Vol.3 Ch.37 – All The Way With A Tomgirl

Chapter 37: All The Way With A Tomgirl

Elaine had pulled Cassie close so she could spoon with him while they both recovered but it didn't take more than two minutes before Cassie could feel her erection pressing into his ass.

“You're ready to go again?” he asked incredulously. Men had refractory periods but apparently that wasn't a problem Elaine had to deal with.

“You're just too sexy,” she told him, rolling her hips a little and pressing her length between his cheeks, spreading him open a little to nestle her cock in his buns. “But I can still wait a little if you need some more time to recover.”

Truthfully after taking that massive thing down his throat he could have used a couple more minutes but the desperate ache she'd primed in his ass was getting harder and harder to ignore, what with the hot rod of steel pulsing with the rhythm of her heartbeat between his cheeks. “I need it,” he admitted, rolling his hips against her length. He was still exhausted, yes, but he wanted her to fuck him up, to break him, so exhaustion was a good thing.

“On your back then,” she told him. “I want to see the expression on your gorgeous face when I stuff you with my cock.”

He bit his lip and rolled onto his back. He was certain it would be embarrassing to be seen with his face melted in pleasure but he also wanted to see her expression, wanted to see her eyes roll up inside her head when she felt his ass wrapped around her.

She grabbed his knees and spread them apart so she could sit down between his legs, then let her rock-hard cock flop down onto his tummy, absolutely burying his dick beneath it. Goddamn. Cassie had never had penis envy and, being well above average himself, he didn't exactly feel embarrassed by what he was packing, but the way Elaine's cock dwarfed his had him growing hard, the feeling of emasculation turning him on far more than he had expected it to.

Elaine reached for the bottle of lube and Cassie leaned forward and said: “Gimme.”

She scooted closer to hand him the bottle and he squirted out a large dollop, then used both hands to spread it over Elaine's cock, pumping it and getting himself into the right headspace to get fucked. It was something he was very good at, something he enjoyed. It was a bit paradoxical. Anal sex required the receiving partner to relax as much as possible. The clenching, the tightening of muscle, that was what made anal sex hurt for so many. That was why foreplay was so much more important for anal. The gentle massaging let the anus relax, allowing it to let larger objects in. After receiving the mother of all rimjobs Cassie was quite relaxed down there but it was still good practice to go through his routine.

And so he kept smearing Elaine's cock in lube, his lower body relaxing more and more as he fantasized about how it would feel to have this massive pole scraping his insides. It looked so good, uncut and straight as an arrow, no bend to it that he could see, the tip large and colored a deep, almost angry, purple.

“If you keep jerking me off I'll cum all over your face,” Elaine ground out.

“Don't threaten me with a good time,” Cassie teased but let go of her cock nevertheless. He didn't need a facial. He needed her to shove that thing as deep inside him as it would go and then shoot her load deeper still.

She took a couple deep breaths to center herself, then scooted back between his legs. Almost instinctively he grabbed his legs and pulled them close, folding himself over to give her better access, which she used to place the head of her cock against his waiting hole. He groaned as he felt her heat at it and then panted as he realized that he was so relaxed his ring was ready to flower open at the slightest push.

“You ready, baby?” she asked, the husky voice sending a shiver through his body.

“Mess me up,” he hold her.

And so she did. She leaned her hips forward slowly, almost tortuously so, and as she did her tip began to spread open his awaiting hole. Never before had he yielded so easily to any cock and he hadn't expected himself to take something of that size so effortlessly. She slid inside him, encountering no resistance, as if his hole had been made as a sheath to put her cock in.

As she continued pushing inside her thick crown scraped against his prostate and his eyes rolled up in the back of his head. If a single tap of his button had him reacting like this how would he handle it when she actually started laying into him?

He would soon find out because when she had finally pushed herself all the way inside him, when her balls, somehow feeling even heavier than earlier, pressed against his ass cheeks, she pulled back out until only her tip was left inside him. She gave him a moment to breathe, then mashed their lips together in a ferocious kiss and rammed her cock back inside. His mouth welcomed the intruder as eagerly as his ass did, wrapping his tongue around hers and moaning into the kiss even as his ass clenched around her cock.

He always loved being with partners who were bigger than him, loved having another's weight pressing down onto him as he was being fucked, but Elaine smothered him in a way no man had ever managed. She was taller than him, yes, and more muscular as well, but that wasn't all. Her breasts were mashed into his chest, the soft weights pressing down on him even as she mauled his mouth and savaged his ass. Every inch of his body felt like it was buried beneath Elaine and yet he could feel the muscles of her stomach rippling on top of him, her six-pack flexing pressing into his hard cock on one side and his own toned tummy from the other.

And the feeling of fullness? Oh god. She filled him up so good, spreading him open almost but not too much, going almost but not too deep. If her cock had been any longer, any girthier, there would have been a feeling of discomfort, but it wasn't and so there was only bliss from being filled and plumbed to his limits. Every thrust battered his prostate in new and exciting ways and he felt like he'd been cumming non-stop ever since she'd put it in.

Her pace had started off slow, almost cruelly so. He couldn't blame her. From the expression on her face she'd been amazed at the feeling of his insides, determined to savor every inch on every pass, but it had been torture for Cassie. But as her desire had ratcheted up she'd become less and less interested in prolonging things and had started properly fucking him, rutting into him like a breeding stud, going harder and faster with every thrust until her balls smacked into his ass so hard it qualified as a spanking.

And just as he thought she'd lost it, that she had completely surrendered to the feeling of plowing him like a living fleshlight, she leaned back, far enough to pull out of him. “Turn around,” she growled. Her sensuous, seductive tone from earlier was long gone, the haze of desire replaced by a raw need to fuck like animals, and it drove Cassie wild.

He flipped around and presented himself the way he thought she wanted, face shoved into the mattress and ass high up, no doubt looking like the most desperate whore. Elaine wasted no time in shoving herself back into him and damned if she didn't feel even bigger, even longer in this position.

But then she surprised him by snaking her arms around his waist and pulling him up, her chest pressing into his back as she held him in place. “Gonna make you cum all over this bed,” she growled into his ear as she started to fuck him with even more vigor. She felt so deep, so unbearably deep, and as he looked down he saw his tummy bulging out every time she buried herself inside him. It was one of the hottest things he'd ever seen, even more mesmerizing than the sight of his cock bouncing up and down, dripping with neglected need, as she quite literally rocked his world with every thrust.

“You're so fucking sexy,” she whispered into his ear as she placed open-mouthed kisses all around it. “I love fucking your tight little ass. Do you like the way I'm fucking you?”

“I love it so much,” he whimpered, reaching back to touch her any way he could.

“What do you love, baby? Talk to me.”

“I love your cock,” he began chanting. “I love the way you're filling me. I love the way you're spreading me open. I love the way you fuck me so hard. I love the way you bulge out my tummy. I love the way it feels when you pull back out. I love your big tits pressing into me as you fuck me. I love the way you toss me around like a sex toy. I love...” He stopped when she shoved two fingers into his open mouth and began fucking him with them. Her other hand grabbed hold of one of his nipples and started squeezing.

“Keep talking, babe,” she husked and he did his best to speak with his mouth full, her thrusting fingers slurring his words.

“I love the way you fill me up. I love the way you look at me. I love the way you're mean to me. I love the way you taste. I love the way you smell. I love the way you look. I love your cock so much. I think I'm gonna... gonna...”

**

Elaine was in a frenzy fucking Cassie. She hadn't meant to be this rough with him, to treat him like a fucking fleshlight, but he got off on it so hard she couldn't stop herself. His body was like putty to her, hers to control and hers to fuck. His hole clenched around her just right, providing the perfect amount of friction for her to fuck into, and he reacted to her fucking so nicely that she lost herself in it, bucking into him harder and faster and deeper than she probably should have gone.

Slimy liquid gathered at the tip of his dick and splattered off on every thrust and for a while now it hadn't been clear anymore. He was cumming on her cock with every thrust, her dick fucking the cum right out of him, and she knew she wanted to see him go wild, to watch him absolutely lose himself before she dumped her load into him. And so she did her best, forcing him to talk dirty to her while finger-fucking his mouth and pinching his nipple as she plowed into him and soon, when she was about to lose it, he finally gave her the signal that he was reaching his limits as well.

It came as a relief to her. She was at her very limit. She needed to cum, and quick. And so she reached down and grabbed his hips, then slammed her cock home inside his tight little hole, pulling him back so there would be no escape. When her hip bones were pressed tight into his ass cheeks she growled:

“Now cum for me you little slut.”

And then she came.

**

Spurt after spurt of hot, sticky liquid bloomed in his guts, deeper than anything had ever gone, filling him with warmth as the cock it was coming out of thrummed in his ass, practically vibrating against his prostate as it twitched and throbbed. It was too much for Cassie to bear and he came, painting line after line of sticky white cum over his bedsheets as his ears rang with white noise.

His legs buckled but there was nowhere for him to drop, nowhere to escape to. He was impaled, propped up on the massive cock that had fucked the orgasm out of him and held there by two impossibly strong hands.

He thought he'd been fucked before, that he'd enjoyed the savage fuckings he'd received prior to this but there was no comparison between what he had experienced before and what Elaine had just done to him. He'd never cum this hard, he'd never been stuffed so full, he'd never had filthy, degrading dirty talk that had left him feeling this good about himself and he'd most certainly never enjoyed foreplay that raunchy and that good. Ever other time he'd had sex paled in comparison to doing it with Elaine. He was an addict and his drug was currently buried to the hilt in his ass.

And then it pulled out, inch after inch being dragged out of his guts, and when the head pulled out of his stretched hole he could have sworn he heard the sound of a cork being pulled out of a wine bottle because a moment later what felt like a gallon of creamy white cum drained from his ass, utterly soaking his bedsheets.

Without Elaine having to say anything he turned around, flopped onto his belly, being careful to avoid the puddle of cum, and began cleaning up Elaine's cock with his mouth, licking and lapping and sucking the cum off it.

There was nothing filthy about it, he'd been very thorough about his preparations after all, but the act of worshiping the cock that had just been in his ass was still dirty, still degenerate, but for Elaine he would be the biggest pervert she wanted him to be.