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Dude X MiseryCloud

She smiled and took him into her mouth once more. Her hands worked his base while her lips and tongue stimulated his head, lapping up the precum he produced. Her eyes moved to look up at him while she pleasured him, a small moan coming from her as shesaw the look on his face.
 
He continued to writhe in utter pleasure and bliss. This was the best blow job he'd ever received, and this was only her first time. After another 5 minutes of her sucking his cock, he felt himself coming close.

"I'm close" he moaned out, warning her as he felt his cock beginning to spasm in pleasure
 
She moved away, her hands still moving on him as she backed up. Her eyes watched as his cock spasmed several times.
 
James grunted in urgent pleasure as he felt himself go. The combination of him not having sex in a long time, and the past 15 minutes of Willow's stimulation caused his cock to spasm and erupt in a very intense orgasm. Many shots of cum sped out out of his cock, shooting high. His toes curled in ecstasy as it took him a full minute to come down from his climax, and he began to pant heavily, his entire body sweaty.
 
Her eyes were wide as she took in the sight of the white fluid spurting from him as he twitched and spasmed, his big body jerking. Once it stopped coming she moved up beside him, placing a small palm over his heart where she could feel it beating rapidly against his ribs. "Are you alright?" She asked softly, her light brown eyes filled with concern as she looked down at him, smoothing back his sweaty hair.
 
"More than alright" he said, panting as he kissed her lips thankfully

"That was amazing. Especially for your first time doing that" he said, gently holding her

"It has been a while since I was satisfied like that. Would you like me to clean myself off before we continue?" he asked her
 
She looked down at the pooled white on his stomach and ran a finger through it, bringing it up to inspect. "This is what makes little ones yes?" She asked, looking at him before grabbing a cloth and wiping him clean after dampening it.
 
"Yes" he said to her, eventually catching his breath

"So, before we continue, I want to tell you that it will hurt a bit" he said

"I'll be very gentle, and I'll stop if you want me too. However if you want to stop now, I'd understand" he said, gently caressing her cheek
 
She gave him a soft, almost shy smile. "I want to continue. I want to know what it is like to lay with a man." She whispered, leaning in and gently kissing him. "Will you show me the way?"
 
He nodded, kissing her back and running his fingers through her hair. He gently laid her down, kissing her deeply as the tip of his cock slowly prodded her wet sheath. He broke the kiss and sat up, gently holding her hips

"Just tell me when to stop, and I'll stop" he said, very slowly easing the head of his manhood into her
 
She wriggled a bit at the uncomfortable fullness of him inside her. Suddenly, he seemed to be pushing against a wall inside of her and she gasped in surprised pain, her hands flying to his biceps as she closed her eyes for a moment.
 
He stopped and pulled out, kissing her cheek to comfort her

"Are you alright?" he asked her

He wanted to take her, but didn't want to force himself on her and hurt her in the process
 
She looked up at him, trembling slightly. "I-I'm okay. Keep going." She whispered, wriggling to get a bit more comfortable on the bed. The women of her village had told of their first times being excruciating but she knew this man would never intentionally hurt her.
 
He nodded and positioned himself outside of her, before slowly easing himself into her, a little deeper this time

"Does it feel better?" he asked, gently caressing her hip
 
Again he pushed against the barrier, and again it hurt. She winced but said nothing about it, only nodding for him to go further.
 
He gently locked lips with her, and very slowly easing his entire cock into her incrementally. He kissed her lips as he slowly caressed her body to comfort her.

"You ok?" he asked her
 
Willow kissed him back, clinging to him as he finally broke through and burning pain erupted in her loins. She couldn't help but cry out, a tear falling as she felt a trickling warmth between her legs.
 
He pulled out quickly and gently caressed her cheek

"I'm so sorry!" he said, backing away. He knew that if he had been any smaller it wouldn't have hurt her so much, but that was simply not the case.

He got up and got a clean towel and handed it to her, gently holding her hand in concern
 
She held his hand tightly, her thighs quivering. "W-why did you stop?" She asked quietly, looking over at him.
 
"I didn't want to hurt you" he said, laying on his side beside her

"I hoped that your first time wouldn't be so painful. I'm sorry that I'm so big that it caused you to cry out" he said, gently running his fingers through her hair
 
She gave him a shaky smile. "It is natural for a woman's first time to hurt. It got a bit better after you went past my barrier."
 
"Ok. Let's take it slow than" he said, gently hovering over her and kissing her lips, and very very slowly slipped himself in, a little past the head of his cock.
 
She groaned softly. There was very minimal pain as he pushed back in, only a straining fullnes. She clung to him, willing her muscles to relax around him and let him inside.
 
He groaned in pleasure at her tightness and kissed her lips, gently grasping one of her breasts as he slowly pushed himself in
 
Her legs instinctively wrapped around his trim hips, pulling him into her fully as she arched to him. "Nnngh James!" She moaned.
 
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