Learning Lessons 1: Date Night / Chapter 2

Jess was quiet for a while, flicking her wrist on him, her thumb on the underside of his little cock, three fingers along the back, hidden in his pubic hair. “Don’t you think it’s so unfair? I mean, you were born with this tiny little penis and there’s another man out there who can drive a woman crazy with something two, maybe three—maybe four times what you’ve got. Wouldn’t it make sense if everyone was kind of the same? When you see the ends of the spectrum, that’s when you really see the difference in sizes. You’re at the smallest end, so, so tiny, then he’s got this big, fat beautiful thing. You just can’t keep your hands off it.”

“It is so unfair. I can’t even please my beautiful wife.”

“That’s all right, we’ve got someone who can now.”

“Are you going to fuck him again?”

“I can’t wait to. You’re not going to try to stop me, are you?” Her hand was on him. She had complete control. He looked at his beautiful but now very dirty wife. She had an innocent face. So pretty, with fine features and a long beautiful neck. Her eyes were big and expressive, the lightest crystal blue—when she talked, people were rapt, lost in her gaze. She was so kind and so warm—no one who knew them would ever imagine she would go out on a date with another man, fuck him in their minivan, then humiliate her husband with some of the dirtiest talk you could imagine while she stroked his small cock. She could get away with anything with that sweet face.

“I want you to get what you want.”

“I’m serious. I wanted to go again right away, but the whole thing felt so odd when he came. He buttoned himself up and got out of there. I would have gone all night with him and that big, thick penis.”

“He got what he wanted.”

“He doesn’t know what I want. Not like you do.” She whispered in his ear, her fingertips gliding over his sensitive tip.

“Oh, God, Jess, I wish I had what he had.”

“I do too. It’s all right now. I think we’ve found someone who’ll play along with us. And I want to go back to that well every time I get thirsty.”

“Will you let me watch you next time?”

“I might. I’ll ask him. If he doesn’t like it, you’ll just have to sit at home alone again and think about me with him. Think about me crying out when he forces that big club into me. Think about how he’s making me come, over and over again.” She was watching him, her face so close to his, watching him tremble on the verge of a monstrous orgasm. She was toying with him, building up something that was going to make him crazy.

“I really want to watch you next time.”

“You know what I want?” she said. “I want to give him a hand job while you watch. Is that weird? I don’t know why. I’d just love to have you watch my hand struggle around that big thing. I want to make it last too, a nice, long hand job, and I want you to watch me make him come. I want you to see what I can do to him.” She was gasping as she whispered into his ear. He could tell she was turning herself on as she spoke.

“God, Jess, you’re making me crazy,” he said, and he stopped her hand. He was so close, and he didn’t want to do it like this, sitting on the couch with her hand stroking him under a blanket. He needed her, needed to be inside her. “Please, Jess, I’ve got to be inside you.”

“Don’t you think I should clean up first?” she said.

“No, I can’t wait, Jess, please…”

“You want to fuck my dirty little hole?” She frowned at him, pretending to be disgusted by him. His heart stopped when she used those awful words; couldn’t believe they were coming out of his pleasant, mild-mannered wife. She was the Third Grade Teacher of the Year, three years in a row now.

“Please, Jess…”

She was already lifting her skirt, though, slowly, seductively. He watched it rise up her tan, oily legs. She stopped at her thighs, making him beg. Then quickly revealed it. She wasn’t wearing any panties. She was shaved bare specially for her date and her lips were sat out from her, still dark and engorged, still looking damp and used.

She whispered to him, “I’m a little sore, but I don’t think you’ll hurt me.”

He couldn’t take it. He put himself over her, his throbbing cock headed between her legs. He brought the blanket with him, throwing it over his shoulders like a cape.

“Wait, Petey, no, no,” she said, and she put her hands on his chest to stop him, keep him at bay.

“Come on, Jess.”

“No, not down here, Pete. We have to go upstairs—the boys…”

“Yeah, yeah,” he said, hoping he’d make it up there. He was on the edge, so very close.

“Are you sure, Jess? They won’t come down, honey,” he said, trying desperately to convince her. But she was already moving, getting herself out from under him, sliding along the couch.

“I’m sure, Petey,” she said. She got up and headed for the stairs and as she went she slowly lifted her skirt for him and he watched the tops of her thighs revealed slowly, then the tight jiggle of her cheeks as she strutted through the arch and headed for the stairs. He followed, and she let him watch her rump move and work as she sashayed up the stairs.

When they got in the bedroom, she locked the door behind them, jiggled it to make sure it had taken. He went to put his arms around her, wanted to take her down right there at the door and finish this on the floor with his pants around his ankles and her skirt hiked up.

“Get a condom,” she reminded him. Shit. He went to the night table and yanked the drawer while he watched her; she didn’t take her clothes off. She lay on the bed, feet still on the floor, and pulled her skirt up at the front and he could see the sheen on her shaved mound in the lamp light.

“Hurry up and get this over with,” she said, teasing him, “I’m exhausted and I want to go to bed.”

His hands were shaking with anticipation, ripping the foil open on his condom packet. He pulled it down his shaft while he rushed to get himself between her legs. She watched him and she was grinning.

“Can’t believe you’re going to waste my time tonight with that tiny thing after I told you I just took a real man…”

“Oh, J-Jess,” he stuttered, barely able to think he was so out of his mind with lust. He slid himself inside her. Maybe he imagined it, but she felt stretched, like he made no impact on her insides and he slid all the way up inside her with no friction. But it wasn’t like he would normally spread her apart.

#

Jess felt her husband enter her. His penis wasn’t terribly big. He was the smallest she’d been with, but she felt it and it worked, too. His little penis had delivered two of the greatest things in her life. It had given Jess her little boys; her Andy and her Pete Jr.

It was Pete who was the first one to mention his size. The first one to bring up the elephant in the room. She’d always known it was small, but she loved him. Maybe a few times she had thought to herself that she wished he were a bit bigger. Not huge or anything, just maybe average.

He’d brought it up to her while he was inside her one night. She was horny and turned on and he asked her if he was too small. He kept making love to her, sliding it in and out of her. She told him he was fine. Pete turned it into dirty talk. He told her to be honest, and he was working with her, teasing her. She felt almost drunk with ecstasy that night. He’d gone down on her and he was so very good at that. He had her primed. Then he was inside her, urging her to say dirty things about his size. She felt safe. So she told him the truth. The truth didn’t hurt him. He liked it. She found, too, that she liked to say it to him. She liked to tell him dirty things if he wanted to hear them.

She told him he was the smallest, and that was true. She told him he was unsatisfying, which could also at times be true. He asked her about her other boyfriends. That was odd at first, difficult to think about, let alone talk about. They weren’t just disembodied penises to her; they were real men that had been in her life and for the time she was with them, they meant so much to her. Some of the breakups were not so fun.

But it brought her back to Brad Evans. While her breakup with him broke her heart, he was truly a standout in the sack. She remembered her times with him quite fondly. Naughtily, maybe. The first time she’d been with him, she pulled his penis out of his underwear and she laughed. It was the biggest one she’d seen. She was only twenty at the time, but she’d seen a few. She loved that thing he had, but she also loved him and that was a big part of their lovemaking. Still, he was big, and he also knew how to use it. So she told Petey all about him, his penis and what he would do to her with it, and how much she loved it. She couldn’t believe how much it turned her on to relive those stories, to tell Pete about them; and how strangely enjoyable she found humiliating Pete was.

Pete was pumping himself into her urgently now. Her story had him on edge and she knew he wouldn’t last a minute. “I wish I had saved his used condom, Petey. We could slip it over your little penis and show you how it would slide right off you.”

“Oh, ah, Jess…”

“Petey, I can’t stop thinking about how good Tyler felt—how big he was…”

She didn’t really care about size—not all the time, at least. Not enough that she wouldn’t have married Pete. A big one was nice when you got it—but a little one wasn’t the end of the world. There was something about humiliating Pete, though, that really turned her on. She hated that it did. She was a good woman. A good wife. People respected her. If anyone were ever to hear the awful things she said to her husband, they would be mortified. She would be mortified. She could never show her face again. It would be so humiliating. She got a tickle from saying the absolute worst things she could think of. Things that should hurt him.

She rubbed Pete’s back, whispered in his ear, “Hurry up and fill that little snug-fit condom, Petey—”

“Oh, God, Jess…”

“Petey, baby, do you know how small you feel? You feel like Tyler’s finger…”

“I’m going to come, Jess.”

“Come on, Petey, Tyler wore me out. I just want to go to sleep.”

He shuddered as he came, drove himself into her again and again as deep as he could get it. His face contorted, but he was silent. He finally buried his little thing into her, held it, and she could feel it pulsing inside her. She knew she had really done it for him, had really sent him over the top. His body was racked with sobbing breaths, then he collapsed over her, held himself up on elbows so he wouldn’t crush her.

About a year ago, he said he wanted her to be with other men. She wasn’t incredulous at the outrageous suggestion. It seemed like the logical next step. It was crazy, but in a strange way, it wasn’t that crazy. She never imagined she would ever be able to do it. Pete told her he fantasized about watching her with another man—one who could really give it to her. She’d said, No. Eventually though she let that idea leak into her subconscious and then gradually it became part of their lovemaking. Dirty talk about the things another man would do with her.

Thinking about it, while she was with Pete or maybe alone at night with her fingers between her legs, became an exciting proposition. The thought of being seduced by another man, or seducing one on her own, became a solicitous distraction. One she looked forward to fantasizing about, but not something she believed they would ever make happen. But she made up rules any way. Things that Pete would have to concede if she were ever to do it. That was just part of the fantasy, too. But every time she made a rule, or came up with a man she’d like to sleep with, the whole thing became more and more real.

“Oh, Jess, baby,” Pete said into her neck. He was hot and sweaty and he was still huffing. “You’re so incredible.”