Getting started Ch. 01

Diane laughed. "Oh, you are too smooth! Going to get me in trouble. But - thanks." She looked down at her chest. "Hers are a little... fuller. Perfect? Seriously? God, no one has ever said that." Her voice trailed off, and then she picked up on the referral thought. "Oh, you are welcome! I think Eve texted you right after I gave her your number. She's in town next week, right?"

"Yep, meeting Thursday," I said, watching carefully for any hint of a reaction.

"Oh, that's great! She'll love you." She paused to take a sip of her drink, which was almost gone. "I had an idea. We're doing an executive retreat in a couple of weeks in Beaver Creek. Have you ever done any consulting work?"

"Sure - I just don't know anywhere near what you know about your industry." Where was this going? Seemed like a big subject change.

"Oh, that's OK - could you do a report on something like the political spectrum and how it might impact tech?" She paused, giving me space to respond.

"That I can do - be a good excuse to meet with some political types I know. "

"Great - you have some connections?"

I nodded.

"Even better. So here's my thought: If you can, come up to Beaver Creek and stay. That way I can literally pay you as a consultant - as long as you don't mind getting paid by check or direct deposit as a 1099 contractor."

"That works well - you're on. Is corp to corp OK? When is it?" We both smiled, knowing that she had just arranged for me to be her companion on the company dime. It was a creative solution for both of us. And I wasn't too worried about being paid by check or direct deposit - it would account for the additional income, and I could set up a corporation to shelter it from taxes.

"Good. Yes re corp - actually makes it easier. I'll have my HR person send you the paperwork." She finished her drink and ordered another round, even though I was only halfway through mine. "And I'll send you Beaver Creek info."

"Great. Good ski area, too."

She smiled. "Do you ski much?"

"Oh, some. Not great at it - on the cusp between intermediate and advanced. I can get down almost anything, but don't do bumps or trees. You?"

"Oh, probably the same. We usually come out to Aspen for a week after Christmas. Not sure we will this year - husband will probably have to work, since he had last year off."

"Mmmm. What does he do?"

"He's a doc - internal medicine."

I noticed that she wasn't wearing her rings - and remembered she hadn't worn them the first time we met.

"That'll keep him busy!"

"Yep, you can say that again. Between that and my travel schedule it's amazing we're ever in the house at the same time. Which is probably just as well. He'd be scandalized that we had unprotected sex."

She took a gulp of her second drink. "You're a little behind," she said, grinning, motioning with her head to my drink.

"Strong drink giveth the desire, and taketh away the ability, to bastardize Shakespeare." I caught up to her previous sentence. "He'd be fine with sex, just not the unprotected part?"

Diane laughed. "Wow, he even knows Shakespeare! No question about ability." She paused. "Oh, he'd be scandalized anyway if he knew, but we adopted a sort of "don't ask, don't tell" thing a while ago. Kind of had to, even if neither of us did much with it. And his drive is way down, while mine's shot up. Anyway. TMI?"

I shook my head. "No such thing. I just try to be sensitive about things like that."

She nodded. "I could tell - you asked if we should go up together or separately. Speaking of - ready?"

I took a pull of my second drink. "You bet. Lead on."

She motioned to the cocktail waitress and signed the drinks to her room again, and I picked up my backpack.

We made our way over to the elevators - and Diane was a lot flirtier and touchier than she'd been when we first met, putting a hand on my back as we walked. We made it to her floor - 18 this time - and she bounced down to room 1807, clicking it open with her phone. As we walked in, she kicked off her sandals, and as the door closed behind me she headed straight for me, wrapping her arms around me, pulling my head to hers, her lips searching for mine, finding them, kissing me hard, me responding quickly, feeling her press her body to mine, one hand moving down my spine, finding my butt, squeezing it, then moving back up as she started backing us up toward the bed.

As we were shuffling along, kissing passionately, her hand reached under my shirt and lifted, interrupting our kiss just long enough to get my shirt off and drop it on the floor. She moved to the button of my shorts, undoing it, palming my now fully erect cock through the fabric before undoing the zipper and pushing them down, leaving me in my bikini briefs, the tip of my cock pushing over the waistband. She took my cock in her hand and squeezed, then let go and started pushing my briefs down and off me.

I'd gotten the memo - and when she was done stripping me I lifted her blouse off - thankfully it didn't have buttons or I might have broken them - kissing her hard as her blouse floated to the floor, then undoing the clip on her bra, releasing those beautiful breasts, feeling them against my chest. My hands moved to her skirt, seeking out a zipper or button and not finding one, slid it down - aha - elastic! - and then pushing her tiny thong down and off.

As we stood there naked, kissing passionately, she turned us so that I was now back to the bed, and she pushed me down on the bed, breaking our kiss and climbing on top of me as I moved to get my whole body on the bed. She positioned herself above my cock, which was aching for her, and she used a hand to guide me to her entrance and then slowly sank down until she was completely impaled on my cock. We both moaned softly as she settled on my cock, and after a moment, started to rock back and forth and side to side. While I was quickly in that wonderful haze of sex as she pumped up and down on my cock with her glorious pussy, I remember being amazed at how wet she was as she sank my cock into her.

As we fucked, I could feel my balls swelling and willed them back down. Yeah, right. I could feel her orgasm building too, and she took her time letting it claim her, finally throwing her head onto my chest as her orgasm claimed her, rolling over her whole body, and triggering me as well. My hands clawed at her hips to hold myself in her as deeply as possible, and felt my cum erupt inside her, filling her amazing cunt with hot seed, rope after sticky white rope. And feeling my cum inside her triggered her again, and her pussy clamped down on my cock again, stimulating yet another rope of semen from me.

We stayed there, her on top, impaled on my cock, juices slowly leaking out, and she lifted herself back to vertical, settling on my cock just that little bit more, and smiled dreamily.

"God did I need that... " she murmured, her pussy still squeezing and relaxing on my cock, which responded with twitches of its own. "Mmmmm."

"Mmmm... amazing. You can do that any time," I murmured back, enjoying the view - her proud breasts jutting forward, that beautiful hair framing her face, contentment radiating from her. And from me too, I have to say.

We stayed like that for a while - long enough for my cock to soften slightly and then recharge, which made me start to reach to move her - I wanted to lay her down and take her. I think she read my mind - we managed to move without uncoupling, and she moved my mouth to one of her perfect breasts.

I started to tongue and suck her nipple, and took her breast into my mouth, sucking hard and letting my teeth graze her nipple, making her shake and moan as I did.

"You can go a little harder," she said in a voice that was half a murmur and half a pant.

Rather than stop to say anything, I bit down just a little, and felt her arch her back and her pussy contract even more on my cock. "Uhhhh... " was all she managed as I kept it up. I don't know how, but Diane turned me on like I had never been before. And so it was easy to read when I hit her upper limit for pressure on her nipple. I gave it a kiss and switched to the other, repeating the process, and feeling her start to shake as another orgasm grew inside her.

It didn't take long for it to claim her, as my teeth grazed and gently bit on her nipple and breast, and I felt one hand flail around as her other hand clawed at my ass, trying to pull my cock into her even deeper. As she tried to writhe around I held her in place, and just let her orgasm wash over her, feeling her flood my cock as she came. After a while, her breathing settled down, and her eyes opened as she shook her head.

"Hi," she said softly.

"Hi," I said back - also softly.

"I want that all night," she replied. "Can we do that?" There was a slight sheen of sweat over her eyes, which was irrationally sexy to me.

"You bet. I am yours for the night."

She gave an almost shy smile. "Good. Just to let you know - I can be demanding."

"That's OK - means you know what you like. Good quality." I had slipped out of her as we talked, making her give a little pout.

"Hey," she objected as we decoupled.

"Don't worry - we've got plenty of time. What's your morning like?

"Open, actually - flight's at 1, and no meetings or anything. Always on call, but not too many calls I have to answer. CEO or COO, yes. Almost anyone else can wait."

I was lying on top of her, reveling in the feel of her body against mine, propping myself on my elbows. My cock was sliding around on her groin and tummy, which were slick from our combined juices and a bit of her sweat. I inched my way down a little to let my cock slip between her legs, which I was holding together with my own. I could feel her heat as my cock slipped around on her.

"Mmmmm. Nap on the plane?"

"If I can. I should have gotten a Saturday flight and booked you for Friday." She squirmed a little as my cock played in between her legs.

"Next time... I'm all for it."

She'd been shifting her body as we talked and kissed, and finally maneuvered to where my cock was at her entrance. She smiled and eased me forward, just a little bit, and smiled wider as I entered her again, both of us slippery as hell from all our juices.

"That's better," she murmured as she kissed me again. "Feeling you inside me is just... magic." She squeezed her legs together and pulled me forward a little more, engulfing my whole cock, my legs on the outside of hers, which were tight together now. A great position - I think it creates a lot of natural pressure on my cock. She started to rhythmically squeeze me, which normally would only make me even harder, but as I was as hard as I can get, it was just stimulating, and I could feel my balls filling again.

"I am not going to last long if you keep that up," I murmured into her ear, kissing her neck and tonguing it hard - I would have loved to bite down, but didn't want to leave any kind of mark.

"Mmmmm... good. I want to feel you cum again... "

I was almost panting now as she kept up her rhythmic squeezing. "You like feeling me cum in you?"

"Oh, sweetie - there is nothing better than feeling that shot of heat deep inside and knowing I made you do it... " The huskiest voice I'd heard from her - super sexy. She was in far more control than me - I was right on the verge. And she could tell - she reached down and gently clawed my ass, urging me into her even deeper, if that were possible.

She kept whispering in that sexy husky voice, "I want you to cum - feel you spurting inside me... giving me your hot seed...

And I'm not sure which part did it, but I couldn't resist - I tipped over and I did exactly what she said, my cum spurting into her again, feeling like it was boiling into her, coating the inside of her amazing cunt with my cum, feeling her stiffen as she felt me spurting, her hands holding my ass in place to keep me as deep as possible.

I lay on top of her, shaking, for a minute or two, still planted deep in her. And when I could focus, she was watching me with a brilliant broad smile on her face.

"Mmmmm. That was great. Love how that feels!" she whispered to me. And I think you just might like cumming in me... " giving me an impish little smile as she said it.

"God yeah... " was about all I could manage. "It is fuckin' amazing." I was surprised I said it, but she loved it.

The rest of the night was spent alternately dozing and fucking - whoever woke up would stroke the other, we'd both be awake, couple again, and doze back off.

There was one time where I woke up with a raging erection, which made me think it was close to morning, just as it had been with Linda. Still in something of a light haze, I saw Diane sleeping next to me on her stomach, her legs splayed apart, that beautiful ass slightly elevated. And without a thought, I moved over her, straddling her, and sank my cock into her. That woke her up for sure - I felt her wake up and moan as I slid in and out of her, straddling that gorgeous ass.

It's one of my favorite positions - I think it allows for the deepest penetration - and it also let my cock hit her magic spot pretty easily. And as I thrust in and out of her, she started egging me on again.

"Mmmm... that's right Bob, fuck me. Fuck me hard. Fuck me until you cum... I want to feel you cum in me again. Give me your hot seed again... " And while I would have cum inside her again anyway, her drumbeat accelerated it.

I'm sure she could tell I was close, because she kept going, a little faster: "Mmmmm... that's right, Bob, fuck my sopping cunt. Cum in me - I know you're ready. Let go and give me all your hot seed - make me feel that spurt of heat again... that's right, cum for me now... "

The perfect storm: I bottomed out in her right as her beautiful cunt spasmed on my cock, squeezing hard as I felt like I brushed her cervix, and she practically yelled at me, "That's right, cum for me now... " So I did. I gave a great yell as the tip of my cock mushroomed and I exploded, relieving the huge tension that had built up in me. Stream after stream of semen leapt out of my cock deep into her beautiful body, her ass pushing back against me to make sure I was as deep as possible and to get every last drop she could. I was dimly surprised at how much cum I blasted into her, considering our earlier adventures.

I kept myself buried in her as long as I could, shaking a little at the power of the orgasm that I had just had. And when I finally slipped out of her, she pushed me down on the bed, slithered on top of me, and kissed me hard.

"YES! That's exactly what I want you to do every time. Take me. Fuck me. Cum in me over and over..." she practically hissed it out as an order. "And fuck me over and over... that's what I need."

Her words snapped me back pretty quickly. And even if they hadn't, her sliding back and mounting me again would have. Her pussy was so wet there was zero friction - which made it harder to stay in her, especially when she squeezed me with her powerful muscles.

"Are you ready to do that? Ready to fuck me every time you see me?"

"Oh, fuck yeah," I said, my body and strength returning quickly as she rode my cock, but gently to keep us coupled.

"Mmmmm, that's the right answer," she replied, coming off my cock and kissing me again, hard.

She lay down on me again, her head on my shoulder, and I briefly wondered how the universe had decided to put us together. I could feel drops of fluid leaking from her and falling on me, and we must have both dozed off again.

Because the next thing I knew, it was daylight out and Diane had mounted me and was riding back and forth, her eyes closed and a smile on her face. It was a heavenly feeling, even if she was so wet that she had to move carefully lest I slip out. And seeing her beautiful tits swaying as she rode me was intoxicating all by itself. I reached up to tweak them, and felt her sharp intake of breath as I fingered them.

"Mmmmm... love that," she murmured. She rocked back and forth on my cock a little bit. "And that," she added.

I smiled even if her eyes were closed. "You have the most beautiful tits," I said, almost dreamily, rolling her nipples between my fingers. "They really are perfect."

She smiled, in a haze of her own. "Glad you like them... "

We kept that up for a while, and between her rocking herself back and forth on my cock, and my twirling her nipples, she worked herself into another orgasm - this one kind of sneaky sudden, as she suddenly stiffened, squeezed me hard, and cried out as it washed over her, punctuated by a quick pulse of warm liquid from her that landed on my groin and stomach, slowly trickling away.

As she came down from her orgasm, she kind of collapsed onto me, my cock sliding out of her absolutely drenched pussy and those perfect tits landing on my chest.

"Holy shit - did I actually squirt?" she wanted to know.

"I think you did - that was HOT!"

"Wow. Never happened before. See what you do to me?"

"Says the woman who's made me cum how many times? Four?"

She corrected me quickly. "Five. Impressive." And gave me a charming smirk. "And I don't know how many times you've made me cum... "

"More than me, I hope!"

She laughed. "Yeah, that's a safe bet. I can't believe what you do to me... I just want you to fuck me. I'll think of you and get wet in the middle of a meeting. I thought those days were gone with my 20s and 30s."

"Oh, hell, you're just getting started... "

We bantered for a little bit, and then it was time to get up and moving. She pulled on a robe as I got dressed, and then came over to me, a serious look on her face.

She put an envelope on my chest. "Here. That's 25. Get the paperwork from HR done - we'll do that for every overnight. Don't say a word." She reached up and kissed me again. "Thank you - I didn't know this part of me could ever come out again. Now go - I have to catch a plane."

I kissed her back hard. "Thank you. I will. Back in a couple of weeks?"

"Yep - I'll text you the deets. Have fun with Eve," she said with a smirk. "See you."

And with that, I was out the door, hearing it click shut behind me as I staggered a bit to the elevator, Diane's scent all over me.

The first thing I did when I got home was drink a 32 ounce bottle of Gatorade. The second was to make myself a huge 'breakfast' of bacon, eggs, and an English muffin. The third was to look up creating the necessary corporate entity - I knew Diane would not dilly-dally around getting that set up.

I went out on a more normal date on Saturday - it was with a woman I'd been out with a few times before, and, not for the first time, we wound up back at her house. It was... OK. Nothing like with Diane, or Julia, or Linda. She seemed to think it was great - which was good. We went to breakfast the next morning, and agreed we'd get together again when our schedules overlapped. And while it was fine, I found myself missing the... edge, the excitement, the... anticipation I had with Diane, Julia, and Linda.

So I was actually glad to have the next week mostly free - I spent a couple of days at a professional development class, but otherwise just did my usual biking, listening to music, reading, etc. And while it was great having the time and recharging, I found myself missing the banter and the sex, particularly with Diane. I'd found myself comparing my Saturday night date, Katie, to Diane and, to be brutally honest, Katie came in second in every department.

Thursday rolled around, and I was glad to dive into my normal pre-massage routine. Shower, shave, including groin, brush teeth, dress, check backpack, check drive time, all the while idly wondering what Eve looked like. Diane had said Eve would love me, and I just hoped she'd be in the same ballpark appearance-wise as Diane, Julia, and Linda. Since we were at the Four Seasons, I figured I should dress a little more, and wore a pair of cotton Dockers with a polo shirt and black dress shoes from Ecco, which had never failed to draw a compliment.