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Sexy Older Secretary

By: bdr23



"$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. 


Sexy Older Secretary Ch. 02



It had been nearly 36 hours since I'd last seen Sheila, after she had snuck away from my bed and house while I slept, exhausted from our lovemaking. I didn't have the nerve to try at her home on Sunday and knew that we would have to see each other eventually. I was pretty sure she wasn't going to mention our little sexcapades to Lowell, or anyone else for that matter, but I was a bit nervous walking into the office on Monday morning. 

Sheila and Lowell were both in the break area/lounge, where they were most mornings drinking coffee, when I entered the office. Sheila did a quick smile at me and then turned her head, looking almost embarrassed. Lowell and I went through our normal morning hello routine and the only thing I had gathered was that Sheila had said nothing to him. I poured myself a cup of coffee, then excused myself to get ready for Court.

The rest of the day flew by without any real chance to speak with Sheila and by the time I got up the nerve to go down to her office after everyone else had left, she was gone, which was quite unusual because she and I were typically the last ones there and she almost always said goodbye if she left before I did. I was starting to think our little tryst was going to be a one time thing and the whole "awkward office atmosphere" was going to rear its ugly head.

I decided to say the hell with it and went home, grabbing a 40 ounce beer for the road and then changing to head down to the bar within walking distance of my house. By 8:00 p.m., I was feeling no pain and decided to head back to my place, making the short trek back in the cool autumn air.

Just as I was about to walk through the door, a set of headlights appeared and pulled down the drive, stopping in front of me. When the lights shut off, I could see the car and observed that it was Sheila's. She emerged and walked over up to the porch, looking dolled up in a red dress that showed a little leg and a black shawl that kept away the chill.

"Hi," I said, not really knowing what else to say.

"Hi," she countered. "I stopped by a few minutes ago but you weren't here or didn't answer, so I left. I saw you walk out of Shorty's and head this way, so I drove a bit and then turned around. Maybe I should go? I don't know."

"No, please come in," I replied, opening the door and gesturing her in. "We can talk or hang out or something."

She entered and I closed the door behind us. "Would you like something to drink? I still have a bottle of wine left from Saturday."

"Well, okay, sure," she said. I went to the kitchen and grabbed the bottle, pouring her a glass and grabbing myself a beer. She was standing in the living room when I returned, so I handed her the glass and we sat down on the couch.

The silence became a little awkward as we both took several drinks, clearly not knowing what to say to each other. I finally put my beer down and looked at her, saying "Sheila, I just want you to know I don't want it to be weird between us. Saturday was great and I'm glad it happened. I hope you are too." 

Sheila put her glass down and looked at me. "Ryan, Saturday night was great for me too. The best night I've had in a long, long time with a man. I'd almost forgotten how good it could be and I'm glad it happened too. But your half my age and we work together. We just can't let it continue, we can't." 

A tear welled in her eye and she started to tremble a little. I reached for her and cupped her cheek in my hand. "Who cares about age, and so what about work. We're not hurting anyone else. And we both want this to happen. Your mind may say no, but your body is saying yes," I said as my hand trailed down her cheek, underneath her shawl and dress and to the valley of her breasts, which were heaving. Boldly, I took my other hand in hers and directed it to groin, allowing her to feel my cock which was starting to stir. 

She said nothing as my cock grew around her nimble fingers. I reached up to unwrap and remove her shawl, lifting it over her and throwing it to the side. "Ryan, we shouldn't," she whispered, but I could tell her resistance was fading and moved closer to her, putting my lips just inches from her.

"Maybe we shouldn't, but I'm going to," I responded, extending my tongue to graze her soft lips. I pressed further, parting her lips with mine and snaking my tongue inside her mouth, probing to find hers. Any thoughts she had of stopping me quickly faded and she responded to me, swirling her tongue around mine and joining me in a deep kiss. 

Her hand stayed on my dick as we kissed, and I groped her body like a teenage kid as we made out on my couch. I fumbled with the zipper on the back of her dress, pulling it down then reaching to slide the dress from her shoulders. I was able to slide it down past her bra, which was the same or similar to the one she was wearing two days ago during our first encounter. I trailed my kisses from her mouth and to her neck as I reached for the front of the bra, finding the snap and releasing her breasts before me again. 

Sheila lost her grip on my cock as I maneuvered in front of her to stroke and kiss her breasts. I was determined to make sure that she would never have second thoughts about us and focused all of my energy for the moment on her pleasure. She moaned as I took one of her taut nipples in my mouth while rubbing the other between my fingers. She just lay there trembling as I made love to her breasts, stroking and sucking and kneading them for several minutes.

Wanting to satisfy her further, I trailed further down her body, nestling myself between her legs and reaching up her dress for her panties, which were damp in the front. She lifted her hips so that I could slide them from her and reveal her furry bush. 

I spread Sheila wide, but started with a series of kisses on her right thigh, slowly and gently making my way to the center of her sex. Just before reaching her lips, I skipped over and trailed kisses down her left thigh, then alternated between thighs several times, stopping only briefly to graze her moist lips. She finally had enough of my teasing and grabbed my head with both hands, pulling me to her. 

"Ohhh, Ryan, right there, suck my pussy, right there, lick it good," she said as she swirled my hair between her hands, urging me on.

I licked the length of her lips with my tongue before making a circle and pushing between her lips as far as I could. Sheila responded by clamping her thighs over my head, nearly crushing my ears and forcing my nose to rub over her clit, which had extended outward. She finally loosened her grip a bit to allow me some breathing room and I moved my tongue to flick her clit with alternating up and down and side to side strokes, causing her to purr in delight. 

When I inserted two fingers into her hole and sucked her clit in between my teeth, Elise stiffened in orgasm and coated my face with her sticky love juices. "OOOOOhhhh god," she cried out as she bucked against the love seat, breasts heaving, a thin film of sweat trickling from her smooth body.

I continued to suck her clit and pussy with fervor until she finally pulled me away, too sensitive for me to continue. I leaned up to smother her face with kisses and share the nectar of her juices with her. She didn't seem to mind and met me with a sloppy kiss, eager to continue our coupling.

I quickly stood up and reached for the front of my jeans, unsnapping them and pulling them to the floor. My boxers quickly followed and I kicked them from my legs, freeing my cock for some action. I reached for a pillow and put it on the floor, then grabbed Sheila's legs, pulling them down and positioning her knees on the pillow, facing the couch. Kneeling beside her, I lifted the dress that had fallen over her and guided my dick to her backside, probing for the entrance to her pussy. Finding it, I rubbed the head between her lips before sliding into her, impaling myself on her. 

With two or three quick thrusts, I was buried inside her and stopped to let us both catch our breath. Slowly, I started rocking in and out, moving my hands to her hips to help her find a rhythm we could both enjoy. She groaned with pleasure into the couch and I reveled in watching her ass shake in front of me as we fucked. 

After a few minutes in this position I withdrew myself from her and pulled her from the couch, maneuvering her to the floor on her back and crawling over her. Again, I pulled her dress up to reveal her and slid my cock into her missionary style. I continued thrusting her while leaning in to kiss her, then holding my arms up to watch her breasts bounce.

"Oh, Ryan, I'm cumming," Sheila cried as I fucked her, feeling her juices coat my cock. This sent me over the top and I grunted in pleasure as my cock spewed into her, filling her with my cum. 

I peppered her face with kisses as my cock shriveled and plopped from her, though still leaving a sticky mess between us. Her breasts were still heaving, but slowly subsided as she came down from her sexual high.

Jokingly, I said, "You're right, we shouldn't do this anymore, I don't know what we were thinking," laughing as I finished.

"What am I gonna do with you," she replied, stroking my hair between her nimble fingers.

"Hopefully, fuck me again and again and again," I retorted, reaching to stroke her breast, then covering my mouth with hers for another long kiss.

Eventually, we got to our feet and composed ourselves somewhat, sitting back on the couch to finish our drinks. Sheila had pulled her dress over her to cover herself, sans bra and panties, while I sat there with my shirt, which had never come off, and nothing else.

As we had finished our drinks, Sheila rose and said, "This was great again, but I have to go."

"Stay," I said, rising as well, both from to my feet and in my groin. "It's early and I want you in my bed." Reaching for her hand, I grabbed it and moved it to my stiffening cock, saying, "so does he."

"You are a bad boy," Sheila replied. "I really should go," she continued, but her hand had a mind of its own, gently tugging at my cock which was swelling rapidly.

"There you go again, your mouth says one thing, but your body another. Tell me that you don't want to walk in that bedroom with me, take off your dress and make love to me all night, or at least half of it. I guess we should get a little sleep."

She started to say something again, but I interrupted her with my tongue. She was easy putty in my hands and melted against me as we kissed, my cock poking her belly while her hand was still wrapped around it. Breaking the kiss, I took her by the hand to my bedroom, pulled her dress from her and pulled her under the covers with me.

We made love again and fell asleep in each others arms. The combination of the beer I had consumed and our sexual activity wiped me out, and I again awakened to an empty bed, no sign of Sheila as the sunlight crept through my window. ___________________

Sheila and I talked little the next day, but she did tell me goodbye that afternoon, saying she had to pick up one of her grandchildren and watch him tonight. I told her to have a good night and dream of me as I would be thinking of her.

Wednesday and Thursday flew by as well and either she or I were busy and could not coordinate a time to be together. Friday morning, I arrived at the office early and found her alone in her office. I walked right up to her and planted a big kiss on her, which she eagerly reciprocated until coming to her senses and pulling away from me. 

"We can't do that here," she said. "As much as I want to, we can't. Lowell will catch us and I don't want that to happen."

"You're right," I replied, pulling away from her and respecting her wishes, at least for now. "I'll try not to do that again, although it will be hard." Changing the subject, I asked, "What are you doing this weekend?"

"I don't know," she said. "What did you have in mind?"

"Leave it to me. Be at my house at 9:00 tomorrow morning. We're taking a little road trip. Pack a suitcase, but a light one. You won't need too much, if you know what I mean."

"Where are we going?" 

"Somewhere fun," I answered. "No one will know us and we can do whatever we want. Trust me, you will love it."

"Okay," she said. "Now get out of here before someone hears us."

"One more thing," I said as I headed out the door, "Wear a skirt and button up blouse in the morning. And no bra or panties." With that I smiled at her and turned to walk out.

The next day she arrived promptly at 9:00 and grabbed a carry-on bag from her car. She was wearing a medium skirt and blouse with a jacket per my directions. I met her on the porch and pulled her in for a morning kiss, running my hand up and down her back and over her ass to confirm she was without undergarments.

"Very nice," I said as I stroked her bottom. "I see you listened to my instructions."

"You are so bad," was her only reply.

"Oh I know I'm bad, but I think you like it. You like being my little dirty girl, don't you. If we didn't have to get going, I'd like to pull you down on the front steps here and fuck you silly right now. But there will be time for that later."

I broke our embrace and grabbed her bag, putting it in my trunk and opening the door for her. She slid in and we got on the highway.

"So where are we going," she asked after a few minutes, her left arm stroking my leg. "How long do I have to wait for you to make good on your promise."

"It's about 3 hours," I replied. "You'll just have to make due til then," I said as I grabbed her hand and slid it over my semi-erect cock.

She squeezed me gently for a few minutes over my jeans. Whether it was the heat from the car or our actions, she pulled off her jacket and got a little more comfortable in her seat.

"Can I ask you something?" I queried.

"Sure."

"You said you've been split from your husband over two years and I was your first since him?"

"Yes."

"When was the last time you were with your husband before you split?"

"It was over four years ago that we were intimate before you and I got together last Saturday."

"During that time did you get horny?"

Sheila blushed and answered, "Yes, quite a bit."

"What did you do to take care of it?"

She blushed even more, "Well, you know. Girls do it to. We have to get off somehow."

"So you pleasured yourself?"

"Yes."

"How often?"

Sheila paused and didn't answer for me for about a minute. Finally, she said, "Not so much at first, but probably more after the divorce was final. Once or twice a week, maybe more sometimes."

"Did you masturbate this week?"

She just looked at me and redirected the question. "Did you?"

"Every night." I responded. "And every morning. I thought of you each time I did. Your breasts, your ass, your lips on my cock."

Sheila shifted in her seat, then whispered to me, "I did every night. I thought of you too."

"How did you get yourself off?"

She looked at me incredulously. "You want me to tell you how I masturbate."

"No, not exactly," I replied. "I want you to show me. Right now."

She looked at me, flustered, and stammered, "I can't do that in front of you. Not here."

"Why not?"

"It's too embarrassing," she said.

"I don't think it would be embarrassing. I think it would be sexy. I tell you what, we'll do it together."

"We can't. You can't. You're driving."

"Okay, I can't. But you can. Come on, it'll be fun. You're saying no again, but look at your hand on your hard nipple, your body is saying yes."

Sheila looked down at her hand and realized she had unconsciously been touching her nipple with her hand. What's more, her nipple was clearly visible through her blouse, pressing against the fabric.

"Unbutton your blouse and show me your tits. You know you want to."

Sheila hesitated briefly, then slowly began pulling her buttons apart. Soon enough she reached the bottom and pulled her shirt apart, exposing her breasts to me. They were rising up and down as she breathed heavily and both nipples were jutting outward.

"Take them in your hands and pretend it's me stroking your breasts. You can feel my hot breath on your neck. Roll your nipples between your fingers." She did as I said, arching her back as she did so, licking her lips.

I kept my eye on her and the road as she continued touching herself. It was time to go further. "Unzip your skirt and pull it down. Show yourself to me."

The hesitation gone, Sheila moved her hands downward, unzipping her skirt and pulling it down past her hips and down her calves. "That's it," I continued. "Imagine I'm there between your legs, just like Monday night. Show me how you get yourself off." 

Sheila moved her right hand between her pubes and found her clit, which was peeking out. She was clearly aroused. She began rubbing it, slowly at first then faster. She was clearly experienced in getting herself off and knew just where to push the right buttons. 

"Now imagine my cock sliding between your legs and gliding into you. Put two fingers together and imagine that's me inside you."

Sheila did as I instructed and jammed her two fingers between her lips, making a suction-sound as they slid in and out and she approached an orgasm.

I could barely keep my eyes on the road, watching Sheila pleasure herself in such a wanton fashion. She looked like she forgot I was even there as she moved her hands and cooed in pleasure.

"That's it, I'm grunting and ready and ooooo.., I just blew my load into you."

"Yes, yes, yes. OOOOhhhh Goddd!!! Yes," she cried and her hips jerked and she came, bucking her hips against my set and thrashing in the throws of her intense orgasm.

My dick strained as I watched her body shake, wanting to release it badly but knowing that I had to keep both hands on the wheel and part of my eyes on the road. I watched as Sheila came down from her orgasm, resting herself for the energy and passion she had spent masturbating in my passenger seat.

I let her rest for a minute then grazed my hand over her body to her left hand, gently tugging it toward my lap and to my straining erection.

"Open my pants and take me in your hand," I said and Sheila quickly unzipped me and free my cock from my boxers, pulling my dick out in the fresh air.

I strained against her hand as she gently rubbed me. I was hard as a rock and ready to burst. "Put me in your mouth," I said, reveling in the control I had gained over Sheila with my dirty talk.

She moved her head and positioned it above me, licking her licks before gently taking in the head of my cock. Her tongue gently lapped at the sensitive foreskin she had exposed with her hand as she urged me on. I really had to keep my eyes focused and open to the road as Sheila blew me while I drove us down the road at nearly 70 mph. I was lucky as I made out the straight stretch ahead while my nuts tightened and my eyes closed while I blew a heavy load of semen into Sheila's mouth. She sucked with vigor, not missing a drop as it pulsed between her lips.

I made sure to open my eyes before driving us off the road and somehow regained some sense of composure. We hadn't even made it halfway to our destination and had already both experienced mind blowing orgasms. Just wait til we get there, I thought to myself.

Just seventy miles to go, I reflected. Seventy miles to go.

To be continued... 



Sexy Older Secretary



Gently, I rolled off of her and my spent dick plopped from her pussy, leaving a trail of my fluids on her hips and ass. I held her tight in a spoon position, resting my dick between her cheeks and cupping her breasts with my left hand. "That was wonderful," I said to her as I gently kneaded her breasts.

Sheila was still panting, nearly unable to speak. She finally whispered, "That was the best sex I've had in over twenty years. You put my ex-husband to shame."

"There's more where that came from," I replied, as I moved my hand from her breasts down to her swollen pussy, rubbing her still engorged clitoris between my thumb and forefinger. "We've got all night."

As I continued stroking her, she asked, "Is this why you talked me into the auction then got your friend to bid against you? Did you think this was the only way I would come over to your house and sleep with you?"

"I don't know what you mean," I lied as my fingers continued stroking her.

"Bullshit," she responded, through ragged breaths. "Your friend was a little too obvious. I've heard the rumors, $250 bid for a good time."

"Well maybe I heard something. But that's not why I bid on you. Do you wish I hadn't won you?"

"Oh no, I'm very glad you did," she said as she placed her hand over the fingers I was using to stroke her to urge me on. "This still feels wrong, but you can do this as long as you like. I don't know why you want some old thing like me, but I won't complain."

"You don't look old and you don't feel old," I countered as I did my best to bring her off manually. "I can't wait to fuck you again with you on top so I can watch your beautiful titties bouncing in front of me. Do you like being on top?"

"My husband was always on top," she panted, close to another orgasm. I moved my hand slightly to insert my middle and index fingers inside her while I kept the pressure applied to her clitoris with my thumb. Within seconds, Sheila spasmed against my fingers with her second orgasm of the night, hips bucking and tits heaving as she got off. She looked so sexy with a thin sheet of sweat cascading her body as she came down from her sexual high.

My dick had finally recovered and was starting to stir, but I wasn't quite hard just yet. I allowed Sheila a few minutes to recover while stroking her hair then asked her if she had ever gone down on her husband.

Instead of answering me, Sheila lifted herself so that she was sitting next to me as I lay on my back. Gripping my balls with her right hand and my stiffening shaft with her left, she bent down to gingerly put her lips on the head of my cock. As she pumped my shaft with her hand, she began taking more of my cock into her mouth, swirling her tongue. Though not the best blowjob I'd ever had, she was getting the job done and my dick was responding. 

I urged Sheila on gently by placing my right hand at the back of her head. She began moving her head up and down as my cock extended to its full length. I moved my hands from her head to squeeze her soft melons and pinch her nipples, which caused her to moan through her cock-filled mouth. Although she was doing a wonderful job and bringing me close, I had other things in mind and grabbed her shoulders to pull her on top of me.

"I've never done this on top," Sheila reminded me. "Tell me what to do."

"Just put your hips over me and sink down on me at your pace. Once your settled, we can find the rhythm together." She moved her hips over my cock, which was sticking straight up. I grabbed her hips to line her up over me. Her cunt, still slick from earlier action, touched the head of my cock and slowly enveloped it as she sank down to my balls, her ass resting just above them. 

"Ohh, god, I feel so full," Sheila cooed as I gave her a moment to adjust. Then, using my hands to guide her hips, I worked us into a steady fucking rhythm. Sheila caught on, and I moved my hands up to fondle her breasts, which were shaking in front of me as we fucked.

Within a minute of two of our coupling, Sheila put her hands on my shoulders and dug in, nearly cutting me with her nails and she bucked her way to another orgasm, mouth opened and eyes half-closed. I continued pumping into her while she came and moved my hands back to her hips to keep her steady.

Sheila recovered soon enough and was ready for more, lifting her hips to almost cause me to slip out of her before coming back down on my pulsing member. I knew I was close and started to really move my hips faster and faster against her as my balls churned. Our bodies were slapping together loud enough to evoke clapping until I lifted up and grunted as my cock erupted deep inside her, filling her with my cum. 

It was her turn to rest on me following another terrific lovemaking session. Her nipples were so hard that they felt like they could cut through me as she rested herself on my chest. I pumped a few more times as my dick softened and withdrew from her hole, our juices leaking from us both and dripping onto my sheets. 

Exhausted, I began to drift to sleep, thinking of all the wonderful times that lay ahead for me and my sexy older secretary.