She let out a low, throaty groan, followed by a whimper, as he pressed his head against the opening of her pussy. Looking at the size of his cock by the size of her opening, Ben realized that this was going to be more difficult than he had imagined. All those times fantasizing about this moment, the moment that he lost his virginity, he had never considered whether or not he'd actually fit inside a woman.
"Just push harder!" Leah moaned, pushing back against him.
"But I don't want to hurt..."
Before he could finish the sentence, she reached between his legs, guiding his cock head to the right angle and with one movement and a loud yelp, she pushed him in.
***
Eighteen years old. Finally.
Ben looked at himself in the mirror. Over the last couple of years, he had grown a few inches, put on a few pounds, and finally had started to look like a man. He even had a little chest hair. Part of him had looked like a man for years, though.
Ben had always been the smallest kid in his class, considering his parents had skipped him ahead of kindergarten. Sure, he had been ready for the academic challenges of first grade early, but the social challenges had proven insurmountable. He was small, scrawny, and socially awkward. Early on, he learned that just because he knew the answers in class didn't mean he should raise his hand, but those first few years had given him a reputation that he couldn't overcome: nerd.
Half the time, Ben tried to embrace his reputation, committing himself to school, smirking when other kids didn't know the answers, bragging about his abilities on tests. The other half of the time, though, he resented the pressure his reputation put on him. As he grew older, the resentment took a greater and greater hold of him and his grades slipped. Struggling to keep up in school, he learned to hide his panic behind a "fuck it, I'm too smart for this anyways" attitude.
No matter which attitude he took, though, he just couldn't seem to make the other kids like him. The bullies came after him almost automatically, and even the nerdy kids knew better than to associate with him. He was so much smaller than all the other kids, he couldn't defend himself.
Looking at himself in the mirror at age eighteen, Ben wished that he could say "look at me now!" to those classmates. He wished that not only had he grown into his body, but that he had also grown into his self-confidence. Unfortunately, Ben still felt like that skinny kid, hiding in the bathroom from the bullies.
