Flirting with your boyfriends best friend
“He just won’t do it to me.”
“Why!?”
“Because it hurst her dummy.”
“But I want it.”
“Even though it hurts?”
“Yes!”
“It wouldn’t stop me!”
“Will you do it to me then?”
“Haha, well, umm, well…”
That’s how the conversation started, something between three friends that none of them would ever forget.
It was the end of a night out, in their last year at university.
The couple Moss and Tera were hanging out with their old friend Shelby. He was a good laugh and always got the rounds in. Rich parents. They had gotten around to talking about anal sex.
Tera was sitting on Moss’s lap, with her long bare legs, wearing a very short skirt and tight crop top, sitting on Shelby’s lap. He was rubbing her bare feet. It was normal. Moss didn’t care. He was cool with that.
“You realise your friend has a raging erection pushed against the sole of my feet?” Tera said, holding her boyfriend’s hand.
“And why wouldn’t he?”
“You mind if I kick him a bit?”
“Kick him?” Shelby said with a laugh. “How is kicking sexy? What kinks are you two into?”
“I mean kicking like this.” And she flicked his clothed dick a little with her painted toenails. Then curled them around the head and began to rub, before bringing in the other foot to slide up and down the very obvious protrusion of his erection.
“Oh, god yeah. I get it. Fuck yes I get it. This is my kind of kicking!”
“Ohhh loooks like my boyfriend likes me touching Shelby, his dick is sticking right into my ass now, hard as iron.”
“Bigger than me?” he gasped.
“Nah, or I’d be dating you, right?”
“Very funny,” Moss said, grinding himself up onto his girlfriend, thinking what a little slut she was, imagining her sucking down on his dick while he fucked her doggy.
“You going to get it out?” Tera asked her friend as she tightly squeezed both feet on either side and moved them up and down like it was her pussy or a hand.
“Yeah, yeah, I will. I’ll do it when you let go for a minute. Don’t let go, though.” Shelby couldn’t be sure she wouldn’t just be messing with him and wouldn’t just remove her feet and not put them or anything back. Like those lush lips.
“Why don’t you come give me your mouth while Moss grinds that dick right up your beautiful, sexy little bottom.”
“Anal?” Tera said.
“Why?” Shelby said, “You don’t do that?”
“Oh no, I would but…”
“But?”
“He just won’t do it to me.”
“Why!?”
“Because it hurts her dummy,” Moss said
“But I want it.”
“Even though it hurts?” said Shelby
“Yes!”
“It wouldn’t stop me!”
“Will you do it to me then?”
“Haha, well, umm, well…”
Moss was really grinding his dick into her now. He was practically fucking her arse through the little skirt.
“Looks like he wants to do it now, though,” Shelby said.
“I really don’t. I’ll bend her over and fuck her pussy while you do her mouth.”
“No!” Tera jumped up. And then swapped over, sitting on her friend’s knee and putting her feet into the lap of her boyfriend. “Maybe I don’t want it in the cunt tonight. Maybe I want it up the ass.”
“But you scream when I try to get it in? Even when I put a finger in you’re like no no no no!”
“And I tell you to ignore me.”
“How can I do that?”
“Easy, don’t think about what I say or do, and just do it. You are stronger than me, right?”
“Yes, I guess! Haha, I’m not sure. But point is when a girl tries pushing you off you don’t say ‘no dear, not until I’ve finished’ there’s a word for that.”
“Damn it, babes, I’ve told you that’s just how I’ll cope, but I want it. I’ve said yes. Look, you have a witness.” Shelby put his hand up, and then when he put it down again, it swung inside her crop top and began to fondle her small, pert breasts.
“See, Shelby will back you up in court!”
“Oh fucking funny!”
“You don’t mind him touching me, do you. He’s very hard. I think he needs me.”
“No, why would I mind. You’re an independent woman. You’re still touching me too, so cool.”
“Yeah, and I know I want to take a cock in my ass. Just to know how it will feel.”
“It’ll feel bad!”
“Yeah, for a while. The first time, the second time maybe, but I don’t know, I have friends who love it. They love it in porn. And you know if you twist my nipple and make me scream, I cum so hard from masturbating out the pain, right?”
“Yes, true!” said Moss.
Shelby twisted her nipple. She wasn’t wearing a bra. The outfit and the upstanding quality of her boobs meant she really didn’t have to.
“Oh god Shelby, that’s so hot. You know I’m not touching myself, though. It’s going to hurt. Hurt…”
“I don’t mind hurting you, babes, if it’s what you need,” said Shelby as he pulled her small hips hard into his crotch, and Tera lost her feet’s grip on her boyfriend’s dick, which he had now gotten out for all to see. He stroked himself.
Tera pulled her skirt right up and found a way to get her hand on herself to begin rubbing. She wasn’t wearing any knickers. She never did. Five different guys had fingered her that night. Her boyfriend only knew about three of them.
“See you bro here don’t mind hurting me. If I say no or push him off, what’s he going to do?”
“I’m going to hold you down and not listen to a word you say.”
“Really, Shelby? Really? You’ll do it will you? Really do it? I just need breaking in. Moss can’t hardly get a fingered up.”
“God, you must be tight right!”
“She’s so tight,” Moss said stroking faster. “I’ve never felt anything so tight. Like I have fucked ass, but I can’t even finger hers. And I’m big remember!”
“Yeah, Shelby, you might fit me better!”
“Oh, thanks!”
“But you’ll do it? You’ll give me anal? A painal? You’ll push it up and make me take it. That’s all I need. I just need my virginity gone.
“She’s not been a virgin for a decade!” her boyfriend laughed.
Tera kicked him playfully and stuck out her tongue. “You know what I mean. I need it taking the other way. Then you’ll do it to me, Moss? I really want you to do it to me. If I’m not an anal virgin anymore? If I show I can do it? Will you?”
“Sure,” it sounded like a funny thing to say. If his best friend forcibly fucked his girlfriend’s ass and made her take it, however much it hurt, then he would do the same. Crazy world! But then sex is always a little crazy…
“Ok, get that little fucking skirt off and lie flat on the floor,” Shelby commanded. It seemed he’d had enough of waiting around. Yes, he was ready to do it.
“Lube?” she said.
“Fuck no.”
“See Moss, your best friend really is a terror. He’s going to do me like you never seen anyone done. Don’t stop him will you?”
He shook his head as he gripped his other head even harder.
“I have other ways to lube up a pretty girl’s asshole,” and with that, Shelby pushed her off his lap and pulled his dick out through his pants. For a moment, with her lying face down on the floor of the lounge and with her skirt now off and her ass bare, facing him, it looked like he would simply plunge in and get it over with quickly. But he didn’t go straight in.
He flopped to his knees between her legs and bent his head to taste her. He pushed his face between her ass cheeks and licked. He licked for a long time and poked his dick against the strong guard to her back entrance. She moaned and squirmed on the floor like she was learning to swim on dry land, but she didn’t attempt to touch herself. She had already decided that this was going to be as bad as it could get. That for her first time, she would feel it as it was, however bad it was. Plus, her naughty side kind of wanted to make her boyfriend suffer a little watching it, from not being the one doing it.
She had had men lick her ass before, but none with as much enthusiasm and with as many precise and quick licks as this. It was heaven. His tongue was so still between her ass cheeks that she thought it’s pointing in at her might actually make it penetrate. Was that even possible? To lick the inside of an ass? Even on a normal woman.
Then he sat up, his cock still hard and proud. Her boyfriend got a kick out of looking at it. For a minute, he was jealous that it was her lying there about to take it. He’d never thought such things before…
He looked down on her and paused for a moment before prizing her tight little round ass cheeks apart and taking more time to admire the glistening of his saliva there. She stretched her head around to see if this was the moment he would lean forward and force it up her. Not yet. Not quite.
He looked at it and then spat. He spat straight at her asshole. He was a very good shot! She felt it hit her most sensitive spot where his eager tongue had been going at her a few seconds ago.
Then he let more saliva fall from his mouth and puddle in her ass. She was quite wet there now. It wasn’t as good as lube would have been, but there was no way she could claim he’d fucked her while dry. She wondered if she could take being fucked while dry? I mean, that would be hard to take, and would a guy even enjoy that dryness?
Who was she kidding? She had watched so much painal porn that she knew the more a girl screamed, the more she pushed back or tried to wriggle free, the more turned on the man got. But that was porn. That might have been staged. They probably always used a ton of lube. That’s why she always went for the more amateur stuff, things that were never meant for public consumption. People who weren’t porn stars, to see how it really worked.
The looks on some of those lovers’ faces, anguish, aggressive lust. Really, how could she expect her sweet, understanding, caring boyfriend to understand her need for that? Having a friend do it had to be better. Maybe she should have just gotten a complete stranger to take her for the first time. Would that have been even better? Does it have to be someone who doesn’t care about her at all?
Oh no! Shelby would do just fine!
He was working a finger up her resistant hole.
