Jenna’s Surprise

By Ebert O.
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Jake and Jen had always been close. When they were younger, on nights when their mother was out with boyfriends, they’d snuggle together under a blanket on the couch watching movies. She liked having his warm body next to hers. Over time, her hand found its way to his crotch. Jake didn’t object. So, even though she’d never seen his penis, she knew what it felt like. She liked feeling Jake’s erection grow and would get him pretty close to an orgasm before he would make her stop. As they got older, they stopped watching movies together. Jake lost interest in his little sister and kept to himself. Now, he had a girlfriend. But Jenna could still hear him jerking off at night when he went to bed.

When Jake caught Jenna with Duke, she knew he’d want payback, but she hadn’t guessed the price. Jake knew what Jenna was trying to do. Over the next few days, he decided that if she wanted Duke to fuck her, she shouldn’t mind letting him use her body in the same way. It didn’t seem like a big deal, and he desperately wanted something better than his nightly hand jobs.

The next day, he made the offer she couldn’t refuse. Jenna was in shock.

“You pig!!! What’s the matter with your girlfriend?! God!!! Can’t she take care of your ‘needs’?”

Jake tried to explain. It was a long story, but the short answer was no, she wouldn’t take care of his ‘needs.’ Jake had what they needed to be safe, but she was too afraid to go through with it. After what happened at Lisa’s, Jen knew how it felt to be afraid. So, she sympathized with Jake’s girlfriend. But, feeling the itch for her first doggy-fuck, she could also sympathize with Jake.

Jake pleaded, “Jen, she can’t do it. So, I’m asking you.”

He was almost begging, and this put his extortion in a different light. Jenna wouldn’t admit it, but she was warming up to the idea. Still, this was playing with fire! Unlike doggy-fucking, Jenna knew she could get pregnant, even worse, with her brother’s baby! While Jenna sat thinking about it, Jake went to his room and brought back the box of contraceptives he’d bought but never used with his girlfriend. Jenna tried to hide her interest. But Jake noticed. He’d have to be patient, and she would come around.

Putting aside everything else, Jenna told Jake she was repulsed by the idea of making love to her own brother. It seemed creepy, and she wasn’t sure she could do it. He calmly assured her it wouldn’t be ‘like that. It was only for a little pleasure, no different from what she was trying to do with Duke. No romance, just sex. It would be just like watching a movie together. She knew what he was talking about but was still dubious it could work like that. Jake persisted, persuading her that they wouldn’t get all emotional. Then, he reminded her about the box of toys in the back of her their mother’s bedroom closet.

Years before, mom’s boyfriend was into all kinds of kinky stuff. Mom thought her kids didn’t know what was going on, but they did. One afternoon, Jenna and Jake found mom’s toys. They got a good look at the leather cuffs and belts, whips and blindfolds before carefully putting them back.

“We’ll hold you down and blindfold you before I do it. After that, you won’t have to do anything or even watch.”

A shiver of excitement shot through her body. They looked at each other, and they both knew she had agreed. She made her brother swear he’d never tell anyone about Duke or what they were about to do. He handed Jen the Trojans and went to get ‘the box.’ It was still in the back of the closet, apparently unused for years. When he got back, Jenna had opened the box of condoms. He opened the box of mom’s toys and began attaching the nylon belts to the bed frame. She carefully ripped open one of the lubricated condoms. When Jake found the blindfold, he held it up for her approval. Jenna nodded. Jenna had never seen a condom before, so she took her time looking at it. Its size surprised her. Bigger than she expected. She felt her pussy getting moist.

“Jen.” She looked up at him, “Take off your panties!”

She did. Under her skirt, the cool air reached her bare wet crotch. She sat on the edge of the bed to let him put the cuffs on her wrists and ankles. He tightened the two little buckles on each one. When he was done, he didn’t have to tell her – she got on her back in the middle of the bed and spread her legs. With instinctive modesty, she made sure to cover her nakedness with her skirt. He clipped the nylon belts onto the cuffs and drew them snugly. Feeling herself restrained sent a pulse of adrenaline through her. He kicked off his shoes and dropped his pants before getting onto the bed beside her. He picked up the blindfold to cover her eyes.

“Jake. Wait. I wanna watch you put on the condom.”

For the first time, she got a good look at his penis, obscenely erect, sticking out in front of his crotch. He pinched the end of the latex sheath as he rolled it on, leaving half an inch or so hanging in front.

Then everything went dark for Jenna. She lay her head back on the pillow and took a deep breath. This was Jake’s first time. He had anticipated it for months but expected to be with his girlfriend. When Jen felt her inexperienced brother nudging a pillow under her ass, she remembered ‘Thirteen Tips for the Missionary Position’ in Cosmo the previous month. Had he been reading her Cosmos? When his wet fingers ran between her already slick labia, she relaxed, pretty sure he had. He imagined his girlfriend’s slit – pink and warm, smooth and wet. He probed her vagina gently with his finger. Then Jenna felt the bed jiggle as he got into position.

Jake did his business quickly and efficiently. His penis pressed against her, then went deep, sliding in slowly (another Cosmo tip!). Her vagina stretched to accommodate him. He felt the snug warmth that no male ever forgets. He held himself inside her for a moment before beginning shallow strokes. The texture of her vagina caressed his glans, quickly doing its work on this first-timer. He soon grew tense. His strokes became faster and longer. Jenna liked that. She wished she could lift and spread her legs more. Then, he began to shake, and his movements became irregular. He felt the semen begin to flow into the base of his penis. The fullness grew ever more urgent. Then, the point of no return, that delicious moment of surrender he felt every time he jerked off. She had no way of knowing he was about to come. He gave no warning, just a hard thrust of his pelvis against hers as he succumbed.

Uh, Ughh, Uuhhhh, Uggghhh….”

The series of ejaculations forced out his semen and triggered his orgasm. He called out his girlfriend’s name in his ecstasy. Jenna felt his body react to each spasm and felt his warm breath on her face. Jenna loved feeling him come. She was excited to learn what her body could do to his. She wanted to kiss him and wrap her arms and legs around him, but of course, she couldn’t.

He was breathing hard, and his body had gone limp. It had taken him less than a minute. Not quite what Jenna had expected, she remembered Prince furiously humping me for a long time before laying quietly on my back as he delivered his semen. She expected something more like that. But, as soon as her brother got quiet, he withdrew, got off the bed, then loosened the straps and unclipped the cuffs. Then, without saying a word, he retreated from her room.

Jake was ashamed. He was embarrassed and afraid that someone would find out he’d fucked his own sister. He promised himself he’d never do it again. Such promises are easy to make. But, the effects of male hormones and the lack of other options meant his promise would soon be broken. Deep down, he knew this, and it made him even more ashamed.

Jenna was alone and confused. She removed the blindfold, the cuffs, and the pillow then slipped on her panties and smoothed her skirt, unsure how she should feel about what just happened. She was disappointed. In fact, Jenna and I would continue to enjoy more intense sexual satisfaction than she ever would with Jake. Still, she felt good that she had given her brother something he needed and hoped it had satisfied him. She knew he’d be back for more and hoped it would get better. This had been the first time for both of them. She was glad it had been with someone she would always know and love, instead of a boyfriend who’d soon be gone and forgotten except for being ‘her first fuck’.

Now, Jenna’s thoughts turned to Duke. She still felt an itch that hadn’t gotten scratched by Jake. She wanted Duke to fuck her hard and fast and long, then slowly fill her with his doggy-cum. It was all she could think about, and what I’d been hoping for because I knew, once I helped Duke satisfy her, I’d get my turn.

 

The End.

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*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t always mean the flaws in a story are always fixed.

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