Cindy Gets Motivation

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This story is a work of fiction. All characters are over the age of 18. I hope you enjoy it and any feedback is appreciated.


Cindy Gets Motivation — Chapter 1

I moved into my condo about six months ago. It fits my needs perfectly. As I am now a single guy, I don’t need much room, it is only a short walk to a beautiful park, and since it is a gated community there is little noise or strangers knocking at your door.

About a month after I moved in, I saw some guys unloading furniture to the unit just below me. I live on the second floor with a deck that overlooks part of the park, and I have enjoyed having the condo below me vacant since I like peace and quiet at home. Of course, my curiosity got the best of me and I made a few trips down the stairs to my car in hopes of seeing my new neighbor. But my trips did not pay off so I made dinner and watched some tube.

Sometime later I decided to take the garbage to the trash bin and call it a night. As I was making my way back, I saw someone coming out of the downstairs condo. It was a younger lady carrying a large garbage bag and struggling with some empty boxes that were starting to slip.

“Let me help,” I yelled.

She looked up and smiled. “Well, it looks like I need an extra hand,” she said as boxes began to tumble.

“Hi, I’m Ted. I live above you,” I said as I reached for the boxes.

“Thanks. Sometimes I guess I bite off more than I can chew, so to speak.”

As I helped her get the boxes and trash to the dumpster, I learned her name was Cindy, she worked at one of the Tech firms and was elated to have her own place. From our conversation I gathered she was in her mid-30s, single, and her father has recently passed leaving her with enough money to buy this condo. Amazing how much one can learn by just listening. Cindy was cute, lean and very athletic looking. I thought it was great to have a pretty, bright neighbor like Cindy instead of some old matronly snoop living below me. We traded phone numbers and I told her to text me if I could help in any way.

Over the next few weeks we ran into each other several times and chatted. I was able to lend her some of my tools to do some easy home maintenance items, since she didn’t even have a screwdriver. Then one morning as I was at the park, getting ready for my morning run, when I saw her coming down the trail to the parking lot. She looked good in her running shorts and tight singlet. Apparently, she was a runner.

“Hey,” I yelled. She had just finished, gave me a wave and started to jog over.

“Hey yourself,” she yelled back as she neared me. “I didn’t know you were a runner.”

“Well, I used to be, but I’m more of a jogger these days,” I said with a smile. “You training for a race or something?”

“Yes. The 10k around the park coming up in a few weeks. I’m having a hard time getting my miles in,” she said as she took some deep breaths. “I just can’t seem to discipline myself to train like I need to.”

“Well, we all need some more of that,” I smiled. “I’m sure you will do well.”

“Have a good one.” She said as she headed for her car.

I waved as I started out, and some lecherous thoughts keep popping up in my mind. But hell, I was old enough to be her father. So much for such thoughts.

A week went by and as I was bringing some groceries in from my car, I saw Cindy sitting on her steps with a very forlorn look. She was in her running gear and it looked like she had just finished a late afternoon run.

“How’s it going?” I said as I walked up.

“Oh, just horrible” she said with a hint of anger in her voice. “I just can’t do it. I just can’t get my self-discipline working to get this training in. I ran track in High School, I know how to train, but I just can get it together.”

It was obvious she was upset with herself. “Listen, why don’t you clean up and come up and have a glass of wine with me on my deck. I just bought a couple of bottles of a nice Merlot. It is amazing how a glass of wine can make most things look a lot better.” After I spoke, I felt nervous. Had I stepped out of bounds, so to speak. It wasn’t like I was coming on to her, I just thought I could help her feel better.

Then this awkward pause developed. I was just about to say never mind when she lifted her head, looked at me, and smiled.

“That sounds great Ted. That may be just what I need,” she said. “Let me shower and I’ll take that glass of wine.”

About thirty minutes later I heard a light knock on my door. I guessed it was Cindy and sure enough there she was when I opened my door. The girl I saw in my doorway was not the jock running around the park, or the techie coming and going to work. Before me was this gorgeous, very tan young lady in a white gauzy sundress. Her light brown hair was loose and still a bit damp, and it was obvious she wasn’t wearing a bra. Her perky breasts pushed against the material Bostancı Sınırsız Escort of her dress, clearly outlining her hard nipples. She seemed completely unaware of this effect.

“I’m ready for that glass of wine,” she said with a big smile on her face.

After a slight pause, I gathered myself and replied, “Come on in.”

We retreated to the kitchen and I poured us each a glass of the Merlot I had just purchased and suggested we go out on the deck. It was turning into a very pleasant evening and my deck overlooks a deserted part of the park. We sat down and just took in the view for a minute.

“This is just what I needed. Thank you,” she sighed.

“No thanks needed. I’m glad to have the company.”

We sat and talked, sipped, talked, refilled glasses and talked some more. Cindy seemed like she needed to talk and I was more than happy to listen. Even though I struggled not to stare at her hard little nipples that were peeking through the bodice of her sundress.

She was thirty-five, never married, had been in a serious relationship that ended a couple of years ago. She wasn’t currently really dating anyone, but went out for drinks with some of the crew at her job. Her mother had died when she was young and her father raised her. She knew it had been hard for him being the Father and Mother to a young girl, but he was the greatest.

The conversation rolled around to her current issue she was dealing with. She just had lost her motivation. She was way off her goals for the race coming up, but even worse she sometimes found herself unmotivated at work. She was almost in tears as she described her frustration.

“I have always done a good job, I was an achiever in school, but I just can seem to get motivated,” she confided. “I wish my Dad was still around. He could always help when I got like this.”

She went on to tell how when she was young, and falling behind in her lessons, her teachers would send notes home to be read and be signed by her father. Her father was loving, but kind of old school.

“He would say, ‘Cindy, you need some motivation’, and I knew what was coming,” she said.

“What was coming,” I asked?

“Oh, He believed that to get motivated one needed a good spanking,” she smiled.

I laughed out loud. “Oh my. So that got you motivated?”

“Oh yes. Very motivated!” she laughed.

“Well, kids need some of that now and then. My dad tanned my bottom a few times when I was in elementary school,” I shared.

“Oh, it wasn’t just elementary school. His motivation technique was used even in my college days,” She exclaimed.

“Really,” I said trying to hide my surprise that she would get spanked as a college student.

“Oh yes. And it was very effective. Once I had a midterm paper I was struggling with and told him about it. He was fond of saying that you are never too old to get some motivation. I always knew what that predicted,” she said. “I ended up getting an A. Guess it worked.”

“Well, if it works, then I guess it works,” I laughed.

“And if I needed motivation really bad, I mean Really, Really Bad, he would spank me on my naked bum,” she exclaimed. “That was a REAL motivator.”

I laughed. But my mind was swirling and I was having difficulty staying focused. I hadn’t expected that particular revelation. I guess the wine was getting to her just a bit. I kept seeing images of her, without her panties, getting her backside spanked.

“On your naked backside, while you were a college student?”

“Oh yes. Like he said, you are never too old to get some old-fashioned motivation,” she said with a smile. She looked at her empty glass. “Got any more?”

We refilled our glasses and I could see I needed to get the second bottle from my liquor cabinet. We talked some more and decided we better eat something, so we order some Chinese food to be delivered.

After we finished our food, it was getting dark and we moved indoors. We both seemed like it was the most natural thing in the world for us to be drinking wine, eating Chinese, and talking. It was a very pleasant evening. Then our conversation turned to her current work and a project she was assigned.

“It’s almost like my workouts. I just can’t get ahead of this deadline coming up,” she said.

I could see this topic was stressful and said, “Well, don’t worry. All you need is some motivation.”

That sentence just came out and I hadn’t thought of the other meaning of what I just said. I was still clueless when I noticed she had gotten quiet.

“Ted, I think I need another glass of wine,” Cindy finally uttered.

I refilled our glasses again having almost gone through the second bottle. I was feeling very, very relaxed and I was sure Cindy was getting a wee bit drunk. We sat sipping wine for some time without talking. Finally, she looked up at me.

“Ted,” she said, “Wait here, I will be right back.” She jumped up and was out the door in a jiffy. Strange I thought, Bostancı Suriyeli Escort but we were having a very nice evening, so I just leaned back on the couch and waited.

It wasn’t too long when I heard that little knock at the door. Odd, I just figured she would come back in. When I opened the door there was Cindy, with her head down and holding out an envelope. It had my name on it. I took the envelope and said, “Well, come on in.”

Cindy was very quiet and came in and sat back down on the couch. She seemed a bit nervous and I was very confused. I looked at the envelope and decided there was nothing else to do but open it. There was a typed note in it.

Ted, Cindy has not been doing the work she must to do and needs some motivation. She badly needs this motivation. Really Badly. I am sure you can do what is needed to motivate Cindy to work harder.

Thank you.

I looked at Cindy and then back at the note. My mind was working overtime. I thought I understood what was being asked. And the words really badly kept jumping off the page. I had to make a decision, but this was not something I had imagined. Part of me said she is emotional and don’t take advantage. But then the reality came into focused. She is asking. Good Lord, she is asking in her own way.

In a split second it was done. My decision was made. This doesn’t come around a second time.

“Cindy, stand up,” I commanded.

My harsh command seemed to startle her a bit, as well as myself, but she slowly stood up. This was the final point of no return.

“This says you need some motivation, is that correct?” I asked.

“Yes. Ah, Yes Sir,” she said in a small voice.

“It says you really badly need motivation.”

Again, she hesitated, then in that small voice said, “Yes.”

“Come stand in front of me.” She followed my direction without a word. “I am going to give you some motivation, and it will be motivation you need really badly.”

She hesitated, then replied, “Yes.”

She looked amazing in her little sundress and I could not for the life of me keep my eyes off her stiff little nipples that seemed to be protruding even more than before. I could feel my member begin to grow. I knew it most likely would be felt once she was over my lap. But that couldn’t be helped, for the die had been cast

“Cindy, you understand I am going to spank you?” She nodded her head yes. “You won’t need your panties. Hand them to me.”

She looked at me for a moment and I thought she would backout of the game she had started. She was about to take off her panties, hand them to me, and I was going to spank her naked backside. And in doing this there was no way her private parts would not come into view. She must know that as well.

We both stood still. She looked me directly in the eyes and then slowly reached under the hem of her little sundress, inching her hands upward. She discreetly pulled down her panties and handed them to me.

Her panties were made of a gauze like material, and I am sure even with them on she would have been exposed. But the act of taking them off and handing them to me sealed the contract. She would be punished, she would be exposed, she would be spanked like a little girl. I don’t think I had ever been harder in my life.

“Come here,” I said as I reached out my hand.

She came forward and I took her left hand and pulled her toward me, placing her over my lap. She complied and adjusted, for she had been in this position before. I briefly readjusted my legs, keeping them slightly apart to stabilize her as well as to give my cock some room, as it was straining wildly against my walking shorts.

Once she was stabilized, I took hold of the hem of her little dress and slowly inched it upward. She turned her head to look, started to say something, then just buried her head in her folded arms. I inched the hem up as slowly as my shaking hands could go. It was like opening all the greatest gifts you had for Christmas, and doing it very slowly. It was hard to do, but this increased the tension to levels off the chart.

Slowly Cindy’s naked backside came into view. The contrast between her lovely tan legs and her cute tight little ass was wonderful to behold. I pushed the hem of her dress up to the middle of her back. Now her ass was totally exposed and even with her legs together you could see just the slightest outlines of her pussy lips between her firm checks.

I recalled our earlier conversation when she had talked about getting spanked. She had said she would wiggle and try to get her father to stop. She would tell him it hurt. She would cry sometimes. But he spanked her. I would do my best not to let her get to me. I felt I had a job to do and it was a job that doesn’t come along every day.

I laid my hand on her buttocks. They were firm from all her running and smooth to the touch. She flinched at the touch of my hand. I couldn’t help but rub each check just a bit. Bostancı İranlı Escort Then, out of the blue, I landed my first spank. The sound was louder than I had anticipated, and maybe a bit harder than planned, but it worked. She let out a grunt at the first blow.

I began to set a slow, steady rhythm. Left cheek, then right. SMACK…SMACK…SMACK. Cindy let out a little grunt with each contact. After several she began to utter small little whimpering sounds. Then as this steady rhythm continued, she began to squirm. With each blow she would jerk a little, and this had the effect of her legs becoming parted. She continued to squirm and her little bumhole came into view, peeking out from between her blushing cheeks. My cock was twitching in my shorts, as if begging for release.

I kept up my blows without stopping. Cindy was squirming harder now; her legs were slightly kicking and it was all I could do to keep her on my lap. She began to cry out, “No, no, too much, I can’t take it.”

I kept at it. I was going to give her a good spanking. But the sight of her backside and all that was being exposed made me want to slow down a bit to take in her naked womanhood.

I slowed my spanks a bit so as to watch the show. And it was some show that was being presented. That’s when I noticed a glistening between her legs. Good Lord, she was getting wet! The sight of her moist, now swollen lips of her vagina almost made me come on the spot.

With all her squirming I had spread my legs further apart to keep her on my lap. Then after a rather hard SMACK she turned toward my body slightly and her right leg slipped down between my knees. This had the effect of her straddling my leg, bringing her now wet pussy into direct contact with my thigh. I instinctively closed my legs slightly which pinned her leg between mine. As we continued this spanking dance, I slowed down my attack. Now as she wiggled, her pussy rubbed against my thigh and I could feel her wetness on my leg. Her clit was making contact against the exposed skin of my leg as the squirming picked up with each SMACK.

My cock was about to burst and was almost painful. Then after one SMACK Cindy shifted during her squirming and rubbing. She moved her left hand to steady herself and it slipped down between my legs. Her movements had the effect of rubbing my swollen member with the back of her hand. If this was an accident or intentional, I could not guess, but the effect was electric. Now each of us were making sounds as we squirmed together. Her breathing grew faster and her squirming seemed to have a purpose. My own body was jerking as her hand continued to stimulate my rock-hard penis. One could not tell if it was a spanking or if we were just humping each other.

We were now in rhythm together. I grabbed her ass cheeks with both hand and pushed her pelvis down, rubbing her clit against my leg. Her hand now was grabbing my cock through the material of my shorts, rubbing it with abandon. Then with one final push of my hands Cindy let out a long moan and yelled, “Oh God, yes!” At that instant my damn burst and I grunted as I came with such force that I had to push down on Cindy’s ass with both hand so I would not buck her off.

Time seemed to stand still. We were both breathing heavily and seemed almost stunned. Slowly I started to help her up off my lap. As I got her about halfway up, she just slipped down the front of the sofa like a string of spaghetti, and sat on the floor next to my right leg. Her dress was still pushed up around her waist and she was completely naked from the waist down with her legs outstretched. I looked down and the small patch of public hair just at the top of her vagina was visible. It was a wonderful sight. She looked up at me with the most satisfied smile I had ever seen. I smiled back.

We both sat in silence like this for what seemed like a longtime, but was most likely just a minute or two. I let my hand rest on her shoulder and she reached up to smooth out her hair. She sighed and then looked down.

“Oh my.” She quietly exclaimed. She then began to try and adjust her dress, but it was pinned against the couch. I couldn’t help but let out a small chuckle as she looked up as if somehow now embarrassed by her nakedness. I helped her up and she was able to get back to a semblance of normality. We both sat back down on the couch.

“Oh my,” she said again.

“Well, do you feel motivated?”

She looked at me and paused, then smiled. “More than just motivated. Incredibly motivated,” she exclaimed.

“Good,” I said as I put my arm around her. She leaned against me and let out a sigh.

We sat like that for some time. Just sitting. Not talking. We both were making sense of what we just did. Was it the wine I thought, or was it I was a father figure of sorts? I’m sure that never happened to her and her father. It was all a bit confusing and I realized it hardly made any difference. It had been an incredible experience.

After a time, she turned toward me. “Ted, thank you,” she said. Then she leaned over and gently kissed me on the check.

I smiled and said, “Your more than welcome.”

“I hope I didn’t put you on the spot with the note. I was impulsive. I just need to be motivated and I knew this always had worked,” she said with a look of concern.

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