Exploration

"You aren't looking at this right," she said. "Forget about numbers of fingers. Just think in terms of discomfort, humiliation and pain. My asshole is much smaller than yours, and you fucking it would hurt a lot more than you sticking your fingers in.

"Your fingers just go in a few inches, and that's enough to cause tremendous pain. Your cock is so long that you'd go halfway up my intestines and the pain would be many times worse.

"And the motion of your big cock -- especially when you work up a head of steam and start pounding me into the mattress -- I get frightened just thinking about it. I'm much softer and more fragile than you. I would use as much lube as I could, but you would still rip my insides to shreds. There's no way I could hurt you as much as you could hurt me."

"That all sounds great, Mandy," he said with a laugh. "We both know you're exaggerating what I would do to you and downplaying what you would do to me."

"I bet you my whole hand is about as wide as four of your fingers," she said. "I can measure right now. If I win, will you do it?"

"No. Because it comes down to this: When you see me overcome with pain and humiliation, it gives you tremendous orgasms. But hurting and demeaning you just doesn't do it for me."

"You promised to think about it, Lester," she said. "Take your time. I can wait."

"You may be waiting for a long time."

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

He pretended that he was giving it consideration. Then he got worried that he might be raising her hopes, so he told her three days later.

She was angry.

"So you're wimping out," she said. "I've seen lots of guys on the Internet letting women do that to them. It isn't the end of the world. And I'm not any woman. You know you'd be safe with me because I would never do anything that could cause you real injury. I'd be careful.

"You know how much I want this because of what I'd be willing to sacrifice to get it, and you still won't give it to me. I'm just not that important to you.

"I could do it to you anyway if I wanted, but instead I agreed to experience the horrible pain of anal sex to earn it fairly. But that didn't get me anywhere, did it? I need to get out of the apartment. I can't look at you."

He didn't say anything as she left, but he thought to himself, if she leaves me over this, I guess I don't know her as well as I thought I did.

When she came home a few hours later, she had calmed down, and the first thing she did was embrace him and kiss him for a long time.

"I'm sorry," she said finally. "I was so disappointed that I said terrible things I didn't mean. You know I love you, and this disagreement is never going to change that."

"So you're finally giving up?"

"I didn't say that," she said. "But I promise you there won't be any more scenes like today. I still want to do this, and I'm going to try to persuade you. I can see that logic won't work and neither will telling you how much it means to me. But there are other ways."

He didn't have to wait long to find out what she was talking about. The first email arrived a couple of weeks later. The messages with the links were always along the lines of "I think you'll find this interesting" or "Take a look at this one" or "Do you think she's enjoying this?"

He realized she must have subscribed to several websites specializing in anal porn. The links she sent were always to videos where the girls seemed to be petite, with bodies similar to Mandy's, and the men had huge equipment, usually larger than Lester's.

In each video, it was obvious that the girls were in extreme pain. Some of them tried to blink away the pain, some furrowed their brows and some of them tried to breathe fast or blow out air to lessen the pain, but by the end, all of them were screaming, and most of them had their eye makeup streaking down their faces from crying.

If there were any links showing women enjoying anal sex, she never sent them -- only the ones where the women were struggling with their pain as the men merrily pounded them.

At first, Lester was embarrassed that he was responding to the videos. He noticed that while watching them, he got hard.

One time, she walked into his home office while he was watching one, and he quickly shut off the video. She smiled at him and didn't say anything.

After a while, he decided that there wasn't anything wrong with his reaction. That's what the porn videos were for -- to turn men on. He enjoyed them and at times even looked forward to what bizarre video Mandy would send him next.

If the intention was to whet his appetite for having anal sex with Mandy, it didn't work. He did think about anal sex more now and sometimes imagined doing it with one of the porn actresses, but never with Mandy, because he knew what it would cost him.

One day at dinner, she brought up the videos.

"I can tell you're getting into them, Lester, and you know I'm sending them to whet your appetite for anal sex with me, so I can get what I want in return.

"But I have to tell you something else so you won't say later that I didn't warn you. I'm not waiting for you to tell me one day that you give up and agree to my proposition. I'd prefer that, but here's how I think it's going to happen.

"One of the nights when we are using a couple of fingers on each other, you'll finally give in and go for my ass with your cock. When you do that, I'll go along with whatever painful and disgusting things you do to me, because you'll be sealing the agreement. I'm going to get my end of the deal, so to speak, with or without your cooperation."

"Wait a second. You said before you could do it against my will. Are you going to drug me? Don't you think that's sick?"

"Of course, that would be sick," she said. "And there's an even better reason why I would never do that. The whole point of my sticking my hand into you is for me to watch you experience the pain and humiliation. I want to see you blubbering like a baby. I want to watch your eyes and expression as you turn into an imbecile and lose control of your facial muscles. I want to see your body squirm and twitch and shake uncontrollably. If you were drugged out and didn't even know what was going on, what would be the point?

"No, I worked out a way that I can do it to you, and when I do, you'll be totally awake but unable to stop me. Another woman might just go ahead and do it anyway, but I'm not like that. Everything's going to be fair. You get your anal first.

"You didn't let me finish my warning. There's another way you can seal the deal. If the videos work and you're dying for anal sex, you might think about doing it with someone else instead of me. Maybe you'll go to a whore.

"That won't work, Lester. It will seal our deal just as surely as if you do it with me. I'll find out about it and take what you owe me. If you do that, it will actually be easier on me, because I won't have to give you my ass."

Lester looked at her in astonishment.

"It sounds like you'd be happy if I had sex with a prostitute."

"I would hope you'd use a condom and make her prove she's not HIV positive," Mandy said. "I don't want you to die. But you're right. I wouldn't consider it cheating because I'm giving you permission to get anal from her so I can get what I want.

"Let's be clear, though. If you had regular sex with another woman, that would be betrayal and cheating, and it would mean the end of us. You'd feel the same way if I had sex with another man.

"But if you have anal sex with another woman, I'll be happy, because it means I get my once-in-a-lifetime fantasy without having to endure you ravaging my ass. I'll remind you again that you don't need to do that, because I'm offering it to you whenever you want.

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

She didn't mention her warning again, and Lester forgot about it because he had never once been tempted, to cheat although there had been many opportunities. Both he and Mandy traveled on business occasionally.

One of the local opportunities was Carol, who lived on the floor above them and was wild. They enjoyed going to her parties because they always met strange and unusual people that they would never ordinarily come in contact with. Carol and Mandy became close, and when she would come over to see Mandy, his eyes would always bug out.

Carol didn't just like to wear next to nothing. She went one step further and wore clothes that pointed to all the best parts of her geography. Her large breasts always looked like they were falling out of whatever she was wearing and her shorts were tight and skimpy, often exposing a bit of colorful thong.

She constantly flirted with Lester, whether Mandy was there or not, and when she did, her words were so graphic that Lester wondered if she was really joking.

When he told Mandy about her grabbing his butt or groping for his cock, the response was barely a shrug. He was surprised at first because Mandy made no bones about how possessive and jealous she was. She joked that if she ever got married, her pre-nup would give her the right to kill her husband if he ever strayed.

Lester finally got it. Carol was Mandy's cheat tester. Carol probably reported every provocation to her, along with his reaction.

Maybe it was because he was watching too much anal porn, Lester thought, but lately Carol's ass was really catching his attention. She had switched from denim shorts to yoga pants that were so tight and thin that they looked like they had been painted on. She wore nothing on under them.

Whenever he saw her, whether it was her visits to Mandy, on the stairs or in the laundry room, it always seemed as though Carol was bent over with her legs wide. One time, she was wearing some yellow pants that were so sheer he thought her ass was winking at him and telling him, "Come and get me."

He finally shook his head to snap out of it and hoped Carol didn't notice him staring. It made him decide not to watch the video links that Mandy was sending him, but he didn't keep that resolution for long.

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

"I'm sorry, Lester, I found out this morning," Mandy said. "We'll just postpone our plans to next weekend. The weather is supposed to stay good."

"How could they make you do this at the last moment," he said. "I should call Franny and tell her how it's wrecking our getaway."

Mandy's boss had grown up next door to him, and his influence had been instrumental in getting Mandy a job when things were tight.

"No!" Mandy said in a loud voice. "I don't want you calling Franny. Even if she could let me off, everyone at the office would hate me. Don't you dare call Franny or ever mention our trip. I just told you we're not canceling it, just postponing it a week."

"All right, I won't," he said. "Is everything all right at work? You seem really on edge?"

"I'm fine, but I've got to pack, so I can leave first thing in the morning," she said. "It will be over late tomorrow night, so I'll drive back Sunday morning. I should be home by noon. What are you going to do?"

"I don't know," he said. "The whole weekend's shot to hell."

"Carol's having one of her parties," she said. "We were invited, but I didn't bother to tell you because we had plans. If you end up going, don't drink yourself under the table just because you're angry."

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

Friday night two weeks later, Lester was still in a good mood from the previous weekend. They had taken their postponed trip, and it couldn't have been more perfect. The lodge was wonderful, the food was great and the grounds were beautiful, but the best thing about it had been Mandy. She had stopped being irritable and peevish like she had been for the previous few months.

All of a sudden, she was relaxed and eager to do whatever he wanted. She was warm and tender, and all her attention was devoted to making him happy, even though he had planned the trip to please her.

In bed, she was like a rabbit. She always liked to make him feel good during sex, but for the whole weekend, she didn't even think about herself. He noticed that the more excited she made him, the more excited she became. And that in turn aroused him even more, so it was a spiral of lust that ended with both of them exhausted by the time they got home late Sunday night.

He left his office early every day that week as he made the rounds of local jewelers to select an engagement ring. He had been thinking about it for a while, but had hesitated because of Mandy's recent behavior. The last two weeks had convinced him the time was right.

The glow of their getaway hadn't worn off by Friday, and though he would have preferred some more wrestling in the sheets this Friday night, it was one of their scheduled finger pushing sessions, and he knew they meant a lot to Mandy. She had been smiling broadly all through dinner, and he was sure it was because she was anticipating bedtime.

They were side by side in a sixty-nine position. Her two fingers were working away inside him, and his were doing the same inside her. He was waiting for her to move their bodies into whatever position she wanted to for them to consummate when he felt it.

"Hey!" he shouted. "Stop that!"

But it didn't stop. He felt a third finger sliding into him. It didn't hurt because he was lubed and loosened from the pushing and pulling of her two fingers, but it bothered him anyway.

"You told me you never wanted to use three fingers again," he said, trying to turn head toward her. He didn't see her face because her upper body was down by his crotch, but he could hear her reply.

"I didn't say that, Lester," she said. "What I said was that I would never let you put three of your fingers inside me again."

"But that's what I'm going to do, Mandy," he said, "I told you before, a finger for a finger."

"Not anymore," she said, "and this is why."

"Ow!" he said as he doubled up in pain. "What was that? You've never done that before. That was cruel."

"I'm sorry, Lester," she said. "Please be quiet for a minute. I don't want to do that again, but I will if I have to. Will you listen to me for a minute? After that, you can say anything you want.

"I said you weren't going to put another finger in me, and you just found out the reason why. I have three fingers in your asshole. There's a ton of lube in there. I can hear the squishy sounds as they go in and out. I'm going to keep gradually increase the pace.

"There are two reasons you're going to let me do that. The first is that I just attached restraints to each of your ankles and fastened them to the bedposts. Yes, try to move your legs. See, you can't get them free. They'll move a few inches, but that's all.

"The second reason you won't stop me is that is my left hand has a good grip on your balls. The grip is snug, and I hope your balls feel comfortably warm. Right now, you need to take both fingers out of my ass, and you are not going to put any of them back in tonight.

"Did you understand what I said, Lester. Take those fingers out now, because otherwise I'll squeeze your balls as hard as I did a second ago. Don't worry if you pass out. I've got some smelling salts handy, and you'll soon be awake again. I want you involved with me as I put my hand into your ass tonight."

"No!" he screamed. "Are you crazy? Why are you doing this?"

"I'm not listening, Lester, because your fingers are still in my ass. If you don't remove them slowly right now, get ready for some real pain. That's it. Slowly slide them out. Now hold still."

She slid off his face and down his body until she was on his stomach. She bounced on it once, and all the air went out of him. As he was gasping, she pulled her fingers out of him, turned around, reached under the bed and pulled up a restraint that she attached to his right wrist. She finished doing the same to his left wrist just as recovered enough to begin struggling.

She got up, stood by the bed and watched his body twisting. His arms and legs could move freely but not enough to let him get to the fastenings. When he stopped moving for a moment to catch his breath, she jumped back on the bed and was soon sitting on his stomach again facing his feet, with three of her fingers going in and out of his ass. He stopped struggling, but his body couldn't keep from squirming. After a minute, she spoke.

"Did you feel my fourth finger going in? It's going in and out almost as easy as three. I told you that you could take four.

"Now I'll answer your question. Why am I doing this? It's simple. Because you sealed the deal.

"Do you have anything to say, Lester, any questions? Are you thinking about telling me any lies? Are you going to say it's your word against hers? You can save your breath, because I know for certain what you did. Did you see all those lights go on? Here she is, the beautiful Carol.

"She is such a slut. Look, she even took her clothes off. No, we're not having a threesome. She's holding that video camera because she's been shooting us from across the room since we got into bed.

"Now that she's come out of hiding, she can turn on all the extra lights I rented, so the video is bright and crystal clear. Everything is being shot in slow motion as well as regular speed. I'll be able to watch my hand going in you bit by bit and see how your body and your face react.

"I know all about Carol's party, and how drunk you got and how you were lying on her couch when everyone else left and how she danced her slutty dance and shook her butt for you in her yoga pants.

"Despite all the drinks, you were hard as a rock. You were so drunk that you forgot about everything except her butt. You took forever to get your shorts off, but only a couple of seconds to pull her tights down to her knees and stick your cock in her ass. You were so excited that you gushed into her guts in less than a minute.

"It didn't do much for you, but it bought me my ticket for tonight.

"Was that moan because I stuck my thumb behind my fingers and I've got all five going into you? Can you feel me inside up to my second knuckles?"

She kept up the movement as Lester began blowing out to try to deal with the pain. His eyes were wide and sometimes they went blank as his eyeballs went back into his head from the agony he felt.

Mandy slowed down the movement until she stopped with her five fingers inside him. Then she began pushing again, not hard but relentlessly. The largest widest part of her hand reached his opening and was stopped, but she kept pushing, increasing the pressure slightly.

Lester began howling like a wounded animal, and then Mandy's hand burst into him, and he screamed one loud scream and dissolved into sobs.

"Oh, oh, oh," said Mandy. "I just came again. Your ass just swallowed my hand up to the wrist. It looked amazing. Poor Lester, you're bellowing like a little boy who scraped his knee. Your pathetic voice is getting me even more excited."

After a minute, she bunched her fingers together and slowly pulled them out. The instant they were free, she pushed them right back in, and he screamed again.

"It went in easier that time," she observed as she pulled her hand out and plunged it in again. She slowly increased the pace, and each time she pulled her hand out, his body jerked violently.

"I just came again," she said. "I think I could keep coming all night if we kept this up, but I don't want to turn you into a vegetable. So we're going to try something so hot that I came the other day just thinking about it.

"I want to make you come you come at the same time you are utterly degraded and in tremendous discomfort. Can I carry that off? Can I give you a great orgasm while you're feeling horrible?"

She maintained the steady rhythm of her right hand going in and out, punctuated by his soft cries because he barely had any strength left. She leaned over and sucked him into her mouth and began working on him with her tongue as she sucked hard. Her left hand began gently fondling his balls.