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By TessMackenzie (edited)

Billie had been picked up by Seth, or he’d been picked up by her, or someone had picked someone up. Billie didn’t care anymore. She was at home, with Seth, tipsy, and achingly horny.

She was kissing him standing in her bedroom doorway.

In the doorway because they seemed to have stopped moving, still in the hallway. Even though the bedroom light was on, and both the coats were off, they didn’t make any further progress towards the bed. She kept kissing, and didn’t really care. Maybe he didn’t like beds. Maybe he wanted to fuck her here.

They’d been kissing all the way home. He’d been stopping to grope her, to kiss her neck, to grind her through her clothes. She wanted him badly. Really, really badly. She needed him so much she almost couldn’t stand it.

He seemed to be taking it slowly, though. Taking his time, kissing a lot, and touching her everywhere that wasn’t between her legs. He was acting like it was still in doubt. Like she might say no. Like he still needed to work at it, to get her. He didn’t need to work at it. She was sold. She was in. She thought she was already making that pretty clear.

She kept kissing, and moaning, and rubbing his arms, hoping he’d speed things up. Wondering if perhaps this was just his thing, his trick, part of a plan to make him a better fuck. To take it slow, make her so horny she forgot to breathe, and then fuck her until she couldn’t think.

Maybe it was that. She’d been going along in case it was, and in case it worked. Even though she was getting impatient. Even though she was getting quite an urgent need to fuck.

She started undressing while they stood there kissing. She undressed completely, stripped in the dark hallway, while he looked at her in the light spilling out of the bedroom. He sucked on her tits, and grabbed her ass, but still didn’t go into the actual bedroom.

She decided this was getting silly. She was also starting to feel a bit obviously naked when he wasn’t at all. She started moving, pulling him in the direction of the bed. She’d almost decided that she was just going to start without him. Whatever might be involved in that.

Seth was hot. That was why she was here with him. He was hot, and cut, and she’d known that before they left the party because she’d had her hands all over him there. Feeling the hardness of his body, and the ridges of thickness where muscles lay, and the tight solidity in his arms as he moved and his muscles tensed. She wanted that. She’d been feeling him all night. After a while she took off his shirt, and saw what she’d been touching all evening. Saw and liked. A lot. She kept kissing him, sliding her hands over him, glad to be feeling someone warm and alive and sexy, and having someone there wanting her.

She was glad she had someone here. She needed to be touched as much as she needed a fuck. She was starting to get impatient to start. She reached for his pants, and started trying to take them off, but he sort of shifted and got free, then went back to kissing her. That was a bit odd.

She tried again, and moved away again. Then he knelt in front of her, while she was still standing, and slid his hands up her thighs, and pressed his mouth forward, and started eating her out while she stood there. So much for his plan of taking it slow, she thought. If he’d ever had one. She put her hands on his head and enjoyed it.

After a while, because her knees were trembling, she sat down carefully on the edge of the bed. He was really quite good. She sat there, and held onto his head so she didn’t just slump backwards onto the bed. Held on, and reached down for him occasionally, and tried to get him to stand up and take off his clothes.

She wasn’t really trying very hard, but even so, it was odd he didn’t seem to want to. He seemed reluctant to stand up, and undress, and get on the bed with her. The head was good, and she’d been thinking she could maybe turn around so she could reach him too, so they could sixty-nine, or something. And make it last longer.

Each time she tried to organize that, though, he moved slightly, shifted away so she couldn’t reach him. It was confusing. In the end, impatient, she just grabbed his arm, and held him there, and slid her hand down his tummy, towards his pants. That didn’t work either.

He actually shook himself free of her. Shook free, and pulled away, and said, “Just let me do you.”

“You are,” she said, puzzled. “But I can do you too.”

“I want to go down on you.”

“I want you to as well,” she said. “I really do. But, um, I don’t mind joining in myself.”

No answer.

“I mean, if you think I can’t do both at once,” she said.

Still no reply.

Billie leaned back, and looked at him. He seemed really uncomfortable. He looked almost embarrassed.

“What’s wrong?” She said.

Seth shook his head. He looked terrible.

He looked suddenly shy. Shy, and nervous, and like he might blush.

Billie was suddenly worried. She was suddenly thinking there must be something terribly wrong. That he’d already come, in his pants, without her noticing. Or something even worse. Surely if it was coming early, he’d just say. Acting like this, there must be something awful going on, and she’d completely missed what it was.

“Seriously,” she said. “What’s wrong? You’re scaring me a bit.”

After a moment, flushing, he undid his pants and showed her.

He had a small cock.

It looked smaller than a Twinkie*.

His body was big, and buff, but he had a small cock. She supposed that was why he put all his efforts into working out. It made a kind of sense. Billie stared at his penis. She wasn’t sure what to say. She almost said, “Is that all,” meaning is that all that’s wrong, but realized in time how awful that would sound. She stopped herself before it slipped out.

She almost said she didn’t care, that she didn’t mind, but he was obviously already upset about it, so he probably wouldn’t believe her. She also didn’t say that size didn’t matter, and she’d be fine. From the way he was behaving, it was too late to say that because someone had already told him it did. Someone who told him it did in a pretty direct and nasty way.

She almost said something worse, too. That she didn’t care, that she was here for a fuck and not all his insecurity and drama. But she wasn’t so horrible a person she’d do that, even if it was true. So in the end, she couldn’t think of a thing to say. There wasn’t anything that wasn’t either patronizing or mean.

In the end, she just bent down and put it in her mouth and sucked it, and that was probably the right thing to do. He sighed, and put his hands on her shoulders, and it felt like he was relaxing a bit. The muscles in his legs and tummy weren’t clenched so tight after a few moments, anyway.

Billie decided that was probably the best thing she could have done. She had condoms in the drawer beside the bed. The drawer nearest where she’d ended up sitting. She could reach, just, with him still in her mouth. She grabbed a bundle, tore one loose from the roll, and opened it to put it on him.

“Let me,” he said.

Billie slid him out her mouth. “I can.”

“Please,” he said, very softly. “Let me.”

The quietness in his voice made her stop. More than if he’d grabbed it away from her, or pulled her off himself.

“Yeah,” she said warily, and held it out. “Of course.”

He took it and started fiddling around. Getting it the right way around, not inside out, pulling it on.

Not rolling, pulling. Suddenly Billie understood. He was hard, but was worried he might not be big enough to fit inside it. She wasn’t even sure if that was possible, but she decided to leave him alone to sort it out. She lay backwards, and looked up at the ceiling, and tried to make it clear she wasn’t watching him.

After a moment he seemed ready. She sat up and kissed him. Kept kissing him, and pulled him over on top of herself, and said, “Fuck me.”

There was a bit of fumbling. Like there always was, with someone new, but it felt like they were both acutely aware of it now. Too aware. That was stupid. Billie hadn’t been in this situation before, but she could guess what would happen. It wasn’t like there was such a thing as too small to go inside her, and it wasn’t like anything inside her wasn’t going to make her feel something, even just her little finger.

She wondered if he knew that. That she would be able to feel it. If he’d quite thought through that fingering people meant, obviously, that they could feel things the size of fingers.

She suspected not. It was such a common joke, something even she, right now, suddenly couldn’t help thinking. He’d probably heard it too, and that probably made moments like this a lot worse for him.

She wondered if she should say something, then decided not. He seemed very self-conscious. So self-conscious that if she said a word, or even did anything that looked overacting, he’d probably stop. Any sighs and gasps and moans about how good he felt, anything at all that seemed like a fake.

Billie decided she ought to be careful. Which was silly, since they were going to be having sex, which she was planning to enjoy, so that meant she was going to be feeling something, and would probably want to express what she was feeling. But she was suddenly worried about making any noise at all.

This was really messing with her head.

Even now, as he got himself inside her. Instead of sighing, or helping, she just lay there, feeling awkward too, looking past his head at the ceiling, stroking his back gently, and waiting for him to get started. It felt almost like being at the doctor. Lying there waiting for something to be done to her. She almost wanted to resent that his issues were spoiling her hook-up, but she made herself stop. That wasn’t fair.

After a moment, he was inside her, and moving, and she was almost relieved she could actually feel him. Which was a horrible, stupid thought. She started kissing him again, and concentrating on that. As it turned out, she could feel him, and it wasn’t bad at all. He was kissing her well too, which made up for a lot.

He seemed to be keeping his hand down between them, though. She was about to say not to worry, that she’d do her clit if she needed to, then she realized why his hand was there. He was holding the end of the condom, so it didn’t come off.

Whether or not it actually would she didn’t know.

It didn’t seem likely, but they were fiddly little things, and she’d had them end up loose and up inside her before. She supposed she was glad he was being careful. Glad of that, and also a bit worried that he thought he needed to hold onto it. That he thought he wasn’t big enough to fill it so it fit properly. That seemed awful for him.

Suddenly she felt bad for him, and how complicated sex must be every time he had it. She thought of all the jokes about things not to say when a guy was inside you, is it in yet, and is that all, and that she couldn’t feel very much. She probably only felt kind towards him because they were having sex, and that always made her a bit huggy, but still. This wasn’t a good emotional place for him to be.

She tried to squeeze herself around him, to see if that made her feel more. Or made him feel more, or at least react if it did. It didn’t seem to change things very much. He was going pretty fast. In another couple of minutes he’d be done fast.

“Hey,” she said. “Slow down a bit. Enjoy it.”

He nodded, and did, but he still didn’t look at her. He was embarrassed, was avoiding her eyes. He was basically ashamed, even while his cock was inside her. While they were fucking.

She wasn’t sure if maybe she should try and help, because then maybe he’d feel better and fuck her properly. And take a bit more time about it. But perhaps it wasn’t her place. To psychoanalyse him while they fucked. Perhaps people had tried that before, and it hadn’t helped since he still had problems. So maybe she would only make things worse.

She thought for a moment. She felt bad for him that whatever shit he’d experienced in his life had made him like this. Not just feeling close because he was inside her. It was more than that. She felt really sorry. Her feeling that didn’t mean he’d want her trying to help, though.

She thought a moment more, and decided to risk it. If she made it worse, it didn’t really matter. They could just stop. And she’d probably never see him again, anyway. “Hey,” she said, but he didn’t look at her.

She grabbed his chin, and pulled his face towards hers, so she could see him. She reached down, and pushed his hand off his cock, and held it herself. Held the end of the condom, all plastic thin against her skin.

“It’s fine,” she said. “I promise. Don’t feel weird.”

He shrugged, but still seemed a little odd.

“I fucking promise,” she said. “It’s good. It feels good. Please don’t get upset.”

“Okay,” he said, after a moment.

“Can we try something?” She said.

He nodded.

“Let me turn over,” she said. “We’ll both feel more.”

For a second he looked like he didn’t want to hear that, but was glad to hear it too. Both at once.

She kissed him, and pushed, and said, “Let me up.”

He knelt and she turned around, got on her elbows and knees, and looked back at him. “Go on.”

He moved, knelt behind her. She reached back, steered him a bit. It wasn’t as easy to hold onto him this way, to hold onto the condom, so she let him hold himself. His hand was against her, pushing against her a little too, as he put himself in.

That pressure felt good.

He fucked her.

She reached down, and pressed against herself with her hand. He fucked her a bit faster, and she thought he was watching, concentrating on that now. As though girls wanking, for any reason at all, counted more than all the self-confidence issues in the world.

Billie hoped that was so. She hoped it might make a difference. She was glad to play with herself if it helped. She rubbed herself more obviously. She was sliding her hand down herself, reaching back, sliding it past his cock, along her lips, pressing everything together all oily and slippery wet. She was very wet. She didn’t know why. All the build-up, all the kissing on the way home, she was wet like she didn’t normally get. She had a thought.

She had a guilty, nasty, terrible thought that she ought never to admit to a one-night stand. Sometimes she liked her ass being played with. Even though she was usually too embarrassed to admit it. Her hand was slippery, and his hand was too, and the one he was using to hold the condom was slithering around as they moved, had slid over her ass a couple of times, shamefully good.

By accident, she was sure. Completely unintentionally. But she wanted it to happen again. She didn’t quite know how to ask. She knelt there, and wondered, and suddenly wasn’t paying attention to the actual sex she was having, because she was too busy thinking about the sex she wanted to have.

She really liked a finger up her ass during sex. She always liked a finger. A finger was really nice. She didn’t like actual anal sex very much, or very often, with a whole, thick penis stretching her, being shoved into her.

But he didn’t have a whole, thick penis.

He had a smaller penis, and it might be the right size to feel very good.

She wasn’t sure if she should suggest it, if she should just be honest and say what she wanted to try. She wasn’t sure that even asking him to fuck her in the ass might not just put him off her. Either because he didn’t like it, or because it would be obvious why.

Because he was small.

He had a small cock.

That was why.

She felt terrible even thinking that. It was completely awful to be even considering this. But he had what he had, and she liked what she did, and she suddenly wanted to try.

“Hey,” she said. “Could we do something else?”

“Yeah. Of course.”

She felt too embarrassed to say it. Because she was actually asking, not merely agreeing when someone else wanted to do it to her. Because it was pretty filthy to say you wanted it done to yourself.

So she didn’t say. She took his hand, and put it against her ass. Above his cock. So it was clear what she meant.

“Would you be into that?” She said, still not looking at him.

Looking down at her pillow. Waiting for an answer. Still a little ashamed. Like him, she supposed. Now they were even. He hadn’t answered, and she was worried what he was thinking. She turned around, and looked, self-conscious. He was embarrassed to be inside her, and now she was embarrassed to have him there. He was looking at her, and looking surprised. Not horrified or anything, but surprised.

“Sorry,” she said. “We don’t have to.”

“No,” he said. “Sorry. Of course. I mean, sure. If you’d like.”

“You don’t mind?”

He shook his head. He’d stopped thrusting into her while they talked.

“You’re sure?” She said. “You seem a bit… I don’t know. It’s not too weird?”

“Not at all.”

“You’d really like to?”

He grinned. “Ah, fuck yes.”

So maybe he hadn’t thought of the size thing after all. Maybe he never would, since it wasn’t his ass the cock was going up.

Maybe he just thought she was an everyday kind of pervert, and it was unrelated to him. She wasn’t sure how she felt about that.

She had lube in the drawer beside the bed, with the condoms. She reached over, and got it, and squeezed a little out, onto herself, and onto his hand.

“Not too rough,” she said.

Even with a cock that size, she didn’t say, but she thought he understood. He got embarrassed again, but was interested too. He rubbed her anus slowly, sliding his finger over her, inside her. Moving his cock inside her at the same time. She relaxed, and felt him slide his finger in. Felt it wriggling, and pushing, pressing down on her, on his cock, through her.

She pressed her fingers against herself too, moved her knees apart so she was draped and spread and ready. She felt relaxed. She felt readier for this than she ever had before.

“Okay,” she said, after a moment.

He moved his cock. Against her, then inside her. Inside her just like that. With no effort for her at all. Like a finger or a vibrator going inside, with none of the worry she usually had, about size and being hurt and having to do everything carefully. This wasn’t like anal normally was at all.

It wasn’t complicated. It had never been like that for her, not there. Uncomplicated felt good. Uncomplicated felt really sexy. Compared to how it normally was, a bit of a fraught performance piece. He just felt good. She couldn’t quite get over that. Not sore, or stingy, or like he was lunging too deep. She just felt filled, with him completely inside her, and unspeakably, overwhelmingly good.

He fucked her. He fucked her like he ought to have been fucking her all night, without all the complications and worry. And she knelt there, and sighed, and pressed her fingers into herself as he did, and felt him. It was very good to try. It was interesting to try. And his size did matter. It made it a lot easier. It was like being fucked, just fucked, but with a finger, not a cock. It was anal without all the worry that usually made it too much trouble to do. Even though she liked it.

“I’m close,” he gasped after a while.

“Me too. Hold on.”

“I’ll try.”

“Hold on,” she whispered. “Please.”

“I am.”

“Hold on,” she said, squeezing around him, rubbing herself harder, and aching for needing it.

She’d never cum from anal before, not being fucked in the ass with a cock anal, and she desperately wanted to. She needed to. “Hold on,” she whispered a last time, and was suddenly there.

It was deeper and fuller and thicker than a normal orgasm. It was like the beat of a big bass drum, not the tingle of a cymbal. She sighed, and pushed back onto him, and went completely still, just feeling it. She was glad he’d held on. She was unspeakably glad. It must have been close for him, though. He started right after she finished.

He groaned, and told her she felt great, and made a bit of a performance of it. He seemed to be careful letting her know he appreciated it. As you did for someone who let you come up her ass, Billie supposed. Or perhaps he really felt all that.

She knelt there, and waited until he was done, and then went and cleaned up. She sat on the toilet to get a moment away from him. She felt self-conscious again, a bit embarrassed she’d come from doing that. Then she decided she shouldn’t feel that. The embarrassment should be his as well hers. He’d done it to her, as much as she’d had it done.

After a moment she realized she’d completely forgotten about the size of his cock. She came back, and sat on the edge of the bed, and looked at him.

“That was good,” she said.

He shrugged, like she was only being polite.

“Listen,” she said, and took his hand. “Just so you know. You should tell people more about you. Tell women, and explain they could try anal.”

He went pink, and wouldn’t meet her eye.

“I mean it,” she said. “I wanted to, but not the getting hurt doing it. Do you understand?”

He looked at her for a moment, then nodded. Then looked away again, still mortified.

“I’m completely for real,” she said. “I promise. The rest doesn’t matter. That we can that, like that… I don’t know. I mean everything else doesn’t matter.”

He didn’t answer, so she let go of his hand and started getting dressed. Her clothes were all still out in the hall.

It was a hint, and he understood. He stood up too, and found his pants.

“Thank you,” he said, after a while.

She nodded, and didn’t say anything more. She thought she’d got through. She hoped she had. It might make him feel better. He stayed for a while, and they talked, like they had been at the party. Billie got his number before he left, and he seemed to want to see her again. She wasn’t sure if she would. She felt awful because of that. Shallow, like a horrible person. His size mattered, but it didn’t. His insecurity about it mattered more. She decided to wait and see how she felt in a few days.

The End.

 

*For international readers a Twinkie is an American cream-filled cake treat 4 inches long, and 1.5 inches wide.