Orgasmic Oblivion - Big Ben

This is an anthology series where in each story a person gets caught by others during their most vulnerable moment: mid-orgasm. There's no time to stop, cover up, or deny. Pleasure and embarrassment all at once. Enjoy!

These stories are not necessarily connected. They merely share the same theme.

All characters are 18 years or older. Some of the main characters are inexperienced and/or sheltered in conservative families but they are all young adults.

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Ben Wilkinson lived in a modest apartment home with his mother, Laura, and his twin sister, Stephani. The place was so modest that the old brick building had no lawn accompanying it, as it was originally a warehouse.

Rather, it was nestled right against the sidewalk. People could be heard milling about just outside the windows throughout the day.

That was alright with Ben though. In fact, it added something extra for him when he'd spend some 'personal time' in his bedroom. A little harmless thrill, if you will. Such was the case this afternoon.

You see, Ben Wilkinson was a bit of a classic nerd. He was tall and lanky, and so nearsighted that he always wore glasses. His only distinctive quality was his rather large penis, which the boys in gym class ended up nicknaming him 'Big Ben' for. He was a show-er at 8 inches soft and more than 10 inches erect.

His girlfriend of many years, Becky Thompson, was as shy around boys as he was clueless around girls. They were together out of convenience and familiarity more so than mutual attraction. They barely expressed more affection than holding hands.

She had no idea about what he had under his clothes and he had no idea how to properly introduce her. Unfortunately but not unexpectedly, she just left his side moments ago, as insisted on by his mother and sister when they went to their racquetball class.

So, here he was, alone in his bedroom again, naked and next to his window. He was ready to get his rocks off as he peered through the blinds and watched strangers and neighbors walk past, unaware. For extra spice, he kept the window itself wide open. The blinds were the only barrier. It was a challenge to stay quiet.

He hefted his mighty meat in his right hand and it slowly stirred to life. Pulling down a bit of the blind with his left hand, Ben peered out and saw his mother and sister stretching and chatting as they prepared for their workout. Clad in sports bras and skin tight shorts, the pair could almost be mistaken for twins.

He'd never openly admit it, but Ben thought they were very sexy when dressed like that. It was easy to imagine them naked, and that always made him hard. He began to stroke his velvety shaft as he watched their every move. That is, until they jogged away moments later.

The Wilkinson's housekeeper, Senorita Abigail, then came up to the front door and let herself in. She was an older, but still very attractive, latina milf that was the star of many of Ben's wet dreams while growing up. While now in her early 50s, she still seemed to have a body to die for, and her outfit showed it off well, not to mention the sway of her hips.

Ben could hear her begin to clean while speaking with Becky as she was presumably leaving. He imagined Abigail was seducing Becky instead and ravishing her right there on the living room floor, with the front door wide open to the neighborhood. He stroked his big cock faster, lubing it up generously with precum.

Looking out the window again, he saw across the street a father helping his son pack up the family car for college. While the mother stood nearby in tears, the father was taking it in stride. Obviously proud of his boy, he put on a brave face. Ben would've smiled and appreciated the sweet moment any other time, but with the current situation, his mind wandered.

He imagined instead that the father finished packing by hugging his son and pulling off the boy's shirt, then neatly folding it and putting it in the trunk. The older man then dropped to his knees and pulled the boy's pants down, helping him step out of them, leaving the young man naked there on the driveway as his mother stepped up.

While she gently gathered up those remaining clothes and put them in the trunk with the shirt, the father dutifully began to suck his son's youthful dick, bringing it to life with fervor. Ben didn't know if he wanted more to be the son or dad but he fucked his fist faster regardless.

He imagined the mother moving up along side her husband and giving her son a hug with one hand, soft kisses on the cheek, and pushing on her husband's head with her other hand, making him gag on her boy's fuck-stick.

'You're gonna miss when Daddy deepthroats you, aren't you, baby?' she said, smiling through the tears.

The boy nodded and grunted, holding his sweet mother tighter, as he shook and came in his father's mouth.

'Atta boy!' his father said while laughing. He smacked his son's ass playfully and stood up, giving his wife a cum coated kiss. 'Let's go!' he said, climbing into the driver's seat.

The boy staggered into the backseat behind his father, and the mother sat on his lap. As they began to drive away, her dress flew out the window and she could be seen nude and bouncing on her son's lap, still crying but also now moaning.

Ben was close. Very close. He used both hands to fuck himself now. He thrust his hips back and forth. It took all he had not to moan out loud.

He looked out the window one more time, leaning on the blinds with his shoulder to open them. He saw his mom and sister jogging back toward the house, their breasts barely contained in their bras and their cameltoes very evident.

Then an unfortunate set of circumstances happened all at once.

First, Big Ben Wilkinson started to orgasm. And not only was his cock big, but so was his cum. There was a lot of power behind it.

Second, he leaned too heavily on the blinds and they came crashing down, falling completely out the open window, startling those outside and leaving him bare to their eyes and spraying jizz all over himself and the window.

Third, the ruckus sent Abigail and Becky running into his room to make sure he was okay. They opened his door and he jumped, turning to face them. His bare ass faced the window now.

In his surprise, his hands and legs were spread wide open awkwardly. The two gorgeous women got to see his big prick jump the last few times, shooting and then dribbling it's white, sticky goo on the floor in front of them.

Poor Ben was covered in his cum. The first shot had hit his face and covered his glasses. Then it had landed on his chest, tummy, and finally his thighs. Even if he had the smarts to cover his junk in time, there was no denying what he'd been doing. He couldn't hide all of it.

His mother saw! His sister saw! The family across the street saw! Others walking by saw! Abigail saw! And most importantly and embarrassingly, his now wide-eyed girl Becky just saw!

As this huge revelation hit him, he thought he might pass out, and he hoped he'd die. But instead, he felt a cool hand on that meaty cock dangling between his legs. It was not his own hand, but one that reached through the window. Looking down, he saw the skin on it was aged with wrinkles.

'Oh my God!', Becky exclaimed, her hand over her mouth.

The stranger's hand pulled his big cock back behind him, and he instinctively bent forward at the waist, both to avoid too much tension on his tender organ and to get a glimpse of who was groping him. It crossed his mind briefly that he was starting to get excited again.

To more of his surprise, the hand holding Big Ben belonged to his elderly neighbor, Mrs. Watson. The feisty widow was in her early 80s but could easily pass for 60 if not for her snow white hair. She'd made it known on several occasions she could be his Mrs. Robinson if he wanted. He'd always politely refused.

The moment she wrapped her warm lips around his still dripping head, the thought of refusing her advances left his mind. He'd never had a blowjob before, let alone one from behind or very public to boot! He moaned loudly.

Ben could hear screaming or loud speaking voices in the far flung distance, perhaps from his family or his girlfriend, but all he knew right now was the incredible warmth and sucking going on around his cock, and the feel of his neighbor's nose against his balls. Little else mattered.

He was hard again. So hard it hurt and was awkward to fully enjoy at this angle. But that wasn't going to last long anyway. His neighbor knew her business and he started to cum again in moments.

One shot went into her mouth before his mother and sister pulled her off of him and back a couple steps. The next rope of sperm landed across her face, as well as the other two women's chests.

It seemed like Mrs. Watson had put up a fight, as both Laura and Stephani each ended up with one breast bared, and his mother's shorts were nearly torn in two. His spunk dripped from his sister's nipple and in the brief second he had to notice, Ben thought he glimpsed Laura's clit, big and poking from it's hood, excited.

At the same time this was all happening, Abigail and Becky had come up to him in front to pull him away from the window. The older woman was standing at his side, holding his arm. Becky, meanwhile, had knelt down in front of him to push the neighbor away.

When his monster was freed from the face hole captivity behind him, Ben started to stand. Still mid-orgasm, his cum splattered right up the middle of his girlfriend, from her crotch, to between her soft, pillowy tits, and all over her face. The juicy cock-head landed squarely in her shocked, gaping mouth.

Abigail, having not fully understood what just happened, mistook Ben's moans of pleasure for pain. She continued pulling her employer's son forward, away from the window. This essentially caused Becky to deep throat him and she had to swallow the last of his sperm in order to breathe. Fortunately, he was very spent and was getting soft quickly.

He finally just collapsed to the floor from exhaustion. But even then, in that final moment, he was awkward and clumsy. He managed to trip Abigail on his way down.

The last thing Big Ben Wilkinson saw then was his housekeeper's well groomed, sweet smelling, now wet pussy landing on his face. Apparently she went commando.

The last thing he felt before passing out was Abigail riding his face for all she was worth. He could also feel her leaning back in ecstacy and pulling Becky up and over to grind her crotch on his, whether she wanted to or not.