "what are you talking about?"

"Oh, I don't know. You hear all sorts of stories about the music biz, you know." Ashley said airily, "Poor girls getting taken advantage of, churned up by the dirty underbelly of the industry." She made a face, all big innocent eyes and jutting bottom lip, "you're...you're not using me, are you, Paul?"

"As if," he said, flushing, "I can barely keep up with you at the best of times, let alone take advantage."

"Hmmm." Ashley hummed, her grin softening, "that's true I guess."

With a happy murmur, Ashley nuzzled in against his neck, worming her arms around him. Paul put his own arm around her and lay back, feeling overwhelmed and exhausted.

It was a strange feeling to hold her. Somehow, it felt almost normal, despite everything; all the reasons why it was anything but. Not least of all, he was her manager. Don't shit where you sleep had been a maxim of his, and it was disturbing to see how easily he could succumb.

"Hey Paul." Ashley said quietly without moving her head.

"Yeah?"

"Is it my turn for a reward?"

Suddenly he was aware that she was slowly grinding her hips against him and, more than that, he could feel her cock pressing into his hip.

"Reward?" he said warily. It would be typical of her to spoil the moment by asking him to return the favour.

"We won the award. You promised."

He hadn't promised, not as such, but Ashley wasn't one to care for such trivialities. Before he could respond, she shifted slightly on top of him, bringing her face level with him. Then, she kissed him.

His heart started pounding hard in his chest immediately. A few hurried blowjobs in a back-stage dressing room was one thing, couched in excuses and evasions. A kiss was something else entirely; a whole new game Paul wasn't sure he was prepared for.

Her small mouth moved softly against his to begin with, and he found himself reciprocating automatically. He could taste the lingering flavour of champagne, melded in with strawberry lip gloss. Her hands wandered his body, one cupping his head while the other groped towards his hip.

Clearly Ashley was not to be content with relatively chaste kissing. After a few moments, he felt her tongue dart out, then start probing aggressively at his own. He was taken aback, but it felt good too, and his fuddled mind could do nothing but acquiesce to her silent demands.

As her tongue battled his own into submission he could feel her grinding against him with more force. He could feel her trapping her huge cock between their bodies, squeezing the thick length, at one point rolling it over his own half hardening dick. He gasped into the kiss as she did so; the feeling of being squashed beneath her bigger member sending trills of pleasure through his still tender body.

"I'm so fucking hard right now." Ashley murmured, briefly breaking their kiss. She hardly needed to tell him that and, as if to emphasise the point, she mashed her cock against his once again. Paul let out a groan, and she grinned wickedly, "You like that? You like it when I bully your dick with my big... fat... cock?"

Before he could answer she was kissing him again, devouring him with her lust. Feeling a little crazy, Paul kissed back, hard.

They stayed locked together for a time, kissing and grinding, before finally Ashley broke away, both of them gasping for air. Ashley pushed herself up to kneel between his legs, and finally he could see her erection angrily tenting the pretty dress she had been wearing all night.

As he stared, Ashley reached down and hitched up her dress. For a second it snagged, then her dick fell free, flopping down from where it had been clamped against her pale belly, bouncing rigidly before settling almost perpendicular to her body.

"Wow..." he murmured, eyes fixed on the almost hypnotic bob and sway of her cock. Realising he had spoken allowed, he glanced up to find her grinning wickedly at him.

"Like what you see?" she said, her voice dripping with temptation.

Scooting forward slightly, she lowered her hips to bring her cock butting down on top of his, taking them together in both hands. For the first time he got a true view of how lopsided that particular contest was; she had a couple of inches on him, at least, and was significantly thicker.

By all rights, he ought to feel embarrassed, or even humiliated. Here was a crossdresser, an eighteen-year-old boy who spent all his life dressed as a girl, acting like a girl, living as a girl, yet far more of a man than he in such a fundamental way. Yet, somehow, he didn't. It was just part of Ashley.

"Ah!" he gasped, as she stroked their dicks together.

"You like?" She asked, this time pumping her hips so that her cock dragged along his, constrained by her grip.

He couldn't answer her questions. Each time she probed, and what could he say? Yes, he liked it? He liked it when she crushed his cock with hers, when she ground against him? Did he?

Ashley released her grip again, leaning off to the side for a moment, before returning to kneel over him.

"Hey Paul," she said softly, "you know you look really sexy like that."

"Wha...?" He mumbled, "I...what do you mean?"

"It's like..." he noticed a squelching sound, and glanced down to see her hand gliding up and down her heavy cock, "like you're waiting for me."

"What do you mean?" He asked again, warily.

Ashley grinned, shuffling forward slightly on her knees, pushing his legs even further apart.

"I think you know," she whispered.

Suddenly he felt her fingers probing as his ass, cold and slick with some sort of liquid.

"What the fuck?" he said, alarmed.

"It's okay," she said quietly, "just lie back."

"What are you doing?"

"You know what I'm doing," she replied, "relax."

Relaxing was the last thing he felt like doing in that moment. He could see clearly now, the slick shine of the lube coating her cock, the weird feeling as her fingers ran down his ass crack. She was...she was planning to...

"I'm going to make you feel so good, Paul, just you wait." Ashley murmured.

"N-no, Ashley," he stammered, "this...this isn't what...I..."

"Sure it is, Paul." Ashley said, still focused on her task, "you came back to the hotel room of a guy whose cock you've been sucking for months."

"I...but..."

"Don't worry, Paul." She said, "It's only us here, you don't need to hide anything from me."

"I'm not gay!" he blurted.

Ashley smiled, looking up from his ass.

"And I thought music industry guys were supposed to be adventurous," she said, her tone taking on the cutesy, bratty quality she sometimes used, "I won't tell if you don't."

Seemingly satisfied, Ashley edged forward again, and this time he felt it. Her thick cock head bumped against his ass cheeks, parting them slightly.

She gave him a reassuring smile.

"I'll be gentle with you, don't worry. Just try to relax."

"I...I can't, Ashley."

"Sure you can," she lowered a hand to her cock, guiding in now. He could feel the slick thickness between his cheeks, probing towards his very core, "just you wait. This is going to be just as much a reward for you as it is for me."

It would be so easy to stop it all. At any point he could sit up, push her away, tell her to knock it off. He was almost twice her size, ten years older, a fit and in shape man. Everything about the situation was wrong, it wasn't just that Ashley was a boy, but to have their positions so fundamentally reversed...

But he didn't stop it. The spell Ashley had over him somehow extended even this far, despite the voices in his head demanding he run for the hills. He'd never considered it before, like most things Ashley dragged him into, but here in this anonymous hotel room, with her beautiful face gazing down at him, there was a spark of curiosity that had no right to exist.

Seemingly happy with his compliance, Ashley eased her hips forward, and he felt real pressure against him. At the same time, she reached out with the hand not guiding her cock, gently running her soft fingers down his cheek.

"Remember to relax Paul," she said softly, "it's going to hurt at first, but it won't last long."

With a faint squeak of effort, Ashley jolted forward slightly, and he felt her enter him for the first time.

"Shit!" He gasped, clawing at the bed. His ass had given way grudgingly to her pressure, and the pain flared immediately - a harsh, stinging throb from his asshole, "It hurts Ash...fuck, take it out, take it out!"

Ashley continued to stroke his cheek, making soothing sounds, her other hand now dancing along his side. Her touch was reassuring, but nothing compared to the pain in his rear.

"I'm sorry Paul, I know it stings, it can't be helped with my size." Ashley said gently, "Just hold on for me baby."

Staring up at her soft eyes, he knew it had to be true. So he took long, even breaths, bunching and releasing his hands in the sheets while trying to concentrate on the tingling lines her fingers drew across his skin.

Just as she said, the pain started to ebb before long, draining out of him as he forced himself to relax, and his ass grew accustomed to the oversized blockage. Ashley watched him intently, her smile widening as she saw him start to ease.

"Better now?" She asked, hands still dancing across his body.

"It's...less painful..." he mumbled.

"Great!" Ashley said cheerfully, "You're doing really well, Paul! Now I'll just give you a bit more..."

While the feeling of her first thrust had largely been masked by pain, it was as though he could feel every inch as she pressed deeper. A strange fullness overcame him, somewhat akin to needing to use the toilet, but with a sense of movement as she fed him more and more of her cock. The pain returned, although not with such intensity, and was joined by twinge of pleasure as her heavy member nudged past something deep within him.

"It feels...full." He groaned.

"Mhmm, and so tight too." Ashley said happily, "I'm nearly all in, oh, you're doing so well. You ass is delicious."

Through all the strain and bizarre mixture of sensations churning within in, Paul strove to maintain eye contact with Ashley. Whatever else was happening, her beautiful face, her bright blue eyes, her warm, calming expression could get him through it.

Finally, he felt her bottom out, her hips coming to rest up against his, her balls nestling up against his ass. Ashley took a long, deep breath and Paul matched her, but for different reasons.

"You've taken it all, Paul." Ashley said quietly, "All of my big fat dick in your tiny little butt."

"Ashley...it's...too much."

Leaning forward, and somehow digging her cock in even deeper, Ashley caught his head in her hands, drawing him forward slightly into a kiss. For a moment he was completely enveloped by her; her huge cock stretching and boring into him while her enthusiastic kisses overwhelmed him in a different way.

As she kissed him, she started rocking her hips against him too. Each small thrust seemed to reach that little bit deeper, pushing further into him and evoking a strange throb far inside. Simultaneously, every movement stoked the embers of pleasure that were building below the base of his cock.

For a time she seemed content just to kiss and grind herself into him, and Paul was in no place to protest. Eventually she pulled back, just an inch or two, to meet his eyes.

"I'm going to fuck you now, Paul." The gentleness in her eyes had given way to something more primal, a smouldering heat that sent a shiver down his spine. She wanted him. Badly.

"Ashley..." was all he could manage, be it assent or otherwise.

"That's it, I want to hear you say my name, Paul." Drawing back into a kneeling position, Ashley placed her hands on his hips, fingers flexing, "I want to fuck all the sweetest moans out of you."

Before he could respond, she drew her hips back in a slow, even motion. The alien feeling of such a large object moving inside him left him breathless, and his body tingled as she squeezed against him. He stared agape as inch by inch her thick cock re-emerged between his legs.

Then she thrust into him again.

"Aaaagh!" he cried as his body exploded with sensation. The pain, the fullness, the pulsing throb her cock invoked was too much to handle.

"I wonder how thin the walls are here?" Ashley said in an almost conversational tone, "Could make for some fun rumours."

"W-what?" he managed blearily, stifling another gasp as she thrust into him again, "We...I..."

"I mean, I don't mind if people know I'm banging you, but it might not be best for the group." She continued, "All those boys fantasising that I'll fuck them instead."

"I...don't think...that's quite what they have in - ah! - mind."

"You'd be surprised." Ashley grinned wickedly.

Building up into a rhythm, she fucked him with long, even strokes, and the sound of bodies clapping together mixed in with his pants and her satisfied sighs created an erotic background noise. Anxious, he tried to keep his voice down, acutely aware of not only the volume, but the very idea that she could be forcing such girlish moans from him with her dick. The cocktail of sensations within him had already tilted firmly towards a rising tide of pleasure with each stroke, and even in his compromised state he was astonished at how quickly he had become accustomed to the act.

"Mhmmm, that's it, moan for me Paul." Ashley's face was flushed and more than a little wild, and in the moment even more beautiful than ever, "I want to hear it."

"Fuuuuck," he groaned.

"That's it, baby, show me you want it." Taking one hand off his hip, Ashley tapped his cock with the flat of her palm. Pleasure thrummed through his body again, and for the first time he realised he was fully hard once more, "Your little man is enjoying it. I think I've found your butt button, haven't I?"

Paul had no idea what she had found inside him, but whatever it was meant he could only gasp incoherently in response. Something was building inside him with each of her forceful thrusts, and he could barely keep enough control to keep his voice down.

One, two. One, two. His dick twitched with each pump of her hips, his ass quailed and clenched, the breath was driven from his lungs. One two. One two. He clawed with futile desperation at the bed sheets, his toes curled into the mattress. And Ashley kept fucking him, eyes fixed on his, her slender figure suddenly an indomitable object of power in his life.

"Oh god, it's so good inside you, Paul." She said, her own voice starting to cloud with lust an exertion too, "Virgin ass is just the best."

For the next few minutes Ashley alternated between periods of rapid fucking, gripping tightly to his hips as she drove into him, followed by relative calm. When she was truly pounding him it was all Paul could to keep from crying out with all his might, and her own gasps and moans became a little more frantic. He felt like she was drawing him on, within a whisker of boiling point, before easing off and leaving him squirming on the edge.

Between times her hands would roam, stroking and fondling at his body. She leant forward to kiss him again, squeezing his rock-hard erection between their bodies, gently rocking her own hips against him as she did so.

After the third such cycle Ashley started building up her rhythm once again, her heavy balls slapping against him with each beat. He wasn't sure he could last another round; his cock throbbed agonisingly, desperate for release through no other stimulus than that of her fucking. The ever-escalating sensations inside him already felt beyond breaking point; far beyond anything he had ever felt before.

"Are you ready, Paul?" Ashley said breathily.

He stared up into her beautiful blue eyes, his tongue stumbling on a response. Yes? No? Could he ever be ready for her?

"I'm going to cum," she continued, "I'm gonna fill your sweet little butthole with all my milk. You're gonna be all mine, Paul."

Something futile and far away in his mind protested. This wasn't how it could be. He couldn't be Ashley's. She couldn't cum inside him. That was...surely too far, too much.

But a bigger, wilder part of him wanted more, to see where the wave would carry him. He gasped and squirmed beneath the fire Ashley had lit within him, and only she could take him to end the ride.

"I want..." Ashley let out a tired gasp as she drove into him, "I want you to...to cum with me, Paul. Let's... together."

One, two. Each thrust of her hips, this perfect pretty singer, award winner and rising star, pushed him closer to that edge he could not see. This slender, beautiful creature who filled his vision, and her massive cock that flooded his senses.

"Ah!" she gasped, "It's...ah-ah-ah-ooooh..."

Taking one hand from his hip, Ashley ran a single languid finger along his cock even as her own started to twitch within him. Somehow, that small touch was the final trigger, and his rolling orgasm finally burst into a crescendo.

"Aaaaa..." his gasp trailed away to a silent exhalation as the waves of pleasure cascaded through his body. Deep inside he could feel an explosion of warmth as her pulsating cock spewed out its own load. Shot after shot of her hot cream, filling him up like a toy designed only for her pleasure, each throb of her huge cock heralded another thick spurt.

His orgasm seemed to last an age, his dick jerking and twitching as it deposited his own cum across his chest. Keeping his bleary attention fixed firmly on Ashley's, he smiled weakly as he saw the same waves of delight and satisfaction in her eyes too.

As he slowly descended from his high, his body suddenly tingling with post coital tenderness, the sounds if their mutual panting came into focus. He was tired, having done little more than lie back and take what Ashley gave. She looked suddenly weary too - exhilarated and happy, but weary.

It was hardly a surprise, with the fucking she had just given him.

"Looks like someone enjoyed himself." Ashley grinned, running a finger across his chest, scooping up a blob of semen.

Paul scowled, feeling his face flush despite everything.

With a giggle, Ashley slowly withdrew from his ass, her long dick making a squelching sound as it pulled free of his abused hole. He could see she was still half hard, her cock slick with a mixture of lube and cum.

Suddenly empty, Paul couldn't help but feel a little exposed. His ass felt like it was still opened wide, and already he could feel her warm juice starting to dribble out from inside him.

"Yay, a sexy creampie." Ashley laughed, before flopping down on the bed next to him, quickly burrowing into his side.

"I think...it's going to make a mess."

"Pah, it's a hotel. They'll be used to cum on the sheets."

For a few quiet moments Ashley seemed content to lie there, snuggling into the crook of his neck, one hand playing out an idle tune of taps on his stomach. For his part, Paul stared at the ceiling trying desperately not to consider what had just happened.

"You know..." Ashley said quietly, "you really seemed into that."

"What?"

"You're, like, a natural," she replied, "guys usually have more trouble with my size."

"Great, whoopee-do." He grunted.

"Hey, it's good!" she said earnestly, "I bet I can make you cum hands free next time."

"There won't..."

"Oh don't be silly, Paul." She propped herself up on an elbow and pouted, "It's just me and you here. You loved it, just like you loved sucking me off. So let's not pretend between us, okay?"

Paul glowered at her, but couldn't think of a response. Huffing, he turned his attention back to matte white blandness of the ceiling.