The Princess and the Back Alley

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The prince takes crossdressing too far.
5.8k words
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There once were two kingdoms at war. They were the Northern Kingdom and the Southern Kingdom. The Northern Kingdom was ruled by Alpin, and the Southern Kingdom by Gale. Alpin was winning the war, but growing very old, and even outlived his brothers. Soon his only son would become the ruler. The Southern Kingdom knew of this and had the son assassinated while on an expedition. This left two grandsons, Rain and Stone, to take the thrown. Both grandchildren, 23 and 21 years of age, were being prepared to take over a long-standing war in secret.

Nobody outside outside the royal guards knew the whereabouts of the coming generation. Gale had a vested interest in finding them, but so did many others who wished to become rulers of the powerful kingdom.

Deep in the forests of the North, Rain and Stone were being watched over by fairies.

"I know you are both adults," the red fairy said. "But too many people are after you."

"This is torture though!" Rain yelled. "Every day is the same boring nonsense."

"It is important for the future of the kingdom," the blue fairy said. "Think of the future and how much more you will have."

The young men were reluctant, but stayed in their limited domain. That was until a visitor had shown up. A beautiful girl in her early 20's with long, pink hair appeared one night. She knocked at the window of Rain.

"What?" Rain asked looking out of the casement.

"Down here," the girl whispered. "I heard you were bored."

"Yeah," he whispered back.

"Come outside and we can do something exciting."

Rain did not tell his brother, and sneaked out the window. She grabbed his hand, and led him away.

"If anyone catches me outside," Rain said. "It would be a serious problem."

"Don't worry," the girl said. "I have a plan."

She took him across the forest to her secret dwelling in a tree.

"If you want your freedom, wear this," she said, handing him a short shirt and skirt.

"You don't have any other disguises?" Rain asked.

"Nope, but these are magical," she answered.

When Rain donned the clothes his hair grew out and his body hair vanished. He barely recognized himself in the mirror.

"Whatever works, I guess," Rain said in a feminine voice. "What is your name anyway?"

"I am Lily," she replied. "You?"

"I'm Olive," Rain answered.

The two walked to the city. They took a stroll around town with no one recognizing Rain. It was liberating for him to get out of the forest. They went to a tavern, and men started to flirt with him. He got free drinks from them, but refused to go home with any of them. They spent so much time out that Rain almost did not make it home in time.

Rain removed the clothes and reverted back to normal. Lily went back to her tree. It was a long day for Rain, and he had to take a nap. No one questioned anything, and Rain was out in the magic clothes with Lily the next night.

This night more men were buying him free drinks. He got much more intoxicated than before. Lily had to escort him back, but was unable to lift him through the window after he fell asleep. She took him back to sleep at her home, put him in a bed, and kissed him on the lips. The next morning a search party was out looking for Rain.

Lily looked outside to see guards calling out for Rain. She thought nothing of it though. When Rain woke up, he was too exhausted to care he was not home.

"What are those people yelling for out there?" Rain asked.

"They are calling out for Rain," Lily answered. "I guess the prince is missing."

"Oh no!" Rain blurted out. "I have to go."

"Why?"

"I have somewhere to be. That's all."

Lily grabbed him and hugged him tightly. He hugged her back, then darted home. Rain tried sneaking in and pretending like nothing happened, but his family was furious this time. They screamed at him for his disobedience and forbid him from even going outside without an escort.

A guard would watch over his room all night for the next month. In that time a new girl, Crystal, had been introduced to Rain as a potential partner. They had closely monitored dates, so Rain could not go far with her until he had gained their trust again. She was pretty and friendly, and had swooned him.

When the month had ended, the guard had left. Lily was back outside the window. Rain was hesitant to leave.

"I was in very big trouble last time." Rain explained. "I can't be doing that kind of thing anymore."

"Come on," Lily begged. "You would rather be cooped up than exploring the town freely?"

"No..."

"Good, let's go."

Rain kept looking around suspiciously, but put on the magic clothes and hopped out his window. As they made their way to the town, they caught up on the last month. Lily desperately missed Rain, but he told her he was seeing another girl. Lily's face sank, but she tried to hide it and planned to win him over. The entire night she kept touching him and finding a way to cling on to him.

The prince did little drinking, and stayed distant from the men. The night seemed to be a failure for Lily. Rain returned on time, said goodnight, and went to bed.

The next morning he waited to see Crystal, and, when she arrived, he was overly affectionate. She got somewhat bored of this and became distant. Nothing was going to take her from royalty, but she wanted space. Rain did not take it well, and it was reflected in the coming night.

Rain complained to Lily about the troubles he was facing.

"It is always the same with women!" he protested. "They do not stop with their stupid games."

"Why not get someone else?" Lily asked.

"Because I don't want to leave her."

"It's okay. I understand."

That night the prince had fun and flirted with the men at the bar. He enjoyed being the center of attention. The prince even got up to dance with one. The man grabbed his ass, but Rain let him. It was nice not to have to be the one doing all the work. Ass grabbing led to Rain getting pulled outside to the back.

"What's happening?" Rain asked.

"How about we go a little further?" the stranger asked him.

"I don't know," Rain hesitated, but kept looking down curiously."

"Just a taste?"

"Maybe just to try it..."

The two were behind the tavern up against the wall. Rain undid the buckle and pulled the man's pants down. The stranger's cock sprung up in front of Rain's lips. This made the prince even more nervous, but he moved closer anyway. The man stood there waiting expectantly. Before anything else could happen, Lily came outside and interrupted them.

"Whoa!" the man shouted, putting his dick away.

Rain quickly stood up embarrassed. The stranger left, and Lily took the prince on the journey back home.

"Were you really going to...?" Lily asked.

"The curiosity overwhelmed me for a bit," Rain explained. "It is good you came when you did."

"I guess so?"

It was an awkward walk back, but the prince was home and continued as if nothing happened.

The fairies found the magic clothes in Rain's room the next day. They called a meeting.

"Do you know what these are?" the blue fairy asked.

"Girl's clothes?" Rain answered innocently.

"These aren't just girl clothes. These are magical and have dire consequences. Why do you have these?"

"I found them in the forest on a walk."

"You have no use for them. We will be confiscating them."

The fairies took the clothes away. It was a little frustrating, but Rain felt he should be focusing on his relationship. Crystal went out into the forest with him. It felt like a return to normalcy when she kissed him. She quickly closed off anything else though. It was too weird for her to do anything outside. Rain went home with blue balls. Nighttime came with Lily outside.

"Hey Olive, let's go," Lily whispered.

"They took the clothes from me," Rain said. "What do I do?"

"You have to get them back."

"But they are sleeping in the room with them."

"Fine. Wait here."

Lily left and came back with a potion.

"Drink this to become invisible," Lily said.

The prince drank the potion and disappeared. He sneaked into the fairies' room and took the clothes back. The duo took off for the town again.

"They told me these clothes had consequences?" Rain asked.

"Yeah," Lily answered.

"Why didn't you tell me?"

"I figured you wouldn't go out if I did."

"What is the effect?"

"I don't know."

"How do you not know?"

"I just don't."

Rain thought about calling everything off. He stopped walking to ponder. It was either taking the risk or going home to be in captivity and blue balled.

"Whatever," Rain resigned.

"Great!" Lily exclaimed and hugged him.

They arrived at the tavern. Rain had forgotten his worries with the free drinks he received. Soon enough, he was dancing with another man. Lily watched them from the corner of the bar. This man was much larger than Rain, and the prince was letting him do everything. It was that liberating feeling of getting away with everything that rushed through Rain again. Lily was watching with jealousy as the tall tavern patron took Rain outside.

"There he goes again," Lily mumbled to herself.

She was bitter about it, but was still getting attention from other men. Out in the alley, Rain was pinned against the wall yet again. His heart was racing knowing what he was about to be asked to do. The large man just looked down waiting. The prince looked around, but succumb to the curiosity. He wanted to feel it, so he got on his knees and opened up the man's pants.

Rain was presented with a hard cock in his face. He was not sure what to do with it, so he moved forward and licked it. It bounced in place. He kissed the tip and lingered on it, sucking it gently. Putting one hand on it, the prince opened is mouth wide and put the penis in his mouth. He sucked what would fit in his mouth. His head bobbed on it until the man got carried away. The stranger grabbed Rain's head and pulled him in. Rain's back was against the wall while the stranger fucked his mouth. The prince submitted to the man, and let him do what he wanted.

Drool was running down Rain's chin. He was a sloppy mess getting used like a toy his first time tasting cock. It made him horny. The man was breathing faster. The prince knew he was about to get what he wanted. Rain was hugging the man's hips. The tip was making short strides in Rain's mouth being sucked until the salty taste came. The shaft pulsed in the prince's lips and cum gushed into Rain's mouth. The sudden taste almost made him gag, but all of it was gulped down. When the man pulled out his softening cock, Rain fell forward and gasped for air.

"Take care," the stranger said before closing up his pants and walking home.

It took a moment for Rain to collect himself after that. He wiped his mouth and stood up, then walked back inside to sit by Lily again, who was now alone.

"Welcome back," Lily laughed.

"Yeah," Rain said.

"Are you ready to go back home?"

"Yeah."

The two got up and left.

"So how was it?" Lily laughed.

"Bad," Rain responded.

"Really?"

"I lost control of myself. I feel so disgusting."

"You didn't swallow his cum did you?"

"Yeah, why?"

Lily paused for a bit and stopped walking. She was unsure how to say it.

"You could be close to being marked," she told him.

"Well, I feel fine," Rain said.

"Hopefully."

"When you wear those clothes you run a chance of being marked."

"I thought you didn't know what they did!"

"I didn't want to scare you. You seemed so happy."

"What do I do now?"

"Do not wear the clothes for a week and maybe it will pass."

"Okay."

Rain gave the outfit to Lily, then crawled back in his window. The next morning, he immediately went to see Crystal. She took his mind off it for a little while, but the guilt plagued him. Nobody knew, and it was only sucking a dick. Soon it would be a dumb memory. However, he still needed to relieve his sexual urges, and Crystal was no help.

A week past, and, sure enough, Lily arrived.

"I don't know," Rain said. "What if I do something I regret?"

"It's fine. You'll be fine."

They walked to a tavern in a different part of town. Rain did not want to run into the same men as last time. It was a fresh night in a nice clean tavern with lovely music. The prince had a lot of restraint tonight, but it did not stop the other men from grabbing his ass. He felt proud of himself for staying in the tavern. When the night had ended, he felt much better about everything.

It was time to see Crystal, but she was unreliable again. The prince had lost his patience with her. She would be loving one day and absent the next for no reason.

That night Lily knew Rain was frustrated. She took him to her tree first to let him calm down. He had much to say before calming down.

"Why can't things just go how they are supposed to?" Rain ranted. "Everything is always a game."

"Yeah, I know how it goes," Lily said. "It's okay though. I'm here."

"Yeah," Rain agreed.

Lily moved in closer to hug him. He hugged her back. She reached down and grabbed his ass. Rain grabbed her ass back, then they fell back onto the bed with Rain on top.

"I have to show you," Lily said lifting her skirt and lowering her underwear.

Her cock flopped out half hard. Rain was shocked she had a penis, but went down on it immediately. He felt it get bigger and harder in his mouth. She put one hand on top of his head. The soft skin and squishy tip were fun to play with in his mouth. His tongue worked around the shaft. It was so long since Lily had released she only lasted briefly in his mouth. He tasted her salt start to leak, then she pulled his head up by his hair and held him there to shoot ropes in his face.

Thick cum dripped from Rain's chin until Lily could get a towel to him. He wiped himself off, but was still incredibly horny. Lily was now too relaxed to go out or do anything, so they chatted until he had to return to bed. He felt a little disgusting for sucking cock again, but not as much as when he was chugging the semen.

Crystal was finally responsive today. Rain was groping her butt and boobs in the forest. His dreams were coming true of fucking her. They were partially undressed and his dick was out. He had her bent up against a tree with his shaft lying between her cheeks.

A twig suddenly snapped as if someone was nearby.

"What was that?!" Crystal yelped, standing up straight and pulling her clothes up."

"Probably a deer," the prince said. "Who cares?"

"No, I want to stop."

"Please?"

"No, I feel like I'm being watched. I can't. Sorry. We should just wait until we can safely move to the city."

The prince was livid, but put his cock away, and walked back with her. She left for her house, and he want back to his room. He stomped around screaming until night. Lily came to his window and he hopped out with her without a care. He wanted to forget about Crystal. This time they headed straight to the bar. Multiple men were trying to dance with him, but the tallest of them was assertive enough to ask the prince out. He left the bar while Lily was distracted. Rain was back in the alleyway with another strange man.

The prince quickly dropped to his knees to pull out the man's penis. He spit on it and stroked it with excitement. He licked the shaft and kissed the tip. Both of his hands stroked the stranger's cock. Rain's lips pressed up puckered against the top waiting for an explosion. The stranger moaned like he was coming close. Footsteps nearby could not distract them. Precum spilled against his pouted lips. The prince was rubbing as fast as he could, then opened his mouth and licked the tip as cum erupted. The cock was throbbing in his hands and unloading on his tongue and face. Rain kept tonguing the tip until the semen stopped flowing. After a second to collect himself, the man left without saying a word. Rain washed himself off and sat down waiting for Lily. When she came back, they got up to leave.

"Are you all set?" Lily asked.

"Yeah, let's go," Rain answered.

"I might have tasted more cum tonight."

"Do we need another week?"

"No, I just tasted it."

"Are you sure?

"Yeah, it's probably fine."

He spent another day with Crystal. This time he seemed more distant after last time. They still wanted to be together, but the wait could be over a year. It was a rough time to get through, but it did not stop Rain from being around Lily.

Rain really dissolved into his alter ego. He was perpetually horny, and the men could tell. He laughed his way out the back door as a man eventually carried him out. The prince was put against the wall with a dick in his mouth. He sucked it until the stranger got carried away. Rain was turned around against the wall and the man pulled Rain's underwear down.

"Wait, I was just here to suck!" Rain shouted.

"If you want to act like a horny girl, then I want to breed you like one," the stranger told him.

"But I've never gone that far," Rain protested.

"I'll take it easy on you," the man said. "Just turn around for me."

Rain was thinking about Crystal, and thought about how he was going to take her. Now he was faced with a horny stranger, but the prince could not help himself, and turned around. The larger man bent him up against the wall with one hand on Rain's shoulder and began to push up against Rain's backside. The shaft rested on Rain's ass and was pulled back and up to the rim.

Rain's tight pink rim resisted entry. The tip was about to be forced in when Lily showed up. The stranger quickly put his dick away and ran off. Rain stood up straight with his face completely red.

"I... was..." Rain stumbled, pulling his underwear up.

Lily said nothing and pulled Rain's hand to leave. She took him to her tree again.

"I guess it is good you showed up..." Rain mumbled.

"You really wanted to take that stranger's dick?" Lily laughed.

"Shut up! I was horny and curious."

Lily moved forward and grabbed Rain's ass.

"It's okay Rain," Lily whispered.

"How do you know my name?" Rain asked.

"I have my ways."

"Just keep it between us?"

"Yes."

"Okay. Good."

Lily was sitting on the bed next to Rain. She stared at him for a little bit, then spoke up.

"Horny and curious?," Lily asked, licking her lips.

Rain became worried, but he could not think straight while Lily was sucking on his neck. She pulled her boner out from under her skirt. He wanted to experience her, so he got to his knees. He slobbered on her penis until she got up from the bed.

"Be a good girl and present your ass to me," Lily declared slowly stroking her dick.

The prince got up slowly and took his underwear off. He bent over the bed and pulled his skirt up. Lily walked up behind him and put her dick up against his rim. It poked his backside. The anticipation made him extremely horny.

"I'm going to make you a princess," Lily whispered.

She put her hands around his hips and pushed into his hole until his rim was stretched around her cock. He grunted and squirmed as he had his virginity taken.

"Just relax," Lily laughed. "I'm being gentle."

The prince finally unclenched after a moment of her hard trunk loosening him up. She slowly fucked him against the bed. Rain was crouched and bent against the bed. Lily had moved her legs around his and swung herself into him. She leaned over him and pounded him like he was her girlfriend.

All Rain could do was accept his place of submission having is soft cheeks clapped by his pink haired mistress. Her girlcock worked his prostate and made him drip precum. Lily moaned and panted in his ear.

"I hope your girlfriend doesn't mind if I creampie you," Lily giggled.

He gave a struggled moaned and stood on his toes. Lily was fully railing him until he felt a surging feeling. He felt the blood rushing to his head and climaxed to her thrusts. He contracted on her and gushed cum against the bed. When Lily felt the contractions around her cock, her breathing tightened and she went all the way inside. She gripped his ass tightly and claimed his royal hole with her cum. Her shaft throbbed loads of semen into his boypussy. He was finally marked.

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