Luke's Field Trip

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A sissy gets discovered and used by his crush on a trip.
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All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo

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Luke was a sissy.

The kids at school called him mean names and threw things at him. They played keepaway with his books (this wasn't helped by his short stature). He had been chased down more than once by the football team, and the cheerleaders made him wear one of their outfits to school once, on homecoming no less.

At home wasn't much better. He had an overbearing mom who tried to control every aspect of his life and his father was a gruff man who drank too much and didn't make room for anyone. His older brother was a star wrestler who had already been through college and lived on his own now. His younger sister (who was still taller than him) was beautiful and was one of the most popular girls at school.

And the main person behind all of this torture was Reid. The captain of the cheer team and the girl Luke had had a crush on since third grade.

And his favorite form of escapism did not help his problems.

Luke loved to wear women's clothes.

He secretly hoped that one day his sister would catch him and then everyone in school would know about his secret life and Reid would be his Mistress.

But it was nearing the end of his junior year, which meant he only had to make it one more year before he could go away to school and start living the life of his fantasies.

He sometimes dreamed that he would be walking back to his dorm late at night, wearing a very revealing short dress, or better yet a schoolgirl outfit, and he would come across a group of Frat Boys on their way home, who might have partied a little too hard. They would take him back to their house and have their way with him, and then he would join as the house sissy.

But until then, he still had to worry about avoiding his next swirly at the merciless hands of the jocks.

As the year was winding down all anyone could talk about was the class trips.

Luke went to a school for "troubled kids" who had failed to pass high school on their first try. Everyone there was college aged but it was more of a high school than a college (to restrict their freedom and keep them out of trouble).

Freshmen were too young and therefore did not get to go on a trip. Sophomores were headed up to the mountains this year for a week of nature trails and outdoor activities.

Seniors were off to the beach for a full week of drugs, booze, and poor decisions.

This year the junior class was going to take a trip to the capital. And because he was a boy, naturally he was going to have to spend the night with other boys, not that any girls would want him.

Luke dreaded this trip and was totally content to not go, but his parents decided that it would be a good experience for him, so he was going.

Finally the day of the trip arrived and all of the juniors climbed onto a charter bus that the school had rented them while the red-faced principal yelled at the students and the teachers already looked tired.

No one would let Luke sit with them so he was forced to sit next to the largest guy in the class, who might have had the lowest IQ in the class.

After hours of riding next to a smelly snoring ball of lard, the class who had undoubtedly had at least 3 hookups already stopped for lunch at a rest stop. While many of the people played games like frisbee or pickup football, or simply talked with their friends, Luke ate his bagged lunch by himself. His lunch consisted of a pb+j, cheese puffs, and a note from his mother like he was 8 years old.

As Luke was enjoying a rare moment alone Reid walked up accompanied by her boyfriend Todd (the school's quarterback, and the utter stranger who his father called the son he never had) and her usual posse of popular kids.

"Hey there sissy, whatcha got for lunch today?" Todd said as he grabbed Luke's lunch away from him.

"Peanut butter and jelly, cheese puffs, and oooohhhhh what's this? Aww a note from mommy. It says "Remember to call every night and tell us all about your trip, and don't let those kids make you upset. No matter what happens always remember that you're my sweet little babykins."

"How sweet, mommy loves her babykins." Todd jested as the crowd laughed.

"Hey give that back!" Luke said as he tried to jump to get his things back.

"Wow Luke, your weaker than I remember. I bet you can't even beat a girl at arm wrestling." A basketball player said.

"Can too!" Luke said back sounding utterly pathetic like a little kid.

"Really, well lets find out, shall we." Said Reid as she waved her arm towards the nearest picnic table.

The group walked over and gathered around as Luke and Reid grabbed hands. Luke was blown away by how beautiful Reid's hands were, and was instantly turned on just from touching them and he had to fight the urge to get an erection.

"How about we up the odds a little bit? If I beat you, you have to do something for us."

"Like what?" Luke almost sneered back.

"Well, why don't we just decide after the match why don't we? Because if you beat me it doesn't much matter now does it?"

"Hmm, ok." Luke said fairly confident in his skill as he had been working out a lot due to his lack of friends and subsequent ample amount of free time.

Todd came up and placed his hand on top of the opponents' two hands and said "three, two, one, wrestle!" at that moment Reid kicked Luke in the balls catching him completely off guard and slamming his hand down on the table.

"Hey, that's no fair she kicked me in the nuts under the table!" Luke whined.

"I don't think the young lady did, unless you want to try and prove it?" Todd said as he moved in menacingly.

"And even IF I did, there were no rules against it." Reid said as she turned away with a skirt flick.

Turning her head back Reid said "See you later, sissy." As she walked away to the bus.

At that moment the principal started screaming for all the kids to go back to the bus.

Luke had only taken a couple bites of his sandwich and now it was time to go. He knew that he couldn't take his food back on the bus as this was strictly forbidden and there were teacher patrols every few minutes, even if he could find his lunch, which was currently MIA.

After more excruciating hours of travel, they finally arrived. It was too late to go to anything, so they were going to stay the night and start exploring in the morning.

Since Luke had no friends to speak of, no one let him sign up for a room with them, therefore the school had simply sorted him into a random room. As he soon found out, his room mates for the night happened to be Todd and 2 of his cronies. Fortunately for Luke, one of the buffoons brought their XBox so Luke was safe to hang out in his own little world while the meatheads killed each other with virtual weapons.

After a few hours there was a knock on the door. One of the aspiring nightclub bouncers answered it. It was one of Reid's friends and she had a message for Todd. The giant called Todd over and went back to sit on the bed. Todd and the bimbo conversed for a few moments and then they both laughed and the girl went on her way. Todd came back and sat back down and continued with his game.

About half an hour later Todd's phone rang and he answered it.

"Yeah. She's on her way?...ok."

Todd then stood up and looked at Luke who was sitting in the corner pretending to read a book, but in reality looking at a women's fashion magazine.

"Hey sissy. Remember when Cindy came by a little while ago? Well, she had a message from my baby. It was instructions for the first part of Reid cashing in for you losing to her like a little bitch."

"What are you planning?" Luke asked in horror.

"Oh not much...just this..." Todd and his buddies then proceeded to hold Luke down and strip him of his clothes. When they removed his boxers they laughed at his little weenkie, and Luke was fairly certain he heard someone take a picture to post on Facebook.

After he had been forcefully stripped he was thrown out into the hallway. To Luke's chagrin, almost the entire class was in on this "bet".

He had to run down the hallway as people jeered, and laughed, and threw things at him. Then someone yelled "Hey everybody, Ms. Clark is coming!" And everyone retreated to their rooms...except for Luke who was locked out of all the rooms, apparently by design.

Luke knew he would be expelled if Ms. Clark caught him naked in the hallway on a school trip. Then suddenly to Luke's great surprise he was pulled into a room right before Ms. Clark turned the corner.

"I don't know why you saved me, or what you want but I owe you one." Luke said thankfully.

"Good, because technically you've already fulfilled your part of the losing punishment." a girl's voice said. Luke could instantly tell who it was.

"I'm glad you came by sissy. We've been planning this all day long." Reid said. "You know, it's amazing what people will do when you threaten to expose them for sucking off almost the whole football team." Now looking at Luke's sister Sally who was sitting in the corner, completely naked with some sort of ball gag in her mouth.

"Hey, I really don't know where you're going with this, but I don't think I like it." Luke said nervously.

"Oh don't worry sweetie, I don't want much, especially since it's something you already like to do."

Luke looked over at his sister who was now blushing and looking ashamed.

So she had seen him running from the bathroom to the bedroom in a pair of her panties the other day.

"Hey I really don't know what you're talking about."

"Well, you'll find out soon enough...come on girls bring him in."

The two other girls wrestled him into the room, which wasn't hard considering they were on the state championship basketball team and Luke had never played sports in his life.

The two girls held Luke down on the bed as Reid chuckled maliciously.

"Your sister told us that you like to wear girl's clothes so I thought I'd indulge you and make you my bitch tonight." Reid chuckled again.

Reid walked over to her bag and pulled out a gorgeous pink bra and panty set.

"Ok sissy you're going to wear this tonight, understand?"

"I have no idea what you're talking about." Like spat back but in reality he had never been more turned on in his life. All of his fantasies were coming true.

"Let him up." Reid commanded. She knew that he wouldn't run away, not from what he had wanted for so long. "Ok sissy, you're gonna put these clothes on now." She tossed the lingerie onto the bed.

"And what if I don't want to?" Luke said with a sneer.

"Then we'll call Ms. Clark and tell her you broke into our room and tried to rape us."

Luke was horrified. He was now at a crossroads, he could either indulge what he had wanted for so long by humiliating himself or he could go to jail (another of his fantasies but that's for another time).

"Well then I guess you leave me no choice." Luke said resigned to his fate.

"Such a good sissy, I guess you understand the situation now. Don't worry though, I'll make it enjoyable, I'm not a complete monster. Now put on those panties and I'll do your makeup." Reid said as she turned and walked off to the bathroom.

Luke slipped the panties on and then attempted to put on the bra but couldn't quite reach the hooks.

"Let me teach you something honey." Abigail (one of the girls who had previously been holding him down) said. "Instead of immediately putting on the straps and then doing the hooks, put it on backwards, do the hooks, and then slide it around on your body. That makes it a lot easier until you get some more experience."

"And from the way Reid was talking earlier I think you'll get a lot." Abby whispered.

"Ohh Luukee, come here sweetie pie." Reid called from the bathroom.

Luke obliged and went in to the bathroom where there was more makeup than Luke had even dared to imagine in his wildest dreams. "Ok honey I'm going to make you up like never before. My mom works in a beauty salon and there's a couple of drag queens that come in every once in a while to get fixed up so I'm familiar with anything and everything you're going to need ok sweetie."

An hour and a half later Luke was dolled up and you couldn't even tell he had ever been a boy. "You look so good sweetie, now lets go have some fun." Reid giggled excitedly.

Luke had of course been reluctant at first but now he was having so much fun living his dreams that he never wanted this night to end.

"Hey it just occurred to me, now that you're a girl, you need a girl name. How about...Lucy?"

Luke was absolutely enchanted. He loved his new name. "Yes! That sounds beautiful!"

"I'm glad! Now lie down on the bed for me ok, and no peeking, I have a surprise for you." Reid said as she walked towards the closet.

Luke laid down, closed his eyes and waited for whatever Reid was going to give him. He could hear metal jingling and then she walked back over and hopped up on the l bed. "Open your eyes honey." Luke opened his eyes and was staring down the biggest cock he'd ever seen. Apparently his surprise was going to be a through fucking. Now Luke of course had had gay fantasies and pegging fantasies, but none of them we're very strong and not something he had ever seriously considered.

"I don't know Reid, I've never done anything like that before." Luke said with more than a little fear in his voice.

"Don't worry Lucy, Todd was reluctant at first too, but now he loves it!" Reid said. "Here why don't I give a demonstration." Reid grabbed Luke's sister Sally who had been released while Luke was getting his makeup done. Reid threw Sally on the bed face down and put the ball gag back in her mouth and fastened it behind her head. "Ok slut, you remember your initiation? Prepare your hole." Reid said as she thrust her member deep into Sally's pussy. Sally screamed like Luke had never heard before. The other three in the room were helpless to watch as Reid raped Sally as Sally cried and screamed for help.

Luke was incredibly turned on. He found himself at the mercy of his primitive natures and pulled out his rock hard clit and began to stroke. In a few minutes all three climaxed simultaneously.

Reid simply pulled out and left the bleeding, crying, mess that used to be Sally lying on the bed as she walked over to her new toy.

"Sissy, did I tell you to stroke your little clit? I don't believe I did, now you'll have to receive punishment!" Reid screamed.

She sat down on the bed and pulled Luke over her lap and mercilessly spanked him for an hour. Luke had never felt pain like this before and had never been turned on like this before. "Are you ready for my cock sissy?" Reid asked.

"Yes, I need it!" Luke said.

"WHAT WAS THAT?!?" Reid screeched slapping Luke on the ass 5 more times in quick succession.

"Yes mistress, I need your cock in my ass pussy." Luke moaned through his tears.

"What a good slut. Lie down on the bed bitch." Reid commanded and Luke followed. "It's gonna be fun popping your cherry, virgins are the best!" And with that Reid shoved her cock into Luke's ass, no stretching, no lubrication, just flesh stretching flesh. Luke had never been in more pain in his life and screamed like a little bitch. Fortunately it was over in a few minutes since the pair had already cum once tonight. As he neared climax Luke knew he heard a camera click but at this point he just didn't care, he needed release or else he was going to die. He and Reid got hit with massive orgasms at the same time. After they had cooled down Reid cuddled Luke on the bed.

"So Lucy baby how'd you like your first time? I bet you enjoyed it, well luckily for you, you get to do this again and again every weekend! And bring your sister too, she's precious." Reid laughed wickedly.

The end

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6 Comments
AnonymousAnonymousover 3 years ago
Hmmm!

Wished this story was longer.

AnonymousAnonymousover 5 years ago
New chapter

Please write a new chapter.

AnonymousAnonymousover 6 years ago
Hmmm. Good but...

What is his sister's name? Referred to as Daisy then Sally.

Is Reid TG?

AnonymousAnonymousover 6 years ago
Yeah but Luke got smart

And recorded them on his I-phone. when he reported their abuse and torture, they all went to jail. The end to this stupidity.

PaddlesPaddlesover 6 years ago

Great story, be sure to write more

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