[jipperxl]

Part 15: Jenny’s Bitch


The football team’s third game of the season went off without a hitch, winning 17-13 against another school in the state. With another victory in hand, everyone was ready to party that evening. As usual, Sigma Lambda Epsilon’s house was going to be the biggest bash on the row.

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UNICORN TOSS

Pledges got to the house early to set up. Josh, Chris, and Tyler came a bit later since they were on the football team. Everyone was starting to get the hang of what pledging was all about with SLE. Basically, lots of hazing and lots of menial work. For each party, they were responsible for setting up, keeping party goers content, and cleaning up afterwards. While Josh, Chris, and Tyler were getting updated with what was left to do, one of their pledge brothers recounted something that happened to them at today’s tailgate.

(For every football game at home, there’s a huge tailgate at the stadium’s parking lot where fraternities, sororities, and students get to have fun before the game begins. SLE always has a few tents and trucks stationed there. With Josh, Chris, and Tyler playing football, the remaining five pledges always have to attend the tailgate.) Today, it turned out that another fraternity, Delta Iota Kappa (DIK) at the tailgate wanted to challenge SLE’s pledges with their pledges. Not wanting to ever back down from a challenge, the SLE Brothers accepted it, much to the dismay of the pledges. It was going to be five pledges against five from DIK in a type of relay race. They had to run from one end of the parking lot to the other, but with their hands tied behind their back and their ankles tied as well with a foot of slack. Unfortunately, the SLE pledges lost and had to face the consequences. They were handed over to DIK for punishment. The DIK pledges took the five losers and tied them spread eagle to the parking lot’s chain-linked fence. Their shirts were removed and their sweatpants were pulled down revealing their tighty whities. Each of them had a sock removed from their foot and gagged with it. Letters were then painted on their chests, spelling out L-O-S-E-R-S, with the last person getting two letters. The pledges thought the worse was over. Everyone at the tailgate had a pretty clear view of them and were having fun taking pictures and video and sending them to their friends. However, it didn’t end there. One of the DIK pledges carried over a box. Once he opened it, all of the SLE pledges screamed into their gags and tried to get out of their ropes. In the box, were a bunch of dildos. Of course, the pledges thought they were going to be fucked with them in front of the whole crowd. Well, the other frat had a different idea. The dildos were taped onto the pledges foreheads, making them look like unicorns. DIK then announced a jockstrap throwing game for the crowd and offered prizes for playing. So, for the next two hours, the pledges had jockstraps thrown on top of their heads while they stood gagged, stripped, and tied to a fence.

As Josh’s pledge brother finished the story, everyone was speechless. Josh was thinking about what it would have been like if he was there, and as he was doing so, he quickly caught himself getting hard in his underwear. The brief silence was interrupted when Matt told them to finish setting up for the party.


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PARTY PLEDGES

The party got underway, and it was a packed house. The pledges were allowed to have partake in the fun, but they were given strict orders by Trent, their pledge master. Trent told them they could only wear their tighty whities, socks, and shoes. Then, they were given a small paper cup for beer. Unfortunately, they were not allowed to get beer for themselves, but rather they had to earn it. Anyone at the party could give them beer, but almost 100% of the time, they’d be asked to do something for it. The pledges hated this idea, but the Brothers and all of the guests loved it.

Josh and his pledge brothers had no problem finding people willing to give them beer. The problem they did have was if they wanted to do the things they asked them to do. Josh ran into several people that had crazy demands like “shave your left eyebrow”, “drink a shot of piss”, and “get kicked in the balls.” Of course, he went with more reasonable ones like “get a wedgie from Butch”, “smell Dillon’s feet”, and “be a foot rest for 10 minutes.” For Josh, this all seemed pretty fun for him and he managed to get quite a lot to drink.

At one point in the evening, Matt came over to speak to Josh.

“Hey Jock Boy. I see you’re getting quite the buzz. People are saying you’re a bit more adventurous than your pledge bros.”

“Uh yea, I just...I just wanted to party tonight. You know. Get more beer and stuff.”

“Cool. Well, hey. Have you thought about who you want to have for a big bro?”

Josh shook his head.

“Dude, you have to pick me. We’d make an awesome team! I’ll be the best Big Bro you could ever have,” smiled Matt.

Josh really didn’t have anyone in mind yet and he was clearly too buzzed to think clearly about it.

Josh replied, “Yea, I have to think about it. Does that mean you’d go easy on me?”

“Fuck no, Jock Boy. I just mean we’ll have a ton of fun.”

Josh had no idea what that meant. More fun for Matt or for him?

“Um ok. I’ll think about it.”

Matt’s face became more serious and he put on a smirk. He leaned toward Josh’s ear and whispered, “You know you want to, you little bitch.”

Josh didn’t say a thing as he watched Matt walk back to join the party. His cock was starting to bulge in his tighty whities.

A voice suddenly peeped out of nowhere, “Joshie!”

It was Jenny. She was a regular at the SLE parties and Josh was pretty happy to see her. They haven’t had a good fuck in a while, he thought. She ran up to him and planted a big wet kiss on his lips. In fact, she backed him up to a wall and started to grind him.

“Ooooh, I’ve missed you quite a bit. It’s Jock Boy now right?” she smiled.

“Uhhh, yea. Umm, I missed you too. You can just call me Josh,” he said, clearly getting turned on from Jenny rubbing against him.

“I like Jock Boy better. By the way, let’s have some fun on Monday. You should come over to my place.”

“Sure. That’d be cool.”

“Great!” Jenny then took Josh’s arms and pinned them above his head with one hand and then proceeded to massage his now hard cock through his tighty whities. She then was locking lips with him again.

“Wha...what are you doing...ooooo...man,” mumbled Josh. He was really turned on with Jenny’s forceful behavior.

Then all of a sudden she stopped.

“Wha...what? That’s it?” asked Josh.

“We can finish this on Monday,” she smiled. “Now, does Jock Boy want some beer?”

Josh nodded.

“Ok. Put your hands up.”

Josh raised his arms not even thinking about asking what he had to do for the beer. Then, Jenny quickly pulled his cock and balls through the fly of his underwear, exposing his boner, and then gave him a sharp wedgie.

“There,” she smiled. “Stay like that for 10 minutes. Here’s your beer.”

Jenny left to catch up with her friends while Josh tried to stay hidden in a corner with his cock and balls hanging out of his underwear. SLE parties are never boring, he thought.

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FUN WITH JENNY

Monday was the due date for the pledges to make their Big Brother requests. Josh tried to figure out whether having Matt as a big bro would be a good thing or a bad thing. He decided to request Matt as one of his three choices since he felt that no matter what, Matt was going to torment him in some way. Having him as a big bro could make things slightly better. Plus, he actually felt a bit excited at what kind of “fun” Matt was talking about. The other two people he picked were Butch and Danny since they were on the football team.

That evening, Josh got to Jenny’s place which was just outside of campus. With her family’s wealth, she had her own condo and lived there by herself. This was Josh’s first time there. He stood outside her door and rang the doorbell.

The door opened. Jenny stood there in sheer black lingerie and black heels.

Josh stood there with his mouth open. “Wow. You look h...”

“Shut up bitch and get your ass in here!”

Josh shut his mouth and quickly stepped into Jenny’s place. It was dimly lit with candles and quite warm.

“Take off your clothes,” she commanded.

Josh obeyed and was naked within seconds. His cock was almost fully hard at this point.

“Put your hands behind your head.”

Josh did as she asked and Jenny gave a quick inspection. She dragged her fingers across his chest as she walked around him. Her hands worked their way down to his ass cheeks, which she squeezed and gave a quick slap. Coming back around in front of him, she took Josh’s cock and balls in her hands.

“You seem to get hard too easily. Maybe, I should have these locked up? How do you like the sound of that?” she said as she stroked his cock.

Josh shook his head, “No, I...I wouldn’t like that.”

“Hmm, maybe I should just do it anyways,” she said, as if speaking to herself. “Come, let’s go to the bedroom.” Jenny led Josh by his cock and balls. Josh quickly followed and ended up on Jenny’s bed. Jenny took off her shoes and climbed on top of him.

“Are we going to have some fun now?” Josh asked, eagerly wanting to start fucking.

“Not just yet. I need to get you situated.” With that, Jenny took Josh’s arms and started tying them to the bed’s headboard.

“Um, wait. Why...why are you tying me up?”

“Well one, because it’ll be more fun, and two, you’re my bitch,” she smiled.

Josh decided to go along with it. She finished up with tying Josh’s ankles to the edge of the bed. Now, Josh was tied spread eagle and fully exposed. He felt pretty excited about what was happening. He tested his bonds and realized that Jenny did a really good job with them. Jenny came back to the bed with something in her hand. She came up to his face.

“Open your mouth.”

Josh did, and Jenny shoved a shiny red ball gag in and secured the buckle.

“There! We’re ready to start the fun now,” she said as she patted Josh’s cheek. Jenny stepped out of the room and came back with something else, hidden behind her back.

“So, I got something fun from one of your boys at the tailgate on Saturday. I wanted to see how you would like it.” She brought the thing out from behind her back and revealed a big, black, shiny dildo.

“MMMMMmmpppffff!! nnnooooooooopppphhffff!” screamed Josh into his gag. He started struggling against his bonds. He didn’t want to be fucked by a dildo, he thought. His ass was completely vulnerable and he felt helpless. Jenny stood there and smiled, teasing Josh with the dildo and slapping it against the palm of her hand. She walked around the bed, dragging the dildo across Josh’s body. Josh was breathing pretty hard as he was now feeling scared. In fact, his cock was no longer as hard as before.

“Pppffffffuuufff ooonnfff ooo oonpff” he said.

“I don’t know what you’re saying, but don’t worry, I’m sure this won’t be as bad as you think,” Jenny then put a black blindfold on Josh, which made him even more scared.

“Moooooooooooooooof!”

Jenny brought the dildo close to Josh’s ass, making it touch his ass cheeks. Josh struggled again on the bed, trying to see if he could reposition his ass. He felt it get closer and closer to his hole. For a brief second or two, it was gone, but it came back and touched his asshole.

“Here we go big boy!”

“Mmmppfpff mmoooooooof!”

Josh felt it penetrate his hole.

“MMooooooopff Mmooooppf!” he continued. He calmed down after a few seconds, slightly confused. “That’s odd,” he thought. “I thought it was going to hurt.” The thing slowly continued to get pushed up his ass, and all Josh felt was a slight uncomfortable feeling as if he had to take a shit. Josh wondered if this was always how it felt to have a cock up your ass. Then, his blindfold was removed.

“See, it wasn’t so bad,” smiled Jenny. “Here, we need to get you horny again.” Jenny pick up a small remote and pressed a button. All of a sudden, the dildo in Josh’s ass started vibrating.

“OOoOooooooommmfff!” moaned Josh. The feeling in his ass was overwhelming and his cock was getting hard again. Jenny was pretty happy with what was going on. Now with his cock hard, she put a condom on him, positioned herself on top, and started to force fuck him. Josh was getting really into it and tried to move his hips along with Jenny’s movements, but she was doing most of the work. He was in quite a zone right now. The feeling of helplessness was starting to feed his horny state. He couldn’t move or say anything, and he just had a dildo shoved up his ass. Jenny is using him like a big toy, he thought, and it was utterly humiliating.

“Say, ‘I’m your bitch!’” yelled Jenny as she was riding him.

“MMIimm Hhhurrrr urff (I’m your bitch)!”

“Again!”

“MMmiimm Hhurr urff!”

“More!”

“Mmmimmhurrffurff Mmmimmhurrffurff Mmmimmhurrffurff!” Jenny removed the ball gag “ImyourbitchImyourbitchImyourbitch!” screamed Josh.

“Good. Now, do you want to cum?”

“Yes! Oh god. Yes. I want to cum.”

Jenny stopped the fucking, “Hmm, I dunno. I don’t think you deserve it.”

“Please! Please I need to cum. Keep going! Keep moving!” yelled Josh as the vibrating dildo was still driving him crazy.

“You don’t tell me what to do bitch!”

“Soo...sorry. Please, let me cum. I need to cum. This thing is driving me crazy.”

“Good. That’s a good little bitch.” Jenny, satisfied with Josh’s pleas, continued riding his his cock.

Soon, both Jenny and Josh climaxed. Josh felt that was the best orgasm he’s ever had. Jenny fell on top of him and looked at him.

“Now that was fun,” she said.

She got up and started to remove the dildo from Josh’s ass, only it wasn’t a dildo. She held the thing up.

“You didn’t think I was going to put that huge dildo up your ass, did you?” she smiled. “I shoved this prostate massager up there, instead. Maybe after a few more times, I can fuck you with an actual dildo.” Josh was both relieved and embarrassed at the same time. He never thought that having something up his ass would lead to amazing sex.

Jenny undid his bonds. “Get going now, bitch. And we should do this more often,” she said with a smile.

Josh left feeling satisfied. He got back to his dorm room, where Chris was already sleeping. He headed toward the showers and proceeded to clean himself up. “Man, what a crazy night,” he thought. He replayed the events in his head, from being ordered around by Jenny to having sex with that thing up his ass. He imagined himself tied up again, helpless, and getting his ass filled again. He closed his eyes and started fingering his ass, something he never did before. Before he knew it, his cock was rock hard again.



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