I had been on the streets since I was little. The master that had taken me in was stern but fair, he was also a master thief. As I grew older I learned the art of a pick pocket and a sneak thief, I also learned to open locks. By the time I was fourteen I was a junior master but Master Eric saw the change coming to our city and we left before the purge began.
I was surprised when he turned me over to the three mercenaries but he only smiled, "listen son, listen and learn everything they can teach."
I watched him walk away and my training with weapons began. There was the staff and dagger and then sword and bow. It was six long years in many places where men and even armies died. I finally walked away with a couple of very heavy pack saddles filled with jewels and treasure. The large city I went to was inland beside a large river.
I led a horse through the wide gate and nodded to the guards watching everyone enter. I had a lot of time to think about what I was going to do, first was to rent a room. I was able to get a large attic room in one of the better taverns beside the river. After that I went to the King's keep and asked to speak with his chancellor.
From there I was sent into the city where I spoke with a large man that was one of the king's knights. He was now the bailiff of the city guards and gave me a job. Of course since I was both new and young I would have to start off working at night. The first night the other guard that walked with me began teaching me and pointed out an area they always had trouble in.
From the first time I saw it I knew why. It was where the city's thieves guild was. Mostly we just dealt with drunks or brawls. It was a month later when we walked up as three men fought in the street. I moved forward quickly and pulled my night stick. I slapped it along side one man's head and he dropped to the street.
I had the other two mens attention and gestured, "back off and drop the daggers."
It usually works but this time one lunged towards me. I slapped the dagger away and slugged him in the throat as I stepped in. He dropped to the street choking as the other man leaped towards me. I spun and let his weight carry him past me before bringing my stick down on the back of his head.
The other guard stepped in and knocked the choking man out before we secured all three men. My partner looked at me and then grinned, "do you know who these men are?"
I shook my head and he laughed, "three of the thieves guild under masters."
I glanced at them before kneeling to search them carefully. I know places to look that brought out hidden lock picks and a few small knives. Those brought a few more charges when we hauled them before the night magister. They were sentenced and taken away as we went to report to our lieutenant.
I was walking home and had almost reached the tavern when the girl drew my eye. She was new to the city and her clothes were almost thread bare as she shivered. She hesitated before moving towards me as I came closer, "do you want a woman mister?"
I stopped to look at her, "have you done this before girl?"
She was blushing and licked her lips, "aye."
I stepped closer and reached out to lift her face so she met my eyes, "what was that?"
She looked at me and then almost whispered, "no."
I nodded, "are you by yourself?"
She glanced around and shook her head, "no sir."
I glanced towards the alley she had come from and saw another girl a little younger. She looked a little better fed but was still ragged. I sighed, "bring her and come with me."
I let her go and she hesitated before gesturing to the girl. I started walking and glanced at the two girls before walking into the common room of the tavern, "Sasha!"
A slim woman opened the kitchen door as I walked to a table, "Trent?"
I smiled, "three large bowls of warm oatmeal with tall glasses of milk."
She looked at the two girls and back at me before frowning and disappearing. A moment later she was back carrying a tray. The two girls sat across from me as I relaxed and stretched my legs out. Sasha put everything on the table and smiled before heading back to the kitchen. I watched the two girls wolf the food before eating.
When I was done I could see the girls were barely awake and stood, "come."
I led them to the tavern jakes and then into the bathing room. I stripped as they stood looking at me and shook my head. I pulled the rags they wore off them and turned to pour hot water into three tubs. I added cold water until it was cool enough to use and turned to push the girls towards the other tubs.
I sat and began to wash and a minute later they started cleaning themselves. When I finished and got out to dry off the two girls reluctantly stood and stepped out. I dried them and wrapped a towel around each before pulling them after me. I closed and locked the door into the attic and tossed my clothes into the deep basket beside the door.
I pulled the two towels off the girls and pushed them towards my bed. I went to my clothes press and pulled out my brush before walking to the bed. I sat them both on the bed before sitting behind the younger girl and started brushing her hair, "what is your name?"
She was trembling but turned her head, "Ruby."
I nodded and kept brushing her hair and pulling the knots out as I looked at her sister, "and you?"
She looked from her sister to me, "Sapphire."
I smiled and continued what I was doing. When I finished I moved and pushed Ruby into bed, "under the covers."
While she did as I told her I moved behind her sister and started brushing her hair. I pushed her towards her sister when I was done and started on my own hair. When I was done I put the brush away and went to pull the dark blankets over the windows. I slipped into bed with a sigh and relaxed. It was early afternoon when I woke and Sapphire was snuggled against me.
I looked at her and turned to caress her softly. She sighed and began to moan as I turned her onto her back. I caressed her firm breasts before feeling her mound. I pushed the covers back and slipped down in bed. I moved between her legs as I pushed them open. I licked her fuzzy pussy and began using my tongue against her clit.
She was moaning louder and her hips started to lift. I used a finger to slip into her and felt her maidenhead before using my fingers to open and stretch her pussy. She groaned as I continued licking and teasing her clit. Ruby shifted beside us and her head moved down to rest on her sister's hip.
I smiled at her before capturing Sapphire's clit and sucking. She jerked and arched her back as she cried out, "oooohhhh!"
She shuddered and jerked as she thrashed around. I stopped and moved up her body as her sister moved and shoved into her hard and deep before stopping. Sapphire screamed and clutched at me as I held her while she wiggled and struggled and I kissed her, "relax."
She whimpered and tried to relax but I knew she was not. I kept kissed her and glanced at Ruby as she stared wide eyed. It was awhile before I felt Sapphire's pussy squeeze my cock. She looked at me in surprise and I grinned before I pulled back and thrust the rest of the way into her. I stopped again as she winched and started kissing her again.
When her pussy squeezed my cock once more I began to fuck her slowly. She clutched me and a minute later moaned and shivered as her tight pussy rippled around my cock. She was lifting her hips as I continued to fuck her and her pussy was a lot slipperier. She shuddered and jerked and I kissed her before pushing into her and humping.
She shuddered and wrapped her legs around my waist, "aaaahhhh!"
Ruby giggled, "does it feel good?"
Her sister laughed and shook me, "yes."
I went back to fucking her as my balls tightened. A minute later she was thrashing around and bucking. I thrust into her and pushed before my cock erupted. Sapphire lifted her hips and tilted them as I kissed her passionately and began to pump cum into her. She clung to me long after her womb was full and I sighed before pulling out.
She groaned and shivered before smiling, "it felt a lot better after the pain went away."
I smiled as I turned and pushed Ruby onto her back, I kissed her and slid down in the bed. She spread her legs hesitantly and I leaned in to lick through her pussy. I continued to lick her and used my thumb to rub below her pussy. When I pushed my tongue into her I felt her maidenhead missing as she squirmed and moan.
I captured her clit and sucked as she lifted her hips. I kept teasing her and licking until she pushed my face away. I moved up her body and kissed her, "have you done this before?"
She shook her head as Sapphire touched my shoulder, "you can use me again."
I glanced at her before lifting and slowly forcing my cock into Ruby's pussy. She shuddered and hugged me as her extremely tight pussy squeezed my cock and I smiled, "hurt?"
She groaned and shook her head, "I feel really full though."
Sapphire bit her lip as I began to fuck her sister. She sighed and shuddered as she lifted her hips, "mmmm!"
I continued to fuck her as Sapphire grinned, "like it?"
Ruby was jerking and shaking as she wet me and her pussy grasped and milked my cock, "yes."
I kissed her and began fucking her with long strokes. She howled and clutched me as my thick cock slipped in and out easily. She wrapped her legs around my waist as I kept fucking her and started to press and hump into her deeper. Ruby wailed and began to convulse, "aaaahhhh!"
I continued to fuck her grasping pussy as Sapphire giggled, "you sound like me."
.... There is more of this story ...