Adventures of Dev Ch. 03

Chapter 3: Captured and Captivated

This is an erotic fantasy story told by a travelling merchant and young Dev as he recalls his road to becoming an accomplished male courtesan. It contains homosexual spanking and vivid anal intercourse. If that is not your piece of fictional pie, be advised. If it is, however, enjoy!

*****

After a quick lunch at a nearby tavern, Dev and I returned to the room which I still rented for one more night. My sexual interest in the gorgeous young man had by no means diminished, but for the evening I was contented with hearing more about his story.

"You had just gotten captured." I reminded him.

"Indeed I had." He said as he continued.

*****

"I was still blindfolded, laying face down across a saddle with my hands tied behind my back. Ever since we had set off I had been kicking and screaming through my linen gag. I knew nothing of my captor or his intentions, other than that they were going to be sexual in some way. Fruitlessly, I kept trying to wriggle loose from my bonds and kicked so violently that it disturbed the horse.

"That's enough!" The stern voice of my captor commanded.

Defiantly I kept kicking.

He stopped the horse in its tracks.

"You disobedient, little..." He muttered through his teeth.

Furious, he pulled down my pants just enough to uncover my buttocks. I was completely exposed to his mercy. And I knew that there wasn't going to be any. Sure enough, he started to spank me. But this was nothing like the occasional slap on the ass that my goat herding lovers had given me. This was pure punishment.

Smack! I gasped as his strong hand landed across my left buttcheek. Smack! Smack! Smack! Gods that hurt! Again I tried to wriggle loose, but... Smack! Smack! Smack! On my right cheek... Smack! Smack! Smack! The pain was excruciating. Smack! Smack! Smack! Smack! Smack! Smack! Gods, he wasn't holding back... Smack! Smack! Smack!

Tears began to form beneath my blindfold. I stopped moving as a sign of surrender, perhaps that would make him... Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! The screams of pain beneath my gag were only heard as muffled moans. It felt like my buttocks were on fire. Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack!

I don't remember how long he continued to spank me. All I remember was crying and sobbing like a child when the burning punishment suddenly stopped. Instead it was replaced by a soothing, cooling sensation. He was smearing some kind of ointment on my sore buttocks. The gentle touch could not have been a greater contrast to the rough treatment I had just received.

Then my captor took of my blindfold. At first the sunlight was blinding. It took some time for my eyes to adjust and then I saw his face. It was as if my heart stopped for a while. In my mind I had pictured an ugly and dirty old man, but this man. He had wavy black hair, a well trimmed beard and overall incredibly handsome features. His black cloak and purple jacket hinted of a muscular upper body. And then there was his eyes, his steel grey eyes, the strongest yet the kindest imaginable.

"Can I trust you not to scream?" He asked kindly.

I nodded, gawking like a fool.

"Good lad." He said and carefully removed my gag.

He smiled approvingly as he saw my face for the first time. I blushed.

"I... I'm sorry if I startled your horse." I stuttered.

"Your apology is accepted." He said. "However, your punishment isn't over." Suddently he reached for one of his saddle bags and pulled out a leather whip. Two dosen straps with knots at their end.

"No, no, please sir... Sire! I promise... No more... Please!" I involuntarily clenched my bright red buttocks, which hurt terribly.

"I would relax if I were you." He said with a slight smile. I saw him spreading some ointment on the handle of the whip. He wasn't going to whip me. He was going to penetrate me! Knowing that it was going to hurt even more if I clenched I tried my utmost to relax. The cold metal knob sent chills throughout my entire body as it entered the rim of my anus. I gasped, but didn't scream. He continued to push the handle deeper and deeper inside of me. My body tensed up so hard I though my spine would snap.

"Keep that in for the remainder of the day and I will forget all about your behaviour earlier. Do you understand?" He asked with a soft voice.

"O...Huh... Okay." I panted.

His face immediately became stern. He gave the handle a quick twist.

"Yes, Sire!" I corrected myself. The sharp pain made me jump.

"Good boy." He smiled.

The wooden handle pressed uncomfortably against the walls of my delicate rectum. It felt rough, nothing at all like the smoothness of a penis. Nevertheless, I fought with every fiber in my body to keep it in. Partly because I didn't want to suffer another spanking. And partly, because for some odd reason I didn't want to disappoint my captor. Therefore, I clenched my anus and buttocks as hard as I could.

We rode off again. The straps of the whip kept hitting my thighs. I realized that the whip must have looked like a horse's tail, protruding from my backside. It was utterly humiliating, but somehow I also found it strangely tantalizing.

During the ride I noticed how my captor kept glancing down on my ass. I wondered if he did so because he found it attractive or because he was checking so the whip didn't slide out.

My posítion across the saddle, not to mention the whip handle, made the ride very uncomfortable. I tried to focus on the passing landscape as our journey continued, further and further away from home. I had never before seen the beautiful fields of the lowlands, nor the majestic distant snowcapped mountains which marked the northern border of the Tarin kingdom. Had the situation been different, this would have been the most exciting adventure of my life.

My heart jumped as I saw some peasants working in the distant fields. Perhaps they could help me or at least call for help. But then I realized that my captor wasn't trying to avoid them, instead he was riding straight towards them. Then I remembered my incredibly embarrassing situation. These complete strangers were going to see my naked behind! Not only naked, but punished to a bright red and stuffed with a whip handle!

I began to panic, but my highborn captor preempted my anxiety.

"Are you going to behave and be polite?" He asked.

"Yes, Sire." I whimpered.

"Good lad."

"Gods be with you, Sire." The peasants said in unison. They did not seem to react much to me at all, and for that I was grateful.

"Good day, kind yeomen." The rider replied.

"Long since we saw you around these parts, Sire." The village elder said.

"And even now I am only passing through. I was made an interesting offer by some local herders."

"O, I see." The old farmer turned towards me. "A lovely specimen, Sire." To my horror he walked up towards my hanging head and started to examine me. "Very beautiful, indeed. My compliments, Sire."

"Thank you." My captor replied.

I hardly dared to look up, but managed to glance quickly. To my absolute dismay and desperation I saw two cute girls my own age in the crowd. They were whispering and giggling at my utter humiliation. My face became so red that it must have competed with my buttocks.

"Ladies, is something funny?" The highborn man in the saddle had also noticed them.

"Hush, girls!" The village elder reprimanded them.

"We're sorry, Sire..." The girls tried to restrain their giggles. "We were only wondering whether he had been punished or been sitting in some nettles."

"Unfortunately your first guess is correct. And furthermore..." I thought I was going to die of embarrassment as he held up the straps of the whip in demonstration. "You cannot see the handle, unfortunately, but I assure you it has been planted deep."

The girls burst out into laughter and so did the rest of the small village.

"I still you have still got your special touch." The old farmer said laughing. "May good fortune continue to smile upon you, Sire."

"And you. May your harvest be as good as mine." He patted me soundly on the butt and waved as we rode off.

My blood boiled. I thought I couldn't hate anyone more than I hated him. Even my anger towards Rin paled in comparison. But then he spoke.

"You did good back there." He said softly. "You were put in a extremely humiliating position, but you endured with dignity. Your behaviour was exemplary."

And there it was again. That warm and satisfying feeling I somehow got from the appreciation by this complete stranger. Why? I couldn't explain it myself. But there was some irresitable and mysterious force surrounding this man. I felt it with every bone of my body.

After several hours of riding we stopped for the evening. He lifted me down from the saddle and loosened my bonds.

"Please take of your shirt and pants." He commanded.

He had already seen my most private parts, so I complied without much hesitation. I was now completely naked, save my sandals. I tried to seem brave, but my heart fluttered nervously as his eyes wandered across my body.

"Now turn around and bend over." He said gently.

I didn't dare to do anything else but comply. I turned around and started to bend forward while struggling to keep the whip handle inside. The struggle made my buttocks strain and reminded me of the soreness.

"No, no. Legs apart and back arched."

"It will slip out..." I whimpered.

"No, it won't." His voice was stern and yet comforting somehow.

I planted my legs apart, arched my back and carefully bent forward. I panicked as I felt the handle starting to slide, but it suddenly stopped as the wide knob reached the inside of my sphincter. I was so relieved. I didn't know how I would have endured another punishment.

"Now part your buttcheeks."

My hands felt like burning iron as I put them on my reddened behind and parted my buttocks. I had never felt so exposed. Then he moved closer to me and knelt down right behind me. I could feel the heat from his breath.

The handle moved inside me as he gripped it and carefully started to pull it out. Then, without any warning, he pushed it back in again. I jumped! Then slowly out. My legs were shaking and for some reason a strain of transparent sticky fluid started running from the slit in my penis. Gently, he pulled harder. I felt my anus pucker outwards as it clenched the round metal knob. I bit my lower lip and squirmed as the wide knob popped out. A loud plop left me twitching.

My captor smiled as he rose to his feet and looked in admiration at my exposed opening. Once his eyes were satisfied he ordered me to stand up and turn to face him. The gentle smile which met me warmed my heart.

"I think we got off on the wrong foot." He said. "Let me introduce myself. I am the Chevalier Ilario. And you are?" His steel grey eyes looked straight into my blue, as he reached his hand towards me. They were almost hypnotizing.

"Dev, Sire." I said, blushing as I took his hand. I hated myself for blushing.

"Listen, Dev... I am sorry for carrying off with you in such a brutal manner. I stand by my punishments of you, but I can understand your confusion and reluctance to being here right now."

I was confused. I thought he was just going to kidnap me and then have his way with me. Not try to explain himself to me.

"I am going to be honest with you, Dev. My intent is simple. You see, for generations my family has trained beautiful young men, like yourself, to become professional courtesans. And courtesans are the finest in Tarin, which brings our family fame and honor. Normally I do not buy recruits, but when your... friend.. contacted me and described you, I was tantalized. And now that I have seen you in the flesh, so to say, I am not at all disappointed."

I felt flattered by his compliments, but at the same time appalled by his family's immoral business. Not befitting a chevalier, if he even was one. As a boy I had heard about the depraved women in our village. Those who sold themselves to men for a few coins. I was not going to become like that.

"However, because of our rough start." He continued. "I will make you an offer now which I normally only give recruits after the first month of training. You may leave at any time and return to your life as a goat herder. Return to your family and friends. I would not hold it against you, especially since our training programs are rigorous and demanding. Only the very best pass."

It sounded like a challenge.

"However if you do pass, you will live in my family mansion. There you will see, taste and experience far more than any young goat herder could ever hope. And that arrangement is for life, even when you have stopped working as a courtesan."

He paused, again looking straight into my eyes.

"From what I have seen and heard, Dev... with the proper training, you can become one of the greatest courtesans who has ever lived. However, that decision is completely up to you. It is seven days until we reach my estate. You can decide at any moment up until then. But once we have arrive the rules will change. Do you understand your choices?"

"Yes, Sire." I said and nodded, struggling to process all the information he just had presented me with.

"Here. For the pain." The chevalier reached into his saddle bag and handed me a clay jar. It contained an ointment. I figured that it must be the same soothing balm he had used on me earlier.

"Would you be so kind to gather some fire wood, while I build a fire place?" He asked.

"Of course, Sire." I said.

Darkness had begun to fall as we sat by the fire. He sat, I was leaning on my hip. Thinking that he had already seen most of me, I got up to rub some of that ointment on my sore backside. I pulled down my white linen pants. In the light from the camp fire I could see how red my buttocks were. I whimpered as I began to massage the soreness. Then I saw him, staring at me from the other side of the fire. Slightly embarrassed, I smiled. Until then he had not noticed that I had seen him, now it was his turn to become embarrassed. He quickly turned his head.

"Time to sleep." He said.

"Good night, Sire." I answered.

Did he desire me? And if so, why didn't he want me to see that?

Laying on the back immediately proved impossible so I layed down on my stomach. But the questions kept me awake. I couldn't decide if I was just going to slip away tonight or if should stay until tomorrow and say my farewell then. But why should I show any such courtesy to a man who had bought me, violently spanked me and paraded me in front of an entire village? Then again, his offer did sound... exciting... interesting... adventurous... And was my life with my so called friends, really any better? Their only real interest in me was sex anyway. And they couldn't possibly offer the lifestyle and adventures like this man could.

The chevalier had fallen asleep. I leaned my head to look at him. I wondered how he could be so confident, so unafraid. As far as he knew I could be plotting my revenge and try to kill him in his sleep. But I guessed that he was the kind of man who even slept prepared for every eventuality. The fire highlighted his handsome features. His powerful chest was heaving.

I renewed my attemtps to go to sleep. But my anus felt a bit tender after having clenched the whip handle all day. Silently I grabbed the ointment jar, took a dab on my fingers, reached inside the back of my pants and started rubbing the rim of my sphincter. It felt soothing. More than soothing, it felt nice. As I rubbed, my penis started to get more and more erect. My middle finger circled my rim, even entering briefly. For some reason which I still to this day can't explain, I started to fantasize that it was his finger massaging me. The thought made me even harder. Quietly I rubbed my erect penis against the ground. I looked at his strong arms and heaving chest as I massaged ever more intensely. In my mind I was moaning his name, "Ilario!". I reached around with my other hand to rub my dick. With my eyes fixed on the captor, I was working myself with both hands. One on my penis and the other fingering my anus. Suddenly, I came. I had to muster all my energy not to scream out loud. Cursing myself, I looked around for something to dry my hands and pants with. But the hard days ride had made me so exhausted... I figured the semen would probably dry until tomorrow...

*****

I woke to the smell of something frying. My mouth was watering. In a blur I saw the Chevalier as I opened my eyes, and without thinking I smiled. To my horror I discovered that I still had my hands down my pants. I quickly pretended to scratch myself. But I don't think he bought it.

"You must be hungry." He said.

"Thank you, Sire."

The bruises from yesterday's spanking stung as I sat up.

"Here you go." The Chevalier handed me some bacon and sausace on a plate together with small loaf of bread.

"Thank you, Sire." I repeated. Not haven eaten in a day I sunk my teeth into the breakfast like a starving animal.

"So you decided to stay?" Chevalier Ilario asked.

"Well, it's very far back." I tried to justify it to myself.

"I can take you back if you want." He said looking me straight into my eyes.

"Well..." I looked down. "I mean... I don't really know if I want to become a... a courtesan. But I know I can't see myself as a goat herder."

"So you agree to submit to my training?" He asked.

The word "submit" sent chills down my spine.

"Do I get to change my mind during the training?" I asked.

"You get to reevaluate your undertaking once every month." He said.

"Okay." I said. "I agree to your proposal, Sire. But I have one condition..." I added.

"That's a bit impudent, but alright?"

"I want to sit in the saddle. Riding." I didn't know how he would react. I braced myself.

"Do you even know how to ride? And moreover, can you sit?" He asked smiling.

"Anything must be better than laying across the saddle. Please, Sire." I implored.

"Alright." He seemed pleased with my decision to stay, but I had hoped that he would be more excited. Had I misread his attraction yesterday?

After having put out the camp fire and packed the utensils, he helped me up in the saddle.This was completely different from laying across it. Instead of feeling like an extra saddle bag, I could feel the horse's strength beneath me. The chevalier swung up behind me. I could feel his body press against mine. A warm feeling ran from my belly up towards my chest as his arms embraced me when he reached for the reins.

"Try to follow the movement of the horse." He instructed as his steed started a slow walk.

He had been right in his suspicions, I didn't know the first thing about riding. When the horse started to trot I was completely out of pace, jumping up and down in the saddle.

"Try to follow my movements instead." The Chevalier suggested.

He pushed forwards towards me. My heart jumped as I felt his groin against my sore buttocks. His thin riding pants in black silk did little to conceal his manhood. Pressing against my pants of equally thin white linnen, I could feel every contour. Gods, it was big! Still soft, his penis must have been three fingers wide. Again he pushed forward. I was still out of pace.

"Try to be a bit earlier in your movements." He instructed.

I tried to follow his movements the best I could, but being to slow he kept bumping into me. To my surprise, the heat from my ass started to made him hard. My eyes widened as his massive penis started to grow. I felt it rise straight inbetween my buttocks. I glanzed back, expecting to see excitement in his face. But instead I saw embarrassment. He was embarrassed! Embarrassed that he couldn't control his lusts.