Learning to Let Go

Jonah could not remember a time when he was more nervous.

Per his habit, he showed up far too early at the Cheesecake Factory, and was waiting at a table.

For her.

For the woman he had been chatting with online and exposing some of his deepest, most embarrassing fantasies to.

The woman who wanted to meet him in person.

The Domme who he wanted so badly.

While he was lost in his thoughts, he heard her voice.

"You must be Jonah."

He looked up and saw Vivian. She was so beautiful. She was curvy and fit, but not a stick figure. Her curly brown hair looked so soft. Her eyes were so dark and sultry. He blinked a few times before realizing he hadn't responded.

"Oh! Uh, yeah, I'm Jonah. It's nice to meet you, Vivian."

Vivian laughed. This boy was adorable. Willowy and thin without looking weak, with a cute boyish face a wispy beard couldn't hide. She was a little anxious for this date, wondering if he lied during their chats or sent in fake pictures, but the Jonah before her looked more or less like the Jonah she had imagined.

The two of them had been chatting on a BDSM forum for almost a month at that point. They had normal chemistry (liking the same music, senses of humor that complemented each other, both Christian), but they really bonded in their fantasies.

Vivian was dominant and Jonah was submissive.

When they found out that they both lived in Los Angeles, Vivian decided that they needed to meet up. Jonah agreed with her.

She sat down and smiled at him. He was 23 and she was 31, so they didn't look like an average couple, but they didn't want to be an average couple.

Jonah drummed his fingers against the table.

"I don't really know what to do, to be honest."

Vivian laughed again.

"Right now let's just have a date. We can get into the nitty-gritty later."

He nodded, eager to please.

They had dinner and the conversation flowed nicely between them. They ate and chatted and laughed, enjoying the other's company. When the check came, Vivian grabbed it.

"Shouldn't we split?" Jonah asked.

"Absolutely not. What kind of Domme would I be if I couldn't take care of my sub?"

He swallowed. It was starting.

While they were waiting Vivian grabbed both of Jonah's hands.

"If you want to start, I could take you to my place. It's up to you if we're moving forward with this."

Jonah nodded again, feeling blood rush to his cheeks.

Vivian had been into domination and control for years, but Jonah was relatively green. He had only been in one serious relationship before, and it was entirely conventional. He hadn't yet experienced being controlled. She wanted to take care of this boy, show him that BDSM doesn't have to be scary and is nothing to be ashamed of.

They got the check back and Vivian started to get up.

"You took the metro here, right?"

"Yes, Vivian."

"Good. You're walking home with me tonight."

Jonah followed her out the door.

The walk back to her house was relatively quiet. Vivian didn't say anything and Jonah felt like it wasn't his place to talk. They got to her apartment in about five minutes.

Vivian spoke the moment the door closed.

"I want you to never wear clothes in my house unless I say so, got it?"

"Yes...ma'am." He answered hesitantly.

She smirked. "That's Mistress to you, boy."

"I'm sorry, Mistress." He took off his clothing. She noticed that he paused for a moment before removing his underwear.

He had a small penis. She already knew that and already told him that was irrelevant, even preferable, but it was something no man wants to show off.

Jonah finally lowered his briefs and his member was uncovered. It was about 4 inches when flaccid, bigger than normal, but he was a shower and not a grower. He was so ashamed to think of the women in the past that got excited when they saw him soft and were disappointed when he hardened.

Vivian walked up and inspected his equipment.

"That's not very big at all, is it, huh?"

He nodded meekly.

"Well, you're not supposed to be a big dick for me. You're my sub. This is a sub's cock."

He felt his penis stiffen up slightly.

She ran her hands all over his body. He was 5'9", only 2 inches taller than she was. She had shoes that would make her tower over him, no problem. His body wasn't very hairy and rather pale. As a woman of Israeli descent, she took pleasure in being darker-skinned than her submissive.

"You're a cute boy, Jonah," she said finally. "I'm going to have fun playing with you."

He was so excited to hear her say that.

"Thank you, Mistress."

"Your safe word is 'stingray.' You can say it at any time."

She smiled confidently and grabbed his hand, leading him to her room.

"Get on the bed," she commanded, stripping down to her bra and underwear.

"Yes, Mistress."

They kissed for the first time, though it would be more accurate to say that she ravaged his mouth.

Vivian groped and stroked and kissed all over Jonah. She even bit him in a few choice places. He moaned and sighed like a bitch in heat.

Jonah had never been so aroused in his life. He felt like every cell, every nerve in his body was under her control. He was rock hard and leaking without her even coming close to touching his dick. It was like he was flying.

The Domme sucked harder and harder on her sub's neck until he was squealing. She knew a mark would form. She wanted this boy branded as hers.

"You're going to eat my pussy now," she stated.

He nodded. He waited a second for her to take off her boy shorts, but when she didn't he realized what she wanted and removed them herself.

Her sex was warm, wet, and inviting. He dove in like it was the most natural thing in the world.

Vivian grabbed his head to stop him.

"Slow down, boy. It's not a race. Do what I say."

"I'm sorry, Mistress."

"Don't apologize, just listen to me."

She told him how she wanted him to do it, how to be gentle and deliberate instead of just slobbering all over like a dog.

"Guys complain about girls giving half-assed head, but they're just as guilty of going through the motions. This isn't to loosen me up, this is to give me pleasure, so act like it."

Jonah obediently clung on to her every word, wanting to be the best pussyeater he could be for her. They both noticed that even though there was no stimulation to him anymore, his erection had not subsided in the least.

For almost thirty minutes he followed her instructions. Eventually she came hard, and he sat back waiting for her to calm down. Eventually, Vivian sat up.

"Look at me."

He obeyed, terrified that he had done something wrong.

"You're a good boy, Jonah. That was wonderful."

So much satisfaction flooded him at that moment he was scared he was going to cry. He had wanted to hear those words so badly. He was a good boy. He was her good boy.

"You're getting a little reward, sub. Get over here."

He crawled to her and she flipped him over aggressively, diving down and easily taking his whole penis into her mouth. He yelped like a frightened animal.

Jonah was horrified that he was going to blow his load in less than a minute, but he couldn't do anything to stop his orgasm from approaching. He climbed and climbed until he was at the very brink...

And then she stopped. She just sat back, leaving him on the razor's edge. He had no idea what was going on.

"What's that look for?" Vivian asked.

"I...um..."

"Spit it out."

"I really want to come, Mistress."

She smirked again.

"Nope. You're not having an orgasm tonight."

She said that so casually that Jonah knew he had to have fucked up somewhere. He did something to piss her off and now he was getting punished! In spite of himself he felt his lower lip quiver.

"M-Mistress, what did I d-do wrong? A-Are you mad at me?"

Without a word she grabbed him and pulled him into a tight hug.

"Not at all, baby. You seem to be under the impression that I'm denying you to punish you. This is just to show you who's in charge. If I was mad at you, I wouldn't have sucked your cock like that. You'll be able to orgasm, and it's going to rock your world, just not tonight, okay?"

He nodded. She stroked his hair like he was a child. He spoke a few minutes later.

"I...I'm sorry for freaking out like that, Mistress," he whimpered. "I'm new to this."

"It's alright, boy. You're still a pup in training, so it's my job to be patient with you."

She kissed him so tenderly, so affectionately.

The two of them relaxed together for quite a while, Vivian in her underwear and Jonah still wearing nothing at all. Eventually she sat them both up.

"So, Jonah," Vivian said. "How was your first sub experience?"

He could tell by the change in her tone that the scene was over, so he replied like he normally would.

"It was awesome. I never felt like that before. Did you like it?"

"Absolutely. You're a born submissive. I'm happy we found each other."

She saw something else in his expression.

"What's on your mind?"

He looked down like he was embarrassed.

"It's just kind of weird to think about how I didn't get off. That's never been an issue for me. It's never been hard and I've always been able to do it. But now that's gone and it just feels...odd."

She nodded understandingly.

"It's always strange at first, but denial is a part of submission, and it makes the orgasms spectacular when they finally happen. Besides, it's not like I handcuffed you or anything," she gestured at him. "If you really wanted to get off you would have used the safe word or just reached down and did it yourself, but you didn't. That tells me that you genuinely want this."

He raised his eyebrows in shock. That was completely true and he never noticed. Disobeying her hadn't even occurred to him as a possibility. That was likely part of having submissive tendencies.

The two of them chatted some more before Vivian decided that they should be going to sleep. Jonah looked at the bed confusedly.

"There's only one pillow."

She laughed. "That's not true at all. You've got two pillows right here." She pointed at her chest and his eyes widened.

"Really?"

"Of course. Good boys should sleep in comfort."

It definitely took a little maneuvering and adjusting, but the two of them finally settled into a position they were both comfortable with, Vivian on her back and Jonah cuddled against her, face and head resting against her breasts. She was laying her arms on his naked body. It made him feel small, like she was protecting him. It felt so good.

Vivian reached down and cupped his buttocks.

"You have a soft ass for a skinny boy," she said.

"I'm glad you like it."

"We're going to have fun with it one of these days. You know that, right?"

"Yes," he sighed dreamily.

"Now get some sleep, Jonah. You've had a big day."

He snuggled a little closer. "Yes, Mistress."

*****

Jonah was so disoriented when he woke up. It's like right after he said goodnight, he blinked and it was immediately morning. He hadn't collapsed into such a deep, dreamless sleep since he was a little kid.

He didn't want to move yet. He felt so comfortable snuggled in between Vivian's tits. They were on the bigger side, likely a C or a D cup, and felt so soft and inviting. It occurred to him that he hadn't even seen them uncovered. He didn't mind. She was in charge; he would see them when she thought he should.

Jonah realized Vivian was awake when she began stroking his back with her hand. He moved his head so he could look at her.

"Good morning, baby boy," she said.

He grinned. "Good morning, Vivian."

They kissed and he rolled off so they could look at each other.

"Did you sleep well?" she asked.

Jonah laughed. "That was the best sleep I've ever had."

Vivian reached out and cupped his cheek. "We should talk about what we want to do next."

He nodded. In their online discussion, he had told her that he wanted a woman who would do more than dominate him in the bedroom. He wanted someone who would tell him what to spend his money on, what his schedule should be, and generally make important decisions in his life. Jonah didn't want to be locked up in a cage or made into a slave, but he wanted to feel like he belonged to somebody, as a possession as well as a partner.

Vivian knew all this, but also knew he needed to be eased into it. She had to start slow or he would get overwhelmed and maybe even try to bail out. She stroked his face and decided where they would start.

"Do you like having a beard, Jonah?"

"Not really. I just have one hide the babyface."

She patted his cheek. "I think a little babyface would do you some good. I want you to shave it and keep your face smooth."

He nodded. "Yes, Mistress."

Vivian yawned. It was Saturday, so neither of them had anywhere to be, but she decided that they'd had enough fun for the time being.

Jonah dressed and got ready to leave. Vivian stopped him right as he was heading to the door.

"We're going to meet up again next Friday. You have my permission to come before then, but it can only happen once."

He nodded submissively.

"I'm using on the honor system, boy. It's up to you and you alone to follow my order. Can I count on you?"

Jonah looked into his Domme's beautiful eyes.

"You can count on me, Vivian."

She hugged him and told him he was a good boy. He was grinning ear to ear when he left.

*****

The next week was difficult for Jonah. He wanted to wait until halfway through the week to have his one orgasm, but couldn't help himself and masturbated on Sunday. He was horny and wanted to jerk off for the entire week, but every time he was tempted he thought about Vivian saying she was counting on him. He couldn't let her down.

The two of them texted throughout the week and she encouraged him, saying that she knew he was keeping his promise and that it made her so happy to have a sub that obeyed her. It was that encouragement that kept him true to his word.

The next Friday they went to see a movie. Vivian made it a point to tell Jonah that he looked adorable clean-shaven, and wanted him to keep it up. He assured her that he would shave every day if that's what she wanted. After the movie they went to her apartment again. He stripped down completely and she once again kept on a bra and underwear. He really wanted to see her naked, but didn't want to demand it from her.

That night Vivian played with Jonah's body while he was blindfolded, and losing his sight buried the needle on all his other senses. His body tingled when she touched him. He could hear the beating of both their hearts. He even thought he could smell his own arousal and precum.

There was a point where Vivian sat directly on his face and he began eating her out the instant he realized she had taken off her panties. He remembered all the tips she had given him. His finesse and attention to detail did not go unnoticed by Vivian. She was so turned on by his ardent need to please that she came in half the time it took in their previous session. She wanted to give him a reward for being so good.

She got up to get some Astroglide but decided to wait, let him squirm for a bit. She stood there, and watched him go from expectant to confused. When she sensed he was starting to get bored she got really close and began breathing in his ear.

Jonah's arousal shot through the roof. He was wound up so tightly that he thought he would squirt with the slightest touch. For an agonizing few minutes, she touched around his cock, cupping his balls or stroking his pubic hair. Then, after what felt like hours, she grabbed his cock and jerked him off.

It took about five seconds for him to have an intense orgasm, and she didn't even slow down. For the first time in his life, he felt a second orgasm come on. It was painful, but a deliciously erotic and submissive feeling.

Vivian was delighted to see her sub shoot again. She scooped up both of his loads and fed it to him, with his blindfold still on. She cuddled him a bit longer before she allowed him to remove it.

That night she spooned Jonah, who was curled up into almost a fetal position. They slept happily together.

It was the next day that Vivian made the decision to take the next step.

"I'm going to peg you next time, boy. You need to prepare."

Jonah raised his eyebrows.

"How? Shouldn't I just give myself an enema that night?"

"Enemas aren't something you should rely on. They flush out your colon, washing away even the good bacteria that keep it healthy. The only healthy way to truly be ready to get fucked in the ass at any time is with fiber."

She left the room and returned with a bottle from the pill cabinet in her kitchen. Vivian tossed it to him and he fumbled to catch it.

"These are fiber supplements designed to clean a person out for anal sex. I take them and they've changed my life. Take 3 in the morning and 3 in the evening all week, making sure to also drink plenty of water. You'll be clean as a whistle in no time."

He poured out a few and saw they were gigantic horse capsules filled with beige powder.

"How do I reimburse you for this?" Jonah asked.

She smirked.

"That first bottle is a gift. You'll be hooked and want to buy them yourself by the time you finish."

He nodded. It was something else he would add to his daily routine because of Vivian. He was excited to have her take control of a new part of his life.

Jonah discovered that Vivian wasn't exaggerating about the fiber supplements. The first few days he had huge bowel movements, then his body became regular. At close to the same time every day he took a shit and found he needed to wipe less and less. By Thursday, he felt clean enough to probe around his back door. It was strange, but also arousing. It felt naughty, taboo. He liked that feeling.

But he stopped himself before he could do anything more. It wasn't his choice what to do with his hole. His body belonged to Vivian now.

*****

There was no preface of a date that Friday. He would simply go to her apartment at a certain time so they could begin taking the next step in their D/s relationship.

Jonah was as ready as he would ever be. He used baby wipes to clean himself up the best he could and hadn't come in days. He wanted to give this his all.

Once Vivian let him in he stripped down, now out of habit. She was dressed in lingerie that made her look sexy and very powerful.

"You look incredible, Mistress."

"Thank you, submissive. Tonight is something worth dressing up for."

He followed her to her bedroom, and after some quick kissing, she told him to get on the bed. He was to lay on his stomach and spread his legs. She put a pillow under his hips and pointed his little penis down to his feet. She stood back and looked at Jonah, put in such a slutty, submissive pose. It suited him well.

"How clean are you, boy?"

"I didn't know that my anus could even feel this clean, Mistress. Those fiber supplements are amazing. Thank you for telling me to take them."

"You're welcome. Turn your head so I can show you something."

Jonah complied and gasped at what he saw.

Vivian had put on the strap-on dildo, the first of many she planned to eventually use on her sub. It was six inches long and five inches in circumference. It was jet black and shiny, nothing like a penis. It looked imposing. Unforgiving.

"This is what I plan to fuck you with, Jonah. It's bigger than you. Much bigger, in fact. I'm going to use it to fuck you harder than you could ever hope to fuck me. How does that make you feel, boy?"

The submissive swallowed, his throat suddenly feeling very dry.

"It...it's kind of scary, but...it's exciting at the same time..."

Vivian ran her fingers through his hair.

"That's understandable. There's something about pegging that really gets sub boys like you going. I think it's the idea of it being pure domination. I don't get much stimulation from a strap-on like this, so it's all about my submissive. It's all to show him who's in control."