Jake was walking to Eileen’s place to take her out, and thinking about their first Playroom experience during which he gave her some pain with nipple clips. He was happy that she got through it without complaint. She seemed to accept that pleasing him wasn’t so bad, even if it hurt a little, and that it could even be arousing and rewarding. He loved her for her attitude; heck, maybe he just loved her.
Eileen waited at her apartment for Jake to arrive and was also thinking about the discipline he gave her and the nipple clips. It really wasn’t that bad, she decided, and she liked how good she felt for pleasing him. She also realized that a little pain made the sex better, too. While she once had reservations about having any pain, she now knew that she could handle some because it was arousing to please Jake, and he always comforted her afterward.
When Jake arrived, they kissed and headed to the pub for another meal and drinks, then walked to Jake’s apartment. On arriving, they poured another wine and beer to sip as they made out on the sofa. She loved that this was becoming a routine for them and a great warm-up for whatever activities Jake had in mind for them in the Playroom.
“What do you say we go the Playroom, you beautiful woman?” Jake asked.
“Love to, you gorgeous man!” she replied.
Eileen took another sip of her wine before heading to the Playroom. On entering, she quickly undressed, then stood in the middle of the room, naked, and waited for Jake. He entered a minute later, walked over, and kissed her deeply.
“Let’s go to The Step,” he requested.
“Yes, Master, she replied and walked to the low Step near the corner of the room, then stepped unto it.
“Let ‘s have you kneel on it facing me this time,” he told her.
“Yes, Master.”
She knelt facing him, wondering where this was headed since he’d never had her kneel before. Jake stood before her, undid his pants, and dropped them to his knees, then followed with his briefs. His erection popped free and pointed at her face.
“Take me in your mouth and give me a blow job,” he ordered.
Eileen was suddenly unable to move. She had not thought much about ever giving Jake a blow job, but now that he was asking, she froze. He waited a few moments, then spoke.
“You have permission to speak,” he told her. “Tell me why you’re not obeying.”
Eileen was panicking. Despite seeing lots of oral sex on the porn she watched, she had never done it and didn’t think she could.
“I can’t do it,” she said. “It’s too gross.”
“That’s not acceptable. Giving me oral satisfaction is a must for me, and you’ll need to muster the courage to do it. I say again, give me a blow job.”
“I just can’t,” she said quietly.
“Won’t you even try?” he asked.
“No.”
“Then you may get dressed and leave the room. We’re done here,” he said, disappointment in his voice.
“Can’t we do something else?” she asked.
“No. You refused to do what would please me, so we’re done.”
Eileen was surprised at Jake’s rigidness on this, but she did as he asked, got dressed, and left the room. She waited on the sofa for him, and Jake came out of the Playroom a minute later.
“I’m so sorry, Jake, but I just can’t do that,” she said.
“Eileen, a blow job is a basic thing a woman does for her man. I need you to do it for me, but you wouldn’t even try.”
“I’m so sorry. Can you forgive me?”
“I can forgive you, but I can’t keep you as my Sub if you won’t do that for me.”
“What? You don’t want me as your Sub anymore?”
“I want you more than you know, but you must be willing to do that. You can leave now. Go home and think about it, and call me when you’ve found a way to get yourself to give me a blow job.”
“Please, No! I don’t want to lose what we have.”
“I’m sorry, but that’s how it is. Go home, and call me when you’re ready to do as I asked.”
Eileen grabbed her coat and left. On the walk home, she cried and thought about what Jake was doing to them. How could he throw away all they had over this one thing? She’d done everything he’d asked, and suddenly it wasn’t enough?
At home, Eileen poured herself a full glass of wine and sat in her living room, sobbing. She loved Jack, and she thought he loved her, but he was willing to throw it all away unless she gave him a blow job. She drank her wine and poured another. After the second glass, she was tired, so she went to bed and cried herself to sleep.
The next day, Eileen hoped she would get a call from Jake asking her out, or to come over to talk, or something. But Jake did not call. She worried that he was going to be stubborn about this, and she would be the one who had to cave. She didn’t want to cave, but she didn’t want to lose him either, and there were plenty of girls at the college who could steal him away if she waited too long.
Still, how could she give him a blow job? It was just too gross to think about letting him put his penis in her mouth, the same penis he would have peed with many times since his last shower. And when he came, he’d ejaculate semen into her mouth. No, she couldn’t do it. She cried herself to sleep again that night.
Another day passed, and still no word from Jake. How could he do this to her after all she did for him? It wasn’t fair. She decided to learn more about oral sex, so she looked up fellatio on the internet. She learned that it was safe and that a healthy body would fight off any germs involved except AIDS, which she knew Jake didn’t have. Then she watched some porn and studied what the girls did for the guys. It still looked gross to her, but maybe it was doable. She went to bed, lay awake worrying, and just before falling asleep, she finally decided to call him the next day.
+ + +
“Hi Jake, it’s Eileen. Can we get together this evening? I love you, and I’ve decided I’m willing to go along with the blow job, and whatever you want to do,” she told him on the phone the next morning.
“Great! How about we eat at the pub at seven? Can I meet you there?” he asked.
“Sure. I’ll see you at seven.”
And that was it, Eileen thought, all taken care of. She’d just please him in whatever he wanted. After all, he’d been right so far about all of it: being his submissive, being turned on by pleasing him, being aroused by a little pain, everything. She looked forward to the evening and getting back to where they’d left off.
She met Jake at the pub, and they enjoyed a nice meal with wine and beer, just like before.
“I was so glad you called me,” Jake offered. “I was missing you, and I’m glad you decided to do that thing we discussed.” He spoke cryptically since there were others within earshot of their booth.
“I’m sorry it took me so long to decide, but I’m sure now. You’ve been right about everything, so why didn’t I just trust you? Now I will.”
They finished their meal and headed to Jake’s place. On arriving, they sat on the sofa with their usual wine and beer, when Jake pulled Eileen to him and kissed her passionately.
“I’m so glad you changed your mind about the blow job, Eileen. It’s important to me, and having you on board with it can save our relationship.”
“Ya, I just realized you were right about everything else, and I should just trust you. Besides, I really do want to please you in whatever you want me to do.”
This was music to Jake’s ear, and he couldn’t help expressing himself honestly to her.
“That’s why I love you, Eileen.”
She heard that line and hugged and kissed him like never before! She’d waited so long, and Jake finally said he loved her.
In her excitement, she blurted out, “Let’s go to the Playroom!”
“Okay, ” he replied.
She was so happy at his words that it took a moment to remember that she was to go in first, so she set her wine down on the coffee table and headed to the Playroom. Once there, she took her clothes off and stood in the middle, naked, just as Jake had asked her to do.
He came in a minute later, looking at her with a nice smile, happy.
“Please go to the Step,” he said.
“Yes Master,” she replied. She went to the Step and stood on it as instructed. Jake came over and stood in front of her.
“Kneel on the Step, please,” he ordered, as he dropped his jeans and briefs to the floor, releasing his erect penis.
“Yes Master,” Eileen said and got on her knees on the Step.
“Now take my penis into your mouth and give me a blow job.”
Eileen did not hesitate, placing her hands on his erection, and guiding him to her mouth. She placed her lips around the head of his dick, licking it all around with her tongue before taking more of him into her. She had learned from her research to swirl her tongue over his penis, feel all its small imperfections, and lick over the tip. Eileen began to move her head back to let some of his dick out, then moved forward to take a little more of it into her mouth each time. She repeated this movement, sucking on his member as she did, and Jake was appreciating her good effort. Then she reached below and caressed his balls, which was a turning point for Jake, who jerked a bit in reaction. By the time she had taken his entire erection inside her, she was getting into a rhythm and picking up speed.
Jake was enjoying what she was doing to him and was happy that she was trying so hard. And she was doing very well, he thought, especially for her first time!
Soon, the friction Eileen was giving his penis was enough to make Jack ready to cum. He held her head as he began to jerk, squirting his semen into her mouth. She tasted its saltiness for the first time, and managed to avoid choking on the further spurts that were coming rapidly. Before long, Jack was done and relaxed a bit before pulling his penis from her mouth. Eileen swallowed the slithery ejaculate in her mouth, then slowly licked his dick up and down, trying to clean all the liquid from him, and ended by licking it from her teeth.
“That was fantastic, my Sub!” he exclaimed.
“Yes, Master,” she said excitedly, with the knowledge that she had pleased Jake. It was the biggest turn-on of all, to have pleased him and have him tell her that she did. She realized she was already very wet.
“Go to the bathroom and rinse your mouth, then return,” he requested.
“Yes, Master,” she replied with profound satisfaction, and she left for the bathroom.
When she returned, Jake spoke.
“Please stand on the Step for me,” he requested.
Eileen walked back to the Step and stood on it, her hands ready for the lashes.
Jake put the lashes on her wrists, hoisted her hands over her head, and attached them to the ceiling hook. She knew he’d ask, so she had already spread her legs apart, and he lashed them to the ends of the Step.
Then Jake got the blindfold and put it on her. Not seeing what was going to happen added a sense of foreboding for Eileen, but also excitement, and thinking about the possibilities made her wetter.
Jake went to the small table and picked up a feather tickler before returning to Eileen. He touched its soft feathers to her neck and swirled it as he walked around her. She reacted to the pleasing feel with a smile, not knowing exactly what it was. Jake moved around to her back, keeping the feathers on her skin but moving the tickler down her back, which caused Eileen to squirm a bit, then down the outside of her leg, then up the inside of her leg to her rear, across and down the other leg, and back up. He teased her rear with it briefly before walking it around to her front.
There, he dragged the feathers to her breasts, swirling around them and giving Eileen tingly jolts of ticklish pleasure. When he started to flick the feathers back and forth over her nipples, she loved the feel of it and her nipples hardened quickly while she got wetter yet. The ticklish feel was nice but also left a sometimes agonizing urge to rub the tickle away anywhere that it had been, which was getting to Eileen and she was squirming more intensely now. Jake sensed her urgent need, took the feathers away, and quickly rubbed all over her legs, arms, back, and breasts, extinguishing the tickle she felt.
“I’m going to do something different now, and if it hurts too much, you have permission to tell me,” he told her.
“Yes, Master,” she dutifully replied, wondering what he was going to do, and unable to see what he would be using to do it.
He left her calmer and no longer squirming from the tickle she felt, went back to the small table, and replaced the feather tickler with a flogger with a handle and long, thin leather strands. Walking back to Eileen, he stroked her gently on her rear, followed by a few stronger strokes. Eileen felt it slap her cheeks, but it was soft and quite nice. Jake slowly increased the intensity of his strikes until it stung a little, but she was okay with it.
After flogging her rear lightly, almost playfully, for a few minutes, Jake dragged the strands up and over her shoulder and let them come to rest on her breast. Then he started to give light slaps to her breasts, and Eileen clearly felt it. It was almost pleasant, she thought, this slapping device he was using on her, and it was more than a little arousing. As Jake switched the flogger back and forth over her breasts, her soft mounds were being gently spanked, but her erect nipples were being tormented. Eileen knew this was to please Jake, and she vowed to put up with all she could to accomplish that, so she said nothing and tried to enjoy the arousal. She was succeeding when Jake suddenly stopped.
He let the strands trace down her abdomen to her crotch, which was wide open with her legs lashed to the Step. Jake began to swat her inner thighs, switching the flogger back and forth between them. This was also gentle, and Eileen didn’t mind it, but wondered where this was going. Soon, Jake increased the intensity of the strikes on her inner thighs, and it began to hurt more with a stinging feel. But she was able to tolerate it, and her arousal continued as she knew she was pleasing him.
After a minute or two of switching her inner thighs and causing her some notable stinging pain, Jake lightened up. He kept the flogger lightly striking her, but altered his path to include her pussy.
This was new, and Eileen felt the flogger sting her pussy lips as Jake hit them lightly with the strands. He continued to swat her inner thighs with strikes that hurt, adding lighter strikes against her pussy with each cycle. The leather strands were soon penetrating her tender folds and reaching her clit, and she jerked and squirmed with each soft strike. There was pain, but also arousal at her clitoris, and she began to feel her juices flow. Jake noticed as well, and slowed, then stopped, the flogging. He returned the flogger to the small table.
Upon his return, he ran his hands over the areas he had flogged, soothing Eileen’s skin. He arrived at her pussy last and caressed her. She visibly relaxed at his touch, knowing he was about to do something nice down there as part of his comforting.
She found out she was right when he started to run his fingers up and down her slit, with a nice gentle feel on her pussy and clit. She was very wet now, with the pain and arousal of the tickler and flogger gone, replaced by his soft touch on her snatch. Jake slipped a finger into her and began an in-and-out cycle before adding a second finger. He finger-fucked her, with her squirms now ones of pleasure. Moments later, Jake added his thumb to the action, rubbing it over her clit with each in and out motion, and she began to lose control.
Being blindfolded with no visuals to distract her, it felt like every nerve in her body was residing in her pussy. Eileen jerked and squirmed as much as the lashes would allow, and in no time, she could not hold back. Her body unleashed a massive orgasm that lasted minutes and made her scream in pleasure. When her spasms ended, and she collapsed from exhaustion, held up only by the lashes and strap suspending her from the ceiling, Jake stopped and held her in his arms. He kissed her deeply while she recovered from her orgasm, and when she was able to stand, he undid the lashes at her ankles and wrists.
Jake hugged Eileen and kissed her again.
“You were wonderful, my Sub. We’re done here now, so let’s go to the living room,” he told her.
Eileen was so happy she cried a little, though she tried to hide any tears from Jake.
Back in the living room, they finished the drinks they had left there.
“I enjoyed you being my Sub so much tonight, Eileen. You were just great! And now that you’ve overcome your blow job reluctance, I wanted to ask if you’d like to move in with me?”
“Oh, Jake, do you mean it?”
“Yes, of course.”
“I’d love to! When can I move in?”
“As soon as you can, Eileen. I want you here with me every night!”
Eileen moved to him on the sofa and kissed him passionately.
“I love you!” she exclaimed with obvious happiness.
“I love you, too, Eileen,” he responded as he kissed her.
They made out for a while more before leaving Jake’s place to walk back to hers, talking about when she might move in. When they arrived at Eileen’s apartment, Jake kissed her goodnight and left.
Back inside, Eileen broke down in tears of happiness. Her dreams were about to come true. She was going to live with the man she loved and was obsessed with every day for the last four years.
+ + +
In the months after Eileen moved in with Jake, they settled into a nice routine, with him attending classes and her working at the UPS Store. They ate at home most nights, but went to the pub or another restaurant twice a week, and took in a movie, play, or concert at least twice a month.
Their sex life also settled in nicely. They continued their Master and Sub relationship, going to the Playroom almost every evening. Jake changed the rules a bit, allowing her to speak anytime they were doing impact play with things like paddles or floggers, even feathers, to tell him if it was too intense. Knowing he would stop or adjust made her comfortable and able to accept a little more pain over time, which she did willingly since she knew it pleased him, and he always comforted her afterward. It got to be that the idea of submitting to pain became a turn-on for her, and she grew to look forward to it, partly for the way it pleased the man she’d always loved, partly for his comforting her after, and partly because it made the sex more intense and enjoyable for her.
Jake and Eileen lived together until he graduated from college, and then they got married. He found a good job in a city in the same state, they moved there, made friends, and continued their lifestyle, including the use of a new Playroom.
Eileen’s obsession could have gone bad in so many ways, but she never gave up on it, and she and Jake had their fairytale ending!
<< The End >>
