5 comments/ 41468 views/ 1 favorites Persistence Pays Off Ch. 01 By: nazzadry 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. Persistence Pays Off Ch. 02 When I arrived at work the next morning, I was anticipating a very awkward scene. I wasn't sure whether to expect her to avoid me from now on, or that she might someday address me directly. As it turned out, the latter scenario was the correct guess. Slightly averting my glance, I saw her walking down the corridor directly towards me. "Here it comes," I thought, and tried to keep away feelings of dread and foreboding. "Let's talk," she said. She gestured towards my empty office, which promised more privacy for the both of us. Pushing the door to my office closed behind her with her right foot, her body language was immediately apologetic. So were the words that followed. "I'm sorry. I haven't allowed myself to be sexual like that in a long time. When my husband stopped being interested, I told myself that I didn't need sex anymore. Being with you last night made me realize that I did." Not missing a beat, she leaned in for a kiss. I tilted my head slightly to the side as her lips remained stationary, waiting for my contribution. Accepting her mouth eagerly, I embraced her strongly with both arms, pulling her close to me. Before long, my hands trailed down to her ass and grabbed greedy handfuls. "Not here," she said, her voice suddenly raspy. "Tonight. Your place this time." Five o'clock dragged on as I rushed through my work. As not to arouse suspicion, we both took our own cars to my apartment complex and parked in an outside alleyway. Arriving first, I stood on the brick steps leading into the back entrance of the building, waiting. I saw her round a corner, and then locate me with her eyes. She smiled ear to ear at me, which in turn made me grin back. I held the door open to for her. She followed behind me, up two of stairs. The building was seventy years old and as a result, an elevator had never been installed during its construction. Now that I'd gotten my wish, I began wondering what she was thinking and what she really wanted from me. Every woman I've ever slept with has different wants and desires in bed. No two women are ever the same that way. She sat down on my bed and removed her earrings and jewelry. Her engagement and wedding ring had been taken off long before. High heeled shoes were kicked off into a spare corner of the bedroom. I wordlessly helped her with the zipper to her dress. This time, it was her turn to take the initiative, to make a specific request of me. I was to be the one lying on my back this time. Giving me a blowjob turned her on in ways other sex acts could not. It may have been the aspect of control. I enjoyed the sensation, to be sure. I've never been able to have an orgasm when being sucked off. I'll never turn it down, but I'm far more interested in the main course than in the appetizers. The act of fellatio itself was arousing enough for her to make penetration surprisingly easy, once we got there. She crawled between my legs and took my mostly erect cock in her mouth. "I've been wanting to do this to you for months," she said, grinning lewdly. She kept it up for as long as she had strength in her jaw. When she could no longer perform, she straddled me, facing me directly. Grabbing hold of a saliva-wet cock, she guided it into her. It took all of three seconds for all of me to slide into her. Rocking back and forth, she closed her eyes. I thrust up against her as she thrust downward, impaling herself on me. Feeling like a kid in a candy store, I wanted to try everything. Like the first time we had sex, I now focused squarely on her clitoris and vagina. I was trying to return the favor. But in the middle of what I was doing, I was interrupted. "I know you're good at this, but it doesn't really do all that much for me." Cunnilingus had been a calling card of a sort for me. It was disappointing to know my services weren't needed. But they were especially wanted in other areas, so before I had time to pout or complain, there were lots more to do and see. Even so, it's always disappointed me when my talents with lips and tongue go unappreciated. She felt that oral sex was a most appreciated tease, but could not climax that way. She indicated that she wanted me to insert a finger or two into her anus. That alone would cause an orgasm, I was told, and it would be stronger that way. Most women I'd slept with had never dared go anywhere near there. Several minutes of lubricated penetration later, she was finally ready for anal intercourse. An extremely auditory lover, I get off easily when hearing sounds of arousal. She was tremendously vocal. "I didn't used to be like this until I was 40," she said. "I could never have an orgasm during penetrative sex." Ten or fifteen minutes later, I shot into her. My orgasm seemed to trigger her biggest one. Every time we fucked the effect of climax was always the same for her. Her eyes would roll back into her head and she would let out a sigh that was equal parts contentment, relief, and temporary disorientation. She lay on the pillow for whole minutes, processing what she felt. Before that instant, she'd been pulling and tugging madly against my shoulder blades. Like a crazed puppet master, she made sure that I thrust my cock into her from all the best angles for her. I felt a little like she was using my arms and shoulders as the steering poles for downhill cross country sledding. My desire to get her off was such that I was willing to submit to the practice. She knew what she needed. I only wished that there was something I could do to assist, though I'm sure she'd have told me first. She had a childish sense of humor, I learned. I'd never been privy to this secret side of her before we became lovers. At the conclusion of our lovemaking, she would rush to the bathroom. My semen would drop out of her into the toilet, due to gravity, an act that never ceased to amuse her. I never saw the humor. She kept her hair up almost all the time, perhaps feeling that an older woman with long hair was not especially desirable. I couldn't have disagreed more. With her hair down, she looked fifteen years younger. The dark olive tint of her skin was particularly accentuated, though I had to say that I was never entirely sure what her original hair color had once been. Now that the door had been opened, how often would this happen? There was something fun about adultery, fun about being wicked and sneaking around, fun about defying convention and morality. I never wanted this to be much more than an occasional good time, but how did she feel about it? From habit, I knew that her real thoughts would not be revealed for a long time.