Lily's First LessonbyLily©
Beginning a new job is never easy and my boss, he is the biggest horses’ ass attorney you could ever imagine. He was also one of the best in town and I had been surprised when he called me after I sent him my resume. It had been six months, and I was starting to get used to working for him. He would arrive in the morning, glare at me as he walked into his office, by mid-morning he would ask me into his office to help him find files or instruct me on some new motion. He was a tall intimidating man, not handsome by any stretch of the imagination, he looked dangerous and he was hell as a litigator in the court room. A couple times while I went through his file cabinets looking for some papers he needed I could have sworn he was staring at my ass, and once when I walked by him his hand brushed against my breasts but I decided I was imagining things, after all, I was just an average girl, a little on the plump side, not the kind that would attract a high powered lawyer, and besides I was married with almost grown children so I was sure I was the one imagining things. This didn’t stop me from having a late night fantasy of having him bend me over his desk from time to time, but I was realistic, so when the day came that he yelled “Lily, get in here!” I never imagined what was about to happen.
“Lily, get in here now!” His voice roared at me. I was just getting ready to leave; I set my coat and purse down and walked back into his office.
“Yes Mr. Logan?” I said trying not to let my voice tremble. He stood up and moved towards me file in hand.
“You have been using my computer for personal use.” It was a statement not a question. I must have looked confused, because he shoved the file into my hands,
“Aren’t these yours?” he asked as he walked out of the room. I heard the outer office door lock clicking as I opened the file. Inside were printed copies of all my emails, personal emails, which I had sent privately. I gasped and my entire body began to blush. These were not the kind of emails you wanted your boss to see, or your husband for that matter. They were full of fantasies and personal conversations with other likeminded faceless email friends met in a variety of chat rooms. The safety of the anonymous correspondence made it easy to talk about my deepest desires. I couldn’t bring myself to look at him. I stood with my head bowed, my hands shaking almost dropping the thick folder full of my secrets.
“How did you get these?” I asked, suddenly realizing the ramifications of his discovery.
“I have software that keeps me aware of everything done on MY computers.” He said. I cringed at the anger I heard in his voice.
“What are you going to do?” I asked closing the folder still not able to look at him.
“Look at me.” He demanded. Slowly I lifted my eyes to his. My cheeks burned as I thought of everything he knew about me now.
“Frankly I don’t know what to do with you.” He said glaring at me. “Does your husband know about any of this?” He asked. I shook my head no. “Answer me, Lily.”
”No sir,” I said my voice trembling.
“And do you want to keep it that way?” He asked his eyes watching me closely.
“Oh please, don’t tell him sir.” My eyes pleaded with him not to reveal my secrets. He walked back behind his desk and sat down still staring at me.
“Come here” he said motioning me around his desk. I walked hesitantly towards him; he put his hands on my waist moving me to stand between his legs.
“Is all this stuff true?” He asked me “Or are you just fucking with these guys?” He moved his hands to the desk, resting them on either side of my thighs, effectively trapping me there. I just stood there not saying a word. “Lily?” He asked me again
“Yes, I whispered.” I couldn’t look at him anymore. I knew my cheeks were flaming red and he seemed to be trying to embarrass me even more. I had never felt so vulnerable in my life. I gasped as his hands moved to my hips, and then slowly slid down my thighs; he moved his chair forward as his fingers glided to rest just behind my knees.
“Look at me Lily.” He said and I slowly lifted my head. As his fingers glided up the back of my thighs he stared at me “ You like this don’t you?” he asked, I couldn’t seem to answer “Turn around” He said and I gasped but slowly did as he asked. I felt his hands slide my skirt upward until it barely covered my ass. His big hands moved slowly up the back of my thighs, his fingers pressed against my inner thighs, his blunt finger tips tracing the bottom of each of my cheeks. “Spread your legs Lily.” He said his voice sounded hard, I was so afraid and excited all at once. I moved slightly, “Bend over more” he said putting his hand on my back. One finger pressed against the crotch of my pantyhose, and between my thighs. “This makes you wet?” he asked me as his one finger turned to two rubbing against my sex.
“Yes,” I whimpered trying not to rub back against his fingers.
“Alright Lily, I won’t tell your husband, but you will pay a price.” He whispered.
“What price?” I asked turning my head trying to look at him.
“Whatever I want,” was all he said. He gave my ass a light smack with one hand and pulled my skirt back down, he stood and rubbed himself against my ass as he moved, stopping for a brief moment to rock against my hips. “Don’t wear pantyhose again” he said from behind me.
“Why?” I asked before I thought about it. His fingers yanked up my skirt and ripped away the sheer nylon. His fingers thrust up between my thighs.
“Garters, do you understand?” he growled against my neck.
“Yes sir” I whimpered not able to stop my hips from rocking against him.
“Be ready for your punishment to begin tomorrow.” He said.
I didn’t get much sleep that night. I kissed my husband goodbye and started getting myself ready for work. I imagined all night long what would happen today, what would Mr. Logan do to me? I could not help but remember how his hands felt as they slid up the back of my thighs, I touched myself as I remembered, slipping my fingers in and out and teasing my clit, bringing myself to a quick orgasm in the shower.
When I arrived at the office Mr. Logan was already in his office and virtually ignored me all morning. I began to think everything would be fine, that perhaps he was just trying to scare me; all the same I stayed away from my email account all day. When he finally called me into his office, he was all business asking for a specific file and research material. If his eyes seemed a little hotter than usual I thought it was just my imagination. It didn’t stop me from taking a tiny vibrator into the bathroom and using it until I was breathless.
When I walked back into the office he was waiting for me, leaning against the doorframe glaring at me as I entered the room.
“Where did you go?” He asked staring hard at me.
“I just went to use the bathroom sir.” I said but a blush crept over my face.
“Hmm” he grunted moving to the office door and locking it. “Get in my office now!” He pointed towards the door. I moved towards my desk hoping to hide the vibrator in my purse but he wouldn’t budge, as if he knew what I was up to. His fingers closed around my arm and pulled me into his office. He closed the door and sat down on the high backed couch.
“You don’t seem to have any self control.” He said motioning me to him. I moved to stand near him. He was so quick before I could stop him he had the vibrator out of my pocket and he dangled it in front of me. “You can’t even make it through work without pleasuring yourself?” He asked.
I shook my head. Mr. Logan just stared at me for a minute, he held the vibrator to his nose and I knew he could smell my scent on it. His hand snaked out and grabbed me pulling me forward and across his lap.
“I’m going to have to teach you a lesson.” He said holding me down with one hand I struggled until he leaned over and whispered “Whatever I want remember?”
I quit struggling. His left hand pulled me further over his lap until my plump ass was center stage. The fabric of my skirt was riding up and I could feel cool air on the bottom of my cheeks. He pushed the fabric of my skirt up to my waist. For a moment he said nothing and I wanted to squirm away from him. He held my back firmly and then his right hand traced up the back of my legs and over first one cheek and then the other.
“Are you ready for your lesson?” He asked as his hand rubbed between my thighs.
“Yes sir.” I whispered into the cushion of the couch.
“Your panties are all wet” He said stroking against the crotch. I felt his fingers sliding back and forth just the fabric between my skin and his. “These are in my way,” he said pulling them hard up between the cheeks of my ass. Making me buck against his lap. “I thought I made it clear, not to cover yourself, didn’t I?” He questioned me.
“You said no pantyhose.” I answered daring to sneak a look at him. His eyes were glued to my ass, He turned to look at my face realizing I was staring at him, his hand moved quickly slapping down on my cheeks, the smack echoed through the room.
I gasped and buried my face in the cushions, I heard his chuckle and felt him pull the panties down to my knees and then another smack, I felt my ass heating up; knew there must be a hand print on my pale white skin. He pulled the panties off completely and set them next to my face; I could smell my own arousal and was sure he could also.
“Spread your legs” he said his voice sounding strange. I inched them apart and earned another hard ‘smack’.
My ass jerked at the hard hit, his hands pushed my thighs wider apart and he slapped me again. His fingers moved to my inner thighs and slapped, then again lightly against my already swollen lips
“OHHH” I cried out biting my lips, another smack, and this time harder, directly to my pussy. I wiggled my hips trying to move away but he thrust his hips up, I could feel his hard length pressing against me through his pants, I moaned as his fingers dug into the flesh of my ass, He slid two fingers against my slit and pulled them back soaking wet,
“Damn you get hot easy” he said pushing them deep into me. When he pulled back he pushed me forward and stood quickly unzipping his pants he was on his knees behind me quickly and I felt him slid his cock over my ass, rubbing himself into the crack He pulled me back against him and I felt the head of his dick rubbing against my hole. He pushed in with a hard thrust filling me completely, he was so hard and thick I groaned and tried to move away. He grabbed the discarded vibrator as he pulled away and then slammed back into me.
“I know you like it this way Lily” he said giving my ass another slap.
It made me whimper and push against him. I felt the vibrator on my lips as his dick pushed in and out of me, he slid it back and forth getting wet with my slippery juice. I felt him rub it against my ass.
“OH NO” I cried out jerking away from him, but there was nowhere to go. He let it buzz against my tightest opening and pushed the tip inside me, he leaned forward and bit my shoulder;
“Whatever I want” he said groaning as he slammed his hips into me. He pumped faster, and then reached around to slide a finger over my clit, it made my orgasm begin, as he rubbed my taunt little button he pushed the vibrator into my ass, and turned it on.
My whole body shook as the orgasm took me. I felt his last slam deep inside me as he began to cum. His body jerked forward his cum shooting deep into me spilling down my thighs.
“Don’t move” he said as he pulled his cock from me and leaned back. He turned off the vibrator yet left it buried inside me. He cleaned his dick off and zipped his pants. I started to get up. “I’m not done with you yet” he said I turned to see him smiling at me. I tried to slide my thighs back together but his hand came down on my ass again. “I told you not to move.” He grinned then “Were just getting started.”