Costume Party Ch. 03

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Scott continues to ravish Callie.
4.2k words
4.69
51.9k
11

Part 3 of the 6 part series

Updated 10/11/2022
Created 01/17/2005
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The following totally fictitious writings and are intended for the sole readership of those of LEGAL AGE. The ADULT ONLY material contained within is also for personal use only where local standards permit scenes of violence and sex. Please do not read further if any of these subjects offend, or if you are not of legal age.

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I stood behind her and started to finger her pussy and rub her clit. To my pleasure, I found her already quite wet in anticipation of whatever was going to come. It was only a very short time before she was again moaning with pleasure. I got her good and worked up before I stopped.

As I pulled my fingers out of her she let out an involuntary groan.

"Now sweetheart, I'm going to give you a little challenge. I'm going to feed you my cock" I began explaining as I removed my sweats.

"Your goal is to take the entire length down your throat!"

"You know I can't do that! You'll choke me to death!" she yelled.

"Shhh, I think you can, but to encourage you, I'm going to give you an incentive. If you are successful, I'll turn you loose and we can spend the rest of our time together however you please. But! if you aren't, then I'm going to put my cock in the other end! And if I do that, I'm not just going to stick it in and then take it out, I'm going to fuck your ass until I cum" I said rather evilly.

"NO! You can't! You'd tear me apart, besides, I've nev. . ." she stopped abruptly, but it was too late.

She'd realized that letting me know she was an anal virgin was a bad idea, but it had slipped out before she could stop in time.

"Wow, I might just get your anal cherry, huh?" I chuckled.

She didn't respond.

"Well, in that case, maybe we should loosen you up a little first, just in case!" I went on.

I'd intended to do this all along, but used her 'virginity' as an excuse. I picked up some lube and a medium sized butt plug that I'd laid out, but she couldn't see exactly what I had. The plug was only about half as thick as me and not all that long, but it would in fact serve to loosen her up some. I had no doubt she was not going to 'win' this challenge and that shortly I'd be replacing the butt plug with my throbbing cock.

I moved behind her again and lubed up a couple of fingers. I started working on her rosebud with just the tip of one. I could feel her tense, but in spite of herself, after a couple of minutes she started to moan softly. She was every bit the slut I thought!

Slowly and gently I worked the finger inside her, twisting it and sliding it in and out. Then I added a second finger and did the same thing until I had two fingers clear up to the knuckle in her tush. Finally I pulled them out and took the plug. After a liberal application of lube I placed the tip at the opening of her ass and just held it there.

I could see her whole body tense.

"Relax" I said soothingly.

I continued to just hold it in place, not exerting any pressure.

"Relax," I repeated, "It will hurt a lot less if you do!"

I could tell she was trying. Once she managed to make some progress I started to apply the slightest bit of pressure.

"Relax," I said yet again as I pushed a bit harder. The plug disappeared about two inches, the widest part approaching her stretching asshole.

"OW! OW! Please stop!" she whined.

"Relax, or I'm just going to ram it home!" I said forcefully while still keeping a nice steady pressure on it.

Once again she worked very hard at relaxing, as she did the plug started to slide deeper and deeper. Finally as the widest part was stretching her sphincter it popped into place and the base smacked against her ass.

"AHHG!" she yelled, but it was now firmly imbedded in her.

I tapped on it lightly, chuckling.

She grunted.

"PLEASE Scott, it hurts! Take it out, PLEASE," She begged.

So far, while I'd treated her a bit roughly, I hadn't given her the mean treatment. If I was going to achieve what I wanted, it was time.

"Too fucking bad! If you think that hurts, wait until I started pounding in and out of there. Now you really have a reason to get my whole cock down your throat, don't you?" I barked.

She sniffled a few times, but didn't say anything.

I moved to her head, "Open wide"!"

"Please, PLEASE don't do this!" she begged again.

"Look, do you want to try or shall I just pull out the butt plug and replace it with my cock right now?" I asked menacingly.

"NO!" she shouted, "I'll try!"

"Then open up" I said

She did, as wide as she could.

Slowly I began to push my cock in her mouth. Her cheeks bulged almost obscenely as the fat cock head filled her mouth. Still slowly, but steadily I fed her more and more until I felt the tip reach the entrance to her throat. I paused for a moment, letting her get use to that much. It was already more than she'd taken the night before.

"Okay, here we go!" I warned.

And very slowly I started to stuff even more cock in her. I could sense she was trying to pull away, but it was hopeless the way I had her secured. Bit by bit I inserted more cock, a fraction of an inch at a time. I felt her start to gag and pulled back ever so slightly. She still had only about half of the whole thing. She was never going to make it I knew.

"Okay, here is some more" I told her as I started to push again.

I got about another half inch in before she started to gag again. She tried to control it, but I kept pushing this time. It was too much, she was seriously gagging now. I waited a couple of seconds and then pulled all the way out.

She coughed and choked and gasped for air.

Without really giving her time to recover I started to move behind her, "Well, I guess I'm just going to have to fuck you in the ass after all!"

This entire situation was turning me on tremendously. I genuinely hoped she was going to want to do as much more of this in the future as I was. I'd know soon enough.

"NO! NO WAIT!" she screamed, "let me try again, please! PLEASE!"

She was really scared about me fucking her up the ass. Good!

More kindly than I'd been for quiet a few minutes I said, "Okay, rest a minute and you can try once more."

I walked away for a couple of minutes with a raging hard on while she recovered.

Finally I came back and still softly asked, "Ready?"

She just nodded her head.

I pressed my cock softly against her lips and let her open at her own pace, which she quickly did.

"Just grunt when you want me to stop, and again when you want more, but I'm not pulling back this time. I'll go slow, honest!" I said, wanting to give her a chance that I knew wouldn't matter, but I was hopeful that in the future she might get as talented at this as two other women I could think of. She certainly was off to a good start.

Slowly but surely I inserted my cock between her lips until the head was approaching her throat again. She grunted. I stopped. I heard her take some deep breaths through her nose, her mouth was far too full to breath that way, and then I felt her relax a bit.

After a moment she grunted again. I started to feed her more cock. When the very tip of my cock started to enter her throat she grunted once more. As I'd told her, I stopped, but didn't pull back at all. I could feel her throat having little spasms, but she managed it and after a long pause she grunted once more.

I went very slow, loading more and more cock between her lips, a millimeter at a time now. I was deeper than ever before, more than half of my cock had disappeared between those luscious lips, but there was still a lot of meat to go. Suddenly she had a major gag. Even though she really hadn't grunted I stopped, but I still wouldn't withdraw one little bit.

I could sense her trying to get control of her gag reflex. She was swallowing and breathing fast and furious through her nose. I stood motionless, but the sensations on my cock were quite astonishing. I'm not sure I'd ever felt anything quite like it. I wanted so much to jam the whole thing down her throat and cum! But I restrained myself, with much difficulty I'll admit.

Just as I thought she might actually be able to take even more she started to gag violently. I waited just long enough to know she was truly in distress before swiftly removing my man meat from her mouth.

She continued to gag and cough and actually wretched a bit, but other than coughing for a while she was okay.

I gave her almost no time at all to recover before switching back to my 'mean mode'. Long ago I'd learned that keeping a sub off balance, especially a newbie, was critical to success. Besides, it made me hot as Hell. That would actually work to her advantage when I started to fuck her ass, because I'd cum more quickly and the less time in her chute, the better. From her perspective at least!

She'd actually managed to take around eight inches, not at all a bad effort. I knew she had some significant experience with cocks in her mouth! I was confident that given the chance, we could get the whole thing down her gullet. I was certainly looking forward to practicing.

I bent down and gently turned her head to the side. I planted a gentle kiss on her cheek.

"That was a very good effort baby. Maybe next time you'll get it all, but for now, I guess I have to put it somewhere else that's warm!" I said softly, but with a very evil overtone.

"NO! OH GOD, NO! PLEASE SCOTT! You'll tear me apart, you know you will!" she shrieked.

In my most soothing voice I said, "Not if you cooperate. I'm going to do this, but if you behave, you'll be able to stand it. Oh, it will hurt like Hell, but you'll get through it if you do what I tell you!"

Evidently resigned she said, "Okay, what do I do?"

"Just listen and do what I tell you!" I said firmly.

Since I hadn't, and wasn't going to, give her a safe word, I'd have to be careful. After all, I enjoy feeling the fear and pain of the woman. I'm definitely sadistic at times, but I'm not an animal, or worse a rapist!

She'd have a safe word, without knowing it. It would be up to me to tell if she'd used it.

"First" I said unkindly, "I'm going to help you by giving you something to distract you from the pain"

And with that I went to the table and retrieved the nipple clamps I'd left there. They weren't particularly nasty, but they would be quite effective, especially when she moved, once I'd attached the weights on springs. I attached the clamps and then quickly hung the weights.

"FUCK! Oh GOD those hurt!" she roared.

"Shh! You'll get use to them soon. And they will help, believe me. Now remember! LISTEN and do what I tell you!" I commanded.

There was NO WAY this wouldn't hurt like Hell, especially given that it was her first time. I hoped that the fear would do what it was intended to do. I also hoped that the eroticism would come through for her too! It was time to find out.

I moved behind her for real this time, and began to play with her pussy. I worked a couple of fingers in and out being sure to apply pressure to her clit as well. I found her G spot again and kept rubbing right over it. She was starting to squirm and moan with delight.

I kept it up until she was flooding my hand with her cunt juice. Without stopping, I grasped the base of the plug with the other.

"Take a deep breath. Let it out, and relax as much as you can!" I instructed.

She did exactly as I'd told her. That was a good sign. I smoothly and quickly extracted the plug.

"Oh shit!" she moaned.

I reached over and poured a large amount of lube on the fingers of my right hand and started to work two into her asshole before it had completely tighten up after the removal of the plug. My left hand went back to her cunt.

I was getting her thoroughly worked up as well as assuring her ass was well lubricated. If this was going to have any chance of working I couldn't under do the amount of lube in her ass.

It was time. I poured lube on my cock until it was dripping off onto the floor then placed the head against her opening. I felt her tense again.

"Now, RELAX! We can do this baby. I promise I'll go real slow, as long as you do what I tell you. Take deep breaths. Pant if it gets real hard, but not for too long or you'll get light headed" I said, wanting her to get through this.

She groaned again but said nothing. She nodded yes and I began to push. There was no point in going too slow until I at least had the entire head inside her. I kept up the pressure and watched the rather erotic sight of her asshole stretching around my cock head. It took a while but soon the thickest part of the head reached her anus and the skin enveloped the whole thing.

"Ow, oh OW!" she cried and started to pant like I'd told her.

I stopped and stroked her ass gently.

"You're doing real good sweetheart, just stay relaxed," I said softly.

She stopped panting after a little while and was taking deep breaths. Some of the tension went out of her so I pressed on, but slowly. I was able to very slowly keep pushing and burying more and more cock inside her. I had about eight inches in when I felt her tense up again.

"GOD SCOTT, It hurts soo bad! I don't think I can do this! PLEASE!" she yelled.

The fact that she hadn't actually asked me to stop or pull out was not lost on me. I stopped moving.

"Pant!" I said firmly.

She did.

While she was doing that I said, "Baby, you're doing great. We're almost there, just a little bit more!"

It wasn't quite true, but I figured she could use the encouragement. Then I decided to go for broke.

I leaned over her and whispered, "You can do this baby. You WANT to do this, don't you?"

She stopped panting and went back to taking real deep breaths. At the same time she responded.

She nodded her head and even got out a "Uh hum"

Her reaction thrilled me, so much that I swear I felt my cock swell even more. We were absolutely going to finish this now! I was so cranked up that it was not going to take long to pump my load in her once I was able to start stroking, which was a good thing all the way around.

I still had the bottle of lube in my hand and I poured so much more over the part of the shaft that was still exposed that it ran off. I dropped the bottle to the floor. Then I started to push. Harder and more steadily than before. I needed to get all the way in her so we could both move on.

"OW GOD!" she cried out, but nothing more.

It didn't take long until I was touching her ass and my balls were pressed up against her. Once more I started to gently stroke her ass cheeks.

"Good girl! I'm all the way in. Now pant one more time and really relax, then I'm going to start to stroke" I said.

Again she did what I told her.

I gave her a minute to adjust and then moved to the next phase.

"Here we go baby, keep relaxed!" I advised her.

I started to pump. Very slow, short strokes at first, but with almost every one I increased the length and speed a small degree. It wasn't long before I had worked up to a pretty good pace and stroking about half of my cock in and out of her ass on each stroke. I intended to maintain at that level, though I was going balls deep on every stroke.

She was groaning and grunting unintelligibly, but was obviously in pain. She was taking it however. We were almost there.

I was quickly approaching my release. I bent over her a little more so I could reach her clit. Griping it with my thumb and forefinger, I started to stroke it like it was a miniature cock.

A very different moan was added to her vocalizations. In spite of everything else I could feel her juices start to flow again and she was reacting to my hand.

At last I couldn't take anymore. The fact that I possessed this slut now, was clear. Between her stretched tunnel squeezing my cock so tightly and the fact that she was getting her ass reamed for the first time, and by the biggest cock she'd ever seen, yet was still getting turned on was such a mental orgasm that the physical one just couldn't hold off.

I felt my balls tighten and then it happened. My cock started to spasm and spew shot after shot of spunk deep inside her. It took all my concentration not to slam in and out deep and hard, but rather maintain the pace I had been.

I kept working on her clit and once my own spasms had stopped and while leaving my cock buried all the way up her ass, increased the assault on her cunt. It didn't take long before the combination of reduced pain from the lack of stoking and my slowly deflating cock reducing the stretch of her insides, plus what I was doing to her sex had her cumming violently.

She screamed out and her whole body convulsed, even though secured as she was she couldn't really move. She came and came and came as she screamed non-stop for God knows how long.

Once she was spent, I felt her body just sag over the horse as if all her bones had just been removed. Quickly I slid my cock from her ass and removed the nipple clamps. That caused a jerk and a different scream as the pain of the blood rushing back into her very tender nubs hit. With equal speed I undid all the restraints before her muscles knotted up.

One more time I scooped her up in my arms and carried her to the bedroom. I set her on the bed and tossed a blanket over her. She was covered in sweat and her hair was plastered to her forehead. I gently brushed it aside and just looked at her gorgeous face.

I left her mewing softly as I went to the bathroom to clean up a bit myself.

I pulled my sweats back on and went out to the living room after getting myself another cup of coffee and collecting the sports section from the morning paper. I sat back waiting to see what the aftermath of last 12 or so hours would be. It was hard to realize it HAD been little more than 12 hours since I first laid eyes on her.

It was over an hour before she appeared again. This time she wasn't wearing anything at all. The sight of her body caused a stir in me, even after all the things that had transpired. I set the paper and my cup aside as she approached me in silence. Without a word she sat in my lap, wrapped her arms around my neck and laid her head on my shoulder.

We just sat like that, holding each other for several minutes.

Finally I spoke, "You okay?"

There was no reply at first, then finally, "I'm not really sure."

Sitting up, she looked at me and simply asked, "Can I go take a shower?"

"Sure. There's shampoo, and everything else you should need in the cabinet over the toilet. You go get in and I'll bring in a fresh towel and set it on the seat" I said evenly.

Without further comment, she got up and headed to the bathroom. I sensed we were okay, but evidently that was still somewhat up in the air.

I gave her a minute and then fetched the towel. I also scrounged up some old cutoff sweatpants and a badly shrunken tee shirt. They'd both be way to big still but thought they might work. I laid them and a pair of tube socks on the bed.

I went in to the bathroom and put the towel on the toilet. With the steam and the frosted glass I could only see a sort of shadow form in the shower, still the word nymph came to mind. That and the word slut!

"Here's your towel. I put some old clothes on the bed that might work a little better than your costume" I called over the shower door.

No response.

I left her to her shower and went to the guest room to take a quick shower myself. I grabbed a quick shave too and went back to the bedroom. I could still hear her shower running. I pulled on some jeans and a sweatshirt and laced up a pair of running shoes. I went back to the paper.

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