As for Jeff, his fingers had reached the barrier that was her hymen, and he was unsure of how to proceed. He wanted more than anything to be the first man Natalie made love to, but didn’t want to assume she was ready for that. Still, he knew he had to ask.
“Can I make love to you sweetie? I promise I’ll be as gentle as possible but it will mostly likely hurt you this time around. I’m afraid it’s unavoidable.”
Natalie, lost in pleasure, was surprised he thought he even needed to ask. She opened her eyes and found him gazing at her. She nodded. “You’re the only person I would trust in the world to do it. Just please be careful.”
“Don’t worry sweetie, I will,” he assured her. Then he grabbed the pillow she wasn’t using from the head of the bed. “Turn on your tummy, Natalie, and I’ll put this under your hips.”
She looked a bit uncertain. “You’re not going to spank me, are you?”
Jeff almost groaned aloud at the prospect, but managed to choke out, “No, I’m not going to spank you Natalie, it just may be more comfortable if your first time is on your tummy.”
“Oh,” she said, blushing. Nervously she turned on her stomach, feeling vulnerable as her entire backside was exposed.
Jeff slipped the pillow under her hips and stopped to kiss the spot just above her bottom. “You’re so pretty,” he whispered. He had somehow managed to pull off his boxers somewhere in between kissing her nipples and rubbing her pussy, and he lined up his considerable erection with her small opening. Natalie shuddered slightly and he knew he had to go slowly so she wouldn’t panic at the last second.
He began to massage the curve of her bottom with both hands, adding feather-light kisses to the tops of her spread thighs. Eventually he felt her relax, and was able to slip a few inches into her pussy. Natalie gasped, but made no indication for him to stop, so grasping her waist he pressed himself in more firmly. When the head of his shaft bumped her hymen he knew they were at a point of no return. He drew back and with a short, hard thrust rendered the bit of membrane into oblivion.
Natalie gave a small involuntary shriek as her innocence was torn away. It stung badly and she was unable to withhold a few tears. Imbedded to the hilt, Jeff stayed absolutely still. “I’m so sorry sweetie, do you want to stop?”
However, the pain was already fading and Natalie shook her head. “No, just stay still for a minute.”
He did as she asked and eventually the pain faded completely. It was replaced with the odd feeling of being stuffed, but when she moved her hips a little, she found it to be a very nice sensation. Taking his cue, Jeff began a slow thrust inside her, careful not to go too fast. When Natalie began reverse thrust, urging him on with whimpers and little breathy pants, he picked up the speed.
So wet and snug was she, he felt his end approaching. Desperately he reached under and began stroking her sensitive clit. It didn’t take much digital attention before she came, arching back against him as the orgasm pounded through her. Her pussy clenched around his shaft and he felt his own orgasm overtake him.