“I’ve never done this before.”

Grimsley should have saw this coming.  Truthfully, he should have had some sort of hunch based on how bashful this young lady had been, but he wrote it off as just having that kind of effect on people.  However, if he had to gamble on this earlier in the evening, it’d be a bet he lost.  What were the odds of a woman her age having never fooled around with someone?  When he agreed to go back to her room with her, he had no idea that she was a virgin.

Not wanting her to get nervous for revealing such a thing to him, he stole a kiss from her.  This wouldn’t kill the mood.  No, not at all.  Honestly, he should not have been as excited as he was to hear such a thing from her.

“I’m your first?” Grimsley confirmed without allow his mouth to leave hers.  She nodded, and that was enough to send the blood rushing south again.  Between her looks, her luck, and now this, he felt like he had hit the jackpot.  “You really are a lucky girl.  Just relax and follow my lead.”

He guided her back onto the mattress and settled by her side.

“I’m going to take care of you,” he said, teasing the hem of her dress up enough to slide his hand beneath.  “Just tell me if you want to stop or slow things down.  Okay, Annais?”

Annais bobbed her head.  Fingertips elicited goosebumps as they ghosted up her thighs.  Leaning over her, his mouth came down on her neck while his fingers wandered higher.  Her panties were already drenched by the time he reached them.  One of his fingers hooked the string of the bikini and dragged it down her thighs.  Once the article was at her knees, his hand found its way back between her legs. 

“Have you ever touched yourself?” he asked.

“Y-Yes…”

“Guide me.  Show me how you like to be touched.”

Moving his hand under the skirt of he dress, she brought him to her slit.  His thumb brushed over the folds, causing her to shudder.  After a few experimental rubs between her lips, she then guided his fingertips to her clit.  Her thighs squeezed at the first brush of the pads of fingers, and her breathing hitched when he began to trace around it.

Beneath his yukata, Grimsley’s cock was throbbing.  He could only imagine how tight this girl was going to be, how good her pussy was going to feel squeezing around him.  He was ready to get this show on the road.

“Let’s see if you’re ready for me.”

With his digits coated in her fluids, he pressed them inside of her.  She tensed at the intrusion.

“Everything fine?”

Judging by how her lips were parted as she nodded, Grimsley took that as a resounding yes.  He really wanted to blow her mind, to make her first time so good she’d remember him for the rest of her life.  With two of his fingers still in her, he brought his thumb to her clit again.

That little button of hers was stiff under his thumb now; his fingers alternated between pumping in and out of her and scissoring inside.  She bucked her hips slightly and clenched around them.  It was undeniable how much he turned her on, and the feeling was certainly mutual.  He wanted to be inside of her as soon as possible. 

While still fingering her, he tugged the obi around his waist loose with his free hand.  The yukata fell open, exposing that he only wore boxers underneath.  Her stare was fixed on the strained silk while he pleased her.  He looked from her down to his tented boxers then back to her, but her eyes lingered. 

He drew the waistband down and delighted in seeing how her pupils dilated the moment his erection was freed.  He withdrew his hand from her to take care of himself for her viewing pleasure, and she was so transfixed it did not seem to bother her that she was now empty.  She watched intently as he caressed his cock with long, languid strokes.  A steady stream of precum seeped from his slit and coated his shaft with every brush of his palm. 

“Just making sure it’s ready for you,” he said with a half-cocked grin.  “I’d hate for your first time to be uncomfortable.”

“It’s… big,” she said when she managed to pry her eyes away from it.  She paused to giggle.  “God, I’m sorry…  Is that tacky to say?”

“Tacky or not, I certainly don’t mind hearing it,” he laughed.  “You ready to take things further?”

“Yes!” she said with an enthusiastic nod.  He retrieved his wallet that he had been keeping in his sleeve.  Inside, he found a condom and wasted no time tearing into the packaging.  As much as he liked gambles, a kid was one he wasn’t willing to risk… At least not on this girl’s first time.  After he rolled it down his length, Grimsley spread her thighs and positioned himself between them. 

“Make sure you relax,” he told her.  “This may hurt just a bit.  If it hurts too much, let me know.”

“I will.”

Holding himself, he guided the tip to her entrance and began to press it in. 

Oh, this was divine.

She squeezed him like a vice.  The feeling of her tight little hole left him lightheaded.  The only thing that would feel better would be if he were taking her raw.  Despite her inexperience, she had no issues as his length filled her.

“You’re doing great, Ann,” he said to her when he bottomed out.  “How are you feeling?  Good?”

“Mhm…”

Grimsley nipped at her neck.

“Now, I’m not one for taking things slow…  You don’t mind if your first time is a little… rough, do you?”

She didn’t need to answer, the way her pussy clenched around him just for asking was enough confirmation that she wanted him to ravage her.  Yet, he still got the verbal confirmation he desired.

“Please.”