Goody Two-Shoes

"She'll still need the makeup and dress," Jay said. "We're going out to dinner afterward."

"After what?" I asked.

Tillie rolled her eyes. "You are naïve. After he pops your cherry, sweetie. Haven't you been paying attention?"

"I think I'd rather take you to my place, actually." Jay glared at Tillie. "Some people can't mind their own business. Put the dress back on, Sam. We won't worry about the makeup today."

"I'll do it," Tillie muttered.

"Then keep your mouth shut."

I put the dress on again and sat in the chair. Tillie put the makeup on, giving me frequent reminders to hold still. Finally she stepped away and gave me a hand mirror. "What do you think?"

"It looks great. Thank you."

"You're welcome." She helped me out of the chair. "Look, sweetie, no harm meant by the things I said. I just never believed someone your age could be so naïve. Don't let Jay talk you into anything you don't want to do, okay?"

"I'm sure he won't try," I replied.

Jay grabbed Tillie around the waist and licked her lips. "I'll come over later this week to pay you for your work," he said. "Thanks."

Tillie groped the front of his pants. "Thank you, baby."

Walking to the car, Jay put his arm around me. "Sorry about that, Sam," he said. "Tillie's a little outspoken sometimes."

"It's okay," I said. We got into the car. "Are you going to... do you fuck her?"

"Yeah." Jay sounded matter-of-fact. "She's not a girlfriend or anything like that. We just hook up once in a while. There are a few women like that in my life. Does it bother you?"

"It bothers me that you and she kissed and groped like that in front of me right after you asked if you could fuck me."

"It doesn't mean anything with Tillie. It's just a good time." He put his hand on my leg. "With you, it will mean something, Sam. You were always so sweet when you were a kid. I used to joke with Randy that I wished you were a few years older. I'm glad I walked into that store the other night and found you there. I'd like to see more of you. Not just for fucking, though I do hope that'll be part of it."

"But you're still going to be with Tillie and the other women you mentioned."

"Yeah, I probably will. I don't do the monogamy thing, Sam. You don't have to either, of course."

"I'm still a virgin, and you're already talking about me doing it with other people?" I did not like the way this conversation was going. "What kind of person do you think I am?"

"I think you're a woman, and I think you're going to enjoy what we're planning to do when we get to my place." He put his hand on my leg. "Sam, don't get upset. We don't have to do anything at all. I could take you home right now, and we can just forget it. You don't owe me a thing. I'm glad I contributed to your new look, and I hope you and I can be friends." He slid his hand toward my crotch, pushing up the hem of the dress. "But I hope we can be more."

His hand had the same effect it had had at Tillie's. I wanted to lose my virginity, and I wanted Jay to be the one to take it, no matter what- or who- else he did. Talk about seeing other people could wait; right then, all I cared about was finishing what we'd started. "All right," I said. "For today, at least."

We got to his apartment building and went inside. Jay's studio apartment was on the top floor, with a great view and modern furnishings. "This place is beautiful," I said.

"Yeah. I make a decent living."

I remembered what Randy had said about Jay being into drugs, and wondered if that was the kind of living he meant. But I pushed the thought away. "That's good."

I stood in the middle of the floor, not sure what to do. Jay put his arms around me. "How far have you gone before?" he asked.

"What do you mean?"

"Have you ever had oral sex?"

"No." I wasn't completely sure how it worked, other than descriptions I'd heard in the locker room.

"Have you ever touched a guy's cock? Or had a guy put his finger inside you?"

"No. I told you, I've never had a boyfriend."

"Have you ever had a guy's tongue in your mouth?"

"No." I was ashamed to admit that I'd never even had a basic French kiss.

Jay smiled reassuringly. "It's okay. This is going to be more fun than I thought, that's all. This is how you kiss."

He pressed his lips against mine. After a moment, his tongue found its way into my mouth. I moved my tongue against his, hoping I wasn't making too much of a fool of myself. After a few moments, Jay broke the kiss. "Damn, Sam, for someone who says she's never done that before, you're very good at it!"

"Thanks. It was nice."

"More than just nice." He brought my hand to the bulge at the front of his pants. "Feel how hard my cock is?" he said. "That's from that kiss, Sam. You did that to me."

"Can I see it?"

"Of course you can. But only if I get to see you again. Take off the dress."

This time, I didn't hesitate. I pulled off the dress and carefully set it on a chair. Jay took off his clothes and stood in front of me. For the first time in my life, I was seeing a naked man. And he looked fucking hot!

"Take off your panties, babe," he said. "If I'm naked, it's only fair that you should be."

I took off my underwear and held my breath. Would Jay like what he saw? He ran a finger through the curls of my pussy hair. I shivered as his touch brought more wetness. "It's been a while since I've been with a woman who didn't shave down here," he said. "I'll show you how to shave, but for today I think I like you this way." His finger slid lower and touched a spot that made me gasp. "Do you ever play with your clit?" he asked.

"No." I'd put my finger inside myself a few times, but I hadn't even realized I had this little nub that Jay was touching. "I think I'm going to start, though."

"Sit down," he said.

I sat on the couch. He knelt between my legs. "I was going to have you play with me and suck me, but I think I'd rather do this this time," he said. "I'm going to eat your cunt, and then I'm going to fuck you. If you want me to stop, tell me now."

I shook my head. "Don't stop. But can I touch your- your cock before you fuck me?"

"Sure, babe." He stood up. His shaft stood up against his belly. It looked around seven inches long, and seemed too thick to fit in me. I tentatively reached out and stroked it with my fingertips. "You don't have to be so gentle with it, Sam." Jay took my hand and wrapped my fingers around his cock. "That's the way. Squeeze it. Move your hand up and down."

I did as he said, and was rewarded with a moan. "That feels so good, Sam," he said. "Do you like doing it?"

I liked the reaction I was getting from him. I felt powerful knowing that my touch turned him on as much as his did to me. "Yes, I like it."

"Good." He took my wrist and pulled my hand away. "That's enough. I want to taste that cunt of yours."

A shiver of excitement went through me at his use of that word. I'd been taught that it was the worst word anyone could use, but it aroused me to hear it from Jay. "Go ahead," I told him.

He knelt again and bent toward me. At first just his tongue touched my clit, then he sucked on it. "Jay!" I cried.

As he continued to tongue and suck my clit, something built in me. Then he slid his tongue inside me, and I exploded, crying out with no words. He looked up at me and smiled. "Is that the first time you've ever cum?" he asked.

I nodded. I wasn't sure I could catch my breath enough to speak. Finally, I said, "That was unbelievable! I never knew it would feel so good!"

"And that was just my tongue." He stood and pulled me to my feet. "Your first time should be on a nice, comfy bed. Are you ready for my cock?"

I was so wet, I could feel it on the insides of my thighs. "Yes, I think so. If you're sure your cock will fit."

He laughed. "Your cunt will stretch, Sam. That's how it works. It might be a little uncomfortable at first, but then you'll get used to it, I promise. Lie down."

I lay on my back on his bed. He took a small packet out of the drawer of his nightstand. "I assume you aren't on birth control, so a condom's needed." He put the condom on and lay on top of me. "I won't lie to you, Sam. This is going to hurt at first. But if you relax, it'll be easier, and I'll be as gentle as I can."

"Okay." I shifted beneath him. "I'm ready."

He pushed his cock partway into me. I gasped as my pussy stretched to adjust. He lay still for a moment, then thrust hard. I felt a sharp, tearing pain and realized he was all the way inside me. I was no longer a virgin.

Tears came to my eyes from the pain. Gently, Jay brushed them away. "Are you all right?" he asked.

I nodded. "It hurt, but it doesn't as much now."

"Good." He slowly moved in and out. "How does that feel?"

"Amazing!"

"I agree."

He picked up the pace. Soon I felt another orgasm building. "Jay, I think I'm going to cum again!"

"Do it, babe. Let me feel your cunt on my cock when you cum. And then I'll cum too." He lowered his voice. "Cum for me, Sam."

And I did, my pussy contracting, squeezing his cock. Jay grunted and lay still. "Fuck, Sam, that was one of the best fucks I've had lately," he said. "How do you feel?"

"Sore, but soooo good," I replied.

"The soreness will let up." He kissed me softly, tenderly on the lips and moved off me. "I definitely want to see you again, Sam, but right now I'd better get you home. Get dressed."

"Oh, my gosh! Jay, we left my other clothes at Tillie's!"

"Then I guess you'll have to hope your parents aren't home, or figure out a way to explain it all to them." He grinned. "That's if they even recognize you. Go ahead and put that dress back on. I won't rip it off you this time."

We dressed, and he drove me to the corner of my street. Before I got out of the car, he pulled me close and kissed me. "I'll see you soon, Sam," he said. "That's a promise."

"How will you get in touch with me? You don't have my phone number, do you?"

"No, but I have ways." He unlocked the doors. "See you around."

I got out of the car and watched as he drove away. Then I headed down the street to my house, walking slowly because of the soreness between my legs. I couldn't wait to see Jay again.