Emma's New Dilemma

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The follow up to 'Emma's Dilemmas'.
2.2k words
4.5
19.2k
38

Part 2 of the 5 part series

Updated 02/22/2024
Created 12/24/2020
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It had been a month since Emma's first tryst with her next door neighbor Stephen. Twice she'd had sex with the man and twice she'd felt guilty for enjoying it.

Now it had been a whole month since she'd last been alone with Stephen and she was feeling that itch again. In that same month her parents had elected to use up a lot of saved vacation time to get some things done at home. Concurrently her temp job downtown ended. That meant she was had no excuse to slip away to her neighbor's bed to further explore the miracle of the male appendage.

Over the intervening weeks she and Stephen had exchanged pleasantries in the yard and her parents noticed Emma's newfound civility towards their neighbor. They just accepted this new wrinkle as their daughter simply being more polite and courteous.

The emotional impact of having been intimate with Stephen was also settling in on Emma. She unexpectedly found herself having feelings towards him that she never thought she'd have. He was older, he was sweaty, he was a little out of shape, and somehow it mattered to her what he thought of her.

Emma was also torn by the worry of becoming pregnant so when her period showed up on time she was relieved. But at the same time she found herself worried because she knew she wanted to be with Stephen again. At night she would dream of him making love to her and in some of the dreams she'd even feel his cock sliding in and out of her body. A few mornings found her waking up and having to satisfy herself before she could start her day.

It had been a week since her period ended when her parents went away to Arizona to visit one of her grandmothers for a few days. Emma slept hard the night her parents left. She tossed and turned and a big part of her wanted to go see her neighbor in the middle of the night.

When she woke up early in the morning she jumped into the shower and then made herself pretty. Knowing what she wanted to do she decided to wear just a strapless terry cloth dress and her flip flops. The panties and bra were left behind.

Going downstairs she went out the back door of the kitchen and slipped into Stephen's yard. She was just about to knock on his backdoor when he opened it himself. He was wearing just a tank top and boxer shorts.

"I was wondering when you'd be back." he said.

She looked at him and hesitated, "How did you know I'd be back?"

He smiled. "Because here you are and you're not here just for the coffee, are you?"

She demurely started at her feet and replied, "No, I'm not."

He gave a small laugh and then took her hand and led her back to his bedroom. The bed had clearly been occupied just a short time before.

He kissed her and she kissed him back. Emma didn't complain as his hands pushed the terry cloth dress down her body, letting it puddle at her feet. His tank top and boxers rapidly followed.

Emma looked at Stephen and then down at his hardened cock. It bounced from his heartbeat. She studied the head of it and as she wondered about it being deep inside her body she flushed with arousal.

He guided her to the bed and she felt his warmth in the sheets as she laid back. The older man moved quickly yet gently as he got onto the bed with her.

His warm mouth promptly clamped onto her right breast and started sucking on it. Hard. His hands went to her other breast and kneaded it before one hand went to the place between her legs. She responded as he motioned for her to spread her legs and then she felt one of his fingers easily swipe through her pussy lips. Despite her misgivings she realized that she was completely aroused and ready for him to...mount her.

'Yes', she thought to herself, 'that's what he's going to do'.

And she realized she wanted him to. A lot of thoughts crossed her mind. She was torn at the prospect of being a pregnant eighteen year old. She felt impulsive and stupid for deciding to come see Stephen again. She had gotten so lucky that Stephen hadn't made her pregnant the month before. Was this a mistake? Was Stephen the right choice for her? Would he make a good father? Would he make a good husband? Would she end up a single mother?

As she tried to reconcile all of these thoughts Stephen had gently gotten himself on top of her. The weight of his hips uncomfortably pressed into hers and she instinctively spread her legs wider to relieve the discomfort. His body quickly and perfectly settled into the saddle of her hips.

The cacophony of thoughts in her mind suddenly cleared as she felt the head of his cock press into her. It was happening so fast! Her hands went to his hips and pushed him back but his body started to push into hers anyway. Emma felt the first push of his cock into her body and her hands instinctively went to his sides to encourage him. He took his time and in doing so let Emma unknowingly set the pace. He loved that this fresh young woman was so eager for him.

He did his best to advance only a little with each stroke into her pussy. This way she got him a little deeper each time and he could hear her breath catch as he did so. When he finally felt the head of his cock kiss up against her spongy cervix he simply held himself there and luxuriated in feeling her wonderful body beneath him and surrounding him in so many ways. But he could only hold back for so long.

Emma cried as she felt him start to fuck her. It was a cry of relief as she allowed herself to submit to their shared sexual desires. The tears came freely as she felt his cock plow in and out of her body.

He kissed her on the mouth and she didn't care that his breath smelled of coffee. Nor did she care that he needed a shave. All she cared about was that he was fucking her and satisfying a need that erupted from deep within her being.

He was careful to deeply fuck her and then slow down. Sometimes he even stopped to hold off the inevitable. It allowed Emma the time to relax and submit to her own pleasure.

At some point her world seemed to focus on the male flesh sliding in and out of her body. And then it happened! It began in her belly and then it became a tingling that started in her toes. She wrapped her arms around her lover and held him tight as her body trembled with release.

Stephen marveled as her pussy contracted around his cock. It felt so fucking good! As much as he wanted to prolong this feeling he couldn't help but fuck her fast and hard.

Emma's pent up sexual frustrations were cresting and releasing as she felt Stephen's cock swell and then start throbbing and pulsing. It was almost like it was dancing inside of her pussy! A moment of clarity hit her as she realized she was being inseminated again but it faded as he fucked her hard bring her to yet another peak.

Time slipped away from her and it was a few moments later when she became aware of her surroundings. Stephen had rolled off of her body and was catching his breath. The man was a sweaty mess and she felt his sweat on her body. She didn't mind.

When she went to move the effort caused a gush of Stephen's cum from her pussy. Her hand went to it as Stephen noticed and silently handed her a tissue.

She wiped the gooey, slimy cum from her pussy and felt dirty for having let him cum in her again. In her mind she found herself enjoying the feeling of having been used by the older man.

His hand moved onto her body and she looked at him as he smiled. She felt him reach between her legs and wet his fingers in their mutual fluids. Then his hand moved to her nipple and started to wetly massage it. She liked it.

They explored each other over the next twenty minutes or so and then her hand went to his cock. She gently held the softened cock and manipulated it. Soon it started to swell and she felt his hips move in her direction. She was about to move when he spoke.

"Stay there."

He moved so she lay with her head on the pillow and his body made a kind of T at her hips. He took one of her legs and had her place it between his own. Her other leg he draped over his body.

Her pussy was now aimed directly at his crotch. Stephen grabbed hold of his cock and guided it back into her body. Then he scooted himself closer to her. His cock was now buried as deeply as possible inside of her and he just held it there. His hands explored her body paying repeated attention to her belly.

"You like my tummy?" she asked.

"I do. That's where our baby's going to be."

In any normal circumstance she'd have found that statement scary. But with his semi-soft cock safely seated within her pussy Emma suddenly found herself wanting to be gravid with Stephen's child.

Her eyes closed and she concentrated on his cock. He would only move a little and then only so often. But when he did move she felt electric and she wanted more.

She felt it as his cock slowly firmed up again. It was amazing to her that her body was arousing him so much! The feeling of being sexually attractive to a man was unexpected and Emma reveled in the realization.

Slowly he started to fuck her again. Their new position allowed Stephen to press even more of his cock into her pussy. He'd fuck himself into her and then push just a little more. Emma found it somewhat uncomfortable to have him so deep inside of her body but at the same time she loved feeling him fuck her this way.

Unlike their first joining of the morning this time the eagerness was gone and the fuck was gentle, slow, deep, and the two lovers were able to exchange glances and soft caresses.

Her hand wandered down her belly until her fingers told her of where his cock was pumping in and out of her body. Even though she'd felt his cock inside her body before it seemed more real when her fingers slid along his cock where it parted her pussy lips.

She glanced at Stephen as he fucked her. His eyes locked on hers.

"Keep your eyes on me." he said.

As their mutual ardor increased she did as she was told and kept her eyes locked on his.

His look became more determined. She felt the first tinglings of release and bit her lip. Their fucking started to take on an urgency and the bedsprings sang of their efforts.

His cock was now pounding her soft insides and she grimaced as he occasionally pushed too hard. Her hands went to his hips to hold him back and his hands went to hers to hold her close.

Suddenly her pleasure rose and crested. Her body was out of control now and she was lost in her ecstasy.

Stephen loved seeing her this way and the thought of Emma submitting to him was itself so intense that it made him start to feel his cum building up. He fucked her harder and then drove deep into her as his cum erupted against her cervix over and over. He continued to fuck her, getting his cock to spit a few more squirts of cum into her body.

Finally, he was spent and he stopped fucking her while keeping his softening cock within her pussy.

Emma went to move and he put a hand on her belly to hold her down.

"I was going to go clean up." she said.

"I know. But there's a better chance you'll get pregnant if you stay with me for a while."

Her eyes went wide.

"Don't act surprised with me. You and I both know what you're doing here."

She drew in a breath. He was right. She knew it. She had been about to protest his assertion yet the reality of the moment is here she was in his bed with his spurting cock inside her pussy. Of course she wanted to get pregnant! Her mind quickly moved along from objection to acceptance.

"What if I get pregnant?" she asked.

"Then you move in here and I get to fuck you a lot more, that's what."

She felt his cock swell just a little as he said this.

And then she smiled.

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BaztrachianBaztrachian11 months agoAuthor

Maisy_P, thank you for your feedback! Much appreciated!

Maisy_PMaisy_P11 months ago

Delightful story. I don’t know why his unappealingness makes it even better. Something about the girl being debased and robbed of choice. This happens in the stories of another great author, StarryHorizon, and I find it extremely effective.

WittonWittonover 2 years ago

Some explanation for Emma's behavior and choices would make the story tolerable - the sex is first rate but the setting is crap

Ilfen1Ilfen1over 2 years ago

I mean, I liked it. But also I would have liked a more flattering physical description of Stephen than "a little out of shape".

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