A College Sissy Ch. 03

"Now because this tranny is so ugly she'd never get anyone hard, we'll kick this off with a bang," the guy said. "Ladies?"

The crowd started to cheer. Abby turned to Meredith and they embraced. They began to make out hard. Abby reached down to Meredith's ass and squeezed. Meredith, this incredible, composed and perfect blonde woman, kissed Abby's neck and reached into the front of her panties to finger her. The crowd went wild. I looked around at the pledges, none had sprung erections, but a few were looking up at the ceiling, pained.

"Alright," the frat president said. "You passed the first test. This should be easy, pledges, unless you really do like trannies. Abby, any final words to your... pledge?"

He paused on the word pledge like it was absurd I could ever be a sorority girl, or a girl at all.

"Ali," Abby said, whispering, as the crowd started to grow rowdy, throwing beer cups into the middle of the circle. "If you can get one these guys hard, you're in. We all had to do it in Kappa, OK?"

"OK," I said.

"You look great, hon," Abby said. I appreciated her sweetness. For every trick she pulled, she came back with something sweet. It was a crazy game she played with me.

I did, however, feel renewed determination to make at least one of these guys hard after her pep talk. I stood up and started to dance as sexily as I could. It was embarrassing. All the guys on the outside started to laugh, and Meredith doubled over in laughter, leaning into Abby. Even she was laughing, too.

I slowly pulled up my tight dress over my ass to reveal my pink satin panties. More catcalls came from the crowd. I didn't see a hard cock in sight, but I saw several guys looking away from me. Actually more guys were looking away from me than when Abby and Meredith made out.

I looked around the circle, tousling my hair, and dancing to the music that a guy had started to play on the speakers — Dude Looks Like a Lady. Of course. But I felt like a stripper, and I knew overcoming humiliation was part of the transformation process, and part of what the sorority was looking for.

I finally caught eyes with a guy who looked really scared. He had long-ish, wavy brown hair. His muscles were slightly defined. He was tall and tan, with dark brown eyes. He had his hands behind his back.

"Uh oh," came a chorus of guys as I started to walk over to him.

"What's your name?" I whispered in his ear, turning my back to him and sliding down his front.

"Go away," he said. "Please."

I felt bad, but I wanted to show how quickly I could win this challenge.

"Shh," I said, putting my finger on his lips and smiling. The crowd loved it and laughed. "Just fuck me like you want to and this'll be over."

He sighed and looked me up and down as I danced up on him. I rubbed my satin pantied ass over his cock, back and forth. I turned to face him and placed his hand under my dress and onto the bulge in my panties. He shuddered and let out the littlest smile. I immediately leaned in and kissed him on the lips. He opened his mouth slightly, forgetting where he was, and for a second, he slipped his tongue into my mouth.

He pushed me away and said, "Fuck," loudly and angrily. When I looked down, his cock was rock hard.

"Wow, that was quick!" the president said. "You must love fucking sissies you goddamn queer. Alright, Mark, you know what you gotta do if you want to be in. Everyone else, you're brothers. And brothers stick together. So if you also want to be in the fraternity, you're going to have to cum, too. So start jacking off, and when these two sissies are done, you're going to cum on them." The president barely got out the orders before laughing uncontrollably and falling into his laughing buddies.

Mark looked at me softly. I could feel for him. We were in this together, and he and I were in remarkably similar positions. He clearly had a thing for me, and probably had a thing for guys, transgender people or something in between. Meanwhile, I was just trying to validate my own femininity through sexual actions; the only way I knew how. We were both trying to gain access to clubs that are based on gender — a fraternity and sorority — yet here we were, clearly blurring gender and romantic lines.

I think I fell a little bit in love with him. Or, the idea of him at least.

"C'mon, Mark," the president said. "Fuck that tranny."

"Do it," I said, smiling a bit. "Let's just get it over with."

I dropped to my knees and starting blowing Mark as best as I could. Even with all the guys jacking off and looking at us, I blew him not to prove anything to anyone but him. I wanted him to feel so good that he would think this was natural and that he'd be OK with maybe loving me back. I grabbed his ass and thrust his cock deeper into my mouth.

"Gag that fag!" someone yelled from the crowd. I looked up at Mark's eyes with his massive cock in my mouth and nodded. He grabbed my head and thrust me down until I gagged several times and slobbered all over my chin. I had glittery tears running down my cheeks.

Then the crowd started to chant "Kiss!" I pulled Mark out of my mouth and stood up, wiping away my strewn makeup. We were the same height with me in my heels. He put his arms around me and pulled me in. We met lips and enjoyed a deep kiss. Our tongues wrestled for a minute or more, occasionally bobbing back into our own mouth so we could touch lips tenderly. Mark put his hands on my butt and lifted up my dress to feel my panties. He poked his finger into my asshole from the outside of my panties.

"Now fuck!" came more calls.

"It's all yours, Mark," I whispered in his ear.

I got on all fours, in this banquet room filled with fraternity brothers cackling and calling me 'tranny' and 'faggot' with this guy I'd never met but whom I think I had a connection with and who was about to plow my ass in front of the crowd. I got on my knees and he got on his, and spit down on his cock. He forced it into my hole and the crowd cheered as he leaned back and sighed in subdued delight. It hurt my tight, dry hole, but I loved the attention and I wanted to be as close to a girl for Mark as I could. He pumped hard, trying to get off as quickly as possible so we could be done with the show, and I pumped back, bouncing my fat ass for him, occasionally spinning my hair and looking back at him in my sexiest feminine gaze. I was going to be his girl tonight.

That was the plan until someone yelled, "Cum in each other's mouths!" which elicited a huge response from the crowd. Mark pulled out and I got on my knees to face him.

"I'm sorry," I said, pushing his back onto the ground. I straddled him and took my dress off finally, and the crowd went wild, half mocking but also half eager to see the grand finale. I pulled my panties aside and pulled the hair over my head and lowered myself onto Mark. He took my cock into his mouth and the warmth of it nearly had me explode immediately. I took his cock into mine and we 69'ed in front of the crowd hollering, "Cum!"

I bobbed my head aggressively up and down on his cock to put on a show. Mark sucked my dick like it was his first time, and it probably was. Though, he was eager. I soon pulled off his cock and sat back on his face to ask him, "Ready?" The crowd loved that I was sitting on his face. He answered back, "Yes," muffled.

I got back down on his cock and felt my cum go. Just as I did, I took the biggest load in my mouth that I'd ever taken. "Don't swallow," someone said. And so I sucked Mark dry and then got up, knowing what to do. I turned around and laid on top of him, in my pink bra and panties and high heels, with my slutty makeup and hair, and swapped cum with him. It was messy, but Mark seemed relieved and aggressively tongued me back.

"Ok, ok, faggots," the president said. "Boys, get to it."

The group of young guys circled in, tugging on their throbbing red cocks. I was in such bliss with Mark, having felt such a connection, that I had forgotten about the rest of the job. One by one the pledges stepped forward to shoot their loads over Mark and I as we passionately made out throughout the entire process. Mark had to pretend to get out of the way of the cumshots, to save face with his brothers, so when jizz did land on his face, I'd pull my tongue out of his mouth to lap it up. Before I swallowed, I'd kiss him deeply. That was just for us. He grew resigned with the fact that he liked it; his brothers be damned. Occasionally I'd peel off to catch a cumshot on my face if I saw a guy was ready. Some aggressive guys would push my head away and say, "Stop it, faggot," which hurt, but I guess I was getting the last laugh, huh? The final guys finished up, and by the end of it, Mark and I had swallowed about 23 loads.

Exhausted, I pulled off Mark and got my dress. I slid it back on as the crowd dissipated, humiliated by what they'd seen, while some guys clearly tried to compensate for their confused feelings of arousal during the process. I walked over to Abby and Meredith at the door.

"So, did I get in?" I asked. Meredith laughed.

"You're a fucking tranny whore. We're a sorority of women, and you'll never be one. So no, you're not in, faggot," Meredith said. I looked at Abby.

"Sorry, Ali, it was my turn to get a sacrifice for the boys," she said. "But don't act like you didn't love it."

"Yeah," Meredith said. "You're not a sorority sister, or a woman, but you clearly loved every second of that. And I think we're going to use you again in the future. Is that OK, Abby?"

"That's why we have her," Abby said. "Now go back to the dorm. I'll meet you there later tonight."

I felt used. Mostly because I was. But I was shocked that my brain had developed an attraction to a man. To Mark. That relationship, me as a girlfriend, felt new and exciting. Whatever Abby did to me and however she abused me was immaterial, because I had gotten to this new point. I had something new to latch onto—being a girlfriend, or fantasizing about being one. I had no idea if Mark felt the same.

I got back to the dorm and laid down on the bed in my dress, bra and panties. The same outfit I wore in my dream when I was younger. My past and present, my dreams and my reality, were colliding.

I saw I had two texts.

The first was from Mark: "Hi Ali. It's Mark from the thing. I got your number from Abby. I'm sorry for what happened in there. I rejected the pledge bid from the fraternity. Do you want to meet sometime tomorrow?"

The second was from my girlfriend back home, Emily. My distant girlfriend who still loved me and knew nothing of my new life as Ali: "Ready for me to visit you at college next weekend?"

My past and present colliding.

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Chapter 4: Cuckolded by my roommate when Emily visits; Chapter 5: Sexual favors to a teacher for a good grade;

Chapter 6: Parents' weekend (the finale).