Sexy Older Secretary

"$75 going once. ... $75 going twice. Sold, to number 32, you my friend are the proud owner of a dinner date at the home of Ms. Nancy Thrash, isn't she lovely," announced the auctioneer. I don't know how or why I had gotten roped into coming to this event. I was foolish to think that this would ever work out like I had planned in my head over and over when Sheila told me about the fundraiser.

I had only lived in West Plains for a little over 6 months, having graduated law school and passed the bar the previous spring. At just under twenty-five years of age, my first job landed me as an assistant prosecutor in mostly rural Howell county in the south central part of Missouri. I was hired as the first full time assistant prosecutor after the elected prosecutor, Lowell Mathers, had successfully lobbied for and received permission to hire a full time assistant to give him more time to politic, or goof off and drink beer at the local Elks lodge. Not that I was complaining, having interviewed for four other positions only to be outdrawn by classmates with better G.P.A.'s coming out of law school. After the first year of law school, I had realized that I would not match my stellar grades of undergrad and resigned myself to the fact that drinking beer and chasing undergrad sorority girls was much better than cramming for boring law school exams. I was fortunate enough to have worked the previous four summers at my step-uncle's large cattle ranch, which lay mostly in Oregon count, just southwest of West Plains. Luckily for me, Lowell and my step-uncle were best friends and my timing out of law school could not have been any better than to be hired as Lowell's assistant.

To say that West Plains was my dream destination was far from the truth. However, the starting salary was not terrible and my step-uncle threw in the cheap ass rental of one of the old farmhouses he had bought over the years as he had expanded his cattle empire. For a mere $100 a month, I was the proud renter of a 3 bed 1½ bath house with a ½ basement, shed and barn that, while 70+ years old, had been well maintained and was less than twenty minutes from the Howell County courthouse, even though I was technically a resident of northernmost Oregon county. In addition, Uncle Frank had left me a brand new four wheeler in the barn for me to blow off some steam after work, provided that I checked the nearby 160 acres of grazing land to ensure the fences didn't go bad and give the cattle a chance to escape.

While not thrilled with the night life in West Plains, I had soon settled in as a regular in several of the local watering holes in Oregon County. I was fortunate enough to have one situated within a quarter mile of the rental house to avoid any unnecessary driving under the influence tickets to derail my budding legal career. I avoided drinking in West Plains to keep up appearances. My step-aunt had done her best to set me up with the best available women my age in the area, but the pickings were slim and I had yet to hit it off with anyone. The problem was not so much the girls I was being set up with on the weekend, but instead was the one woman I spent most of my days with at work, Sheila.

Sheila was Lowell's head administrative secretary, recently divorced, and although she was 47 years old, she looked like she was in her mid-thirties, if that. Not that she tried to show it off. If anything, she dressed older, but could not hide the curves in her well kept body that had survived three kids who were out of high school and 28 years of marriage. Her husband had made a fortune in construction while she raised their three kids and then decided he needed a younger, sexier wife, leaving Sheila in a whirlwind of self-doubt and shattered confidence about herself, even though she looked great for her age.

In the six months that I had worked with Sheila leading up to this auction, I had gotten to know her rather well as she and I were typically the first to arrive at the office and often the last to leave. Howell County was not a booming area for crime, so Lowell kept rather liberal hours and quickly adjusted to my eagerness and willingness to handle as much as I could. In the time I spent with Sheila, I couldn't help but fantasize about what it would be like to get her into a bedroom – or take her right here in her office. She talked with me about her lack of a social life and seemed interested in seeing if I was going to find a steady girlfriend, talking more to me like an interested mother figure. She also talked to me about her kids and the sometimes stupid choices they made, always blaming those on her ex-husband. She did not have very nice things to say about him.

In the weeks leading up to the auction, I had heard Lowell asking Sheila if she was putting herself up on the auction block again this year and my curiosity was peaked. I finally got her to elaborate one afternoon after everyone else had left the office. She told me the local women's charity club had an annual Christmas gala to raise money for the Salvation Army. As part of the gala, members of the club donated time or resources that were auctioned off to the highest bidder. While the married women donated items like food or blankets, the single women had recently began auctioning services that included dates, taking out a man shopping, or coming by to clean his house. Since Sheila was freshly divorced, she had been auctioned off last year to clean the house of a bachelor. Unfortunately, she was at the bottom of the bids and was a little self-conscious about doing it again this year.

"I can't compete with the other single girls in our club," she told me. "They are fresh out of college, young, and beautiful. No one wants to spend time with an old divorced woman. I'm the only woman almost 50 who gets roped into this event. I don't want to be humiliated again this year."

I told her there she didn't need to worry about everybody else and just have fun. "Show a little leg and the auction and smile. I've seen the other women in your group and young or not, there's not too many that have anything on you." She smiled, actually blushed a bit, and then told me, "Well if I'm going to do this, you at least have to go. Who knows, you could meet someone."

So here I was, sitting near the back as Sheila was announced as the next and last of the twenty ladies to donate their services. So far, the highest bid had been $150.00 and the lowest $20.00. I was going to make sure Sheila didn't go that low, even if I had to bid against myself.

As the bidding for Sheila started, my mind kept going back to a conversation earlier in the evening I had had with a friend of mine, Doug, who was at the event. He was talking about last year's event and how several of the women who had been auctioned off for $250.00 or more had provided the winners with a special treat. "It's not really prostitution if it's for charity," was how he put it. Not that it was well known, just one of those underground rumors that never really died. I told Doug how Sheila had roped me into coming to the event and her story last year and how I was going to make sure she didn't get embarrassed this year. We chit-chatted a little more and then the auction began.

The bidding for Sheila began at $10.00 and two older gentlemen immediately began a bidding war that escalated the price to $60.00. They stalled a bit, so I threw up my hand and saw Sheila smile and blush a bit. One of the older guys bowed out but the other bid against me and we got up to $110.00 before he got gunshy and left me as top bidder. The auctioneer was at two when another hand shot up and took over the bid. I couldn't see who it was at first, but then caught the body attached to the hand. It was Doug, and he was winking at me. I quickly bid again and his hand fired back up. Back and forth we went until his high bid stood at $240.00. He winked at me again and I put my hand up for the $250.00 bid. He shocked me again by bidding, then winked twice at me. Not knowing what the hell that meant, I bid once again, thinking to myself this was as high as I was going to go. Doug backed off and I ended up with the highest bid of the night so far, $270, and a very shocked but smiling Sheila who came over to give me a hug.

Sitting down with me to have a drink, Sheila said, "Ryan, you didn't have to do that, it was too much money." I told her the pleasure was all mine and she squeezed my hand. "Well, I do appreciate it. It was nice to be the highest so far, not that it will last." Sheila sat with me as the final five ladies were auctioned. One bid for the very beautiful Lacey Chalmers, a local son of a dairy farmer who was a stunning beauty at age 24 went for $320, but Sheila tied for second when another gal went for $270"

As the festivities were coming to a close, Doug brought us two champagne glasses to congratulate us. We accepted, then Doug asked me what I was planning to do with my date, smiling as he asked. Sheila blushed a little, then asked me the same thing. I asked her to come by my house and spend part of the day helping me spruce up my place, noting that it needed a woman's touch. Sheila said she would be happy to and would also bring us a basket-lunch to enjoy. She suggested we do it tomorrow since it was supposed to a nice day for November and we could open all the windows. We made chit-chat for a little bit, before I bowed out and joked that I needed to go home and clean up before our cleaning date. Sheila gave me another hug and then said she would see me tomorrow at my place at 9:00 a.m.

Thoughts swirled through my mind as I drove home. Did Sheila know about the underground rumor? If so, did she plan on making a move tomorrow? How would this affect our work if she did? Should I make a move? What if I did and it failed, how could I look her in the eye at work then? I didn't know what to think or what to do. However, the thought of having Sheila all alone at my place was making me hard. I almost pulled out my dick to jerk off while driving home, but the road I lived on was too curvy. I made it to the house and took a long shower, relieving some tension and myself in the process.

I barely slept that night contemplating what I should do. I had a hard time believing that Sheila would come on to me spontaneously, but thought that with a bit of a push, she might let loose with me. I thought and thought about what I should do and then finally put together something in the bedroom that I could use if the scenario presented itself.

Right on time, Sheila knocked on my door at 9:00 a.m. She looked great in a simple, yet sexy denim skirt that had some dried paint on it, a buttoned blouse that was quite form-fitting and accentuated her breasts more than I had noticed at work, and a handkerchief wrapping her hair to give the appearance that she was ready to go to work. She had also brought along some cleaning supplies and a lunch basket, which I helped her unload. I couldn't help but notice the bottle of wine in the basket, which I thought to be promising. Even better was that I had two bottles chilling in the refrigerator myself.

"So what do you think of the place," I asked Sheila as we sat for a cup of coffee before starting to work. "Can you do anything with the place. There's some extra furniture and curtains in the basement if you want to make some décor changes."

"Why don't we go down and take a look," she said. "In fact, why don't you give me a tour of the place before we get started so I can come up with some ideas."

We took a walkthrough of the house, although I inconspicuously skipped the bedroom. If she noticed, she didn't say anything. After walking through the house, we then opened all of the windows to get some fresh air into the place. She then put us to work cleaning, giving me some lifting chores for moving some of the heavier items to and from the basement while she went to work cleaning the bathrooms and kitchen. I worked up a bit of sweat moving the furniture and noticed her looking at me on more than one occasion. I noticed that she had undone the top two buttons on her blouse to reveal a hint of her cleavage. Not knowing whether she was hot from the work like me or working her way to seduce me was giving me fits. I could not get a read on her. However, my cock was twitching at the thought of ripping of her skirt and ravishing her on my bed.

I finished moving the furniture at her direction and helped her finish the kitchen work. A real treat was when we had to get a ladder to replace some light bulbs on the high ceiling in the kitchen and outside porch. She suggested that I hold the ladder while she climbed up. While I didn't get a view up her skirt, I did hold the ladder in such a way that she had to climb right by me and I did watch her curves as she moved by me. For an older woman, she was very fit and sexy.

We moved on to the living room and finished there. By then it was almost 1:00 p.m., and time for lunch. Sheila went to her basket to get things situated and I took the opportunity to open a bottle of wine from my fridge and put it on the table before excusing myself for a bathroom break.

It was now or never, I thought, as I took a leak. The only room left was the bedroom. I could set up what I had planned and go for it or put away what I had planned and finish the room and probably never have the chance again to get Sheila into my bed. What to do, what to do? I finally decided to leave it as is and see what transpired during lunch.

When I came out, Sheila had laid out a small, but nice spread for the two of us. A bowl of pasta salad, some mixed fruit, a few pieces of homemade fried chicken, and a cherry pie lay out on the table with two plates, two glasses, and two bottles of wine.

"I didn't know you had opened a bottle," Sheila said as she poured us each a glass. "We're liable to not be in a working mood if we finish all this food and wine."

"Sounds good to me," I replied. "We've put in a good morning and got a lot done. Time to relax. We both need it since we practically have been doing all the work at the office these last few weeks."

"You're right," she answered. "But no office talk today." We ate and drank and made idle chit-chat for the next hour or so. I was doing my best to keep the wine flowing into her glass, and did not try to stop me. The more she drank, the more relaxed she got with her body and her mouth. We were sitting close enough to touch each other and each time I said something funny she would laugh and put her right hand on my knee, quickly and lightly at first, but then a bit longer each time. We also got around to the topic of dating and she heavily implied she was lonely and would like to meet someone who would make her feel special. When I heard that, I knew that I had to go for it.

I took the second bottle, now near empty, poured us each a final drink, then excused myself again for a bathroom break. Instead of heading to the bathroom, I snuck into my bedroom and put the final touches on my plan. When I returned, Sheila was putting away the dishes we had used and moved them to my sink for cleaning. I drained my glass and grabbed hers, taking it to her and exchanging it with the dish towel she was using to wash the dishes to finish up.

"Well, what now," Sheila asked. "I've got about an hour or two's worth of energy if you have any other places to clean."

"There is still my bedroom," I said. "It's not big and shouldn't take too long. I think I forgot to show it to you this morning."

"Lead the way," Sheila said as she finished the last of her wine. I led us through the living room, to the hallway that ended with my bedroom door. My hands were shaking and my heart was pounding. This was either going to go very bad or very good.

I opened the door slightly and then motioned her to go in ahead of me. She opened the door all the way and entered. When she did, must have noticed the dozen or so candles I had adorning the room, a red scarf over the lamp by the bed to let off a romantic glow, and soft music playing in the background. She stopped a step or two in and gasped, her legs bending at the knee. Knowing it was now or never, I put my hands at her waist to hold her steady and then put my lips to her right ear, whispering, "I had something else in mind for this room. It involves me and you and my bed. I've wanted you for so long." I then put my lips to her neck and kissed her lightly, while moving my hands up her side and cupping her breasts.

"Ryan, we shouldn't. We work together and I'm old enough to be your mother," said Sheila, although she was responding to my touches in a way that indicated she did not want me to stop. I continued to massage her breasts and body while I replied, "My mother was never this sexy and I don't care about work. Your mind may say you do, but your body is saying differently. I want you right here, right now."

Sheila pulled herself from me and turned around. I was certain I was about to get viciously slapped in the face before she left and told Lowell and I was out of a job. Instead, she just stared at me intently for a few seconds before extending her arms and pulling my face to hers for a deep kiss. Our tongues swirled and our arms moved about, exploring each other's body.

She moaned when her hand brushed by hard cock, which was straining against the fabric of my pants. I fumbled with the buttons on her blouse, opening it to display her soft billowy breasts encased in a silky white bra. My mouth moved from her lips to her neck, kissing and sucking my way down to the valley of her breasts while my fingers struggled to undo what I thought was a clasp from behind, but having no luck.

Sheila finally moved her hands to the front of her bra, unclipping it to allow her buoyant breasts to spring free. I took a moment to drink her in with my eyes while she reached for my shirt. Instinctively, I grabbed my shirt and pulled it over my head, then reached down to unbutton my pants and pull them down, my boxers trailing close behind. Stepping out of my shoes and pants, I watched as Sheila stared at my cock with an amazed look in her eyes, almost afraid to touch it. I took her hand in mine and guided it to my cock, reveling in the soft feel of her silky hands as she wrapped them around my swollen member.

The gentle touch of her hands had me ready to burst, but I did not want to cum in her hands. I reached for the zipper on her skirt and tugged gently, opening it enough to allow it to slide past her hips. Grabbing her panties with the skirt I pulled firmly to get them down to her ankles. Bending down, I slipped off her shoes and then had her step out of the skirt/panty combo.

Both of us now naked, I stood back up and embraced Sheila again, kissing her as I eased her to the edge of the bed and down in the center. Reaching down, I felt between her legs and probed my way through her furry patch to her swollen lips with my fingers. She was obviously excited stemming from the wetness surrounding her hole. I could wait no longer as she lay before me and spread her legs wide before grabbing my cock and lining it up with her sweet pussy.

The tip of my cock eased its way between her folds, but it was slow going because she was so tight. I steadily increased the pleasure of my strokes, going deeper with each thrust. Finally, I buried myself completely inside her as she whimpered in pleasure. Stopping briefly to compose myself, I stared into her eyes and kissed her deeply again as I began pumping in and out of her with deep strokes. I then watched her breasts and stiff nipples shaking in front of me as I pounded her against the bed. Though motionless at first, Sheila quickly responded and moved her hips to time my thrusts for maximum penetration and pleasure. She locked her legs behind me and spurred me on with her groans of delight.

I was fast approaching orgasm but was doing my best to hold off until Sheila got off. I didn't think I would make it, but Sheila began panting and bucking and moving in a way that signaled her impending orgasm. Her heels dug into the small of my back as she moaned and spasmed against me, releasing her juices on my cock. That set me off and I blasted my seed inside her, cumming in several spurts before collapsing on her breasts.