Vol.2 Ch.17 – Third Base With A Tomgirl

Chapter 17: Third Base With A Tomgirl

After their ridiculous antics Cassie decided to bring things back on track. He leaned in and kissed Elaine and they made out for a while as he pressed himself against her, feeling her cock growing hard against his thigh. Once she was all nice and ready again he broke the kiss and began kissing his way downward. He kissed along her jawline, down her throat, played with her breasts a little, and then slid down further to nip at her thighs.

“You have really smooth skin for being such a badass, you know?" he told her.

“A lot of people think it's weird but I like to be smooth and soft," she said.

“I think it's awesome," he said. “Makes me want to just keep licking and kissing every inch of you.”

“If you tease me any longer I might just take what I need from you," she threatened.

“Promise?" he asked with a smirk.

She made a sound somewhere between a growl and a groan and he decided to be merciful.

He slid even lower, back to her crotch, and placed a delicate kiss on her shaft, causing her cock to twitch. Oh, he wanted that thing. In his ass, down his throat, it didn't matter, he just wanted it. But he wasn't going to give in that quickly.

Instead he slid even lower and started gently kissing her big, full, smooth and hairless balls.

**

She threw her head back and moaned when she felt Cassie's soft lips on her balls. The only one who had played with them before had been Ophelia and she'd only done it when Elaine had been about to cum. Now, with no stimulation on her cock she had no choice but to focus on the sensation and it was driving her wild, those soft lips and that delicate tongue handling her most sensitive place. It was a sensation unlike any other, most comparable to someone delicately licking her inner labia but not quite the same.

And then his hand started pumping her shaft.

She kicked out on the bed and clasped the sheets, shame rushing to her face when she realized that she was acting like a blushing maiden, almost exactly like Alexis had acted when Elaine had first eaten her out.

But she wanted more. She needed more. But she was terrified of rushing him.

**

For such a badass she sure lets out cute moans, Cassie thought as he kept teasing Elaine.

He wanted to get her off, almost as desperately as she wanted him to, but he wanted to drag it out. Not to tease her but because he knew that the longer that he kept her teetering on the edge the more spectacular her orgasm would be. And he wanted it to be spectacular for her. He wanted to give her a reason to come back to him for more. But at the same time he couldn't drag it out for too long or she'd suffer from blue balls and that wasn't a pain he would wish on anybody.

He really wanted to give her something special but he was scared about driving her off if he got too freaky. But he could at least give her a sneak peak of things he would be willing to do for his lovers...

**

“Holy fucking shit," Elaine gasped out as she felt Cassie's lips travel lower from her balls and started kissing her taint. It felt amazing but she was terrified he'd go even lower. Not because she disliked that. Some of the best sexual experiences she'd had before the side effects had involved beautiful women rimming her. But ideally she wanted to clean herself a little more thoroughly before anyone went for that.

Thankfully Cassie kept to working her taint and even that felt heavenly, as if he was stimulating her in a way she'd never been stimulated before. If this was a hint for how prostate stimulation felt she couldn't blame Cassie for being obsessed with it.

Finally he stopped and slid back up until her cock pointed right as his mouth. His expression was reverent.

“You want me to?" he asked. She couldn't tell who was more desperate for it between the two of them. His expression was as needy as she felt.

“Yesss," she hissed.

And then his mouth descended upon her cock.

She'd thought she'd seen her cock being worshiped when Evelyn had dropped to her knees in her shower or when Alexis had sucked her off while Ophelia had watched but compared to how Cassie was blowing her the others had seemed positively reluctant.

He devoured her cock, took it deep from the start, then pulled back and swirled his tongue around the tip, then shoved it sideways so it bulged his cheek out. He took it out of his mouth and then went low so that it flopped down on top of his face. He kissed it from below, lapping at it like a dog. If tiny hearts had appeared in his pupils Elaine wouldn't have been surprised in the slightest. And all the while he did his absolute best to keep eye contact with her, giving her the most adoring expression.

“For not being interested in me for my cock you sure worship it," she said. She was still a bit upset about that.

Cassie pried himself off her just long enough to say: “I get like that when I eat pussy, too. I like to make my partner feel like they're the only person in the world when I go down on them. I can tone it down a little if it makes you uncomfortable, though.”

She cocked her eyebrow. “Don't stop on my account.”

“Thanks," he said and went back to... making her feel special, apparently.

She sure felt special with the way he was taking her cock down. She wondered if he even had a gag reflex with the way he was effortlessly stuffing his throat with it.

And good lord did it feel amazing when he did. His mouth was so small she wondered how he even fit her inside and thus everything about his mouth felt tight. Tight and slippery and getting slipperier every time he took her down his throat and dredged up more of the thick, sticky saliva from its depths. If he was half as good at eating pussy as he was at sucking dick she wished she'd gotten to know him back before her side effects.

The way he was working her was almost as arousing as the look of utter abandon on his face as he worshiped her. It wasn't just that he liked sucking cock, though. From the way he reacted to her moans and whimpers she could tell that he loved the way he was making her feel, loved knowing that she was going crazy from the way he was working her.

“If you keep this up I'm gonna cum," she ground out.

He took her cock all the way down his throat and then looked up at her, meeting her gaze with his eyes. They were watering more and more the longer he kept her massive cock in his throat and it just made his expression look more adoring. He was choosing her cock over breathing and he wanted her to know it.

When he was sure she'd gotten the message he started bobbing up and down, deepthroating himself on her cock, switching from telling her how much he wanted her to just trying to make her cum. And then he went a step further and wrapped his hands around his throat, squeezing down to make the contractions around her cock feel even tighter.

“You asked for it," Elaine groaned as she couldn't hold back any longer.

Blast after blast of cum went down Cassie's throat and down his tummy, filling him up with her warmth. After four blasts he pulled back, not because he couldn't take anymore but because he wanted some of it in his mouth, to have her flavor on his tongue and the feeling of the thick, slimy liquid in his mouth.

When she was spent he pulled back and showed her her seed in his mouth, savoring the flavor on his tongue as he did. After showing off he got a little nasty and used her cum to blow bubbles before finally swallowing everything down.

The moment he finished swallowing Elaine grabbed him and mashed their lips together, kissing him rough and hard and with lots of tongue, not minding to taste herself in his mouth.

“That was fucking amazing," she gasped out as she broke the kiss.

“Boys make the best cocksuckers," he said with a shrug and a smile.

She pulled him even closer and ground their bodies together, pressing his cock between their stomachs as she mashed her lips back against his. Soon enough she reached out and grabbed hold of his ass, squeezing and kneading his cheeks.

She wanted to thank him for what he'd done for her but she wasn't quite sure what to do. She could finger his ass, but would he allow that? She could jerk him off, maybe have him sit on her lap. That could be hot. She could even – she blushed at the thought – give him a blowjob. Except... she'd never done that before. She had a reputation to keep and if it turned out that she sucked at sucking that would be embarrassing, not to mention the very idea of sucking cock.

Even before she'd grown a cock she'd always been in charge in the bedroom. If someone had worn a strap-on it'd always been her, not her partners. So while she'd had a bit of experience with fucking even before growing a penis she had precisely zero experience sucking dick. She'd never even sucked a girl's strap-on before. The closest she'd come had been licking the juices off of a dildo that had just been in one of her partners. Did she trust Cassie enough to show him such a vulnerable side of herself?

Yes. Yes, she did.

But she didn't want to deny him what he was into, either.

So she tangled her hand in his hair and pulled, making him lean his head back to take the pressure off his scalp. She latched onto his throat, licking and sucking and biting. Finally she growled out:

“Get on your back.”

“Yes, ma'am," he said eagerly and the moment she let go of his hair he laid down on his back and, almost reflexively, pulled his legs close, as if getting ready for her to fuck him.

She had to bite her lip when she saw the way he was presenting himself for her. She leaned down and pulled his panties off, making sure not to disturb the stockings and garterbelt. Good lord but the lingerie looked amazing on him.

The moment the panties were off he pulled his legs in again, giving her a great view of his surprisingly big cock and, more importantly, his smooth, pink, cutely twitching asshole.

“Your ass is mine tonight," she told him and leaned over to her nightstand to dig for the bottle of lube.

“You sure?" he asked, sounding surprisingly insecure.

Once she'd retrieved the bottle she reached out and cupped his cheek. “Of course. Unless you don't want this?”

“I do, but I don't want you to be uncomfortable," he admitted.

“Your ass isn't the first one I've messed with," she told him, then added in a smaller voice: “But I've never done this for a boy, so if you can give me some pointers on how to find your prostate...”

He grinned. “Pretty much exactly the same way you find the g-spot.”

She raised an eyebrow.

“Don't look at me like that," he said. “I know my way around a girl's body. And it's the same technique. Palm up and curl your fingers.”

“Alright, I'll try," she said and then squeezed a glob of lube onto her fingers. “This is gonna feel cold.”

He just giggled. Yeah, he probably knew.

So without further ado she reached out and pressed her fingers to his asshole.

He let out the hiss she'd been expecting and then closed his eyes as he enjoyed her attention.

She smiled at his reaction. If she'd had any doubts that he actually enjoyed having his ass played with they evaporated as she saw the serene expression on his face.

She kept gently massaging his tight little pucker, feeling it open up little by little under her gentle touch.

“You're really good at this," he moaned out. “I was worried you'd try to force a finger in.”

“Just because it can't get wet doesn't mean you can skip foreplay," she said as she started gently prodding, no longer content to just massage with the balls of her fingers.

“Amen," he said as he started to gently rock against her fingers. “Oh fuck it's been way too long since someone touched me there.”

“Does it feel good?" she asked.

“Amazing," he said. “You sure this is okay for you?”

She dripped some more lube onto her fingers and then began to gently push her newly lubed fingers inside him. “Okay? It's so fucking hot to have you open up for me.”

“Hot enough you want to shove your cock inside me?" he teased.

“Don't tempt me," she warned. “I want to take things slow with you. Make sure we actually like each other.”

“Oh I agree," he said. “But that doesn't mean I don't also want you to lose all inhibitions and split me open.”

She chuckled as she kept working him. Finally he had loosened up enough that she could easily work two fingers in and out of his ass without encountering any resistance. When she finally had him at that point she tried out what he'd told her.

Just like when she was fingering a girl and wanted to hit her g-spot she twisted her hand until her palm faced the ceiling and started making a come-hither motion with her fingers, trying to feel out something with her fingertips. The g-spot was a bumpy, slightly rougher spot inside the otherwise slippery smooth sheath of a pussy but she had no idea what a prostate was supposed to feel like.

“A little deeper," Cassie told her and she pushed her fingers slightly deeper inside him until she was as deep as she could go.

Again she stroked the way she would if she was trying to stimulate a g-spot and finally she felt something. It wasn't rough and bumpy but it felt like a swollen, round thing, kind of like a peeled, hard-boiled egg. And as she hit it Cassie let out a pleasured moan that had her cock twitching with how sexy it was.

“Yes, right there," he whimpered. His cock was throbbing as he writhed on the bed, clutching at the pillow.

Finally she leaned forward and pressed a single, delicate kiss on his cock.

His eyes flew open and he stared at her.

“Not good?" she asked.

“Are you sure you want to do that?" he asked.

“I can't promise I'll be good at it," she admitted. “I've never done this before.”

“Oh fuck," he moaned and squeezed his eyes shut. “Please...”

She licked her lips and leaned forward. She had no idea what she was doing. She didn't know if she'd be able to please him. The best she could hope to do would be to emulate the way Evelyn, Ophelia and Alexis had done it for her. Between the fingers massaging his prostate and her mouth on his cock she hoped she'd be able to make him cum.

So she puckered her lips and pressed a kiss on his tip, savoring the whimper he let out in return. When she pulled back she licked her lips, tasting the salty flavor of his precum. She'd always found it incredibly hot when her girls did that and, to her surprise, she didn't dislike the flavor. As she enjoyed the flavor she pulled back his foreskin and then dove back for more, opening her mouth wide to take the tip in her mouth.

She might have been stereotyping but she hadn't expected Cassie to be as well-endowed as he was. If she wasn't totally off her mark he was maybe seven or eight inches, smaller than her but still well above average. For someone who explicitly preferred having his prostate stimulated over having his cock touched she hadn't expected him to be packing something most women would have been impressed with.

She wasn't exactly comparing herself to him, though. The issue wasn't her insecurity, the issue was that she found keeping her mouth locked open for so long difficult. She knew that feeling teeth during a blowjob was a huge no-no and wanted to avoid doing that to him at all costs, but it was surprisingly tough. She decided to be extra sweet to all her partners for being so amazing at it.

She swirled her tongue around the crown, feeling the bumpy texture around it, then suckled on the tip. She tried to go deep but found her gag reflex protesting once she'd taken it halfway down her throat. She pumped his shaft as she worked her tongue and enjoyed doing it. Not only was it fun to keep working him but his reactions were telling her that she was doing a good job. Although, to be fair, she wasn't sure if he was reacting more to her mouth on his cock or her finger inexorably fingering his ass.

Soon he started rolling his hips, going back and forth between forcing his hips against the finger in his ass and pushing his cock deeper into her mouth.

“You're fucking amazing, Elaine," he gasped out. “If you keep this up you're gonna make me cum.”

As she heard that she started working his ass more forcefully and swirling her tongue around the tip of his cock more insistently.

“Oh fuck," he moaned. “Last chance.”

If her mouth hadn't been so very full she would have smiled, excited that she'd actually managed to get him off. Soon after she felt the first spurt of his cum blasting into her mouth as he threw his head back and let out a squeaky groan. She swallowed the first three spurts almost on reflex, not even wondering if it was something she'd wanted to do. But given that he'd drank hers down without complaint she didn't really have any reason to hesitate. Only once the spurts came with less force did she have time to truly taste the flavor and to her surprise she didn't dislike it. It was thick and salty and maybe a little sweet.

Her stupid mind almost made her laugh when it reminded her of that quote from the Lion King: “Slimy, yet satisfying!”

She was so distracted by the thought that the final two ropes of cum almost went down her throat and she only just managed to save herself an unpleasant and embarrassing few minutes.

Cassie had squirmed adorably underneath her as he'd cum but now he begged: “Leave some for me!”

He pulled back, making his now flaccid cock slip out of her mouth and her finger out of his ass as he slid down and mashed his lips against hers, invading her mouth with his tongue and scooping out some of the cum still left in her mouth. They stirred the slimy mixture up between them until it was frothing and only then did he pull away and allow her to swallow.

“Was it okay?" she asked, insecurity bleeding into her voice. She knew her way around the bedroom but her experiences with men weren't exactly extensive.

“You were fucking amazing, Elaine," he told her. “If sex with you is any better than this you'll get me addicted.”

“I can't wait to find out," she told him and then kissed him again.