Jackie's Challenge

Jackie is a beautiful fit woman who has an extensive library of nude selfies and she did not hesitate to share them with me. I still have some. She would also love to walk around her apartment naked making sure the blinds were open so her male neighbors could see. After several conversations about her exhibitionist propensities I decided to test her resolve as a challenge game.

My first test of her defiance was in a piano bar. Jackie wore jeans and black pullover top with no bra. We had been drinking for a while. She was leaning back against the bar with her elbows on the bar and at one point I turned to face her, put my hands on her sides and felt some bare skin exposed because of her position. I slipped my hands under her top and kissed her gently. As I did, I slipped my hands up until I found her bare breasts and her large hard nipples. She gave me a sly smile as if to say “I’ll bet you didn’t know that I wasn’t wearing a bra.” I pretended that I was going to lift her blouse so that I could see her tits. This action would have exposed her to the entire bar.
She grinned and gave me an ‘I dare you!’ defiant look as she leaned back against the bar. I returned the defiance and continued to slowly but deliberately push her top upward mostly in an effort to test her resolve. The guy to my right was now watching the face-off. Locked onto her gaze I could feel the top reaching the bottom of her breasts. She never flinched and her look never changed. As I moved her top to expose her breasts, the material snagged momentarily on her now erect nipples and with a freeing release popped her breasts free of the materials encumbrance as my ascent continued until I was up to the top of her shoulders leaving her breasts completely exposed to our neighboring friend. She never flinched as she stared me down. After a few long second, I let the blouse fall back to its original position.

Another opportunity to test her was an evening we were out to the theater. I bought Jackie a very sexy dress with a slit up to the top of her thigh. That dress and her heels were all she was wearing and she made it a point to let me know several times during the evening.
After the theater we went to have a few cocktails and an appetizer at a nice upscale restaurant. Given the hour of out arrival the restaurant was not very busy. Jackie and I sat at a table across from the bar, talked and drank. She made it a point of reminding me again she had nothing on under the dress. “I want the dress back!” I announced with a sly look. “Fine! She said defiantly, give me your jacket!” she commanded. I smiled as I handed her my jacket fully expecting her to go to the ladies’ room and take off the dress. She didn’t do that. Instead, she slipped my jacket over the dress and covertly removed the dress while using my jacket to conceal her activities. Once the dress was off, she slipped her arms into my suit jacket, close it and with a smug smile handed me her dress. “You know I’m going to want my jacket back before we reach the car. Its chilly outside.” “Fine!” was her defiant reply. She sat naked, save my jacket and her heels, until we finished our drinks. I signaled the waiter who brought the check. By the look on his face, he noticed Jackie’s change of wardrobe although she was completely covered. I paid the check and stood offering my hand to Jackie. She took it, stood and still holding the jacket closed with one hand she used her other hand to hold my hand following me to the door. “The valet ticket is in the inside breast pocket.” I informed her.

She reached in and handed it to me and I handed it to the valet. The remaining valet noticed Jackie’s odd attire and wasn’t sure if that’s all she wore. The car pulled up to us and the remaining valet opened her door. I moved behind her as the valet looked at the both of us and said “let me take this jacket for you baby!’ Jackie released her hold of the front of the jacket and I removed it from her shoulders leaving her completely naked except for her heels. Unfazed she moved her slender muscular body elegantly forward and slipped into the passenger seat with stunned valets looking on. I moved around to the driver side and tipping the remaining valet got in. Jackie’s door was just closing. As I pulled away from the curb. Jackie laughed in excitement as I handed her my jacket and she put it on once again.

The Lake
I was determined to get Jackie to cave and tell me I won at our game. My opportunity came at the lake one beautiful summer evening. We sat on a bench looking at the water and the stars as we talked. A guy appeared and walked past us a few times. Standing I took Jackie by the hand and walked her to a dock about 30 feet away. When we reached the shoreline, our new voyeur was watching us from the bench we just vacated. Since Jackie’s back was to him, she didn’t see him so I mentioned to her that he was watching us. She shrugged it off. I began to unbutton her blouse once again earning her look of defiance. Once unbuttoned I pushed it off her shoulders where she dropped her arms to allow me to take it off. After laying it on the dock I unbuttoned her jeans and pulled down the zipper. I knelt and removed her shoes and returned to focus on her jeans. “he’s still watching” I confirmed, hesitated for her reaction and not receiving one pushed her jeans over her hips and round butt until they fell to her ankles. Once again, I knelt to pull the jeans off her.
She stood before me even more defiant in her black bra and panties. I reached around her back and unfastened her bra and slipped it off her shoulders discarding it on the growing pile of clothes. I stooed once again waiting for her to say ‘enough’. It didn’t come so reaching for her panties took hold and looking her in the eyes began to push them off. Still no reaction from her as they cleared her ass and fell to her feet. This time she stepped out of them and kicked them off to the side. She was naked and still not conceding defeat. I continued to search for new ways to get her to tell me to quit so I turned her to face her admirer. She looked st him and stood completely naked to his gaze. After a few minutes I whispered to her to lay on the dock. She laid on her discarded clothes and standing at her feet I opened my jeans pushing them to my knees and knelt at her feet. I pushed her knees spreading her legs then leaned forward and fucked her while out audience watched. I watched her face as the defiance left and a look of nervousness surfaced. I could tell she was getting ready to orgasm and I hoped that him seeing her do that would cause her to stop me. It didn’t. I and our friend watcher her orgasm. I came deep inside her. When we were finished, she stood facing the stranger proud that he had seen her performance and dressed.
She won. I never tested her again because I think she got off when I did that to her and frankly i think she has no limits. I have some of her selfies and some pictures that I took if you want to see her. Smittychris4@gmail.com

1 month ago

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