Previously published on The Overflowing Bra. Edited to comply with Literotica site standards.
All characters in this story in erotic situations are 18 years or older.
Prologue: Before the Wishes
Caleb
Caleb had only one problem in his life: his dick was too big. "The Dragon," as he called it, was 11" long and 2.5" wide, and made dating hell. He'd never had trouble getting dates as he was tall and not ugly. Unfortunately, when things got hot and heavy and he brought out The Dragon, most of his dates refused immediately. One or two let him try to put it inside, but gave up quickly. He learned how to eat a girl out like a champ, but thought he would die a virgin.
That was until he met Paige. He had no idea why she asked him out, as they were polar opposites. She was a cheerleader at their high school and was extremely popular. She had a lot of friends in the sports and cheerleader crowd, while he had a few close friends from the anime club. He just knew that one day she approached him and asked him out. He thought it might have been his height; he was one of the tallest guys in school at 6'4" while she was only 5'. He was skinny and unathletic while she was curvy but toned from cheerleading, with perky B-cup breasts, a tight ass, and firm, muscular thighs. Their contrast sometimes attracted stares. They didn't have much in common, but to his surprise, they still got along. She was bright and cheerful, and listened intently to him talk about his interests. In return, he let her lecture him about cheerleading competitions, and was amazed that she could make it sound interesting.
She also conquered The Dragon. The first time they'd done it, he was terrified that she would reject him like the others. He started by eating her out, which rewarded him with her muscular thighs gripping his head. He could tell when she came in his mouth, which made him harder than he'd ever been. She told him to take his pants off and said to put it in her. He sighed and stripped, expecting instant rejection, like so many times before. Instead her eyes widened and she reached forward and gripped it with dainty fingers that couldn't wrap all the way around it. She tried to suck on it, but couldn't hold it in her mouth for very long before her jaw seized up. "It's huge," she whispered. "How have you fit it in anyone?"
"I haven't," he answered. "It doesn't fit."
She looked at him with her big eyes, gave him a grin, and said "oh, we'll see about that. I'm not a quitter." She positioned her feet on either side of his hips and got in a squatting position. She positioned the head of his member by her opening, which he noticed was glistening.
"Wait!" He said, "you don't have to do this if it's too much."
"But I want to," she replied, and lowered herself. He saw and felt the head disappear. "Oh!" she said, her eyes wide.
"Are you okay?" He asked.
"I'm, uh, fine," she grunted, breathing heavily. "I can do this." She lowered herself, her face contorted. "Let me do this for you," she managed through gritted teeth.
Caleb didn't know if he was more amazed when he entered her, or when she bottomed out on him, gasping. He knew from the way she was breathing and the way her face contorted that she had to be in a lot of pain. He also knew that it felt really good, like nothing he'd ever felt. She lifted up a bit and dropped. He felt her shivering and wondered how long she would be able to keep it up. Fortunately, he didn't last long. He felt it coming and gripped her hips as he exploded inside her. He thought he saw stars.
Paige
Paige only had one problem in her life: her pussy was too big. She knew she was hot. She was a popular cheerleader, 5 feet tall with perky B-cup breasts and tight, muscular ass and thighs. She had plenty of prospects among the athletes, but none of them could get her off. All of them felt to her, to use a crude expression, "like throwing a hot dog down a hallway." She thought she would never get off during sex. She bought the largest dildos she could find and tried to be content.
That was until she heard about Caleb. All the girls would gossip in the locker room, and occasionally the talk would turn to the boys they dated and the sizes of their respective equipment. She knew how big a few guys were and could contribute, but then she heard about a boy at their school with a monster. Supposedly none of the girls he dated could fit it. One of the girls there had tried as a challenge, but quickly gave up, and tried to dissuade the others from trying.
Paige asked him out the next day. She knew him as that tall skinny guy in history class. He wasn't bad looking, and figured it was worth a shot. They got ice cream together and talked. He was awkward and nerdy, but was also polite, courteous, and listened to her. She'd worn a low-cut top and a push-up bra to get him in the mood, but he stubbornly looked her in the eyes. That won him some points.
It took almost two months for her to get him into bed. The night of senior prom, she told her parents she was staying at a friend's house, but got a hotel room just for her and Caleb. He seemed hesitant about going all the way at first, but when he ate her out, she had to bite her lip to keep from screaming. 'Where did he learn to do THAT!?' she wondered to herself. 'Oh, and THAT! And what the FFFFFUUUUUUU......' until her mind went white.
When she came to herself and caught her breath, she said "take those pants off, I want you in me." He complied and there it was, the monster she had heard so much about, all eleven glorious inches. She couldn't even get her hands around it! "It's huge!" she whispered. She needed it. She positioned herself on top of him and stuck it inside. She gasped. It was better than she imagined. He tried to talk her out of it, but she was determined. She slowly lowered herself onto it; she knew if she went any faster she would scream in pleasure (not that her parents would mind, they were out of town, but she was sure the neighbors would hear and call the cops, the damn busybodies).
When she bottomed out, she was certain she would scream if she unclenched her jaw. No one had filled her like this before, and it was a boy she actually liked. Amazingly, it still didn't fill her completely. How deep was she? But it was better than any dick she'd taken before. Still, she wished he were bigger. She felt self-conscious about her huge pussy again. She moved herself up and down, gripping as hard as she could. Although there was still room, it was the best sex she'd ever had. She orgasmed several times and had to scrunch up her face to keep quiet. Finally, she heard him gasp and shudder and explode inside of her. She crawled up his body and felt his softening member pull out of her before plopping on his belly.
"Thank you," he gasped.