Author's Note: I once thought that when a woman turned forty, she wasn't worth the chase. Well, let me tell you that I was wrong. There are many attractive, older women who for one reason of another are still unattached, and given the right man, they are always grateful for some tender loving and lusty sex. These three stories which span several years, are about just such a woman -- Janice.
Story #1: Serendipity
My name is Mike, and when I was twenty-three and single, I worked as a personal trainer at a local gym. The job didn't pay much, but it was a place to work out and more importantly to meet women. As with every summer, the gym had run a membership special with a free orientation and training session from a guy like me. This often entailed a sales pitch to join the gym and then another to hire me as a special trainer. Normally it was mission impossible selling myself to a bunch of gym bunnies who couldn't afford me or to those out-of-shaped older guys who were only interested in the aforementioned young female newbies.
You can imagine my surprise when my last Friday night customer turned out to be a good-looking Asian woman by the name of Janice. Although I knew looking at her that she was older than me, I was stunned to discover from her membership application that Janice was twenty years older. From the personal information that she provided me, I figured that she was a career literary editor and more importantly single.
From her loose button-down top, walking shorts, and jogging shoes, I also knew that Janice was a gym neophyte. To test my assumption, I told her that I needed to measure her to establish her baseline against which we could measure her future progress. Although clearly embarrassed, Janice allowed me to tape her. At five-feet-six-inches tall and a hundred-fifteen-pounds, Janice was a willowy 33-23-34 with small breasts, a flat stomach, a narrow waist and hips, tight buns, and nice shapely legs.
Although reserved at first, Janice gradually loosened up as I ran her through a light workout to determine her starting point. Through my constant banter, sparkling wit, and downright audacity, I discovered that despite her age and obvious attractiveness, Janice had never had a serious relationship. Unbelievably most guys assumed that because she was good looking that Janice had a steady guy, and as a result, never thought to ask her out.
The few men that did quickly proved to be dismal disappointments. Amazingly, Janice lost her virginity in her last dismal affair -- more due to her curiosity and his persistence than due to mutual love. After entering her forties, Janice found that eligible guys were seeking relationships with younger women, and as her list of possible bachelors shortened, the prospect of her becoming a spinster grew. Desperate for a change in life, Janice on a lark decided to join gym and met me.
I was showing her how to use the rowing machine. After securing her feet, I had Janice bend forward to assume the starting position. When she did so, her loose top fell forward, and her bra unexpectedly puckered give me an unobstructed view of her breasts. I knew that she was flat-chested but was totally unprepared for the sight to two incredibly huge nipples projecting tantalizingly from her pointy snow-white mounds. Each upturned ruby-red cylinder of tender flesh was nearly three-quarters of an inch long and about as thick. Gazing at her mouthwatering perky tits, I knew then and there that I had to have Janice.
After a brisk but thorough workout, Janice seemed open to joining the gym. When I asked if she'd like to continue her training with me, she replied, "Mike, yes I would be interested in some personalized training but that depends on how much you will cost."
"Janice," I casually replied, "I'm expensive but worth it." When I quoted an inflated price, Janice balked. It was then I pointed out. "Look, Janice, the price for my services as a trainer is negotiable. It's not set by the gym and is solely between you and me. I'm sure that if we talk about it some more, we might be able to come to some mutually agreeable arrangement."
When Janice said that she was open to the idea, I casually suggested, "Look, the gym will be closing soon. Why don't you come over to my place where we can talk in a more private and relaxing atmosphere? Just grab your stuff and let's go. We could discuss my services over some wine that I know you'll love."
As if she couldn't believe her ears, Janice was at her complete loss for words at my outlandish proposal. Yet despite her obvious skepticism, I could sense that she was at the same time intrigued. In whimsical effort to alleviate any concerns she might have, I said, "Look Janice, I cross my heart and hope to die if I do anything that you don't want me to do. Hey, I'm a gym employee, and you know exactly where to find me if I act inappropriately. Since my car is in the shop for repairs, I'll even let you drive me home. Come on, Janice, do you have anything better to do? What do you have to lose?" Janice thought about my outlandish offer for a while, then finally accepted.
The dim lights and soft music from my living room help set the mood as we lounge on my lanai at the back the house on an oversized recliner. Janice knew that we could be seen by my neighbors and assumed that this quasi-private setting would preclude any unwanted advance by me.
However, the evening's full moon, a couple glasses of bubbly sweet Asti Spumante, and a gentle massage were what were needed to loosen up a hesitant Janice. With her eyes closed, she sighed softly as her tense muscles relaxed under my skillful and practiced hands., Janice didn't object to my smooth talking, my accompanying feathery caresses, and my gentle but persistent breaths on her sensitive skin.
It was only when my fingertips brushed against her nipple did Janice become aware that I had completely unbuttoned her top and delved into her flimsy bra. Gasping sharply as her meaty teat immediately jutted from her heaving chest. I quickly but nonchalantly undid and brushed aside her front-snapping bra to freely fondled her other perky tit. God, I loved how her meaty nipples became engorged, elongated, and harden to press against my rubbing palm.
"Oh, no, don't, please don't, Mike! Please stop..."
"Do you really want me to stop, Janice? Doesn't this feel good, Janice? You have such tantalizing tits. You've been flashing me your big fat nipples all night long. I wondered if they were as sensitive as to look...and now, I know that they are."