My Journey with Heidi Cayne

The first time I saw her was out in the parking lot of our office building. The smooth, bare calves that ended in plain black pumps were what caught my eye. I remember just sitting behind the wheel and watching those legs as she strode towards the building, so business like in her smart navy suit. As I recall, a sharp gust of wind had caught her red hair, momentarily whipping it about her face. In that brief instant I caught a glimpse of slipped composure, of how she might wear a wanton unrestraint and I decided right then and there that I wanted to get to know her better.

Turns out I had to wait a while for my chance. The building I work in houses quite a few companies and so the odds of a chance meeting were not really in my favour. Still I looked out for her, thinking that maybe I'd see her in the parking lot again one morning. I could not get those legs off my mind.

Luckily for me, my moment did finally arrive. However, it came unexpectedly one Saturday afternoon at the Laundromat.

I'm sitting there on a bench, doing my routine two loads and thumbing the papers when in she strolls through the door. I do a double take; I can't believe it's her. She's wearing light blue jeans and a snug in grey t-shirt that exposes a strip of flat tummy that I can't help but eye appreciatively. I glance over my paper, in disbelief, my eyes on the gentle swell of her hips and then on her ass as she passes me by. She leaves a faint trace of floral perfume behind her. She makes her way over to a machine a few drums down from mine and then opens up the door to peer inside. Satisfied, she drops her bag with a thud. The thick stitching of her jeans disappears into her crack as she bends at the waist to fish her clothes out of the duffel on the ground. Instinctively, I search her crotch, trying to discern her panties, the plumpness of her pussy, anything to take away with me. I almost miss the lacy mint green thong when she straightens up and adjusts her jeans.

I watch her stuff her clothes into the machine. A sock escapes her and when she bends quickly to retrieve it, her long, wavy red hair falls into her face. She tosses it back and fingers away the flyaway strands behind her ears. A small grin spreads across my face. It really is her. With growing excitement, I study her as she stuffs the last few pieces into the machine. Her arms are slim and freckled, her legs, long and lean. Curvy hips, splendid ass. And the tits. Oh man, the tits. She pauses. She scans the room and our eyes meet. I nod a detached acknowledgement and then bury my nose in the paper. I haven't quite planned my next move as yet, having been taken so suddenly by surprise. I want this woman's number, but I need to think for a spell. She turns back to the machine. I raise my eyes in time to see her hands disappear under her t-shirt and unhook her bra in the back. She frees her arms and then quickly pulls a worn, lacy blue out bra out of her sleeve. My eyes are fixed on her back as she stuffs it in the machine. I can't wait for her to drop in her soap and coins and then turn back around. I want to check out her nipples; I just know they'll be irresistible.

I look over my paper at her, waiting for the big reveal. Not wanting to be too obvious, I look at her face. Her eyes are turned to the window. She didn't bring any reading material with her. My eyes slowly drift to her chest. I'm not disappointed. I can see that her breasts are round and full, with come get me nipples that poke provocatively at the soft fabric of her shirt. I think I can make out her areolae. They are wide and pronounced. When she gets up to walk over to the window, her tits bounce in such a way that I need to cross my legs for a spell while I think of something to say to her. I swallow and lower my eyes to the paper, racking my brains. She interrupts my thoughts when she leaves the window to come sit right by me.

She mentions the front-page story and seeing a grand opportunity, I seize my chance. We make small talk and I drink her in. At closer range, I can see that she's actually much older than I had originally thought. I decide that she must be at least a good fifteen years older than me, about forty, or so. Damn, she looks good. Her hair is fiery red, with flecks of orange that dance about in the sunlight streaming in through the windows. Her face is small and cute, with a pert, upturned nose and a sweet rosebud mouth. Her creamy complexion is freckled, all the way down to her liberated cleavage. I can't help but wonder how much further down those freckles go, especially when she laughs and her nipples slide against the fabric as her breasts jiggle about. I struggle to look into her pretty blue eyes. I give it up altogether when she bends to pick up the sports section that escaped my grip. She gives me a welcome eyeful. I get to see her soft white breasts, with glorious thick pink nipples in the gaping neckline of her shirt. She straightens up as she hands me the paper and then adjusts her shirt. I can't help but wonder if she did that on purpose. I thank her and ask if she wants to go get some coffee while we wait. We head out the door.

Our coffee break is brief, but charged. I learn she is a new executive, just recently moved into town and not quite settled as yet. She says she'll be starting a new job on Thursday. I don't notice a wedding band. It is really shaping up to be a great day. I listen to her talk. Our conversation flows freely, although admittedly she is doing most of the talking. I don't mind. I get to watch her mouth move and study her dainty hands as she raises her cup to her lips for the occasional sip of coffee. Her lips are soft and pink. She leaves a small smudge of lipstick on her cup. I ask if she smokes. She responds by asking me for a ciggie, as she puts it. I get one from my pocket and carefully light up for her as she holds it in sexy pursed lips. Her lips mesmerize me, just like those legs I keep thinking of that are hidden away in jeans today. Oblivious to the effect she is having on me, her lips seductively puff smoke that curls away and up into air and then into nothingness. Her arms are folded on the table and her breasts are resting on her arms, making her cleavage swell upwards over the neckline of her t-shirt. I can't help but replay in my mind the way she slid that bra off her tits and out that sleeve. Her breasts are free, just on the other side of her cotton t and they sway with the slightest move she makes. I want to suck those nipples till they're tight and shiny through the fabric of her shirt and then take it off so I can taste every delicious freckle I can find on those breasts. She plays with her hair as she talks, twirling it around her fingers. Occasionally, she rests her hand on mine, as though to emphasize a point. I resist the urge to clasp my fingers around hers. I don't want to move too quickly. She asks if I'm married. With a genuine smile that I hope reflects in my eyes as sincere interest, I tell her no, that I'm still looking. I think she likes that. She laces her fingers with mine and laughs. I cave in and squeeze hers back.

We get back to the Laundromat in time to catch the end of her spin cycle. We say our goodbyes and with her number in hand agree to do lunch next Saturday. I get in the car and pause before I drive off, rethinking my fantastic encounter. I look at the precious slip of paper with her name and number. Not only does Heidi Cayne have great handwriting, she also is wonderfully sweet, beautifully poised and confident. I do love an older woman. Plus, she has fantastic tits. Goddamn!

My workweek was hectic, as always. This time, though, my coworkers and I spent most of it tying up loose ends in preparation for a transition to a new team leader. The atmosphere in the office was a little tense, everyone apprehensive of course about what the new leadership would bring. We had a little sendoff for our leaving manager Wednesday evening and came in Thursday bright and early to meet our new boss. Thoughts of Heidi had kept me going through the week. I had called her for the first time on the Monday after our meeting, to let her know in my own way that I was interested and I flirted with her a bit. She was gracious and laughed at my jokes. I'm not particularly smooth with women and as much as women expect you to call, sometimes, a man is not quite sure what it is he should say. Heidi made it easy, though. In the telephone conversations we've had, I've found her to be witty, sensitive yet spirited and feisty. Her voice is soft, but firm; it makes me think of her legs and the way her breasts looked in the gaping neckline of her t-shirt. I now add her nipples and beautiful red hair to the legs that I just can't get of my mind. She is an incredibly smart, sexy woman, who draws me out without dominating me. Her confident demeanor and level headedness is in and of itself and aphrodisiac to me. I can't help but wonder what she'd be like in bed. I've never been with someone that much older, although I must confess, I've fantasized it to death. A beautiful woman, mature and ripe, ready for the picking... makes me so hard just contemplating it.

I did get to see Heidi again that week, but not on Saturday, as we had agreed. We see each other again on Thursday when she walks into my office and one of the higher ups introduces her to me as my new boss. We stand there, stunned in an awkward silence as we are introduced to each other for what is supposed to be the first time. In a silent consensus, we do not let on, but play the game. A stolen moment comes in the afternoon when she calls me into her office for a meeting and asks me to close the door.

She gets up from her desk and leans against it, smiling up into my face. She is impeccably dressed- seemingly untouchable- in an expensive black skirt suit, with a white silk inner blouse, pearls and heels. She wore stockings today. She almost seems a world away from the woman in the Laundromat, but all so familiar to the woman I first cast my eyes upon in the lot some weeks ago. I notice, though that her hair is tied back rather severely and that her makeup is carefully applied. Her gorgeous freckles seem to be missing. I wonder how she pulled that off... She interrupts my thoughts when she grasps my hand in hers. It feels so small and warm. I notice pale pink polish that has been perfectly applied.

Heidi pulls me over to the couch and sits beside me. I speak up first, addressing her as Ms. Cayne. She interrupts me right away, insisting that I call her by her first name. I start again, this time with Heidi. As much as I want to pursue her, I have the good sense to know that this may well be a tricky situation to negotiate and I'm not sure that she would be entirely comfortable with any of it. I state my case as best I can, saying that I do not want in any way to pursue a relationship where she might have misgivings and risk us being the target of office gossip, especially at the start of a new position. I tell her that I think it best, out of my respect for her that we go no further. My cock is screaming you fucking idiot. My mind screams back that reverse psychology might actually work...

She is silent as I speak, looking so deeply into my eyes that I struggle to maintain focus in the depth of those gorgeous baby blues. When I say my piece she still offers nothing. I put my hands on my knees and attempt to stand. Then she leans in and kisses me. When the unexpected softness of her lips brushes mine, I feel my body give in to her. I kiss her back, full and long, darting my tongue into the warmness of her mouth and pulling ever so gently on her lips with mine. We kiss until we are breathless and her hands are in my hair. I pull her so close, that even through the thick fabric of her suit, her breasts are crushed against my chest and I am lost in her perfume. I feel intoxicated by the sudden stolen pleasure of holding her in my arms.

She pulls my hand to her knee. It slips under her skirt and between her thighs. I gingerly trace circles in the silkiness of her stockings before slowly moving upwards until I feel the stockings end and the softness of bare thigh begin. The electric feeling of her bare thighs travels straight to my cock and I feel a throbbing desire for her that only fuels me on. I keep stroking her legs, with my fingertips, slowly inching further still. Her knees loosen to my touch and so, encouraged, I press on to her pussy. I'm so exhilarated that I'm unable to stop. When my fingertips brush the crotch of her panties, she breaks our kiss to gasp. I kiss her neck instead, working my fingers into every fold I could feel through the cotton. Soon her panties are sliding under my fingers and just knowing how wet she is and hearing her moan softly against my ear makes me want to take my cock out and slip it inside her.

I am so hard that I can barely stand it. I want Heidi so badly, I'm willing to risk it right here in the office, with everyone outside, as crazy as it sounds. I pull her hand to my crotch and she doesn't waste a moment unzippering me before maneuvering me out of my fly. My cock is standing straight up in front of me, in the palm of her hand, so hard and damp from precum glistening at the tip. I'm torn; I know that we could be discovered at any moment. Heidi breaks my thoughts when she slips to her knees and puts my cock in her mouth. I groan aloud then. I can't help but surrender to the glorious feeling of her lips sliding up and down the length of my cock and back again. I look at this splendidly dressed woman on her knees in front of me sucking my cock. Heidi licks at the head, with the soft tip of her tongue before taking lingering sucks that make soft smacking sounds the second her lips disconnect from my shaft. I groan her name, knowing full well that if she keeps this up, I'll jizz- jizz so hard, that I don't know if I'll be able to pull out of her mouth in time.

With a quick glance at the door, I pull Heidi to her feet and lay her down on the couch. I just have to fondle her breasts. I unbutton her jacket and she drops it on the ground. She undoes the blouse herself. She's wearing a plain sheer beige bra that lets me see her nipples and areolae very clearly. I clamp my lips over a pink nipple and suck at it through the fabric of her bra. I push her breasts together and run my tongue from one to the next as I knead the softness of her large, pillowy, freckled breasts until they spill out of the cups. She's moaning and tossing her head side to side, so much so, that she's managed to undo her bun. She looks wanton under me, just as I had imagined she would be that first day out in the lot. And I want to fuck her like this, with her hair spilled across her face.

I push her skirt up over her hips and pull her cotton white panties down. I take them off, carefully negotiating her heels, before pressing them to my face and throwing them aside. Heidi's pussy is as lush and red as her head, only with a few strands of grey. I take a leg in each hand, standing in the middle of her. She smiles up at me. She is a sight to behold: stockinged legs sprawled east and west, with a wet ginger pussy in between. Her blouse, although still on, is open to reveal breasts that have tumbled out of her bra and that are hiked up under her chin. Her pearls are high and disordered about her neck.

I need to take her now. Still holding her legs, I nuzzle my cock at her wet entrance. Heidi's pussy is fleshy and full, so much so that her inner lips spill out of the outer ones in a pink, meaty pout. I ease my cock into her entrance and watch those thick inner lips swallow up the head of my cock. I want her so badly, but in spite of knowing we may be discovered, I still don't want to rush it. I want to savour this moment and revel in Heidi's reaction to my touch and my cock. I want her to quiver under me and surrender to every conquering stroke.

I make love to her in tender, deep passes feeling her pussy contract appreciatively around me. She reaches up and puts her arms around my neck, drawing me in for a kiss. I lie flat on top of her, probing her pussy ever so slowly. I ride her high, so that I can grind her clit and hopefully make her come something fierce. Her head is cradled in my hands and I kiss her deeply, occasionally reaching down to pop a nipple in my mouth. She seems to like nipple play. I bear down on one, licking and sucking, twisting it with my tongue until she undulates her hips under mine. It makes her come quickly in a hot, trembling silence. She laps her long legs around me and squeezes my waist. As soon as she is still, I am finally free to make the few feverish thrusts I've been desperate to take. I take her legs into the crook of my elbows and feverishly fuck her till I crash over the edge. I pull out and squirt hard onto her red pubes, rubbing my cock in her thick curly hair.

We are breathless, but blissfully consummated. I know there's no turning back now- I like Heidi way too much for that. I'm hoping that we're onto the beginning of something here. I want adventures with Heidi. I tell her as much and she kisses me again with a small twinkle in her eye, as she lights up a cigarette. We straighten up and I leave her office. No one notices a thing; our meeting took all of half an hour, or so. As I settle at my desk, trying to come down from an unbelievable high, I realize that Heidi didn't say a single word- except to insist that we remain on a first name basis- the entire time I was in her office. I begin to wonder if I've been had. A smile spreads across my face.

I don't see Heidi on Friday. She calls to tell me that she'll be away on business, but that she is very much looking forward to our lunch date on Saturday. I plan to take her to a quiet little restaurant by the canal. It'll be picturesque there, but nothing too intimate. I know we're already taken the ultimate step, but I don't want to send a message that's too heavy or deep. I've only known her a week, after all.

She arrives at the restaurant about ten minutes after I do in a girly floral print cotton dress and matching pink sandals. Her loose hair is kept in place by a silver hair band. There's not a trace of make up in sight. I'm happy that her freckles have made a comeback and that her breasts are peeking out today. I rise to greet her and she kisses me hello. I hold out her chair so that she can sit. We order and sip cokes making small talk till our food arrives. Heidi plays with her straw as she looks at me and I can't help but remember the sight of her with my cock in her hand. I tell her I've missed her. She tells me she's been looking forward to this afternoon so much and that she hopes she will be able to spend more time with me in the future. I tell her that I'd like that. That I'd really like that a lot. With a grin, she tells me I'm a messy eater, that I've got ketchup on my finger. Before I can wipe it off with my napkin, she pops my finger into her mouth. I call for the check and we head for my car.

I ask her place or mine. She says mine. I press the accelerator. Heidi's hand is on my thigh. My cock is already hard. She leans over to kiss my neck. I feel her tugging at my zipper. I help her out as best I can struggling to keep my eyes and concentration fixed on the road. I feel her take my cock out with some difficulty. I wince a little, as it's so stiff it won't bend out of my fly. When I'm finally free, the next thing I feel is the enveloping warmth of Heidi's wet mouth. I glance down to see a lapful of red curls bobbing up and down on my cock. Her tongue is so deft that it makes me want to shoot my load right then and there into the back of her throat. I don't know that I'd be able to pull away for this one. I can't make it home. I pull off the road onto a quiet side street.

I'm hoping the tint on my van's windows is dark enough to protect our modesty. I watch her suck my cock. Her pretty lips are wet with saliva and my juices. She sucks me without a hint of shyness, something I'm unaccustomed to with the other women I've been with. I'm getting off on her enthusiasm, as well as her seasoned skill. She sucks cock like a pro. My fingers get lost in her hair as I hold on for dear life. The ride is exhilarating. Heidi brings me up to the point where I'm about to climax and holds me there with tongue flicks all over the head of my cock. Trembling, I struggle to push my entire length into her mouth, arching up to her, desperately trying to get myself off. I struggle to temper my desire so that I'm not too rough with her. I want to come so badly. Some agonizing moments later, Heidi closes her lips around the head of my cock and presses it with her tongue to the roof of her mouth. I tell her I'm coming. She doesn't pull away. I pull back my hips and thrust as deeply as I can. I shoot my come into the back of her throat, my hips in a frenzy, as she sucks me off. The pleasure of coming in a woman's mouth is not one that I have experienced before. My head is swimming. The ecstasy of having the come sucked out of me is indescribable and I cry out loud.