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Having lost her nerve for doggy-sex with Prince at LIsa's, then watching me do it, Jenna was eager to try it with Duke. The next afternoon, she tried and failed to get him to mount. What’s worse, her brother caught her naked on the floor with Duke’s red-rocket ready to go. He agreed keep what he saw to himself, but there would be a price.
Half-siblings 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 grow and would get him pretty far-along before he would make her stop. As they got older, his hands roamed first to her tits and then to her crotch. But by then, she wasn’t interested and pushed his curious hands away. Rejected by Jen, Jake lost interest and they soon stopped watching movies together. The sibling incest taboos had kicked in and they each kept to themselves. Now, Jake had a girlfriend. But Jenna could still hear him jerking-off at night when he went to bed. She enjoyed petting the beaver, but tried to be more discreet.

When Jake caught Jenna naked on the floor with Duke, they were both embarrassed. He promised not to tell, but she knew he’d want payback. It was just a matter of agreeing on the price. Jake knew what Jenna was trying to do and was hurt that she wanted sex with Duke after rejecting him. Over the next few days, he convinced himself that if she wanted Duke to fuck her, she shouldn’t mind letting him use her body in the same way. In his mind, it didn’t seem like a big deal, and he desperately wanted something better than his nightly hand jobs.

The next day after school Jake went into Jenna’s room and made his offer. At first, Jenna was disgusted and in shock.

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

Jake tried to explain. It was a long story, but the short answer was no, she wouldn’t take care him and he remained a virgin. Jake had gotten what they needed to be safe, but she was too afraid. After what happened with Prince, 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 felt herself warming-up to the idea. Like Jake, she too was still a virgin even though her hymen was long gone. Still, this was playing with fire! Unlike doggy-fucking, Jenna knew she could get pregnant – even worse, it would be her half-brother’s baby! While Jenna sat thinking about all this, Jake went to his room and brought back the box of contraceptives he’d bought to use with his girl friend. Jenna had never seen condoms before and tried to hide her growing interest. But, Jake noticed and handed her the box. He was patient and she was curious.

Studying the box of Trojans, Jenna admitted 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 assured her it wouldn’t be ‘like that’. They would do it once, just to see what it felt like. It was really no different from what she was trying to do with Duke. No romance, just experiencing sex. He coaxed, reminding her how they used to watch movies together. She knew what he was talking about, but was still reluctant. Jake insisted that they could do it without getting ‘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 went looking for mom’s toys. They got a good look at the leather cuffs and belts, whips and blindfolds, before carefully putting them back.

Jake suggested, “We’ll tie you down and blindfold you. You won’t have to do anything or even watch.”

A shiver of excitement rippled through her body. They looked at each other, and they both knew she had agreed. She made her brother swear he’d never to tell anyone about Duke or what they were about to do. She broke the seal on the box of Trojans and he went to get ‘the toy box’. It was still in the back of the closet, apparently unused for years. When he got back, Jenna watched as he opened the cardboard box and took out the leather cuffs. They both looked at them and handled them. Jenna had never thought about bondage before and she was getting excited. She nodded and Jake began attaching the nylon belts to the bed-frame. She carefully ripped opened one of the lubricated condoms. Jenna had never seen one before, so she took her time looking at it. Its size surprised her. Bigger than she expected. She felt her pussy getting moist. When Jake found the blind-fold, he held it up for her approval, Jenna smiled.

“OK Jen, 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 leather 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, carefully spreading her hair on the pillow. With instinctive modesty, she made sure to cover her nakedness with her skirt. He clipped the nylon belts onto the cuffs and drew them snug. Feeling her legs being pulled apart by the restraints sent a pulse of adrenaline through her. When she was secure, he kicked off his shoes and dropped his pants before crawling onto the bed beside her. For the first time, she got a good look at his penis, obscenely erect, sticking out in front of his crotch. He picked up the blindfold to cover her eyes.

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

She lifted her head to watch him pinch the end of the latex sheath as he rolled it on, leaving half-an-inch or so hanging in front. After that, 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” she’d read in Cosmo the previous month. She wondered if he had he been reading her Cosmos? When his wet fingers ran between her already slick labia she relaxed, pretty sure he had. He was imagining his girlfriend’s slit – pink and warm, smooth and wet. She was thinking about some as yet unknown boyfriend getting ready to fuck her. He probed her vagina gently with his finger. Then Jenna felt the bed jiggle as he got himself into position.

Jenna’s virgin brother did his business quickly and efficiently. His penis explored along her slit several times, found the spot, 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 to stroke. The texture of her vagina caressed him, quickly doing its work on this eager first-timer. He soon grew tense. The strokes became faster and longer. Jenna liked that. She strained against the restraints trying to lift her hips and spread her legs. Then, he began to shake and his movements became irregular. He felt the semen filling the base of his penis. The fullness grew ever more urgent. Then, the point of no return, that delicious moment of inevitable surrender he felt every time he jerked off. She had no way of knowing he was about to come. He gave no warning, just hard thrusts of his pelvis against hers as he succumbed.

“Uh, Ughh, Uuhhhh, Uggghhh…..”

The series of ejaculations forced out his semen and triggered his orgasm. Jenna felt his body react to each spasm, and felt his warm breath on her face. He called out his girlfriend’s name in his ecstasy. Jenna loved feeling him come – excited to learn what her body could do. 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, laying heavily on hers with his sweaty face along side hers. It had taken less than a minute. Not quite what Jenna had hoped for. She remembered Prince furiously humping me for what seemed a long time before settling on my back as he delivered his semen. But, as soon as her brother got quiet, he withdrew, lifted himself and got off the bed. He 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 this promise would soon be broken. Deep down he knew, and it made him even more ashamed.

Jenna was alone and confused, unsure how she should feel about what just happened. She removed the blindfold and cuffs, then went to the bathroom to clean herself, slip on her panties and smooth her skirt. Back in her bedroom her most intense feeling was one of disappointment. Jenna and I would continue to enjoy more intense sex than she had had with Jake. We weren’t lesbians, but we did know how to make each other feel good. Still, she had given her brother something he wanted and hoped it had satisfied him. That said, she knew he’d be back for more and hoped it would be better next time. 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 some boyfriend who’d soon be gone and forgotten except for being ‘her first-time 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 settle onto her back to slowly fill her with his warm doggy-semen. In the coming days, it was all she could think about, and what I’d been hoping for, because I knew, once I helped her take Duke, I’d get my turn.

Ebert OReport

2021-09-18 16:21:40
Tiger_t - Have you read the previous chapters of this story? They are: Lisa and Prince, Lisa and Prince -- day 2, and Lisa and Prince -- and Jenna. Ebert


2021-09-16 14:31:30
Great start, next chapter?


2021-09-07 22:12:45
nicely done.


2021-09-05 13:27:18
wow what a great story


2021-09-05 13:27:18
wow what a great story

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