***Huge thanks to*** u/Few-Masterpiece7291 ***for giving me the idea for this story, plus his input with this ending. I'm planning for three more alternate endings, they will follow in a separate post, soon.***

**Story:**

Kyle had always had a crush on his classmate Chloe. She was so beautiful, a cute blonde with green eyes, her smile always lit up the room. Kyle always fantasized about her when he was alone in his room. He had this crush for years now, he was just too shy to act upon it even though he had very little competition. As gorgeous as Chloe was, her other classmates had a hard time accepting that she was transgender. Even though they knew she was smart, kind and pretty kids are just too cruel and unaccepting like that sometimes.

For Kyle none of this mattered though. He was simply too afraid to be publicly rejected so he just admired Chloe from afar. He tried to talk to her a few times but it was all just meaningless small talk. By the time they graduated he was afraid that being with his dream girl will always be just a fantasy. Then the idea hit him. If they are not in school anymore he won't be publicly rejected either. He can just walk up to Chloe and ask her out and no one will know even if she laughs at him. He was now determined. He was going to do it the day after graduation.

The sun was shining brightly on a Saturday afternoon, the smell of summer filled the air. Kyle must have been standing on the sidewalk for an hour now. He finally made up his mind and entered the arcade where Chloe was working. She was standing in the corner waiting for customers to go up to her and ask for help. It was her job to assist them with any problem they had with the cabinets. Kyle mustered up the courage and walk up to her.

"Hi Chloe."

She was surprised but happy to see a familiar face.

"Hey Kyle," she said with a big smile "can I help you with one of the games?"

"No, actually. There is something I've wanted to tell you for a long time."

"That sounds serious. What is it?"

"You are most beautiful girl I've ever seen Chloe. I've had a crush on you for the longest time but I guess I was didn't know how to ask you out. So I figured I'm just going to be direct with you. Do you wanna go and see a movie with me tonight? As a date?"

Chloe looked puzzled for a second but then her face lit up and she started smiling.

"Of course, I'd love to."

Kyle was the happiest guy on the whole planet at that moment. He wanted to stay and talk to Chloe some more but her manager came out from his office so he had to leave. They met later in the evening and watched a movie together. Once it was over neither of them felt like going home so they spent a couple more hours sitting in a nearby park talking. They shared more with each other than they did with anyone else ever. They were both kind of introverted so it felt nice finally being able to open up to someone.

Their next date was at the beach a couple of days later. Kyle couldn't get over how hot Chloe looked in her black bikini. She was already going through hormone therapy and her body was very feminine. It was especially exciting to see her like that as she usually wore less revealing clothes. The two of them played in the water, had something to eat then found a secluded area underneath a pier where they spent most of the day making out. It was a fun date for both of them and Kyle couldn't wait to see her again.

A few days have passed with them only talking online when Kyle received a message from Chloe one morning. "Come over to my place tonight, I have a surprise for you. xoxo" Kyle couldn't believe it. Can he be so lucky that he can finally spend the night with this amazing girl? He spent hours getting ready then departed at 8 pm for Chloe's. Once there he eagerly knocked on the door and soon heard familiar footsteps.

**Ending 1: Where things go wrong and balls get crushed**

The door opened and Chloe was standing there. She looked stunning in a little black dress, black stockings and a black headband. Despite the serious attire, she was smiling from ear to ear.

"Hey there. Come on in."

The moment Kyle was inside Chloe basically jumped him. He was barely able to remain standing as she was kissing him all over his face.

"Finally. I've been dreaming about this for so long" she said between kisses.

"Chloe, please. Slow down, I won't run away."

Chloe stopped for a moment and looked Kyle in the eyes. Her expression was all serious now.

"Tell me Kyle, would you like to experiment a little tonight?"

Kyle had no idea what she was talking about but he was way too horny to say no to anything.

"Sure. What did you have in mind?"

Chloe lead Kyle upstairs to her room. There she made him strip. Kyle felt a little uneasy about heir first time being so weird but decided to play along. When he only had his underwear on Chloe took out two pairs of handcuffs from her drawer. She ordered Kyle to lay down on her bed and she cuffed his hands to the bedposts. He was surprised by how freaky she was being, very different from the sweet and shy girl he was being used to.

"Wow, Chloe, I never knew you had such a kinky side."

"Shhhh. I know, right? I'm full of surprises. Let's just say that I'm into a few things that aren't exactly vanilla. But don't worry, I'm not going to hurt you. Too much." She sounded way more playful than menacing but Kyle was getting nervous nonetheless.

First, Chloe took out a crop and struck Kyle with it a few times. It actually hurt so he tried to protest but she seemed to enjoy herself way too much to care. After a few hits she herself was naked save for the stockings and judging from her erection she was a lot hornier than Kyle at this point. She also took off his boxers and gently hit his cock with the crop once. After striking him a few more times over his legs and chest she put away the crop, grabbed a bottle of lube and climbed on the bed between Kyle's legs. She then licked her finger and started to play with his asshole.

"I believe you came here today to fuck me. Is that right, Kyle?" she asked in a demanding tone.

"Umm, Chloe, what are you doing?"

She put some lube on her hand and started lubricating his asshole with it.

"Do you think it's fair that you want to fuck my ass, but I don't get to do it to you?"

"Look, Chloe, I'm not into this anymore. Please just let me go."

"Well, you might not be into it, but I am. Now relax. It won't be that bad."

With that Chloe put some lube on her dick and started to rub it in. Then, without wasting any time, she pushed her cock inside Kyle's asshole. She fucked him for what seemed like an eternity, slapping his face and pinching his nipples repeatedly in the meantime. It took her a good thirty minutes to finally cum. She was panting heavily but Kyle was just happy it was over.

"You had your fun, Chloe. Let me go now, please."

"Don't be silly, Kyle. It's not over yet. I will now try some CBT with you."

Kyle knew very well what that stood for and he was having none of it. He demanded that Chloe let him go. She didn't care, however. She just pinched his nipple and slapped his balls really hard. This was now way too much for Kyle. He started struggling against the handcuffs but they wouldn't open. Chloe just laughed, then went to her drawer and returned with a couple of clothespins. Kyle knew what was coming so he started frantically kicking around, without even looking. Suddenly he heard a scream. When he looked up, Chloe was rolling on the floor, grabbing her crotch. He must have kicked her in her balls.

What actually happened was way worse. He did kick her in the balls but this cause her to fall over and hit her balls on the bedpost as well. As she was grabbing her crotch all she could feel was a mess inside her sack. She must have hit the bedpost really hard. Chloe was in a tremendous amount of pain but was angry beyond belief as well. She managed to stand up and turned to Kyle.

"Look what you did! My balls are gone!"

"What? Sorry, I didn't mean to hurt you. I just wanted you to let me go!" Kyle was now panicking.

"Don't worry, I'll let you go in a minute. But not only I made you pay for this."

She stormed out of the room and return in a few minutes with a nutcracker.

"Chloe, what is that?"

"You'll see." she said in a stern voice as she sat between Kyle's legs. She was way too close to his crotch, it didn't matter how much he moved, he was unable to get himself away from her. Chloe grabbed his balls firmly and placed one of them into the nutcracker.

"You crushed my balls, now it's time for payback." With that she closed her tool and Kyle's left nut was turned to mush. He screamed in agony, tears filling his eyes.

"Please, Chloe, stop it! It was an accident. I'm so sorry. Please, don't crush my other nut."

"An accident, huh? And how is that supposed to make me feel better?" She basically shouted in anger. Kyle had never been so scared in his life. His crotch was burning from the pain. He pleadingly looked at Chloe who gave her a sadistic smile.

"It's only fair if I crush the other one as well."

Kyle was unable to move at all at this point. Chloe put his remaining testicle in the nutcracker and slowly crushed it. Kyle was screaming like hell and he was drenched in sweat. He felt his ball crush then he passed out.

Chloe and Kyle never talked to each other again after that night. She has fully transitioned now and is married to a rich, older man. They moved away a couple of years later. To the outside world she is simply a young trophy wife to an older man but in private he uses her for all kinds of deprived sex games. Kyle hasn't really been interested in relationships since his first night with Chloe. He can't have sex ever again and doesn't fantasize about anyone anymore either.