Mistress Elaina
I met Mistress Elaina, aka Elaine, shortly after getting hired to work at her family's pizza restaurant. I was hired by her mom after a short interview process. It was my first paycheck job! I started out bussing tables, washing dishes and taking out the trash. It was a small restaurant in our tiny town but was always busy. Her mom was strict and there was always something to do. Her dad was the cook, he was nice but very quiet compared to his wife. Elaine was a waitress. She was in her early thirties tall and slender with dirty blonde curly hair and red rimmed glasses. She was married but now divorced. It was rumored she slept around.....I was immediately attracted to her. At work she was just like her mom..... all business. Elaine's younger sister , age mid twenties, also worked as a waitress but was less focused on her work. You wouldn't of known she was Elaine's sister outside the purple rimmed glasses she wore. She was short and slightly pudgy. She was more top heavy compared to Elaine's slender frame. She liked to joke and goof off....which would get me into trouble. She liked flirting with me even though she had a serious boyfriend. I had just moved out for the first time and I mowed lawns on the side. My schedule was perfect, I mowed during the day and worked at the pizza restaurant at night. I had a small one bedroom apartment on the ground level with a small garage. I thought I had it made at just 18 years old...
I worked hard at the restaurant and within a few months I was promoted to cook duties on top of my original duties. Elaine had taken on the managing duties. She liked ordering me around and I was eager to please her. Elaine knew I had a crush on her after I let it slip when talking to her younger sister. I was embarrassed and yet happy she knew. Elaine's sister had mixed feelings since she was slightly smitten with me. One night after closing, I was cleaning in the back while Elaine was going through the receipts for the night. I had always imagined having sex with Elaine in the restaurant over a table and just fucking her as hard as I could. It aroused me. I rubbed myself up against the sink as I washed dishes as quickly as I could. It was late, I was tired and fantasizing when Elaine walked in on me. I shifted away hiding my tiny thick cut hardened cock. Her eyes locked in. She walked up to me and without a word ......grabbed me! I jumped up as she squeezed hard. She had my balls in a strong vice grip. I was in shock and just let her. It hurt and felt good all at once. Elaine then whispers, "are you a good boy?" I didn't know how to answer and remained quiet. She fondled my balls with her thin boney hands.....that were quite strong. The look in her blue eyes was intense. She smirked as she asked if I thought of her as I masturbated. As obvious as it was, I was surprised she knew and muffled out a "uh huh" as a confession.
"Good" she said with a hint of distain. "Go home and masturbate until you have no cum left thinking about me!" She in a sultry hard tone.
I finished cleaning up and raced home. My balls were still throbbing and I jerked off over and over and over. Being 18, I was a cum machine. I shot cum all over my bed, walls, and sheets. When I had finished, my cock was raw and bleeding just under my tip. The next day I awoke hard and sore. That day I opted out of mowing since clothing touching my cock hurt too much. Every time I thought about what Elaine did to me made me erect. I masturbated even if it hurt. I just focused on imagining having sex with Elaine. The following night, Elaine wasn't at the restaurant. I was crushed and moved slowly all night. My energy level was low and her mom noticed. She sent me home after the evening rush fearing I was sick. How right she was but it wasn't that kind of sick. I got to my apartment and noticed Elaine's car parked in my carport spot. I pulled in behind. Elaine wasn't in her car as I walked to my door. My door was partially open as I walked in slowly. Elaine must of heard me and told me to shut the door behind me. She then told me to strip and come into the bedroom. I was elated and quickly kicked off my clothes and walked into the bedroom expecting to see her naked......
My assumption was incorrect but I was still excited to see Elaine wearing short jean cutoffs and a tight pink top with no straps. Her slender tanned shoulders were so sexy and her thin tones legs and painted toes looked sexy. I instinctively covered my short thick cock. Elaine looked me over and said in a flat toned voice...."you must call me Mistress Eliana or just Mistress!" She was serious and as I was about to laugh she kicked me in the balls. She made solid contact and I crumpled to the ground. I gasped, coughed and started tearing up in my eyes. "What's my name!" She shouted. I saw a woman possessed and I was scared. I whimpered a weak and feeble ....
"Mistress Eliana."
Even though I was curled up on the floor. Mistress had manged to slide her foot in on me and applied pressure on my throbbing ball sack. I flinched in pain. She curled her toes down and into me. I just let her. It was an odd sensation of being hurt and totally turned on at the same time. Mistress groped my balls and rubbed her foot onto my cock hard. I was allowed to sit on my knees before her. Mistress didn't want eye contact. I looked downward as she on my bed and rubbed her foot up my chest. I was ordered to suck her toes and did so with pleasure. She forced her toes in my mouth. I licked and sucked as hard as I could. She didn't let me use my hands. She easily pushed me over and stood over me. I looked up between her legs in those short jean cutoffs and could make out she wasn't wearing any underwear. Mistress looked me over and didn't like the little body hair I had. She took me to the shower.
I stood with my hands behind me against the shower wall as Mistress lathered me and the shaved me. Every time I flinched, she gave me a small nick to remind me. Once completely void of body hair, she made me rinse off to show her handy work. Mistress asked for my hand and she yanked me out of the shower and bent me over my sink. She made me spread my legs and then jammed something up my ass. I gush of cool liquid rushed into me. She told me to hold the liquid in as long as I could. Mistress then told me to flush out on the toilet. I held it in until the burning sensation was too much. I quickly sat down and had a ferocious evacuation of the inner contents of my ass. I couldn't help but cry out as the contents oozed out. Mistress had me stand on my quivering legs over the sink as she once again stuck something long up inside my hole. I tightened up my nice hard ass cheeks as she released a soothing oily substance. As hard as I clinched the oil oozed out down my leg. Mistress took me back to my bedroom and had me facing away from her on all fours. Mistress Eliana then slipped out of her shorts, I looked back to view her untanned area. She was perfectly trimmed. Mistress then removed her pink top to reveal her untanned tiny breasts. Her nipples were hard and stuck out like two small pieces of Chicklets gum. I wanted to turn around. Mistress ordered me to look away and it was hard for me not to stare at a goddess. She slapped her hand against my tiny tight ass.....leaving a red mark on my pale skin. I heard the sound of a belt like object. I looked back briefly while she wasn't looking at me and saw this leather like thong she was strapping on. She then attached this long thin jelly cock like object to it. Mistress had me face down into the bed and then reach back opening my cheeks apart. Mistress wasn't patient, Mistress wasn't kind, Mistress buried it deep into my ass. My hands reached back trying to stop. My legs kicked in the startling painful sensation of this object being buried deeply into my ass. Mistress pulled back slowly and buried it deeply again. I cried out. Mistress Eliana talked nonchalantly as she bore down , "I'm preparing you.......you should thank me."
I thanked Mistress Eliana over and over and over...
I worked hard at the restaurant and within a few months I was promoted to cook duties on top of my original duties. Elaine had taken on the managing duties. She liked ordering me around and I was eager to please her. Elaine knew I had a crush on her after I let it slip when talking to her younger sister. I was embarrassed and yet happy she knew. Elaine's sister had mixed feelings since she was slightly smitten with me. One night after closing, I was cleaning in the back while Elaine was going through the receipts for the night. I had always imagined having sex with Elaine in the restaurant over a table and just fucking her as hard as I could. It aroused me. I rubbed myself up against the sink as I washed dishes as quickly as I could. It was late, I was tired and fantasizing when Elaine walked in on me. I shifted away hiding my tiny thick cut hardened cock. Her eyes locked in. She walked up to me and without a word ......grabbed me! I jumped up as she squeezed hard. She had my balls in a strong vice grip. I was in shock and just let her. It hurt and felt good all at once. Elaine then whispers, "are you a good boy?" I didn't know how to answer and remained quiet. She fondled my balls with her thin boney hands.....that were quite strong. The look in her blue eyes was intense. She smirked as she asked if I thought of her as I masturbated. As obvious as it was, I was surprised she knew and muffled out a "uh huh" as a confession.
"Good" she said with a hint of distain. "Go home and masturbate until you have no cum left thinking about me!" She in a sultry hard tone.
I finished cleaning up and raced home. My balls were still throbbing and I jerked off over and over and over. Being 18, I was a cum machine. I shot cum all over my bed, walls, and sheets. When I had finished, my cock was raw and bleeding just under my tip. The next day I awoke hard and sore. That day I opted out of mowing since clothing touching my cock hurt too much. Every time I thought about what Elaine did to me made me erect. I masturbated even if it hurt. I just focused on imagining having sex with Elaine. The following night, Elaine wasn't at the restaurant. I was crushed and moved slowly all night. My energy level was low and her mom noticed. She sent me home after the evening rush fearing I was sick. How right she was but it wasn't that kind of sick. I got to my apartment and noticed Elaine's car parked in my carport spot. I pulled in behind. Elaine wasn't in her car as I walked to my door. My door was partially open as I walked in slowly. Elaine must of heard me and told me to shut the door behind me. She then told me to strip and come into the bedroom. I was elated and quickly kicked off my clothes and walked into the bedroom expecting to see her naked......
My assumption was incorrect but I was still excited to see Elaine wearing short jean cutoffs and a tight pink top with no straps. Her slender tanned shoulders were so sexy and her thin tones legs and painted toes looked sexy. I instinctively covered my short thick cock. Elaine looked me over and said in a flat toned voice...."you must call me Mistress Eliana or just Mistress!" She was serious and as I was about to laugh she kicked me in the balls. She made solid contact and I crumpled to the ground. I gasped, coughed and started tearing up in my eyes. "What's my name!" She shouted. I saw a woman possessed and I was scared. I whimpered a weak and feeble ....
"Mistress Eliana."
Even though I was curled up on the floor. Mistress had manged to slide her foot in on me and applied pressure on my throbbing ball sack. I flinched in pain. She curled her toes down and into me. I just let her. It was an odd sensation of being hurt and totally turned on at the same time. Mistress groped my balls and rubbed her foot onto my cock hard. I was allowed to sit on my knees before her. Mistress didn't want eye contact. I looked downward as she on my bed and rubbed her foot up my chest. I was ordered to suck her toes and did so with pleasure. She forced her toes in my mouth. I licked and sucked as hard as I could. She didn't let me use my hands. She easily pushed me over and stood over me. I looked up between her legs in those short jean cutoffs and could make out she wasn't wearing any underwear. Mistress looked me over and didn't like the little body hair I had. She took me to the shower.
I stood with my hands behind me against the shower wall as Mistress lathered me and the shaved me. Every time I flinched, she gave me a small nick to remind me. Once completely void of body hair, she made me rinse off to show her handy work. Mistress asked for my hand and she yanked me out of the shower and bent me over my sink. She made me spread my legs and then jammed something up my ass. I gush of cool liquid rushed into me. She told me to hold the liquid in as long as I could. Mistress then told me to flush out on the toilet. I held it in until the burning sensation was too much. I quickly sat down and had a ferocious evacuation of the inner contents of my ass. I couldn't help but cry out as the contents oozed out. Mistress had me stand on my quivering legs over the sink as she once again stuck something long up inside my hole. I tightened up my nice hard ass cheeks as she released a soothing oily substance. As hard as I clinched the oil oozed out down my leg. Mistress took me back to my bedroom and had me facing away from her on all fours. Mistress Eliana then slipped out of her shorts, I looked back to view her untanned area. She was perfectly trimmed. Mistress then removed her pink top to reveal her untanned tiny breasts. Her nipples were hard and stuck out like two small pieces of Chicklets gum. I wanted to turn around. Mistress ordered me to look away and it was hard for me not to stare at a goddess. She slapped her hand against my tiny tight ass.....leaving a red mark on my pale skin. I heard the sound of a belt like object. I looked back briefly while she wasn't looking at me and saw this leather like thong she was strapping on. She then attached this long thin jelly cock like object to it. Mistress had me face down into the bed and then reach back opening my cheeks apart. Mistress wasn't patient, Mistress wasn't kind, Mistress buried it deep into my ass. My hands reached back trying to stop. My legs kicked in the startling painful sensation of this object being buried deeply into my ass. Mistress pulled back slowly and buried it deeply again. I cried out. Mistress Eliana talked nonchalantly as she bore down , "I'm preparing you.......you should thank me."
I thanked Mistress Eliana over and over and over...
1 year ago
