The only good things about these trips usually meant I ate good and had a few drinks on the ole expense account, but this time was different. I had to miss the normally scheduled class and attend the make-up date. This meant there were less people from my company attending, in fact there was only one other person going, and that person was the smoking hot, younger lady that also worked in my department.
Even though I am technically her bosses’ boss and ten years older than her (I am 40, she is 30), I constantly catch myself staring at her when she walks by. Thinking about what that body must look like underneath her uniform. Even though the uniforms required are by no means flattering to anyone, she fills hers out nicely.
The first day of our training we sat beside each other in class and flirted back and forth throughout the day. I noticed a real difference in her demeanor around me outside of the workplace. Normally she was reserved and quiet, but today she was a totally different person. My perverted mind kept thinking of all the bad things I wanted to do this girl!
After the first day of class, we checked into a nearby hotel (separate rooms of course). As we were walking to the elevator, I asked her if she was hungry. She stated that she wasn’t all that hungry, but was interested in having a few drinks at the bar we saw across the street as we were pulling in. As we were finding our rooms, I told her to get freshened up and we would meet in the lobby in about a couple hours.
My mind was racing…was this happening? Did she really want to have drinks with me, or just have drinks? She was definitely flirting today….Oh, wow! This might turn out good….
An hour later, after a quick workout in the hotel gym, a shower, and fresh change of clothes, I stroll into the lobby. I look around and find her sitting on the couch thumbing through her phone. My mouth about dropped. I’m sure I stood there staring for much longer than I should. She had changed into a tight sweater dress that was way too short and hugged her curves in all the right spots. She looked up at me, bit her lower lip and then smiled back at me. I asked if she was ready for a drink and she told me to lead the way.
The bar was not very crowded, but they had a pretty decent band. We talked a lot, we drank a lot! When the band would play a song she liked, she would get up and dance. The girl could move! I loved watching her, whether she was sitting across from me or if she was dancing. She was beautiful.
Even though we were having fun, I suggested we try the hotel bar and see what they had to offer. I paid our tab and we headed for the door. When we opened the door the wind nearly knocked us down. A storm was coming and it was cold! We hurried back to the hotel and found the hotel bar. I ordered another beer for us, but she told the bartender to bring us Fireball shots. The girl was bound and determined to get us drunk. Several more beers and fireballs later, we heard last call.
At this point she is quite drunk and I’m pretty well on my way. As we get into the elevator, I notice a look on her face. She is looking directly at me, with a "I want you" look and biting her lip. The elevator stops and she stumbles into me. I catch her and we both laugh and stare into each other’s eyes for too long. We are both married…I stand her back up and we both laugh.
Our rooms are directly across from each other. God, I want to fuck this woman, but… at this point, I have conceded that this is the end of the night for us. I find my room key and unlock my door; she is still fumbling through her purse looking for hers. I am about to ask if I can help when she says "fuck, I gotta pee!" and barges across the hall, through my open door and into my bathroom. She doesn’t even close the door. In order to seem somewhat gentlemanly, I move away from the open door and let her have her pee in peace.
Once she is done peeing, she comes out of the bathroom, plops face down across my king sized bed and says "I can’t find my fucking key"
Well that’s the way I ended up here…staring at my younger, married, smoking hot, coworker, sprawled out across my bed. Her dress never got straightened back out after her emergency pee break, so it is riding all the way up half past her ass. She’s not wearing panties! Oh fuck! God she looks good laying there. As I am moving to grab her purse off the floor to help her find her key, she spreads her legs even more, pooches her ass up a little and gives me a perfect view of her shaved, puffy little pussy.
Okay! I’m thinking, that had to be on purpose! Well I’m just drunk enough to see if that is true.
I move around to the side of the bed and swat her ass hard with my bare hand as I proceed to tell her that "bad things are going to happen if she doesn’t cover that thing up!" She let out a little yelp, looks back at me, bites her lip, reaches down and slides her dress up a little more so now her ass is fully exposed, and says, "Well, maybe I like bad things…plus I’ve been a bad girl"
My cock had been three quarters hard all day being around this woman, now it was as hard it has been in years! This girl had been teasing me all day, now she is lying half exposed and asking for a spanking!
"How bad have you been" I ask.
"Very" she says.
"And what have you done that’s so bad?" I reply.
"Hmmm," she says, "I teased you all day, I fantasized about you having your way with me, and I actually had to go to the bathroom in the hotel bar to masturbate so I wouldn’t jump you right there on the bar!"
I ask, "What do you think your punishment should be for being so bad today?"
She simply replied, "You are in charge, you should do whatever you think I deserve."
"Well, little girls who have been bad need to be spanked so they know how to act. Do you agree?
"Yes Sir! I believe I need a good spanking" she stated while biting her lip.
I sat down on the edge of the bed and ordered her to get across my lap. She practically jumped into position, giggling all the way. As she got into position I could feel her big 36D tits slide across my crotch, sending a tingle down my throbbing cock. She wiggled and wiggled, pulled her dress back up and exposed that glorious ass to me once more.
"What is so funny" I asked as my right hand smacked her ass again.
"Nothing sir." As she let out another giggle and immediately covered her mouth to keep from laughing out loud.
I smacked her left cheek, then the right, back and forth for several blows. At this point she still was giggling every time I would smack her ass. She was even poking her ass up higher for me to have a better target. Now I wasn’t being extremely rough, but was smacking her hard enough the giggling should have ceased somewhat. That’s when I decided, I needed to change this up a little as I spied her wooden hairbrush laying in the jumbled contents of her purse.
"Where are your panties?" I asked.
Sheepishly she said, looking back over her shoulder at me "I stuffed them in her purse after I soaked them playing with myself in the bathroom."
With that I parted her legs and ran my hand down her crack. I could immediately feel the heat from her pussy. I buried two fingers knuckle deep into her. She was so wet my fingers slid right in.
As I was finger fucking her, she began to push back on my fingers, grinding herself into them. The giggling had stopped and now soft moans were coming forth. My other two free fingers found her clit and started to rub it. I could tell she was getting close to an orgasm by her breathing and grinding. I pulled my fingers out of her and slapped her ass hard again.
She said’ "No, don’t stop!"
"You are supposed to be getting punished, but you are enjoying this far too much for it to be a punishment!" I stated sternly "But you will get rewarded once you have learned your lesson"
With her still across my lap, I leaned over and dumped her purse out on the floor and found her panties, her hairbrush, and a vibrator.
"Well, Well, Well! What do we have here" I said.
For the first time today I saw her blush…I picked up her panties and smelled them. Yum, I thought, but immediately told her to open her mouth. She opened her mouth and I pushed her lace panties into her mouth and ordered her to assume the position again. I reached down and grabbed the hairbrush off the floor and popped my open hand a couple times to get a feel for it. The giggling had stopped, the wiggling had stopped, now she lay perfectly still across my lap. I could feel the concern in her body. I tapped her butt a couple times with the brush; she complied by raising her ass higher.
Whack, Whack…Whack, Whack…Left Cheek, Right Cheek …Left Cheek, Right Cheek
She gasps, but held her position.
"Did you use your vibrator today when you had to relieve yourself?"
"Yes sir" Pulling her panties out her mouth long enough to answer then putting them back.
Whack, Whack…Whack, Whack…Left Cheek, Right Cheek …Left Cheek, Right Cheek
"What were you thinking about?"
"You pounding me with your hard cock"
Whack, Whack…Whack, Whack…Left Cheek, Right Cheek …Left Cheek, Right Cheek…
"Have you fantasized about that before today?"
Whack, Whack…"Answer me"
"Yes sir"
Whack, Whack…Whack, Whack…Left Cheek, Right Cheek …Left Cheek, Right Cheek…Her pale skin on her ass was now glowing in pink and red.
"Well, once I am through punishing you, I am going to live out a few of my own fantasies on you. Do you think you have learned your lesson yet?"
"No Sir" was all she said as she pushed her ass back up in the air.
I slid my hand back between her legs to feel her pussy once more. It was hotter and wetter than before. She was literally dripping.
"This is going to be hard and fast…You better hold on" as I removed my hand from her crotch and popped her ass again.
Whack, Whack, Whack, Whack, Whack….
Her fingers tightly gripping the bed covers and gasps escaping with each blow.
Whack Whack, Whack Whack, Whack Whack, Whack Whack, Whack, Whack….
Her body starts shaking and the gasps turn into yelps as I reach down and stuff the panties back into her now open mouth.
Whack Whack, Whack Whack, Whack Whack, Whack Whack, Whack, Whack, Whack Whack…
"Are you ready to be a good girl?"
"Maybe…" she sniffled as she removed the panties from her mouth once more.
Whack Whack, Whack Whack, Whack Whack, Whack Whack, Whack, Whack, Whack Whack…
"Okay! Okay! I’ll be good!" As she covers her ass with her hands and begins rubbing her bright red ass cheeks.
"Good, now get up and take off all your clothes and lay back down!"
She gets up still rubbing her ass and pulls her dress up and over her head. I see her perfectly shaved pussy and get another eyeful as she undoes her bra and lets it drop to the floor. Her tits are just as gorgeous as her ass!
I stand up behind her and push her face down into the bed. I grab the vibrator she had in her purse and hand it to her.
"You are now going to show me how you came today while you were thinking about me ramming your cunt."
"You’re a dirty old man," she said "I like that!"
She rose up on her knees with a perfectly arched back and raised the vibrator between her legs. The site was amazing and I had a perfect view to watch. Her twat was swollen and dripping her juices on the bed as the vibrator made passes over her clit, up and down her lips, and then deep inside before repeating the cycle. My cock was about to explode just watching. There was no way I could fuck her now….It would be over before it got it all the way in.
I positioned myself directly behind her, spread her ass cheeks and watched the show for a moment, and then I buried my tongue as deep as I could go straight in her little tight asshole. That did it! She began screaming, tensed up and then full release. Her orgasm rocked through her entire body. As she orgasmed, she began to fall forward, but I pinned her down and began lapping her pussy from behind as each contraction hit. I could feel her pussy muscles contracting on my tongue with each orgasmic wave.
"Oh My God!….Oh My God!" was all she could say as she rolled over onto her back.
I never really let her come down off her high as I stripped my clothes and for the first time she could see my manhood. My 8" cock was as hard as it has ever been and standing straight out. My balls felt like I’ve needed to come for hours.
I quickly straddled her across her stomach and began tapping my dick on her tits. She reached for my dick and pulled me to her mouth. She sucked on the head for a minute and squeezed my balls before attempting to take all of me into her mouth. Her mouth felt so good, I knew I wouldn’t last long.
As she was sucking I reached back between her legs and began to finger her clit again. With this she began to suck harder as she bucked her hips into my fingers. I was about to blow, so I pulled out of her mouth. My dick was now coated with her saliva, so I positioned myself back between those glorious tits and began to hump them. She squeezed them together as I humped harder and harder. Her eyes were staring directly into mine as I pounded her tits and fingered her pussy. I had three fingers buried into her and she was bucking so hard it was hard to keep rhythm on my tit fuck.
Her orgasm hit hard again! Her eyes rolled back, her legs clamped down hard on my fingers and she continued bucking her hips. The quivering of her pussy could be felt all the way up her body.
"Oh My God!….Oh My God! I’m fucking cumming again!"
Seeing and feeling her climax was too much! My dick and balls could not hold back any more. I freed my hand from its pussy death grip and concentrated on fucking those tits. I felt the rumble, as five ropes of cum jetted out of my pulsating dick. The first load hit her right in the face, the second under her chin. She grabbed my cock as it was cumming and stroked it feverously as she pulled it to her mouth, where I deposited the last three jets.
With a big smile and never taking her eyes off mine, she swallowed every drop of my semen while slowly continuing to stroke me off. Her free hand began cleaning the rampart cum off her chin and face and licking her fingers clean.
This had been great, but I was nowhere finished with this girl. I slid down her body, stopping to suck and squeeze on both tits. For a thirty year old her tits were still very firm and not saggy at all. I kind of thought from the way she looked in clothes that they were fake, but these were definitely real. They were big and round with medium sized nipples. As I sucked and squeezed, she wrapped her legs around me and started grinding her hips against me.
"I guess you’re not done," she said between moans.
"I think you still need to have a few more orgasms before I am satisfied" I replied.
"Oh my God! I’ve already had at least 4 today…I get more?" was her reply.
"Four? I only know of three…"
"Well, I just had one on your fingers, I had one while I was using my vibrator for you, the third was my with my vibrator in the bathroom earlier, and kinda had one while you were spanking me"
"Really? You are a bad girl" I stated. "Shall I continue?"
With a gleam in her eye she simply stated "Yes Sir" as she leaned back and grabbed the back of my head and pushed me downward.
I eased down and positioned myself between her legs. She was perfectly shaved, actually It looked and felt more like a very recent waxing. Her lips were swollen and pink; her sex was already half open to me as I breathed in her aroma. I began softly. Licking her from the bottom of the opening to the top and repeating. Her juices flowed instantly. Slowly I began plunging deeper and deeper into her hole as I made passes. Two fingers made their way into her pussy. I was stoking her G spot and licking her clit at this point.
Her bucking hips and increasing moans told me to keep up what I was doing. My dick was beginning to recover as I could feel it start to stiffen. I worked her like this for several minutes. She was fucking my face and fingers as much as I was her. Soon I felt her body start to tighten up, her orgasm was close. At this point I held my head and fingers still. My tongue firmly placed on her swollen clit, my fingers buried deep. With this new placement she grabbed the back of my head and was grinding hard into both of them.
Then a loud cry "Oh my God… Oh my God… Oh my God…"
Her pussy practically exploded in mouth and all over my face. She was a squirter! I pressed harder with my tongue, but removed my fingers from her pussy so I could freely lap up all of her orgasmic flow. Her orgasm continued for several seconds as she bucked and shrieked.
Soon the waves stopped and she went limp. However, there was no way I was done. I slowly started the process all over. My tongue cleaning around all of her pussy and softly caressing her swollen hard clit with each pass.
As I looked up, she was fondling her boobs and lightly pinching her nipples. Her hips began to slowly rise to meet my face with each stroke. Her pussy was wide open inviting me to continue my exploration.
I grabbed her calves and pushed her legs back and open to get better access and continued my assault. From this new position I had access to both her pussy and her ass. I plunged my tongue into her pussy while pinning her legs back. From there I eased my tongue down to her puckering little asshole. After a couple flickering passes I commenced to tongue fucking her ass.
Her right hand left her boobs and went directly to her clit. While I was eating her ass, her fingers worked her engorged bud into a frenzy. I could tell the next one was close now.
"Oh Fuck!" she screamed as her body started tensing up once again. The convulsions ripped through her body once more as her climax took her away. "Oh Fuck…Oh fuck…Oh fuck!" was all I could hear.
Her orgasm started to die down and I removed my tongue from her ass. With her legs still pinned back I had a perfect view of her pussy. It was still pulsating open and closed with her sweat cream oozing out with each pulse. That was one happy looking pussy! But now I was ready again.
With her legs still pinned back, I positioned myself for entry. My dick was as hard as was before, but I knew now I could last long enough to give her a proper fucking. She gasped as my big cock head broke the barrier and I eased into her. I pushed until I was balls deep. She was already completely lubricated, but I pulled almost all the way out and eased all the way in three or four times to let her adjust to me. I let go of her legs and put one each on my shoulder and began to find a rhythm. I grabbed her hips and pulled her into me with each thrust. She was getting into it too. Our bodies were slapping together in perfect time. My balls would slap her asshole with each thrust, her boobs bounced with each impact. She moved one of her legs off my shoulder and put her foot on my chest. I grabbed and stuck her big toe in my mouth and started sucking it.
"Oh fuck…Oh my God!...I’m coming again!" she squelled.
I never slowed the assault, in fact I crashed even harder into with each thrust. I fucked her hard through her orgasm. She gripped the covers, as her body convulsed. Her leg was shaking and her breathing heavy as she came down.
I let go of her legs and lowered myself into more of a missionary position with me still inside her. Our eyes met and we kissed for the first time; long and deep kisses, passionate kisses. Although I was still inside her, I wasn’t really thrusting. Soon, during our kissing, I pushed as deep as I could go and held myself there. She took over from there by grinding her throbbing pussy into my rod. After a minute or so of this another round of climax hit her. I could feel every muscle in her body tense up, then a rapid succession on contractions from her sex. I could feel each time it would squeeze and release me. We were staring each other in the eyes as she orgasmed, which was a beautiful sight in itself.
As soon as that orgasm passed I picked up the pace, humping her almost limp body now. I reached down and grabbed both ass cheeks and squeezed as I began pounding her sex with my dick.
I am gripping her butt and every now and then tease her asshole with my fingers when she says, "stick your finger in my ass."
With that, I proceed to slide my index finger in her ass all the way to knuckle. It had no more gotten all the way in when she started cumming again. I pushed in deep with both finger and dick and rode her wave of pleasure as she bucked under me. This girl was definitely multi-orgasmic!
"Oh, my God! How many was that?" she said.
"I don’t know, but we still ain’t done." I replied. "Now roll over!"
I eased off her and popped her on the butt as she flipped over. She put her face in the pillows and stuck her ass up in the air for me.
I repositioned myself behind her and inserted my cock. I grabbed her hips and started moving in and out.
"Oh, fuck that’s deep!" she said, as began fucking her harder and harder. With each thrust, her ass cheeks would compress and send out ripples of soft flesh toward her back. Soon, she was backing into my thrusts, fucking me back as I assaulted her from behind. My balls were slamming into her clit each time we crashed together.
I reached down and grabbed her shoulders to pull her even harder into me as we fucked. I was fucking this woman with everything I had. Moans and grunts and heaving breathing were coming from both of us. Sweat now pouring from both of us. It was animalistic fucking. It was raw. It was awesome.
"Oh, God! Oh, God! Oh, God! I’m gonna…." Was all she got out before her pussy exploded for the second time. I’m not talking a little squirt. This squirt was an eruption. It felt like someone took a bucket of hot water and threw it on me. Both her legs began quivering then turned into full on shaking as she collapsed forward.
Well, I hadn’t come yet, so I chased her straight down. With her lying flat of her stomach, I positioned myself on top of her and slid my dick right back in its rightful place. Her pussy was wore out by now, but I had to get my nut so I put it right back in and continued the pummeling. One hand was on her shoulder pushing her down, the other cupped under her pelvis pulling her into my thrusts.
I continued fucking her hard. She had practically gone limp. I fucked and fucked until I felt the boiling in my balls. As my release began, I lightly bit her on the shoulder. My dick began pulsing as it released my cum. Wave after wave of pure bliss ripping through me. I was almost thru when she started her final climax of the night. Her quivering pussy milking the last of my semen from my shaft.
We both collapsed in a tangled pile of sweat and other body fluids. Neither of us said a word as we passed out.
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