Exploration

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Would obstacles stop her from her dream: humiliating him?
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edrider73
edrider73
1,064 Followers

By Ed RiderMany thanks to whoredinarygirl for first editing and improving this story.

Immense gratitude to BeautifulStorm, the hardest working editor on this site, who not only applies incredible editing expertise but also tremendous effort in following through to make sure the story turns out much better than I ever thought it could be.

"What are you doing?" Lester asked.

"What does it feel like?"

Mandy giggled.

"It feels like you've stuck a finger into me. Why?"

"I just wanted to see what would happen. Carol told me it would arouse you."

"Have you changed your mind? You got really upset when I tried that a couple of times."

"Nope. You're right. The idea of your finger in my ass is still disgusting, and thinking of you touching me anywhere with it after it's been in there makes me want to barf."

"What about your finger inside me? Aren't you afraid it will get dirty and disgusting?"

"Yes. As soon as I pull it out, I'm going to wash it off in the bathroom. How do you feel now?"

"I feel like you're moving it around inside me."

"Does it feel good?"

"I haven't decided."

"Carol was right. A few minutes ago, you were soft and finished for the night. Now look at your cock. Why are you squirming like that?"

"Your finger is really getting me worked up, and it makes me want to do this."

"No! No! Don't do that, Lester!"

"You're doing it to me, so I'm doing it to you. You're squirming, too, so you must feel something."

"I feel horrible. Please take your finger out. I'll make you very glad you did. No! Don't move it like that!"

"Okay. I'll pull it out, but you pull your finger out first."

She removed her finger, and then he did. She jumped up and ran to the bathroom. He heard the faucet running. When she came back, she told him to wash his hands and come back to bed immediately. He laughed and followed her orders.

"It's still hard," she said when he joined her.

There were no more words, just sighs, moans, grunts and cries as they went at each other. They coupled wildly, like animals in heat, and after they came, they were too exhausted to move and fell into a deep sleep. The next morning they both agreed that it had been the hottest sex they had ever had.

************

"Are you exploring again?" Lester asked.

"You know you like it. No, wait, stop!"

"I told you, Mandy. You do it to me, I do it to you."

"That's not fair. You like it. I don't."

"I didn't ask you to do it. You're not doing it for me. You're doing it because it excites you. I'm not doing this for you but for me."

"Be careful."

"As careful as you."

"You're already hard," she said. "Your cock doesn't lie. This turns you on."

"Do you want to pull out now and wash our hands?"

"No. I want to leave it in while we're making love. I promise you, you'll love it."

"Okay. But mine stays in, too."

"It won't work that way."

"You'll make it work."

They were lying on their sides facing each other, and each had a finger in the other's ass. With her body and her other hand, she pushed and pulled and twisted until he was between her legs. He let her move him where she wanted him.

He felt her guide him into her. The finger never came out during her manipulations. Even though it was difficult, he kept his inside her, too. They were in an awkward position, still on their sides, but she was able to move her body back and forth, causing his cock to go in out of her.

"This would be a lot better if you'd take your finger out," she said.

He didn't reply.

She began moving her finger in and out. He tried to do the same to her, but in the position they were in, his arm was trapped, and he couldn't move it.

Her body began moving faster against him and the pace of her finger increased to the same tempo. He heard her begin the soft cries she made as she came, and he felt her anal muscles contracting around his finger. That made him lose control and slam his body into her in a wild orgasm of his own.

As he came, he felt something strange, but he was lost in convulsions and didn't realize what it was until he fell back exhausted.

"Hey!" he yelled as he jerked away from her. "What's the idea?"

She was trying to catch her breath and didn't respond. He looked at her, and she had a satisfied smile on her face. He waited for her to respond, but she didn't say anything. She was enjoying her afterglow, but he couldn't because he was irritated.

"That was a dirty trick to pull on me while I was coming. I never said you could stick a second finger in me. You almost spoiled it."

"That's a lie. It made you come even harder. There was plenty of room. It went in easily."

He didn't say anything after that, but two nights later, they were in bed and stroking each other when she yelled out.

"Ow! That hurts! What are you doing? Stop!"

"I'm just catching up. I didn't have a chance to put two fingers into you the other night when you did it to me."

"But your fingers are a lot larger than mine, and I'm a lot smaller back there than you are."

She tried to move away from him.

"You should have thought of that," he said as he kept his fingers inside her and moved his arm with her so the fingers stayed put.

She stopped moving and turned to look at him.

"Okay, you win," she said, "but take them out for a second and let me do something. I promise you, I'll let you put them back in. Please, Lester!"

He slowly pulled his two fingers out, and when he did, she grabbed them and her other hand reached for a plastic bottle on her high stand. She squeezed out some lubricant and rubbed it all over his fingers, then let them go.

"Okay," she said, "go ahead. Slowly please."

As she spoke, she squeezed lube onto her hand. In a second, she had two fingers moving inside of him. He began moving his fingers inside her. Both of them began squirming a few moments later.

"This isn't fair because I'm uncomfortable and you're getting excited," she said.

"Then take your fingers out."

She didn't respond, but began maneuvering their bodies. They were on their sides again, but this time he made sure she didn't get him into a position where his arm was locked.

AS they began moving together, their fingers were going at the same tempo. Both of them had massive orgasms, and as their bodies went crazy, he once more felt something strange. She had pulled the same trick again.

When she came back from the bathroom, he said, "You know what's going to happen next time, don't you? Now I know why you brought the lube to bed. I'll make sure to use it when I surprise you with three fingers like you did me."

She didn't say anything, but she glared at him.

**********

The next couple of days, they didn't talk much. On the third day, Lester told her at breakfast, "This is stupid. I'm not going to be in a bad mood. If you want to be that way, it's up to you."

He made it a point to act happy, but the coolness continued. Usually, either Mandy or Lester initiated sex two or three times a week, but neither made any attempts for the next ten days.

One night they were looking at each other, and they could each tell what the other wanted.

"What I don't understand is that even though you say my fingers disgust you and hurt, you won't stop," he said. "It's like self-destructive behavior. Why are you doing it?"

"I was thinking about that, too. I don't know why, but pushing my fingers into you gets me incredibly hot. I'm all juicy, and my pussy is tingling.

"I feel powerful while I'm doing it. It's like I'm the man and I'm in control. I'm putting my cock into you the way you put yours into me.

"The fact that you aren't happy about it and I'm doing it anyway turns me on even more. It excites me to think of how humiliating it is for you. I imagine that you're feeling demeaned and used. I've never had such amazing orgasms as I had the last couple of times.

"But you're right. The price I'm paying is getting too high. Tonight, I'll let you put three fingers in me, and I promise I won't put four into you, even though I'm dying to, and I know you can take them. I just hope if I go hysterical with your three fingers, you'll have a little compassion. I am so scared right now."

"Okay," he said. "You win. It really bothered me when you used three fingers last time. I'll admit that one or two fingers felt good. But three didn't do anything except make me feel uncomfortable and angry. If you want, I'll forget about getting even and we can let this whole thing go."

"No," she said quickly. "I'm not ready to give up, even though I know three fingers is going to be horrible for me. But I am going to ask you to go along with some things that I thought of."

"What do you mean?"

"Let's start with this," she said. "Look at my three middle fingers. See, I'm putting my middle finger behind the other two fingers and squeezing all three together. It makes them take up less space. Would you do that for me?"

"Sure," he said.

"Thank you," she said, and she leaned over and kissed him. "Please do it now for practice."

When he put his fingers together and then pointed to show her, she reached under her pillow and pulled out a cloth tape measure and wrapped it tightly around his fingers. She looked at the numbers, and then she took it off.

"Okay," she said. "Now I want both of us to prep."

"What do you mean?"

"Before we stick our fingers in, I want us to be clean."

"Are you saying what I think you're saying?"

"Yes, I'll go first," she said. "I've got all the stuff in the bathroom. After I finish and wash myself off, you'll go in and do the same thing. I'm hoping that if I know you're clean inside and I am, too, I won't think that I'm smelling anything and become nauseous."

When he came back to bed fifteen minutes later, he felt empty inside and not aroused at all. As soon as he lay down, he felt something go into his ass.

"You're not wasting any time, are you?"

"That's not my finger," she said. "It's a bulb syringe with a very tiny nozzle, so don't complain. I did it to myself already. I'm squeezing a lot of lube into you. My fingers will glide into you so smoothly that it won't hurt at all."

"Whatever you say."

"You probably don't care that I cut my nails so they don't scratch you."

"Thanks."

She smiled at him and then got between his legs. He drew his breath in sharply as she sucked him in. Maybe because they hadn't had sex in so long, he became hard instantly, despite the slimy feeling inside him.

She continued to stimulate him with her mouth and tongue before she pulled her head up and grabbed his cock with one hand and the cloth tape measure in the other. She wrapped it around him and looked at it, then took it off and tossed it aside.

As he felt her fingers enter him, he followed her lead. Her third finger made him jerk as it entered. Even with all the lube, it didn't feel good. It stretched him and caused discomfort.

As she began moving her fingers, he got more used to them, even though they still felt intrusive. He had to resist the impulse to move his body away to get this foreign object out of him.

When his third finger entered Mandy, she began shaking uncontrollably and shouted out, "Stop! Stop, please!"

He pulled his fingers out.

"That was horrible," she said. "I don't know if I can do this. Wait a minute."

He felt her fingers still working inside him. She hadn't stopped when he had.

She stopped shaking and said, "All right. Try again, but very slowly please. Oh no! Oh no! I'm sorry. Don't stop."

He slowly inserted his three fingers. When they were all in, she took a deep breath and held it in for a while before slowly exhaling. Meanwhile, her fingers were going in and out of him and increasing their tempo. He began doing the same thing.

"What are you doing?" she yelled, and he stopped.

She breathed deeply a few times and said softly, "I'm sorry. Do it. I'll try not to stop you again."

As he increased his tempo slowly until it matched hers, she made horrible little noises. She was crying and shrieking and moaning in agony, but her fingers never stopped inside him. They were plunging in violently now. She seemed out of control, and they began hurting him, but he resisted the urge to do the same to her. He just kept the same pace and tried to move his fingers smoothly, like a machine.

She slowed down and began adjusting their bodies. He was amazed that she was doing this because she was in such obvious pain. Her suffering was a turn-off for him. He wondered if he could get hard enough for insertion.

She must have thought of that, because he felt her inhaling his limp cock and using her mouth and tongue to get him hard again. When she lifted her head, she quickly placed him at the spot she wanted and pulled him to her.

She was under him and partially sideways to him. One arm pulled him and guided him as their bodies began moving together, while the other arm was reaching behind him and working her three fingers inside him. They were tormenting him now, pulling at the opening and stretching it, pushing in as far as they could go and bruising him inside.

He had buried his fingers deep inside her, but she had moved so that she was lying on his arm again, and his hand was trapped, so all he could do was wiggle his fingers. He noticed that when their two bodies slammed together, his fingers were driven deeper into her, and each time that happened, she winced in pain. But she didn't slow down.

He began moaning as his insides were assaulted, and that's when he noticed her body start to lose control. As he felt her shake with her orgasm, he lost control and slammed into her so hard that he was afraid he might send her body through the mattress. When he came, it felt great, but it didn't last long, because the pain caused by her fingers quickly replaced his exultation.

She continued bucking underneath him, and drove herself to another orgasm before she finally fell back and seemed to shrink into a lump of flesh that was engulfed in gasping and sobbing. Her fingers were still in him, and his were trapped in her as his full body weight was pressing on her.

After a few minutes, she began trying to push him off with her free hand.

"I'm not moving until you take your fingers out," he said.

"Sorry. I forgot."

She slowly withdrew her fingers, and then he rolled off her and carefully pulled his out. They lay side by side breathing heavily for almost five minutes, and then she got up and went to the bathroom.

*************

The next morning after each hobbled into the kitchen and sat down painfully at the table, she looked at him mournfully and then burst into laughter. He began laughing, too, more in relief than anything else.

"We are crazy," she said, "I'll admit it -- I'm crazier than you. I should have stopped last night when I couldn't stand the pain anymore, but I was so turned on by what I was doing to you that I had to keep going. The more I could see you breaking down, the wilder I felt. When I came, it was so amazing that I forgot about the pain you were causing me for a while.

"But after that, the pleasure was over, and the pain hasn't stopped yet. So in a way I'm glad we did it, but I also know I'll never let you do that to me again. It's just not worth it."

"So you're finally done with this,"

"I didn't say that. I just said, I won't ever let you put more than one of your thick, long fingers inside my ass again. But I still have this powerful desire to ravage you with four of my slender fingers, and then five and then my whole hand. It won't hurt you nearly as much as you hurt me last night."

"That's not going to happen. My rule stands. A finger for a finger."

"I'm not agreeing to that anymore, but I'm working on another idea. Right now, we're not in shape for anything, but once we're healed, I'll tell you about it. So let's drop this for now."

***********

When they began to have sex again, she didn't bring up her idea, and he decided she had given up on it. At first, they avoided anal play completely, but after a while, she began inserting a finger into him occasionally. Each time, he followed her example, and that's as far as it went.

They did the fingering about once a month, and she attacked him so hard that he was always sore when they finished, but she was, too, because he continued to copy her.

After one of these sessions, when both of them were tired and sore, she said, "Will you listen with an open mind if I tell you my idea?"

"What idea? Oh, is this your idea for sticking your whole hand inside my ass? Go ahead. I'm curious about how you think I'd ever agree to that."

"Okay," she said, "please hear me out and don't interrupt me. Promise me you won't make a quick decision and you'll think about it."

"I promise," he said with a laugh.

"Remember when I measured the width of your three fingers before we started, and then when I got you hard, I measured the width of your cock?"

"I forgot, but now I remember."

"Do you also remember how I freaked out when you asked me once if I would ever consider letting you do my ass. It was a long time ago."

"I'll never forget that," he said. "You were so scared that you were almost hysterical. I thought I'd have to call a nurse to give you a sedative. I knew better than to ever bring that up again."

"Well the other night, I found out that as big you are when you're hard, you're not as big as three of your thick fingers squeezed together. That got me to thinking about what I want and what you want.

"Here's why you'll let me put my hand inside you. If you do, you can have anal sex with me. It would have to be two different nights, because I wouldn't be in any shape to do anything after you destroyed my ass. Yes, I'd let you go first.

"Okay. Give me your first reaction. But remember, you promised that you'd think about it, so I don't want any final answer today."

"You want my reaction. All right. First of all, I've managed to do without anal so far. Yes, I liked it when I did it with a few girls before I met you, even though none of them liked it.

"Usually, that turns me off, but I guess it's just like you and your fingers. Even though you know I don't like it, you don't care. I liked it even though I know they were having a hard time with it.

"After I saw their reactions, I never asked again, even though I got the impression that they were willing to put up with it because they liked me. It never crossed my mind that I was humiliating them. They never brought that up. If they had, I wouldn't have done it the first time."

"How can you be so sure," Mandy interjected.

"Because I cared for them, and if you care for someone, you would never want to humiliate them. How can you love someone and enjoy degrading them?"

"You're so wrong!" she said emphatically. "It's because I love you that this is so hot. If you were just some guy I met at a bar, the emotional lightning wouldn't be there.

"It's because I love you so deeply and know you so well that I know exactly how you're reacting. The humiliation and shame radiating from you thrills me in a way that nothing else ever has. When you let me go all the way, I know I'll feel pleasure beyond anything I've ever known before. I'd like to experience that just once."

Lester stared at her as she spoke. Her voice was spooky, as if she was overdosing on drugs and had no idea what she was saying. Her eyes had a strange light in them.

He was silent for a while and then returned to the deal she had offered.

"Whether I'd like anal with you or not, I don't need it, and even if I did, I wouldn't let you put your hand up my ass for that. I felt like I was dying the night you ripped into me with three fingers, so any pleasure of making love to your ass wouldn't make up for my pain and humiliation.

"If you look at it logically, it doesn't make sense. You said that my cock is as thick as three fingers. So if we had anal sex, it would hurt you as much as the other night. But your three fingers hurt a lot, too, and you'd be putting your whole hand in. Why would I agree to that?"

edrider73
edrider73
1,064 Followers