My name is Amy, Jenna’s next door neighbor. Last week, Lisa and I tried to introduce Jenna to her first-time doggy-sex, but at the last minute she lost her nerve. Instead she watched Lisa’s dog Prince fuck me.* Jenna’s ‘failure’ left her eager to try again. So, the next afternoon, alone at home, she tried to get her dog Duke to mount her. Disaster struck when her brother, Jake, caught her naked on the floor with Duke – his red-rocket ready for action.
Half-siblings Jake and Jen had always been close. When they were younger, on nights when their twice-divorced mother was out with boyfriends, they’d snuggle together under a blanket on the couch watching movies. She liked having Jake’s warm body next to hers. Over time, his hands began to roam – first to her tits and then to her crotch. She liked the way it made her feel and her hand found its way between his legs, too. So, even though she’d never seen his penis, she knew what it felt like, and she liked feeling it grow, not appreciating the frustration she was causing him. Then one night after she’d gotten him really hard and horny, Jake made a move on her. It was clumsy, and she got scared – kicking, punching and pushing him off. Jake left the room and they never watched movies together, again.
As they grew older, Jenna could hear Jake jerking-off at night. Even though she was younger, she knew what he was doing. More recently, Jake began working several nights a week at the movie theater and spending his other evenings with a new girlfriend, named Becky. Jenna tried to imagine the kind of sexy stuff her brother and Becky were doing. But, at night she could still hear him jerking-off, unaware of how frustrated Jake was getting because of Becky’s unwillingness to go all the way.
The day Jake caught Jenna naked on the floor with Duke, he knew what she was trying to do. They were both embarrassed, and he promised not to tell, but she knew he’d want payback.
Jake was upset, but more than anything, he was hurt because Jenna was trying to have sex with Duke, after rejecting him. It had been several years, but he still hadn’t gotten over it. During the next few days, Jake’s hormone-intoxicated male brain convinced him that if Jenna wanted to let a dog fuck her, she wouldn’t mind letting him. It seemed totally logical and it didn’t seem like a big deal. This bit of faulty logic was driven by his need for something more than nightly hand jobs. So, the next day he was waiting in Jenna’s room when she got home from school and made his proposition.
Jenna was in shock. “You pig!!! What’s a matter with you?! God!!! Can’t Becky take care of that for you?”
Jake tried to explain, but the upshot was ‘no’, Becky wouldn’t take care of it. He’d purchased the condoms they would need to be safe, but she was still too afraid. After Jen’s experience with Prince, she knew how it felt to be afraid. So, she sympathized with Becky. But, still itching for her first doggy-sex, she also understood how Jake was feeling.
Jake pleaded, “Becky can’t do it. So, I’m asking you.”
He was almost begging, which put his extortion in a kinder light. Jenna felt sorry for her frustrated brother, and tried to convince herself it would be OK. She wasn’t worried about her virginity. We’d both already lost that playing with my mother’s dildo. Still, this wouldn’t be a doggy-fuck. She could get pregnant – with her brother’s baby! While Jenna sat mulling this over, Jake went to his room and brought back the box of Trojan-Enz he’d bought for Becky. Jenna hadn’t seen condoms before and couldn’t hide her interest. Encouraged by her curiosity, Jake handed them to her.
Jenna contemplated the unfamiliar little-blue box. She’d been told incest was wrong, and she understood why. So, she told Jake it was too creepy, and she wasn’t sure she could do it. But, Jake noticed that she hadn’t said no, so he persisted, assuring her that she would ‘just be letting him see what it felt like’. It would be quick and painless with no strings attached. Jenna was unmoved. He reminded her of the time they spent under the covers watching movies together and how he loved the way she touched his penis. Her thoughts turned to the feeling of holding it in her hand, and she couldn’t help wondering how it might feel inside. He sensed he was getting to her, so then Jake reminded her about the box in the back of her their mom’s closet.
Several years before, mom and her boyfriend were into kinky sex. Mom thought her kids didn’t know, but they’d heard everything. One afternoon, Jenna and Jake went looking for mom’s sex toys. Finding the box, they got a good look at the leather cuffs and belts, whips and blindfolds.
Jake suggested, “You can use a blindfold, so you won’t need to watch me do it.”
But, she wasn’t thinking about the blindfold. It was thoughts of the leather cuffs that held her interest. The idea of having sex while being held captive sent a shiver of excitement through her. Jenna hadn’t yet even heard the work bondage, but she felt her pussy getting moist and Jake saw her resistance crumbling. He retrieved the box and opened it. Jenna immediately reached for the cuffs. She held them, running her fingers over the soft black leather and the sturdy metal buckles and rings.
“I’ll do it if we can use these.” she said sheepishly.
It was a deal. Jake went to work attaching the nylon belts to the bed-frame. Jenna opened the box of Trojans, removing the three small plastic pouches and ripping one open. She’d never touched a condom before. It was so thin that it was translucent, slippery with the box claimed “Spermicidal Lubricant” and bigger than she expected with a nipple on the end. She placed it on the night table as Jake reached into the box and held up the blind-fold. Jenna smiled and nodded.
“OK Jen, take off your panties!”
She did, along with her shoes and socks, then sat on the bed to let Jake put the leather cuffs on her wrists. He secured the two brass buckles on each one. When he was done, he motioned for her to lay back in the middle of the bed. He buckled the ankle cuffs as she spread her hair on the pillow and adjusted her skirt to cover her nakedness. Jake gently took her hand and clipped the cuff to the nylon belt above her head. This was the first time he’d touched her in a very long time. It felt good. Then, one-by-one he attached each cuff to its strap. When he was done he gently drew them snug. Feeling her legs being pulled apart by the restraints, she was giddy with excitement and insisted Jake draw them tighter. Once she was secured to her liking, Jake 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, fully erect and bouncing obscenely in front of his crotch. It was a lot bigger than the Duke’s doggy-cock.
Jake picked up the blindfold, but Jenna objected. Motioning with her eyes over to the condom, “Not yet. I wanna watch you put it on.”
She trusted him, but wanted to be sure. Lifting her head, she watched him pinch the end and roll on the thin latex sheath. She stared at the empty nipple which hung in front ready to be filled. But then, everything went dark for Jenna. She eased her head back on the pillow and took a deep breath preparing herself for what was coming.
Jake was nervous. It was his first time, and he’d been anticipating it for months. When Jen felt her inexperienced brother lifting her skirt and nudging a pillow under her ass, she remembered the “Thirteen Tips for the Missionary Position” she’d read in last month’s Cosmo. She wondered if he’d read it, too. But then she felt his fingers moistening her already slick labia. She was already conjuring her favorite fantasy – Mark, the hottest boy in her class, kissing and caressing her. The bed jiggled as Jake got himself in position and as she waited, she envisioned Mark doing the same – ready to penetrate her just as she did at night when she masturbated.
As he promised, Jenna’s brother did his business quickly. Reality intruded briefly on Jenna’s fantasy when she felt his cold sheathed penis probing her slit. Then he found the spot and pressed forward, slowly opening her. Jake’s glans passed beyond her vaginal sphincter. Then as he penetrated, that tight little ring of muscle slid down along his hyper-sensitive penis. Jen’s body tensed, and she caught her breath as her vagina stretched to accommodate him, but she had already drifted back into fantasy land with Mark, her eyes closed, her expression blissful and dreamy. Jake’s pelvis touched hers and for the first time he was experiencing the snug warmth of her maidenly pussy. His balls hung down, lightly resting on her cool-wet ass.
He paused a moment, then began to stroke. As her vagina did its work on him, his strokes increased in pace and depth. She began to pick up his rhythm, exhaling in little involuntary gasps with each thrust. She loved it, fighting her restraints to take him deeper. But then, his legs began to quiver and his movements became irregular. Jake felt the effect of semen filling the back of his urethra, a familiar urgent ever-growing fullness. As he reached the point of no return, he held his cock deep inside Jenna and succumbed.
His body convulsed, and he gave a deep guttural, “Uggghhh.”
A gush of semen from his first powerful ejaculation filled the condom. Jenna felt his body shudder, and then his reaction to each subsequent ejaculation – seven or eight in all – each slightly less intense than the one before. He moaned and called out Becky’s name during his moments of ecstasy. Jenna whispered Mark’s, and loved feeling what her body could do to him. Even though she hadn’t had an orgasm, she wanted to kiss him and wrap her arms and legs around him – but of course, she couldn’t.
Then suddenly he was finished, breathing hard, body limp, laying heavily on her with his sweaty face beside hers. It couldn’t have taken more than two minutes since penetration! Quick, as promised – but, not what Jenna wanted or expected. As soon as Jake caught his breath, he lifted himself and pulled out. Her fantasy ended rather abruptly. Then, without a word he loosened the straps, unclipped her wrist cuffs, and left the room.
Jenna was cold, alone and abandoned – blaming herself for what just happened. She took a deep breath and sat up; removed the blindfold and cuffs; then went to the bathroom to clean herself up. He was in his room, door closed. What a cad! She was angry with her brother, and worried that he might expect it again. But, as she calmed down, she was glad her first time had been with him, rather than a boyfriend who’d soon be gone and forgotten.
Now, her thoughts turned back to Duke. She still felt the itch, wanting Duke to fuck her hard and long, then fill her with feverish doggy-cum. But this time she would ask me to help, which was exactly what I was hoping since I knew that once I helped her ‘train’ Duke, I’d get my turn.
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*see “Lisa and Prince – and Jenna”