Kyle's Lucky Night

Kyle and Cole had been friends for a long time, being neighbors helped. But Kyle was more focused on Cole's sister, Mandy. Mandy was 23 and home for the holidays. Kyle had just turned 18 and thought this was his chance.

One night he was sleeping over at Cole's when Mandy walked into the living room declaring, "I'm tired, I took my sleep aid and am going to bed. If you wake me you are seriously dead." 'She was so pretty, even tired', thought Kyle.

Cole and Kyle continued to play video games until they were tired as well. Cole fell asleep on the couch leaving Kyle the floor. But Kyle kept thinking about Mandy. 'Well I can go up to her room and just peek in on her right?' he thought. So he sneaked up the stairs and into her room.

There she was in just a long night shirt, probably her dad's old shirt. The sheets pushed off of her; she was gorgeous. Kyle moved closer and stuck a hand out to touch her. He felt her face, trying to see if she would wake. Kyle patted softly trying to wake her. When she didn't so much as twitch, he was emboldened. He grabbed her right boob and massaged it a little. Mandy didn't move, the sleep aid had truly knocked her out.

Kyle grew braver and lifted her shirt over her body, exposing her panties and wonderful boobs. He admired her soft plump beasts, with nipples soft but slowly growing hard in the chill open air. He took one in his mouth and sucked it, biting lightly on her nipple. And still she didn't move.

Kyle was rock hard now, he took his dick out and began to jack off. An idea hit him. He slowly lifted Mandy's hand and curled her fingers to grasp him. He started slowly moving her hand to jack him off. When the pain from friction became too much he stopped to lick her hand. The added spit helped ease the process and he sped up. He loved it so much he grew even braver.

Kyle repositioned himself near her head and slightly nudged her head to roll over. Ever so slowly he repositioned her so that she was facing his dick. He rubbed his spit and precum covered cockhead over her closed lips. Needing to feel her mouth, Kyle pinched her nose causing Mandy to open her glorious mouth to breathe. Taking advantage of this, he placed his dick in her mouth.

To his surprise, Mandy began to slowly suck on it. 'She must be dreaming,' he thought. Kyle began to slowly force more of his dick in her mouth, careful not to gag her. He had got a rhythm going when he felt he was about to come. He quickly pulled out, not ready for that yet. He was feeling a little ashamed of himself at this point, but Mandy let out a soft sigh snapping her mouth a few times. She shifted slightly in her sleep, rubbing her legs together. She smiled seemingly enjoying her dream. This brought Kyle's eyes to her lower body, his hard cock jumped at her tightly covered pussy.

He now moved down her body, slowly dragging a hand down across her chest, down her belly, circling her thighs. Slowly and carefully he removed her panties. Shaved! She was cleanly shaved. It was beautiful. Kyle leaned in and smelled her beautiful cunt. He came in that instant. He freaked, quickly cleaned up and put her clothes right. He went back downstairs, very happy.

A few nights later, Kyle was back at Cole's place. They were playing games when Kyle thought to innocently ask, "Where's Mandy tonight?"

Cole, not looking up from the game, replied "Sleeping."

Kyle smirked, "Oh gotcha. Did she threaten your life if you wake her again?" He laughed trying to act normal and not overly interested.

Cole scoffed, "Yeah, she always does when she takes a sleep aid. I think if she wakes up she doesn't go back to bed on those things. To be honest though, she sleeps like a fucking rock with them." Cole laughed and Kyle joined. "Don't you remember like 3 years ago, when we broke my closet door while goofing around? She didn't wake up then and we were like seriously loud."

Cole and Kyle laughed, though Kyle did feel a spike of shame at what he did just a few nights prior. His shame though did not outweigh his horniness. After Cole fell asleep, he was definitely going upstairs to see Mandy.

Kyle was almost all the way hard thinking of Mandy by the time Cole was completely asleep. Playing games and getting ready for sleep was difficult with a half chub, but he made do.

Now Kyle was again standing at Mandy's bedside. She was in another night shirt, smaller than before. It rode slightly up already over her belly button. Kyle slowly lifted the shirt higher, above Mandy's ample chest and hooked it under her chin. He cupped her boobs and slowly sucked a nipple into his mouth. He switched nipples back and forth until both were hard and standing at attention.

Kyle knew that Mandy would not wake, even through movement of her body. He felt so bold and wanted to play with her for a long time. He carefully moved Mandy to lay flat along the edge of her bed. He moved her arms above her head and placed them bent at the elbow with hands under her head. He moved her legs flush together. Mandy looked as if she was relaxing on the beach, tanning.

After admiring his work, Kyle stood parallel to her chest and swung a leg over her body. He rested his knee on the other side of her body, straddling her. He lowered himself down on her, shifting her boobs to envelop his dick. He started to slowly thrust into her ample breasts. It was glorious. He spit down to add some lubrication and moved faster. His dick bumped Mandy's chin every other thrust, which sparked an idea.

Kyle rose back up and carefully removed Mandy's shirt. It was difficult getting it over her head, but he accomplished his goal. He then propped Many's head, chin down using her shirt, pillow and hands. He opened her mouth slightly. Kyle tested her previous night's sucking by slipping his thumb in her mouth. After a few thrusts Mandy began sucking. Kyle almost came right there. He then repositioned himself between her boobs. He continued to titty fuck her chest, while every thrust pushed into Mandy's mouth. He had to use shallow thrusts to keep the head of his cock in her mouth but it was worth it. He lost himself in the feeling and too soon he came in her mouth.

Shocked Kyle quickly backed away and froze. He was frozen above her belly with the leg on the bed braced to run. Mandy choked a little and spit out his cum down her chin. She ran her arms over her face, spreading the cum and saliva mixture all over her face and neck. Once she resettle, Kyle noticed that Mandy was still asleep.

"Holy fuck!" Kyle breathed out. He couldn't even feel any shame. That was too hot for words. Kyle knew he was spent but his dick was giving a valiant effort to get up again. He laughed softly at his cock and began to carefully clean up Mandy with her shirt before trying to carefully put it back on her. By the end of his efforts, his cock was at half mast. He decided that he could extend his fun.

Kyle moved down the bed to Mandy's pussy. He decided to move the girl horizontal so that her legs were off the bed, ass at the edge. After slowly rearranging her, Kyle set work to removing her panties. Mandy's hairless cunt was just as smooth to the touch as it looked. Kyle slowly parted her lips and took a quick taste of her pussy. He drew his tongue from the skin between the asshole and vagina all the way up to her clit and moved his tongue around the hard nub. He circled her clit a few times more. Mandy have a soft sigh and bucked her hips slightly.

Kyle checked that she was still sleeping. She had a soft smile and looked a little sweaty but was sleeping all the same. Kyle smiled and dove back into her cunt. He focused his tongue on her clit while moving his right hand to her hole. He slowly fucked one finger into her in rhythm to the flicks of his tongue on her clit. Kyle could see and feel her thighs trembling. Mandy's hips were softly bucking off the bed; Kyle was taking her apart.

Soon enough, she was easily taking 3 fingers. It was amazing. He switched from flicks and circles of his tongue to just laying it flat against the throbbing clit. His left hand worked his own cock while the right continued to fuck into Mandy. All of a sudden Mandy was groaning and giving a soft grunt with every thrust. Her thighs flexed, hips lifting off the bed and she came. Kyle removed his fingers, but left his tongue flat on her clit. When she began to calm down and was breathing deeply, he moved his tongue to taste all her cunt. He licked at her outer lips, the inner folds, around her hole and carefully in her. He licked her clean as he jacked off.

Kyle was really close, so he stood and jacked off quickly over Mandy's pussy. He came with a groan and shot his load over her thighs and cunt. He even managed to hit her belly button. He rubbed his dick up and down her spent pussy. Kyle pushed his quickly softening dick right in her hole and thrust a few times, completely emptying himself into her. Kyle let his softened cock remain in her warm wet cunt. He braced himself over Mandy, face to face. Kyle gave her a quick kiss as to say goodbye before removing his dick. He quickly cleaned and repositioned Mandy before hurrying down back to Cole.

God he was tired. He felt like he could sleep for ages and not wake up.