The Party Ch. 11

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Annie's blackmail continues as she is used and abused.
3.7k words
4.35
25.5k
9

Part 11 of the 11 part series

Updated 10/24/2022
Created 11/13/2012
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All participants in this chapter are over the age of eighteen. You might want to read the prior chapters so that this one will have a proper context. It's been a long process, but one I've enjoyed writing.

Annie was gone for only a short while, maybe as long as ten minutes, but no longer. In her absence, the three remaining boys talked among themselves and generally ignored me.

I asked Ian if they were finished abusing my wife and he looked at his friends as if to confirm their mindset but he didn't answer me.

At about that same time, Annie, wrapped in a large, white, terrycloth bath towel emerged from the bathroom, having taken a quick shower and applied a bit of fresh makeup.

She asked, "Are we done with the blackmail, yet?"

Ian stood naked in front of Annie, still sporting a semi-hard cock that he seemed to be very proud of, and spoke directly to her even though I had asked the question a few moments before.

"We're not quite done yet. We think you're good for one more go- around and we want to take advantage of this situation while we can. Since we've already each cum at least once, we'll be easy on you. Even though it'll probably take each of us a bit longer to cum the next time, there are only the three of us, now, and we feel you're up to the task. Besides, we feel we've earned the right to have a little more fun at your expense because of your lousy husband's bad behavior."

He ogled Annie up and down, not hiding his excitement at being in control, and continued, "Why are you being so modest? It's not like we haven't seen everything already. Drop the towel and get back on the bed."

Annie grinned and replied, "That's ok by me, Ian. I'm just getting started. I think it'll be fun to see if I can match the energy you little boys can muster in the next round. I'm game if you are."

Annie has always liked a challenge but I was still amazed at her flippant response. Then I looked at Annie's face and realized she meant every crazy word she had just uttered and was looking forward to the next rounds as much as she had dreaded the first.

She had, it seemed, caught a second wind while in the shower and I thought, even more significantly, she also had internalized that these boys meant her no real harm so why not enjoy the opportunity to experiment and experience all that they could bring. I also thought she liked the fact that the other three had left so that she could concentrate her efforts on just the remaining young men.

Without any more prodding, Annie proudly dropped the towel, strutted back to the bed and lay on it, spreading her legs widely and raising her knees.

"Does anyone see anything they'd like to play with?" Annie teased.

The shorter boy with the very dark penis, without saying a word, made his way back toward the head of the bed and unceremoniously placed his huge cock back against Annie's lips. As he started working his cock in and out, the chiseled boy crawled behind Annie and slipped his cock into her dripping pussy. With a grunt, he shoved that monster all the way in without expending a great deal of effort and without apparent harm to Annie's tender parts.

Annie adjusted her position so that she was lying on her side, facing me, and the boy behind her raised himself up just a bit, spooning almost and looking directly at me, as he continued to fuck my wife from behind with his prodigious black man-meat.

Annie later told me that his cock was so thick that it took both of her hands to hold it in the proper position as she guided him carefully into her belly.

"Shit, it's HUGE!" she gasped, echoing the initial words that had come out of her mouth when she had first seen that boy's sexual apparatus.

"Christ, you're going to tear me apart with that thing!" Annie cried, repeating the rest of the words she had spoken when she first saw his monster cock.

She looked over her shoulder and into his eyes, with a mixture of appreciation and reverence, then back at mine.

As his cock continued to batter her tight cunt, though I could sense that it hurt her a bit, she didn't once appear to want him to slow down or ease up with his thrusting.

She later told me that, though it had initially hurt as she stretched to accommodate his girth, he soon felt so good in her tummy that stopping him was never even an afterthought! She hadn't ever experienced anything that big inside her, previously, and she said it was an amazing experience!

As his cock continued to stuff her insides from the rear, the pain and pleasure seemed to become incredibly, intensely mixed, to the extent that his fucking appeared to occupy her entire universe, so much so that she seemed to nearly forget the boy at her face, sucking him only as an afterthought.

Continuing to encourage the boy behind her, I heard Annie yell, "Oh God, yes! Give me that monster! Ah...!"

As his huge penis pushed all the way inside, finally reaching the very limits of her vagina and expanding her walls as nothing ever had before, she mumbled and moaned and I thought I heard her say, "So biiig..!"

Not a word she said for the next few minutes was more coherent than that and it actually appeared she could pass out if she would let herself.

"Fuck, you're tight, Lady," the chiseled boy groaned but he continued to pound her pussy relentlessly, saying, "You like my big cock, don't you? You need it, don't you?"

"Oh, yes!" my wife readily agreed, "I need to have it, always!"

She had forgotten the two other horny boys and her husband were all still within hearing distance as she continued in her coital reverie with the boy behind her! In fact, for the moment, it appeared nothing mattered to Annie that was not directly related to the unbelievable feelings the thrusting lad was creating deep inside her.

"I need it so badly!"

Though his penis was long, nearly twice as long as mine, with heavy, thick, distended veins, I was still amazed by Annie's sudden abandon. She had always assured me that she was not a "size queen" and that mine was more than adequate.

Her mantra had always been: "It's not the size of the penis, but how you use it that matters."

Her reaction to this boy's equipment pushing against her opened womb opened my reluctant eyes to a far different reality.

As I watched Annie being pleasured by the two boys, I lost all sense of time. The chiseled boy continued to drive Annie from one mind numbing orgasm to the next. Her mind seemed totally out of control, yet their bodies appeared to be completely in sync: He tugged and twisted her nipples, rammed, pulled, pushed, and shoved himself into her body as if she were a sex doll, inflated for only his personal use.

While all of this was transpiring, Ian sat across from me in the desk chair and quietly watched. Once in a while, I would glance in his direction. While he had a continuous smile, he also seemed rapt by Annie's ravishment.

Without even being aware of it, the two men using her established a symbiotic rhythm; the chiseled boy would thrust far up into her pussy, pushing her mouth onto the shorter boy's hard, dark cock, which would, in turn, thrust back, forcing her even further down onto that magnificent dick in her sopping pussy. Stuck, and I mean, literally stuck in the middle, my Annie was in her own sexual nirvana as two huge cocks pleasured her, one on each end, bringing her gratification that was immeasurable.

About the time Annie had professed her eternal need for the chiseled boy's penis, the one fucking her face, who had nearly been forgotten during Annie's throes of coital pleasure, moaned loudly as he came in Annie's mouth.

Wanting to be certain that she didn't waste any of his precious gifts, he grabbed my wife by the back of the head and held her tightly against his twitching cock until he had completely emptied another load down her throat. When he was through cumming, he eased his penis from between her lips and then insisted that she lick the glans to get every drop of cum from his shrinking member.

Annie's only comment to this rude treatment was, "Mmmmm". "Mm! Mmmm!"

As she concentrated on ministering to the shorter boy, she also moaned loudly every time the monster in her pussy made it all the way into her hidden depths, places that I could never even dream of touching inside her.

As I listened to Annie's babbling while she served two masters, I began to think the vocabulary she had learned in her formative collegiate years, was lost in the moment. She was talking in such a naughty manner and I loved both hearing and watching her when she was kinky and dirty like this. I also knew she loved being in her present circumstance, social graces be damned, and stretching the boundaries of propriety. Being bad was something at which my Annie clearly excelled. Even then, she had one more surprise for me.

After Annie had finished cleaning the shorter boy's penis to his liking, the chiseled boy slowed his pace at her request. He looked as if he might need a bit of rest, too, but that was not her plan.

While Annie and the boy behind her stayed connected at the hip, Annie sought Ian's attention and waved him over to her. As he approached her, she reached out to him and grasped his erect penis, pulling him close to her so she could whisper quietly.

I thought she was going to ask Ian to embarrass me further by making me perform cleanup cunnilingus as I had before, but I was very wrong.

With something approaching reverence, as they quietly spoke, she held Ian's throbbing monster in her little hand. She was barely able to reach around its vast thickness and his girth was a real plus for her. With her fingers tightly squeezing his mighty dick, she began stroking him up and down, almost as if her hand had a will of its own. It was obvious to me that she was very, very turned on by Ian.

They whispered for a bit, quietly enough for me not to understand their conversation. She later told me it consisted simply of her asking:

"Ian, I think I want to experience anal sex. Would you please do me the honor of taking my anal cherry?"

And Ian's asking in reply, "Are you sure, Annie? You told me that anal was strictly off limits."

Annie replied, "It's time I try it. If I don't like it I won't do it again and I want to do it with someone who's done it before. You have experience, don't you? I would never want someone do it, at least the first time, who didn't have that experience."

Ian nodded his assent to both questions, looking directly into Annie's eyes.

Then Ian turned his gaze to me and asked, "Hey, man, you don't mind if your wife and try something you haven't done with her, do you?"

I knew it was a rhetorical question but I'm sure my astonishment was evident all over my shocked face. There were very few things Annie and I hadn't tried that we both had expressed an interest in trying. In fact, anal sex was the only thing I could think of, at the moment, that we had taken off the table early on and just not brought up again.

Annie had always told me, when I had broached the subject, that anal play was a real turn off for her. She feared the pain; she thought it was dirty; she wondered why men always seemed to want to invade that space. And now...as I watched...it was obvious that she had asked this stranger to take her in that most intimate and accepting manner. I didn't know what to think about this inexplicable turn of events.

I sat quietly for a moment, then answered, "I just want her safe and happy, Ian. Other than that I have no say in the matter. It's between the two of you."

Ian didn't need that kind of invitation and/or permission twice and he wasn't the kind of boy to hesitate when he knew he was in for a special treat. He wasted no time in climbing on the bed and aligning himself behind Annie. He eagerly knelt behind her, between her legs and spread her ass-cheeks. He opened a tube of lubricant that had mysteriously been sitting on the bedside table.

I tried to read the label. The stuff was called Anal Eez, or something like that.

He slicked himself liberally and then squirted plenty of the goo onto Annie's anal cleft, spreading the gel around her bottom hole, gleefully, and even gently inserting his finger into her anus in order to spread a bit of it inside her.

As I adjusted my position to better view these kinky acts, Annie raised herself to her hands and knees to better offer her anal opening to Ian. She asked the boy who had been behind her to re-position himself so that she could ride him, cowgirl style. He complied, lying prone on his back with his massive manhood pointing straight at the ceiling. Again, I marveled at Annie's optimism regarding her very capacity to accommodate the two of them simultaneously. This would be something to see, for sure.

Once Annie was comfortable with her position "in the saddle", Ian parted her cheeks and slowly pressed his bulbous head against her anus. I saw her begin to give, to take Ian's penis inside her, as he slowly slid his thick black stick up her slippery, wet, virginal, bottom hole.

She later said, "When Ian began to rape me anally, it did hurt at first; no, it burned actually. I had heard from a few of my girlfriends that it would burn like that at the beginning. I also thought I might have made a real mistake asking Ian to help me that first time since he has such a large penis to insert into that small, untested place. On the other hand, I really wanted to try anal at least once in my lifetime; thought Ian would have probably had some prior experience at doing it (which he had acknowledged), and so I thought it was worth the short duration of pain in order to have the adventure."

"That being said, the second cock, upon which I was impaled, was stuffing my pussy already; Ian's entry into my bowels made me feel as if I had four feet of cock in me, instead of close to two."

Then with a grin, she continued, "For a moment there, just before Ian started to enter me from behind, I wished the third boy had not just come in my mouth a few minutes before so that he could shove his thick, fat cock back into my face and I could experience them all fucking me silly at the same time; I wanted to be a "three-hole-slut."

That was my Annie, always bending the rules and always seeking her limits. I watched silently as Ian pushed slowly but forcefully into Annie's rear passage. He was only partly in when he started a slow, rhythmic motion, causing her to slide sideways against the prone boy's shaft.

"Fuck!" Annie cried loudly, in both pain and pleasure, as the long, black cock slowly but unstoppably worked its way up her tight ass, "That is so FUCKING big!"

It was not like my conservative wife to commonly use such language. Then I thought about what she was doing and with whom. None of this was common to Annie. I brought myself back to the hotel room and continued to watch silently as Ian accelerated his assault upon Annie's anal passage.

Somewhere in this time, having seemingly read Annie's mind, the shorter boy, whom all of us had thought was finished for the day, stepped toward Annie's head and indicated that she should take him back into her rima oris, once more.

I couldn't believe the smile that covered her face almost instantly.

The threesome soon found a co-operative rhythm, once more, this time driven by Ian's penetration of her ass from behind. His thrusts made her gyrations against the boy, whose huge penis was abusing her pussy, more horizontal than vertical but also pushed her mouth further onto the cock in front of her. Ian controlled the pace of this invasion by grabbing and holding Annie firmly by the hips, squeezing her ass-cheeks tightly, using the leverage he created from behind her to direct her movements to his liking and the delight of the other two boys. Annie groaned and squealed as her anus gradually stretched so that she could accommodate his large penis almost comfortably.

While Ian continued to explore her delightful rear-end, the boy below maintained his pace in and out of Annie's pussy, periodically telling her how tight she was, especially as he could feel Ian through the thin wall between her ass and pussy! The lad in front of her just moaned.

In, and out, back and forth, twisting, and rotating their hips as they ground and shoved their black peckers into my sweet wife for what seemed hours but really only lasted about twenty minutes.

She explained to me later, "The feelings inside me were nearly indescribable: the intensity of the pulsing, massive cock in my vagina was exponentially heightened by the pressure exerted from Ian's stuffing my ass. The cock in my throat was really just an afterthought. I didn't have to do or think anything at all; I just let them take me, use me, fuck me, and I got closer and closer to my own nirvana. I was on my way to heaven if I weren't already there."

As Ian's climax neared, he increased the pace and the power of his thrusts, making Annie ride the cock under her even more vigorously, and obviously bringing both of his cooperating partners closer to their own release.

I thought, by the color on her chest and the guttural sounds emanating from her, that Annie was cumming again; the boy below continuously moaned and also made animalistic sounds as he reached up to maul Annie's breasts, pinching, twisting and squeezing her taut nipples even more vigorously.

She screamed, "Oh, God, that feels good on my tits."

I was overtaken by the sheer sexual athleticism of what I was witnessing. It was the most sensual thing I had ever seen and my Annie was the star. I realized that the most exciting picture of all, to me, was the sight of Ian, kneeling behind Annie, firmly ensconced between her thighs, his dark skin so in contrast to her firm, pale bottom, as he thrust passionately into her depths again and again, relishing his role in her anal deflowering. No less exciting was the manner in which she eagerly accepted his exploration of her sacred depths.

And then it was in my face. The intense, burning pleasure from her pussy, mouth, ass and tits suddenly exploded inside Annie, her entire body shook in the most powerful orgasm I had ever witnessed. She came in waves of pure bliss which appeared to wash over my wife as she cried out in pleasure and then virtually collapsed onto the boy beneath her, pressing her magnificent tits against his chiseled chest and pulling the boy in front of her from her mouth.

Her release drove Ian and the boy beneath her over the edge as the three of them rode together to a massive mutual climax: It appeared to me that Annie had cum first and the men followed soon after her.

Annie just kept climaxing and climaxing.

She later told me, "First, I felt Ian spurt into my backside, actually; it felt like a hot jet of semen shot deep into my bowels as I continued riding the biggest cock of my life. I was cumming, too, and couldn't tell if mine were lots of smaller orgasms, or one great tsunami, going on and on."

"Then I felt the boy in my pussy erupt inside me, filling me to dripping with his copious seminal discharge, and for a few moments we were all climaxing at the same time. I couldn't hold myself up any longer and the shorter boy's cock fell from my mouth. Then Ian collapsed on top of me, and his squirts ebbed. Finally my own orgasms wound down too, but as we all lay exhausted, little aftershocks still rippled through my vagina and clit."

I knew Annie was going be sore all over now that the blackmail was finally paid and I wondered if she would still think it had all been worthwhile when she relived it over the next few days. She had had the workout of a lifetime and so had her antagonists.

I heard Ian say to Annie, "Now you're a 'three-hole-slut'," as he grinned in satisfaction. I knew that was what my wife was to him. He and his friends had used all of her orifices, over and over, for their communal pleasure. I also could tell his words thrilled my wife.

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