Sissy Prince Pt. 01

This story might not be for everyone (see tags), but I hope you like this new idea.

If this is not your cup of tea, simply skip it. There are plenty of other good stories around. If you decide to risk it and like it, please be kind and leave a comment or just vote.

All the characters are 18+

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Once upon a time, there was a prosperous kingdom named Arran. It was ruled by a wise king. The king and queen of Arran had one child, Prince Ollie.

One day, the prince was playing in the yard. The birds were singing around the calm water fountain where the prince was right after it. The prince loved to play with sand and dolls, sometimes he talked and sang with the singing birds too. Suddenly, a snake came from the fountain crack and bit our beloved prince.

The Prince cried out loud and ran back to the castle. Everyone was freaked out about what was happening. The Prince told some soldiers to take him to a healer that he had bitten by a snake. The news about the prince and the snake spread like the wind throughout the kingdom.

The healers were unsure of exactly how to proceed, because the prince, shocked as he was, could not provide them with any details about the snake. But the royal healers were good at their jobs, and they saved their kingdom's only prince. The king and queen were so relieved that they gave those healers some land in the kingdom's rural area as a reward.

But at the end of the day, the prince didn't wake up at all, and his body seemed lifeless. A day became a week, and then became a month. The king called for all the healers from his kingdom and beyond. The kingdom suffered from this horrible situation for over two months. Finally, the prince woke up, but at a great cost.

The kingdom of Qentis was Arran's most hated enemy. Its rulers lusted after Arran's fertile lands and its rich gold mine. Despite their long standing enmity, they had answered Arran's call for healers nevertheless. However, Qentis's rulers had demanded that if their healers cured the young prince, then the king of Arran would have to accept their own baby princess as a daughter-in-law in the future. So desperate had been the king of Arran that he had accepted their terms.

The prince got well soon, but the king ordered his king guard to resume his son's training. It was the queen that actually took the decision to put her son out of the training in his puberty period because she didn't want something terrible to happen again. The queen somehow managed to convince the king to resume the sword fight till he became a man.

Before the accident, the royal guard showed the prince no favoritism in the training session. They had him train amongst all the other young lads of the palace. All the other boys took to the lessons like fish to water and some of them had already passed their puberty. The young prince, on the other hand, showed no ability, nor even the will. He would only try to avoid blows and hide behind his shield. His trainer did everything to force the prince to stand up and fight back, secretly cursing the prince in frustration the whole time. It was to no avail. The prince wailed and sniffled behind his shield. Even the other boys' laughter could not shame him into making a real attempt.

Prince Ollie was beginning puberty. His limbs were growing out of proportion to his body, making him clumsy. That was something that happened to many boys, but before something really changed like a man, the prince had his terrible experience with a venomous snake.

The treatment was good enough to save the prince's life but also took something from him without anyone noticing. Even the 18th birthday of the prince didn't bring any luck to his puberty, but his training session had started once again. Meanwhile, the prince was enjoying his training-free life until he received the king's order. Because he now needs to train again, this time with younger lads. All of his buddies and classmates became knights or warriors.

Once again in the training ground, our prince was trying his best to show the little boys who's the prince. But they had all mocked him, calling him a coward and a young girl, calling him wimpy and a sissy, and threatening to beat him if he ever met them on the tournament grounds. However, none of them ever had the opportunity. The strong, swearing royal guard may have pushed the prince Ollie in and let him get beaten unfairly in the hopes of turning him into a man. The queen tried to hide her son's inability from the king, because her son was the only reason that the king didn't get married with another woman.

The queen had different plans for her son, the prince of the Kingdom. It wouldn't empower the regular people to witness their prince kneeling, weeping, and pleading not to be beaten by little boys. The queen decreed that Prince Ollie would not go out to practice with the other lads in the morning. Instead, he would spend a couple of hours in the library, either reading, or posturing himself in front of the mirror, combing his long, beautiful golden hair until it gleamed and caring for his milky-white complexion. Alternatively, he would go to the chamber where his mother and her friends were embroidering and converse and laugh with them, flattered by the women who were his mother's age. It was far preferable for him to be wounded and sweating in the dirt.

The queen was enjoying the time with her son and her maids but after all she was also worried about the kingdom's future. Prince Ollie must be the man, and secured the kingdom's heir. She called their maester the head of healers to talk about her son's transition.

"My queen, you wanted to see me," maester said.

"I'm worried about my son, our prince," the queen replied. "He's already passed his 18th birthday but still looks like a little princess."

"My queen, I understand if you want me to talk with the king," maester said.

"No, no... then why did I call you in the first place," the queen said. "I want you to bring out the man out of my son. Can you do that?"

"My queen, I'll do anything for our prince but first I have to ask our king," the maester replied. "The king has a direct order on every one of us, anything to do with the prince."

"No, this is only between us, you and me, not even the prince," the queen said. "I'll give you anything, gold, land, girls...boys, just name it."

"My queen, if I could I would," the maester said. "Even I have to mention this to the king or..."

"I know what you want, maester," the queen replied and started to strip her gown. "Like what you see."

"My queen, I'm sorry," the maester apologized.

"You sure, maester, you don't want to play with these big perky boobs," the queen teased. "How about my pink tight pussy? You personally keep this pussy tight for your king. Do you want to see how it feels inside?"

"My queen!" the maester said while eye fucking the queen's naked body.

"It's so rude to decline a queen's offer!" the queen said while rubbing her wet pussy.

The maester got into the bed; touched the queen's leg and started going up.

****Queen perspective.****

He gently pushed his hand between both my thighs, and even though my thighs were clamped like a trap, I could feel his fingers getting higher with each passing flash. He pressed his fingers on my warm pussy as he slid his fingers farther between my legs. As the maester began to touch me, I struggled to regulate my breathing. My heart was pounding in my chest, and my large breasts swept against his.

A shudder ran up my spine as the maester's index finger drew a relentless trail up and down my slit, and an uncomfortable tingling feeling began to rise inside me. Something had to give between the numbing effects of the wine I was drinking and my efforts to remain undiscovered. My thighs' muscles began to relax unconsciously, gradually loosening the strain on his hand.

The maester rolled out his fingers, softly spreading my legs apart, sensing my stillness. With more freedom to travel, he decided to explore more seriously. He pressed his middle finger between the lips of my pussy and started pushing it inside of me. With my legs spread wide and my hands on my chest, toying with my firm nipples, the maester pushed his advantage, burying the second knuckle of his middle finger within my warm, velvety hole.

"Tonight, you're going to become who you are, my queen," the maester stripped his royal healer uniform. "So, my queen wants to serve me?"

I gasped at his long, thick, semi-erect cock that I had seen many times before at the king's orgy. But never this close before because the queen must keep her integrity and kingdom's pride. "I want to serve you, maester," I replied. "Allow you to use me as one of your slave girls in exchange for treating my baby how I desire."

"In that case my queen, I think I'll have a great time with you in private or public?" the maester asked.

"Both. Whatever and wherever you want, I am just your willing slave girl, waiting for your command," I replied and my shaking fingers came in contact with the maester's rock hard shaft. "I can't wait to watch my ass get spoiled! I'll be your sex slave for as long as you want!" I looked him in the eyes as my fingers grabbed and rubbed the center of his shaft. My petite fingers hadn't yet made the heady trek from top to bottom; I was still attempting to comprehend the incomprehensible circumference.

"That feels great, my queen!" the maester murmured as he massaged my swollen tits and checked the seductive curve of my amazing ass cheeks. Then he grabbed the back of the head and pushed his tongue inside my mouth.

"Yeah, it does," I said as my tongue withdrew from his mouth and I circled my glossy lips softly. My attention was drawn to his captivating eyes. At this point, my hands had reached his thick cock's head and were stroking and squeezing its fullness.

"Taste what's leaking out, my queen!"

I wiggled my tongue nervously around the tip and drank at his pre-cum. "Mmm..." he heard from deep within my throat. He growled in approval before stroking it more vigorously around my wet tongue and firm lips. I opened my mouth to show him the wetness within. encouraging him to come in. I couldn't wait any longer.

"Do you enjoy sucking servants' cock?" He noticed my apprehensive eagerness on my face.

"Show me," the maester murmured, pressing the big cock head against my delicious lips. My lips suddenly extended so wide that breathing became impossible. His size challenged my talents, but I quickly learned to breathe via my nose while still tickling the soft bottom with my tongue to his grunting satisfaction. He pressed harder, but despite my best attempts, he quickly realized that I was going to need a lot more practice with a big cock.

He enjoyed it like that, and despite my lack of expertise, he liked the way I looked with his massive cock in my mouth. "I'm shocked you're not more at ease sucking cock, but I'll train you... I'll show you how to use your mouth to enjoy a massive cock, my queen! Spit on it, my slut queen...mmm...now lick and suck on it!" He moaned as he pinched one of her huge tits.

The maester forcibly pulled his hard cock out of my lips and placed me on my back on the edge of the bed. He took a minute to take in the beauty of his queen's nude body before gripping my thighs and slowly pulling them apart. I had a lovely gleaming pink pussy lip. He enjoyed how my modestly swollen outer labia led to my overly plump inner lips. He stretched my legs wider before laying his head on his queen's pussy for perhaps the first time and eating it. The maester occasionally knocks me unconscious in order to check and cure my immaculate royal body so that it does not age.

Before long, my ass lifted off the bed as I attempted to strengthen the bond between my pussy and his lengthy tongue. He'd already pushed me over the limit a few times, and while he waited, I begged him to make me orgasm. "Please, maester, I beg you, please let me cum," I pleaded, my hips frantically rotating and my hands plastered over my boobs.

The maester had to suppress a giggle as his queen's cries revealed her desperation. He considered eating my lovely cunt to release me, but only after several orgasms with my tight pussy impaled on his massive cock.

He massaged his enormous spongy head up and down my wet slit, paying particular attention to my swollen clit. "Oh my God, I need you in me...maester."

"Take one final deep breath before I push my big thick cock push inside you, my queen," the maester commanded.

"Ohhhh myyyy Godddd...please go slow...shit...ohhhh," I groaned as the swollen head sank past my stretched lips. He slammed his rock-hard cock into my tight pussy inch by inch, my calves propped up on his shoulders. He proudly observed as my beautiful face writhed in an endless array of excruciating yet joyful visual responses that matched the gasps and groans exiting my wide open lips,"... slowly... fuck... uhn... ohh... ohh."

"Fuck, my queen, your pussy is so tight."

"Oh maester... uhn... uhn... God... I've never felt anything... anything that huge... ohh... ohh... yes..."

"Don't you feel better now that you know what you've been missing all this time?" He moaned.

"You're so large... keep going slow... it feels so amazing, but it aches too!" I merely nodded.

"Don't worry, my queen; once this tight pussy goes all over you, the only thing you'll feel is heaven. You're not going to want to give it up!"

"Oh my God..." As the maester started slow in and out motions with approximately a quarter of his cock now buried within, I moaned.

Maester began to see the unmistakable signals of an imminent climax appear on his queen's magnificent face as his big cock reached the finishing line and unleashed my swollen clit from its luster. My breathing became heavy, and my groans became more pronounced, as my hips swayed ever so rapidly, attempting to balance the incredible pleasure I was experiencing with the dull discomfort of being so totally loaded.

His cockhead had already penetrated newly discovered areas within me, and his thickness was not delicately deflowering them. Never having been tried before, the ballooned cock knocked violently along nerve ends that immediately soaked it in fluids.

We were working to perfection, "Fuck, my slut queen, your tight pussy feels so damn amazing!" he said as he buried his cock in my magnificent greeting party of slick fluids combined with pussy.

The maester had fucked hundreds girls and women in his life, but he couldn't recall ever feeling more excited at the idea of a bitch creaming on his massive cock like his queen was about to, "Go ahead, my queen of sluts. Let it all out, and smear that all over my cock! I'm almost there!"

"Oh My God... I'M CUMMING, maester!" My whole body trembled fiercely, and a blast of juice gushed out copiously along the edges of his deeply inserted cock and my clit.

"Holy fuck!" he yelled as he yanked his big cock from between my gaping lips, a rush of pussy juice squirting into the sheets. That's what I mean by "queen of slut!" He applauded.

My head was still stretched backwards against the covers, my mouth wide open, fighting to restore the oxygen that had been pounded out of my lungs by his marvelous cock.

With his cock still buried inside me, he glided my limp body up to the center of the bed. My pouring climax had aided in a much deeper penetration by his enormous cock, the majority of which was now blended by my still eager pussy. He resumed where he'd left off, pounding straight through my climax. My folded legs were now opened wide as he lifted my legs over my head with his powerful arms. He's extraordinarily powerful for his age.

For the first time in my life, I felt as if my body was being used entirely to generate pleasure for a powerful guy who understood just what to do with it. My desire to satisfy him outweighed even my own pleasure. "Uhn... mooan... your big cock feels amazing. I love the way you fuck me!"

Maester started fucking me in long, slow strokes, plunging himself more and deeper with each thrust. I couldn't believe that after my splashing orgasm, I was still so tight and filled with lust. My chamber was filled with groans and wet smacking sounds since my pussy had gotten fully waterlogged as a result of my climax and his ensuing hammering. "Holy shit...it's so deep maester...so deep...oh god! I can't believe I could take it all..."

"Oh, you can take it, and you'll take it deep all night!"

"Oh, yes... fuck me... fuck me more... Oh no... you're going to make me cum once again!" Another massive orgasm was brewing deep within my pussy.

"Flow that pussy juice all over my cock again, slut!" he roared as he battered his queen's royal hole.

The maester couldn't stand seeing me in the throes of pure sexual decadence, with my huge gorgeous tits jumping across my chest while thrusting deeply into my squirting pussy. "Your tight, moist pussy is going to milk it straight out of me, my slut queen!" He gasped, flexing every muscle in his body. As he dumped a flood of cum inside of my pussy, the head of his cock swelled.

When he took his cock out and we dropped on the bed, my copious fluids spilled out of my well-fucked hole once again.

We both struggled to regain our breath as I was saying, "fuck, I ain't going to have any dry spaces to sleep in tonight!" We both chuckled breathlessly as we looked down at the mess on the bed sheets between my legs.

"Who said we'd be sleeping?" The maester responded with a mischievous, vicious smile that hinted at the possibility that he wasn't joking."There's no feeling in the world like fucking a queen and cum inside her."

******Queen Perspective End.******

The very next morning, the maester started treating our prince. It'll take a long time to bring back the prince's puberty once again but the maester was using the queen as his bitch. Almost a year later, the prince was in the maester's lab and stood nude for his regular health examination.

The young prince's changes didn't come as expected. Indeed, many of them should not have been happening to him at all. Fat collected around his hips and thighs. His muscle mass and strength started decreasing instead of increasing. Additionally, his arms and legs appeared smoother, because the fat below their skin became thicker. As the fat under the skin on his face increased and shifted, the prince took on a more feminine appearance.

Prince Ollie's testicles were also shrinking to approximately less than half their original size.These changes kept happening over time. In the first stage, the tip of the nipple was raised. Then buds appeared, and the breast and nipple were raised. The dark area of skin around the nipple (the areola) gets larger. At stage three, the breasts were slightly larger, with glandular breast tissue present. After that, the areola and nipple become raised and form a second mound above the rest of the breast. In addition to all the other changes to his body, the prince's personality also started to change.

One day, Prince Ollie stopped wearing clothes and he spent almost all of his time in his chamber, naked. The queen realized very quickly what was happening to her son. His transformation was quite familiar to her.

"Are you alright, sweetie?" The queen entered the chamber and asked Ollie.

"Mother," Prince Ollie replied. "I'm okay! Just my clothes are irritating to my skin."

"How about this blanket you're using to cover yourself, does it hurt?" the queen asked. "It's so soft and silky."

"No, mother. It feels very nice. It's soft and light," Ollie replied. "Why don't they make a dress out of it?"

"Girls," the queen called out to her maids. "Bring some dresses made of silk for my baby."

"Forgive me, my Queen. They don't make it for men," the maid replied.

"Just find something for my naked baby," the queen ordered. "My baby, you're growing up so fast. I haven't seen you naked for months. Come here and let me see my baby's grown-up muscles. Oh! The girls came back with lots of nice dresses."