Persistence Pays Off Ch. 01

I have always been attracted to women much older than myself. Maybe it's because I grew up in a family with any number of strong women for role models. Then again, it could always be a simple matter of basic preference. When I've come across an older woman who will take my affections and flirtations seriously, I know what is to follow shows promise.

We work together at the same small office. Among my co-workers I'm a flirt with a reputation for enjoying the game and playing it well. During routine interactions throughout the workday, I've put my best act on, seeking to get across my intentions to her. For several weeks, everything I tried seemed to be for naught. I was beginning to wonder whether I needed to abandon my plans altogether.

Then, an unexpected breakthrough took place. She began to speak to me for longer and longer periods of time. Her body language conveyed that the attention she was receiving was unusual for her, but that she was quite appreciative of it.

Before long, she'd stride past my desk on her way to her own office, indicating by eye contact and body language that she enjoyed the attention. I'd gotten my foot in the door, but whether she'd even consider physical contact was entirely up in the air.

Women before had been satisfied with this much. They've wanted nothing more than an elaborate fantasy. I conceded to myself that she might have only thought of this as an entirely harmless and safe outlet. It was up to me now to delicately advance my aims and correctly read the signs provided me.

I left cryptic e-mails with her, asking entirely unnecessary questions, desiring face-to-face meetings to consider mere trivialities. At the outset, she calmly and kindly answered my inquiries. I suspect she knew what I was up to, though pushing past specific boundaries was still off the table.

I was persistent and inscrutable, beginning to drop hint after hint. I didn't want to be too obvious, but every day I thought to myself that being entirely transparent was the only way this would ever happen. I arrived at work one random day hoping that she'd agree to take me to bed, at long last. Fortunately, I didn't have to wait much longer.

We always left at about the same time every afternoon and had made a habit of saying goodbye to each other. As everyone else filed out of the building on their way home, she tarried a little longer than she ever had before.

"I have the house to myself tonight," she said. "Would you like to join me at 7?"

She shot me a flirty grin as she paraded outside in high heels, strutting out the door. There was an excited spring in her step as I stared at her legs as they headed downstairs towards the elevators. I didn't have to be asked twice. Weeks of hard work had paid off and I intended to make the most of it.

I arrived that evening with my mind racing. I was considering a million different tantalizing outcomes, and would have been happy with even one of them. Parking my car in the garage, I rang the bell outside the front door to the residence.

She appeared, presently, delicately made up, which was unusual. She rarely ever wore anything beyond lip stick. Since work had ended, she changed into comfortable clothing, wearing a sun dress that deliberately showed off her long legs.

In stocking feet, she was only a couple of inches shorter than me. I'm exactly six feet in height myself, and have always liked tall women.

We looked at each other with a combination of longing and desire, though I gathered that she was not entirely comfortable with this arrangement. Nervously, she sat next to me on the couch. It's been a really long for me, she said. I could see her hands trembling a bit as she sat down next to me.

"I want you to know. I love my husband."

She said this firmly, directly, and with great purpose. Staring me directly in the eye, she repeated what she'd just said.

"No, I mean it. I love him."

I didn't doubt her. From prior conversation, I knew they'd been married twenty years or more. A career had come first. Late in life, the two of them decided to be parents. Their young son was a source of joy, but didn't change the fact that she'd lived a mostly celibate life for a long time. Becoming parents hadn't addressed a long-standing problem between them.

They hadn't had much of a sex life in years. In the beginning, she'd sought to adjust herself to that cold hard reality with a kind of weary stoicism. When the problem persisted for five years, she clandestinely purchased a vibrator.

Sensitive to his feelings, she never used it in his presence. When five years became a decade, her mind seriously began to wander, something she'd never thought possible earlier in life.

A tall, thin woman, with a long neck, she stood perfectly still and upright on the couch only a few inches away from me. Despite her nerves, I sensed that she wanted this to happen very much.

When I leaned over to kiss her, her whole body, previously tense and tight, went instantly slack and relaxed. Her kisses were purposeful and grateful, directed with care and appreciation. I've been with women before who wanted sex at a breakneck pace. Not here.

She removed her glasses. I removed mine as well, tossing them onto the table next to a neat pile of magazines. She took my right hand in hers and rose to her feet.

"The bedroom is this way."

The room was shadowy and dark, the bed sheets worn but clean. I felt like I was entering some sort of inner sanctum that didn't belong to me, somehow. It didn't stop me from my intended purpose, though.

I climbed on top of her, my hands sliding up bare, recently shaven ankles, then calves, then knees. Her legs parted to allow me access to farther up than that. After passing the thighs, my hands found what I'd been seeking the whole time. She was already slightly wet. I smiled.

My right palm pushed the cotton of her panties against her clit, rubbing gently. She took a sharp inhale of breath and moaned. My fingers moved underneath the crotch, making contact with smooth, moist skin. One finger began a slow slide into her, resting inside for a few seconds.

Simulating penetration with a cock, my right forefinger slid up and down. Underhanded, wrists up, I inserted a second finger.

She began to groan and fuck my fingers. Now lying on my stomach, I crawled up the bed. She'd kicked off the panties and I dove between her legs. Licking her clit purposefully, I kept up the friction of two fingers. As I persisted, she lubricated more and more. The sound produced now was liquid, a little like suction.

Her entire lower body began to tremble and convulse. I kept up what I was doing. All of a sudden, her pelvis thrust upwards with great force. I felt the orgasm rumble through like an earthquake. I removed my fingers from her vagina.

My right hand cradled my erect penis, seeking to guide it into her. Her eyes still closed, I could hear her breathing heavily, contentedly.

I penetrated her easily, my earlier work having made the task easy. While fucking, we kissed passionately, enjoying the additional stimulation provided by lips against lips. My chest heaved against hers, the hairiness of my body contrasting her smooth, soft skin. My lips sucked a very erect nipple into a warm mouth, as she pushed back against me.

Then it all changed. Snapping to attention, she rose quickly from the bed. "You have to get out of here...now!" Throwing a robe around herself, she escorted me off the premises herself.

"No one at work can EVER know that this happened! I have a reputation to protect!"

The door slammed in my face with great force. I wondered where our relationship was headed now.