Chapter 53

“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!”