Tinder Date (Patreon)

Here is a new short story I made, calling it Tinder Date. Might have an alternate ending in the future, but here it is hope you all enjoy.

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Luke looked at himself in the mirror and smiled. Revenge was a dish he would serve hot. Luke was in a button down black short sleeved shirt and a nice pair of jeans. He had even combed his hair. While he was still a bit gangly, he was not the small dork he had been in high school and community college. He was a man, a skinny one with dorky hobbies but still a man.

That was what this date was all about, proving he was a man. Not just to himself but to the one woman who called his manhood into question growing up. Growing up Luke had been short and tiny; he was called Little L on more than one occasion growing up. He was bullied a lot, and the list would be too long to get revenge on them all.

The lead bully who made his life a living hell was one Sarah Gage. She was tall, strong and mean. She had been the most popular girl in school and developed earlier than anyone else. Every guy had a crush on her, and few were even permitted to hang out with her. She had been a track star in high school and college, as well as playing on the softball and basketball teams.

Since Luke could remember she had bullied him. School, camp, the neighborhood it didn’t matter. She had run the gambit of bullying on him with no end in sight. She had gone from tying his shoelaces together during kickball to firing paintballs at him during graduation. Or filling his locker with fart spray to super gluing him to a wall. Sarah had done all that and everything in between.

She of course used the classics, not a day went by till he transferred out of community college did he feel her wrath. Indian burns and swirlies were the least common, but she still managed to fit them in the rotation. The top three of course went to purple nurples, Sarah had an eye for aiming at the nurple through a shirt. Pantsings, which she had perfect long before the reached college and put that perfection to good use. And of course, the granddaddy of them all, wedgies. She used those multiple times a week and different variations for Luke. Even after his growth spirt, she still managed to outpower him and leave him with his undies yanked on.

It had been a few years since that last one, long enough for Luke to have filled it out. No longer the sleight nerd, he was now a slightly taller, slightly in shape nerd. He was still called gangly but not a string bean anymore. He looked good, if he did say so himself.

The past few years since seeing Sarah had been fruitful. He had gotten a great job at a tech start up, got a good house and did well with the ladies. He had kept his dating ups and alive. He was swiping late one night when whose face popped up onto his screen, Sarah Gage. She was just as hot as ever. He couldn’t help himself, even if she bullied him relentlessly, she was a hottie, and his baser instincts took over. He swiped right and low and behold, she had matched with him.

She started messaging him before he could even think of what to say. To make matters even more interesting, as he talked to her, he realized she didn’t recognize him. Sarah had no idea that Luke was the boy she had bullied for years. She had no clue, even when he tiptoed closer to their past. As Luke realized he had a chance to do over an evil idea began to creep into his head.

What if he got revenge?

She had humiliated him daily, what if Luke could get her back, just once. It had to be the perfect move and the perfect time. She had done a lot to him over the years, but one stood out among the rest. The wedgie. She had stretched his undies seven different ways from Sunday, and it would be his move to get her back with.

She would be unaware of his motives. It was clear she was interested as they exchanged messages daily. A few close calls when she asked where he was from and where he grew up, but Luke avoided those expertly. They eventually reached the most important part of the plan; she asked him to go out. Luke agreed within a heartbeat, not caring if it came off as desperate.

They agreed to a date at a quiet local place. Luke made reservations. He spent half the time planning his actions after the date and half spent worrying about what would happen if she didn’t show up. These weeks of planning could be for nothing. He got there fifteen minutes early before going in, he had just managed to get into the restaurant when he heard a voice behind him.

“Luke?”

He turned and it was Sarah calling his name. Unlike in the past there was no fear, she was calling upon him for some humiliating task. Now they were equals.

Sarah was just as hot as he remembered. She was tall, athletic with a beautiful face and long brown hair that she currently had up in a bun. She still made him feel nervous as she was the girl who could kick every guy’s butt from the gym to the classrooms. She was in a slinky black dress with black heels that made her slightly taller, not that it bothered him.

“Hiya, Sarah.” He said and there were a few moments of awkward introductions. Before Luke knew it they were being led to a table and a whirlwind of words and he was having the time of his life. Sarah was, for lack of a better word, nice and wonderful. She was interesting as she was a traveler. They talked about work, lives, friends, interests. It was honestly on pace to be the best date of Luke’s life.

They ate, they talked, they drank. It was wonderful. Eventually Luke excused himself to go to the bathroom. In there, alone with the mirror he looked into his own eyes. This woman, who had made his life hell, she was so compatible with him. Could he actually go through with it? Could he ruin this date by getting revenge?

The answer was yes.

He steeled himself. The plan wouldn’t fail. Tonight, Luke was going to be the one to give the wedgie. He splashed a little water on his face and left the restroom ready to seal the deal. He barely made it a step before he ran into Sarah. He awkwardly tried to move past her when she grabbed him. She moved her head close to his shoulder, breathing sexily into his ear. He could feel his arousal growing from just these few seconds.

“I’m wearing those pink panties I told you about.” She whispered into his ear and Luke thought he might pass out. The pink panties in question, which he had never seen but she described as her most cherished embarrassing item was a pair of hot pink boyshorts that had given her good luck since she wore them when going through Rugby team initiation. He hadn’t gotten the fully story only that they were lucky, and she said she looked drop dead sexy in them.

Luke spent the rest of the evening debating what to do. Sarah was amazing, but she had made his life hell. He could get revenge, go home, or even maybe try and get lucky. The date was wrapping up and Luke still wasn’t sure what to do. He paid the bill, and they slowly left the table. She grabbed his hand as they walked out into the parking lot, and he knew exactly what he was going to do.

Luke was going to do the chivalrous thing.

“I had a real fun time tonight.” She said as they walked through the empty parking lot. HIs car was at the far edge of the lot, all alone and secluded.

“Me too. We should do it again.” He said he was not sure what else to say.

“It doesn’t have to end.” Sarah offered and Luke froze. He wanted to say yes, besides for the revenge maybe just to get lucky, but he knew he had to do the right thing. He turned to face her.

“I had a real fun time tonight and we should do this again, but I think it is for the best if we call it here.” He said, almost not wanting to hear her disappointment. She didn’t say anything but dropped his hand. Luke turned to go, hoping to text her and maybe explain a bit why he was acting so strange on the best date of his life.

Something stopped him, held him back from leaving her.

It was her hand down the back of his jeans. First one hand then the other he could feel as her manicured nails wrapped around the waistband of his underpants. He froze, his mind couldn’t believe that after all this he had fallen into some kind of trap. Once again, he was her plaything.

“I see still just a wedgie boy.” Sarah said low into his ear. He was somehow both afraid and aroused at the same time. He didn’t have time to appreciate either feeling as soon as the last syllable escaped her lips, she forcefully pulled the white cotton out of his pants, up his back and between his crack. His hands went to his crotch as whatever arousal he had gotten from her words disappeared as the fabric was pulled tight against his crotch.

Luke was on his tippy toes as Sarah forced the white briefs even higher up his back. She hadn’t lost the skill as he was beginning to taste cotton and could feel the fabric leaving no give or stretch as she forced it higher.

She held the delicate briefs with more fabric than waistband as she continued to lift higher. Luke knew something was going to give and it was going to be his undies, just like it had always been. He leaned forward trying to put pressure on his crotch which was in extreme pain from the tightness of the fabric.

She saw this as her opening. She gave one mightier tug and the seams of the white briefs ripped off in one spectacular destruction of fabric, the force of which made Luke’s eyes water. His legs gave out from supporting his weight through the pain and his crotch was sore enough that he would need a minute to be able to move again. He went down on the blacktop, Sarah behind him with a smile and a laugh.

He laid face down on the asphalt. The pain in his crack was unbearable as the remains of the fabric ripped free from his body and pants. He was sure most, if not all of his underpants were gone. Yanked off with extreme power.

She stood over him looking down and smiling.

“The girls at the office aren’t going to believe this.” She pulled out her camera phone after dropping the remains of Luke’s undies on his butt, to show the true damage. She snapped couple and Luke luckily managed to keep most of his face out of them.

She finished up and looked down. For a moment Luke thought she might take pity on him and help him up, maybe apologize for the worst wedgie in ages. Instead, she reached down and grabbed the remains of his white briefs.

“One last trophy.” Sarah said laughing, twirling the white fabric in the air above her head.

She slowly turned his head to watch her leave. Her dress swayed as she walked. She had nice legs and Luke just wished the breeze was a bit stronger to let him see those pink panties. It might take his mind off the pain.