Casual Friday

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.

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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.

 

Mixing Pleasure with Business…

I have been excited all week ever since Jake (my boss) informed me that I will be traveling with him on a business trip this weekend. We are going to Singapore for a bunch of meetings. As his personal aide, I am needed to be by his side almost always. Traveling with him has always been eventful.

First and foremost, let me introduce the Boss. He is a young (mid-30s) CEO of a start-up company that I work in. A very ambitious and sort of workaholic person. But he plays almost as hard as he works. To maintain his energy level throughout his busy days, he naturally keeps a healthy body. He is not buffed like a gym rat, but he is noticeably fit and has a 6-pack, with very toned muscles. Needless to say, a hot and successful businessman makes my pussy juices flow. It was one of the reasons I decided to work for him as his personal aide. Apart from wanting to work in an energetic start-up environment full of young ambitious people, of course.

In our last trip to Singapore, we had more than our fair share of excitement. During these business trips, we usually had some down time in the evenings and I bought a new set of bikini just for Jake’s viewing pleasure.

After a full day of challenging business meetings, I told Jake that I needed to release some stress and will go chill in the private jacuzzi at our suite. Even though I usually booked 2 rooms for our travels to avoid suspicion, Jake always insisted that I stay in his room with him. I invited him to join me in the jacuzzi but he said he had to reply to a bunch of emails and may join me later. I went to the room and put on my new pair of bikinis and stopped by his work table to give him a peck on the cheek and asked if he was sure if he didn’t want to join me.

He resisted, but I could see the growing bulge in his pants as he stared down my cleavage. I quickly left him wanting more and headed out to the patio. I sat there in the warm bath for a good 15 minutes before Jake came outside in his briefs. I could see his 8-inch dick tenting up his pants. Knowing that he must have been imagining me in my bikini made me horny. Before he stepped into the jacuzzi to join me, he pulled down his briefs and his thick hard dick sprung into view.

I love the view of his clean shaven pubic area. It made his dick look like a monster. Imagining the big hard dick sliding in and out of my pussy makes me dizzy. He quickly slid into the warm water right beside me. Before I could open my mouth to say anything, he put his index finger to my lips and said that we have done enough talking for the day during our meetings. No more talking. I could see he could not wait to tear the bikini off my D-cups. He leaned in and started kissing me roughly, just the way I like it. I like a man who knows what he wants and isn’t shy to take it.

I climbed on top of his lap to get into a more comfortable position. He grabbed my ass with both his hands and pulled me close to him. My breasts were firmly pressed against his muscular chest as we continued to kiss passionately. Jake moved his palms to my breasts and gave them a good tight squeeze. I let out a loud moan as my breathing became faster. I could feel his erect dick pressing against my pussy through my bikini bottom. I slide my body up and down, rubbing the tip of his penis, teasing him. His eyes showed that he could not wait to fuck me.

He pulled off the string of my bikini top and started sucking on my hard nipples. I leaned back to give him full access and happily lapped up both my breasts with his well-trained tongue. I could not hold back my loud moans. I whispered into his ear “I want you to fuck me from behind, hard…”

Jake doesn’t need me to ask twice. He grabbed on my ass and told me to hang on. He lifted me out of the jacuzzi and carried me towards the bedroom as we continued to kiss. I was impressed by how strong he was, but this was not unexpected. He threw me onto the bed and jumped on top of me. He continued to suck on my nipples as he pinned my wrists down. I love a man who wants to be in control. He continued to lick downwards and proceeded to slide my bikini bottom down towards my ankles.

I kicked the bottom off and he immediately spread my thighs wide open. My clean shaved pussy was at his mercy. I was visibly wet and he continued to use his masterful tongue to pleasure all my sensitive areas. He nibbled a little at my inner thighs before diving into my clit. I don’t even know what technique he was using, but his continuous licking and sucking was making me scream.

“Jake, stop toying with me and fuck me”. He continued to impress me with his strength as he easily flipped me over my tummy. He grabbed my waist and pulled my ass up as he positioned his dick right at the entrance of my pussy.

“You sure you can handle this, you little whore?” he said as he stroked the tip of his penis up and down my pussy lips.

In the midst of my moaning, I could not even muster an answer before he shoved all 8 inches of his dick inside my tight pussy. Luckily I was wet enough, or else I was sure that monster dick was going to tear something. Jake started pounding on my pussy. I was right. He could no longer wait to fuck me. I could hear my pussy juices squishing as he slid his dick in and out of me. His rhythmic pounding was just the right pace. He made it clear he was in no rush to cum. But I could not hold out much longer as my body convulsed uncontrollably while I came.

He turned me over and lifted me on to his lap and started fucking me cowgirl style. I wrapped my arms around him, almost as if holding for dear life. He guided my ass and hips as I rode up and down his rock hard cock.

Jake was a real master at pleasuring all my right spots. I could feel his tongue on my breasts while his dick was rubbing on my g-spot. He had made me squirt once before, but it rarely happens. This time, I could feel my tension building up in my bladder. I knew I was going to squirt if he kept this up.

I was growing increasingly louder and this made Jake quicken his pace. He was moaning louder too. I felt his body tense up and he let out a loud moan before he shot his load inside my pussy. After a few more strokes, I felt my pussy juices squirt out all over his lap as I had my second orgasm that night.

I almost passed out from the giddiness of this amazing session. But we were late for our dinner reservation. As I got up to clean up, he gave a big smack on my bare ass and said, “This isn’t over”.

I quickly put on a tight bodycon dress without wearing any bra and panties for dinner. Jake didn’t comment on my dress, but he smiled as he approved the hard nipples visible through my black dress. After our dinner, we went back up to his room and had a glass of wine. The combination of the smell of sex that we had that evening and the wine made me horny again. We continued our hardcore fucking and Jake came 2 more times while I had 3 more orgasms that night.

That was our last business trip together a month ago. I can’t wait to see what he has in store. He gave me RM500 allowance and told me to surprise him with an outfit for this weekend. I packed a little something something for the trip to surprise Boss. But more on this next week!

My “first” time…

The first 17 years of my life was a very protected one. My typically Asian parents were strict and demanding. But all teenage girls rebel one way or another and do things that they probably would regret some day behind their parents’ backs.

I was no different. Even as early as 14, I knew I was a very sexual person. I studied in a co-ed school somewhere in Klang Valley (in Malaysia). If you didn’t want boys and girls to do any dirty deeds, you should never put them in the same school. My first sexual encounter was with 17 year-old boy. I was only in Form 2, but I was blessed to have developed early. Even at 14, I was a petite girl with big C cups.

This “gift” bestowed upon me attention that became the envy of even the older girls at school. Being an over-protected only child, I was told to stay away from bad boys. Perhaps, through the constant brain-washing by my parents, I had a strong affinity for nerdy guys. Not those with thick glasses, but the quiet and studious ones who sat in the corner of the classroom mysteriously, occasionally throwing over an innocent glance.

I will call this hot geek Adam. I first saw him sitting at the back of his classroom, doodling under his desk, while the loud boys were being their rowdy selves in front of the classroom in the absence of their teacher. There was something about Adam that sent slight tingling sensations to my nether regions. I was walking with my girl friends along the corridor, staring at him as we walked by, when all of a sudden, he looked up directly at me. My heart raced as I panicked, but he smiled faintly before he looked back down and continued his doodling. Adam was my first crush.

About a week later, I was sitting alone in the waiting area for my parents to pick me up from school. My mom was always late. Usually, I was one of the last few people to leave the school. As luck would have it, Adam walked by and he gave me that sweet smile again. I mustered up whatever meekness I had to give a weak wave of my right hand. Adam was walking over!

“Hi, you must be Hannah. I saw you with the bunch of popular girls from Form 2A the other day. I am Adam”.

“Oh, hehe… Nice to meet you…” I could only blush. I didn’t know his name, but he knew mine. How?

“Are you waiting for your parents?”. He struggled with small talk. That made him so much more adorable.

After some further un-memorable small talk, he plonked his ass down beside me on the bench and decided to wait with me. It was not a warm day, but I could feel my sweaty palms and face. I could barely hear Adam over my own loud inner monologues. All I remembered was, he said, “Let’s have lunch at McDonald’s tomorrow.” just before my mom drove in. It was a date!

Being the shy geek that he is, Adam was no casanova when it came to dates. Despite his fumbling, I could notice sheer intelligence. And he was funny in a cute way. I liked that he was laid back and did not come with the ego of a football jock. I found out that Adam lived with his single mom who was out philandering with rich unwanted husbands. But his dad left him a sizable inheritance and a used Honda that he drives himself with.

But with his shy demeanor, I quickly realized that I had to be the first to make the move. I gave some lame excuse that I was feeling a little cold and asked if he could lend me his warm hands. I was 14, and that was the extent of my repertoire.

Adam willingly obliged and we held hands for the first time. After staring at each other for a couple of minutes, playing with each others fingers, I broke the silence. “Is there anything else you would like to do?”. He innocently said that normally, he will head home after school and watch some DVDs. I hurriedly seized the opportunity and invited myself to watch a movie with him. This was an era before “Netflix and chill…”.

He asked me to pick a movie and I naughtily chose “The Girl Next Door” and plopped myself on his right. I never intended to watch the movie anyway. Just minutes into the movie, I let my right hand slide sensually from his knees all the way up towards his crotch. We were both still in our school uniforms. He was a prefect, so he was wearing white pants with a white buttoned on shirt (as is the norm in Malaysia). I could feel his heart beating faster as I got closer to his dick.

He turned towards me and grabbed me face in with his palms and started kissing me passionately. I started rubbing my right hand up and down his growing dick. I could sense he was going to be big (for an Asian). I climbed on his lap and straddled him with my lips still locked on his. He was an excellent kisser. I unbuckled his belt and unzipped his pants. He returned the favor by unzipping my light blue pinafore pulled it over my head, leaving me with only my translucent white blouse and light blue cotton panties.

He admired my 30C-sized breasts, slightly masked by the see through white blouse and matching light blue bra. He deftly unbuttoned my blouse and revealed my lace bra. Adam got right down to business as he licked my cleavage. He slipped my bra strap down my shoulders and started sucking on my already-hard nipples.

My breathing quickened and I started moaning softly. While I was still shy as it was my first experience, I was quickly losing my inhibitions. He alternated between licking and sucking on my nipples, which drove me crazy. I could feel my wetness on my panties. I pulled away momentarily and slid down the sofa pulling down his pants while getting down on my knees. I also pulled down his briefs to reveal his 7-inch hard-on.

He was not shaved, but his dick still looked really big in my small hands. I started stroking his shaft up and down while wrapping my hands around it tightly. Then I lowered my head onto the tip of his dick and started licking the sensitive area under his tip. He groaned loudly, which I took to be a sign of approval. I was trying to emulate whatever technique I had learnt from watching pornos and it seemed to be working very well.

After 10 minutes of sliding my hands up and down his hard dick while sucking on the tip, I could feel his entire body getting tense. I knew he was getting close. I decided to try to take as much of his dick into my mouth. I could get at most 3-4 inches in and I just slid my mouth in and out of his dick while sucking hard on it.

He instinctively grabbed my long hair with his right hand and just guided my head up and down his groin area. His dick was getting slippery with the mixture of my saliva and his pre-cum dripping down his shaft. He moaned that he was getting very close to cumming. Knowing that he was enjoying my blowjob skills turned me on even more. I quickened my pace, sliding his dick in and out of my mouth even faster while stroking the base.

I could sense that he was trying to catch his breath as he moaned out “I am coming, Hannah. You’re gonna make me cum….” He proceeded to shoot a big load towards my throat. The force of his cum surprised me and I pulled his dick out of my mouth. He continued cumming, his semen landing on my cheek and neck.

He just leaned back and exhaled with great pleasure. I was feeling so horny, with my panties dripping wet. I noticed Adam was clearly too exhausted to return the favor. I reached into my panties and started rubbing my clit. I was slippery wet. Watching his dick still throbbing hard after ejaculation made me even hornier. After a few more minutes of rubbing on my clit, I felt my entire body tense up and had one of the best orgasms I have had up until that point in my life. I climbed back up on the sofa, wiped my face with some tissue from the coffee table and laid across his lap and soon fell asleep half naked.

By the time I woke up, he was already dressed and had put a small blanket over me. It was very sweet. I stood up and kissed him. It was a long kiss and I was starting to feel myself getting turned on again. But I had to go home as I am sure my mom would get on my case if I was too late.

After dinner at home, I replayed the entire episode in my head in the privacy of my bedroom and masturbated to orgasm one more time before falling asleep. This was an exciting beginning to my sexual adventures. Before this, I was always nervous about sex. Crossing this first threshold with Adam made me more daring, which was somehow liberating. I felt more confident to try out more things and eventually lost my virginity to Adam. But that is a story for another day.