Awkward Anal

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Like with her mother, he straddled her legs, took his cock in hand and smeared a coat of lube on it. Her slender legs were a lot easier to get his own around and far less stubbly. He jostled up a little and parted her cheeks, a bit fidgeting and his cock lined up nicely.

Emma had once seen a film where a man's legs were held down in such a manner before being sawn off, it felt she was about to undergo the same.

"Can you push out for me? I'm going to try and enter as slowly as I can."

Emma took a deep breath, held it under gritted teeth, then pushed out. The pressure increased on her hole slowly building until it surrendered. She released her breath in one groan, then panted as Peter lay forward, pushing further into her in a slow controlled manner until he was fully inside. She was as tight as he both imagined and hoped for, but she took it well.

"That's the worse bit over, You ok?" he asked as he lay still on top.

"Oh god it feels weird, all swollen and squishy," she replied in a hushed voice."

"You can relax your legs if you want, might feel less swollen. "

Peter gave a few soft thrusts, Emma squirmed as he did, her rectum fluttered around him like a living gelatinous mass. He held still once more, "Do you think you can handle that?

"I think so, but no hard fast trusts please."

"I'll just keep it steady."

Peter began to shift his hips in a slow rhythmic fashion. His cock moved like a piston gently stirring her up. Soft and encompassing she embraced every inch wrapping his cock in warm billowy joy. Her body writhed under his as slowly he took her. Oh how he would have loved to take her blouse off and feel her young skin next to his. To reach under and cradle those breasts. As for that pussy, so close yet so far, what he could do with a finger or two.

Emma had hoped she could remain detached, lie and take it as if she were being examined by a medical professional. But she couldn't, like it or not a man had his cock inside her. That one small organ moving in her was dominating every sensation, emotion and thought.

Between her shallow panting breaths, a small squeak would escape, perhaps a whispered, "Oh fuck" or "Oh god." Unless she began screaming in pain, he knew she wasn't suffering too much.

The phenomenon was an enigma to Emma, a deep doughy feeling mixed with a writhing wiggly sensation as his cock churned and pumped, turning that region into a confused mess. So, this was sex? Anal sex at least. The thing she once thought she'd never have.

"Can you stop a second?" she called out.

"You ok?" he replied as he ground to a sudden halt.

"I just feel trapped like this, can we switch to missionary?"

It was Peter's favourite, he wasn't going to argue. He slowly pulled out and glanced at her gaping hole as it slowly closed. Emma rolled on her back and opened her legs as she pulled her legs back. Peter wasted no time getting between her spread thighs, lifting them slightly with his knees.

Penetration was easier than before but not as deep. Peter didn't mind, it felt better to him and there was something about looking into a girl's eyes as you plough them. He leaned forward but kept his body tilted off hers, "Wrap your legs around me, it's better for you."

He was right, things seemed to angle just right. Her hips rocked freely with his thrusts as each lunge lifted her swaying her body. In the dim light, he caught a glimpse of her smile as she bit her bottom lip, he responded with two long thrusts driving his full length in both directions taking her breath away.

For a second she felt ashamed at showing pleasure but he was in no doubt she was enjoying it. "Fuck it," he thought, "I'm just gonna have sex, none of this soft see-saw shit."

He began moving at a more natural pace watching carefully for any signs of stress. None came, if anything she began to enjoy it even more, even allowing herself an occasional moan. When she began thrusting back, he knew he had made the right move.

Emma locked her ankles and gripped his arms at her side, mother was right anal was giving her physical pleasure. It was indescribable and scary but undeniably filling her with a deep squirmy squechy wonderous feeling. Part of her wished it didn't, but god it did.

Peter spotted how she had surrendered her body to his cock, more importantly during his varied thrusting he had learned what made her groan and shake. Now was the time to switch tactics and focus his thrusts.

The change was not lost on Emma, wild random twangs of pleasure were being concentrated into a growing tingling buzz. Her legs vibrated, trembling as it built inside her. "Oh Christ, I think I'm going to orgasm," she thought, "This shouldn't be happening, God no."

Her fingernails dug into his arms and her face turned from one of joy to one of fear. She wanted to scream stop but her body wouldn't let her. The building pressure was realised in a seismic wave sending her into wild squealing convulsions.

He froze to enjoy the view of his endeavours and reap the reward of her pulsating body. Her orgasm faded to a trembling shame. He brushed her hair off her blushed face, tilted her head and before she could speak silenced her tongue with his. A half dozen long thrusts and his swollen cock delivered it's goods into her quivering body.

Slowly he withdrew and lay beside her, "You think your parents heard?"

"Oh god I hope not, I can't believe that happened."

"Same time next week? He laughed, "You know I've some mates down the rugby club I'm sure would help you out as well. Come on let's go face your parents.

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4 Comments
P_AndererP_Anderer10 months ago

Provided you are prepared to suspend disbelief for a few minutes, this becomes an enjoyable read. It would be worth getting an editor to help eliminate the errors and typos, but these don't really detract.

A good, original storyline!

incipient_delightincipient_delight11 months ago

Obviously a far-fetched situation, but that’s okay, this is fantasy after all! Nicely written though, with a good build up to the action. Poor girl! Glad she enjoyed it in the end.

redlion75redlion7511 months ago

Good thing she's not a lesbian or religious.

Dumbest medical condition in the known universe.

smooth_Ballssmooth_Balls11 months ago

I never heard of a medical condition like that, and such a limited range of options for therapy but it does help to motivate what the story is about: parents arranging a situation where a shy virginal daughter is initiated into sex, anal sex.

Mom taking her girl to a hook-up place and walks her step by step through the date until they give head to a young man each, side by side and daughter following her mom's example.

Mom and dad discussing how to find suitable candidate so their young daughter can have an anal dicking once a week as the doctors prescribed, which includes dad asking his buddy's son and he has to agree that Mom will test-drive every guy to make sure they are gentle.

What makes this story so charming is how the author lets the family talk and act about sex in such a natural and matter of fact way.

Like with most of the stories of this author the men are there for their part of the game but the focus of the story is more between the women, between mother and daughter accepting each other as grown sexual being.

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