Vol.3 Ch.36 – Getting Freaky With A Tomgirl

Chapter 36: Getting Freaky With A Tomgirl

Cassie had no idea what Elaine was planning but that made it an order of magnitude more exciting. He had obediently gotten on all fours but now he was wondering what she intended to do to him. This was a position for sex but not for foreplay. Was she planning on skipping over everything and railing him immediately? That didn't seem like something Elaine would do.

His anticipation ratcheted up a few notches when he heard the rustle of clothes, presumably Elaine taking her clothes off.

“You got lube around here somewhere?” she asked him.

Who the hell do you think I am? Cassie thought, though he didn't voice it in case Elaine wouldn't get the reference. “Check the nightstand,” he said instead, leaning over to grab for it but she gave his ass a smack.

“You stay right where you are,” she told him and he went back into position.

Even from this position he could see Elaine leaning over and digging through the nightstand, letting out a wicked little sound when she noticed his collection of sex toys. As it turned out, Rachel knew a little trick for getting the base's replicator to create rather fun objects if one asked nicely. Either way, from his vantage point he saw her toned body and her large, beautiful breasts, swinging as she hunched over. God but he wanted to bury his face between them while she went to town on his ass.

“Have you been keeping this in all along?” she asked him and in response a little giggle escaped him. Apparently Elaine had finally noticed the plug in his ass.

“Yes, ma'am.”

“Been preparing for me, have you?”

“Uh-huh,” he whimpered.

“Good girl,” she purred. “Your ass is mine tonight.”

“Yes, please,” he whined, wiggling his ass at her.

He felt her hands on his ass, kneading his fleshy orbs and spreading them apart, admiring the plug. It was a particularly nice one with a jewel tip, looking like a little gem peeking out of his ass. He'd put it in right after cleaning himself thoroughly and all throughout dinner he's been sitting on it, exciting himself with the thought of Elaine yanking it out and replacing it with her enormous cock.

But instead of yanking on the plug she curled her hand in his hair and yanked back, making him lean his head back to take the pressure off.

“You want it a little nasty, don't you?” she growled into his ear.

“Yes, ma'am,” he mewled. He had no idea what she had planned but he was certain he'd love whatever it was.

And then, finally, he felt her grabbing hold of the plug. She pulled it out with agonizing slowness, holding it still so that the widest part stretched him out, and only then did she pull it out. The plug wasn't huge, wasn't the largest he owned, but it was big enough to prepare him for Elaine and so when she pulled it out he felt the cool air on his insides as his gaping ass slowly closed back up.

“Your ass looks so sexy,” she told him. “I want it so bad.”

“It's all yours,” he said, wiggling it to entice her.

“You better believe it is,” she growled then leaned over him. She showed him the plug that had just been in his ass and he was gratified to see that it was still sparkling clean. “Open up, slut.”

He swallowed. Well, he had told her he wanted it nasty, hadn't he? He opened his mouth and she put the plug in.

“It suits you, you little slut. Keep that in until I tell you otherwise.”

He whimpered and did as he was told. It was amazing, the sheer depravity of it. Still, he wondered what she would do next. She had asked for lube. Was she going to fuck him with no foreplay? It would be hot, having her fuck him while he sucked on that plug as if it was a fucking pacifier, but still. He did feel like a nasty whore right then but even so he preferred a little foreplay before a good reaming.

He heard the snap of the lube bottle but the familiar sensation of cold lube hitting his pucker didn't follow. What was Elaine playing at here?

He soon found out when she grabbed his dick, already hard from the sheer anticipation of the compromising position, and bent it backwards. Oh fuck, was she going to milk him as she fingered his prostate? That would be amazing.

But instead he felt his dick being enveloped by slick, warm, firm, satiny cushions as she wrapped her breasts around it.

Oh good Lord, he thought. It felt amazing and he couldn't stop himself from rolling his hips. The position was awkward for it but still he did his best to thrust into the softness presented to him, fucking her tits as best he could. But he still couldn't fathom the position. There were so many positions way more suited for a titjob, ones where Elaine could suck on his tip every time it surfaced from the soft embrace. So why had she...?

Cassie squealed out like a sow when he felt the soft, slick warmth of Elaine's tongue against his hole.

Oh Jesus fuck... he swore internally as he surrendered to a situation so raunchy, a pleasure so filthy, that even with his dirty, dirty mind he hadn't imagined she would go for it.

**

Cassie's ass yielded easily to Elaine's tongue, already relaxed from accommodating the plug. She hadn't started prodding at it right away, wanting to make the anticipation build as she worked his cock between her breasts and lapped at his ass. It was dirty and filthy and she'd fantasized about doing something like it since forever. It was one of those sex acts where it was hard to say who was in the more compromising position.

Cassie was bent over like a whore, being worked from both ends with a rigid tongue fucking in and out of his asshole while he sucked on the plug that had come out of his ass like it was a pacifier. Elaine on the other hand was on her knees with her face buried in her partner's ass, making out with it like it was a lover's mouth.

Either way, Elaine could feel Cassie melting under her ministrations. He had started off trying his best to thrust between her breasts but those thrusts had soon become erratic and soon after his legs had begun shaking, his whole body turning into jello as she kept doing her best to drive him wild.

She knew she could just keep going and he would lose himself in short order, squirting out his cum between her tits while she had her tongue three inches up his ass, but she also knew she could up the ante a little. She'd been squeezing her breasts together with both hands to provide the necessary tightness for Cassie's cock but now she reached around herself, doing her best to press her breasts together with one arm so that she had one hand free. That hand, slick with the lube she'd squeezed between her tits, she pressed flat against his glans and then began rubbing it like she was trying to polish it, buffing it until it would sparkle. And sparkle it did, in a very metaphorical way.

The moment she started doing it Cassie squealed again, and the sound was music to her ears. Not only did she love making him feel good, not only did she love his high, feminine voice and all the little sounds of pleasure it could produce, the way the sound was warped by the butt plug in his mouth made it so much better.

She hadn't been sure he would be up to it but the moment she'd seen how sparkly-clean that plug had been she'd known he would. And he had. And the little gem at the tip sealing his lips was the sexiest fucking thing, even if it looked a bit like a pacifier.

And as he let out this loud squeal his cock began to erupt, the cumshot so violent it produced a squirting sound that managed to drown out his squeal. The violent cum blasting down her stomach, the squeal and the obscene squirting noise made her cock twitch so hard it slammed into the bed frame from below.

Again and again he came, painting her entire belly white with pearly, sticky cream, until finally he just collapsed on the bed, his limbs no longer capable of supporting the quivering wreck of his body.

But Elaine didn't afford him any mercy. He wanted to get freaky with her and she would show him freaky. She'd lost a good chunk of her mojo when she'd grown a cock but she felt like it was finally back. She'd been a freak between the sheets before the side effects and she was finally confident enough again both in herself and in her tool to get back to that. And so instead of letting him rest she twisted her fingers in his hair and hoisted him up by the scalp, flipping him onto his back.

His face was an utter mess. The subtle little bit of makeup he'd put on had run down his face and his eyes were lidded like he was about to pass out. But despite that, despite everything, he'd managed to keep the butt plug firmly in his mouth.

I'm going to have to reward him for that later, she thought as she reached out and grabbed hold of it, pulling it out of his mouth and setting it down on the nightstand.

“What do you say, slut?” she asked him, her tone much harsher than she really felt.

“Th-thank you...” he slurred, the words melting into each other.

She smirked, then tucked a strand of hair behind one ear, pried his mouth open and then spat into it, a glob of thick, sticky saliva filling his mouth. He eagerly swallowed it and before he could take a deep breath her lips were on his, giving him a savage, demanding kiss, exploring his slack, unresponsive mouth with her tongue.

“You're so fucking gorgeous when you cum your brains out,” she told him as she broke the kiss. “Now come clean up the mess you made.” And then she yanked him towards the sticky cum drying on her tummy. She'd smeared a bit onto him when she'd kissed him but there was still more than enough left for him to lick off. And despite his exhaustion he did. With gusto.

**

Cassie wasn't really in the habit of eating his own cum. Not to say that he disliked it but usually he didn't see the point in it. It wasn't as if the flavor was particularly bad but swallowing cum was something he usually did to show his partner how into them he was. Normally that meant swallowing someone else's rather than his own. This time, however, licking up his own was a way to show Elaine how much he loved getting freaky with her and so he did the best he could, gradually recovering from having his brain fried as he slurped up more and more of the stuff.

As he licked it up he gradually worked his way downward, starting just under her breasts and slowly working his way down to her pelvis and then lower still. Some of his cum had run all the way down to her balls and she'd told him to clean up everything, hadn't she?

So he worked his way down and down, placing wet, open-mouthed kisses on her rock-hard cock and then going deeper still, lapping at her balls and then her thighs until she was finally clean again.

Along the way her breathing had started growing labored and by the time he was done cleaning her up her cock was throbbing desperately, looking almost angry it was so dark and swollen. God he wanted it. Down his throat, up his ass, rubbing over his belly. No matter how, he needed it.

He knew his ass still needed a bit of time to recover but he could tell that Elaine was growing desperate and impatient and so he placed a kiss on her tip and then leaned forward, letting the thick purple head part his lips as he took it in his mouth. He swirled his tongue around it and then pulled it out of his mouth with a “Puah!”

“Will you please fuck my mouth?” he asked. He was doing his best to sound like a desperate whore and there wasn't much acting involved in it. He needed it.

“Since you've asked so sweetly,” Elaine cooed, then her tone got firmer again. “On your back, head off the mattress.”

Fuck yes. She was going to fuck his face, rutting her giant cock into his throat. He crawled into position as she got off the bed and no sooner had he opened his mouth wide that she stuffed her cock inside.

It locked open his jaw and he did his best to swallow around her girth as it went in, trying to acclimate to the sensation of her monster filling him up. He didn't even know why he loved getting face-fucked so much, all he knew was that he did. The feeling of a cock shoving inside him, filling up his throat and locking open his jaw, the scent and flavor of cock suffusing his senses, the sensations of abrupt jerking and the heartbeat pulsing through the cock in his mouth letting him know exactly how wild he was driving the person making use of him and soon enough the sticky treat that would feel so warm being pumped directly into his tummy.

There were different kinds of face-fucking and the way Elaine did it was by far his favorite. There were those who sought their own pleasure while ignoring how he felt, there were those who were too scared of hurting him to get really into it and then there were those like Elaine. She began by reaching out and clasping one of his hands, telling him without words to squeeze if it got uncomfortable, and then she started rutting into him. She was seeking her own pleasure, using his body as a means to relieve her lust, but she was still monitoring his reactions, ready to stop at any time if he couldn't handle it.

And he loved that. It felt as if she were using him like a disposable sex toy, a hole to dump her load in, but in the end that was all just theater. She was careful not to hurt him but she made it feel as if she didn't care. It was the best of both worlds, the degradation of being used for someone else's pleasure while still having the safety net of someone who cared.

But that didn't mean he didn't still feel like a whore. She didn't stroke into his mouth. She rutted into him, shaking the bed on every thrust. On every thrust her balls smacked into his face, his nose inundated with her musk, and on every backstroke some of the sticky saliva from the back of his throat came out alongside her cock, running down his face and absolutely smearing whatever traces of makeup had been left.

He reached out and gingerly placed one hand on his throat, feeling the way Elaine's cock bulged out his throat on every thrust. His cock was rock hard but he didn't touch it. He knew right then he could make himself cum in five strokes tops but he didn't want that. He wanted to lie on the bed and take that enormous cock in his ass. He wanted her to rut into his ass the way she was rutting into his throat, wanted her to hammer that huge purple tip into his prostate over and over. Cumming the normal way right now would only diminish the sensation. And so he just lay there, taking that cock down his throat, his cock throbbing with neglected need as he waited for her to be done with his throat and go for his ass.

**

Elaine knew she was being too rough with Cassie. Apparently she hadn't quite gotten used to having this cock yet after all because the sensation of his throat had made her lose all reason. She hadn't wanted to hump his face with no regard for his well-being but it just felt too fucking good to be gentle.

Again and again she buried herself in his mouth, feeling her orgasm approaching. When she knew she wouldn't be able to hold back the tidal wave any longer she ground out: “I'm gonna cum!”

He didn't squeeze her hand, didn't try to scramble to get away, and she was so far gone she chose to take this as a sign of consent. She buried herself in his throat as far as she could go and then came, filling his belly while the rhythmic contractions of his throat milked out more and more of her sticky white cum.

More and more shot out of her cock and she could feel her balls tightening up, dumping more and more of their contents down his throat. When she was done she slowly, carefully pulled her cock out of his throat and flopped down onto the bed beside him.

“That...” she panted, “was fucking unreal.”

Cassie didn't answer right away and she was scared she'd broken him.

When she could move again she rolled onto her side to look at his face. He had a dopey smile on his face, his expression completely melted.

It took him a few more minutes to regain the ability to speak and when he did he said: “Pretty good... for foreplay.”