A/n: My drabble entry (and Category Winner) for the First Time prompt (all smutty 'firsts' for these two dorks) in the RomioneQuickieFest'17 on Tumblr. This one is the first time Ron tries something new to please Hermione (and win a bet). Takes place sometime after Ron's 17th birthday.

Rated M for obvious reasons

"You make me break rules!" she grumbled as Ron's lips found their way to the soft spot behind her ear, causing her to suck in her breath. The prat grinned, lips still attached to her skin.

His hand moved away from her bra covered breast and suddenly the hook of her skirt was undone while his large hand was finding its way in.

"Ron?"

The smouldering look in his eyes was the death of the admonition that was coming his way. She gasped when he flicked his thumb under the elastic of her knickers. He cocked a brow, challenging her to quit. She upped the ante by grabbing his shirt collar and pulling him in for a fierce kiss instead. As her tongue sought entrance, one hand pushed its way inside her knickers, with the other still busy on her nipple. She couldn't help but moan into his mouth. Sucking his lower lip between her own, her fingers dug deep into his shoulders leaving marks on his skin for sure. Ron responded by squeezing her bum, not too gently either.

A feeble part of her brain reminded that they ought to stop or this petting session would change into something way higher in her scale of rule-breaking. But any remaining coherent thoughts were erased as a long finger found its way under the thin strap of cloth right between her thighs; his palm still spread over her arse.

"Rrronnn," she moaned, holding onto him for support as her eyes fluttered shut.

Ron responded with a nervous chuckle while his finger rubbed over her most sensitive flesh. Hermione sucked in a breath as he pushed his finger gently.

"N-Not there, a l-little…ahhh,"

Ron was tracing a line beginning at the sensitised nub, still searching for the elusive entrance, fumbling but somehow doing an amazing job with it. She gasped aloud when he finally found his target.

"Here?" he asked huskily, his breathing laboured.

"Y-Yes,"

"Should I- you know, push it in?"

She opened her eyes briefly to watch him. The new discovery seemed to be driving him equally crazy.

"If you want to…" she whispered, and then, to give him a better hint, lifted her leg to rest it on the bench behind him. He caught on and his finger probed in just a little more. Hermione moaned and he swore loudly. It was slightly uncomfortable but intensely pleasurable.

"More?" he inquired as his eyes begged her to agree.

"Y-Yes," she responded breathlessly, fisting his shirt hard.

His long digit entered further, the task made easy with the moisture that her body provided eagerly. Hermione squirmed on his lap as his finger went two-knuckles deep and then a bit more. The sensation was mindboggling. Not just that it was more than anything they had tried so far, but they were both also prefects doing their rounds, who had locked themselves inside an empty classroom. All because her boyfriend had challenged that she didn't have it in her to accept this dare.

It was so much better when it was his fingers, she thought to herself. Since she had proved her point already, Hermione chose to relax and enjoy.

"More… please…" She could feel Ron almost shaking, and it was a while before he replied, his voice strained.

"No, I'll hurt you."

"Please?"

His lips cut off any further pleas and rather than do as asked, he slowly pulled his finger out. Her protest died on her lips as his hand was inside her knickers again, from the front this time. She lost it when his index and ring finger pressed at her other lips. Spreading them apart he pushed his finger between her folds once more.

"You are so small, Hermione. Can't risk hurting you," he managed, finger still at work, careful but a little more desperate with each thrust. She was sure he couldn't hold back the increase in pace; she didn't want him to, either. Hermione came undone as the digit curled within her, sending her senses into a frenzy.

...

"I won," she declared much later, still blushing crimson at the memory.

"So did I," he winked before stealing another kiss.

A/n: A few words in this drabble have been replaced with their more literature-friendly version because this is not Tumblr!