Two Toms and a Brain Cell Ch. 02

Casey found himself thinking back on his date with Ash days after the fact, even as he returned to work. Questions of when he should start talking with her again and when they would see each other next lingered like a thorn in his brain. He often considered texting her again, but he always felt awkward about it. He was never the best at initiating conversations.

As he went through the motions of his shift later that week, keeping stock and reshelving items in the store, he found himself checking his phone more impulsively than usual. He kept wondering when she would text again, perhaps asking about another date or to simply start another text conversation. The silence, combined with his struggle to think of something to say, only added to his anxious feelings.

He was absentmindedly stocking cans of soup when he heard two people step up behind him, their shadows looming over him. At first he thought it was customers come to ask him a question, but then he heard a familiar voice.

"Guess who?" The deepness and roughness of her voice was undeniable.

He swung around to see his new girlfriend standing behind him, along with a girl he recognized from her dating profile. It was Astrid, a close friend of hers. A rather heavyset woman, she sported a shaved head and varied piercings. They both wore leather jackets and jeans, looking like they were part of an all-girls biker gang.

"What are you two doing here?" He asked.

"Well, we were on our way back from work and needed to pick up a few things here. Thought I might as well say hi. Plus, I don't think you and Astrid ever met."

Astrid raised a hand. "Yo, she told me all about you." Sticking her hands in her pockets, she looked at him rather intently. "I prefer girls, but I can see why you like him. Seems cute."

"Hell yeah he is!" She ruffled his hair.

Though it was a little embarrassing to have her do that in a public space, he always liked having someone play with his hair.

Astrid smirked. "Oh, he looks soft. Can I?"

He shifted his gaze to the side to avoid eye contact "...sure."

"Bitchin" she then joined the boy petting session.

"Look at you, getting head pats from another woman." Ash observed, crossing her arms. "Head pat slut."

"Yeah..." he smiled as he felt her fingers rub his scalp. Then, coming to his senses and recalling he was still at work, signaled her to stop. "That's enough. I can't socialize too much while I'm on shift, the boss always gets onto us for that." He turned around and went back to stocking. "But uh, how've you two been?"

"Doing good," Ash responded, "but I've been meaning to ask: the idea of going on another date was thrown out last time so...would you like to do that?"

"I was actually going to ask you a similar question, I'd love to go out again."

"Awesome! Just tell me your days off and we'll work something out!" She slapped him on the back, almost making him fall forward in the process. "Anyway, I can't get home too late, got a few things to take care of. We can talk later."

"Okay!" He glanced back and waved bye as the two left.

Shortly after he got home from his shift, he got a text from her and they began the back-and-forth on scheduling. Fortunately, she would be available on his next day off, and as for location, they eventually settled on him simply coming over to her house to hang out and watch tv (and perhaps do some other fun things while he was there).

When the day finally came, he could hardly wait. He arrived at the scheduled time, and shortly after they settled on ordering a pizza for dinner. Once it arrived, they started their little marathon. Between the two of them, they were able to demolish the box in short order.

One pizza and several episodes in, Ash was getting pretty horny. She'd put fucking him again on the agenda, and at that point she didn't feel like waiting much longer. The only question was whether he was down for it or not. She looked at him and asked him in the most subtle fashion she could think of.

"You want me to peg you?"

Casey nearly spat out his root beer "I'm sorry?!" He exclaimed.

"It's a simple yes or no question."

"Yes, but you're really just gonna ask that out of the blue?! Lead into it at least, geez! You need foreplay, romance, and seduction!" Crossing his arms and looking away, he huffed. "This is not how you speak to a princess!"

"Yeah, I do kinda suck at that. I was gonna beat around the bush, but I didn't know what to say so I just blurted it out." She scratched the back of her head awkwardly. "Uh...lemme think...you know that thing we discussed over text?"

"Well don't lead into it now, you've ruined the moment!"

"Ugh, fine. If I can't find the right words, then maybe my actions will get you in the mood. Mind if I...?" Leaning in, she tucked strands of hair behind his ears as she looked directly into his eyes.

He sighed. "You may..."

She kissed him, running her hand along his nut-brown locks. Her free hand ran down his back, before gently holding his hips.

He arched his back and grunted softly, feeling her tongue stick itself into his mouth.

She pulled out of the kiss briefly. "Now are you getting in the mood?"

"Almost." Frankly he was already getting a little frisky because of how handsy she was being, but he wanted to play coy just so they could keep making out.

"I'll change that before long."

She grabbed him by the shoulders, and with a gentle push, he fell back on the couch cushions. Getting on top, she pinned him down. His heart started to beat faster, and it only beat harder when she pressed down on him and started kissing him again. Arms rendered useless, and laying under her full weight, all he could do was melt into her kisses. Although it was off to a rough start, he was definitely getting in the mood. What she lacked in words, she was making up for in actions.

After several minutes of that, she pulled out of the kiss. "I think you're ready now."

"How can you tell?"

"I can feel you getting hard." Looking down, she groped his bulge. "This guy is pretty eager."

"Yes, I'd say I'm in the mood now."

"Good! Now let me go get my strap!"

Getting off him, she disappeared into her bedroom. After a minute or two, she reemerged with a cardboard box.

"Recently I had an idea." She explained, as she set the box on the floor. "I fucked your huge dick last time, so I'm thinking I should give back the inches. So, shall I peg you with one of my biggest?" Saying that, she pulled out a thick, 9-inch dildo.

"I'm definitely down. I play with a lot of dildos at home, so I can take that."

"Well, just to be on the safe side..." she put on a latex glove. Pulling back on it, she let go of it and made a loud snapping noise "I think I ought to stretch you out and make sure you're ready."

"Probably a good idea." With that, he started stripping down. He slid down his long skirt and underwear, along with his black sweater. After that, he got on his hands and knees.

She got behind him and, observing her new boyfriend's butt, smiled. "Now that I'm looking at it from this angle, I'm not sure I realized how fat your ass was the other night. Then again, your thighs and cock are both fat too so I guess it makes sense."

Glancing back, he chuckled and shook his ass, making it jiggle. "I'm the whole package baby~"

"I'm a real lucky gal, huh?" She firmly grasped his cheeks, feeling her fingers sink into it. She then spread them out, and immediately it became clear that he wasn't lying about playing with dildos regularly. It seemed she wouldn't have to stretch him that much after all. "Time to get you ready."

Lubricating her glove, she started fingering him. Sticking two pointed fingers into his ass, she wiggled them around and spread them out. She could hear him grunting and softly sighing in response to her movements, and she noticed his dick kept twitching and getting bigger. This only made her more excited to peg him, and fortunately for her, it didn't take long before he was ready.

She stripped down herself before securing the strap-on to her waist. "Wait, how could I forget?" She went back to the cardboard box on the floor, sifting through it for a moment before pulling out a pair of cat ears. "Do you mind wearing these?"

"T-those?!" He could feel himself blushing at the sight. "Uh...I suppose I don't mind..."

"That face was all the confirmation I needed." She smiled then handed him the headwear.

He grumbled something under his breath, embarrassed that he'd accidentally exposed another one of his kinks. After putting them on, he saw her eyes light up before him.

"You look so fucking cute in those!" She cried. "I always thought it was a tragedy that catboys don't exist, but" leaning down, she cupped his face and licked her lips "I think you might just be prettier than any of them. Can you say 'nya'?"

He stuttered, feeling humiliated yet turned on at the same time. Making a cat pawing gesture, he let out a "Nyaa~"

She put a hand to her chest and tightly shut her eyes. "Fucking...you're so goddamn cute! I can't take it anymore, I gotta wreck your ass right now! Turn around!"

"If you say so, master."

"Oh, gonna lean into the roleplay now?" She started preparing her strap with a hefty dose of lubrication. "You weren't lying about being kinky, huh?"

"I'm not usually one to exaggerate." He looked back at her, observing as she gave the dildo a good coverage.

Once it was properly lubricated, she looked down and grabbed his ass again before spreading him out even more.

"I'm gonna put it in now. Ready?"

"More ready than ever."

"Good." She slapped the dildo on his backside, before pulling back and gently putting it inside. The dildo pushed his hole apart as it slowly moved deeper. Although he'd been prepared, she was sure not to go too deep all at once. Moving her hips back and forth, she thrusted it only partway in.

Her strap was so thick, he felt his insides clinging to it. She wasn't going too hard yet, but she was hitting his prostate just right. Gradually he could feel it pushing in deeper as his ass adjusted to its size. He knew that getting fucked by someone else felt different than masturbating with a dildo, but this was certainly a good reminder.

Once he was ready, she let him have it. Pushing the strap in until her crotch was pressed against his fat ass, he let out a soft moan. It felt like it was grinding all the way into his stomach, reaching the limit of how much he could take.

Once he could take it all in, she leaned over and whispered in his ear. "You did it, you took every inch." Tenderly, she placed her hand on his shoulder. "I'm going to started doing you harder now. Are you ready?"

Breathing heavily, his whole body felt hot. Touching and speaking to him so tenderly, her hot breath against him, and feeling her strap; it was enough to drive him crazy. He wondered if he should've been grateful that she couldn't see the desperate face he was making. "Yes, master."

"Good kitten." Raising her body back up, she grasped him by the hips and started moving her hips more intensely. Each time she thrusted against him, her body collided with his ass, making it clap. That, combined with his moaning, only made her want to peg him even harder.

"You're moaning like a man whore." She dragged her nails along his back, leaving scratch marks. "Does it really turn you on that much to get nailed by my strap?"

"Yes! It feels really good, master!" He cried.

"Kinky slut." She gathered his long, nutbrown hair behind him before pulling on it. His head was forced back and he let out a desperate moan. "Fine. I'll rough you up good and leave you a cumming mess. This hole is mine now, got it?"

"Yes, it's all yours!" It was all almost too much. His prostate was being pounded relentlessly, and now she was treating him roughly while saying such degrading things to him.

"Not just your hole, but your cock and your mouth. This entire body belongs to me. From now on, you'll be my special little bitch boy."

"Yes, I understand perfectly! Use and abuse me as you wish!"

"Now say 'thank you master'. I have awarded you this special privilege of personal bitch boy, after all."

"Thank you master..." losing himself in the pleasure, he was really letting his submissive side show. Though perhaps it would be more accurate to say that she was pulling it out of him, since her words only encouraged him to slip deeper into a sub space.

She spanked him, making his cheeks bounce. "That's a good little slut." Admittedly she was further testing the waters with that kind of talk, but it seemed he was way more of a masochist that she'd initially realized. Now that it was clear how kinky he actually was, she relished the opportunity to go full domme on him. She started to wonder if she should order that dominatrix outfit she'd been eying. In the meantime, she focused on the present moment. After all, the situation was so delicious that she had to savor it: seeing him bent over before her, his ass clapping, and his erotic moans.

Glancing over to the tv, she happened to notice that the "are you still watching?" notification had come up. Admittedly she was paying much less attention at that point, but she still liked having it on the background. She looked to her new boyfriend. "Hey," she said "isn't the remote in front of you? Get that notification off the screen, I like having background noise to help muffle all the slutty sounds you're making."

"Seriously?!" He'd noticed the remote previously, but it was just out of arms reach. His body was shaking and he was on the verge of climaxing, so even something as simple as reaching for it would've been difficult. "Okay, h-hold on..." he desperately reached for the remote, which was just over the armrest on the side table. He tried to crawl forward just a little, and she responded by moving slightly forward herself. All the while, she was still firmly grasping his hips and railing on him.

He grabbed the remote, then he felt her hand smack his ass again. He winced and let a soft moan.

"Good god, those sounds you make are so adorable." He couldn't see it, but he could tell by her voice that she had a smug grin on her face. "You come across as so refined and mature, but now you sound like a cat in heat."

"S-Shut up!" He grabbed the remote again, then finally pressed "yes" on the screen. "There, are you happy now?" He looked back, his whole face red as he breathed heavily.

"Yes, thank you. As a reward, you get a prostate orgasm!"

"Weren't you going to give me that already?" Barely able to hold himself up, his head collapsed on the sofa while his ass was still raised.

"If you hadn't resumed the show like I asked, I would've denied you an orgasm and just pulled out. But since you were a good boy and did as I said, I'll make you come."

"I'm glad I did it then..." as much as he expressed annoyance at her teasing, he was still embarrassingly getting off from her strap. Starting to feel close, he reached down and started stroking his cock.

"Oh no you don't!" She swatted his hand away. "Good boys come only from their pussies. I don't want you touching your dick until you climax."

"Is that why you haven't been touching it?"

"Exactly! And judging by how much precum you've been leaking, I think penetration alone will be enough for you."

Much to his dismay, she was right. He'd gotten off on penetration alone before, and this was no exception. He could feel the semen rising in his sensitive, throbbing shaft. He gripped the pillows so tightly that his knuckles turned white.

"Cum for me, bitch!" She commanded, pulling his hair again.

"I'm going to-" He couldn't even finish his sentence before he came. He had to bury his face in a pillow just so his moaning wouldn't be so loud as to bother the neighbors. His body trembled, as semen spurted out from his cock.

Rolling over on his back, he breathed heavily as he tried to catch his breath. He'd taken some pretty big dildos before but having something of the same size rammed into him by someone else felt different. Looking up at her, she looked rather satisfied with herself.

"That was awesome." She crossed her arms. "I really had you howling."

"You made it pretty difficult to keep my voice down..."

"Guess I did. Well," loosening the belt from around her hip, she took off the strap "either way that really turned me on. I'm going to go wash this off and put it in some warm water. When I get back, you'll use your mouth to pleasure me. Got it?"

"Yes, master."

After leaving for a few minutes, she joined him on the couch again. Spreading her legs out, she snapped her fingers then pointed to the floor. "Down on your knees."

He quietly nodded and got off the couch so he could kneel before her. Sitting with her arms and legs sprawled out, she looked rather domineering from his angle. His head between her thighs, he saw that she definitely wasn't lying about how much pegging had turned her on; she looked really wet. He started working his tongue along her drenched pussy.

"Oh yeah, just like that. That's a good little kitten." Running her hands through his hair, she resumed watching the show.

Sticking his tongue out, he ran it around it around her walls, then used his hand to gently rub her clit. He felt her shutter, which was all the feedback he needed. She gathered his hair to the back of his head and held it there in a makeshift ponytail, so his hair didn't get in the way of his work.

Although he used his mouth and fingers on her whole pussy, he was sure to give the clit special attention. Flicking his tongue on it, licking, sucking, and fingering. He'd eaten people out before, so he had a good idea of how to pleasure her (though he was still figuring out the particulars of what she liked). He didn't even need to ask if he was doing a good job, both because of how wet she was and also because he could feel her shuttering and hear her moaning. Perhaps the best feedback was when she praised him, calling him a good kitten.

On her end, it felt like she was in heaven. Watching a good show while having a cute boy on his knees and pleasuring her was an excellent way of spending the evening. Their little pegging session was still on her mind, which only turned her on more. Yet again, she had to remind herself to savor the present moment and not let her mind drift off.

Although Casey was partially paying attention to the audio coming from the tv, his main focus was on her. A sour taste on his mouth and his nose tickled by her hairs, it was hard to focus on much else. He could tell she was starting to get close, and made sure to go for her weak spots. When she finally came, she gripped his head tightly and squished his head between her thighs. Even with his ears pressed against her legs, he could hear her moaning. Of course this also meant there was no avoiding getting squirted on since she'd locked him in, but that was simply part of the experience.

Spreading her legs out again, he was released from her tight grip. She laid back and breathed heavily. "That felt so good."

Still kneeling, he did the pawing motion again. "Thank you, master."

She groaned. "So cute...you're lucky I'm tired. Otherwise seeing you do that would make me go crazy."

He giggled, before rising to his feet. "It's rather flattering that I have such a strong effect on you. Course, I guess it goes both ways. I'll admit, I don't recall the last time someone had me moaning like that."

"That's high praise." She shooed him off. "Now go wash off. I can't cuddle with you if your face is a mess."

"Yeah, I was about to go do that."

Once he rinsed off, he returned to her side and they resumed watching tv. Only now, they were snuggling up next to each other. Apparently realizing her initial mistake with the foreplay, she tried to make things up in the aftercare. She started being more attentive, asking if he needed anything and being sure he was comfortable. Frankly, however, he didn't need much. At that point all he wanted was water, a blanket, and cuddles (and she was happy to oblige him).