I love Casual Fridays at work. It means I get to utilize the full range of my outfits for Jake. Last Friday, I decided to go with a deep V-neck white top, dark blue ruched mini skirt and 3-inch white heels to match.
I love the stares that I get from guys and ladies alike whenever I choose a deep V top to wear to office. The guys are probably imagining what it would feel like have a good squeeze on my breasts. While the ladies probably wish they had such gifts to be squeezed. And then there is another group who will stare with disdain.
But I could not care less what my co-workers think. The most important opinion in the office is Jake’s. After all, he is the Boss.
One of the first things I do every morning is to run through Jake’s schedule with him and see if he needs me do any further prep for his meetings. I usually stand beside him, leaning over his desk. With this white top, he would definitely have full view of my lace bra, which barely supports the weight of my D cups. I could see him salivate over the thought of sliding his big dick in between my tits.
Bent over beside his desk, my bare butt cheeks were partially visible to Jake. I love wearing thongs. It makes me feel extremely sexy. I was wearing a black thong today. Jake noticeably admired my butt while I talked business. I wasn’t sure if what I said was registering with him.
He slid his right hand up my inner thigh. I pretended not to notice. But in truth, I wanted him to go higher. I kept on reading out notes as he stroked my left thigh. With each stroke, he was getting closer to my already wet pussy.
Jake could feel my thighs tensing up. He softly rubbed my wet clit in a circular motion. My knees were weakening but I tried to soldier on this morning’s briefing. I let out a soft moan but Jake smacked my butt playfully and told me to make sure I completed the briefing as he doesn’t want to miss a thing. He went back to rubbing my clit.
I could feel his fingers sliding up and down my slippery slit. I widened my stance to give him full access. He reached under my skirt and cupped my soft butt cheeks and gave them a tight squeeze. My breathing was getting heavier. Jake stuck his finger inside me and started sliding in and out slowly.
“Keep your focus or the punishment is going to be severe”.
My elbows buckled and dropped to his desk as I let out a loud moan. His fingers were rubbing on my g spot. With me bent over, my bare ass was in full view. Jake lifted up my skirt and deftly pulled my g string down my thighs. It quickly dropped to my ankles as he continued to finger fuck me slowly. I stepped out of my panties. The teasing was driving me crazy.
“You are not focusing on your job, Hannah. This is unacceptable. I want to see you after office hours tonight. We will have to talk about the consequences of your performance this morning.”
Jake smacked my ass again and bent down to pick up my black thong. He told me to turn around and made me lick my wet pussy juices off his middle finger.
“Now, go back to work and we will speak tonight. Meanwhile, I will be keeping these.” He waved the thong in my face and put it in his top drawer and closed it shut.
I walked out of his office without any panties. I knew he was still staring at my ass, imagining them naked. I felt my juices streaking down my inner thighs. There is going to be wet pussy stains on my skirt. I wasn’t going to be able to be very mobile at work. I would be left at my desk imagining all the exciting punishment I was about to receive that night. This would only make the stain bigger on my skirt. As I imagined this, I could only smile.
Tonight was going to be a good night.
Jake was out for meetings all day as he left me in office to prep for his pitch this weekend. At about 6.30 pm, he texted me:
“I want you to get ready for your punishment. I will be back in office by 8.”
I had been waiting all day for this. I immediately knew what the text meant. I had to clear his desk, remove my undergarments, get his briefcase of sex toys ready and await his return. Jake was an extremely punctual person. He walked into his office at exactly 8 pm. I stood at attention behind his desk. Everyone had left office as it was a Friday night. He locked the door behind him.
I was extremely nervous for what was about to happen. He directed me to lean over his desk, pressing my breasts against the cold table. My nipples hardened underneath my top. He opened his black briefcase and took out 2 pairs of handcuffs. In a blink of an eye, he cuffed both my wrists on each corner of the desk.
I could hear his footsteps as he walked behind me. My ass was again in full view. Not knowing what he had in store for me was a huge turn-on. I heard him take something else out from the briefcase. He switched a vibrator on and placed the tip right on my protruding clit. The vibration of the cold tip on my slippery pussy was ecstatic. I let out a loud moan as he slid the shaft of the vibrator along my wet slit. I knew I was in for a long night. He was not going to let me have any satisfaction until he had his fun.
Jake loved being in control. He knew how to make me crave his big dick. After bringing me close to orgasm by sliding the vibrator in and out of my vaginal entrance for a good 10 minutes, he suddenly pulled it away, leaving my legs quivering for more. My pussy juices started streaking down my inner thighs again. Without warning, he gave me a loud spank on my right butt cheek. And then another. And another. With each spank, I let out a yelp of pain but it was really turning me on even more. He proceeded to spank the other butt, just as hard.
After that, he continued to toy with me with the vibrator, bringing me close to another orgasm before stopping yet again. I was begging him to fuck me.
“Jake, please make me cum. I want your big fat cock inside me. Fuck me until I cum…”
He responded by spanking my butt as he shoved the entire vibrator inside me. I could feel the rabbit vibrating on my clit, generating intense pleasure all over my body. I was quivering, letting out uncontrollable moans as he slid the vibrator in and out of me. With each stroke, he drove me closer to orgasm and I could feel my bladder swelling up, ready to squirt. My rapid breathing and tense body indicated that I could no longer hold out much longer.
He pulled out the vibrator and and unzipped his pants. I knew his big dick was coming. The anticipation alone was driving me over the edge. With one big stroke of his dick in my pussy, I came hard, squirting my juices on him. He continued to slide his dick in and out of me as my body convulsed on the desk. I could feel my juices flowing down my calf and ankles as he continued to fuck me from behind. I had barely recovered when I felt the swell build up inside me again.
Jake just continued to pound me like an Energizer bunny while I came again. This time, I barely squirted. But my legs were quivering and my knees were giving way. Jake always understood my body and how to use it for his pleasure. He un-cuffed my wrists, as I slumped to the floor.
I turned around to face his monster dick in my face and instinctively took it in my mouth. Being submissive to Jake on my knees was a turn on for me. I sucked on his dick happily, but I could never fit the entire thing inside with my small mouth. He guided my head up and down his dick. I tasted my own cum as I licked his drenched hard-on while sucking on it. I swallowed the mixture of his pre-cum and my juices and the saltiness tasted amazing.
Jake told me to remove my top and I obediently obliged. I knew what he wanted next. He took a seat in his chair and I immediately placed his large manhood in between my breasts. His slippery dick full of my saliva and cum slid easily on my boobs as I pressed them together to stroke it. He finally let out a soft moan of approval. He let me enjoy sliding his dick up and down my tits for a while before he told me to stand up.
He made me remove my skirt and sit on his desk, with my legs spread-eagled. I was completely naked, at his mercy. He grabbed my waist and started fucking my clean-shaven pussy. Jake had masterful control and tremendous stamina. He made me cum another 2 more times while fucking me on his desk without breaking a sweat. I was already feeling weak all over my body.
I begged Jake to finish me off as I had already lost count of how many times I came. He smiled devilishly as he continued to pound my sore pussy. I wrapped my legs and arms around him as he kissed me passionately. Feeling his tongue in my mouth made crave his dick even more.
Jake lifted me off the desk and pressed me against the glass window of his office as he continued to pound my pussy. I was sure my bear ass was in full view if anyone was watching. I could not care less anymore. All I wanted was Jake’s hot cum inside my pussy. Jake was still taking his time pleasuring himself in my hot pussy, but I knew he was getting close as he started to breathe more rapidly.
I whispered in his ear “Jake, I can’t wait to take your cum. I want you to fill my pussy with hot cum…”
This must have put him over the edge. But he dropped me and forced my shoulders down as I got on my knees. He shoved his dick into my mouth and started pushing my head up and down his big dick. This was the first time I felt almost all his dick inside my mouth. I choked on his dick a little, but he did not seem to care. After a few more strokes, I got used to his stride and started sucking his dick every time he thrust it towards my throat. With a few more strokes, he pulled his dick out and let out a loud moan as a huge stream of hot white cum shot onto my face and neck. The remainder of his cum shot on my boobs and started to streak down my body. It was a big mess, but I took it as he had doled out my punishment as promised.
Jake finally looked spent as he got dressed. He handed me a towel to wipe the cum off my body. He told me to get dress without any underwear on.
“You are going home without any of your underwear on tonight. You took your punishment well tonight. But I expect you to bring your A game during our trip this weekend.”
I knew he was alluding to the surprise outfit that I picked for him for the business trip this weekend. I went home and fell asleep almost immediately after taking a quick shower to wash the cum off my hair and face. I hope I don’t wake up late for our flight tomorrow to Singapore.