Horny Stepsister Wrecks An Asshole - A Taboo Pegging Story

One of my Pornhub fans suggest I turn this first time pegging story in to a series.

In the story, a step Mom pegs her inexperienced stepson. I had planned to write a sequel for these two, I think the MILFy main character could definitely corrupt Max even further.

This taboo pegging is a bit different. No one here is particularly innocent. This is written with love to the subbie guys with big mouths.

All characters are of legal age

“Why are you like this? Can’t you just let it go?”

From his position on the floor, Ethan looked up at his stepsister.

Ethan was sure she was going to just laugh and move on from their bet, but he’d underestimated her. Now he was on all fours, entirely naked and Emma was showing no signs of showing him mercy. Her eyes glittered with cruelty and excitement.

“Let what go? This was your idea.”

Bending down, she puts a bottle of clear liquid on the floor in front of her stepbrother.

“Get yourself ready for me.”

“Emma come on…”

“It’s up to you. You don’t need to use lube. But you won’t like it if you don’t.”

Ethan picked the bottle up.

“You’re really going to do this? You’re not joking?”

“It was your bet.”

“I didn’t think you’d actually…”

Ethan blushed and trailed off.

Maybe the bet hadn’t been the smartest idea.

It had started off innocently enough, betting sweets, and then small amounts of money on darts. But this particular night Ethan had been drinking. Two beers had been enough for him to start pushing his luck with Emma.

He was the better darts player by a mile. Why wouldn’t he make such a wild bet?

“I bet I win the next round. If I win, you’ll give me the rest of your crisps.”

“Okay. And what if I win?”

“You won’t be winning anything, little sis.”

“But if I do beat you. What then?”

“If you win, you can fuck me up the ass. How about that?”

“Deal.” He was expecting her to laugh but there was something about her tone that sent a wave of unexpected excitement through him. His stepsister was competitive. He liked that about her. It was almost a shame she was so bad at darts.

And yet, three throws later and he was stripped naked in their garage looking at a bottle of lube.

“You made a bet. It’s time to pay up.”

Ethan remembered using the exact phrase the last time he won at darts.

“You’re loving this, aren’t you?”

Emma grins.

“It was about time I had some luck.” she says “Are you going to use that lube or am I going to lube you up too?”

“Okay, okay…” Ethan takes the bottle and begins rubbing the liquid on to his asshole.

“You’ll need more than that. I’m not going to be gentle with you just because you’re family. Make sure it’s all the way inside you.”

Ethan could feel his cock getting hard. The way she spoke to him so firmly made his inside swim with submissive desire.

“Like this…”

Suddenly, he could feel Emma’s fingers in his ass, rubbing his hole and pushing the lube inside. He gasps, but doesn’t pull away.

“Are you hard?” She asks.

“A bit. It’s a normal reaction to someone touching my ass. I can’t help it.”

“It’s normal to get hard about being fucked up the ass?”

“That’s not what I meant.”

“Whatever. Give me more lube.”

Ethan passes the bottle back to his stepsister, who empties a heavy amount on to her fingers. They feel small on the sensitive skin of his asshole, until she pushes them inside him. She is gentle, and it feels good.

“You’re relaxing a bit now. That’s good. Good boy.”

If Ethan wasn’t hard to start, he was now. On all fours, it was going to be impossible to hide if she checks. The rough carpet of the garage felt hard under his fingers. Thank God their parents were away on holiday.

“If you tell anyone about this, you’re dead.”

“I’m not going to tell anyone. But if I did, you would deserve it.”

When had she got so cocky? Had Emma always been this confident? Her fingers moved in and out of his asshole, making him more open.

“Okay. I think you’re ready.”

Smooth plastic pushed against his entrance and Ethan gasped.

“Where did you get that from?”

“I’ve been waiting for my step bro to make a stupid bet for a while.”

“What? You bought a strap on to use on me?”

“I’m joking. Relax loser.” Ethan could hear the smile on her lips “I’ll try and make it good for you.”

Emma puts her hands over his ass cheeks and pulls his hips backwards so she has a good angle. Then slowly, she begins to push the toy inside him with her hips, moving backwards and forwards. The first inch pops inside with only a little effort.

“Wow… The toy is going inside your asshole so easily. Have you been doing this often?”

Ethan was ready with a quick denial, but Emma adjusted her hips and the comment died in a noise of pleasure.

Of course, she was right. He’d always loved the feeling of filling his ass with a toy. He loved the feeling of it, how dirty it felt, and how good his orgasms were when he used one. The feeling of being stretched by his favourite anal toy as he fucked himself to porn was one of Ethan’s favourite pleasures.

“I know. You definitely have. But I bet you’ve never had this before.” She stroked his ass cheeks and pushed the toy even deeper. “You’d never have the guts to tell a girl you like butt stuff. That’s okay. It can be our secret.”

Emma reaches around casually and strokes his hard cock and Ethan gasps, trying to hide how turned on he is.

“Oh wow, you’re really getting off on this. I hope you’re not going to start losing at darts on purpose.”

“Are you done yet?” Ethan growls “I think you’ve made your point.”

“Nah. I’m going to make you cum. I don’t think my point is proved until I do.”

“What?”

“Am I not speaking English? I’m going to fuck you up the ass until you cum.”

“Why do you want me to cum?”

Emma begins to fuck the toy in to his ass in a firm rhythm, holding both his hips like he’s a submissive girl.

“I think you should learn not to make stupid bets. This might help you remember in future.”

“Emma I don’t want you to make me cum. You’re my stepsister. We have to live together and I don’t want things to be awkward…”

Her hands reached round again and Ethan’s sentence trailed off. The sensation was so good, and it was not going to take long before he had an incredible orgasm. He could feel it in his balls, it was going to be so intense, so big, so mind blowing.

But after he came, he would need to face his step sister had made him cum on the garage floor in such a humiliating way. A plastic cock in his ass, her little hands stroking and pumping his cock. He was so close to that situation already. Precum had started to leak from his dick and his body felt so good.

“You made this bet. You said I could fuck you in the ass. If you wanted to not cum, I’m sure you could hold back, right? If it was really so bad, your cock wouldn’t be so hard.”

Emma continued with her rhythm and Ethan realised vaguely that she had definitely done this before and the idea nearly put him over the edge. Why was that so hot, that his stepsister had claimed other men like this before? He liked the thought. No, he loved it.

He loved the fact he wasn’t the first one to have his sister’s plastic cock rammed into his asshole. What the fuck was wrong with him?

Emma continued working his cock with her hands, his asshole was so full, he was so ready to lose his load all over her fingers. And she must know. It was so terrifying how she knew he was into this and even more terrifying that she was clearly unafraid of exploiting it.

“Next time, I’ve got a bigger strap on.” She gasps “I’ll make you really feel it. You’re going to cum so hard you’ll see stars.”

That was it. There was no holding on after that.

Ethan came instantly, his cream shooting out in hot ribbons on to the concrete floor. It was easily the strongest orgasm of his life. He couldn’t believe he could cum like that. His arms and legs gave way, only just having enough strength to make sure he didn’t scrape himself on his way down.

The toy was pulled clear from his asshole. His softening cock had collapsed into the mess he’d made on the concrete.

Ethan groaned.

“Fuck…”

“I feel like you got more out of that than I did.”

“Get lost Emma.” Ethan gasped “You pretty much just assaulted me.”

“Oh, sure. Roll over.”

Ethan did as he was told. Immediately. He internally scolded himself for being so submissive. The pool of fresh cum was obvious on the floor.

“That’s a lot of cum for someone who wasn’t into it.”

“I can’t help what my body does.” Ethan looked up at her and was shocked to feel so many different things. Deep anger that she’d uncovered something so private, something not meant for her. There was lust too, how had he not noticed his step sister was pretty. Beautiful even? She lived in his house. How had he not noticed her pretty, full lips, and the perfect shade of brown her hair was?

But worst of all was that she was triggering his desire to be submissive. Completely naked, on the garage floor, his soft cock covered in his own cum and his asshole still slightly open from her rough treatment, he experienced an almost painful urge to serve her. To ask what she needed and to supply it at any cost.

The worst thing about it all was it felt like she could see all of it. She was his stepsister. She did know him. Is it possible she knew him that well?

It was terrifying.

“You’re a psycho. Go away so I can get changed.”

She grinned, not at all bothered by his outburst.

“Clean up your jizz loser.” He watched her walk away, her strap on in one hand. He didn’t take his eyes off her until she left the room.

Once she was gone, he allowed himself to collapse on to the floor. Had he just fallen in love with his Stepsister? What a total fucking nightmare. But he was grinning as he got changed. This did make things interesting at least…