Chapter 54

“A-ha!” Cindy said triumphantly. “I told you! But hang in there. It’ll get better still. I promise! A LOT better. My ass refused to accept you at first, but you’re conquering me through sheer persistence. I’m going to loosen up some more, and then you’ll see.”

Man! What hard work! I wiped my sweaty brow and resumed thrusting.

I felt a lot better when I felt her ass tremble. Then I heard her scream with obviously lusty fervor.

Shortly thereafter, she gasped out triumphantly, “So it begins! That was my first orgasm. The first of many! This is where it really gets good!”

I couldn’t see her face and I hadn’t heard her sobbing in a while. “Are you still crying?”

“A little, I’ll be honest. But it’s mostly tears of joy now. Trust me, Master. Yes, it still hurts like hell, but the pleasure is much greater. And I know from experience that the more we do it, the better it’ll get! Please, we can’t stop now!”

Sure enough, it got better for me as she loosened up a bit more and I could thrust in and out almost as much as if I was in her pussy, but with a much tighter fit. It still didn’t seem worth all the extra work, though.

However, it was a different story with Cindy: once she had her first orgasm, it was like she couldn’t stop having them! Many more orgasms followed, one after another! It seemed her ass was quivering and spasmodically squeezing my cock more often than not.

At least I felt great that I was making her feel so good. Before long, it was like she was on a hair trigger and stayed there, so seemingly anything I did made her cum.

I’d heard somewhere or another that most women don’t cum from anal stimulation alone, so it’s good to get her pussy and clitoris involved as much as possible. With that in mind, now that the great struggle was over, I was able to focus more on using my fingers to play with her pussy and clit. Sure enough, that worked to great effect. Hell, it was like that any time I so much as thought about touching her clit, she had a big climax!

But I noticed that even when I wasn’t touching her there, she would cum anyway! I knew that some people just didn’t have many nerves in the right places to enjoy anal sex. But I was starting to realize that she had to be one of those women capable of experiencing a lot of anal pleasure. She just kept on cumming and cumming!

At one point, she said, “Oh, Master! This is divine! Please ... stop! For a minute! Gotta ... gotta rest!”

Naturally, I stopped.

Once she’d recovered her breath some, she said while we still rested, “This is what I’ve been dreaming of for so long! It’s coming true! You’re stretching my ass to fit your fucking GIGANTIC COCK! HNNNG! So fucking THICK! You’re almost too much for me, but I love it!”

After more lusty panting, she went on, “Master, you have no idea how long I’ve wanted this! So many times I’d visit Mindy and see you, and then later that night I’d masturbate in my bed. I wanted you to fuck me in every hole, so bad, but most especially my ASS! There are times I got so excited that I even put my Dando up there. But now you’re fucking me with the real thing! It’s just like I’d dreamed: your huge cock takes the whole thing to another level! Mr. Nameless couldn’t come close to what you’re doing to me!”

Hearing that made me feel good, and it gave me renewed energy. But I also thought, “Dando?!” Tell me she didn’t just say that. But she did. Oh shit! How could she have a Dando too?! The Hellions said there were only three!

Okay, I can’t worry about that right now. Gotta stay focused. I’ll make a mental note and get back to that later. But right now, I’m gonna fuck her with all my might!

I roared with renewed vigor, “Just wait, Cin. I’m just getting started. I’m gonna totally rock your world!”

“DO IT! Don’t hold back at all now! Fuck me HARD! As hard as you can! Fuck the SHIT out of me! Literally!” She giggled a little at that.

I was inspired to fuck her harder and faster. Luckily, although I’d experienced a TON of sex all evening long, I’d been fairly passive for most of it. So even though I’d climaxed three times in the last few hours, I still had a considerable amount of energy. I knew I’d be dead to the world tomorrow morning, but for now I was determined to give Cindy the best anal experience of her life!

I tried not to think about her inadvertent Dando comment, but it actually helped me. I felt angry that I’d been lied to, probably by the Gruesome Twosome, and I channeled that into more vigorous thrusting.

I figured I had to be succeeding, because she was orgasming more or less continually, as long as I kept thrusting. And when I played with her pussy or clit as well, it was like she was having orgasms on top of orgasms. I’d never seen someone so far gone into the throes of ecstasy, and that was saying a lot. Hell, I would have thought her throes of ecstasy from earlier in the evening couldn’t be topped, and yet here we were!

I was able to take longer and longer strokes, so much so that at one point I accidentally pulled too far back, and Cindy’s ass reflexively expelled my cock all the way out.

Boy, she did NOT like that! She frantically screamed, “Put it back! Put it back in! Please! Now! I beg you! I NEED your COCK in my ASS! MORE COCK!”

I was having a lot of fun by now, and I thought I’d tease her a little bit. “And just what’ll you give me if I do put it back?”

She cried out, “Don’t joke around! Please! I need it so bad!”

There was such a desperate edge to her voice that I thrust back in right away. After all the trouble we’d had getting my thickness in her the first time, I thought it would be another ordeal getting it back in. But it slid in with surprising ease. That showed to me how much her body had adjusted to my size.

Man alive! Things are getting pretty intense. It sounds like she needs my cock in her ass as much or more than she needs air to breathe! I must say, this is quite an intense trip. I’m starting to see the appeal, for sure!

When I pushed in all the way after that, her resulting orgasmic screams must have set dogs to barking throughout the whole neighborhood. I was sure that my women in the house had to be hearing her screams, despite the tent and the distance.

I actually took the time to look around our tent to check if anyone was spying on us. I realized I wouldn’t have been able to tell if there was, due to the darkness, so I focused on making Cindy cum more times than should be humanly possible in one evening. That was my goal.

I had to marvel at how much things had changed. There’s no way I could forget the long and arduous ordeal of getting my thick cock in her ass. Her ass was still tight, but in the most pleasurable way. I couldn’t have asked for a more stimulating fucking sensation.

And Cindy! Jesus fucking Christ on a pogo stick! Cindy just couldn’t get enough of my cock ramming her up the butt. It was like she was possessed or something. She was animalistic in her guttural moans and unrestrained screams.

I still was not happy at how difficult it was to reach this high plateau, but I figured it was worth it for Cindy’s sake. Clearly, she was having the time of her life! She was constantly on a hair trigger. I felt like I could make her cum simply by brushing the tip of her elbow. Everything I did made her feel great, and that made me feel great.

I’d been fucking her fast and hard for a little while, but then I thought, Why bother? At this point, it’s actually overkill. Since she’s already maxing out on big orgasms, why waste my energy? If I go slower, I’ll be able to last much, much longer.

So that’s what I did.

Cindy kept yelling for me to fuck her faster, deeper, and/or harder, but I didn’t really listen. That drove her crazy with frustration, and made her cum even MORE!

I think my “go slow” strategy was the right way to do it, because I lasted a long, long time. I don’t know how long, exactly, since there was no clock in our tent, but this was no five- or even ten-minute quickie. And it was an endless plateau of great pleasure for me, comparable to when all five of my women were working on me at once. I couldn’t imagine what Cindy was feeling, because I knew she had to be enjoying this even more than I was!

After a while, I thought with great understatement, Hey, this anal sex thing is pretty all right! And that’s the understatement of the year! No wonder she was so determined to try it out, despite all the pain. And I can see why she’d want to do this on a regular basis if fucking my cock up her ass makes her head come undone like this! Good god, is she ever going to stop cumming? Holy guacamole!

As great is it all was, I knew it could be even better once we’d have some practice and learned how our bodies reacted to each other and what worked best. I knew I could make the joy ride last even longer still.

But I decided, I’m not going to fight my urge to cum to the bitter end. For one thing, I’ve had a full day of fantastic sex, to say the least! But also, Cindy needs to be up early for her first full day of work tomorrow. We could literally do this for another hour or two, if we want to fuck until we drop dead of total exhaustion. I probably could get it up for a fifth time if I really try. Hell, we could sleep together and fuck still more in the middle of the night and when we wake up. But then how will Cindy get through the day? I’ll be totally exhausted too.

Although this is Cindy’s big initiation night, there will be many more nights to come. A countless number, really. There’s no need to overdo it. I’m already sure that her initiation has been a grand slam home run for her, and that’s what matters the most.

So I yelled, “Cin, I’m gonna cum!”

She yelled right back, “Do it! Cum in me! CUUUUUM! Give it to me! MAKE ME TAKE IT!”

I came! I felt a special satisfaction unloading my cum deep in her bowels. I can’t explain how or why, but it was a different feeling than cumming while fully sheathed in her vagina, or any vagina. I don’t know if it was better or worse, but it was different. I knew right then that it was something I wanted a lot more of!

Once I came and my dick was withdrawn from her ass, it took her a long while for her arousal levels to subside. I swear, she kept having orgasmic aftershocks even after I’d stopped touching her altogether! It was remarkable. I’d never seen anything like that before.

I held her in my arms and we rested for a while, lying side by side. I closed my eyes and fell asleep.

She did too, because when I woke up she was still sleeping. It was adorable that she had a big smile on her face, even while asleep. She looked positively radiant, despite all the sweat and tussled hair.

I decided to let her sleep. She had to be having some very happy dreams.

I felt damn good. After we’d had so much difficulty at first, I honestly hadn’t expected to enjoy the anal sex nearly enough to justify all the effort and pain involved. I’d done it for Cindy. As the saying goes, “It’s better to give than receive,” and it was nice to give something back to her after so very much that she’d done to me. That fact that in the end it was worth it for me after all was a nice, unexpected bonus. Clearly, this is something we’d have to do more of in the future.

By and by, I could sense that Cindy was stirring. Even though her eyes were still closed, I guessed she was probably awake. So I asked her, “Cin, you there? How are you doing?”

She didn’t open her eyes, but her smile grew. “Mmmm ... Never better! Aaaah...” She snuggled into me happily.

Neither of us were in any hurry, so those were the last words spoken for a few minutes. I enjoyed simply watching her contented face. I felt like the king of the world to have sexually rocked her world, just like I’d told her I would.

Then, out of the blue and with her eyes still closed, she said, “Mmmm ... Master, you’re stuck with me now!”

Sensing that she was fully awake and well rested, I asked her, “What do you mean?”

“I mean ... I would have loved and served you anyway, but with the anal sex as a kind of cherry on top, you’re going to have yourself one VERY happy camper. Er, slave.” She giggled.

“Well, that’s good news.” I lovingly ran a hand through her hair.

She purred approvingly in response to my petting. “Master, you have no idea how much I loved that, how much I NEEDED that! I feel like I’ve bonded to you even more than before. My mind is made up and you can’t change it.”

She purred sexily some more. “I’m gonna be your personal butt slut. Your number one slut in the butt!” She giggled. “It’ll get easier, you’ll see. I’m gonna keep training my ass with butt plugs so you’ll fit just right, any time. God, it’s gonna be so fucking GREAT! Even now, I can already feel the yearning to impale my ass onto your cock again growing within me. I’m so ecstatic, I could fly!”

I replied, “That’s great. And I’m pretty happy now too. But I’m not so sure if the flying is going to work. Unfortunately, I think we’re going to have to walk back to the house. And remember that you do have to be at work by nine tonight.”

“Oh no! UGH! Don’t remind me ... Ugh. I can’t do it.” She finally opened her eyes and looked at me with concern.

“What?”

“I can’t do it. Seriously, I don’t think I could stand, much less walk, and definitely not all that way. Master, I know this is asking a lot, especially coming from a slave, but could you please ... carry me?”

I pointed out, “That is asking a lot, if only because it’s a really long way, given how much you weigh!” Knowing how women can be sensitive about their weight, I quickly added, “Not that you’re overweight at all, but you weigh like an adult woman, and it’s such a long way to go!”

She said sadly, “I understand.”

I continued, “But I’ll give it a try, at least. I’m not sure I can make it. However, I don’t want to hear you say ‘this is asking a lot, especially coming from a slave.’ Yes, you’re a cock slave, but you’re also kind of a wife, as I keep telling you. I don’t want you bowing and clanking around in chains and all that.”

She giggled with delight, and made some pretend clanking noises.

“I want you to disagree with me and say I’m full of shit when I’m full of shit. I want you to be happy and well loved. Sometimes that’ll mean some kind of sexually submissive role for you that we both enjoy, but other times it’ll mean me giving you a special gift or treating you like a princess, because you deserve that. So, yeah, I’ll do my damnedest to try to carry you, even though it’s going to be an ordeal, because you deserve it!”

I could see Cindy’s face glowing with delight the more I spoke. By the time I finished, tears were leaking from her eyes. (She’d wiped her face clean after our fucking finished.) “Oh, Master! You’re too much! Just when I think I couldn’t POSSIBLY be any happier, you have to go and say that! BEST. DAY. EVER!”

She kissed me on the lips. However, she clearly was totally worn out, because she barely had the energy to do that, and it didn’t last long. The tears kept flowing though, more and more.

I wiped her cheeks. “Hey, please don’t cry. Why so much crying tonight?”

She exclaimed, “Because your cock is so very, very enormous, and your heart is bigger still!”

I smiled at that. “Even if you’re happy, if you start crying then I’m gonna start crying, and then we’ll be a bunch of crybabies.”

She giggled. “Sorry. I’ll try to stop. It’s hard though when I feel this ... MMMM! There are no words. Fantastic! Incredible! Even if it goes south from here, I have no regrets becoming your cock slave, if only for this one perfect night!”

“Well, thanks, but it’s not going to go south from here. It’ll just get better and better as our love grows over the years. Now, come on, let’s see if we can get you back to the house. If we wait around, I’ll just get sleepier. Tomorrow’s another day, and it’s going to be a rough one.”

I wasn’t just thinking about the work that we’d all have to go to. There also was the big “reckoning” speech I was planning on giving. Things would change significantly after that, at least for a while. This was probably a “last hurrah” for a while, with a very rocky road ahead.

But then something occurred to me. “Wait a minute. Before we go, I have one tiny little question. What’s this about you having a Dando?”

She didn’t seem unduly alarmed, just somewhat embarrassed. “You know what a Dando is?”

I nodded, lazily twirling a few locks of her hair around my finger. “‘Dan’ plus ‘dildo’ equals ‘Dando.’”

She groaned unhappily. “Oh God. How embarrassing! But then again, after officially enslaving myself to you tonight, and taking your huge cock down my throat and up my ass and everywhere else, who the fuck cares?! It’s not like I have any dignity left!”

She quickly glanced at me to gauge my reaction before reluctantly admitting, “Mindy gave it to me about two years ago. Ugh! It’s so embarrassing! Do you really want to know the full story?”

“Yes.”

Cindy resolutely stared up into my eyes. “Well, she’d known for a long time how I’d had a huge crush on you. And we told each other most everything, so when she told me how she’d made an exact copy of your incredibly thick and long erection, I jokingly told her how I wished I had one too. Except I joked about that a lot. And then, when my next birthday came around, you could imagine my surprise when she gave me one in private as a gag gift!”

Her eyes were opened very wide, as if she was reliving the shock. “I blew it off like a joke, but I’ll tell you, later that night it was no joke when I tried to fit the damn thing in my pussy. And then my mouth! It gave whole new meaning to the phrase ‘gag gift!’ After that, it became my favorite sex toy. Except that it was so very big that I rarely put it all the way in me. However, I loved to just suck on the tip or rub it against my clitoris and pussy lips while dreaming it was really you. Aaaah! And sliding it into my cleavage or just rubbing it against my ass crack was ... UNH! Just heavenly! I’ll tell you, that thing got a lot of use, up until I started having fun with the real McCoy instead!”

She was all smiles. “So that’s the full story. Pretty humiliating, huh? To be that into the husband of my best friend!” Something occurred to her. “By the way, how did you know I have one, and why’d you bring it up now?”