All this flashed through Vanessa’s mind in an instant. I do want to be close to my guy–as close as I can possibly get. So she said, “Okay.”
But her response didn’t sound at all confident.
“You really do?” he said.
“Yes! Please! You, um, need some lube, don’t you?”
Jack continued to gaze in wonder at her as he slowly got out of bed, went to the medicine cabinet in the bathroom, and brought back some hand lotion. “This will do,” he said.
He put it on her himself, much to her own mortification. The feel of his fingers back there caused her to giggle–but as he was applying the stuff he sensed her muscles tightening up, so he squeezed her bottom and said, “You have to relax, dear. It’ll hurt if you tense up.”
What he meant was: It’ll hurt a lot more if you tense up.
Vanessa was lying flat on her stomach. She looked so small and vulnerable that Jack wondered whether he had the gumption to go through with this; but on the other hand, she was so ravishingly desirable at that moment that his member actually quivered with the anticipation of invading her bottom. He’d done this plenty of times with his ex-wife and others, but doing it to this little girl (no, by heaven, she’s a young woman!) was extra special.
And so he entered her anus–as gently as possible. But even so, she let out a huge gsp at the unusual sensation, and her eyes bugged out as he forged slowly but relentlessly in. He couldn’t, of course, go in all the way; but he went in far enough for Vanessa to feel that some strange creature was tunneling through her body and might, strangely, come out her throat.
She couldn’t even tell if she was in pain or not: the feeling was so peculiar! In spite of the lube, Jack had a bit of difficulty establishing a proper in-and-out rhythm; but when he did so, also reaching around her body and taking hold of those little breasts in his hands, she felt incongruously like some sort of sex doll that a lonely bachelor was using to satisfy his urges. Time stood still as she sensed nothing but the repeated thrusts of his member, his hot breath on her neck and cheeks, and his hands fondling her tiny nipples.
But after a while, one of his hands slid down her body and fastened onto her sex. Both he and she could feel the residual wetness down there (a mixture of his juices and hers); and as he began stroking her there, waves of pleasure fused with the bizarre sensation in her bottom. His goal was clearly to engender a simultaneous climax–and, to their mutual surprise, he managed it. As he started sending thick streams of his second emission into her, he coaxed a sudden and thunderous orgasm out of her, causing her to emit a high-pitched squeal that somehow embarrassed her, as if there were other people there to listen. She clapped a hand over her mouth, but little mews of pleasure still came out of her throat as she felt her derrière flooded with his volcanic discharge.
When Jack was finished, he pulled out a little too fast, causing Vanessa a final little jolt of pain. But overall, insofar as she could think coherently, she felt that this new experience–on top of the earlier new experience that had led to her deflowerment–was definitely worth the effort.
Jack trudged off to the bathroom to wash up, then returned and slipped back into bed. “Did you like that?” he said.
She nodded enthusiastically.
“I’m glad,” he said, pasting a kiss on her mouth.
She had some dim sense that, even now, after she had lost her virginity twice, the session was not over. As they cuddled for many minutes, saying nothing, she wasn’t at all surprised to feel a hardening down in the area of his groin. In fact, she had come to feel that his reaction was a fitting testimonial to her own femininity.
But the problem that had come up earlier now reared its head even more emphatically.
“What do you want to do now?” she asked. When he said nothing but only gazed pleadingly at her, she said, “Now I’m sore in both places.”
“There’s something we could do,” he said tentatively, “that shouldn’t cause you any more pain.”
“What’s that?”
“It’s called sixty-nine. Do you know what that is?”
She nodded. Someone had explained that to her a few months ago.
“Would you like that?” he went on.
“I’m a little messy down there. Maybe I should clean up.”
“That doesn’t matter.”
“Can I be on top?”
“That would be the best way.”
She at once spun around, facing his cock as she presented her genital area to his gaze. That area was indeed dripping with their fluids, but he proceeded to lick and nuzzle it without the slightest concern. For her part, she looked upon the phallus now looming up in front of her face as if it was a kind of towering obelisk that she felt compelled to worship. And she was happy to do it.
At first she only licked the shaft up and down, using one of her small hands to keep it upright. Then she stuck as much of it into her mouth as she could–which wasn’t much, but with practice she managed to get about half of it in. She now used the other hand to tickle the heavy sac below his cock, which fascinated her so much that she cupped it in her hand and rolled it around as if it were a bag containing two large marbles. It was actually hard to focus on pleasuring him while she herself was receiving so much pleasure from his lips and tongue; and, as the process went on for fifteen, twenty, thirty minutes, she thought she might have had two separate climaxes, or perhaps a single climax with two peaks, while she used her own mouth and hands to make him explode one more time.
She swallowed every drop, recognizing how precious this substance was–the very essence of his masculinity! As they were both relaxing after their paroxysms, teasing each other’s genitals as if they couldn’t get enough of the touch and taste and aroma of them, they simultaneously and spontaneously said those magical words that every person wants to hear:
“I love you, Vanessa.”
“I love you, Jack.”
They laughed at the coincidence, and Vanessa quickly spun around and pasted a kiss on Jack’s mouth. Then they fell asleep.