As in many companies, and even socially, instant messaging has become a popular way of communicating. And for someone like me, that spent HOURS upon HOURS chatting online when it FIRST became available back in the 90′s…late into the night for many, many nights, I love IM.
Of course, those many hours and many nights were spent chatting about sex. I took pride in not just enjoying being an anonymous perv, but also being a good wordsmith and impressing the right woman in a private chat after meeting in some dirty chat room. And if I was really lucky, that turned into phone sex…and it did quite often. At least that comforted me in knowing it wasn’t a guy I was chatting with!
Anyhow, I digress.
I find it much easier to flirt over an IM, as most people probably do, and I got very excited when I would find someone at work, who was willing to partake in a little off color back and forth. And trust me, in a work environment, you have to be VERY careful and always let them lead the way so you don’t go to far with your comments or too far too fast. I found a few women at this particular job that turned into some great real life experiences. Well, two of three did. Why I didn’t jump on the third, I’ll never fucking know…because she was ripe for the taking. She basically was offering herself up to me and I didn’t do it. Oh well, 2 out of 3 ain’t bad! 
This particular woman was a surprise to me because I really hadn’t thought she even looked at me in that light (not that I think most women do, but…). We innocently exchanged some funnies back and forth as we flirted and something slipped out a little more serious about kissing one day. If I remember correctly, we got on the conversation of kissing. Describing what goes into a good kiss, if we thought were each good kissers (of course we both thought we were good), etc. And so, what good is talk if we didn’t test each other, right? Nothing like “prove it to me” to get you moving!
So, she came into my office and shut the door. I always kept the blinds closed, that way there was only one thing to close and it looked less suspicious. Without saying a word, I stood up, walked up to her and pinned her against the back of the door. She gasped. I could feel the butterflies in my stomach and the stirring in my pants. I slid my hand up her side and up along her face and then around to the back of her neck, pushing her long, straight blonde hair back, grabbing her by the base of her hair firmly but not too hard. While I pressed my body against hers, staring into her eyes, I pulled her head toward me and lips onto mine. Turning my head slightly, opposite of hers, and as I saw her eyes close, so did mine. Our lips pressing against each other. Our mouths just barely open, she moans and lets out a big breath before we both slide our tongues together and lock our lips. Both of us with full, soft lips and warm, wet tongues. We kissed with a gentleness at first and as I grasped her hair and neck a bit firmer (and as my cock grew firmer), we kissed harder and more feverishly.
As I pulled back slowly, our lips sticking together before giving way, both of us breathing hard. She leaned her forehead against mine and said through her whispery breath, “you were right!” and I immediately replied, “and YOU were right!”
Needless to say, we had this encounter quite a few times in my office and in other places we could escape to. And also needless to say, our IM conversations QUICKLY became hotter, raunchier, more graphic and it wasn’t long before we were working on plans to take this to the next level. To THE level. We needed to fuck each other BADLY! One thing I could not convince her to do was to do it right there in my office. She was too afraid of getting caught. As much as I wanted to tell her that I hadn’t been caught before (with another), I didn’t want to ruin my shot of having her at all.
While we spent many days racking our brains about it…since she was married and I was living with someone, I finally saw an opening. I had the fortune of being chosen to tour a new cruise ship since I worked in a marketing capacity for a travel company. I was going to fly to San Fransisco and spend two nights on the ship – alone. I thought it would be perfect for her to go with me. But the problem with that was I was not allowed to bring a guest and I would have had to convince the company to send her with me. That was NOT going to happen!
So, my plan was to go on the trip (or at least the flight to SF), have her fly there too and instead of going on the ship, rent a car, head to Napa Valley, get a room and BINGO! We could go on wine tours, get toasted and fuck, suck and scream for two days! It was just crazy enough to work. And it did!
We got to Napa mid-day and believe or not, we did go to lunch first. Remarkable, I know. After checking into our room though, there was no more waiting. No more planning, wishing or scheming.
While that first time together WAS great…I want to detail one of the evenings we had. We ate a romantic dinner at a Chop House and shared a couple of bottles of wine. Of course dinner consisted of plenty of flirting, touching and teasing. Back at the hotel, we sat in the car before going in and did what started all this (kissing) long enough to heavily steam up the windows. I knew that was the sign to get inside.
Once there, she immediately starts to remove her clothing, but I stop her and lay her down on the bed. I remain standing and grab her left leg, lifting it up to remove her black high heel. Then the other leg and heel. She squirms as she watches me through drunk eyes. I step closer and bring her right leg against me and hold her foot right in front me, my breath against it. I lean down and start to lick her toes before sucking each one slowly into my mouth. One at a time. Her low groans and gasps of this unexpected move tells me she loves it. I suck, nibble my way form one toe to the next and from one foot to the other.
She’s wearing a black miniskirt, giving me easy access to move From her foot and up her leg, although, technically, I am licking, nibbling and sucking my way DOWN the back of her leg with her foot up in the air. I grab both of her legs, holding them up as I work my way down, eventually kneeling on the floor at the edge of the bed. She has already wedged her skirt up, exposing the very large wet spot on her pink panties. Her aroma fills my nose as my tongue slides along the edge her panties, along her ass cheek. She grabs her legs and pulls them back and far apart, freeing my hands up. I grab her panties and wad them up together, forcing them tight against her pussy lips, even between them, exposing most of her lips for me to lick. And from her exposed lips, I suck her panties against her soaked, very hot pussy.
Her moans and heavy breathing grow louder. I slide a finger under the panties right into her. She arches her back and yells aloud! Forcing her panties to the side more, I slide a 2nd finger into her tight pussy and she screams, “FUCK!!!” followed by my tongue landing on her aching clit. My fingers curl up slight inside of her and push deep, almost lifting her small ass up as I begin to devour her clit. Her body starts to shake and convulse immediately. Almost completely out of breath, gasping as she tries to yell out to me that she is cumming; almost thrashing as she grabs my hair and head and tenses up completely.
Stops moving. Holding me so tight and still.
No breath.
She collapses, exhaling out with a throaty moan. Her pussy is white with cum, actually throbbing and dripping all over my fingers and face.
“I came so fucking hard!” she whispers as she tries to catch her breath. Followed by, “I need your fucking cock…NOW!” in a not-so-whispery voice. Who am I to not give her such a treat? But how? I think to myself. Mmmm, my favorite position (which I honestly didn’t know the “name” of it until recently)…the reverse cowgirl. Me on my back, her straddling my cock, facing my feet.
I tell her what I want and she immediately obliges. We both strip down completely. I lay back on the bed and she straddles me, facing my feet, guiding my cock into that heaven of a pussy. I moan loud as she pushes herself back and down my throbbing cock. Her perfect, tan ass is a beautiful sight as her pussy eats up my thick cock. She fucked me hard and fast, with a slow grind, leaning all the way forward and leaning all the way back, finding many angles of hitting her deep with my cock.
It was when she told me to spread my legs wide and she knelt between them, bent over, pushing back and down my cock that did me in. She reached down between her legs and mine and played with my ass before sliding a finger into it. My cock almost instantly exploded. She held her finger inside me as she circled her hips and fucked my cock.
My breath quickened, “oh fuck, I’m gonna cum!” She pulled out my cock and layed it on the crack her ass, stroking it. My body jerked hard as I let out a loud moan and shot streams of hot cum onto her asshole and up and down her the crack of her ass. She backed herself up my body, so her ass is right over my face and squatted over my mouth, letting my cum drip onto me. I grabbed her ass and pulled it down, licking my hot cum off her asshole and crack. I slipped a finger into her ass and she moaned…
“I bet I can get that cock hard again for THAT hole…”
“Challenge accepted” I replied.
Do I write a 2nd story about THAT? We’ll see.
