Learning to Let Go

Jonah bit his lower lip in a way that turned Vivian on more than he could know.

"What's your safe word?"

"It's 'stingray,' Mistress. I'll use it if I want you to stop."

She placed his head back to forward position.

"Let me open you up, sub. I need to get you ready for what's coming."

Jonah nodded and he felt her lightly touch his hole with a lube-covered finger. He gasped. The sensation was so much more powerful than when he touched himself there! But then she put a finger in and it really hurt. He knew he had to relax, but it was hard to calm down.

As he promised, his passage was clean, and Vivian didn't need gloves. She could feel how tight he was, how his hole was fighting against the invasion.

"You need to relax."

"I'm trying, Mistress!"

"You need to try harder, boy, and do you know why?"

"Because it will be more pleasurable for me if I do."

Vivian slapped her sub's ass hard enough to make him yelp.

"That's the wrong answer. You need to relax because I'm not going to hold back. I'm not going easy on you because it's your first time. No matter how tight you are, no matter how much pain you're in, I'm fucking you into the mattress. This strap-on has no give. It doesn't care how much you try to fight it. You need to relax because if you don't, you're going to be in a world of hurt."

She could see a small gush of pre-come get released from his tiny cock. He liked hearing her say that.

Vivian eventually did feel Jonah loosen up somewhat and knew it was time to begin. She put lube all over the dildo and told Jonah the same thing she told every guy she was about to fuck for the first time.

"I'm about to fuck you, boy, and it's going to hurt. A lot. But it's up to you how much pain you're going to be in. If you try to be all macho about it, reject the sensation of a woman fucking you, you're going to lose. You'll wear yourself out and feel the pain of this for days. But that's not how this has to go."

She reached out a hand and petted his hair again.

"If you submit, accept that you're made to be fucked and dominated, the pain will go away and be replaced by pleasure. Tonight you'll either let your masculinity slip away or I'm going to remove it by force. It's your choice."

Vivian put the head of her strap-on against Jonah's virgin hole.

"What's your safe word?" she asked again.

"It's 'stingray.'"

Without another word she began pushing.

White-hot pain exploded in Jonah's body. He was being split in half. The dildo was so hot, so hard! He tried to breathe as he felt his hole get stretched out.

Vivian could tell that her poor boy was struggling. She got down and kissed his ear.

"It's okay, baby. I'm right here. Relax."

The submissive did his best to do what his Domme had asked. Bit by bit, the pain decreased. Once the head of the dildo popped in it hurt less.

"I'm inside you, boy. You're my bitch now."

Jonah mewled and nodded his head.

As Vivian started rocking back and forth, truly beginning to fuck him, Jonah felt tears come to his eyes. It was partially from the pain, it still hurt like hell, but that wasn't all of it.

Every fiber or his being felt her control. He had given his body to Vivian and she was taking it. He was being used, and not even being used for pleasure. His Domme was doing it simply because she liked having control over him. He was being used like an object.

And he liked that.

It was the strangest thing, slipping into a submissive headspace. He felt the pain ebb away more and more as he kept giving in. It was even starting to feel good. His flaccid penis was starting to stiffen up again.

Vivian could feel the boy submit more and more. He was relaxing, accepting what his role was. It was slow, but steady progress.

It was after about five minutes that he had a thought.

I wonder, what would happen if I just gave up completely?

He wasn't sure he could even do that, but maybe all the pain would go away and it would feel great. He knew it's what Vivian would want him to do. He wanted to at least try.

Jonah took a deep breath in and out before thinking clearly.

I'm not a man right now. I'm hardly a person right now. I'm hole that likes getting fucked. I'm an object.

And I'm okay with that.

Vivian noticed an immediate change in Jonah's body. It was like a switch had been flipped. Suddenly there was little to no resistance. He seemed to almost sink into the bed. His body went limp. She was scared that he had fainted, but when she grabbed his head and looked at him, his eyes were open and blinking.

The submissive vaguely wondered why his Domme was looking at him like that. Then he realized that he wasn't supposed to think about this stuff. When she let go of his hair his head fell back down. He was so limp now. It felt good.

Vivian knew that he had given in. He had relaxed, fully accepted what was happening to him. She had never been with a sub that could do it so early on. She knew she had to show him how much she appreciated it.

Wow. She was really fucking him now. He was just letting it happen, too. It was a nice sensation. The minutes ticked by as Jonah slowly forgot about the world around him and just focused on how good it felt to be used. He noticed that something deep inside of him was being brushed. It felt kind of strange. The sensation got stronger and stronger. It almost felt like he was about to piss. The feeling intensified until he started to sense relief.

Oh, that felt so good. So much had built up and it was getting released slowly. He felt happy.

It drained out of him until he was empty and laying there dreamily. It's always nice to take a good piss.

He had just taken a piss.

Jonah just...

Suddenly reality crashed into him.

I just pissed all over Vivian's bed!!

"Oh my gosh, I'm so sorry!"

That sudden outburst scared the hell out of Vivian. Once second he was fully submissive and the next he was right back to the world of the living.

"What the fuck?!"

He got up on all fours.

"Holy crap, I can't believe I just did that! I've never wet the bed before, I promise!"

Vivian was confused for a second. Then it clicked and she started laughing.

"Jonah, you didn't pee, you came!"

The sub's eyes widened, but he looked down at the bed and saw that she was right. There was a load bigger than any he had ever produced on the sheets.

"I...I did that?"

"Yes, you did. You relaxed and nature ran its course. You took that pegging really well."

He blinked a few times, absorbing what his Domme had said.

"Lick up your mess," she commanded.

Jonah nodded and got to work. As he did, Vivian sat back.

Watching her sub come that hard from being fucked turned her on so much that she removed the strap-on and got herself off. She had been laying in the afterglow for about a minute when he startled her by freaking out.

She wrapped her arms around him when he finished.

"You've been a very good boy for me. It's time for your reward."

For the first time, she shed her clothes and showed Jonah her naked body.

Vivian was so sexy! Her curves, her skin, it was perfect! Jonah was ecstatic.

"May I...may I please touch you, Mistress?"

"Touch me all you want. Just don't put your little cock anywhere it doesn't belong."

Jonah explored her body with his hands and mouth. After a bit, he settled down and just lightly nursed on one of her nipples as she held him.

"Was I good, Vivian?"

She petted his hair.

"You were wonderful. How did it feel?"

He thought about it.

"Once I stopped fighting it, something...changed. It wasn't like I was gone, it's more like I was just sitting outside my body, watching what was happening. It..."

Without any warning he felt tears well up.

"It's kind of scary."

Vivian kissed her boy's cheek.

"That's what submission feels like, baby. And tonight proved that you don't just like doing it, you're good at it."

He nodded, still crying in spite of himself.

"I'm sorry for being such a mess, Vivian."

"Don't worry about it, Jonah. Seeing somebody fall apart because of me, using another person's compliant body, that's what sets me off."

Things were quiet for a while before Jonah spoke again.

"Does this...change things between us? I love being your sub, but I also want to be your boyfriend."

"Outside the bedroom, nothing changed at all. BDSM is all about living out fantasy, but it's not real unless you make it real. You're my sub, but you can still be my boyfriend, too. Even if I decide what you wear, when you come, things like that, you're still your own person. You're doing it because you want to."

Jonah nodded. "That makes sense."

A little bit later something occurred to him.

"Can I feel how stretched out I am?"

Vivian giggled. "Knock yourself out."

He touched his hole with his finger and was shocked by what he felt. It was so soft, so loose! It didn't feel like an anus anymore. It felt like a pussy.

He told her this and she laughed again. "That's the whole idea, Jonah. You're a pussyboy now, and your cunt is all mine."

That night they slept with Jonah laying on top of Vivian again, except now with her breasts uncovered. He felt closer to her in more ways than one.

"Thank you for fucking me, Vivian. I really mean it."

Vivian wrapped her arms around her baby boy.

"The pleasure's all mine."

*****

The weeks passed as Vivian and Jonah continued their relationship, as boyfriend and girlfriend as well as Dominant/submissive.

They began meeting up more frequently than once a week, to date or hang out or have sex. Jonah would always go over to Vivian's place, never the other way around. He explained that he had 2 roommates, neither of which he was friends with, nor felt comfortable having violent sex in the same apartment as. Vivian didn't push the issue.

On the subject of friends, he was a freshman in grad school and had a few friends there. They knew that he had a new girlfriend named Vivian, but they hadn't met her and certainly didn't know that he was her sub. As wonderful as it was exploring this side of himself, he was still embarrassed about it. Vivian was understanding, but wanted things to be transparent sooner rather than later.

Neither Jonah nor Vivian had any qualms at all about her telling her best friend Angela about her new sub boy, though. She wasn't a Domme like Vivian, but was sexually active and saw nothing objectionable about their relationship.

In fact, the first time Jonah met Angela was on a night she came over to Vivian's for drinks. Jonah was surprised to hear that they were expecting company.

"May I please put on clothes, Mistress?"

"I don't see any reason why you should. I don't care if she sees you naked and know she won't either."

She told him that he would get them drinks and stay by her side, and if he was a good boy he would reward him afterwards. Because of that, as much as it embarrassed him, he was dutifully standing at Vivian's side, fully nude, when Angela arrived.

"You must be Jonah. I'm starting to see why Viv talks about you so much; you're adorable."

"He's also mine," Vivian cut in teasingly, "look, but don't touch."

The two ladies had an enjoyable evening, drinking wine and catching up. Jonah didn't have much to do; he occasionally refilled their glasses, but spent most of the evening sitting at his Domme's feet. She would occasionally reach down and pet him.

Jonah's erection was full-on all evening. It was the first time he was submitting to Vivian while not in the privacy of a bedroom.

Vivian kept her word and rewarded Jonah for his obedience after Angela left by sucking his cock, which she rarely did. He had grown to love being pegged, but receiving oral sex was still a special kind of wonderful. Jonah realized that they had been together for almost a month at that point and he never had traditional, penis-into-vagina sex with his girlfriend. They never even discussed it. He wasn't going to push things, but hoped that someday he could earn the honor.

Conversely, Vivian fucked Jonah all the time. He had never given much thought to the different types of pegging, but there was more variety than he would have expected. There was the standard strap-on, where the base would just push against her labia, which would provide some pleasure, but a double-ended dildo allowed for her to receive just as much penetration as he did. Whenever she fucked him with one, she was slower, more deliberate. He realized that she was only thinking about getting herself off, and using his boy-pussy as a means to an end. He loved being objectified that way.

There were also the dildos that strapped on her pubic bone, so she got no stimulation at all, just control. That's when she would let loose and fuck him into a whimpering puddle. He loved the feeling of letting go and feeling Vivian make him hers.

They upgraded to bigger dildos, too. Some were longer, some thicker, and some both. It was during the session with his first 8-incher that he said three words he immediately wanted to shove back in his mouth.

"It hurts, Mommy."

He slapped his hand over his mouth and felt himself turn beet red. He had no idea where that came from.

Vivian was shocked, too. She had heard about Mommy kinks before, but never met somebody that had one. It didn't come off like a poor choice of words, either. It sounded like something he meant.

"Baby, are you okay?"

He almost started crying.

"I'm so sorry, Vivian. That's disgusting."

Vivian pulled out so they could talk properly. She tried to channel her years of experience, sound wiser and more sure of herself than she was.

"It's not disgusting, Jonah. Calling your partner Mommy or Daddy isn't normally bred out of an incest fetish, it's just a need to be taken care of. If you want to call me Mommy sometimes, do it. Otherwise you're hiding something from me, and I don't like that."

He nodded, still looking mortified.

They got back to pegging, and Vivian knew she needed to make him say it again, more for his sake than hers. She fucked him mercilessly, and she knew it was hurting. She got down and wrapped her arms around him.

"Are you okay, my little baby boy?"

He whimpered. "Yes, Mistress."

She pulled out and shoved it all in at once.

"Do you want me to take care of you, baby?"

He didn't say anything. She got down and whispered in his ear.

"Are you going to be a good boy for your Mommy, Jonah?"

He started crying, but answered in the softest voice possible.

"Y-yes, M-M-Mommy..."

She fucked him, now deliberately trying to make him come. He blew a huge load not long after.

From that day on, he would every now and then call her "Mommy" during sex.

Not all the time, but enough for her to know that she nurtured and took care of her boy.

*****

"Jonah, think you and Vivian can go on a double date with me and Dani?"

Jonah's blood turned to ice. He looked at his friend Rick.

"Um...I don't know."

"C'mon, man, Dani said she would be more comfortable in a group on our first date. Help me out."

Jonah knew how much this meant to him. He had been crushing on Dani for months and just recently gathered the courage to ask her out. Rick was counting on him.

He sighed. "I'll ask Vivian."

His friend grinned. "Thanks, dude!"

Jonah went over to Vivian's house that night, and after disrobing he got down on his knees, prostrating himself.

"My loving Mistress, I have a request."

Vivian cocked an eyebrow. This was the first time her sub had done this.

"What is it, boy?"

He looked up at her.

"My friend Rick is about to go on a date with his crush Dani, but they need to be in a group. He asked me to come and bring you so it could be a double date."

She realized what was going on and this wasn't a conversation they should have in their roles.

"Jonah, stand up, we need to talk as equals about this."

Her submissive nodded and got to his feet. He explained how important this was to his friend.

"Did you tell him about...you know...what we do?"

He shook his head. "My friends just know that I have a girlfriend named Vivian. But I'll tell Rick about it if you want me to."

Vivian sighed. "I really don't like how you feel the need to hide this, but I do understand it. Just let him know what you think is appropriate and we can go as a normal couple."

Jonah smiled and hugged his Domme.

"Thank you so much!"

They had sex afterward, and it was almost good enough for Jonah to stop worrying about telling Rick his secret.

Almost.

*****

"So, Jonah. What did you want to talk about?"

He and Rick were sitting in the cafeteria of their grad school, eating lunch together as they often did.

"It's about Vivian."

"Did she say yes?"

"Yeah, but I need to tell you something. It's kind of serious."

Rick tilted his head a little bit. He hadn't seen that look on Jonah's face before. "What's up?"

Jonah took a big breath in and out.

"I haven't introduced you to Vivian yet because I was kind of embarrassed. Not of her, embarrassed of myself. We're..." he paused. "I'm a submissive, and she's my Dominant."

Rick's eyes widened. Jonah kept going.

"We'll act normal in front of you and Dani, but she's a lot older than me. I just wanted to tell you. I feel like I've been lying to everyone."

Rick finished the food that was in his mouth.

"Look, Jonah, what you do in the bedroom is your business. I don't care. As long as you keep things chill during the double date, it doesn't matter."

Jonah nodded, face turning red. Rick changed the subject and the rest of the conversation was relatively normal.

The double date went smoothly, too. The four of them had a good time together and Jonah could see the chemistry form between Rick and Dani. He had a feeling he knew what they were planning when they left together. He and Vivian left to do the same thing.

*****

Jonah would never forget the first time Vivian fisted him.

They had been building up to it for weeks, using bigger and bigger dildos, until she finally thought he was ready. The preparation was normal, but once he was lubed up Vivian pulled out a small brown bottle he'd never seen before.

"What's that, Mistress?"

"These are poppers. You're going to want it if you're taking my fist."

"Is it some kind of special lube?"

"No, boy. It's a muscle relaxant. A few sniffs and this will be a lot easier."

He looked at the bottle, then back at his Domme.

"Do I...do I have to use that, Mistress?"

Vivian was not expecting that.

"Well...not really, but it's going to really help. It'll lessen the pain and keep you relaxed."

Jonah's big eyes locked on hers.

"I...I think I want to try it without them. I kind of like the pain, anyway."

Vivian shrugged and covered her gloved hand with lube.

The first two fingers were easy. Jonah was loose enough at that point that they just slid in. The third finger was met with some resistance, but not too much. The fourth finger really hurt.

"You need to relax, sub."

"I'm doing my best."

He breathed and tried to let go, to enter his submissive headspace, but the pain was distracting. He thought the things that always helped him sink into submission.

I'm an object. I'm her property. My Mistress is using my hole. I'll let her, gladly.

Bit by bit the pain lessened and told her he was ready for the thumb.

Vivian put it in and Jonah started crying. The stretch was agonizing, worse than any he had ever experienced. It kept getting worse. His hole was stretched out so far Jonah was certain it was going to rip. He told himself to count to ten, and if it was still as excruciating by then, he would use the safe word.

One...two...three...four...

The stretch intensified. It felt like somebody was ramming a tree trunk up his ass.