The Initiation of Sherry
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Taste Of Sherry free porn video
Jake heard the front door open, followed by two voices raised in loud, drunken laughter. He shook his head and rolled his eyes. At least somebody is having fun on a Friday night.
Despite having broken up with his girlfriend almost a month earlier, he was in no hurry to get back into the game. Work and classes cut into his time, and he remembered all too well how hectic it had been the last time he was trying to find someone. With a few promising conversations going on the dating site he'd joined a week earlier, he was content to see if any of those panned out rather than trying to pick up girls the old fashioned way.
The old fashioned way had struck out with cheaters the last two times, anyway.
A thump and an exclamation of, "Oh shit," forced him to cover his mouth to avoid laughing out loud. It was one of the very few times he'd ever heard his mother curse, and hearing her do it after a drunken stumble into the wall was even more amusing. He was glad she was finally getting over the divorce, and assumed that she'd probably mellow after a while. For now, she deserved to have some fun.
The laughter grew even louder after the stumble, and Jake easily recognized the voice of his mother's friend Sherry. She was half Columbian, and because she spoke Spanish quite often around her family, she had a unique cadence that was easy to pick up on.
Concentrating hard, he managed to push the conversation and laughter in the other room out of his head well enough to study. By the time his empty glass caused him to put his book aside, the house had quieted. A look at the clock revealed it was after 2 a.m.
Grab another glass, check out Facebook, and hit the sack. Decision made, he picked up his glass and headed for the kitchen. Seeing light coming from the front room caused his brow to furrow at first, because his mother was a stickler for turning out unused lights. Then he remembered she had been stumbling drunk, so it wasn't so much of a mystery.
"Damn," he whispered at the unexpected revelation of Sherry asleep on the couch. Her skirt had ridden up in her sleep, revealing long expanses of gorgeous leg - and even a sliver of light cream color that had to be her panties.
Standing in the doorway, he drank in the sight and his eyes moved higher. It wasn't the first time he'd checked out her breasts. She had incredible tits, and he didn't care in the slightest that she probably had implants. This time, he had an even better view of them than normal. Her bra hung over the back of the couch, and she'd popped open a couple of buttons on her blouse.
With the perfect excuse of the glass in his hand and the only way to the kitchen going right past her, he couldn't resist a closer look.
Up close, he grinned as he was able to stare straight down her blouse at an ample amount of cleavage, perfectly illuminated by the lamp still burning next to the couch. He could even see the faintest hint of her right areola, and had to wonder whether her nipples were hard, or whether they just normally stuck out enough to tent her blouse the way they were.
Giving his half-swollen cock a squeeze, he headed on to the kitchen and filled his glass. Once again, he paused on the way back for another peek. Just as he was about to head back to his room, she muttered something under her breath, squeezed her left breast, and slid a hand between her legs.
He passed the halfway mark within a few seconds of that sexy display.
Common sense won out. Though she was obviously still asleep, a dream intense enough to make her touch herself might very well wake her up. That would leave him standing over her, sporting wood, and the glass of purple stuff from the fridge wasn't going to be sufficient to explain that.
He had to wonder what she was dreaming about as he walked back to his room. That wondering continued until it blossomed into a full-fledged fantasy. His erection never drooped for a moment.
Drink forgotten on his computer desk, he let that fantasy and his hard-on follow their natural course.
It was more than a little surprising to Jake when his mother started getting dressed to go out again the next evening. Considering how grumpy she'd been all day from a hangover, he couldn't believe she was going out for another round.
Sure enough, Sherry showed up, dressed in an even tighter skirt and top than the night before. Jake found it hard to keep his eyes off her tits and ass - so well displayed - especially in light of what he'd seen the previous evening, and what his imagination had eventually turned it into.
Fortunately, he had plans to hang out with friends, so he gave his mother a kiss on the cheek and made his escape before he got caught ogling her friend.
The night didn't go so well, though. Around eleven, both of his friends managed to hook up with girls, leaving him the odd man out. After an hour of that, he was done, and headed for home. The lights were out when he arrived, so he assumed that his mother either wasn't home yet, or had already gone to bed.
Since the latter was a possibility, he crept in the back door, which was the farthest from her bedroom, in hopes of not disturbing her. As he closed the door, he heard something that made him stop as he turned toward his room.
He couldn't quite figure out what he'd heard. If not for the house being almost completely silent, he doubted that he would have picked up on it at all. Curiosity pulled him toward the front of the house, since whatever it was had to be coming from that direction.
He heard it again the instant he stepped into the doorway to the front room, and all the mystery surrounding the noise vanished as he saw what was happening on the couch.
The lamp wasn't turned on as it had been the previous evening, but there was more than enough light filtering through the curtains for Jake to get an eyeful. Sherry was lying on the couch, her bra once again draped over the back. This time, her tight yellow top was pulled down - quite on purpose - showing off her breasts in all their glory. She squeezed and caressed them while her other hand moved rapidly beneath her panties.
Sherry whimpered again, her head lolling back and forth as she furiously masturbated a few feet away. Before he could fully process what was going on, she stiffened, her back arching up from the couch cushions, and let out a final, tight-throated whimper.
He couldn't help but watch her writhe on the couch as she climaxed, and waited just a little too long to duck back out of the doorway.
Sherry gasped and snatched her hand out of her panties when she saw him. A hurried tug only about half-covered her breasts before she lifted her hand to her eyes and groaned. "Well, this is embarrassing. Sorry, I thought you were out."
Jake grinned and said, "It's okay. Sorry I walked in on you."
"It's your house," she said, and let out a half-hearted chuckle as she sat up and tried to better tug her clothing back into place. "I'm sure the last thing you wanted to see tonight was old-lady boobs."
"Don't sell yourself short," he responded before he really thought about it.
She muttered something in Spanish and then added, "Flatterer." A shiver rippled through her, set off by an aftershock of her orgasm.
"Not at all." When he said it, she smiled, making him consider all sorts of interesting possibilities. One of those possibilities surged directly to the front, though. "Guess we'd better pipe down before we wake up Mom."
"Uhm ... She's not here."
That caught him completely off guard. "Huh?"
"She's borrowing my apartment for the night. Do you really want to know?"
Jake waved a hand in front of him and adamantly declared, "No."
They both laughed, but Jake was positive that he'd caught her glancing between his legs in the process. Tossing caution to the wind, he said, "Really, you have great breasts." He was rather proud of changing great tits to something less juvenile on the fly.
Sherry gasped. "Jacob, I'm twice your age."
Though she was obviously shocked, she didn't seem especially disturbed, so he pressed on, encouraged by the throbbing between his legs. "So? That doesn't mean you can't be hot."
"What would your mother think if she heard you talking about me that way?"
"Like you said, she's not here. I'm not going to tell her. Are you?"
"No." After a brief paused, she added, "So, I'm hot, huh?"
"Oh yeah." To punctuate the point, he reached down and adjusted his erection.
Sherry sucked in a sharp breath, and her knees snapped together. "Oh no. No, this is a bad idea."
Jake pushed off from where he was leaning against the door frame, walked toward her and asked, "What's a bad idea?"
"You're my best friend's son," she said without much conviction as he approached, her eyes gravitating between his legs.
"What she doesn't know won't hurt her," he said as he stopped, standing next to the couch.
Sherry looked up at him, her expression a mixture of worry and arousal. "I ... We..." She closed her eyes for a moment, shivered, and then reached out to trace the lines of his erection with her fingertips. "Oh my god."
Jake groaned from the feather-light touch, and couldn't resist when the play on words popped into his head. "I know I'm not 21, but are you going to tell Mom if I have a taste of Sherry?"
She rolled her eyes and shook her head, but followed it up by crooking her finger to beckon him closer while tugging on his belt loop.
As he sat down, Sherry demonstrated that any shred of inhibition she might have felt was gone. Once again, she tugged down her top, leaving her breasts supported by the stretchy yellow material.
Seeing her breasts bare and up close confirmed his suspicion that she had implants - not that he cared. The globes were firm and rounded, rising and falling with her quick breaths. Her areolae were light brown ovals decorated with numerous bumps, surrounding erect nipples that were far lighter in color, with hints of pink.
"So you like them?"
"Love them," he answered, and then showed her by leaning in to suck her right nipple between his lips.
Sherry gasped out something in Spanish as her hand came to rest on the back of his head. He only sucked on the one nipple for a few seconds before switching to its twin. She tugged him toward her, and he took that as an indication to suck harder. When she moaned in response, he knew he'd hit the mark.
Back and forth he went, sucking and teasing her nipples with his tongue. Her moans grew louder, and her fingers twined into his hair. Then her other hand slipped between his legs. She squeezed him, making him groan around her nipple.
"I want to see you," she said in a breathless voice.
Jake let her nipple go with a final slurp, and then sat back to unbutton his jeans. Sherry immediately reached for the tail of his shirt, tugging it upward, and as soon as he had the button unhooked, he took over, pulling the shirt over his head.
"Oh my," she said as she traced the lines of his abs. Then she looked up into his eyes, offered a sultry smile, and let her fingers glide downward, brushing over the swollen head of his cock, hidden beneath brick-red briefs.
A tug on his lower pant leg caused him to lift his foot, and she grabbed his heel, holding it in place while she untied the laces with a quick pull. His shoe thumped to the floor, sock landing atop it a moment later, and after he crossed his opposite foot over to her, the second shoe and sock followed.
Sherry slowly tugged down on his zipper, his erection parting the denim as each tooth came unhooked in turn. When it reached the bottom, she slipped off the couch, grabbing his pant legs as he lifted his butt and pushed from the waist. She'd barely dropped his jeans to the floor before her fingers slipped beneath the waistband of his briefs.
Once his underwear joined the rest of his clothes on the floor, she leaned over him with her hands on his knees, breasts hanging down in an eye-catching display. "You are a big boy," she said before sinking down to her knees.
With her tongue creeping up the length of his shaft, Jake growled and dug the fingers of his right hand into the edge of the cushion. She tickled the head with the tip of her tongue for a second upon reaching it, and then curled her fingers around the root of his cock to stand it up.
"Ah, fuck yeah," he groaned as she wrapped her lips around him.
She cupped his balls in her hand, fingers moving in a slow, rhythmic wave. Her tongue swirled around the head of his cock, tracing the ridge and teasing the slit at the tip. All the while, she looked up into his eyes with the most hungry, sexy expression he'd ever seen in his life. The tease only lasted a second or two before she closed her eyes and took him deep.
Jake grunted as her lips slid down his shaft. In that first suck, she easily took as much of him in as any other girl he'd been with had managed. Her lips touched the fingers curled around the base, and then slid back to the tip.
"Good?" she asked, her lips still brushing the head of his cock. She engulfed him in her hot mouth again without waiting for an answer.
"Uh huh," he said in a rush.
She took him in for a few slow, deep strokes, and then asked, "Better than those little girls you've been with?"
"Way better. Fuck, you know how to suck a dick."
"I love it."
Her next suck was a lot quicker, harder, and just as deep. Jake couldn't hold back his grunts and groans as her head bobbed over his lap. The dark curls framing her face and gold corkscrew earrings bounced as she sucked him like no woman ever had before. His hand moved to the back of her head, and only her warding hand wrapped around his cock kept his bucking hips from pushing him into her throat.
After only a couple of minutes of the incredible blow job, he felt the itch building in the head of his cock, spreading down the shaft toward his tightening balls.
She must have sensed it, and let him slip free of her lips with a wet pop. She stroked her hand slowly at the bottom of his shaft and asked, "About to come?"
Feeling more than a little self-conscious, he nodded and said, "Yeah."
"Mmm. I love making a man lose control. You're young. You'll get hard again in no time. Give it to me."
He didn't have much choice. From the moment she took him back in her mouth, it was a struggle to hold back. Despite what she'd just said, he was bound and determined to last as long as possible.
He made it almost a full minute.
Sherry's moan vibrating through his cock when the first blast of cum filled her mouth set off another spurt in short order. He grunted, gasped, and breathed hard as she sucked on just the tip, slowly pumping her hand to milk out every drop he had to offer.
His hand was trembling when he pushed her away, unable to handle any more. She let him slip free and moaned again while looking up into his half-lidded eyes.
"H-holy shit," he managed to say as he went limp.
"Mmm. That was a lot." She gave his cock a squeeze.
Jake grunted and lurched, a final dribble bubbling up to run down the head of his cock. An embarrassing, high-pitched sound burst from his lips when she darted in to gather up his cream on her tongue.
She chuckled and licked her lips as she reached under her skirt to press her hand between her legs. "Oh that made me so wet."
Trish
- 13.10.2022
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