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Obsession - Part 5

"Eileen experiences her first pain/pleasure combo as a Submissive."

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Author's Notes

"Due to a mix-up, Parts 5 and 6 might be submitted out of order. <p> [ADVERT] </p> My bad. Please read part 5 before part 6."

When Friday came, Jake and Eileen went to the pub for a nice casual meal and a drink before going to the movies. They picked seats at the back of the theater, which was nearly empty, pulled up the armrest, and snuggled, his arm around her and her head resting on his shoulder. Jake turned to Eileen and kissed her. She responded by kissing him back, and soon they were making out passionately. Eileen was loving this dating part of their relationship and was sure he loved her, though he'd never said it. Before long, Jake ran his free hand to the hem of her skirt and slid his hand under, running it up to her panties. Eileen spread her legs to accommodate him as she kissed him harder.

With no one around or behind them, Jake hooked the edge of her panties at her crotch and moved it aside, exposing her pussy, which he touched with his finger. He probed her slit and opened her lips, caressing her up and down easily since she was already wet from the arousal of their kissing. She loved the feel of his fingers, and when he slipped a finger into her, she moaned loudly. She adjusted in her seat to make more room for Jake to play. He began sliding his finger in and out of her vagina, and used his thumb to rub her clitoris. Eileen squirmed in delight at his touch, and kissed him all the more passionately. They continued to kiss while he caressed her clit, and she squirmed in her seat, experiencing sexual heaven.

Suddenly, Jake slowed and stopped.

“You know, this movie isn't very good, and we'd be more comfortable at my place. Do you want to go?” he asked.

“Yes, please,” she moaned, sorry for the interruption but happy to know they'd continue in the comfort of Jake's apartment.

So he pulled his hand from under her skirt, and she reset her panties over her sopping pussy. They got up, left the theater, and walked to Jake's place.

“That was such fun! Can we continue?” Eileen said as they arrived.

“That's my plan. Let's sit on the sofa,” Jake replied.

So they got wine and beer and sat together on the sofa. Eileen pulled her panties off from under her skirt and sat on Jake's lap, surprising him.

“Well, this is new!' he said.

“Yes. And I'm ready to pick up where we left off,” she answered coyly.

At that happy cue, Jake slid his hand under her skirt and found her very wet snatch all ready for him. His fingers roamed over and around her muff for a moment, sending waves of anticipation through Eileen.

“I see you forgot to shave today,” Jake commented.

“I'm sorry. I ran out of time getting ready for work this morning.”

“And I'm sorry that I will have to discipline you the next time we go to the Playroom.”

“Okay, whatever, but please continue what you're doing!”

Jake wasted no time in diddling Eileen again, using his fingers to rub the folds of her slit, and caressing her clit with each pass. She was enjoying his play as much as ever, and opened her legs to give him easier access. She was thrilled when he inserted a finger into her again, and she began to rock on his lap, pressing her pussy against his hand. Jake continued to finger-fuck her until she was moaning and squirming with abandon, and nearing her climax. He added a second finger, probed deeper into her, and decided he'd give her a little extra push over the edge. He pressed against the upper inside of her vagina and started a “come here” motion that focused friction and pressure on her G-spot. She went wild with the unbearably intense feeling of it. Eileen bucked and jerked on his lap, screaming with pleasure, and soon came with a fantastic orgasm, her juices running freely from her pussy onto his fingers, her skirt, and Jake's jeans. She kissed him with as much passion as she ever had.

Jake was pleased that he had given her such a wonderful release to make up for her frustration when he stopped his diddling at the theater. He hugged and kissed her as she came down from her ecstasy.

“Let's go to the Playroom,” he said.

“Okay,” she answered happily.

Eileen sat there for a moment before remembering that she was to go in first and get ready. She kissed him, got off his lap, and headed to the Playroom. Inside, she took her clothes off, set them aside, and stood in the middle of the room, naked. Jake entered a moment later.

“Go to The Table, please," he said.

“Yes, Master,” she replied, recalling now that he said he would discipline her the next time they were here, and this was that time. She wasn't sure what to expect but knew whatever he did to her, he would follow up with comforting her. She figured she could endure his discipline by thinking of that, just as he told her to do.

Eileen walked to the massage table, knelt on the knee pads, and bent over, resting her body on the padding atop the table. Jake went to the small table, got a paddle, and returned.

“This is your discipline for not keeping your pubic hair shaved, displeasing your Master,” he said. “You have permission to speak to tell me if it hurts too much. Are you ready?”

“Yes, Master,” she replied.

Jake caressed her rear gently, gave her a little pinch, and then smacked each cheek with the paddle. Eileen flinched a little with that first spank, but it didn't hurt much. Jake continued with another whack on each cheek, a little harder this time. Three more spanks followed in quick succession, each stinging more than the last. They hurt, but the thought of his comforting her afterward helped her think past the pain. Jake administered another five whacks to each cheek, causing Eileen's rear to become a deep pink, and the pain level increased enough to bring a tear to her eyes. She hoped he was done, or she'd have to ask him to stop. As if he could read her mind, he stopped.

“I hope you've learned your lesson and will keep yourself shaved to please me,” he said.

“Yes, Master,” she replied with relief that it was over.

Jake got a bottle of aloe lotion from the bin alongside the massage table and squirted some on his hand before massaging it into her rear. The relief was wonderful, and the gentle rubs were exactly what she hoped he would do for her to comfort her pain. He continued to caress her cheeks for several minutes, and she realized that it was turning her on again. She decided she could put up with most any discipline if this sexy comforting would follow. Jake stopped when she was totally relaxed, and her cheeks were returning to normal.

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“Now go to The Step, please,” he requested.

“Yes, Master.”

Eileen walked to the Step and got on top of its short height, then waited while Jake went to the small table. He returned with the lashes connected by a strap, which he had adjusted for her once before. She held her hands out in front of her, and Jake put the lashes around her wrists. Then he draped the strap over the hook in the ceiling above, which held her arms above her head.

“Spread your legs.”

“Yes, Master,” she replied and opened her legs.

Jake pulled her feet a little further apart and put one of the lashes from the ends of the step around each ankle. Then Jake made sure the lashes on her wrists were pulled almost tight, but left just a little wiggle room for her arms to move.

“You look lovely in this position, my Sub,” he told her. “Wait here a moment while I retrieve some things I'll need.”

“Yes, Master,” she said with a laugh, since waiting there was the only thing she could do.

When Jake returned, he stood behind her and reached around her to touch her breasts, which he cupped and fondled. It was arousing for Eileen, and the helpless position she was in made it much more exciting. He kissed her neck as he pinched and tweaked her nipples with his fingers. She was getting turned on by his nipple play and was enjoying things at The Step so far. Then Jake took a red plastic clip from his pocket, which looked rather like a small clothespin. When he attached it to her right nipple, it hurt quite a lot. He did the same for her left nipple with a second clip, and again, it hurt, but she wanted to accept the pain because it pleased him. It was almost a turn-on to know that not only was she pleasing the man she loved, but the discomfort would be followed by his comforting her afterward.

Soon, Jake moved his hands to her legs, running his fingers from her knees up her spread legs, tracing his nails along her inner thighs toward her open crotch. She loved the tickly feel of those fingers on her, knowing where he was headed. The arousal of his hands made her forget about the clips on her nipples, and the pain had subsided a lot anyway as her body got used to their pinch. Soon his hands reached her pussy, and he ran his fingers up her slit. She was wet from the anticipation of what he'd do, which allowed him to easily caress her soft folds and sensitive clitoris. She flinched at his first touch to her clit; her helpless position, and maybe even the nipple clips, enhanced the intensity of the feeling.

When he slid a finger into her, she had a moment where she thought she'd cum immediately, but it passed as he added a second finger and began to finger-fuck her, in and out. She loved what he was doing to her body, and all her feelings were centered on her pussy. She squirmed as much as she could, swaying her torso to press her pussy against his fingers, and she knew her climax would be coming soon if he kept it up. But then he stopped.

Jake pulled his fingers out and dropped his pants and briefs to the floor. He slapped her pussy a few times with an upward swing of his penis, then pressed himself up and into her. His penis was bigger than his two fingers, and Eileen noticed the difference right away. Jake pumped into her with upward thrusts, and Eileen resumed pushing her pussy against him. He sped up his pumping, causing her to moan in pleasure as he fucked her with passion.

Before long, Jake reached his climax and started to jerk, repeatedly squirting his semen into her. She felt the warmth, and it pushed her over the edge. The need he created in her with his fingers on her pussy, plus the feel of his penis in her and the warmth now filling her vagina, combined to make her cum with another wonderful orgasm. Her juices drained from her pussy when he pulled out of her, dripping to the step below. Jake took the strap off the hook and undid the lashes at her feet. Her arms felt odd being free again as she let them hang at her sides, allowing the blood to return. In the excitement of her arousal and orgasm, she had forgotten about the clips on her nipples until he reached for them and took them off, which caused them to hurt quite a lot. But true to his word, he quickly kissed each nipple and caressed them gently, relieving most of the pain.

After they cleaned up, they left the Playroom and went to the sofa to finish the drinks they left there.

“Well, how do you feel?” he asked her.

“Wonderful!” she exclaimed. “The nipple clips hurt going on and coming off, but I forgot about them as you played with me, and you comforted me afterward, which felt good. I was also concerned about the discipline, and you were firm when you paddled me, but the lotion afterward comforted me and made it alright.”

“I'm glad to hear you say that. I will want to use a little pain like the nipple clips to increase your arousal for whatever we do in the Playroom. Today was a good test of that, and you were brave and passed beautifully. I'm proud of you, my Sub!”

They finished their drinks, and Jake walked Eileen home, giving her a long kiss at her door. After leaving, he walked home, thinking about how lucky he was that Eileen came into his life, a pretty girl willing to have sex on his terms. So far, she was everything he wanted, and he looked forward to more progress with her as his Sub. He was wondering if maybe he loved her.

Eileen sat in her living room, sipping another white wine and thinking about Jake. She was obsessed with him all through high school, and now she was here, living in the same town with him, dating him every few nights, and having great sex with him. She was even okay with being his Submissive and submitting to some pain, and maybe it did add to her arousal as he said it would. It pleased her to please him, and his comforting afterward was wonderful. Eileen could not imagine how it could be any better, except for the one thing that was missing: he never said he loved her.

<< To Be Continued >>

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Written by BobbieRotica
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