I arrived slightly earlier than I was meant to. After our first meeting I had been given specific instructions. Jack had allowed me to shower and change back into my normal clothes. Once I had returned to the kitchen, I found a note with a key.
"Today you excelled yourself, but you have more to learn. Next week on Monday you are to come directly here after you finish for the day. I will arrive home at 6. Here is the key. Instructions will be waiting for you. Jack."
I had been in college that Monday, waiting for the day to be over. With an hour left in the day I couldn't wait any longer so I snuck away early. I let myself in to Jack's house and found a note.
"Jess, please make yourself at home. In the spare room you will find an outfit I have selected for you. Put this on. On the dresser is make up and you will find an envelope, read this once you are dressed. Jack."
Reading the note, I felt a surge of excitement. I tried to stay calm, to pour a drink and relax but instead I dropped my bag and sprinted up the stairs and into the spare room. Laying on the bed I saw a satin maid's outfit, black with a white lace apron and white underskirt that flared outwards. It looked incredibly short. Next to the dress lay a pair of black, seamed, fully fitted stockings, a black satin suspender belt, black satin bra, and a tiny black satin gstring. There also lay a hat and a white lace garter to match the outfit.
I caught a glimpse of myself in the mirror as I pulled my long hair free from it's ponytail. My hair looked tired, as did I, and this would not do. I stripped off and gently padded into the bathroom where I showered and washed my hair. I returned to the spare room and gently dried my smooth soft skin. I found a hair dryer in one of the cupboards and sat in front of the mirror, brushing and drying my long dark hair. My skin glowed and my hair shone. Much better, I thought to myself.
I moved to the bed and gently rolled the soft nylon stockings onto my smooth legs. I hooked the satin suspender belt around my waist and carefully attached to clasps to the stockings. Already my smooth cock stood hard, betraying the feminity of my form. My slight frame with gentle curves I worked on with just the right exercise. As I eased the bra straps onto my shoulders I wished for breasts to fill the small satin cups.
I lay back on the bed, waiting for my erection to subside, thinking about anything but the eroticism of my current situation. Eventually it did, and I very carefully stepped into the satin gstring. It felt cool and soft against my cock as I did my best to tuck into the tiny scrap of fabric. My whole body soon felt the cool embrace of satin as I stepped into the maid outfit. It was indeed short, not even reaching my stocking tops. After gently clipping the lace hat into my hair I eased the white garter onto my right thigh and sat in front of the dresser.
I carefully applied make up. I was inexperienced so decided a little would suffice, lipstick and mascara. Once I was satisfied I opened the envelope which sat waiting for me on the dresser. Inside it another note.
"Jess, I hope you like what I have picked for you. I will arrive home at 6pm. You will greet me from the car."
I read that sentence over several times. He wants me to go outside dressed like this? I didn't know what made me more nervous; going outside dressed in women's clothing or going outside dressed in a maids outfit. With the size of the houses in the street and the seclusion of Jack's driveway it was highly unlikely someone could see in from another house but someone walking down the road could easily see down the short driveway. I glanced at the time, he would be home any minute. I just had to do it.
Jack had left a pair of black satin high heels at the foot of the bed which I eased on to my stockinged feet. As I carefully made my way down the stairs I saw Jack's car arrive in the driveway and stop in front of the garage. I looked around and could see no one. I made for the front door and, with my heart pounding, I pulled it open.
The cool afternoon air flooded over me as I carefully walked to the car. I could hear the confident click of my high heels and felt the gentle breeze over my stockinged legs. It was a sensory explosion as I reached out for the handle of Jack's car door and pulled it open. He stepped out in his immaculately tailored suit and nodded to me.
"Good girl", he grinned at me. I felt a surge of excitement at such a greeting. He walked past and towards the house as I closed the car door and followed him. Inside in the hall way he slipped off his suit jacket and hung it up. I stood with my hands clasped in front of me as he walked around me, looking me up and down.
"It suits you," he said as he inspected me, "do you like it?"
"Yes, Sir." I replied. He looked somewhat thoughtful at my response.
"Sir? I like that. I'd also like a drink. Whiskey, rocks."
"Yes, Sir." I turned and walked to the kitchen, Jack following me. As I went to the cupboard for a glass Jack sat at the table, watching me. I searched the freezer for ice unable to resist bending fully at the waist. I knew with the shortness of the dress it would rise up and reveal my pert buttocks, framed perfectly by black suspender straps. Something seemed to have taken over my actions. I felt sexy, feminine, and desirable.
I placed two ice cubes into the glass and turned to Jack. He pointed to a cabinet containing several bottles from which I selected a whisky and poured it for him. I placed the drink in front of him and stood awaiting instructions.
"Fetch my case from the car." Without thinking I returned to Jack's car, finding his case on the passenger seat. As I closed the door to his car I noticed a man stood at the end of the driveway. He was staring at me wide eyed, his dog trying to pull him along the street. I blew him a little kiss as I strode back in to the house. I placed the case next to Jack's feet.
"I think one of your neighbours may have seen me, Sir. He was walking his dog."
"I'm sure you gave him plenty to think about when he gets home." He lent down and retrieved from his case a diary and pen before making a few brief notes. He packed them away before leading me upstairs to his master bedroom.
"Undress me," came his nonchalant instructions. I loosened his tie and unbuttoned his shirt, laying them to one side. Kneeling in front of him now I slipped his shoes and socks from his feet. I gently unbuckled his belt and his trousers before removing them and hanging them up. He wore tight black shorts which bulged with masculinity. Once again kneeling in front of him I hooked my fingers into the waist band and eased them down.
His cock seemed thicker than I remembered it, the hair at the base beautifully trimmed. I stared at it longingly as it hung just a few inches from my face.
"You want to suck it?" Came Jack's voice from above me. I nodded, my eyes fixed on his beautiful cock. Suddenly his hand grabbed the back of my hair pulling it sharply back, he bent down to me, his face inches from mine.
"When I ask a question you will answer it!" his words were filled with anger.
"Yes sir! Yes sir! I'm sorry sir..." His hand slapped me firmly across my face. I was scared and vulnerable.
"Open your mouth!" My face felt hot where I had been struck and he still held my hair. I opened my mouth wide as he ran his free hand over his cock. He held it out to me as it began to harden and I buried it into my mouth. I sucked at him, twisting my tongue over the flared head as he stiffened in my mouth. As my head bobbed back and forth he began to match my movements, thrusting his cock into my mouth. Soon both of his hands were clamped onto my head as he fucked my mouth. I struggled to breathe, his cock forcing me to gag as he forced it into my throat. I fell backwards, gasping for air.
"You're fucking useless!" Jack towered over me, his hard cock standing firm, covered in my saliva, my lipstick smeared along it's length. I pushed my hair away from my face.
"I'm sorry, Sir. Your cock is so big it makes me choke." I hoped I could massage his ego somewhat.
"You will learn!" he told me sternly. "Now bend over the bed."
"Yes sir." I nodded, drawing myself up onto my feet. As I walked to his waist high bed, I saw my reflection. My lipstick smeared, my mascara streaming down my face in long streaks. As I bent at the waist over the side of the bed I could feel how hard my cock had become in my satin panties. As my face touched the cool fabric of the bed I felt Jack's hand strike my exposed arse. Before I could react he struck me again and again.
Whimpering with every strike, I struggled to keep balance on my high heels. Jack was calling out obscenities as he spanked me, calling me a useless cunt, a worthless whore. His punishment subsided and he crawled on to the bed, laying flat on his back.
"Take off your panties," he instructed. I felt drained, my arse felt like it was on fire from repeated spankings. I eased my panties down over my stockings allowing my cock to spring free. I looked to Jack who had smeared lube over his cock and was gently stroking himself.
"Climb on!" he told me, pointing his cock straight up. I climbed onto the bed and straddled him. Reaching behind me I lined up his cock with my tight arse and gently eased it inside of me, stretching to accommodate him. Before long I had built a steady rhythm, his hands on my hips as I bounced happily on top of him.
"Come for me," he ordered. "Come into your hands and eat it!" I pulled the tiny dress high and took hold of my hard cock as it bounced along with me. I was so turned on it only took a few strokes before I felt my cock swell. As I shot my load into my waiting hand I could feel my hole rhythmically twitching around Jack's cock. He fucked me harder as I brought my hand to my lips and as I tasted my own come I felt Jack's cock as he filled my arse with come.
I stayed on top of him, gently enjoying his cock in my arse. His hands ran over my body and my stockinged legs.
"You're a good girl, but you have so much more to learn!"
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<a href="https://www.lushstories.com/stories/crossdressing/learning-to-be-submissive-part-2-1.aspx">Learning To Be Submissive - Part 2</a>