Getting started Ch. 01

"Thanks again - I'll look forward to next time!" Laila gave me a last passionate kiss and headed back to her room. I watched her bounce - it's the only word that fits - out of the hotel coffee shop as she made her way to the elevator bank and I chuckled to myself. I was now richer by $4000 in cash and poorer by four ejaculations - three deep inside her wonderfully tight pussy and one down her throat. It had been a great night - I'd been her "date" to a corporate cocktail party/dinner, and then basically her sex toy for the night. She was a married corporate exec who had a "nice but boring" husband, traveled a lot to the Denver area for work, and had no good outlet for her powerful sexuality.

It was the third time she'd been here - Denver was a monthly stop for her - and she was becoming a regular client. It was a pretty typical gig for me these days. I'd get a text from someone asking if they could set up a massage appointment. We'd figure out the day, time, and where they'd be staying, and I'd show up, usually meeting them at the bar of the hotel they were staying in. They were all high-level businesswomen, often "-C" level, or doctors, or lawyers, government people, etc. Almost all of them were traveling, and most of them, if not almost all, were married. And without exception, they were all very good looking, with some I'd call drop dead beautiful

As great a night it had been, it was, dare I say, somewhat typical at this point. I'd started a couple of years ago, and one thing had led to another, to the point I was making more going out with women than I was as a teacher. Life, as they say, can be funny. Who knew this would happen? Certainly not me - I'd been the guest or 'date' of women ranging from corporate executives to doctors and lawyers to politicians. I averaged three clients a week, most of them now overnights, for which they'd hand me an envelope with 30 $100 bills in it; occasionally more. There were a few women who were able to retain me as a "consultant," which meant I'd see a direct deposit show up in my bank account along with a 1099 form at the end of the year.

So how'd I get started? (I have to laugh as I write that - who'd believe it? And yet, here I am.)

Well, every so often I'd put an ad on the web offering sensual/erotic massage. I think I'm a reasonably attractive guy - I'm 47, about 6'1", 185 lbs., in pretty good shape, divorced, etc. Full head of gray/silver (take your pick!) hair, with glasses, educated, and active. I'd had a range of careers; and was currently teaching high school, having been in the military (three different times), in high tech, been a lawyer, etc. So I was never shy about posting a picture with my ad, which helped. Never one that was too obviously me, but I'd send one on request to someone I thought was real.

I'd met a few women off of the ad, and we'd communicate, usually meet for a drink, and then move back to usually my house for a 'massage.' For anyone who doesn't know, offering a 'sensual massage' is code for sex.

I'd posted the ad again toward the end of the school year, and got the usual range of responses - lots of obvious spam, a few from real people. Typically at least a couple of the real people would actually meet; if we got that far there were very few who declined come over. After the usual filtering of the spam responses, I saw that a woman named Diane had emailed me, asking if I was open on a Wednesday to massage her at her hotel - she was traveling on business. Of course I replied that I was indeed - would she like to meet at the bar? She thought that a very good idea, so we agreed to meet at 9 at the hotel bar.

I went through my usual pre-date/massage routine - big dinner, shower, shave, teeth, etc. And checked my massage bag - a small backpack from my Army days, where I kept massage oils, a couple of towels, condoms, a couple of feathers, toothbrush and toothpaste, and some small electric candles. Cheesy? Maybe. But women seemed to like that I thought of it. And I was off to Diane's hotel.

Her hotel was one of the big ones in the nearby tech center, well known and usually full of corporate folks during the week. Always very clean, and reasonably tastefully decorated for the 'high-end executive" hotel it promoted itself as. I'd been to the bar before - this wasn't my first rodeo at this hotel - so I parked and found my way to the bar, picking a bar table that was a bit darker than the others.

I looked at my phone, and had a new email: "Hi! I'm on the way down now."

"Great! I'm at one of the cocktail tables by the end of the bar. See you in a minute," I typed back.

A moment later, I saw her walk in - and I think a lot of the other men in the bar did too. Diane is on the taller side - probably 5'8", maybe 5'9". Shoulder length dark hair, and a beautifully proportioned figure - no one part dominated. Athletic looking, without that starving-runner physique. And a face that I thought was just stunning. She was wearing what looked like a black miniskirt with a floral print blouse, both snug enough to let everyone see her figure.

I stood up and waved - she saw me and flashed a bright smile as she headed over. I walked around the table to greet her with a hug.

"Hi Diane! Nice to meet you," I said as we hugged briefly - the 'corporate approved' version.

"And nice to meet you," she replied, smiling. "I've been looking forward to it."

"Me as well. What would you like to drink?" Conveniently, a cocktail waitress arrived and Diane asked for a cosmopolitan.

We sat down, and her drink appeared promptly - almost instantly.

"And how the heck are you? Long day?"

She smiled. "Pretty good, but it's been a long couple of days." She took a good sip of her drink and considered it thoughtfully. "That's pretty good." She waved down the waitress and asked for another.

We went through some typical small talk, and she finished her second drink as I finished mine. I learned that she was 49, married with two kids, one in college and one about to go, had been with her current IT company for 7 years, a variety of progressive jobs in other companies before, etc. I got the impression she was something of a "fixer" for whatever company she was at.

She laughed when I said that. "Something like that - I always get sent whenever there's a problem and the CEO needs someone they know to go find and fix it. I'll give you my card later."

I nodded. "I did the same kind of thing when I was a lawyer."

That got her attention. "You used to be a lawyer, and now teach? How did that happen?"

"Choice. I was practicing when I got activated by the Army and sent to Iraq. And realized how pointless lawyering was, aside from the money. So now I teach high school. Much more rewarding."

"And you add in a massage now and then?"

My turn to laugh. "Yep, that's about right!"

She grinned. "OK, shall we?"

"You bet. Should we go together or should I wait?"

She pondered for a second. "Let's just go."

"OK." I threw my backpack on my left shoulder, and she led the way to the elevators, after signing the drinks to her room. ("Per diem - I never hit it, and no one would care anyway," was her quick explanation.)

As we made our way to the elevator, I could feel my loins rising - she was, if my description of her didn't make it clear, very attractive, and had an undercurrent of sexiness that I liked - understated is usually preferable to me. We went up the elevator to the top floor, and she led the way to her room, opening it with her phone.

"OK," she said as the door closed. "I'm new to anything like this. How do we start?" She chuckled softly as she said it.

It was a common question - and a good one. How do you initiate sex with a stranger you might have met only an hour ago?

"You've had massage before, right?" She nodded. "Just think of it as a regular massage. I'll step into the bathroom and you can disrobe to your comfort level and lie down - face down to start. Then I'll come out and start the massage, just like a regular massage. Then I'll start getting a little more sensual - if you get uncomfortable just say so and I'll stop. Make sense?"

She nodded. "OK. I should warn you - it's been so long since I've had a good massage I hope I don't orgasm as soon as you touch me." Again with the soft chuckle.

"Ha. Perfectly ok if you do," I replied, adding a soft laugh of my own.

And with that, she stepped into the bath and closed the door. I walked over by the window and started setting up, but could still trace her through the bath - I have good hearing. Toilet, wash hands, brush teeth, rinse, dry hands, and the door was opening. While she'd been in the bath, I'd put up a few electric candles and turned them on (hotels frown on any type of open flame - can you believe it?).

She walked out of the bath with a bright smile and said "Your turn!"

"Be with you momentarily," I said as I walked into the bath and basically repeated what she had done - my only addition was to drink a couple glasses of water. As I was in the bath, I saw that she was an efficient traveler - not much "stuff," and what was there was neatly arranged. The hallmark of a regular traveler. I stuck my head out the door and asked, "Ready?"

"Yep!" came the reply.

I stepped out of the bath and into the room, turning off the lights as I did. She was naked on the bed, face down, arms at her sides, her eyes closed. She made for a beautiful sight - her dark hair splashed on the pillow and her skin a nice contrast with the white of the sheets. I could feel myself stirring again, and moved to put the bottle of massage oil on a washcloth on the nightstand.

As I disrobed, I thought about where to start. Most people start with the neck and upper back, or lower back and work up. I've never liked starting a sensual massage at the neck - it's too sensual an area to start with, and starting with the low back gives her too much feel of me too soon - anticipation is one of the keys to a great sensual/erotic massage. So I often started with the feet, absent a request. So I reached for the massage oil, put a little on my hands to warm it up, and reached for her foot. And started working it. Her left foot, as it turned out.

"Mmmmm..... do you know how long it's been since anyone has massaged my feet?" she murmured.

"Long time, eh?" I murmured back.

"I can't even remember... years. Mmmm... "

I worked her foot, and started up her leg, varying pressure to maximize the contented sounds she was making. She had nice, firmly muscled legs - easy to work on. I worked up to just below her ass and then back down, letting my hand drift close to her sex but not too close - not yet. I worked my way back down, and then started on her right foot.

"Oh my god - that is heavenly. I could almost orgasm just from that!"

I leaned down to whisper in her ear. "You go right ahead, Diane... that's what this is for," earning an "Mmmmm... " from her.

I worked my way up her leg, and let my hand drift ever closer to her sex. I could feel her warmth, and felt her shift slightly, opening her legs just a bit. I worked back down her leg, and then started working up both her legs, one hand on each, straddling her legs as I worked my way up. This time I kept going up to her beautiful ass, and started kneading it, working her glutes but just softly enough that she'd know it wasn't a therapeutic massage.

And to underline that, my fingers crept closer and closer to her sex as I massaged her inner thighs, feeling her open her legs just a little bit more and feeling a sharp intake of breath as my finger grazed her, feeling her heat. I worked back up over her ass and to her lower back, up her spine, and then back down, again letting my fingers graze her, more obviously intentionally this time. I felt as much heard her "Mmmmmm... " as I did.

Time to turn things up! I moved to straddle her, and as I settled on her ass she could feel my fully erect cock come to rest between her cheeks, my tip near the small of her back. I leaned forward, letting my fingers trace up her spine, then back down, before gently massaging my way back up, my cock on her back. I could feel her relaxing, and started to kiss her lower back, moving up her spine slowly, planting kisses as I went. I reached the base of her neck, and with one hand moved her hair aside so I could kiss the base of her neck, right up to her hairline, then moving to the side of her neck and then just barely grazing her ear before slowly moving to the other side. All the while, my erect cock was on her back.

I could feel and hear her heavy breathing as I kissed my way around her neck and ears, and started moving back down, kissing out along her shoulders and then back down her spine, stopping in the small of her back and putting my hands on her ass, kneading, kneading, until I moved them down, to her inner thighs, feeling her heat, using a finger to trace her sex. And as I did, I could feel her shake as my finger explored, before finally sliding one and then two fingers into her. She was super slippery, and my fingers had no trouble sliding in, making her quake as I did.

Now she was making noises like "Uhhhhhh..." to go along with "mmmmm... " as I explored her pussy with my two fingers. In and out, oh so slowly. Rotating, finding that little mound of rougher tissue, gently stroking, gently pressing, feeling her whole body tighten as an orgasm grew to take her.

Her hands by her sides now hard fists, she lifted her head and wailed out as orgasm claimed her and washed over her whole body, making her shake from head to toe as I kept playing with my fingers inside her. As she came down, I eased my fingers out and lay on top of her, my lips on her neck as she came back.

"Oh god... oh god... I don't know if I've ever cum that hard before... "

I leaned back down to her ear. "Oh, just wait..." I whispered, feeling her moan softly in return.

I gave her a couple of minutes, and then leaned down again. "Ready to turn over?"

"Mmmmm - hmmmm."

I slid off of her, and felt her turn over to her back, rearranging the pillow under her head. She gave me a brilliant smile. "OK! Ready!"

I grinned back. "Feel pretty good?" earning a nod.

With her now on her back, I could now see her body in all its glory. She was gorgeous. Her breasts were just the right size for her and looked remarkably firm, with dark brown nipples that looked like they would be big and solid when erect. The curves of her sides as they met her hips and legs were mesmerizing, and there was not a hint of pubic hair. Wow.

I started with her hand this time, gently massaging it and moving up to her wrist, gently squeezing and holding her Mound of Venus (between thumb and pointer finger) until she visibly flushed and her lips parted. I worked up her forearm, and then her upper arm, reaching her shoulder and gently working the area below her clavicle above her beautiful breasts before working back down her arm to her hand. I switched sides, my still-erect cock crossing her sight line, and started on her other hand and arm.

Once I finished her arm, I started with a gentle touch on the sides of her neck, working down to the start of her cleavage before reversing course, almost feeling her disappointment that I didn't start to play with those beautiful orbs. I worked my way down her sides, across her tummy, and to just above her golden triangle.

Then, and on purpose, I worked down one leg and back up, repeating with the other leg. By now she had relaxed into the experience, and just let herself go. As I reached her feet, I kissed the base of her left foot, letting my mouth wander over to her toes, my tongue lazily flicking over them and feeling her tense. Aha! I ran my tongue along the underside of her toes, and without warning sucked in her big toe and the two next to it, letting my teeth graze the bottom of her toes as my tongue explored them. She started to shake, so I let go and started kissing my way up her calf, then her knee, then her thighs - she knew where this was headed.

But not quite yet - I worked back down her other leg, and then kissed my way up her calf and inner thigh - probably quicker than the first, because I was looking forward to tasting her. She was so smooth she must have had a Brazilian wax, and it made for a delight as I started to tongue and tease her engorged clit. I felt her hands move and take my head, holding on as I circled her clit with my tongue, reveling in her scent and taste, feeling her start to shake again, and then kissing my way up, across her tummy, finally reaching those beautiful breasts, gently lapping a nipple with my tongue, feeling her moan out loud as her nipple popped up. As she moaned, I closed my mouth on her breast and sucked, gently at first, and then harder as she moaned louder and louder.

Mmmmmm - I sucked harder and then gently closed my teeth on her nipple, teasing it back and forth as I felt her start to quake again. I released her nipple and moved to the other, repeating the process, and again feeling her start to quake. I let that glorious breast slip from my mouth and kissed my way up her chest to her neck, up to and over her chin, my mouth now hungrily seeking hers.

Our eyes locked right as our lips met, and I was surprised at how much I wanted her. It was pretty normal to be kissing, but I wasn't used to feeling so passionate. And as we were kissing, her legs wrapped themselves around mine and squeezed, putting my achingly erect cock on top of her tummy.

It was like she hadn't been kissed for real in a long time - and with a start I realized I hadn't either. We kissed hard, our tongues merging, splitting, exploring, and I felt her legs relax slightly and her hand reach down to my cock, tentatively at first, but then gripping it with a strong hand, and felt her guiding me to her drenched sex. Our eyes opened as the tip of my cock felt how slippery she was, and I started to slowly enter her. We kept up our kiss, and I slowly sank myself into her. It was all I could do to not just pile-drive my way in, but going slow was heavenly - and I could tell for her as well. The walls of her pussy gripped me with a purpose, and I could feel her hands on my ass pulling me in as deep as I could go. I felt her start slightly, and realized I had probably brushed her cervix - wow was I in deep!

I slowly started to pull out, leaving just my tip inside her, and then again slowly slid back into her. Our lips parted for a moment, and she nodded at me, her eyes on fire. We did the same slow withdrawal and entry a few more times, and each time we'd both kinda moan - she felt fantastic.

To be honest, sure, I'd been with a number of women, and sex almost always felt great. But there are different levels within great, and Diane was one of those few I'd been with who were in that top tier of ohmigod great. I don't know if we literally just fit well anatomically, or if we were just each others' perfect type, or what, but being with her was just magical.

It was so magical, in fact, that I lost track of everything. I sort of remember rolling over and her being on top, sliding up and down on my cock as I hungrily sucked on her gorgeous breasts. And I think I remember moving to doggy style before putting her back on her stomach and taking her from behind, getting the deepest penetration of her possible.

I do remember our winding up back in missionary, the better to kiss her hard, sliding in and out of her beautiful body, and feeling her start to shake. And I remember her saying in a trembly voice, "I'm... gonna... cum..." and that turning me on even more, impaling her with cock as I felt her orgasm building and building.

And then it hit her so hard she shrieked as the first waves claimed her, a paroxysm of ecstasy washing over her, her pussy spasming on my cock, driving me to the point of no return, me grunting out "I'm... gonna... cum... " and feeling as much as seeing her nod. And with one more spasm of her on me I lost it, and could feel my cum boiling up, racing down my shaft, erupting into her already drenched cunt, painting her cervix white with what felt like ropes of hot, sticky semen, pulse after pulse. Diane would later tell me I actually shouted out as I pumped her full of my cum, and that it was one of the sexiest things she'd ever heard or seen.