Painful Pleasure (anal destruction)

Olivia excitedly sits in her bed, eagerly waiting for Jake to come out of the bathroom. Her heart thumped loudly in anticipation. Today, They were going to try one of her new fantasies, doing another sexual exploration, anal sex. Her eyes dart towards the door, as Jake enters the room. He was butt naked, body dripping with water droplets, his wet hair falling on his forehead.

Her inside twists, feeling herself getting all needy for him. He walks towards her with a wicked grain, hand already stroking his half hard length. She gulps at that. He was big, too big to be put in her ass. It always hurt like a bitch at first whenever they have sex, but it was always vaginal. So, she was quite nervous to try anal. He stops a few inches away, pushing his cock into her mouth, without a warning. Her pink lips wrap around his member. She starts with swiping her tongue around the head, teasing its spit, by pushing her tongue against it and then gently starts sucking it, her hand playing with his balls. Jake throws his head back, groaning in pleasure.

She keeps sucking him like some lollipop, her movement getting aggressive gradually, driving him to the edge, until he pulls it away. the veiny cock leaving her mouth making a pop sound. "Get up." Jake commands. She complies, standing up. She had discarded her clothes earlier too, so her own body was at display for him. He gawks at her body with lust. Inching closer he pushes his mouth against her, a gasp leaves her mouth as she feels him pushing his wet muscle into her warm cavern.

Jake kisses her messily with drool spilling over their chins, their tongues busy sucking and sliding against each other. He finally pulls away. "Get on your knees." He says in a deep voice. She climbs up the bed, before making the position. He gets on the bed too. Eyeing her bubbly butt, he grips her soft globes in his hands before parting them to take a better look at her asshole, stuffed with a big size butt plug. The cone shaped plastic snuggled deep inside her, the walls of her hole stretched around it.

To make sure, she would be able to enjoy the experience she had been experimenting with the buttplugs for days. He traces the outline of her hole with his fingers making her shiver. Suddenly, he grasps the base of the plug and twists it slowly before giving it a gentle push deeper inside her. She lets out a loud moan at that. He again pulls the plug outwards before pushing it inside, making her body jolt with pleasure. He continues to do that for a few times watching her walls clench around the plastic toy. Now, lowering his face to her ass, he licks a stripe from the bottom of her ass's crease to her glistening hole. Nose pushed against her flesh, as he swipes his tongue against her rim.

Her loud moans make his veiny cock grow in size. Again, sliding his tongue up, he teases her hole. Her body trembles with pleasure. He continues eating her out, savouring the taste of her ass. Then Flipping her, he makes her lie down with her legs wide open. Her shaved pussy on a clear display for him. The entrance, spilling out her juices as it clenches around air.

Again, lowering his mouth he blows some air on the girl's pussy before lapping onto it like some hungry animal and sucking it crazy. She screams out of pleasure. He sucks her labia, tugging them with his mouth and pushing his tongue against her clit. His tongue sliding against her flesh. Her mind goes blank as she lies there, letting him do whatever he wants. He pulls back, chin glistening with drool and her cum, wiping it with the back of his hand. He now focuses his attention back to her asshole, and without any warning, he pulls out the buttplug.

Olivia's whole body convulses as she screams feeling pleasure and a little pain at the same time. Her hole stretches wide, as the plugs slide out of her. He looks at her loosened hole clenching and unclenching around air, begging him to fuck her senseless. He runs a hand down the length of her delicate spine and spreads her ass cheeks wider. Reaching for a bottle of lubricant, he liberally applies it to her small puckered hole, laughing when she tries to squirm away as the cool liquid coats her sensitive flesh. Fingering her gently, he spread the lube around and in her untried opening, allowing it to warm and cover her completely.

 Sliding one finger inside her, he traces the ring of her entrance, coaxing the hole to accept first one then a second finger. He scissors them, back and forth, stretching her with a careful determination, adding more lube to make sure she was slick and prepared for him. He did the same to his cock, making sure his entire length was coated in the slippery liquid. His cock was painfully hard now.

Finally, gripping his neglected member he brings it to the opening of her ass. Pushing the reddish head slowly into it, he grunts as a wave of pleasure washes over his body. Olivia grips the bed sheet tightly as she feels the foreign feeling of getting stuffed with a huge dick. Her asshole clenching around the man's cock trying to swallow it in. Jake pushes his whole length inside her until his balls rest against her ass crease. He waits for her to adjust to the feeling. When he notices her bringing her hand towards her pussy, he takes it as a signal to move, seeing how she enjoyed the feeling.

Starting slow at first, he pulls his length before pushing it back and repeating it until she starts moving downwards trying to fuck herself with his cock. He increases his pace, as he begins to thrust inside her, feeling her inner muscles milking him in a vise grip. He wraps an arm around her delicate frame to push harder. Her hands are still playing with her pussy as she moans. He increases his speed, holding her legs on his shoulders as he mounts her with an animalistic pace. Her hands, pulling her pussy lips as she cries, overwhelmed with pleasure.

One of his hands now moves towards her breasts as he squeezes one of them. Her hands fall limp on her sides as he starts playing with her breasts, the pleasure getting too much for her. He cups her soft globes, compressing them and then pulling her pink buds, pinching them with his thumb. She shakes as he continues fucking her against the bed. He lowers her legs to his both sides, leaning downwards towards her body. His mouth now close to her big boobs, he bites onto her hardened nipple.

She clenches around him suddenly. He continues sucking and biting her breasts, as he thrusts into her asshole. She begs him to go faster, his mind going hazy as he complies, moving fast like a madman, giving in to her demand for more. She grounds her hips back against him and he meets each thrust with a surge forward of his own. He fucks her hard and fast until they were both crying out in release. Jake pumps his hot semen deep inside her, groaning as her tight hole tries to milk him for more. His body convulses as he dumps his cum inside her. Her body shakes as she lets out her pussy juices too. Body's trembling with orgasms. She sighs at the feeling of his hot semen inside her ass. The hot cum filled her up to the brim. But he was still not done, he takes out his cock, cum drips out of her ass. He raises her legs, asking her to hold them. Her body now bent and ass right in front of him. He pushes his lips against the gaping hole sucking out the semen.

Her pussy throbbing at that. He pushes his tongue inside her gaping hole, tasting her, sucking the swollen rim, and biting on the flesh. Finally cleaning her asshole, he moves away, Olivia's body heaving up and down as she lies there tiredly. He then moves his mouth towards her pussy, eating her out. Her hand grips onto his head pushing it even more towards her pussy. He hums, swallowing her cum. Tongue sweeping her clean. She tightens her grip on his head when she feels him, pushing his tongue against her clit. He plays with it, grasping it with his lips, sucking it gently before finally retreating away. Olivia's body still is not over the orgasm as she continues shaking. Sweat covering their bodies, as they sit close to each other. She opens her eyes, looking at him. Her face adorned with a smile. This was definitely a worthwhile experience.

"Ready for round two?" He asks, playing with his limp cock which had started getting hard again. Before she could answer he's already pushing inside her loosened hole again.