High School Sweethearts

The next morning Andi and Jack got up and did their makeup. Andi then produced the clothes that she wanted Jack to wear, and he put on his chest piece, and got dressed. The skirt on Sunday was even shorter than the previous one. Jack was mortified that a good breeze would be enough to let everyone see his ass.

The two went to breakfast, and then spent most of the afternoon in a coffee shop studying. As they were packing up to go back to the dorm room to get dinner Andi's calendar event went off signaling that Jack could cum again.

Andi leaned in close to Jack's ear and said "you can cum again little sissy, do you want to fuck me?"

Jack whispered back "yes Mistress, I want to fuck you so badly."

"Then let's see if you can earn it." Andi replied, while reaching up and giving Jack's cock a light stroke.

Andi and Jack returned to her dorm room, and Jack proceeded to eat Andi to three orgasms in under a half hour. Jack then proceeded to beg to fuck her.

"Please Ma'am, I need to fill you up, I need to feel your wet pussy around my cock, please I desperately need it." Jack pathetically begged.

"I know you do little girl, but not yet, you haven't earned it yet." Andi said with a grin.

"How do I earn it ma'am?" Jack begged.

"Well, as you know tonight is the Panther Party..." Andi began.

The Panther Party was a party hosted every year by the black fraternity on campus on the Sunday before Martin Luther King day. It started out as a celebration of Dr. King, and his work, but by 2016 it was merely a giant beer bash with loads of debauchery, it was usually the first big party after classes resumed for the spring semester, and as such it was usually one of the four craziest parties of the year.

"So, tonight you and I are going to have a little competition, whichever one of us can make the most guys cum in two hours at the Panther Party gets to fuck the other one!" Andi's eyes lit up as she explained her idea to Jack. "Don't worry baby we'll keep it to just sucking cock and handjobs so I don't have an unfair advantage."

Jack had no idea how to respond. He wasn't entirely thrilled with the idea of Andi sucking off other guys, nor was he thrilled to have to compete against her, to make it all worse he was mortified at the thought of being recognized during the experience. Ultimately, he agreed, mostly because he was certain that with or without the competition in play he would be sucking cocks tonight.

Andi and Jack hung around the dorm room until 9:00, when the party had already been raging for an hour. Andi told Jack that she was trusting him to be honest with how much dick he swallowed tonight, and that she kinda did hope he won, because she wanted to be fucked.

Jack watched in amazement when he first stepped into the frat house at how drunk some people already were. Within a few minutes he felt a hand on his ass, and remembered just how passable he was. He turned around, and when the hand tried to remove itself he stopped it. Jack looked into the eyes of Harrison Orly, one of the college's premier football players. Jack had never actually met Harrison before, but with Harrison's hand on his ass immediately moved into kiss the muscular jock.

As he broke apart the kiss Jack said "You're a pretty good football player aren't you?"

Harrison nodded with a smirk. Jack slid his hand down the front of Harrison's jeans and said "I've always wanted to suck a star's cock."

"Go ahead then." Harrison replied, while unzipping his jeans.

Jack was astonished that Harrison was going to let it happen, right here, in the middle of the party, Jack personally was always too ashamed to allow anything close to that to happen. But Jack complied, as Harrison pulled out his cock Jack dropped to his knees and was amazed at the monster that was in front of him. Harrison was at least eight inches long, and twice Jack's girth. Jack did his best to suck the cock, but was having significant difficulty. After several minutes of only being able to lick all over his cock, and suck on the cock head Jack was slowly able to take about half of Harrison's dick in his mouth.

Jack kept working his tongue around everything he could get his mouth on, while at the same time using his hands to jerk Harrison off. Harrison started grunting, and after another ten minutes finally blew a massive load into Jack's mouth. Jack coughed as cum blasted the back of his throat, and gushed out around his lips. Once he had a second to breath Jack began licking all of the cum off of Harrison's dick, and wiped the excess off of his chin and lips.

Harrison zipped his pants up, and said "why don't you follow me for a second."

Jack did as he was told, and was led into a basement room. Inside the room were a half a dozen other football players playing cards. Harrison announced to the room "I think I've got the biggest cock slut of the party boys."

Jack had no idea what it meant until one of the men at the table stood up and unzipped his jeans producing a long thick cock "that's a big proclamation Harrison, lets she if she can prove it."

Without warning Harrison shoved Jack to his knees and forced his head in front of the other player's cock. Jack opened his mouth and began to suck. This was easier than Harrison's it was still long, but nowhere near as thick. For ten minutes Jack worked up and down the shaft of the cock, at times swallowing the entire thing. Finally the man put his hands on either side of Jack's face and just began to fuck Jack's throat. Jack gagged, but did not throw up, when the man finally blew his load Jack was able to swallow all of it, before being shoved roughly backwards off to the man's cock, and onto his ass.

When the first man finished the other men formed a circle around Jack and pulled him back to his knees. Jack proceeded to grab two cocks at a time while taking a third into his mouth. The men periodically moved Jack's hands or head around to take a different cock. After nearly an hour Jack's mascara was running and he was completely winded from being forced around. Jack was also insanely turned on and wanted nothing more than to have his cock stroked right now, the men had been degrading him all night calling him a whore and a slut, and he loved it.

One by one the men started to cum, and Jack took most of it in his mouth, but they also hit his face, and his hair as well. When they finished they all left the room, and Jack texted Andi a picture of his face and said "I have seven."

"Meet me outside." Andi's reply text said.

When they met Andi shook her head looking at her boyfriend "you are going to be a huge slut someday." Was all she said.

They started walking back to Andi's dorm, and Andi told Jack "I only got five, so you get to fuck me, but you have to stay dressed up like a little sissy to do it."

"Yes Mistress, I like that idea a lot Mistress." Jack said.

When they got back to Andi's dorm room Andi quickly stripped, and then took off Jack's panties. She loved how he looked with a fully erect cock tent-poling his skirt. Andi started to rub his cock and balls before kissing him deeply, and laying back on her bed. Jack could see how wet her cunt was, and he wasn't sure what had caused all of it, but he was certain that her demeaning and degrading him was a huge part of it.

Jack slid his cock into Andi, and it took everything he had not to cum right then. Jack started pumping his cock in and out of Andi as quick and as hard as he could, Andi moaned deeply with each full stroke.

"I do love your cock baby, it's why even if I make you a total sissy I still will let you keep that nice cock and balls." Andi moaned.

Jack had no idea what that meant, but kept plowing into Andi, knowing that it was an opportunity that would not come around often.

"Have you loved living out your fetishes baby?" Andi grunted out between moans.

"Yes Mistress I have, so much thank you Mistress." Jack replied.

Andi started to open her mouth again and Jack interrupted her "Mistress, oh fuck...oh...I can't stop myself, can I please cum." He begged.

"Yes" Andi replied, and as she did so Jack's cum flooded her, and brought her to a long and different kind of orgasm.

"Lay on the floor, you still have to swallow it out of me." Andi panted as Jack slid out of her.

Jack complied, having learned to love the taste of his own cum, and that of others. Andi squatted over his face, and Jack quickly moved his tongue into Andi's wet and gaping slit.

"Tomorrow I have one more surprise for you." Andi said as she rolled off of Jack and collapsed onto the ground beside him.