My Weekend with George & Alice Ch. 05

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He takes Alice's anal cherry as weekend continues.
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Part 5 of the 7 part series

Updated 10/21/2022
Created 09/09/2005
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Peter_
Peter_
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Author's note:

First, I would like to acknowledge and thank Wagoneer88 for his efforts in proofreading and editing this story.

This is a continuation of a story separated into several parts. For it to make sense you really should read the whole thing, in order.

Lastly, if you haven't read the Author's note at the beginning of Part 1, PLEASE do so.

Peter

Now on to the story:

My Weekend with George and Alice
Part 5

Next I went to my bag and got out most of the toys that were still inside. One by one I laid them on the bed; a butt plug, substantially bigger than the one from the day before, just slightly smaller in length and girth than my cock; the crop that I mentioned, but hadn't shown them yet; some clothespins; some more weights that could be hung from the chain between the clamps; a rather large dildo, that had a built-in vibrator; and lastly a leather paddle. It was padded and while it would smart, it was nothing compared to the crop. I also laid the nipple clamps, chain and weight there.

"Now, I think we are all set for some fun. Georgie, yesterday you kept me from using anything but the plug on Alice, and that was really just to make it easier for her when I fuck her ass, which I definitely intend to do soon. But first I think I'll make up for yesterday when I didn't get to use any of these fun things on her. I could start with the dildo, but I think she'd like that too much!" I laughed at my own joke.

Alice actually blushed a bit, telling me it was true, and that she probably had one of her own that George was totally unaware of.

"Actually, Georgie, if you really want to spare her again, I'm going to give you a chance, but it will be much, much harder this time. The key is the crop. This baby can really sting an ass." As I spoke I picked it up and cracked it against my palm. It makes a REALLY loud noise when you do that, and it actually stung my hand quite a bit. If I were to use this and not brutalize someone, I'd have to be careful. "But it is particularly nasty on other body parts, the back and inside of thighs is quite interesting. The breasts, especially the nipples can be quite severe too, but the place that is pure, hellish torture is the pussy and especially if you should happen to catch the clit!" Talking about this was having a morbidly exciting affect on me and I was wearing that evil grin again. George had lost all blood to his head it looked like, and Alice was clearly uncomfortable with my attitude.

I walked over to Alice still holding the crop. "So, let me tell you both what I have in mind for this pretty lady. It is a very wicked game of sorts. We'll put this large plug in place, attach the clamps, hang not one, but three weights from them, one on a chain between the clamps and one more on each end dangling freely from each clamp. It has the effect of pulling rather sharply and in more than one direction at a time if you move at all, and with what else will be going on, I'm sure you'll move plenty. Anyway, once that is done, the game begins. Alice will be on all fours and I will start using the crop on her ass, maybe drifting down to her thighs occasionally. I will count the strokes and when I get to fifty I'll stop and we're done. I will stop any time sooner if Alice only asks! Of course there is a catch. For every ten, or portion of ten, strokes left, she will receive one flick on each breast, and one on her pussy. If that stroke happens to hit her nipple, which is extraordinarily sensitive right after removing those clamps, or her clit, well that's just one of the risks."

I looked directly at each of them in turn. George looked petrified, Alice looked calm. That actually unnerved me a bit!

"So Georgie, shall I start now or are you going to try and save your damsel in distress again?"

George was very pale, and his voice shook, "Please don't. PLEASE, don't do this!"

I was actually starting to feel sorry for George, although if his erection was a true indicator, he was still enjoying himself in some strange (at least to me) sort of way.

"Georgie, I'll tell you what, you propose an alternative activity and if I think it is equal to what I just described, I'll do what you suggest instead, okay?" George knew exactly what I was alluding to.

"Please, please don't do this. Leave her alone, please!" he said softly with a still shaky voice.

"No can do Georgie. Okay Alice, looks like your hubby is letting you down. Let's get started," I said with bravado.

Alice just looked at me and smiled. BOING, she didn't think I was going to go through with it.

"WAIT! Use the crop on me instead," George said in an especially pitiful voice.

"Georgie, I'm getting impatient. I'm giving you one more chance to make a proposal. If it isn't specific and sufficient, I'm starting in on Alice, get it?"

I looked at Alice. She didn't seem quite so confident all of a sudden, but she was still very calm.

"OKAY, Okay, uhh . . . okay, use it on my cock and balls. You were going to do either 50 strokes on Alice's ass or as many as 15 total on her tits and pussy. Do 15 on my cock and balls," George squeaked. He look absolutely terrified.

I looked at Alice again. Now she looked very worried and concerned.

"Georgie, there is no way you could take that.But I'm so impressed that you offered, I'll tone it down a little and we'll do as you suggest. You really will do anything for her, won't you?" It was another rhetorical question. I couldn't believe he had risked what he did to keep me from torturing Alice. I don't think she could either.

They both let out a deep breath when I said that.

I motioned Alice over to the corner of the room where I knew George wouldn't be able to overhear us. "You don't think I'd do it to you do you?" I asked very seriously.

Cautiously she softly replied, "No, I don't. You aren't that cruel, even though you want to act as if you are."

"Are you really sure?" I asked, staring hard into her eyes.

"Not totally, but pretty much, yes."

"Okay, I'm going to play Georgie along a bit more, and if you say a word to give it away, I WILL do what I said to you! When I tell you to start, you slap him once on each nut with the crop, while I count. Make sure it stings plenty, but that's all. I don't want him to throw up, pass out, or especially end up in the hospital. Do you think you can do that? Hard enough, but not too hard?"

"I can do it," she said with great confidence.

"Okay Georgie, here it is. First, I told you I wouldn't touch you, not even with this crop, so Alice is going to do the honors. But just in case you think that means you'll get off easy, I just told her if I think she eases up one bit, I'll still play my little game with her even after you get yours! She is going to smack your balls with the crop, while I count. Neither of you will know how many times until I stop counting. She'll alternate balls, left on even numbers, right on odd. But first Alice, I want his little balls very sensitive, so you do your little hand job thing and bring him as close as you dare. I don't need to tell you what happens if he cums."

Alice was just standing there. "NOW! Or else!"

She immediately moved into action. I trusted that she would push him as far as she dared, but in his current condition that only took about two minutes. From the look on his face I could tell he was hopelessly in need of cumming and had a horrendous ache in is sac.

"Okay Alice, here is the crop. Get ready."

She stood next to the chair, but her aim was going to be very awkward. "Wait, let's give you a better target, with a bit more leverage." And with that I tilted him back on to the floor again. Now she had a clear shot straight down on his balls and his dick was out of the way. This would definitely smart!

"Okay, everybody ready?"

George cringed and squeezed his eyes shut. Alice simply said, "I'm ready" softly.

"Okay, here we go. ONE"

George let out a blood-curdling scream as Alice smartly slapped his left nut. She had done exactly as instructed. It was clearly hard enough to hurt like hell, but not so hard as to injure him or hurt so bad his body had to react violently.

"And again, TWO"

Again George screamed. He was in even more pain than after the weight, in part because his balls were so much more tender now, but also this was more brutal even than that. I knew he couldn't take any more.

"All right, ready?" I said menacingly. George was just moaning, but Alice started to say something, then bit her tongue.

George wasn't looking, but I took the crop from Alice then said "THREE"

George jerked almost as if he had been hit again, then after a long pause he opened his eyes.

I was looking down at him, "Hi Georgie." The puzzled look on his face eliminated any need for a question "I don't want you to miss what I'm going to do to Alice and you couldn't take any more without losing it!" He gave a bit of a nod, but said nothing. It told me I was right, however. Any more pain and we would have lost him. He was hurting plenty as it was, but I had no doubt that his little erection (which was gone for only the second time since we had started the day before) would be back soon.

"Besides, Alice was far too easy on you, so I'm going to do her just as I said I would!" I said with a big smirk. Looking at Alice, I saw that she was still calm.

George was another matter. He was still willing to do anything to spare Alice, "WAIT! Let her try again, harder this time. I can take it, I know I can!"

I could NOT believe this. I looked at Alice and she had that evil bitch smile on again.

"Well Alice, shall we give him another taste, only good and hard this time?" I asked, wondering if she would really do it. I knew George really couldn't take any more, and she must have too. I couldn't imagine that George thought he could, but evidently he would do whatever it took to keep Alice from the pain I'd described.

Alice looked at me with what could be described as only a testing look. "Yeah, let me whack him really hard this time. I sure don't want you using this thing on me!"

Once again it was clear, Alice didn't think I'd do it. I was becoming unsure as to what I should make of that.

"Georgie, can you imagine what it would feel like if I let Alice do this, and as hard as she could? She would though you know. She is not only a slut, but a very selfish one at that. But Georgie, I'm basically a nice guy, so we're done punishing your nuts for today. At least physical punishment. I think what is going to happen yet, will continue to increase the ache. Especially if we throw in a little more of Alice's brinkmanship, and we will absolutely do that!" I laughed.

The relief on George's face was total. I'm sure he would have jumped up and kissed me if he could have.

There was much about George I didn't understand or identify with. I lifted his chair back to its upright position.

Alice and I sat across the room, drinking a second cup of coffee, just chatting and getting to know each other a little better, while we waited for George to recover enough to concentrate again. Sitting there naked with her, just visiting as if we were anywhere and fully clothed, was a very erotic experience. This was a fantastic woman and I was becoming enthralled.

She told me that she was sure what George was going through was right in line with his fantasies. She even thanked me, because this was far more than she or he had anticipated and she knew she was loving it and that George was too. She went so far as to say that what I'd had her do to George wasn't that far beyond what they often did on their own, but it was somewhat, which she was sure was a complete turn-on for George. She admitted that treating him so badly was very much a turn on for her! She unabashedly also said that she was loving having sex with a real cock, something she had never done in her life. As I had suspected, both she and George had been virgins when they married. She may not have been a very experienced lover, but she was beyond doubt a natural.

I was enjoying the situation so much I essentially lost track of the time. But I happened to glance over at George and any doubt I had that this was not to his liking vanished. His little dick was sticking straight up. He was gazing at his wife's profile. With the light from the window behind her, she would look like a silhouette from his vantage point, and I'm sure that her ample breasts would look as if they glowed. I couldn't blame him for being turned on by that, but I was sure if my balls had suffered through what his had I wouldn't be hard. I don't care how long it had been since I came last!

Softly I said to Alice, "Looks like Georgie is ready for more."

She looked over at him and laughed gently. It was very sexy!

We stood and went over near him. "Georgie, I've been planning on fucking your wife in the ass ever since she and I made these arrangements. Once I saw it, I became obsessed with sticking my dick up her tush. But just to show you what a complete and total slut she is for a real cock, I'm going to give her the choice. If she doesn't ASK me to fuck her ass, I'm not going to."

This brought a shocked look to Alice's face. She was now faced with a dilemma, which was exactly my plan. I was positive she actually wanted to experience getting fucked in the ass, but she'd been going on the basis of having no choice. Now she was going to have to ask for it, to experience it. A big step for her, I knew.

Nonetheless it didn't take long. "I want you to fuck my ass. I want to feel that big hard cock deep in my ass. I want you to pump it hard inside me and cum deep in my bowels." She said this with such a passion that no one could have thought she wasn't dead serious.

George looked even more deflated.

I went to the bed and got the big butt plug. "Want me to loosen you up a little? It will make it easier on you," I said sincerely.

"Nope, I want the big hard cock inside me now. I want to feel you stretch my asshole and shoot cum up there!" She wasn't playing the role; she was being an unconditional slut!

I must admit, while I was hard already, that made my cock swell to its full proportions.

Unable to resist teasing her a bit more, "Okay, bend over and here it comes, or do you want me to lube it up a bit first?"

Not to be outdone, she went to my bag and looked inside. Finding what she expected to, she returned to me with a bottle of Astroglide. "No, let me do it!"

She poured a generous amount onto her palms and proceeded to give me the beginning of a fantastic hand job, leaving an ample amount of lube on my cock as she did so. She had me racing toward orgasm in no time. I'm sure she (rightly) figured that would make me cum faster once I was inside her. She may have wanted this, but she still had some apprehension as to what it would really be like.

"Okay, up on the bed, on all fours!"

Alice giggled as she crawled into position, her ass pointing straight at George so he wouldn't miss a thing. I felt like I was no longer fully in control of the situation. Alice had a way of taking over that was very subtle (well, actually not all that subtle as I think about it).

I picked up the leather paddle, and said, "We need to warm your ass up a little first," trying to take back the control.

Alice just smiled at me. "Okay, I'm ready."

I gave her several rather hard smacks on each cheek with the paddle. It was designed as a toy not a punishment device though, and so while it made a loud noise it delivered nothing more than a light sting. It did have the effect of turning her white ass a very sexy pink. The action and the visual turned me on even more. It just made Alice moan, and not out of pain.

"Head down on the bed." As I climbed on the bed behind her, Alice took the Astroglide and put some more on her right index and middle fingers, and worked it around and into her puckered rosebud.

As soon as she put her hand back on the bed, I positioned myself and placed the head of my cock against her sphincter. "Relax now," I encouraged. I really didn't want this to hurt her because I was hoping she would actually enjoy it and want more!

I used the head of my cock to rim her hole, smearing the lube all over me and her opening, so as to make the first penetration as easy as possible. When I felt that she had relaxed a little I positioned the head of my cock right over her hole again and started to apply pressure. She tensed again.

Without stopping the pressure I softly whispered for her to relax, and gently stroked her ass. She took a deep breath and blew it out, I felt her sphincter relax and my cock head started to slide in. I slowly, but steadily kept pushing until my whole head disappeared inside her. I stopped for a few seconds to let her get used to the feeling.

I held her hips firmly and pulled her toward me as I pushed my cock deeper and deeper. When I would feel her tense, I'd stop and tell her to relax. Damn she was tight, and did it ever feel good to my cock. I wanted this to last as long as possible, which wasn't going to be easy as tightly as my cock was being gripped. Finally after several minutes I was balls deep inside her.

"Okay?" I asked.

"Mm hmm," she nodded and moaned.

"Okay, then I'm going to start slowly," which I did. Soon I was stroking in and out of her. I'd pull back until my cock head was just inside and the whole shaft was out, and then start back in. Slow and steady, in and out, faster and faster. Soon I was fucking her with a good steady pace. She was moaning constantly.

"Okay?" I asked again.

This time I got a more enthusiastic reply, "Oh YEAH!"

She was getting looser and looser, not loose mind you, just not gripping my cock so hard. It felt better and better as she stretched out. I'm sure it did to her too.

I picked up the pace a little. I was getting pretty close to cumming.

"Finger yourself," I said softly. I sensed her hesitation, so much louder I said, "I want Georgie to see that a real cock can make you cum even when it's up your virgin ass!"

That was all it took, she started fingering herself for all she was worth. Soon I could feel the spasms in her cunt. That did it.

"F U C K!" I yelled. The orgasm I experienced was as powerful as any of the earlier ones. That did it for her too; she came with me, letting out a loud growl of her own. I kept pumping until my load was done and we both collapsed on the bed.

Somewhat to my surprise she lay there for only a minute and then got up. Puzzled I just watched.

"Well Georgie, (now she was doing it too) we've seen that your dickie just isn't big enough for me to feel inside my pussy any more, let's see if I can even feel it in my ass now that it's been reamed out." And she went over and turned her back to him and sat in his lap while she guided his little penis into her bum.

I quickly moved over to observe, now that I knew what she was up to, but remained silent.

"Is it all the way in Georgie?" she asked in a nasty voice.

"Yes," he whimpered.

"Can you feel anything, 'cause I sure can't!" she giggled.

She started to work up and down, "How about now? I still can't, can you?"

"No," he whimpered even more pitifully.

She stood up, "Well let's see, neither of us can feel his cock inside me, not even in my ass. His tongue isn't capable of giving me pleasure. Hell, I guess all that's left is for him to use that worthless little tongue to clean a real man's cum out of my various holes!" she laughed wickedly.

I took the hint and laid the chair on the floor one more time. She squatted over his face and simply said, "Clean me Georgie".

I could tell he wasn't responding. "Georgie, lick the cum out of my ass now if you want any hope of cumming when this is all over." George and I both had no doubt she meant it.

Peter_
Peter_
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