A Date to Remember

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It started as her innocent first blowjob.
1.7k words
4.11
24.3k
11

Part 1 of the 3 part series

Updated 11/26/2023
Created 11/20/2023
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Katherine was 18 today, and for her birthday she planned to make the most of it. she had a small frame and stood just shy of 5 feet with perky A but working mentally towards B-Cup territory, she had long dark almost black voluminous hair and striking light blue eyes.

Iain was a good deal older, six years or so and whilst also carrying a small frame stood a skinny 6-foot 2" dark brown hair with chiseled good looks and unknown to Katherine at this stage a 10" cock.

He took her out for her birthday, the family would celebrate at the weekend tonight was their night. She wore a little sexy black number that hugged all her newly acquired womanly curves matched with the tiniest black thong, this complimented the landing strip shave she practiced weeks to achieve. On top of this she also wore a large faux fur coat to cover up as it was still a little cold out being March, plus her large nipples on top of her a-cups would give away her no bra outfit.

Iain pulled up in front of the house after their date like he'd done dozens of times before but this time it was different. Iain knew it and Katherines shy flirtatious looks confirmed it too.

The lights were out in the house. Everyone had gone to bed. That's a Monday for you. Katherine leaned over for a kiss as usual, but this time rested her hand squarely on his cock, she felt his dick was firming straight away with her touch.

"Oh, what do you think you're going to do with that?" She asked naughtily, not waiting for an answer she leaned in and stuck her tongue into his mouth rubbing her hand up and down his increasing bulge.

Iain the older more experienced one took it all in his stride letting Katherine do the work. Katherine was just maybe a too little impatient though, unzipping his jeans and pulling out his enormous but still semi flaccid cock out. She gasped and bit her bottom lip thinking. How the fuck was she going to take this monster in her tight virgin hole!? But... Maybe she didn't have to. She stroked it a few times whilst fingering her mouth seductively or at least she hoped it was. Iain smiled back and adjusted the seat back.

"That's my queue!" She thought to herself, tying back her long black hair, she licked her lips and leaned in. Iain closed his eyes with mouth wide as she took his head into her warm mouth, swirling her tongue around his tip. He didn't take long to get hard, and he gasped a little as the head of his cock pushed to the back of her throat, his eyes rolled, and he grunted happily as she worked up and down his length. "Nailed it!" She thought to herself, increasing pace now she started to bob her head up and down into his groin.

Her pussy was growling too, and she felt herself getting wet, she didn't have to worry Iain's fingers were working down her back over her arse & up her little skirt. She began to increase her depth a little more now making her slurping noises more aggressive along with the odd gagging sound from her throat.

As she took him deep against the back of her throat, he pressed a fingertip into her asshole making her squeal and gag on his member, he enjoyed that feeling as her throat gripped the head of his cock. Pulling back sharply and protesting to his fingering of that hole. Iain apologized and Katherine with a scowl resumed her position, this time Iain took that minor frustration out by investigating her very tight cunt with his finger. Her breathing was getting quicker and shallow, she was getting close to cumming but still wanted to please. Moaning, she took his cock deep as she could, gently pressed to the back and then down her throat, this she reckoned would be her party trick.

Iain's eyes rolled to the back of his head as he relaxed back into the car seat, the gentle rock of Katherines head into his groin accompanied by those delicious sucking and gagging sounds. He continued fingering and stretching her tender little slit whilst rubbing a second against her tiny clit, she was so deliciously wet now.

"Little girls have to taught how to please." he said, Katherine looked back at him responding with "I'll do anything you want, teach me how to please!"

"I want to see that cock disappear." Katherine leaned back in & took his cock deep to the back of her throat before gently pushing deeper. Iain had nearly managed to work finger to the second knuckle as he had wicked thoughts about how far he could push Katherines limits. Placing his hand on the back of her head he gently pushed her down a little deeper with each head bob. Katherine protested with her arms and hands, but he continued until her nose was buried in his bush and his cock fully down her throat. No other had managed this, Iain took pleasure as he pressed a different finger into her wet slit and the previously wet one her tight little asshole, with his hand on her head and her ass in the air she had no option but to accept her fate, Iain on the other hand grunted, happy to be in her throat balls deep, whilst his fingers were now knuckles deep. Again, pressing her head down over his cock her throat clenched his head, he rocked his hips and thrust his fingers into her a few times for good measure.

"WOW! God you're such a good little slut!" as she sat up and gasped for air. "Now, climb up here and kiss me. I want some of that wet pussy too!" Katherine was now flushed over her chest and face.

There wasn't much room in the front seat, but Katherine managed to squeeze over on Iain's lap, pulling her tiny knickers to one side she rubbed her wet little slit up and down the length of his cock. Iain pulled the shoulder strap from her left side revealing not only that Katherine hadn't worn a bra but her perky little tit too, considering her small slender frame and a-cups she had large erect nipples which Iain eagerly nibbled and sucked. The excitement now was almost too much, and she had to concentrate on not cumming too quickly, she didn't want to appear too eager, well at least not slut or whore eager anyways. But she was young and inexperienced and didn't manage to preserve any of the allure of dignity as an orgasm wave overtook her, now that slick little slit was a torrent. Iain felt his balls warm with her cum. She looked him dead in the eye, face even more flushed and red. She bit her as she quivered.

Iain had been teased enough and grabbed Katherine's ass before moving his hands underneath pulling her lips apart, ready to pull her down on his throbbing member.

"No, please. It's too big" She desperately pleaded with him. He ignored, but gently lowered her down she was tight, and Iain initially struggled to persuade his head not to slide up against her clit, with each slip she quivered more and more, repeatedly her cum gushed and ran down his length and over his balls.

Katherine reached down holding his enormous cock steady and his head against her hole, he popped inside all of sudden and Katherine squealed. Now she began to stretch a little more easily with each gentle thrust, Iain could feel his cock hit the cervix, but he had a good few inch to spare. She took control now and with short, shallow rocks from her hips she came again and again. Iain couldn't cum in her unprotected she knew; she'd already gone too far with a condom and so slid up and off.

"You need to get down there and lick all your mess up!" he said.

She did as he instructed and, like a woman possessed, licking and slurping her cum off of his cock and balls, she gave extra attention to his balls now taking each one into her mouth in turn and letting them pop out. Deciding she'd worked the boys enough she took his cock into her throat once more, as deep as she could, cupping his balls and giving them a good squeeze they pulled sharply away, but she grabbed them again as Iain placed his hand on the back of her head thrusting two or three good long strokes before holding as deep as he could, his cock pulsed before shooting his load down her throat. Katherine felt used but strangely excited by the experience. It wasn't how she'd imagined her first blowjob would go at all. As she sat up trying to look as sexy as possible, she realized she had a little cum dripping down her chin, Iain wiped it up with his thumb before pushing it into Katherine's mouth.

"You're a good little cumslut!." He said, Katherine blushed and swallowed the last of his salty cum. Iain sat back a moment and took in the sight of Katherine, her left breast on show, thong aside showing her trimmed pubic hair and ex-virgin hole gaping slightly with grool dripping down over her asshole. He imagined for a moment about sliding his cock deep into that little ass but decided to save that for another time. Iain leaned in for a deep long kiss and Katherine felt her swollen pussy throb.

Jenny, average build with long blonde hair the exact opposite of Katherine but with the same striking blue eyes was passing the front door when Katherine entered. She stopped momentarily in her plain nighty, looking jealously at the dribble of Katherines cum running down her inside leg. "You're going to be popular. Good evening, was it?" Jenny walked away as her own cum soaked her white panties, she'd enjoyed the show but was thinking maybe she could have future designs on Katherine's innocence too.

To Be Continued...

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Will527Will5275 months ago

Great story obviously written by a guy and from a guy's pov but a good story

zephyerzephyer5 months ago

Enjoyed it. Perhaps say who Jenny is. Sister, roommate?

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