Cindy Gets Motivation Ch. 04

Things keep changing. After Cindy spent the night with me, we entered a new phase of our rather unique relationship. One has to call it a relationship of some nature, for we are very, very intimate. It was great waking up with such a beautiful and complex creature. She is difficult to describe, much less understand. I have no North Star to guide me, so I just roll with it, so to speak. So far it has been fantastic; she is a master in subtle, and some very non-subtle hints from time to time.

Just yesterday, only a couple of days since our memorable shower and post shower activities, I found a hand delivered sealed folder at my door. It was from the Institution for Motivational Studies. You have to give Cindy credit; she is very creative. I opened it immediately.

It contained a letter and a synopsis of a study by the Institute. The letter stated I had been nominated as a licensed Motivator Practitioner and they now had me on their mailing list. Enclosed was a recent study regarding the Motivational Techniques and Lasting Effectiveness. I was pleasantly surprised; however, I was not going to add this to my resume just yet.

The bottom line of the study, no pun intended, was that prior research had shown conclusively that corporal punishment increased motivation by over 75%. And it was common practice that post punishment that included digital manipulation of the genital area increase the effectiveness substantially. This stimulation enhanced the effects of the corporal application and was still advised as part of the modality. However, it was found that vaginal intercourse with female participants helped increase the effectiveness in addition to manipulation. Therefor the new guidelines recommend this addition to the current modalities if at all possible.

Goodness, I loved this woman. I had to laugh, but also, I had to say she was one of the most creative people I had ever known. And I thought I must have done something good in a past life to have this Karma now. We had such a great relationship playing her Game, that I saw no reason to stop now. She was an adult and I was an adult, and up to now we had nothing but a great, though rather unique, relationship. Needless to say, I began to incorporate this new modality into our sessions immediately.

A couple of weeks passed by and again we fell into a semblance of a routine. The Notes appeared at random times and I was unable to see any specific pattern. However, I did notice the frequency increased once this new modality was introduced. My very untrained psychoanalysis of this Game was that in a way this helped her express her inner needs that seemed to be in conflict with her preconceived concept of a 'good girl' from her childhood. Actually all of us grew up with concepts layered on us at an early age by our society. Some were helpful and many were stifling.

But if I was going to start analyzing Cindy, then I should look at my own glass house as well. All men have fantasies. But not all fantasies are acted upon. Why was I participating in Cindy's Game? Well, the initial answer was she was gorgeous and how in the hell could I turn this down. There is always a power exchange of some sort in any relationship. I was under no illusion that I was not actually driving this car, Cindy was. But the ride was very pleasant. So, I decided to just lean my seat back, turn up the radio, and not worry about where we were going. Just enjoy the scenery.

After our afternoon on the deck and the very sensual shower, we begin to do what most would describe as normal activities together. Once we actually went to the Mall shopping together. We also went to grab a pizza now and then and things seemed normal. We were not dating however. We were just good friends and neighbors. For tonight I told her to dress for dinner. I was taking her out to a nice little Italian place and she should be at my place at 7pm.

Like clockwork I heard her little knock at my door. It had turned into a mini ritual of sorts. When I opened the door, there she was in this tantalizing little sundress. It had those thin little spaghetti straps and a straight cut bodice that showed the tops of her wonderful breasts. As usual, seemingly regardless of what she wore, her hard-little nipples were visible. She looked perfect.

"Come in," I said and gave a slight bow and wave of my hand. She came in and I noticed she held a small package and envelope behind her back. As she walked into the living room her sundress hugged her tight little ass. Just delightful.

"This was at your front door," she said holding out the box, along with the envelope. I smiled and thought this was intriguing. Before I took the box and envelope from her, I lightly brushed the back of my hand against the stiff little nipple on her left breast. "Are these hard all the time?" I asked with a smile.

"Always when I am coming to see you," she said in her small voice. Damn if that didn't stir my cock.

I led her over to the couch and took the box and envelope. The envelope had my name on it as was always the case, but the box was a new thing. I thought this odd, but she always finds a way to energize my curiosity.

The Note said: Cindy's continued chronic issues now require adding additional, more advanced techniques. The item enclosed is self-explanatory and should be used at least one hour prior to any Motivational session. This will Open Up new avenues of Motivational Techniques.

The creativity of this woman apparently was endless. I immediately opened the package. As I looked inside, a smile crossed my face. In the box was a small chrome butt plug and a tube of lubrication. I held up the butt plug and Cindy let out a small little, "Ohhh...my."

Dinner was at 7:00 so I saw no need to waste time. "Cindy, this note says this new technique device should be applied at least on hour prior to any Session. Since a Session is needed this evening, we better apply it now," I said.

"Now?" she said in pleading tone of voice.

"Yes, now," I said. "Take off your panties."

"But, but..." she stammered. "I don't think...I mean not now."

"Yes, now,' I said again, using my stern look that I had mastered since being with Cindy.

She hesitated a moment, then reached under her little sundress and pull down her panties, stepped out of them, and handed them to me.

"Go to Cindy's Place at the couch," I said. I had named the arm of the couch in her honor. I knew secretly she was really pleased with this.

She moved to the couch, bent over Cindy's Place, putting her arms and head on the seat cushion. I brought the plug and the tube of lube over so she could watch as I rubbed the lube generously over and around the shiny butt plug. It glistened. Then I put a large glob of lube on my finger so she could see it. "Raise you dress and spread your legs apart. Wide apart," I said. Her eyes actually did get big. I was not sure if she had tried this plug before giving it to me, but from the apprehensive look on her face she was having second thoughts. But she complied and raised her dress, exposing her naked little behind and all the parts, especially the part that was about to be assaulted. I notice her breathing increased a bit. I smiled.

I went around behind her. "Take your hands and spread open your ass checks," I said in a calm, even voice. She complied, all the time looking at my hand holding the shiny butt plug. My target was now open and ready. I took my finger, with the glob of lube, and just touched her puckered little hole. She bucked ever so slightly, mostly in anticipation, for I just gently rub around her little puckered opening with my finger. Then, ever so slowly, I pushed my slick finger, along with the glob of lube into her ass. I pushed very deliberately until I was all the way in up to my knuckle. She let out a small moan. I then slowly pulled back out, bit by bit. Then back in...back out...back in...back out. I hesitated each time I was completely in and rotated my finger slightly. This lubed finger, slowly fucking her little bum hole, was making her wet. It was easy to look down and see her natural lube glistening between her legs. Then I removed my finger and wasted no time in placing the butt plug up against her well lubed anus. She looked back towards me; her face was flushed. I gently began to push.

She took the butt plug like a pro. Once it was part way in it seemed like her sphincter just sucked it in the rest of the way. She gasped. "Oh my god...it feels so, so, big," she groaned. Her body shuddered. It seemed this was the first time she experienced a plug in her backside. She took a few deep breaths, seemed to relax, and then she turned to me and smiled.

I pulled down her dress, reached for her panties and handed them to her. "Here, you better wear panties tonight," I said with a big grin on my face.

She looked at me and whispered, "You're a bad, bad boy."

On the way to dinner I said, "This is just Cindy and Ted, good friends and neighbors going to grab a bite to eat. OK?"

She smiled and said, "Of course Ted. I really appreciate you taking me to dinner. You know you didn't have to do that, but I greatly appreciate it." The Game was certainly up and running.

When we got to the restaurant we were seated quickly and seemed to be getting a number of employees, all male, helping us with menus, water, etc. I am sure Cindy's dress had something to do with that. We settled in for a nice dinner. As we went over our menus, I noticed Cindy shifting from side to side in her chair. Without looking up from my menu I said very softly, "Having some issues? You act like you have a stick stuck up your ass as the old saying goes."

She looked up and it was the first time I actually recall seeing her blush. Her cheeks began to turn a light shade of red and it traveled down her chest. Then she smiled. I didn't really know the rules, but I felt like I scored a point or two on that one.

"I hear the fish is good," she calmly said.

"Yes, lets do that. I'd like that as well," I said and smiled looking directly at her. She pursed her lips and sent me an air kiss. God, she was something.

We drank wine, ate some fabulous fish, drank wine and had desert. We talked, we laughed, we were just good friends and good neighbors.

I paid the check and we headed home. I tried not to speed, but my anticipation was high. We didn't talk much during the drive home and each time I glanced at Cindy it seemed like she was always adjusting her seat in the car.

When we got back to my condo and I closed the door, Cindy jumped and put her arms around my neck and kissed hard on the lips. I respond and we ate each other face, as they say in the current vernacular.

"Thanks for dinner. It was the best," she said as she buried her head in my chest. She looked up, and returning to the Game. I am ready for my Motivation Session now."

I took her by the hand and went down the hallway to the bedroom. "We will be working on your Motivation in the bedroom tonight," I said as we walked.

"Stand here," I said when we got to the side of the bed. I could see Cindy was somewhat curious. Then I took two pillows and placed them in the middle of the bed, one on top of the other.

When I turned towards her, she had a look that said she understood.

I put my hands on her shoulders and turned her around. I slowly unzipped her little dress. The one that got our water glasses filled constantly by several different bus boys. I let it slip to the floor and she instinctually stepped out of it. I then grabbed her panties and uncerimonislly pulled the down to her feet and off. Taking her hand, I led her towards the bed. She didn't need any instruction and climbed up and position herself over the pillows, her sweet ass sticking up in the air. The little round head of the butt plug sparkled in the dim light.

Then I did something new and I was sure she had not expected. I began to undress. Since I was going to get there shortly, and the vision of a naked Cindy bent over with a sparkling butt plug in her ass was making my cock hurt in the confines of my clothing. Cindy had turned her head and was carefully watching, and I perceived a small smile on her lips. When I was done, I reached in the nightstand and took out the small leather paddled, Cindy's Paddle, and stood beside the bed. She stared at my nakedness, my very erect cock, and the little paddle in my hand. The sexual tension in the room was like some benevolent beast, just lurking, ready to take over.

"Its time to work on your motivation Cindy," I said as I positioned myself on my knees directly behind her wonderful naked backside. I could see she was breathing much faster now. This was new territory for both of us. But she knew. She knew where this would end. And I got the feeling she was both apprehensive and enormously aroused.

I took aim carefully, for I didn't want to hit the little plug in her ass, just the side of the cheeks. I waited...I waited...and then SMACK! The paddle landed just on target. I waited as the outline of the paddle appeared on her white little bottom. I planned to keep her paddling short, for I couldn't take my eyes off the anal plug in her sweet bottom. SMACK! I did the other check. I slowly used this same slow rhythm several times. She let out a little grunt with each smack. They got a bit louder as I progressed.

With the butt plug, her explicit display of her private parts, and the paddling, her juices were actually slowly dripping from her pussy. I knew it was time.

I laid down the paddle so she could see it and gently rubbed her pink cheeks. With my other hand I lightly moved the sparkling knob of the plug around in her ass. She was now breathing heavily and her little moans were in sync with the movements of the plug as I slowly twisted and moved it slightly in and out. Then I began to slow, ever so slowly, pulling the plug from her expanded little hole. She let out a long, loud grown as its bulbous head was halfway out, expanding her anus wide. Then it seems she pushed and it popped right out. "Oh god!" She cried, and let a long moaning sound.

I got up off the bed and went back to the nightstand and picked up the bottle of lube. She turned so she could see what I was doing as I started putting lube all over my very erect cock. It was all I could do to keep form coming right then and there.

As I moved back behind her, I said, "Spread your cheeks for me like a good girl." She didn't hesitate and reached back and pulled them as wide as she could, looking back at me, then down to my glistening cock, and then back at me. I took my cock and placed it gently on her pulsating little hole. Her little sphincter was actually slightly opening and closing in sync with her rapid breathing.

Then slowly, as slowly as I could possibly go, I began to push the tip of my cock into her ass. Cindy let out a low guttural moan as I slowly moved it into her. I kept going. Slowly inching further into her. Slowly...Slowly. Cindy kept saying, in a low voice, "Oh God...oh God..."

Then it was in all the way. I took her hands away from her cheeks and she put them under her head. "Are you OK?" I asked.

"Its...its...so big," she panted. "I'm so full," she groaned. Then she looked back at me. Looking at her face, her eyes, her naked body bent over the pillows, my cock buried in her ass, it was almost more that I could stand. In a low, raspy voice she said, "For God's sake, fuck me. Fuck me in the ass."

I certainly wasn't going to ignore that request. Her words, the look and her face alone were enough to put me over the edge. I had been somewhat afraid I would hurt her, but now the animal instincts were taking over. I began slowly at first for I knew she had to get use to this new invasion. With each slow thrust she moved back to meet me. She wanted it.

I held her hips tightly, trying to move slowly, almost methodically, in and out, in and out, in and out of her ass. She moved from groaning to making animalistic grunts with each slow thrust.

I began to move faster. She started to pushed back hard. I pushed forward and she met each thrust with one of her own. We both were grunting as my body began to slap against her ass check with each thrust. All thoughts of taking it slow were now gone for both of us. We fucked hard. She was getting her request fulfilled. I was fucking her hard in her ass.

Then I noticed her hand between her legs. Her fingers were furiously rubbing her clit, almost attacking her pussy. She then pushed two fingers into her opening and matched my thrusts into her little bum hole. We were now engaged in a wild sexual dance that we each knew was soon to end.

Then I felt it. That point of no return. There is a place where all the will power, all the mind tricks just will not work. The body is taking control. It is going to do what it needs to do. With one last thrust, burying my cock fully deep within her, I cried out and came with an intensity I didn't know existed.

Cindy started yelling, "Yes, Yes, Yes!" It seemed like I just kept pumping my cum into her when she finally cried out, "Oh...My...God...AAGHHH!

My cock was still firmly lodged in her ass and I could feel the contractions begin. It was like her ass was grabbing my still hard cock. And then I felt something spraying on my legs with each contraction. Her juices were being violently pushed out of her pussy and covering both our legs. It was amazing!

As I pulled my cock from her beautiful backside, I just collapsed on the bed next to her. I turned my head and our eyes met. She was breathing hard and her eyes sparkled as she smiled at me, and said in barely a whisper, "You're a bad, bad boy."

I leaned over and kissed her. It was a soft, long, loving kiss.

She grabbed my neck and rolled off her pillows. Our bodies just went together like magnets. We held each other for some time.

After our breathing returned to normal Cindy looked up; her eyes were misty. "What have you done to me? I never, I mean never felt like that before in my life. My whole body...," she said with her voice trailing off. Then she let out a small giggle. "Damn you Ted," she said as she playfully hit me in the chest. "We just maxed out! Nothing is left! You've done all my holes!"

Now we both broke out laughing. I bent forward and kissed her on her sweaty forehead. "Sweetie, I guess we will just have to start over at the beginning."

We pulled the stained comforter off the bad and crawled under the sheets with our sweat, juices, and God knows what else all over us, collapsing into a deep sleep. I knew the morning shower would be interesting and fun.