Chapter 1: Measuring Contest
It was a late night in the Gryffindor Common Room. The sixth year boys were all staying up, talking about the most popular topic with men their age: girls.
"Who here has gotten shagged in the sack?" Seamus Finnegan called out.
Harry Potter, Ron Weasley and Dean Thomas all raised their hands. However, Neville Longbottom's hand remained noticeably, embarrassingly, by his side. The Herbology protege blushed when Seamus made a point of calling him on it.
"Never been shagged, have you, Longbottom?"
Neville flushed and shook his head.
"Ever been given head?"
Another denial.
"A wank?"
"With what, mate? His own lilly-white hands?" Dean cackled. Harry punched him on the arm, indicating the teasing was getting a little out of line. For his part, Neville remained silent in affirming his inexperience with all of these. He was a virgin in the purest sense... and had no idea if that streak would ever be broken.
That didn't mean he didn't dream, fantasize about girls. There were several good candidates that he fancied, and one strikingly beautiful witch in particular.
All alone in his four-poster bed that night with the curtains drawn, Neville humped his pillows as he thought of her bushy brown hair framing around her round, pretty face like a halo. He thought of her beaming smile, the way she bit her lip whenever she answered a question in class. The confident air in her svelte body as she cast a spell. Her nice, surely soft skin. Her cute arse swiveling in those tight jeans as she walked. Hermione Granger's piercing brown eyes... those full lips...
Neville's entire body seized as he thrust a little too hard and too long. He felt the muscles in his organ pulse, and a sticky substance coat his legs. He had jizzed all over himself. Slipping into the bathroom, he cleaned himself before returning to bed without waking the other boys. Placing the rumpled pillow back under his head and rolling over, he went back to sleep.