"Can I touch you?" he asked in a nervous tremor.
She gave him a bigger smile than he had ever seen. "Of course. You can touch me anywhere you want."
And that's what he did. She giggled as he began to run nervous, shaky hands over her. He felt her soft, smooth skin that seemed to go on forever. His hands went up and down her arms, then he crouched and moved them down the side of her legs. This put her pussy directly in front of him. He saw the patch of dark blonde hair. He moved his hands to the back side of her legs, and lifted them up. When his fingers touched the underside of her butt cheeks, he hesitated.
Bailey was breathing hard as she encouraged him, "Keep going. Feel all of me. I want you to."
He kept staring at her pussy as his fingers continued their journey. Her cheeks lifted at his touch, and then he was gripping them in his hands. Her butt was small and tight. He spread her cheeks apart, then pushed them together. He saw a trickle of moisture run down her inner thigh.
"Are you..." he started to ask. Then he brought a hand around and touched the clear fluid.
"Yeah, that's how wet I am right now for you," Bailey said with knees that began to shake. "I love how you're touching me. I love how much you want me. I think I'll need to sit down soon."
"Of course, sure, yeah," Ryan said. He stood and led her to the bed. They sat down, and he put a hand on her boob. And then he kissed her. They stayed like this for a minute or two. Ryan had no way of knowing because for him, time was at a standstill. Eventually, some instinct kicked in, and he began to push her down onto the bed.
"Wait," she said.
Ryan froze, terrified that he had done something wrong.
"It's your turn to get naked," she whispered softly.
He sighed, and clumsily shucked off his clothes, almost falling over in the process. Then he was beside her, pushing her down. She spread her legs, letting his dick rub near her pussy entrance. He tried to push into her. His aim was off.
Bailey giggled, then reached down and took his dick into her hand. "Let me help you out there, virgin boy."
That phrase struck Ryan hard, as Bailey's hand guided him into her. His face mirrored a mixture of horror and delight as he felt himself slide into her depths. "Oh!" he gasped at the overwhelming sensation of being inside his crush.
"Try not to cum too fast!" she said quickly. "Think of something else if you need to."
Ryan was already thinking of something else. The phrase virgin boy. That's what Tabitha had called him. Had Bailey overheard her say that? She couldn't have. Tabitha had been inside of Bailey at the time, and Bailey wouldn't have remembered.
"That's it," Bailey cooed underneath him. "You're nice and hard inside of me. This is what you wanted, isn't it?"
Had Ryan ever told Bailey that he was a virgin? He didn't think so. She might have assumed, but...
She wrapped her legs around him and pulled him deeper. "You have to start a rhythm. You need to go in and out, not all the way out mind you, just to the tip. And then push back into me. Slowly at first, but then you can speed up, and you want to try and go deeper. Good. Just keep doing that."
Ryan found himself following her instruction, even as his mind wondered. She began to moan loudly underneath him. It was incredibly sexy, and Ryan did not doubt that he would have exploded in her several times already if his mind weren't otherwise preoccupied.
"Put a hand on my tit and pinch it!" she ordered.
Ryan obliged. She leaned forward for a kiss, and he gave it. It seemed hollow though. His dick didn't care, and as it surged towards the finish line, he asked, "So, I guess thanks for being a great wing woman."
Her expression became confused. "What? Wing woman? Sure, whatever. Just give it to me harder!"
He did give it to her harder. He was pumping furiously now as he kept to his line of questioning. "You called yourself that earlier, a couple of times actually. You said you'd be my wing woman and help get me laid."
Her hips were bucking under him, trying to get him deeper every time. "How am I doing so far?" she cried out.
He could feel his balls tighten, and his dick begin to pulse inside her. Even so, he looked her in the eyes, and said the obvious. "You're not her, are you?"
The hungry smile she gave him was one he had seen before, on Tabitha. She bucked harder and faster against him as she saw he was right on the edge. Then she gave him an extra show by playing with her tits. "That's not going to stop you from cumming inside of her, is it?"
To Ryan's regret, it did not stop him in the slightest.
The end.