Annie Ir

Annie Kirk: Chapter 1

"Painful Pleasure"

Note: the Annie Kirk series is not a sequential story. They are short stories inspired by someone close to me. The stories reflected my fantasies of her and evolved to her sending me erotic pictures that I used as inspiration for different stories. These stories are inspired either by such imagery or real-life elements. This story was an original fantasy but is not a description of real events.

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Annie anxiously awaited his arrival. They had been talking, texting, and emailing for a couple of weeks. She couldn't contain her excitement to see him again. They had met once briefly for a drink, which was enough for her to know she was as attracted to him physically as she was mentally. The kiss goodbye sealed the deal. She looked up at him showing complete vulnerability in her eyes. He knew he had her then.

Their conversations since continued to draw her closer to him and her desire to be with him was growing each day. The erotic stories he wrote and sent to her stirred her desires. She wasn't sure she would be able to resist him when they met; she wasn't sure she wanted to.

There were no specific plans. She would meet him in the lobby of his hotel, and they agreed to let things just play out. He seemed to be as excited to see her as she was him, but there was a twinge of anxiety. What if he changed his mind about her? What if he decided he didn't want to do this?

Her face lit up as she saw him casually walking toward her. Arms outreached for a hug, he said, "Annie, you made it. I'm so glad to see you. I was afraid you might change your mind." Apparently, he was thinking that she might be having second thoughts as well. He engulfed her in his arms and pressed her tightly against his body. She really liked being close to him.

"Shall we have something to drink at the bar, or did you have something else in mind?" he asked.

She didn't say what she really wanted; she was afraid of being too forward or giving it up too soon. "Sure, that sounds great," Annie responded.

They chatted on various topics while the server took their order and delivered their glasses of wine. They raised their glasses in a toast, "cheers" they said in unison.

"So, I'm really glad that we were able to get together tonight because I won't be able to keep our plans for this week. Something came up that I have to take care of," he said.

Annie wasn't concerned. She was happy to be here and looked forward to their evening together.

"However," he added, "I did have something planned for Wednesday that I think you might like to hear about even if we aren't meeting that day. Interested?" he asked.

"Of course," Annie said. "I enjoy your imagination."

"Okay, here goes. So, I planned for us to meet at lunch. It would be a regular lunch. But after we ordered, I was going to say to you, that I want your panties. You can either take them off right here at the table, or you can go to the ladies' room and bring them back to me. Either way, I want them now."

"I was going to leave you the choice of whether you felt comfortable doing it at the table, but I was really hoping that you would just remove them right there and set them on the table."

Annie loved the thought of being without panties at the table. Taking them off right there would be so exciting. She wasn't sure what she would do if he asked. "Ohhhh, that's sooo naughty," she said in her sexy South African accent.

He continued, "after lunch, we would drive in my car to a hotel a few blocks away. The place where we were eating was booked," he explained.

"On the way over, I would gently rub the inside of your thighs, slowly sliding my hand from your knee up under your dress, but not quite all the way." Annie briefly closed her eyes to imagine his hand on her thigh, her pussy tingled, and she almost instinctively started to open her legs at the table.

He continued, which prompted her to open her eyes. "Once in the elevator, I would press you against the wall with my body and kiss you hard, all the way until the bell rang for our floor."

"Oh my," she thought. She felt herself lean in closer to hear his hushed tones.

"Once in the door," he continued, "I would press you back against the door and continue kissing you passionately." He stopped briefly to look into her eyes gauging her reaction. He could tell she was totally into the story.

"Then, I would grab both of your wrists, and pin them above your head while pressing you against the door with my body." Her eyes flickered as she was getting lost in her imagination. "Holding both hands above your head with my left hand, I would explore your body with my right. Slowly tracing down your check, around your ear, down your neck, and stopping on your left breast. Gently squeezing and pressing down on your nipple to get it hard."

Annie was starting to squirm in her seat as he was describing the scene. She could almost feel his touch on her skin and her tongue was subconsciously swirling in her mouth as she imagined them kissing.

He continued, "and because I had you remove your panties at the restaurant, I would have easy access to your pussy. So, still holding your wrists above your head, I would slide my right hand between your legs to find your clit. I would expect you to be soaking wet so there would be plenty of lubricant to play with your clit."

"Oh My God," Annie thought. She was starting to breathe heavy at the thought of him teasing her clit. She was flowing wet right there in her chair.

She was almost unaware of him continuing, "then I would use both my feet to spread your legs wide, keeping you pressed against the door. With your legs open, I could slide my fingers in and out of your pussy. I would expect you to be pretty close to orgasm by this point. So, my plan was to stop."

"What?!?" she blurted out. "You can't just stop there!"

"Not for good," he said with a big smile. Clearly pleased his story had the desired effect, he continued. "We'd walk away from the door toward the bed. But I'd stop before getting to the bed. I would remove your dress and have you stand completely naked in the middle of the room. I would tell you to spread your legs wide as I walked to the closet. Returning from the closet with the tie from the robe, I would take your hands, pull them behind your back and tie your wrists together."

At this point, Annie was completely in heat. Her pussy was dripping wet, her breathing was short and fast, and she knew, no matter what her prior thoughts about the day were, she would give herself to him completely today if given the opportunity.

"I would walk around you, slowly. Making you wonder what I would do next. I would trace my fingers along your back, down the back of your legs, up the inside of your thighs, across your stomach and over your chest, going around all of the places you will so desperately want me to touch. I would do it over and over, getting closer each time to touching your ass, your pussy and your nipples. And then from behind you, I would reach in front of you and play with both your nipples at the same time. Squeezing them, pulling them, feeling how hard they get. Stepping back slightly, I would spank you first on the left and then on the right side of your ass. The crisp contact causing you to whine."

"Excuse me sir, would either of you like another glass of wine?" asked their server. Without looking up, both of them immediately said, "No, no, we're good."

"We're fine," he said. "Thank you."

Looking right into her eyes, he asked Annie, "then I would ask you, did you like that, and would you like me to do it again?" He paused, waiting for her to answer.

"Yes," she whispered. "Yes, I would like that."

"Very well then," he said. "I would spank you several more times on each side, progressively harder. And when your skin was red and burning, I would lightly trace my fingers over the sensitive skin."

Annie felt her clit swell and she wanted to reach down and play with it right there at the bar. She wanted him to take her upstairs right now, but she was paralyzed by the current story.

"Then I would kneel down in front of you, spread the lips of your pussy and suck your clit into my mouth. I would suck it in and out and circle it with my tongue. While my tongue was working on your clit, I would slide my finger inside you to fuck you with my finger while sucking and licking your clit. I would expect that you would be ready to cum within minutes and that your legs would be shaking."

"I would then sit on the end of the bed, remove my pants and shirt, and have you kneel in front of me to suck my cock. Your hands would still be tied behind your back so you would only have your mouth to use."

Annie interrupted, "okay, you have to stop. You have to take me upstairs right now. I can't take this. My pussy is on fire."

Annie didn't remember him paying the bill or the way to the hotel room. Next thing she remembered was opening her eyes and looking over at the mirror on the wall. She lay face down, her arms stretched out in front of her, a wad of the sheets held tightly in her mouth to muffle her screams as he slowly fucked her doggy style. His cock was almost too big for her pussy. It stretched her walls and pushed deep into her. She was lost in ecstasy as the pleasure of him fucking her mixed with the pain of his big cock pressing deeply into her pussy. She didn't know how many times she had cum, but she knew it wasn't over yet and she also knew that this was not the last time they would be together.....