Size Queen MILF Ch. 05: Other Hole

With that I opened my bag and pulled out the lube and the enema kit. From her bag Sherrie pulled out what I now know were butt plugs. She had a series of them, from the size of my ex's dick up to one that dwarfed any cock I had touched so far. And then she pulled out a black dildo that had to be more than a foot long! "No way!" I shouted.

"Relax," she said, "that's for me. I need some stretching and you might as well watch. I've started to like doing things like this in front of other people. It's like sharing a dirty secret makes it even dirtier – I can't explain it. Anyway, up to your bedroom. Is Robin going to be home today?"

Robin is my youngest daughter. She's also my Mistress and I will do anything she wants, to and with anyone she wants. I know it's weird but I really don't care. All I know is that my sex life has taken over and there's more I want to experience.

We got naked – she has a gorgeous figure and luscious boobs, to say nothing of a hairless cunt. I'm less endowed, but I have less body fat due to the exercising I've been doing all these years. My ass is my best feature, rounded and muscular at the same time. What I also had was a rather unruly, hairy pussy.

"Time to trim that bush, my friend. Get in the tub." She pulled an electric razor from her bag. "Lie back and spread those lovely legs. You probably want to schedule a full waxing to get it all, but for now let's just shave you close. It won't hurt but it may tickle."

With that she went to work as if she were a professional barber. First she trimmed every thing short, then went back over her work with the rotary razor until my pussy was as bald as when I was giving birth. Along the way her fingers also managed to caress my lips and even slip into my pussy, which, of course, was soaking wet. Like I said, I was beginning to think I was going to wind up permanently wet and aroused – not that I was complaining.

"You take lessons? The nurses in the hospital did that three times and it was never as enjoyable. You can do me any time!" We laughed.

"Now turn over and get up doggy style, then grab your ass cheeks and pull them apart. Gotta check for hair there as well!" That, fortunately, was a simple, quick visual. "Okay, you've had enemas before. We're going to fill you up and flush you out twice – it's the only way to be sure you are clean. You won't always have the opportunity but take it if you can – there's nothing worse than a guy pulling out of your ass, his cock covered with both his cum and your shit. Especially if they are porn addicts who think that ass-to-mouth is something you must do."

From the strength of her reaction, it appeared as if that had happened to her. I didn't ask. But we then went through the procedure twice. I was beginning to get aroused as she greased up the tube and inserted it each time. Instead of dreading it, I was now just concentrating on feeling it. It was different. Unusual.

Finally, I was empty and clean and we moved back to the bedroom. "On your bed, on your stomach" she commanded. "Now up on your knees and keep your head on the pillow. We're going to start with the small butt plug and once it's in we'll leave it there for a bit." I could hear the sounds of lube being smeared on it, and then felt a cold wet sensation in my ass crack as she poured it. "Go ahead and work it into your ass hole" she told me.

"Me? You mean you aren't going to help me?" I tried to sound helpless but burst out laughing.

"Alana, when we get big, I'll help. This is nothing! Now lube that hole! Work it in. Get that lube all around it, and then spread your cheeks." I obeyed. And waited. And waited?

"What are you waiting for?" I asked.

"I was just cleaning off my hands to take pictures. Open wide!" I pulled and let my asshole fall open. And just like that, I felt something large fill it!

"Push as if you were taking a shit" Sherrie said. As I did, I felt it begin to go in.

"It's going to hurt for little bit until it gets in – but that will pass and then we'll let it sit."

She was right. There as a moment of sharp pain, then a pop, then suddenly my ass was stuffed full of something big and hard. I began to breath deeply in and out, and the pain began to diminish.

"Just leave it alone. Turn over, sit back and get comfortable. I'm going to show off!" I did as she said, and saw her mount that 12" dildo on something like a plate so it was sticking straight up. I was looking at it, wondering about it, when she stood up on my bed, spread her legs to either side of it and began to lower her hips. Her cunt was glistening with lubricant and she got the head of that pole centered on her cunt and began to bear down. I watched in amazement has her outer lips parted and that baseball size cock head began to enter her tunnel. Her lips were stretched tight and thin, and she was breathing very hard. Sherrie continued to lower herself, and more and more of that plastic phallus was inside her. The look on her face was amazing – she seemed to be in pain, out of breath, struggling, and I wondered if it was worth it. Then she looked directly at me.

"I.Am.Going.To.Take.It.All." She said. "I feel like I'm being split in two and it's amazing. Having you watch me is even more amazing. This is what it's like when you get hooked on big cocks – you want bigger and bigger! This is hitting places no one has hit yet." By now she had 9 inches in her; she was now on her knees, bouncing up and down and working more and more up her cunt. Two inches to go, Then one. Then her pussy was flat on the bed and that monstrosity way way up inside her – I could see the outline of it bulging from her belly. She let out a shriek – of joy? Excitement? I couldn't tell, but there was an amazing expression plastered on her face. Her hips were twitching. It appeared to be an exquisite agony.

I move closer and stuck my tongue into her mouth, grabbing her and pulling her into me. "You're amazing, Sherrie. Now I'm going to hold you up and let you concentrate on feeling that monster inside you, and I'm going to have it be a mind blowing time." With that my hands began to pull at her nipples, twisting and pinching them to stimulate the nerves there. I move behind her and grabbed those lovely boobs, and began to work my tongue down her back. To the top of her ass crack. Then down into it to the little rosebud there. I worked my tongue around it and then into it, sucking her asshole as her big dildo filled her cunt. Then she started to cum. It was amazing to watch! Amazing to hear. It was as if she was having a seizure and her nerves were short circuiting. Eventually I lay her down on her side and that big plastic dick began to emerge. She fell onto her back, her legs spread, her cunt gaping open, and tears were streaming down her face. Within a few moments she was asleep, so I cleaned up a bit. As in I licked her juices off that dildo. I took a wash rag and cleaned her pussy.

Then I went back to work on what we were originally there for. I removed the small butt plug – which I had actually forgotten was there in the heat of watching Sherrie – and skipped over the medium sized one to something that came closer to the size of my two big cocked lovers. At it's widest it was thicker than either of their cocks. It was as long as either of them, though. I located the lube and filled my ass with more as I rubbed the toy. Then I lay on my back, lifted up my legs and positioned it at my hole and pressed. It moved in fine and I figured I had mastered it – until suddenly I felt like someone was ramming a telephone pole up into me. And it was me! I stopped for a minute, backed off and figured I only had 3 inches left – I would just have to find a way to let it in.

So, more lube, and then I went back at it. I hadn't paid attention, but Sherrie was now watching, propped up with one hand under her chin, her legs still not closed. But her hand was busy with her pussy while she watched. We were becoming really close, she and I! In any event, my hips were thrust toward the ceiling, my arms were over the back of my legs, and I was ready to impale myself. I remembered her advice: "bear down like you were taking a shit" and did, and with an explosion of pain and light the plug was stuffed up my ass. I looked over at Sherrie. "You inspired me to go big! This is getting to be too much fun! Oh my god, now I know what a thanksgiving turkey feels like!"

We grinned at each other and then we both came.

[More to come]