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Chapter 53

(MF, Mf, FF, ff, Ff, mult, cons, reluc, slave, humor, cheat, inc, mother, fath, dau,
  D/S, Mdom, span, lght, humil, group, orgy, harem, poly, WC, WM, WF, oral, exhib, toys, BBR, slow)

Written by Spacer X (paul_t_22@yahoo.com)

"What?!" I exclaimed after I sat up. "Did you say you want me to fuck your ass?!"

Cindy replied calmly, "I did."

It was her steady composure that did me in. Now that she'd asked, she wasn't jittery any more. But I sure was! I sat there in the tent staring at her in disbelief.

After seeing I wasn't saying anything, she explained, "Of course, it's up to you. We don't have to do it if you don't want to. But I was just thinking... this is my special initiation night. This is one of the greatest days of my life, and already a memory I'll treasure forever. I am literally giving myself to you. What better way to symbolize that and cap off a perfect ceremony than by giving my ass to you too?"

I nodded, but I still just sat there and stared. I didn't know what to think.

Finally, she asked, "What?"

"Sorry, it's just that this took me by surprise. With everything else going on, anal sex hasn't even been on my radar screen lately. You know I've never done it before, not even with Mindy."

She nodded. "Of course. But you also know that I have. In fact, I'm the only one of your women to have ANY experience with anal. I know you've had an aversion to it, but given that you're a master of your own harem and you're going to be having sex with two of your daughters, isn't it kind of odd not to at least give anal sex a try?"

I sighed. "Definitely. Mindy and I were talking about doing it for a long time, even before her cucquean craziness started. I was the one dragging my feet. I'd love to do it with you, but... it would be weird not to do it with her the first time. Even after all these latest developments, she still is my wife and soul mate."

Cindy sat down next to me and put a hand on my arm. "Don't worry. I've talked to her about that. We agreed that if she waited for you, she'd be waiting forever. Let's face it: you don't have a clue how to do it, and if you do it wrong, you could really hurt someone. That's especially true given the unusually thick and long size of your..." - she glanced significantly towards my hips - "...cock. But once you and I do it, you'll see how great it can be, and then you can try it out with her and your other slaves. I'm sure they'll all love it too, and we'll have even more great times together."

It makes sense. She's right that Min and I need help on this. We're like the blind leading the blind. Anal sex is difficult, especially with my size. If I do it wrong, I could seriously hurt someone. For my first time, it really needs to be with Cindy, since she knows the ropes. Besides, things have changed. Mindy wants it this way! She was told the plan; that's why she left, so Cin wouldn't feel weird doing it with her watching. I need to pull up my "big boy pants" and get this done. After I've done it once, I'm sure it'll get a lot easier.

I nodded my agreement. But I still felt uneasy and blindsided. I didn't feel ready.

She smiled widely, yet still with a hint of nervousness. "Great! I promise you, you won't regret it. You know, it won't exactly be easy for me either. Sure, I've had anal sex before, but not with anything like your baseball bat of a cock. But we'll work together and overcome all obstacles, even the very thick and long ones." She grinned at that.

I asked, "What if... what if I'm just too big? I've seen the way you and the others cry tears of struggle most any time you have my dick in your mouth or your pussy. Only Mindy is immune, since she's had so many years to adjust to my size."

"Yes, but we LOVE that! Like I was telling you earlier, I let my tears flow freely because it adds to the whole experience."

"Okay, but still, size is size. If I'm just barely able to fit into your mouth or pussy... we all know that asses are notoriously tight. What if I simply can't get it in? Or I can, but it causes you too much pain?!"

She took my hand. "Don't worry; I'm prepared. For the last week, I've been wearing progressively bigger butt plugs when you're not around, mostly at night. I had an enema in the time I disappeared shortly after Nicky called this evening, so I'm as clean back there as I can possibly be. And after the massive orgasms you gave me tonight, my body is about as loose and limp as it'll ever get. I have full trust and confidence in you, and that's absolutely crucial when it comes to anal sex, to prevent the woman from tensing up. So I'm about as ready as I'll ever be. The real question is… are you ready?"

I complained, "But still! I could just be too big!"

"Not true. I've fitted in jumbo butt plugs that are just as thick as you are, to test if it's possible. It is. Furthermore, in the past, I had a dildo that was exactly the same size as your cock, and that fit in my ass too. Now, we may find that it's not pleasurable enough for me to make up for the pain. But I'm determined to try it at least once. Based on all my other sex with you, I'm confident it's going to be simply amaaaaazing, for both of us! So I'm ready and determined. Again, are YOU ready?"

I pondered that. She's right. It probably WILL be great. But we won't know until we try. The burden of the difficulty and pain falls much more on her. If she's ready and willing, then how can I say no?

I said, "I am. Sure. What the hell? As you pointed out, given everything else that's happened to me, why the hell not? I have full trust and confidence in you too. If you think this is something we'll both enjoy, then I'm game. My only concern is: where's Mindy? I think it would be good if she could at least watch. I know she'd love to 'bask' in her weird cucquean way, but more importantly, she would learn so I could do it with her soon too. Actually, it would be nice if the others could watch and learn too."

Cindy looked down and frowned. "Um... yeah... about that... The problem is, I'm very shy about having anal sex in front of someone else. That may seem hard for you to believe, since I've been having sex in front of and with your other women so often lately. But I was shy about that at first too. It's just I was swept up in such a whirlwind that my resistance was shattered before I even knew what was happening, thanks to things like the 'share the cock' rule."

I pointed out, "Boy, tonight one would have never known. You were a shamelessly slutty slave right in front of everybody!" I smiled encouragingly.

She smiled back. "I know. I can scarcely believe it myself. That's what you do to me, how thrilled you make me. I'm totally in love with you and in lust with you. I was beaming with joy being such a 'slutty slave.' Already tonight has been a memory to treasure for the rest of my life, and I can't wait to be shamelessly slutty for you in countless harem orgies to come! Whenever I get self-conscious about the others, I just think about my two favorite rules: 'pleasure the cock' and 'share the cock.'"

She went on, "That said, anal sex is different. This isn't something where you just stick it in and start thrusting. The attitude of the woman on the receiving end is crucial. If I get tensed up, my ass will tense up too and you simply won't be able to fit your big cock in. Even if you do, I'll have trouble enjoying it. And nothing would make me tense up more than having someone watch! I'd feel like I'm being judged, if that makes any sense. Anal sex is a very private and intensely intimate act, at least for me."

She further explained, "That's why, a few minutes ago, I took Mindy aside and privately explained to her what I wanted to do and asked if she could go back to the house with the others. She was disappointed, but I've talked to her about my issues with anal sex, so she understood. She's a real sweetheart."

I said, "Then you'll be glad to hear what I whispered to Sue Ellen just before she left. I was concerned that the Gruesome Twosome in particular would try and sneak back here to see what we were doing, because why not? It seems that if they're not actually having sex with me, there's nothing they enjoy more than spying on me having sex with someone else. So I asked Sue Ellen if she could make sure the others stayed in the house. That includes Mindy, because frankly I wouldn't put it past her to spy on me too! But with my loyal Cupcake on the case, you can rest assured our privacy is going to stay private."

She squeezed my hand. "Thanks for thinking of that. You're right. We're in good hands. She's a remarkable young woman and an inspiration to the rest of us on how a cock slave should behave."

I nodded.

Cindy gave me a look like she was raring to get started already.

But I certainly wasn't. I was tired from all the great but physically exhausting sex all evening, and my penis was still flaccid. Plus, I'm notoriously slow to adjust to change, and this hit me out of the blue. I also wanted to find out more.

So I laid back down on some pillows, and asked her, "You and I haven't really talked much about... this. I hate to admit it, but I still tend to think of you as the Suzy Suburban Soccer Mom type. Tonight was another nail in THAT particular coffin though! I don't think I'll ever forget the sight of your stretched, naked body, with your hands reaching up to the sky, silhouetted with the stars off in the distance. You were the personification of erotic bliss!"

Cindy smiled in fond memory. "Yeah. That was pretty great, wasn't it? I can't say how I looked, but I know how I felt, and I WAS the personification of erotic bliss! I never enjoyed sex THAT much until I met you, but if I ever came close, it was with... anal sex. It definitely lights me up in a special way. If we add 'anal sex' plus 'the usual monster orgasms Master Dan gives me'... Dear God! Have mercy! You joke about killing people with too much pleasure, but you seriously might do me in! I can't wait to find out!"

She smiled at me wolfishly. She was definitely raring to go.

I asked, "Just how practiced at it are you? Was it something you did a lot with Rex?"

She grimaced. "Please don't mention that name! Especially not tonight, on my night of nights. I want to permanently wipe that memory from my mind and imagine that I've always belonged to you and you alone."

She sighed. "But I suppose I need to at least make reference to my ex to make you understand. I discovered the pleasures of anal sex back in college. Even though I was already married and raising Ruby, I was still young and wild, and I wanted to have a good time. My hubby and I did some swinging, just to be sure that we wouldn't have any regrets later, because up till that point we'd only had sex with each other."

I was surprised. "You really did that? Actual swinging?! I never knew."

"Yeah, well, it's not something I was exactly keen to confess to people. But I'm not going to keep any secrets from you. During that time, I had anal sex with a number of other men, with his permission. I found out from those experiences that you need the right partner and all the stars have to align just so, but when they do... WOW! I'm hoping that you'll love it too, and that you'll make me your regular butt slut before long."

She looked hopefully at my penis, but it was still flaccid. She struck a more seductive pose, obviously hoping to literally get a "rise" out of me.

But she also continued in a regretful tone, "At first, anal sex with Rex, no, let's call him 'He Who Shall Not Be Named.' Anal sex with, er, Mr. Nameless was great. Actually sex was really good with him in general, at least at first. But then he started drinking and getting mean. I had to stop any kind of anal activity with him, for fear that he would seriously hurt me in one of his drunken bouts. The anus isn't really built to insert a penis into, and there's lots of things that can go VERY wrong."

"A-ha! See? I'm warning you, it just might not work with us!"

"Hush, Master. It WILL work. You have to think positive! Anyway, it's been years and years for me. But I've never forgotten how much I enjoyed it. And if we can do it tonight... Oh boy! You'll have the happiest cock slave you can possibly imagine!"

I'd been mentally resisting the idea of actually going through with this tonight, but seeing how much Cindy was looking forward to it made my resistance evaporate.

Come on, Dan, you can do this. This is still Cin's big night, her one and only initiation night. Yes, I'm tired and sexually satiated, but it'll mean a whole lot more if we can manage it tonight. The main thing is that SHE is in the right mood and has the determination. We need to strike while the iron is hot!

I started to get a little bit excited as I warmed up to the idea. My dick stiffened some, although it stayed merely half-hard.

I sat up and clapped my hands once. "Okay! Let's do this! I'm in. How do we get started?"

She chuckled. "You're really clueless about this, aren't you?"

"Pretty much. Mindy and I were planning on doing some Internet research to find out how to do it right, but we never got around to it for some reason. It might have something to do with me being, oh, just a liiiiiittle bit distracted this last week or two."

She snickered. "Just a little."

"I know it's harder to fit a penis into the back door, but how difficult can this really be? We're not talking rocket science."

She laid face down next to me. "No, we're not. But I can't emphasize how tight and difficult the insertion can be. But once you do it, that very tightness can send your pleasure soaring all the way to the moon! It shouldn't be too bad since I've been prepping myself for this with butt plugs, but then again, we do have to deal with the King. Just talking about Mr. Nameless and other things has tensed me up a little bit. I know I'm only your slave, but could you start by giving me a back massage and telling me some sweet, lovey dovey things?"

I immediately got up and sat on her thighs to position myself for a back massage. "First off, I'm not really fully on board with this whole cock slave idea. Sure, I love having sex with a submissive woman, but to me you'll always be a real flesh and blood woman with a heart and soul, not some kind of sex toy. That's just talk that gets us horny. So never let me catch you saying you're 'only my slave.' The way, I look at it, you're more like my second wife, but you're really into the whole submissive thing. If you ever decided you didn't want the slave part, I'd still love you and want you in my bed with Mindy every night."

"Aaaah! Master, you're so sweet. But I can tell you now that's never going to happen. Being your slave has become an essential part of who I am. I wouldn't want that to change no matter what!"

I nodded in understanding. "Even so, there are going to be times like this when I'll want to treat you like a queen. And since I'm your official master, I may have to resort to ordering you to let me do it!"

She giggled gaily at that. "Yes, Master! If you insist, Master, I have no choice but to fully submit to your wonderful back massage. Woe is me!" She giggled some more.

I started in massaging her back.

She purred contentedly. "Mmmm... Have I told you lately how much I love you?"

"Probably not for, oh, the last half hour or so."

She giggled some more. "Then that's too long! And Dan, this cock slave thing, it's kind of an elaborate sexy game for me, and yet I also take it very seriously. It's complicated. On one level, I know you're still just a man, you still fart and burp and all the rest, but on another level, I revel in the fact that you're so studly and impressive that you can handle a harem like ours and fuck other hotties besides! But the bottom line is that I don't just plan on becoming some kind of mindless human blow-up sex doll for you."


"Frankly, I don't think you have to worry about that with any of your women. If you haven't noticed, we're a very feisty bunch."

"That's true." I chuckled at that. To say the least!

I proceeded to give her a lengthy and deep back massage while also telling her in different ways how much I loved and cherished her. It seemed to work wonders, by the way she was blissfully purring. I don't think it was possible for her to get any more relaxed.

After a while, I scooted down her legs and the back massage turned into more of an ass massage. I had her spread her legs wider, and I spent a good amount of time pleasuring her perineum ('taint') up to her pussy lips and even sometimes her clit.

This was very arousing to me as well as her, which meant that my dick finally got fully erect again. I rubbed my cockhead against her lower ass crack, letting her know my condition.

After a while, she perked up enough to say, "I feel we're ready to start. But keep in mind this is a gradual process. If you've seen erotic stories where a guy just sticks it in like he can slide it into a pussy, they're wrong. Either that, or the woman has the loosest ass in the universe. And yes, with your size, we're going to have to be extra careful."

"Got it. I'm ready to follow your lead."

"Good. I think the next step is if you can lead the way with a finger or two. Oh, and we're going to need lube, LOTS of lube! Luckily, Mindy knew this could happen tonight. I know she left some lube near the mini-fridge."

Cindy had been so relaxed that I was surprised she could string all those coherent sentences together. But once she'd gotten that important message out, she went back to moaning and purring sexually and blissfully, even though I'd stopped massaging her.

I quickly found the lube and resumed my position behind her ass. I also found a glove next to the lube and put it on. Then I started experimenting with inserting an index finger in her ass.

This was very strange to me. Sure, I'd done a lot of anal play with Mindy over the years, but it was different knowing that my penis was supposed to go in there soon. I was raised a "good Catholic kid," and the anus was a very mysterious thing to me. Anal sex was never talked about as something wrong, because it was too taboo to mention at all. But somehow it was made clear to me that it was "icky" beyond all imagining, as well as being a serious sin.

As a result, I had to psych myself up when it came time to stick two fingers in instead of the usual one, and attempt to loosen and widen her opening some more. But that went well, and her sexy moans and purrs showed that I had to be doing something right.

The time came for me to position my cock over her anus and start to push in. I was all lubed up and ready to go. But, to be honest, I was feeling increasingly nervous. Doubt about my size fitting in her was just part of my problem. All those "icky" issues were on my mind as well.

Worse, I worried that she would sense my mood and then start to tighten up too. As a result, I wanted to get past this stage as quickly as possible.

Cindy must have sensed some of that, because she advised me, "Okay, let's start. But remember, the worst thing you can do here is rush. This is NOT going to be easy! Hopefully, once I become a regular butt slut for you, my ass will get accustomed to your size. But I haven't done this in ages, and my poor ass won't know what hit her when you start pushing in something that'll seem the size of a Greyhound bus to me. It's going to be a 'two steps forward, one step back' kind of thing. So please, take it slow and easy!"

I replied, "Okay, Cin. I may be the 'master,' but when it comes to this, you're the boss right now. Just keep in mind how good it's gonna feel, eventually. This'll be soooo worth it..."

"MMMM!" she moaned agreeably.

I started to push my cockhead in. Outwardly, I was attempting to sound confident and optimistic. But I was actually thinking, Holy fuck! This is impossible! Two fingers is about all that can fit in there, and that was a tight squeeze. How the hell am I supposed to get my entire dick in there? There's no way this can work!

But then I also thought, The human body is a remarkable thing. Think about a woman giving birth. How could an entire ten-pound baby come out through a vagina? But it happens all the time! Okay, maybe not "all the time" but often enough for it to be intentional and possible. I've just gotta be confident and persistent, and make this happen!

I kept on pushing. Unfortunately, nothing was really happening. I might as well have been pushing where there was no hole.

Cindy sensed the problem, and said, "Okay, Master, this is where the rubber hits the road. I know that we treat you like this invincible, insatiable dominant sex beast, but the truth is you're really a kind-hearted and sensitive guy most of the time. At least when King Dong isn't in the house."

We both chuckled at that, which helped relax us.

She went on, "I can tell that it hurts you emotionally as much as it hurts us physically when it comes to giving one of us a harsh spanking. You don't do it because you get off on it, but because you feel you must. I know all that, but now's the time where you've gotta stop being the nice guy and get, well, pushy. I'm not talking about a full-on King Dong rampage, but just be aggressive. I'm not made out of glass. Push it in! HARD!"

Before I could overthink it, I pushed in as hard as I could. And miracle of miracles, I could feel that I was making a little bit of progress. It wasn't much, but it was there. I exclaimed, "Hey! Did you feel that?"

"Yes, I did," Cindy grunted. "That's good! But don't stop there. I'm nice and relaxed. I don't think I have to worry about you pushing too hard because you're not that way. So keep at it, just like that. Remember, getting your bulbous cockhead and especially the edge of the crown in is the hardest part. Once we do that, the rest will follow naturally. So even a fraction of an inch is a big victory."

I kept pushing. It was difficult! This was a lot harder than I'd expected. I found myself thinking, Man! Anal sex had better be at least twice as good as regular sex, or it's just not worth all the trouble. And after all this, I've pushed in, what, an inch at best? Good grief!

But I have to do this for Cindy. Think about all the things she does for me. The way she and the other slaves treat me like a king is downright ridiculous. This means a lot to her, and it's her special night, so I've just gotta do it! I've gotta! Push, dammit! Push!

I kept at it. There were times I was ready to give up, but I didn't say anything.

Cindy, bless her soul, could sense my frustration, and she acted as a cheerleader of sorts. "Come on, Master! You're almost there; I can feel it! Just a little bit more! PUSH!"

I think I was holding out for fear of hurting her. Eventually my frustration grew to such a level that I started pushing harder and harder. And then, after one particularly forceful push... voila! The crown of my cockhead made it through! I slipped another entire inch in immediately afterwards, since my cock was narrower there.

"All right!" I cheered. "We did it!"

"We did! Good job, Master! I knew this could work, I just knew it!"

I couldn't see her face, but I could hear the sound of sobbing. My heart leapt to my throat with worry. "Are you okay?! I hear you crying!"

"I'm fine! Fine!" Then she didn't say any more, but I heard a lot more panting and sobbing.

Another minute passed. Finally, I was forced to ask, "Are you REALLY okay? Please tell me the truth. Are you in pain?"

She responded with surprising intensity. "You bet your damn ass! It fucking HURTS!" But then she added, "Don't worry! These are tears of joy AND struggle this time. I'm so happy!"

After she recovered a little bit, she added, "I worried you were just too thick and I was too tight. I was trying to put up a brave front, but you're right, I worried you might just be too big. If we didn't make it today, I thought I might have to try bigger and bigger butt plugs and wear them all the time before we could give it another go. But we made it this far! That's why I'm so overjoyed, because it means my ass can be a slave to your cock too!"

I was encouraged, but I pointed out, "We're far from done. I feel like I'm stuck."

"Don't worry. The rest will be easy as pie. You'll see!"

Unfortunately, that wasn't close to being true. The rest was far from easy. I was already sweating and wishing the heater wasn't turned up so high. After a brief rest, I had to keep on pushing. And pushing and pushing! I was doubting even more why anyone would ever bother with anal sex, period. But I was determined to do it for Cindy.

It didn't help that she continued to sob as if she'd just heard her parents had died. At one point, I insisted that she turn her head enough for me to actually see her face. Sure enough, her eyes were red and tears were streaming down her cheeks, but there was an unmistakable look of joy brightening her entire face. There even was a kind of radiant glow.

So that encouraged me that she wasn't bullshitting in order to make sure I kept going. Actually, I sensed she wasn't being entirely honest, since she didn't want me to know just how much pain she was feeling. But there was nothing I could do about that. Thanks to seeing that joyous look on her face, I resolved to keep going and cross my fingers that her pain would fade and her pleasure would soar. If it got to be too much for her, I had to count on her being honest enough to tell me when to stop.

At least my taboos about anal sex being weird and icky weren't a serious problem. I was so focused on just squeezing in all the way that I didn't have time to worry about anything else. I reduced it to a simple physical problem, like trying to cram a square peg into a round hole.

I kept on pushing and pushing and pushing! The good news was that although the progress was slow, it was continual. I could see that I was getting in deeper, bit by bit. At one point, I joked, "For probably the first time in my life, I'm wishing my dick wasn't so long!"

She laughed. "Me too!"

"Remember, if the pain gets too great, tell me!"

"Trust me, I will. I'm hanging in there. It's okay!"

I looked down at my crotch and saw that I still had about half of my eight inches to go. We'd made about an inch after my cockhead with relative ease, but then my shaft got thicker and it seemed we were stuck again.

Ugh! So far, I'm not a fan of anal sex at all. Had I tried this with Mindy for the first time, I'm sure we would have given up on it by this point, since she has a conflicted opinion on anal sex like I do. But I have to keep going for Cin. She really wants it. She's absolutely determined. I have to be determined too.

I kept telling those thoughts about determination to myself over and over, and sometimes out loud.

And Cindy kept on cheerleading, even though her loud grunting and wet face showed she was suffering. At times, she blatantly lied. She'd say things like, "We're almost there! Just another inch or two and we'll make it, I can tell!"

I found that kind of cute, since we weren't even halfway when she said it. But that strengthened my resolve to see this through, since it helped show me how much she wanted it.

At one point, I asked her, "How are you doing? Would it help if we take a break?"

"I'm doing fine. Don't take a break on my account! Just wait until you're fully in me. That's when it'll get good. Trust me."

Ugh! I am NOT having fun. This feels like a chore to me, and I hate to imagine what she's going through. Far from feeling pleasure, I feel like my dick is getting slowly crushed to pulp. But then again, everyone says anal sex is great. Surely this has to get a lot better, or people wouldn't do it. I just have to be patient. Once the thrusting starts, that's when it'll change, right?

So I kept on, with Cindy cheering me on. When I finally "bottomed out," getting as deep in her ass as I could get, I thought that would be a big victory. But I didn't feel any better. It still felt like my cock was in a vise that was squeezing in on all sides.

Cindy wasn't having an easy time of it either, to say the least. She kept telling me she was fine, but I could tell from her grunts and groans that she was anything but fine. She was sweating like a pig, clenching her fists, and grasping at the sheets. Even after I was fully sheathed in her, I could still hear her sobbing most of the time.

Finally, we reached a point where I could start making little thrusts in and out. But it STILL wasn't pleasurable to me. She was just too tight.

I thought, There's no way in hell she's enjoying this! I'm just too thick for her. What a disappointment! Anal sex is a big deal for her, and we're just not anatomically compatible. And if I don't fit her, I doubt I'll fit any of the others. I'll be afraid to try, after this.

Yet we kept at it. We took little breaks to help her body adjust to my size, then I'd thrust a little more. Then we'd rest. Then we'd give it another try.

Fiiiinally, slowly but surely, I started to make some headway. The sense of painful squeezing lessened, and I was able to thrust in and out more than just an inch or so at a time. There was no magical moment where everything changed, but the longer we went at it, the better it got.

I'd been skeptical and unhappy all along, but the time came when I had to pause my thrusting and admit, "Okay, this is starting to feel good."

NOTE: Thanks to the suggestions and corrections of IBT, Ecchi Spud, SeaDawg77, Johnny Galt, and Concerned, and the reformatting of Sam.I.am.

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