Click here to read the previous parts of the story.
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"What do you think about him?" Ally asked as she subtly gestured towards a tall guy in a pair of jeans and a t-shirt.
Rocky tried his best to look without staring. As he did, Ally leaned over and softly kissed his neck.
"Do you think his dick is bigger than yours?" she whispered.
"Yes," he answered.
"And do you think he'd fuck me good, baby? Do you think he'd make me cum all over his big cock?"
The fact that they were in public - they'd selected a bench in a well-traveled part of the park closest to Rocky's apartment - made their little game all the more arousing. Rocky was a little self-conscious about the public kissing and touching and the fact that he now had an erection, but the sexual excitement coursing through him washed away any real worries.
"Yes, he would," he answered. "He'd fuck you like you deserve to be fucked, Ally."
She kissed him on the cheek and crossed her leg. Her dress rode up a little and exposed the smooth flesh of her thighs. Rocky thought of how he'd spent quite a bit of time between those lovely legs the night before. His tongue, fingers, and a dildo had provided Ally with a handful of orgasms before she'd welcomed his cock inside her. He hadn't lasted long, mostly due to the fact that Ally talked dirty about his small cock the entire time, bringing him to an orgasm that left his body shaking.
"How about this guy," Ally said as she gestured towards a nerdy-looking guy wearing a pair of cargo shorts, an anime t-shirt, and sneakers with ankle high socks.
At first Rocky was inclined to say that there was no way the nerdy guy would give Ally pleasure. He took a moment to study him, though, and noted a surprising level of confidence emanating from the anime fan.
"You're not sure, are you?" she asked.
Rocky shook his head and smiled. "I'm really not. I think there's a chance he's got a big dick."
He looked at his girlfriend to see her staring at the nerdy guy. She bit her lower lip and Rocky wondered if she was actually a little bit attracted to him or if she was just putting on a show to make their little public game more exciting.
"Is he someone you'd actually...you know..." he asked.
She turned to him and smiled. "I have a thing for cute, nerdy guys. He's nerdier than anyone I've been with, but that's no reason to write him off entirely."
Rocky watched his girlfriend turn her attention back to the nerdy guy, who had stopped and was chatting up a couple of women that looked way out of his league. He exuded confidence as he talked to them and one actually seemed a little bit interested. The conversation was over fairly quickly and no numbers were exchange, but Rocky was more than willing to admit that the guy possessed an uncommon level of confidence for someone that dressed like he was going to a comic book convention.
"I'll be right back," Ally said.
She got up and made a beeline for the anime fan. He saw her coming and stopped. He did a quick scan of her body - very quick - and flashed an admittedly charming smile as she approached.
Rocky wasn't sure what to expect - he had no sense of Ally's intentions as their little game had never gone further than speculating about guys - and he couldn't help but feel surprised and more than a little jealous as his girlfriend started flirting with the nerdy guy.
The conversation went on far longer than Rocky expected - at least five minutes - and it ended with a rather obvious exchange of numbers and a hug. The hug lasted for a handful of seconds and the nerdy guy damn near grabbed Ally's ass. She then turned and walked back to the bench while the anime fan stared at her ass for a few seconds before setting off through the park, this time with a big smile on his face and a confident bounce in his step.
"Did you actually give him your number?" Rocky asked as she sat down.
Ally smiled and nodded.
"Your actual number?"
"Yes, my actual number."
"Wait...so...wait, wait, wait...so are you actually considering...I don't know. I'm not sure what the next step would be, actually. Like, are you going to go on a date with him?"
She shrugged. "I have no idea. He's cute. He's charming. He's funny. He's confident. I mean, if he showed up to a date dressed like he was today I would absolutely walk out of that date, but assuming he knows how to dress himself I could see taking the next step with him."
"You mean...like, you'd have..."
Ally turned to Rocky and leaned in to kiss him on the cheek. "Relax, baby. There's no need to panic. If you're not ready for what comes next then I'm in no rush. I like our sex life. I like your tongue. I like your fingers. I like when you fuck me with my toys."
"But you'd...you'd like to have a real cock, too. A big cock."
She smiled and nodded. "Of course I would. Every woman likes getting fucked by a big cock every now and then. That doesn't mean I'm in any rush, though." She put her hand on his knee and ran her fingers up his thighs, stopping a handful of inches short of his crotch. "I would like to cuckold you at some point, though. I would like to have the experience of a big cock stretching my pussy while you watch. I'd like us both to have that experience because I know we'd both enjoy it so much."
Rocky was equal parts turned on and anxious. He found immense pleasure in Ally talking about his small cock and his inability to pleasure her. He found the same kind of pleasure in talking about her having sex with other men. The idea of it becoming reality, though, was far more angst-inducing than he'd imagined.
"And, for reasons I can't quite explain, I'm surprisingly turned on at the idea of cuckolding you with a nerdy guy like Adam."
"That's his name?" Rocky asked.
"It is. And he is nerdy. He's into anime. He's into video games. He's into comic books. He was just at the comic book store around the corner, in fact. How would it feel if I cuckolded you with a guy like that instead of the tall, muscular, handsome jock types we've been looking at today?"
"It would be harder," Rocky admitted.
"I wonder if that's why it turns me on," she speculated. "Because my pussy is really wet right now, Rocky. Really, really wet, and not for your little dick. My pussy is wet because I'm thinking about getting stretched by that cute nerd while you watch."
"How do you know he has a big dick?"
"Because I asked him," she answered.
Rocky was stunned. "Wait, really?"
Ally nodded. "I told him that my boyfriend had a small cock and I was interested in cuckolding you with a big dick guy. I told him there was no point in us exchanging numbers if he didn't have a big dick. He assured me that he does. He said he'd be more than happy to send proof, too, that I just have to ask and he'll happily send a video."
Before Rocky could say another word, Ally pulled his lips to hers for a deep kiss with more than a little of her probing tongue in his mouth. He surrendered himself to it and by the time she pulled away he sported a painful erection and a wealth of desire coursing through his body.
"I'm very horny," she said. "I'd like to go home now."
Ally stood and offered her hand.
"I can't," he said. "I need a minute."
She looked between his legs, smiled, and said, "Baby, your little dick doesn't make a big enough bulge for anyone to notice."
Any other man would have been destroyed by a comment like that. Rocky, though, was hit with a tidal wave of arousal. He stood, took her hand, and kissed his girlfriend again. He ran his hands down her back and thought of Adam doing the same thing. Then, in an instant, he was picturing the nerdy guy fucking Ally and Rocky's erection raged to the point that he was ready to run home and fuck his girlfriend.
They walked hand-in-hand to the parking lot and Rocky drove home. On the way, Ally alternated between masturbating and teasing him by leaning over to stroke his dick. At red lights and stop signs she'd kiss him, ensuring that they both remained in a state of heightened desire.
Rocky figured they'd get right to it when they got back to his apartment, but Ally had other ideas. They headed for his bedroom, made out as they stripped each other naked, and crawled into bed. Rocky moved to get on top of her, but Ally pushed him back and grabbed her phone.
"What are you doing?" he asked.
"Asking for a video."
It took him a few moments to realize that she was texting Adam and asking for video proof of his big cock.
"Lie back," she said after sending the message.
Rocky rolled onto his back and she cuddled up next to him. She kissed his neck and took his cock in her hand. She stroked him and moaned and Rocky closed his eyes as a wealth of pleasure washed over him.
"I hope he really does have a big cock," she whispered. "I hope it's so big that I can't even fit my fingers around it. I hope it's so big that it actually hurts a little when it first slides into me. I hope it's so big that I see stars when I cum all over it."
"Ally...I'm close."
She laughed softly and released his cock from her grasp. "I love that you're so into this, Rocky. I love that this turns you on so much. It makes me...it makes me really happy."
Rocky considered telling Ally that he was in love with her - he certainly felt it - but it struck him as a bad moment for that sort of declaration. Instead, he rolled her onto her back and took one of her stiff nipples between his lips. She moaned and ran her fingers through his hair. He moved a hand between her legs and slipped two fingers into her wetness before finding her clit with his thumb and offering
enough pleasure to make her moan even louder.
Then her phone buzzed. She rolled over, grabbed it off the nightstand, and turned away from Rocky, preventing him from seeing the screen.
He saw her eyes go wide, though. He saw her lips curl into a smile. He saw a look of pure arousal wash over her face.
"Wow," was all she said.
"Is it big?"
Ally looked at him and nodded. "Actually, big might not be accurate. Huge is, I think, a better word for it."
Then she turned the phone towards him. Rocky saw the image of another man's cock. He was holding a can of Coke next to it. His cock was nearly as thick as the Coke can and quite a bit longer.
Ally pressed play. Rocky watched as Adam stroked his cock a few times while holding the Coke can next to it.
Rocky experienced a deep sense of inadequacy as he watched the four second video. His cock was below average, but compared to Adam he was genuinely small. Tiny, even. The kind of cock that Ally wouldn't be able to feel after Adam had been inside her.
"How do you know it's real?" he asked. "The video, I mean. How do you know he didn't just download something from the internet."
"Fair point," Ally replied. She turned the phone back towards her and sent a text. She looked at Rocky and smiled. "I think it's real. You're right to ask for proof, though."
They kissed. A long, slow, deep kiss. Then her phone buzzed.
Ally tapped the screen. She smiled.
"It's real," Adam said. "And it's spectacular. I promise. If I get a chance, I will make you feel better than you've ever felt. And I'm more than happy to let your boyfriend watch."
Ally turned the phone towards Rocky. She tapped the screen.
Rocky was looking at Adam. He'd filmed his face. He smiled. He then turned the camera around and showed his cock. The Coke can was there. He said the things he said. He stroked himself. It was his cock. It was real. It was stunning. It was bigger than most cocks in porn.
Ally set her phone on the nightstand and kissed Rocky. She stroked his dick while luring his tongue into her mouth. She sucked hard on it and he moaned at her passion.
"Are you really considering fucking him?" Rocky asked.
"Yes," she answered without hesitation. "I'm not going to jump right into bed with him, though. I'll have him take me on a few dates. I want to make sure he's not an asshole and a few minutes of flirting in the park isn't enough time to figure that out."
"You're going to date him?" Rocky asked.
Ally smiled. "No, baby. You're the one I'm dating. I am, however, going to go on a few dates with Adam. We'll go to coffee. He'll take me to dinner. If all goes well, we'll make a third date to fuck and you'll get to be there for that one."
Rocky felt like it was all happening too fast. He felt the angst building and he wasn't sure he could stop it from overtaking him.
"Hey, look at me," Ally said softly.
He met her gaze and she smiled. Rocky relaxed a little as she caressed his face.
"Is this hard for you?" she asked.
"More than I thought it would be."
"Is it harder because Adam doesn't look like a typical alpha male type?"
He nodded.
"It might not make any difference right now, but I think he's going to fuck like an alpha male. He exudes confidence in the way alpha males tend to and he seems quite certain that his big cock is going to make me feel things I've never felt before. Something tells me he feels that way based on experience."
"Yeah?" Rocky asked. "Do you think he's fucked other girls that are dating small dick guys?"
Ally smiled. "Guys like you, you mean?"
A gentle wave of arousal washed over him. Ally must have seen it on his face because she leaned in to kiss his neck.
"It must be hard knowing that your little dick isn't good enough for me," she whispered. "It must be hard knowing that your little dick can't make me cum the way I deserve to cum."
"Fuck...Ally..."
She wrapped her fingers around his cock and stroked him.
"It must be hard knowing that I'm wet for Adam, for that beautiful cock I saw in his videos. It must be impossibly hard to know that there's a part of me that wishes he was in your bed right now, that wishes his cock was deep in my wet pussy right now, stretching me and making me scream his name while you're forced to watch because your dick is too small to get me off."
"Ally...fuck...can I fuck you?"
"Yes."
She rolled onto her back and Rocky quickly put on a condom and moved between her legs and slipped into her wet pussy. They kissed as he began to thrust and he knew right away he wouldn't last long.
"I'm so wet for Adam's big cock that I can barely feel your little dick inside me. I can barely feel you thrusting, baby."
Rocky groaned as his orgasm approached.
"I wish it was his big dick inside me right now. I wish I was getting fucked by that tree trunk between his legs. I wish he was stretching my tight pussy. I wish his fat cock was inside me instead of your little dick."
Rocky grunted and came. He came hard. Exceptionally hard. Ally wrapped her legs around him and kissed his neck and cheeks. Their lips met and she welcomed his tongue into her mouth while moaning and running her fingers through his hair.
"Was that good?" she asked softly.
"That was amazing."
Ally smiled and caressed his face. "I know this is hard for you sometimes and I'm sorry if I'm not always sensitive to that. I do like that it makes you cum so hard, though."
"I do too, and I'm sorry if I'm too sensitive about it sometimes."
"You're not."
"It would turn me on to watch," Rocky admitted.
"I know, baby. I know. Which is why I'm going to insist that you be there when Adam fucks me for the first time."
"Will there be more than one time?"
"If his cock feels as good as I think it's going to feel, then yes, there will be more than one time. There will be lots of times."
That made Rocky anxious, but he knew that he'd be turned on if he hadn't just cum, so he offered no words of protest.
"I'd like to cum now," Ally said. "Multiple times, in fact. I'd like you to fuck me with the toy while you lick my clit."
"It would be my pleasure," Rocky replied.
It was, too, as he made her cum four times. She made him cum again, too, making it an exceptionally hot evening despite the moments of anxiety. There would be more pleasure - and anxiety - to come as Ally made good on her promise to date and fuck Adam.