The Encounter 2
Erotic Couplings Story

The Encounter 2

by Mayihaveanother 18 min read 0.0 (0 views)
wet pussy beautiful tits hard coc tight ass female boss boss worplace
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Thank you for taking the time to read my continued story. Your comments, suggestions, & recommendations are Very much appreciated!

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Is this damned workshop ever going to end for the day? I'd been to so many workshops like this in my 7 years with Hutton & Frank. I could teach this stuff for goodness sake!

The utterly amazing first night Encounter with Susan and Ben had been the best possible way to start this weekend training workshop, but I was growing more and more impatient to get out of my boss's clutches and up to my shower. Big plans awaited with my two hot new friends!

"What's your evening look like Caleb?"

My boss, Diane, had followed me to the coffee concession at the back of the ballroom where our workshop was being held. She wasn't a horrible boss by any measure. More than a little stiff and formal most of the time, but not breathing down everyone's neck all the time either, like some of the managers in the Company. She was nice enough looking, kinda pretty actually, but soooo stiff! As usual, she was dressed in a very conservative professional way... her 'uniform'. Slacks that never seemed to have a wrinkle, plain white blouse, no frills, covered by her matching vest and suit coat. Crisp and clean and ALWAYS professional! She had a decent figure as far as I could tell under all that crisp and clean, but some of my co-workers had decided Diane was privately a raging lesbian and that's why we NEVER saw her in a dress... dyke for sure! But, right now, all I knew was that I was cornered with no easy escape.

Panic gripped me! It certainly was sounding like Diane might be about to plan my evening for me and there's no way I could let that happen! Horse cock, Ben by name, and Sweet Pussy, Susan, had agreed that a Round Two rematch was definitely in order, and there's no way I wanted to miss out on that. We'd had too much fun together and I was determined to not miss 'The Sequel'!!

Susan lives in Seattle, so we'd planned to meet at her place after my stupid workshop and after Ben finished his run.. No sense wearing out the bed sheets in Ben's or my hotel room.

Ben was a short-haul trucker, running loads from Seattle to Portland/Vancouver and back to Seattle every day. His wife had told him 2 days ago that she wanted him to get a hotel and not come home for the weekend... 'She needed some time to herself'. Apparently, she'd done that a couple of times before, so Ben hadn't thought too much about it, that is until the call came in yesterday from his wife telling him she was divorcing him, and he didn't need to come home cuz she'd changed the locks and was going to keep fucking her boss until he put a ring on her finger.

Fuck! That's cold, bitch! But...

That's what put Ben belly up to the bar and started the whole incredible roller coaster encounter last night! So thank you Ben's wife!

Both Susan and I were looking forward to Ben having a full "load" or two for us when he finished his short haul! Damn! That trucker could deliver the goods, and then some! Drunk on his ass last night. Dumped by his bitch wife last night. And, he still delivered full loads to both Susan and me! Actually, 2 loads to me cuz Susan had been kind enough to share her very yummy mouthful with me after Ben so generously supplied her with his 9" horse cock!

My thoughts were suddenly jerked back to reality as my Boss continued her ruination of my plans with Ben & Susan.

"I was thinking you and I should get some dinner, on the Company of course, and brainstorm the Collins Account a bit.. What do you say?" Diane was clearly throwing a monkey wrench into my plans with Ben & Susan. There just has to be a way to dodge her somehow!

Shit! Shit! Shit! How am I going to get out of this? The Collins account was our profit sweet spot, and lately, they'd been sounding more than a little restless. I'd been a hero 3 years ago when I closed them. It paid me one helluva nice commission, and got me a promotion to boot. I certainly know the account better than anyone else in our sales division, so it made perfect sense for my boss to want me in on any consult on Collins, but FUCK! I had a huge, hard cock and very wet pussy waiting for me tonight! Collins can wait, dammit!

Think dumbshit...THINK! There's got to be a way to put Diane off.

"How about this Diane? Let me gather up the docs on Collins for the last year. I'll go over every transaction, any glitches or complaints, and how we responded, and then let's debrief early Monday in your office. That should give us a handle on why they might be going a little soft on renewing with us next month. What do you say?"

"Hmmm... No, I really think we can put a winner together now, and who are you kidding, Caleb? You know Collins inside and out already! You don't need to pull any account docs! Meet me at Jake's at 7:30."

Diane walked away having crushed my feverish libido like the fucking ball buster she was turning out to be! Sure...she was probably fucking hot under all that professional attire, lesbian or not, but she was fucking up my wet dream and it was pissing me off!, Nevertheless, I couldn't help but stare hungrily at Diane's perfect ass until she was out of sight. What a fucking dick I am!

"Susan? It's Caleb. My fucking boss just nailed me to the cross! She wants to talk biz on our biggest account over dinner. There's no way I'm going to make it tonight. I'm soooo pissed! I wanted so much to taste your hot pussy again and suck a load out of Ben's massive cock while you watched!"

"Oh, Baby... No! Can we do tomorrow night then? I know Ben won't mind 3 nights of revenge on his bitch wife"

"Yes, yes, yes! I'm about to jizz in my pants right now just thinking about it!"

"Oooh, Baby... save it for me! And Caleb, I'm going to need you to eat my ass again like you did last night, only this time, when you've got me all wet and tingly back there, this time, I want you to butt fuck me hard, I mean like you want to hurt me Caleb...HARD...okay Baby?"

My cock was trying out for a Quality Control job with Dockers, nearly ripping a hole in my pants! The bulge in my shorts was so obvious that the hotel employee cleaning up after the training workshop couldn't keep from smiling as she witnessed my sorry state!

"I promise I will pound the shit out of your sweet tush, Susan!"

"FUCK! FUCK! FUCK!" To say I was frustrated, would be an understatement! The poor cleanup lady didn't know whether to run or drop to her knees and pray! This gringo was obviously mental!

******

OK, Diane said Jake's at 7:30, right? It's 8 fucking 10! Where the fuck are you Diane?

My temper was at about an 11 on a scale of 10! Not only had Diane screwed up what promised to be an amazing sequel to last night, she didn't even have the courtesy to call me and let me know that she wasn't going to make it! Fuck it. I pushed my chair back and was about to leave when...

"Holy fucking shit!"

I stared in disbelief as I saw Diane walking past the hostess toward me, and she was THE HOTTEST fucking piece of feminine mystique in 3 States!!! I had NEVER seen my boss like this! Her tiny black dress was hugging her slim body like a sex starved love glove and the plunging neckline displayed her full breasts, leaving no doubt to any onlookers that she did NOT need a bra to present those amazing orbs to their fullest advantage! And, there were plenty of onlookers! The whole restaurant was silenced in awe! Diane was fucking STUNNING!

"So sorry to be late, Caleb. I hate being late, but the hotel didn't get my dress back from alterations until 7:45. I've lost a couple of pounds with my new exercise program, and I didn't want to show up for dinner with my top top sales guy looking tacky!"

All the saliva in my mouth had burned away 10 feet away from Diane's arrival at our table. I'm sure my mouth was hanging wide open, and I was barely able to stammer out a lame, "you look great."

"Well, thank you, Caleb. You look very nice too, but then, you ALWAYS look nice, don't you?

I may be fooling myself, but did my boss, Diane, just put some emphasis on the word 'ALWAYS'? Holy shit! All of a sudden, my dick was oblivious to the fact that Diane was my boss, and all my dick was thinking was, "how the fuck can I get this HOT fucking cunt into bed?"

Side note...Dicks, BTW, have NO common sense. Dicks only know what they WANT! And right now, my dick wanted Diane!

"Earth to Caleb...Are you okay?"

She had a little smile beginning to show, and I knew I had to get my other 'head' back into the game.

"Oh, wow, yes I'm fine, (I lied,) I was just thinking about the Collins Account. Sorry.,"

Diane tilted her head a tiny bit to the side, and smiled. I nearly came in my shorts!

"Well, as much as I value your dedication, Caleb, I'm thinking you were right earlier today. Let's NOT even give a thought to the Collins Account tonight and just enjoy a superb dinner and each other's company. We deserve a little pleasure once in a while, don't we?"

OMG!

My boss is coming on to me! Is that even possible? I mean, what else could all this 'pleasure' talk be? My ball busting, hard nosed, nothing but business boss was HOT TO TROT, or I've lost all of my "She wants to FUCK me" skills, and I KNOW that's NOT the case! I can smell hungry pussy and "please please please suck my cock" a mile away, and Diane's pussy was HUNGRY!

"Well, I have to say, Boss. That being the case, I'm the luckiest guy in this restaurant tonight, cuz there isn't a man here who wouldn;t sharpen a butter knife and take me out, just to be able to be sitting with the most beautiful woman in the place! My god! You look amazing!"

I knew it was a bit risky to dive into the dance so openly, but when the dick takes the wheel, well, that's just how it goes.

"Oh my, Caleb! You're making me blush. Thank you. You flatter me. I don't know how to say this really, but please don't feel like you have to say nice things to me just because I'm your boss. Tonight, Caleb, I want us to just be who we are, a guy and a gal enjoying an evening together. Can we do that? Is that too weird?"

I swallowed hard and tried to catch my breath a little. My heart was at about 120 beats/minute, and I was absolutely sure my swollen cock was going to rip open my pants any minute now and force me to do obscenely vile things to the temptress before me, even though that seemingly willing temptress has the financial power over me to cut my swollen balls off and brutally shove them up my ass!

"What the fuck are you thinking, Caleb?" I asked myself. "This could very easily put your ass into some downtown soup kitchen shelter! Get your head out of your butt, Dude!"

"Yes. Of course. I would love to relax and enjoy an evening "off" with you. Do you have a favorite wine?"

The dinner with Diane had been much more relaxing and enjoyable than I'd anticipated. The food, of course, was great, but even better was the conversation.

We talked about everything EXCEPT business, and as horny and driven as my dick had pressed me to be, I found myself truly beginning to like Diane. She had a definite sense of humor and interests I'd NEVER suspected. She has been studying Italian for a year because she wanted very much to go to Italy and really be able to hear and understand the locals.

She has been training at a small but highly acclaimed karate dojo for nearly 3 years, and had recently won her skeet club shooting championship for the second year in a row. Holy cow! This is one amazing lady! She's smart, she's a fighter, and she shoots fucking shotguns... FOR FUN!

Damn! I may just be falling in love with my Boss!

"Diane. I am overwhelmed! I had NO idea! You are amazing! I, on the other hand, well sadly, I work...I go home...I eat...I sleep. Then, I wake up and go back to work. I feel like I should be shining your heels right now or rushing your karate gi to the cleaners! I'm NOT worthy, Mistress!! I am definitely not worthy!"

Diane's eyes sparkled in a way I'd never seen. She was silent for a long time but it was clear that she was working through what she was going to say next... and I was definitely NOT prepared for this!

"Caleb...you know I like you and I trust you completely. You are my absolute best sales guy, hands down, but tonight, no Company, no boss, and no accounts...

"Caleb, tonight, I want you to take me upstairs right now and fuck me like a whore!"

OH my fucking god!!! Did I really hear what I think I just heard?

So much for 'She's a lesbian' office pool!

*********

"Oh my god, Diane! I can't breathe! I talk for a living, but I'm completely speechless!"

She was so calm... She just looked at me with her sparkling blue-gray eyes.

"Caleb... you don't have to say a word. Just, PLEASE, take my hand right now and take me to your room and fuck me like a cheap whore until I scream!"

My big head was swimming and my smaller head was about to tear its way out of my pants like the alien chest tenant in the movie, Alien!

This can't be happening! This is my BOSS, for god's sake! NO! This can't be my Boss. This is some sadistic demon who's planning to viciously extract my man juice as State's Evidence #1 of the heinous crimes of rape and terminal STUPIDITY in order to throw me into prison for the rest of my sorry life, where my 29 year old ass hole and my 29 year old mouth will be stuffed over and over and over again by every bull in the penal system, including the fucking Warden!

But...

My other head, of course, simply took Diane's hand and headed for the elevators.

***********

'Stunning' is not a big enough word. 'Unbelievable' is so true, but here she is... right in front of me, and I'm unzipping the back of her LBD, (Little Black Dress, btw). My super straight laced, business only Boss was about to be completely naked in front of me, AND let's not forget... she had practically ordered me to fuck her brains out!

Am I dreaming? Did the hotel spike all of our beverages with some kind of hallucinogenic? Nope. Diane was as beautifully real as real can be, and she was about to hungrily submit to my every carnal desire. TyTyTy, There is indeed a god in heaven!

That sexy black dress that had turned every head in Jake's, including and especially mine, fell silently to the floor. I'd been 100% right about Diane having NO NEED for a bra. Her full, firm, amazing breasts were standing strong and proud and her nipples were hard as peach pits and nearly as big. I was on the edge of crazy knowing that I was not only seconds away from tasting those delicious nipples, but I would also be joyously obeying my beautiful boss's last command! My cock was a piece of solid steel in my pants and Diane's tight ass was pressing back against me, knowing full well what she was doing to me!

"Oh my, Caleb, you are so hard! Don't make me wait another second! I need you to fuck me hard Caleb...Fuck me NOW!"

I slid my hand down her back and squeezed her tight, sexy butt. Picking her up in my arms, I carried her to my bed. Those incredible nipples were only inches from my lips now as I laid her gently down. There was no way I was going to miss out on devouring both nipples and a whole lot more. I ripped my pants off and moved one leg over Diane's gorgeous body! As I hungrily swirled my tongue around first one and then the other nipple, Diane's moans turned into deep throated growls. She was like an animal, and I wanted to devour her!

"Oh fuck, Caleb! I can't take it! I want you to drive your hard cock into my pussy and fuck me until I scream!"

As much as I wanted this to NEVER end, I knew this was not a time to tease or delay. Diane was on the ragged edge of insanity, and so was I. I drove my pulsing steel rod as deep and hard into Diane's soaking wet pussy as I possibly could. Diane's legs immediately curled around my back and pulled me in even deeper!

Each time I drew back preparing to drive my dick home again, she would loosen her legs and then slam me into her hot pussy! God, I was in heaven!

"Fuck me Caleb! Fuck me like the whore that I am! Don't stop. I want you to fuck me until you fill my hot cunt with your cum!"

I rammed into Diane while my eyes rolled back into my head. Her amazingly strong legs matched the rhythm of my thrusts perfectly and her entire body trembled like the early tremors of a massive earthquake. There was no way I could hold back the explosion that shook me!

"Fuck Diane...Fuck! I'm cumming!"

"Yes, yes, yes! Don't stop, baby! Don't stop!"

In the month of May a few years back, Mt. St Helens erupted, blowing half the mountain into the atmosphere. Tonight, St Helens had nothing on me!

**********

I was a rag doll. Every cell in my body had erupted into the fireworks of a pure pleasure like I had never felt before. The full weight of my exhausted body lay heavily on Diane and realizing that, I started to move to the side to give her a chance to breathe again.

"No, no, please Caleb! Don't move... not yet."

Diane's legs were still wrapped around me and she was grinding her wet pussy against my rapidly softening member. Her beautiful body was trembling with a lust that had built up to an atomic level as I'd fucked her and then filled her with more cum than I had ever before delivered! She was moaning and an aching growl was coming from deep in her throat, that finally woke my stupid ass up!

My Boss had ordered me to fuck her until she SCREAMED! And here I was, basking in the heavenly afterglow of the most amazing orgasm I'd ever had. What a selfish bastard I am! Diane should fire me as the lousy, disobedient employee I am, who doesn't even have the good sense to do what the Boss says to do!

Despite her objections, I slid to Diane's side and began kissing her ears and neck lingering for only a moment with each kiss to taste my beautiful Diane with tiny flits of my tongue. Her moans, becoming deeper and deeper, were beginning to tell me that she might just be willing to forgive my selfishness. When I lowered my lips to her nipple, she nearly suffocated me as she pulled my neck and mouth hard against her breast.

"Oh god, baby! Don't stop. Don't ever stop!"

I rolled Diane's other nipple between my thumb and finger, squeezing a bit until she winced from the delicious pain. The sounds coming from deep in her throat were becoming more and more animal-like. I was sucking and pinching the hard, thumb size nipples of a ravenous female BEAST! What had I ever done to deserve this?

Releasing Diane's nipples, I leaned up and drove the tip of my tongue as deep into her left ear as I could. She gasped and growled loudly, pushing her ear into my probing tongue as though she wanted me to penetrate her brain. Pulling back, I whispered,

"Baby. I'm going to bury my tongue in your pussy like I just did in your ear! I'm going to eat your hot, wet, cum filled cunt until you SCREAM!"

As I slid my tongue down Diane's body, she grabbed me by my shoulders and pulled me down hard toward her aching slit. I let my hot breath bathe her wet triangle for just a brief second and then slid my flattened tongue from the bottom to the top of her pussy lips, lightly flicking her clit to ready her for what I knew she was desperately needing. The taste and smell of her wetness mixed with my cum was intoxicating, and I couldn't wait to plunge my hungry tongue into her!

"I need you Caleb! I need you soooo bad!"

This whole amazing day began with me nearly hating my super professional Boss for fucking up my delicious plans with Susan and Ben, only to be transformed into the most intensely satisfying sex of my lifetime. I could hardly believe it, but Diane, my ALWAYS straight-laced Boss, was begging me to ravage her hot pussy!!!

"YES! YES! YES! Oh my god, Y E S Caleb! Eat me! Eat my nasty whore cunt, you son of a bitch! Don't you dare stop! Eat me Eat... Aaahhheeeeeeee! Yes! OH FUCK YES! AAAAAAAAHHHHEEEEEEEEEEEEEEE!!!"

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