by Ruby Madden
Having found her on an online hook-up site had been purely coincidental. I’d decided to cancel them all, the ones I’d used to troll for sex. I hadn’t expected the very intelligent and smart message from her. So, I’d kept the account open. All the others were closed. Gone, forever.
We’d been messaging back and forth for a few weeks now.
We hadn’t met in person. Yet.
Or web-cammed. Yet.
Secretly, I was both terrified and thrilled that I may or may not have what it took to enthrall her. To pull her in and to pull her out of herself.
Stuck in my thoughts, I hadn’t noticed that an hour had passed and was suddenly semi-startled by Kayla’s warm, tan, thin arms wrapping around me from behind and nuzzling her face into my neck and shoulders.
“Good morning sexy…” She murmured into my ear, her hot breath delighting me.
I somehow manage to close my laptop without her noticing, I hope, the website on my browser.
“Good morning. You’re up early.” I say softly. I was selfish in that I was relying on her usual behavior, to sleep in late. I wasn’t quite ready to interact with and entertain her – just yet.
I wasn’t even sure why I’d called her last night myself. Some habits die hard, I guess. I was feeling lonely and frisky, stirred by the recent interactions with SF49girl.
“What’s on the agenda today?” She purrs into my ear like a cat.
“I’ve got practice to go to in a bit.” I lie.
“Practice?” She says, puzzled, standing up straight and releasing me. “I thought you were retired now, Ryan?”
“I am, but I still have events to go to and such. Have to keep in shape. You know how it goes.” I say casually, hoping she doesn’t see right through my white lie. Secretly, I feel bad. I don’t want to lie to Kayla. She’s a neat girl. But she’s not a woman. Not what I really want and need, anymore.
Still, it was bad that I’d invited her over for casual sex.
I’m an ass-hat, clearly.
I don’t have the opportunity to do right by her as she storms back into my bedroom and I can hear her angrily and quickly getting dressed. Then, gathering up her purse and keys. She storms through the kitchen on her way to my front door.
I watch helplessly by, annoyed with myself. I never was a good liar.
“Kayla…” I attempt the start to some apology she’ll never hear as she is already halfway out the door and muttering loudly, “Ryan, you’re an asshole. Fuck you!”
On that point, I have to agree with her.
Grover barks back, alarmed at her raised voice and the door slamming shut loudly.
I scruff him behind the ears, “Its okay buddy. I deserved that.”
He tilts his head at me and gives me one of those adorable looks. He understands me best. He truly does.
{ HARRY }
I took a sip of my coffee, watching Cassandra stride across the marble-floored entry, her heels clicking commandingly as she walked. For such a petite woman, she sure had presence.
Her dark bob was perfectly in place, something of a miracle given how windy San Francisco can be, even on a good day. She was wearing a violet colored ensemble that flattered her. I gazed at her perky, firm ass in the skirt that was cut just above her knees. Her sweetly contoured legs ending in pair of casual, chic, designer shoes that probably cost a small fortune.
I loved everything about her. Her personality, her wardrobe, her stature, and the commanding way she met business head on. Her finesse, and most of all… her eternal frustration with me.
I’d been playing this game for a while with her and I wasn’t so sure she’d caught on. Despite what Cassandra thought, I was her biggest admirer.
Pretending otherwise.
I’d never been very good at flirting, so I’d learned a different approach with the ladies. Sometimes, it worked. Sometimes, it didn’t. I wasn’t too proud to know when I’d lost.
Cassandra, though – was worth persistence. Yes, she was older than me and I knew making a good impression on her would be difficult. So, I’d decided to make a lasting one instead. I realized that to keep her in the foremost of her mind, I’d need to irk her, near constantly. Until one day, I’d do what needed to be done. Confront her and this unmistakable attraction between us.
Time to man up. At least, my version of it, for now.
Until she called me on it. A day I was eagerly anticipating…
I zipped through the busy lobby entry, just in time to squeeze into the same elevator she’d gotten on. Casually, I feigned noticing her.
“Ready for the day?” I asked, perhaps a bit too stern.
As usual, she peered at me disdainfully, a semi-scowl on her face. “Always. Good morning Harry.” She answered, then took a sip of her own coffee.
“Getting enough sleep?” I asked.
“Yes, why?” She responded, a nearly complete scowl on her face.
“Nothing, just you look a bit tired.” I remarked casually.
“I do?” She stated.
I had to hold my grin back. I’d already ruffled her feathers and she hadn’t even made it through the entry of our office. Somehow, when she looked near-furious, I was the most aroused by her.
“Sorry, just an observation. Not a judgment.” I began my fake polite retreat. She is still one of the bosses after-all. I can only get so close to the edge before just seeming out and out rude.
“Well, Harry. In this company, Directors and VP’s often forfeit sleep. Do you think you’re prepared to give up some shut-eye on occasion?” She taunted.
I heard Rachel, the blond receptionist who also happened to be in the same elevator with us, attempt to stifle a snort-chortle. She hid it by quickly taking a sip from her coffee canister and looking away. The amused look on her face clearly showed that she was on Cassandra’s side.
I decided to stay mum the rest of the way up as others exited the elevator. Being near the top floor had its perks and minuses. One minus was that the elevator ride up was always a bit long, despite the fact that we by-passed the first forty stories altogether in this, dedicated elevator to the top floors of the building.
When the elevator doors pinged open, Cassandra was quick to exit, the click-clack of her shoes revealing how fast she wanted to get away from me.
Rachel however, exited slowly, while shaking her head. “Ryan, Ryan… One of these days, she’s going to figure you out and what you’re up to.”
I blinked and cocked my head to the side. Rachel was smarter than she looked. As if to confirm my thoughts, she continued.
“Degree in Behavioral Psychology. Not just a receptionist.” She said, then winked and strolled away to start her day being commander of the busy phone and reception area. Her partner-in-crime, Allyson, already chirping out hello’s and welcomes to the calls pouring in.
It’s true, a bachelor degree in psychology rarely gets you anywhere in this town. It takes the next step, the next level. She was probably saving money, paying off a student loan or both. Either way, she was smarter than I’d realized. I hated it when I underestimated people.
Mental note to self, time to ask Rachel out for lunch. And… time to get to work.
{ CASSANDRA }
Home from work, I was sitting in my PJ’s on my sofa, laptop on my lap and peering at Ryan’s pics again. My fingers flew across the keyboard.
Me: If I were to masturbate, while thinking of you, your face and that sexy bod… what would you hope I’d do to enjoy myself? Thoughtful response, please. This will actually happen when I get a reply…
I included a picture of my toy-box, a beautiful hand-carved wooden piece that I’d been given as a gift in India while there for business.
I’m sure they had no idea what good use I would put it to when I returned home. The executive who’d given it to me had explained that the type of wood it was made from benefited from being touched and caressed by human hands as the oil from the skin helped to maintai
n the color and texture of the wood over time. He had rubbed his hand over the lid, while smiling at me.
The gesture was sincere and innocent. True gratitude for the contract I’d helped them with which meant more business to their company than they’d dare dreamed possible.
I’d smiled and known instantly what I would use it for. Of course, he thought I would use it for something far less naughty and imaginative. Say, for tea. And although tea bags would look absolutely scrumptious in just such a container, my collection of sex-toys would look better.
I love my sex-toy collection.
I invested in my toys like anything else, with a lot of thought and with a goal of acquiring the best. This meant designs that were both useful, practical and elegant. Materials that would last with proper care and were ‘insertion-friendly’. Toys that had aesthetic appeal, excellent functional purpose, and made sex-play with new lovers even more fun.
Men’s reactions to my Toy Box ranged from enthusiastic delight to offended confusion. It just depended on their exposure, curiosity and experience.
Those who found it offensive were usually guilty of automatically assuming that a woman can orgasm solely from penetration alone. Some women do, but most don’t.
Those were the ones I either chose to enlighten and teach so that no more women suffered under their delusion. Or, I’d make them watch me use my toys on myself so that they could see why a woman needed a lot more than just their cock to get herself off. Eventually, if they proved to be quick learners and attentive, I’d have them use them on me.
Those who delighted in my collection were always eager to play and try. The combinations were never-ending. It had started innocently enough. At the time, I was in my mid-twenties and had a lover whose moves were great and his body was hot, his imagination never-ending but his cock was less than average.
Unfortunately, it left me ‘wanting’.
So, I snuck a decent-sized dildo into one of our fuck-fests and he loved it. I remember his eyes getting big and the carnal giggle that came out of him when he first pushed the generous toy into me. Then he got more aggressive with it and pumped me, opening me up. I came like mad as I applied a buzzing vibrator to my clit. My pussy gripped down on the filling dildo and I screamed myself nearly hoarse.
He’d been insecure about asking me himself, he’d later confess. I made sure he knew that I found him to be a good lover, but that for some women, the sensation of a large cock is very satisfying and pleasurable.
Educating lovers about a woman, her body, her desires, wants and needs came naturally to me. I went about it in a manner that was natural, organic if you will. I didn’t want to sound like a sex educator or some dated instructor. I learned how to explain, share, and reveal like a magician and all their tricks.
Over time, I realized how little most men really knew. Their worst fear, besides being unable to get it up or satisfy a woman, is to be found wanting in how to please and perform. I realized it required two things, experience and practice. Lots of practice. Most were earnestly interested in becoming better lovers, it just required frank talk and guidance. Eventually that interest would become eagerness with time.
Once they had plenty of practice with me, I was usually ready to move on and would gently release them into the world to hopefully make another woman happy, satisfied and pleased.
I was rolling through my Netflix queue looking for something to watch when a response popped up on my computer screen. I clicked on it, anticipating what he typed.
Him: ‘Goodness, how can I compete with such a fun and I’m sure, pleasurable collection?! :P’
I laughed out loud at his response. I liked him even more. Playful. My favorite.
Me: ‘Well, the real thing is always the best, especially if a man knows how to use his tool.’
Him: ‘I like to think I do…’
Me: ‘Tell me about these moves, Mister…’ I knew I was taunting him. Toying.
Him: ‘Do you web-cam?’
Me: ‘Sometimes…’
Him: ‘How about we try it. If you don’t like it, we can just chat?’
Me: ‘I’m already in my PJ’s, lounging on the sofa for the night… Not very sexy.’
Him: ‘And where do you think I’m at? Although I’m not in my PJ’s. But then, I sleep in the nude. I could change into my B-day suit if you like?’
Me: ‘Just a sec…’
I paused and set my laptop aside. I strode to my freezer and pulled out some Haagen-Dazs ice cream. I turned on the kitchen faucet and waited for it to stream warm water. Once it was, I warmed up my ice cream scoop and took down a bowl from my cupboard.
I was contemplating.
It was my experience that if you engage a man online with the web-cam, you’ll very rarely succeed at getting him in the bedroom with you, even if he lives right next door. Men get a lot more from web-cam sessions than most women.
They’re satisfied, I’m usually not.
However, we did have the living in different parts of the state thing to consider. In one sense, this was the best we could do for each other, for now.
Done scooping up a decent serving, I put away the ice cream and went back to my cozy spot on my sofa. I prepared myself for a web-cam session, attempting to look my best.
I turned on the web-cam and beamed a sexy, naughty smile into the computer screen.
Him: ‘Why hello lovely…’
Me: ‘Same to you.’ I was soon admiring his handsome, boyish face and his nude chest and torso. His brown eyes were warm, like his smile. He had a bit of day-old stubble. Scruffy but sexy.
Him: ‘What’cha munching on there?’
Me: ‘Ice cream…’ I made a point of taking a bite and as I pulled the spoon out of my mouth, I took my time sucking the rest of the ice cream off of it.
Him: ‘Damn! Eating ice cream has never looked so good.’
Me: ‘I’m an indulgent creature. I like to enjoy myself. Head to toe.’
Him: ‘Such a sexy lady. Will it bother you if I touch my cock while we web-cam?’
Me: ‘Such a gentleman. Please, be my guest.’
I was flirting coyly, shamelessly at this point. One of the things I enjoyed best about the online interaction is that I could be so brazen, behaving like a little sex-slut toy. I mean, the man was hundreds of miles away. It was safe. He didn’t know my real name, what part of the city I lived in, where I worked, whether I was truly single or married. Nothing. All he knew was what I chose to share or reveal to him.
Speaking of revealing… His next IM pleased me.
Him: ‘Show me how much you enjoy your ice cream.’
I perked up. I liked the direct, commanding request. I felt the heat go straight to my groin.
Me: ‘Be imaginative. Tell me how you want me to enjoy it.’
He didn’t miss a beat, his next request floored me.
Him: ‘Put the spoon in your ice cream, get it good and cold, and rub it on your nipple.’
I’m sure he noticed my pleasantly shocked surprise. I was frozen for a brief moment but found myself doing exactly as he asked.
I pulled one of my full breasts out, completely exposing my tit to him. I dipped my spoon into my ice cream bowl and let it get chilly. I licked the side that had ice cream on it, enjoying the creamy goodness. I then slowly applied the still chilled side to my nipple.
The zing went straight through me. My nipple was hard instantly.
Him: ‘Gaaawwwd… so sexy. Do it again. With the other one. Pull them both out for me.’
I pulled out my other breast, each of them perked up with my hard nipples. I languished a bit while I chilled my spoon again, allowing him a good amount of time to stare at my tits. I repeated the same thing with my other breast and this time, my eyes rolled back.
So simple. So hot. I was already completely aroused. I wondered if he could tell.
Him: ‘Go get your toy-box, the one you sent me a pic of.’
I put my laptop to the side and walked quickly to my bedroom. I pulled out my toy box and brought it out and sat it next to me. I settled back on the sofa and put my laptop back on my lap. My tits were still out and exposed, the cool air had given them a tingling sensation while I walked.
I didn’t say anything, just waited for him to acknowledge me again.
Him: ‘Good girl. I noticed a pair of chain nipple clamps in the pic. Put those on for me.’
I reached into my toy box and pulled them out. My pussy was getting creamy and wet at this point. I seductively clipped each of my nipples, relishing in the deliciousness of the cold steel metal clasping my very alert nipples into a perma-grip that would keep my breasts aroused for the remainder of our playtime.
Him: ‘Pull the chain up into your mouth and tug on those gorgeous nips of yours…’
I did and the sensation pulled out a breathy moan from me. My eyes fluttered shut for a moment.
Him: ‘Open your eyes… I want you to see what you’ve done to me.’
His erect manhood was on display. That gorgeous, perfect, sexy cock. One in a million. Serious. He had a nice grip on it and was pumping himself gently, slowly.
I whimpered. He noticed.
Him: ‘I like the size and shape of the purple dildo in your toy box. Pull it out for me.’
I pulled it out. I was on the precipice of wondering what he would ask me to do next. I grinned coyly into my webcam, waiting… He made me watch him for a while. I wanted to lick his cock-head. For now, all I could do was salivate.
Him: ‘Take off your PJ bottoms. Do it sexy-like, baby-girl. Shimmy. Make sure that webcam lets me see the goods.’
I stood and figured out what would work best for a strip-tease. As I hooked my thumbs into the side loops of my PJ bottoms, and shimmied out of them, I swiveled my hip in one continuous move and back. Suggestive and curvy. I was glad I’d chosen a sexy black thong to wear. I’d learned to anticipate evening play with most of my online suitors. I teased him a bit, bent over and gave him the money, stripper shot. Full on pussy, still covered in sexy material. I knew I was wet. I wondered if he could tell?
