Marty-Always Smiling

When I got into MBA school, I was required to take some undergrad courses since I had been a non-business undergraduate major. In the accounting class, I met Marty, a late 40s mother of two divorced from an eye surgeon. I was 27. She had never worked and was going back to college to get her BA, had kids in their early 20s, and apparently made out very well in the divorce--had a big fine, paid-for house, drove a top-end Benz, and groomed and dressed impeccably.

Very assertive and sociable, she was an accomplished "networker," and could meet and impress 20 people in a single hour, as I had observed between classes. She was very smart, too--made straight As--and really enterprising, as well--taking most of the divorce settlement and investing it in houses that she leased. She already had like 6 or 8 and was buying more.

Her looks: The first thing you'd notice about Marty was her smile, full upper and lower lips, wide and friendly with large, fairly straight, porcelain-white teeth, and she was always smiling, always. The lines in her face sent a message of "interesting woman" rather than "lady getting on up there." Her emerald-green eyes sparkled over high cheek bones, and though she wore lots of make-up, she always looked like a Hollywood make-up artist had applied it, and the shade of her lipstick was always a perfect match with the polish on her professionally manicured nails.

Auburn with just a tinge of red (probably colored, but who cares?), her wavy hair was styled immaculately in a simple but appealing swept-back, medium volume fashion to just below her shoulders. She stood about 5' 5" in heels and had a classic 1940s "hourglass figure," but, even so, the expensive, "all-business" but not masculine style clothes she wore did not bring attention to her physique.

Overall, her appearance telegraphed utterly together and professional. But more on her looks later.

Her home-leasing enterprise is how I really got to know her. She'd buy the houses cheap because they needed repairs, and could charge high rent because they were in nice neighborhoods in the 'burbs, but needed to fix them up in order to do so. I had a home restoration business at the time which focused on renovating early-1900s inner-city homes. Though it was not my market niche, she asked me to give her an estimate on fixing up a home that she had just bought and was anxious to get leased in a hurry to turn the cash flow positive.

So I took a look at it, and it needed painting inside, carpeting, new linoleum in the kitchen and baths, some ceiling repairs, windows caulked--easy stuff--and, of course, it was vacant--fast work. I gave her my pretty high estimate, which she tried to negotiate down, but I held my ground and promised I could finish it in a week, so she said OK. I finished the job a day early and she was very pleased with the work and paid in cash.

I went to her own fabulous home one evening to drop off some supplies for a new house near her that she had bought but not yet taken possession of. As she gave me the grand tour of her place, I noted that all her stuff was only the best of the best--Persian rugs, antique furnishings, Lalique crystal, Yamaha stereo, Bosendorfer baby grand piano--the works.

She said she had not had dinner, asked if I'd eaten yet, which I hadn't, so she ordered some delivery Chinese and uncorked what I figured was an astronomically expensive bottle of 1957 Chateau Rothchild before we sat down to sip it and wait for the food to arrive. She was a great conversationalist and very interesting. She showed me lots of pictures of her son and daughter, who looked like Miss America, and told me she was single, not dating anyone at the time, and would be home from college for Christmas break the following week.

Really? Those pool party photos certainly placed her as a finalist in the swimsuit competition, and the sorority dance pics of her in that plunging v-neck black dress already had me puckering for her ample breasts. Then Marty said she thought her daughter and I would really like each other. So at this point, I figured Marty was laying the groundwork for a little get-together with her superb daughter, whose bones I had already decided would be appropriate to jump on our second date.

The bottle empty, Marty produced a second of the same vintage just as the Chinese food arrived. We ate the spring rolls, hot-and-sour soup, and moved on to the garlic beef as we talk, talk, talked.

We covered many topics, but then she asked if I thought she had a sexy voice. In truth, since we had a business/academic relationship, I'd never really thought about it, and I was surprised that she asked me such a thing, having sized her up as really quite conservative. Come to think about it, she did have an extremely sexy voice--low and husky with a refined Southern accent--so I told her, "yeah." Then I changed the subject back to her daughter, who currently occupied my interest as a most devine repository of my spermatazoa.

Marty said everyone thought she and her daughter bore a strong resemblance, that they had won some mother-daughter look-a-like contest the year before. Well, upon consideration, looking again at the pictures in the album, Marty and her daughter DID look very similar, remarkably so. Pointing at a large, full-length photo of her daughter, Marty proceeded to cover their similarities feature by feature: eyes, nose, mouth, ears, cheeks, chin, and "figure," which she stood up to model, quickly smoothing her perfectly manicured hands across her bustline, down her narrow waist, and around her hips.

Though I had always regarded Marty as an attractive older woman, I was now, for the first time, thinking of her differently, somewhat sexy. Marty was effectively transferring my interest from her daughter to her.

Then Marty told me why she had asked me about her voice, couching it as a secret I must promise not to tell. My interest was piqued, and I swore I would not tell. She said she made erotic tapes! Now, this was like hearing that Madeline Albright chews tobacco--totally out of character.

Marty told the entire story of how she'd gotten involved by simply answering the phone one day, and the guy on the other end had told her what a sexy voice she had, and then referred her to someone else, who, in turn, referred her to yet another person, a woman who owned the company who explained to Marty the business, what would be required of her, and how much money she could make--a lot.

Wow, erotic tapes, huh? What kind of erotic tapes, I asked. She asked me if I would like to hear one. Well, I guess I did. So she went into the other room and returned with a small (naturally high-end) tape player and handed it to me. Apparently, I would have to be the one to press play, so, after a moment of hesitation, I did. Long pause, then clearly Marty's voice.

To listen to Marty's recorded voice and not associate it with her, it sounded like a much younger woman. I don't remember the exact wording, but the first part of the tape was fairly mild, though alluring, and went something like this:

"Hi, my name is Vanessa, and I'm a 23-year-old blonde swimsuit model. I got into it because I've always liked to swim, to feel the water coursing over my body. I used to swim on my high school team and usually won races, so I went to college on a scholarship. But the competition there was a lot tougher, and I often didn't win.

Though I'm athletic and slender, my coach said it was because of my build. You see, my breasts are too big; they measure 36D even when I pull the tape real tight around them. I met some people at a meet who wanted to take some pictures of me in their company's swimsuits, so I gave it a try and got the job. I'd always enjoyed the way guys would look at me in my own bikinis, so it was really easy to pose for the photos in front of the mostly male crew.

The problem was, some of the company's suits were a lot skimpier than my own and showed my tan lines, so I started laying out nude. Since my hair would poke out of the tiny bottoms, I also had to start shaving completely bare, if you know what I mean.

To keep my tan, I take my lunch out on my deck at midday when it's sunny and lay out naked for an hour or so. Sometimes I catch the neighbor guys checking me out, and it kinda gives me a rush knowing they are staring at me, but I just pretend I don't notice. Once in a while, I'll even put on a little show. I'll squirt lots of oil all over me and rub it on my bottom, squeezing my firm little buns. Then I'll massage the oil into my breasts and pull on my nipples until they get real pointy, which feels really good."

I stopped the tape, and Marty asked me what I thought. I told her it, was, well, erotic, that her voice was a natural, but that I was frankly surprised that she was involved in such a thing. She said that was because I had only seen her "public" persona, that there was another side to her, looking back at me sexier than ever. She pressed the play button.

"I don't know why, maybe because I don't have time for a boyfriend, but I'm getting bolder. A few weeks ago, after I had been lying there a while in the warm rays, I just couldn't get my mind off of sex. I hate it when that happens! I turned over and was rubbing some oil on my belly when it ran out of my belly button, which is deeper than most skinny girls', and the oil ran out of it onto my bare privates as I sat up. The bottle had been sitting in the hot sun, and that warm oil felt really good down there.

I looked all around and didn't see anyone, so I just started rubbing my finger around my pleasure button. I play with myself all the time inside, but I just threw caution to the wind and did it right there on the deck! I'm not self-absorbed or anything, but I do have a pretty pussy, so I like to look at myself as I masturbate. My lips are always kinda big and flappy, but they get really engorged when I'm turned on, just like my clitoris does, and it all looked so nice glistening in the bright sun.

So I kept on rubbing it until I just couldn't stand it anymore and slipped a finger up inside me and worked it faster and faster in and out. Oh, it felt so good! Getting wetter and hornier, I slipped another finger in as I twiddled one of my nipples with the fingers of my other hand. I was on the brink of an orgasm, but just couldn't quite get there, so I put a third finger in. I must have worked on myself for a good 10 more minutes, but still couldn't bring myself to the Big O. I needed something bigger inside of me, know what I mean?

I had a good-size chrome vibrator, but it was inside in the bedroom, and I knew if I stopped then to go get it, I'd lose the moment. I looked around on the deck for something and there on the plate beside my unfinished sandwich was my pickle. Since I was a kid, I like to eat those big, whole dill pickles, the kind they sell in the giant jar on the counter at the checkout register, but it was, well, really big. Should I?

So I picked it up. It had been sitting there on the dark plate in the sun for an hour now, and the first thing I noticed was that it was warm, which was good, since no girl would want a cold pickle in her. It was shaped just like an erect penis, kinda curved, so I licked off the pickle juice, and it even felt like a hard man, though thicker than any man I'd ever had. I love to give head, so keeping my three fingers working my cunny, I sucked on it, putting the wider end in my mouth.

This was turning me on even more, and I noticed the spot on the end where I'd pulled the stem off was kinda like a guy's pee hole, which I like to tongue when I give a BJ, so I did. After a few minutes of this, I couldn't wait any longer so I slowly slipped the narrower end in me. The further I got it in, the better it felt, and it was definitely the biggest thing I'd ever had in my pussy! Squatting in a baseball catcher's position, I worked it in and out of me as I watched my lips disappear on the in-stroke and mushroom out on the out-stroke. Darn, I was loving this!!!

I kneeled forward to angle it up against my clit, and those little pickle bumps felt devine sliding back and forth across it, as my oily boobs bounced up and down. OK, I was gonna cum, and cum I did big time, piercing the quiet with a long, uncontrollabe scream--aaaaaaaah!!!!! My pleasure quickly turned to embarrassment. Had anyone heard or seen me?"

Marty turned off the tape. I had not looked at her the whole time it played. "Well," she observed, "Looks like you enjoyed it," as she stared at the prodigious bulge in my thin poplin trousers. I finally forced my eyes to meet hers. She was, indeed, an extremely sexy woman I now realized, nearly forgetting her daughter. Wrapped up in the tape, I had not noticed that she had changed some things while we sat there listening to it on the leather couch as I slowly trained my eyes downward.

The long Southwest style denim dress, the kind that button all the way down the front, that she had on had become unbuttoned all the way down to the silver-buckled belt, revealing her 36D breasts and just-visible nipples held up high with a red underwire half bra. And she now sitting in a Indian position, I could see that, below the belt, all the lower buttons were unfastened, as well, affording me a clear view of a closely trimmed bush surrounding her luscious labia in a wet, sideways smile.

"Would you like me to take your clothes off and make love now?" she asserted. "Well, I really do need to get over to the library, but..." I kidded, leaning over to French-kiss her. She unbuttoned my shirt and kissed my chest, gently biting and sucking my nipples as I unbuckled her belt and slid the dress from her shoulders. Standing up together and rejoining me in another French kiss, she slid the shirt from my arms and deftly unbuckled, unfastened, then unzipped my trousers, letting them drop to the floor.

As I went to step out of them, she broke the Frenchy and kissed her way down to my boxers, grasping the elastic band in her teeth and pulling them to the floor. She removed my loafers, pulled off my shorts, pants, and socks, then stood back up standing straight as a soldier, ankles together, to stare at my nakedness. And I stared at her, but for the demi bra, nakedness.

I like to look at a woman standing up, and she was, though 20 years my senior, stunning. We just stood there looking at each other for what seemed an eternity. We would soon be fucking, but what was the rush, and she obviously felt likewise, supremely confident and proud of her body.

I smoothed my large hands all over her and was overwhelmed at her extreme hourglass figure, heretofore hidden by business suits and dresses. I could hardly get over her narrow waist, which I guessed to be maybe 22 inches at most. 36-22-36, I thought, going back to the quintessence of beauty 40 years prior.

Finally, I picked her up and lay her on the leather couch, lingering in a another long French kiss before kissing my way down her neck to her magnificent breasts, then on down her tummy and navel and pussy and down the inside of one leg to her fabulous feet then over to the other foot, up that leg and on to her snatch.

Hearing the Swiss clock there on the side table chime 7 o'clock, I decided I would eat her sweet pussy for precisely one hour, which I did, she softly cooing and running her dextrous fingers through my hair to climax several times. Her full, dark labia contrasted dramatically against the bright pink vaginal interior, and her barely hooded rigid clit made it so easy to lick and suck and pet that I could have gone for another hour.

Though she liked her equally dark pucker hole licked, she pulled away when I tried a finger in it, so I steered clear of that action. The most amazing thing was when she would cum: she would actually spurt out prodigious juices. When I rapidly vibrated my finger across her clit and held her open just so, love juice would spew out 6 or 8 inches!

Then, following a brief pause after the strike of 8, she stood up, sat me down, and said, "Now, an hour of oral for you." Whereupon she commenced by unhurriedly French-kissing me (she was an outstanding kisser), then kiss my ears and neck and chest and arms and hands and back and buttocks and legs and feet and at last, my cock.

After kissing it all over, she licked it up and down and all around like a lollipop, getting it nice and wet, then hand-job it expertly as she sucked and licked my balls and anus. When it came to the blow job itself, there were no better than Marty. She knew exactly how to suck with just the right amount of suction, swirl her tongue around and around it within her mouth, and use her fingertips to tickle my balls as she did so.

She also had that rare sense of when and how hard to clench her thumb and forefinger around the base of the shaft at the precise moment to keep me from cumming. And she knew the appeal of gazing straight up into my eyes with her big, green blinkers as she suck, suck, sucked away.

But perhaps the most amazing talent of her many was her deep-throating ability and technique. I already described her wide smile, and that's another way of saying she had a big mouth. She could not only get all seven inches of me into her mouth and down her throat, but she could also actually get both balls in her mouth at the same time!!! All without a single gag or bite. Now how many women can do that?

It was with this astonishing feat that I blasted my first orgasm. It was almost 9:00 PM. "Can I cum now?" Yes, she nodded, and I let her rip. She never missed a beat--swallowing over and over. In fact, when I pulled out of her mouth, there was not even one drop of post-climactic semen leakage left.

The clock chimed 9 times, and we poured another glass of wine and ate the fortune cookies. Hers said, "You will soon experience a great and pleasurable event." Mine read, "A wonderful surprise awaits you in the unlikeliest of places."

We chatted some more about her making erotic tapes, and I followed her about the downstairs as we took the plates to the kitchen, and she straightened every little thing and emptied waste paper baskets in every room. I find it incredibly sexy watching an attractive, naked woman standing and moving about doing all kinds of regular, everyday things, and so I was really enjoying this little mundane interlude.

But Marty was still not altogether nude--she still had on that red demi-bra--and I had purposely not removed it even though I was dying to unleash those big hooters. But I would wait to do that a little later.

At 9:30, I felt the twitch down below while we were in her bedroom, so this seemed like the time for round two. French-kissing her standing next to the canopied bed, I fingered her wet again from behind as she two-handedly stroked me up to a full erection. Laying her back into a missionary position on the tall bed while I stood on the floor beside it, I plunged into her deep in one motion as she gasped.

Looking me straight in the eyes and breathing in unison, I rocked slowly in and out of her with my hands clasped around that tiny waist. When I squeezed tightly, I could almost touch my hands together. I bent her knees back to her ears to get a better view of myself in her cunny, and what a clear and beautiful view it was.

She was getting worked up fast, so I increased my pace as she locked her arms around her legs to hold them in place. The insides of her thighs were pushing her boobs together in an even deeper cleavage with the whole of her areolas clearing her demi-bra. Though I wanted to see the entirety of her tits badly, I still chose to save them for a later moment.

Without ever withdrawing, climbing into the bed, I steered her sideways into a spoons position. Her soft bottom squished sensuously against my thighs as we twisted to French kiss while I rubbed her clitty. I could feel her pussy contracting now, and she raised her upside leg up to give me deeper penetration, and, whispering, "I like it from behind like this," she started to cum, and, like before, gushing gargantuan gobs of gash juice.