Annie's Training Pt. 02

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An older man continues to train a younger woman.
7.4k words
4.72
16.7k
14

Part 2 of the 3 part series

Updated 08/23/2023
Created 03/25/2023
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This is my first attempt at a longer story, one that seems to be coming out in instalments.

In this one, Mr. Illanovitch's work with Annie continues, now inside the cabin. It also includes some backstory to the first in this series, Annie's Training Begins.

Both stories involve a college-aged woman and an older man, include light bondage, are set in a rural area, and depict a developing erotic relationship.

All characters depicted are consenting adults.

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Annie slowly came to her senses as Mr. Illanovitch held her. She felt light-headed still, her heart pounding and her breathing just starting to slow. She couldn't believe he'd provoked such feelings in her and brought her to such a peak, like nothing she'd ever experienced before. How could she have submitted herself to him so completely, so willingly and with such abandon? How was that possible?

She'd only just started college. She had imagined that if she sex at all, it would be more like what she'd had in high school: fumbling awkwardness and tentative uncertainty; then a rushed fucking that put a stupid grin on the boy's face but only left her feeling unsatisfied and sore. And while she had been happy to help satisfy two different boyfriends this way a few times, she had thought at college she would find someone who was two or three years older, someone with more experience, someone who could also satisfy her. She had hoped for something more romantic, maybe something that lasted for a year or two, something that actually involved love. Maybe not permanent, the guy probably wouldn't be the one, but it would involve something deeper than she'd encountered so far. She would learn about herself and her sexuality and if her desires would fit with another's likes and needs. It would be a real relationship, sexually and in other ways too. Having an experience like that was part of being in college.

But what happened just now wasn't like anything she'd anticipated.

As these thoughts passed through her mind, she felt Mr. Illanovitch slowly ease himself away. She wanted to hold on to him. But she couldn't. She suddenly felt cold and uncomfortable. The rope binding her to the porch was starting to hurt her arms. A gust lifted the hem of her sundress and reminded her of what he'd done with her panties.

She squirmed a little. "Ummmm ...?" she tentatively said, glancing up at him.

She saw him understand her discomfort immediately. He moved behind her, and with the same expert ease he bound her, he now set her free. Annie watched him retrieve her tights and wet panties from the ground.

"Come inside," he said, taking her hand and helping her up the porch stairs of the cabin. "I'll light a fire."

He settled her into the big rocking chair and brought a blanket. Annie pulled her legs up and wrapped her arms around them, cocooning under the warm cover. He turned to the old black wood stove and soon had a fire crackling in the firebox. She watched him fill the kettle with water from a jug on the counter, and set it back on the cast iron top of the stove. He pulled a couple of mugs down from a shelf and opened a tin container that was on the counter.

He looked at her with a smile. "Some tea?" he asked. "Earl Grey, OK?"

Annie nodded. "My favorite." While he made the tea, her mind replayed how she had ended up here with him.

A week ago, her two roommates, Pen and Norah, had convinced her to get away with them for the Easter break. Being poor starving students, they planned a cheap and simple trip to the rural area where Billy and his best friend, Tom, had grown up together and where both of their families still lived. She felt like a fifth wheel for much of the time so far. Billy obviously had the hots for Pen, Norah and Tom were already an item. Their in-jokes and teasing left her feeling kind of alone, like she was looking in from the outside.

Billy's parents hosted a party while they were there. They and Tom's parents were both really nice and welcoming. And Annie was happy to meet and chat with some of the other guests. Everyone was having a good time and a little loose from the drinks they were enjoying. The party atmosphere was encouraged by the beautiful modern open concept house.

When she first saw Mr. Illanovitch, she had found him attractive but not drop-your-panties gorgeous. He didn't notice her at first. She had tagged along when her four friends went into the study. Mr. Illanovitch was tending the bar there. Billy introduced him as a long-time friend of his family's. The older man's gentle brown eyes and comfortable poise caught Annie's interest. He was trim and fit, almost athletic. She wondered if he was a runner. When they were introduced and his eyes met hers she looked away immediately. But she felt something. What was it that made her curious and put a surprising little flutter of butterflies in her tummy? When the others announced they were going to go for a swim in the pool, she decided to stay in the library.

She'd ended up spending the rest of the party with him. Soon she was helping as if she was an apprentice mixologist. He had an astounding memory for making a wide variety of drinks that used many of the unfamiliar bottles on the shelves behind the bar. It was all new to her. Annie's folks were not party people and hardly drank any alcohol.

Mr. Illanovitch was a good teacher, clear with his directions, and never annoyed when she was slow or uncertain. He treated her like she was a real help, even though she probably got in his way sometimes. She found it easy to follow his lead, to take his instruction and to try her best to do what he asked. She'd liked being beside him, aware of his body's movements, learning when to stay out his way or when it was OK to move closer, to reach across his arm for a lemon slice while he stirred a new concoction.

The evening passed quickly. Between serving drink requests, she learned a little more about him and he of her. She was flattered by his attention and although he was much older - he could easily have been her father - he treated her like an equal. And it was like he was really interested in her and he did really want to hear the answers she gave to his questions. His gentle probing encouraged her to open up. She had found herself becoming more and more talkative and at ease with him.

Annie learned that Mark, Mr. Illanovitch's first name, had recently retired from a career as an investment broker. He had known the party's hosts, Billy's parents, since their college days. Annie had described the boyfriend and girlfriend connections among Billy and Pen, Tom and Norah, and her own relationship status, unattached. He had told her a bit about his past. It turned out that he and Billy's mom, Sandra, were hot and heavy for a couple of years back in their own college days. But Graham, Billy's dad, who had been Mr. Illanovitch's best friend from high school, wooed Sandra away when Mark was gone for a semester abroad in Ireland. Mr. Illanovitch had just shrugged when Annie asked how it was that they all could still be close after his own best friend had stolen his girlfriend away. "It happens," was all he had said with a laugh. "And time heals many things."

When he asked about her background, she told him that she'd come from Montana to go to college. She had grown up on her family's ranch there. She had two older brothers who both worked with their father running the place. They had over 10,000 acres and about 1,000 head of cattle. She had grown up outdoors, always running after her brothers and needing them to rescue her when she couldn't do everything they did. She wasn't a tomboy though and, being their little sister and the only girl in the family, they doted on her and tried their best to keep her out of trouble. Her mother had passed away from cancer when she was quite young. Her father was stern and not especially affectionate. When he gave an order, you had to jump to do his bidding. Between her brothers and father, Annie had grown up eager to do whatever pleased them and to try anything they were willing to let her do.

He had asked about what she was studying and Annie told him that horses were her passion. She was seriously thinking of going into veterinary medicine, if she could just get through organic chemistry. She loved to ride and was comfortable both with western saddles and working the cattle as well as with formal English riding, dressage, and jumping. She had practically learned to ride before she learned to walk. They had a deep conversation about the relative merits of different breeds, stories about relationships they'd had with various horses, and the skills one needed to be able to develop the bond one could have with them.

Mr. Illanovitch had told her that he kept a small stable on his hobby farm. When he described it and talked about the horses he kept, her heart had leapt thinking of the possibility she might be able to spend some time with them. Maybe she unconsciously communicated that she wanted him to ask her to go for a ride.

When the party was over he offered to drive her to Tom's parent's place where she was staying. Her friends had disappeared sometime during the evening and she was secretly pleased. She was happy to have been with Mr. Illanovitch. She felt completely comfortable with him and was happy to accept the ride.

Annie recalled that after they had said their goodbyes to the party hosts, it felt good when Mr. Illanovitch had walked beside her. He had taken her arm when she wobbled at the bottom of the steps. They had both laughed and he had put his hand on Annie's back, guiding her with gentle direction to the line of cars and SUVs parked on the lawn beside the house. She remembered how she had found his warm hand pleasant and how secure she felt as she allowed herself to be guided.

When he had steered her toward a small green boxy convertible, she remembered giggling, "It's so cute!" Mr. Illanovitch had led her to the left side of the car, which, in North American cars, was where the driver sat. "What? You want me to drive?" she had asked.

He had chuckled and pointed out that the left side was the passenger side in this car, explaining that it was a Triumph TR6, a British make. The driver and the steering wheel were on the right side of the car. She had felt stupid for not realizing it on her own.

He had opened the door like a gentleman and waited until she settled in the low car. He leaned over her since the top was folded down and reached beside her thigh for the ends of the lap belt to pull it across her hips and tug the end tight. Annie had felt a touch of excitement as he did. He was so close she could feel the warmth of his body and she almost jumped when he brushed her leg while reaching for the belt buckle. When he pulled it tight around her she had felt herself melt into the pleasure of his authority.

The note of the engine's exhaust growled when they pulled away. It impressed her and she had told him so. It turned out that Mr. Illanovitch was not only a skilled mixologist, but also a skilled mechanic. He had restored the fifty year old car himself.

Mr. Illanovitch was not a timid driver. She smiled to herself remembering her excitement at the wind whipping around them as they picked up speed on the pavement. She had screamed when he threw the little green car hard enough into a corner that the tires complained. Unconsciously she had reached across to clutch his thigh when her weight shifted. She remembered half shrieking and half laughing when the road rapidly cornered in the other direction. Then, they accelerated down a straight stretch toward a rapidly approaching Tee intersection. Annie remembered grabbing the dash and squealing, "Stop!" Mr. Illanovitch had stepped hard on the brakes, throwing her against the seat belt as he brought the car to a perfectly controlled halt exactly level with the stop sign.

He was grinning when she opened her eyes and turned her astonished face to him. Her heart was pounding, she remembered. She had thought she was going to die. He had grinned and said, "Isn't that fun!?" Annie remembered laughing, partly from relief, partly from the rush, and partly from knowing he was right, it was fun!

Afterwards he had driven more sedately until he turned off the pavement into the driveway of a fashionable and tasteful older home. Mr. Illanovitch stopped the car at the front door. They exchanged their thanks for the evening, for the drive, and for being such good company. She had unbuckled her seat belt and leaned across to give his cheek a quick peck. Annie had found him charming.

Then, as she was about to go up the front steps he had asked if she would like to come out to his farm, to see the horses, and to go for a ride. She had thought for a nano-second before excitedly answering, "Yes!" They agreed on a time when he would pick her up.

And now here they were. She'd seen a bit of the farm and had gone for a wonderful ride. And, good lord, she had just experienced the most amazing orgasm from a man who she hardly knew but who somehow was able to put her into a position that made her feel incredible.

Now, here in this isolated cabin, Annie was snuggling under a warm blanket and watching him tidy up things around the room while waiting for the tea to steep.

When it was ready, Mr. Illanovitch carried the mug over and set it on the little table beside her. She watched him pull a round stump of firewood in front of the stove. It was worn smooth and clearly had been used for a long time. He sat on it and poked at the fire before sipping the tea and resting his elbows on his knees.

Annie took a sip of hers, savouring its aromatic flavor.

"Tea alright?" he asked.

She nodded. "Perfect."

They sat in silence. Only the crackle of wood in the fire box disturbed the quiet.

Annie found herself relaxing. Only hazily did she keep having thoughts about what might be in store now. She sighed and decided there was nothing worth worrying about. What had happened had happened. It was just a natural connection between a man and a woman, though in this case an older man and a younger woman of course. Maybe it had been influenced by what had gone before, the party, the ride in his car, the first encounter with the horses, the ride, and being in this isolated and private setting. But it didn't really matter. She sighed again and sipped more of her tea.

He finally broke the silence. "Annie ...."

She looked up and smiled.

"I said before that I didn't want to hurt you. I want to be sure I didn't. Are you OK?"

She nodded. "Yes. I feel fine," she answered automatically.

He turned to regard her more directly. "No. I mean, I was fairly forceful before. I just want to be sure I didn't cause any pain." Mr. Illanovitch raised his eyebrows in question.

Annie scanned her body. Despite having been tied firmly to the porch, she didn't feel any soreness from the rope. She focused on her pubic area. It had been manipulated in entirely new and different ways. But she wasn't feeling any pain. Even where he had pulled her panties tight against her perineum, she felt no discomfort. All that bothered her was the feeling she needed a shower, just to wash away the dry remains of her fluids.

Annie felt comfortable meeting his eye. "I feel fine, really," she said. "No injury."

He smiled. "Good," he said. She could see him relax.

Then he looked at her quizzically again. "And mentally? How do you feel?"

Annie nodded. She had already replayed the experience in her mind and gone back over everything they'd done since she met him. She knew she didn't feel any horror or distaste for what had happened. She knew she still found him caring and easy to be with. She knew she still found him attractive and even found his ability to control her both comforting and exciting.

She smiled shyly. "I'm fine." She went on, "In fact, I'm better than fine."

Annie turned to meet his gaze directly. In a small voice she said, "Mr. Illanovitch, you made me feel things I've never felt, and it was wonderful. You gave me an experience I've never had before. My heart was pounding. I was nervous and a little scared. But you made me feel so good."

She paused, lowering her eyes. "I've never ever had an orgasm like that." She looked up to meet his eyes, "It was amazing!"

She watched him nod, a small smile on his lips. "Good," he said. "I'm glad. That's what I wanted." He grinned, "I certainly did not want to drive a wedge between us. Between my young filly and me!"

She opened her mouth in surprise. "Young filly!?" she gasped. He had said something about training a filly earlier. "What?" she asked quizzically. "Is that what I am?"

The corners of his eyes crinkled. "No. Not at all. You are so much more than that! Much more!"

She was puzzled. "So then, why ...?"

"Well ..." he regarded her with his gentle brown eyes, "... I do want to treat you as a young filly ... a young one who needs gentle training to become her best."

Annie's heart quickened with her intake of breath. Once again she felt herself drawn to this man.

He paused and then looked at her intensely. "Do you agree?"

He didn't wait for her answer, but went on. "It's what I want. You probably sense that already. You are so young and unvarnished, shy and uncertain, but also eager and curious. You are very much like a young filly who needs training. But like I said, I don't want to hurt you or harm you. I want you to learn as much as I'm ready to teach you. You can trust me."

He paused. "So, yes, I want to train you like I would a young filly."

He waited, studying her.

She knew her face showed the uncertainty she felt. It was exactly as he said. She was young, unpolished, a little afraid, and unsure. But she was also attracted to him and, oh god, the way he'd made her feel. Could she feel like that again? The butterflies appeared again and she felt her heart start to pound. Just the thought of him and what he might do made her nipples stiffen. She could feel them rising and was glad for the blanket or her body would have betrayed her. Her lips parted and she felt tingling between her legs. Damn. No matter what she thought rationally, her body was saying yes. Yes, she did want to learn. Yes, she wanted to be open to him. Yes, she wanted to give herself to him. Yes, she wanted him to do whatever he wanted with her. Yes, she wanted to be trained like she was a young filly.

She nodded slowly.

He lifted a questioning eyebrow. "What?"

Annie swallowed. "Yes," she whispered. "Yes, I want you to train me."

'O god ...,' she thought again, '... what am I saying?'

He nodded. "You accept my control?"

Annie nodded again. "Yes .... yes ... sir."

He went on, "I will restrain you again at times. I will do what I want with your body. But I will listen to you, to your reactions, your responses, and to your voice. If ever you want me to stop, just say so. You are too beautiful and precious to be harmed."

"OK?" he asked again. "Do you accept?"

Annie paused for just a moment. Looking into his soft brown eyes, she whispered, "Yes ... sir. I accept."

"Good," he said.

He stood up like their business was finished. "More tea?" he asked.

Annie said, "No ... no, thanks. I'm fine." She paused. "But.. what I would like.. is a shower."

He shook his head and smiled sadly. "I can't provide that, Annie. I'm afraid there's no running water in the cabin. Just a hand pump at the well outside. And, as you know, there's only an outhouse for bathroom facilities."

She nodded, "I understand." She shifted in the big rocking chair.

He thought for a minute. Then he asked, "Perhaps I can warm some water on the stove for you. Will that help?"

Annie said immediately. "Yes, please ... sir. Yes, that would be nice."

He refilled the kettle. Putting it back on the wood stove, he knelt down and added more wood to the fire box, stoking it up. It caught immediately and soon the old blackened stove began to creak as it warmed up.