In Matters of Size, Size Matters Ch. 01

I hit reply on her message, and checked off the box that said to allow her to see my private pictures and videos. In for a penny, in for a pound, as they say. "Hi Sally. Thank you for letting me see your privates - I can't tell you how many times I came watching them! Watching you ride that big dildo was like nothing I'd ever encountered. I actually came when you did WITHOUT EVEN TOUCHING MYSELF! I don't know the right words for what might happen, but I think we ought to get together and find them. When can we meet? Love, Anne." And then I hit send, hoping for the best.

At that point I turned off the computer and went to sleep. If I recall correctly, I had my first sex dream in years that night! I had forgotten how much fun they were, although I was bit tired when I began my day. And, like the day before, I was noticing things about the people I worked with that I had previously been ignoring. People said "hello" and I said it back. People were friendly. Smiling. There were some really good-looking people. Some really hot looking people (meaning both men and women.). It was as if I was emerging from a long sleep or something. Anyway, I made it through the day without incident, and hurried back home. To say I had high hopes would be to put it mildly.

I tried to take my time eating and unwinding from my day. I didn't want to appear as if I was anxious - although I have no idea who was going to see or even care. It took forever for my laptop to start; it decided that an update was necessary and took its sweet time. I used that time to get naked and comfortable. When it finally came up, I went straight to my site and logged in. There was Sally's reply.

"Wow, Anne, I loved your videos. And when you said you came just watching mine, I was flattered and amazed. What are you doing this weekend? We must get together! Here's my number. Call me - emails are just not enough! Love, Sally." It took me a minute or so to pick up my phone and punch in the number, and even longer before I actually pressed the button to connect, but finally I did. It rang briefly and then was answered.

"I don't recognize this number, so I'm hoping this isn't some sort of insurance pitch" said the sultry female voice.

"I think I have some something even better than insurance to discuss. This is Ann. I assume it's Sally."

"You've got that right! I'm so thrilled you called me. God, I loved your videos. And it would seem that mine appealed to you as well. Did you really come from just watching? I can't believe it! I didn't think it was possible! I'm sorry if I'm babbling, but I'm just so excited that you called, especially since I've never done something like this before! What should we do? Do you want to come over now? I'm not sure that would work."

"Hold your horses, Sally. Now would definitely not work, and while I'm new at this as well, in a past life I wasn't a stranger to meeting up for sex. Here's what I'm thinking. I'd be happy to meet you for drinks somewhere near you. If we hit it off, then we can go grab a hotel room on me, or go back to your house and do whatever comes naturally. Including spending the night if it gets to that. How does that sound? Would Friday night work? I can get off work early, and I'll bring along a few changes of clothes. Then we can take whatever time we want. How does that sound?"

"It's perfect. We can get dinner and drinks and take it from there." We exchanged numbers, she gave me the address of a restaurant near her, and we were set for Friday. Then there was silence. "It looks like you have an iPhone. Can we Facetime?"

"What a great idea! Hang up - I'll call back in a minute." I made sure that my camera caught my bare shoulders as well as my head. The audacious nature of it tickled my fancy - and wet my pussy - but I started it out with some dignity and just allowed for the something more interesting. Then I called her back and wouldn't you know it? She had done the same thing except she wasn't being dignified, discrete or demure - her phone was obviously on her desk, and she was framed in it with her arms crossed and a very large set of tits draped over them, grinning ear to ear.

"Isn't technology wonderful? I LOVE the look, Sally. What I love even more is that you answered my call like that. I started to get naked before I called back, but I just didn't have the courage to start out like that. Let me adjust my camera." I managed to find a holder for the phone and pointed it at my recliner, then I sat down and spread my legs, knowing full well that the camera was now showing everything, including my very wet pussy! 'How's that?" I asked.

"Hot! Very hot. And it beats that uncertainty of meeting a blind date in a restaurant. I mean, it lacks some things (I'm a big fan of things like taste, smell, aura, feel and tasted - did I mention taste?) but it's like homemade, interactive porn, right? Tell me - are you wet right now? I'm almost dripping!" With that she pushed back from the camera until I could see hair naked pussy, glistening with her dew.

"What do you think? I AM dripping! I see why guys have a boob thing - your nipples are amazing. I want to fasten my mouth to them and suck until you come!" All the while I was busy with both hands - one rubbing my clit, and the other using three fingers to fuck myself. "Wish I had you here to work something large up into me."

"And I, in turn, wish I was there to accommodate you. I want to push you as far as you are able. I want you to feel so stretched that you can't tell where the border is between pain and pleasure. Then I want to make sure you come like never before! I can't wait for Friday! Go ahead - I want to watch as you get yourself off. I know what a dirty slut you are - just like me - and I want you to know what it feels like to be watched."

It took very little to add my pinky finger, and finally fold my thumb over. I was suddenly filled by my hand deep into my hole. I heard her voice, and tried to follow her instructions.

"Isn't it amazing? You got your whole hand inserted. You are fucking yourself with your hand, like some depraved, sex starved slut. And you love it, don't you?" I nodded.

"Good, now close your eyes. Time to take it to the next level - take out your hand." I did, relaxing for a moment.

"Now, make a fist - because you never did that before did you? You were so turned on by simply getting your whole hand in your hole that you didn't stop to think you could do more. Your fist will stretch you differently. It will make your orgasm even more explosive. Do it, slut!" The power of her command was something I needed. I followed her instructions and curled my fingers to my palm, wrapping my thumb around them, and could see it was much wider that way than my flat hand. I brought it to my outer lips and began to press.

"Use your other hand and spread those lips. Spread your legs even wider while you do it. Now press hard!"

It was as if I was stuffing a baseball bat into my pussy. I felt stretched in new ways, and in places I had yet to reach as I worked my handle slowly into myself. It was painful, but at the same time I was thrilled by the pain and the sensations it brought. I felt the pains turn into something else as I pressed deeper and deeper.

"That's right, Ann. You need to feel it burning and stretching. You are nothing but a cunt that needs to be stretched. You know you will love this, and you know that even if you get your arm up in there it eventually won't be enough, will it?" I shook my head, amazed at how she was able to understand what was going through my mind. Sweat was pouring off me as I continued to press up and in. And then, I was in as far as I could go. I looked up at the screen - Sally was grinning from ear to ear.

"You did it, Ann. All by yourself. You impaled yourself on the biggest thing you ever used, and you're both ecstatic and in pain, correct?" I nodded again, unable to speak.

"Take a moment and appreciate it. Close your eyes and just let go into that feeling of being stretched and pressed and pressured and how amazing it feels. You thought you might tear something, didn't you? But you didn't - you revealed yourself to me as a woman who wants to be filled as full as possible. Hell, I even recorded it, so not only can you make it part of your private videos, you can watch it and appreciate it as often as you want. Are you ready to come now?" I grinned at her, and nodded vigorously.

"Yes" I said through clenched teeth. "Make me come."

"Oh, you'll come but all I am going to do it talk you through it. So close your eyes and begin to open and close your hand. Feel it press you. Feel it find new places in your cunt. You have two hands. Use that other one on your clit - it isn't going to take much. I want to watch you come like you never have before. Do it!"

I followed her instructions and gasped as I moved my hand. I can barely describe the feelings; something was alive and moving inside me and places that I had never noticed before were suddenly registering sensations that had never been felt before. And when I added the stimulation of rubbing my swollen clit, I felt my pussy contract and twitch. I felt my muscles jerk and spasm without any ability to control them. My insides exploded and I was transported to some other world. A world of overwhelming sensations. I might even have passed out. I came back into the world to the sound of Sally's voice.

"Amazing, Ann. Simply amazing. You are really going to have to watch the video to see what you looked like - I can't begin to describe it. Now you should take our time and pull out your hand, then stretch so you don't cramp up from that work." Again, I followed instructions. "How was it, Ann?"

"It was the most amazing orgasm ever. I don't know what made it that way. Was it the size of my fist? My being watched? My being told what to do and when? Whatever it was, I am still feeling waves over sensations rolling throughout my body. It's almost like the sensation of being stoned on really, really good weed. I just want to lie here and absorb it. But that's not fair to you." I started to protest.

"Don't worry about that. Really. You should just enjoy it for now, and think about this - it will be orders of magnitude better when you can just lie back and get it done to you. I can hardly wait! I am going to rock your world, woman! Now get some sleep. And, in case you are wondering, I'm going to watch the video I captured while I stuff myself with toys and use my favorite clit vac at its highest setting. Good night, and sleep well!":

She hung up and I just got lost in the sensations until I fell asleep. Getting through the next day was a bit challenging - I was tired all day, as well as somewhat sore. I had to work hard at walking normally and not look like I had spent the night with my legs spread wide. Which, of course, they had been, but I wasn't really anxious to broadcast my recent activities. In any case, I managed to get in without a fuss, spent most of my day in my office, at my desk, and between coffee and aspirin - and a covert cat nap or two - I made it until the end of the day. Once I got home I stripped down and threw on a sleep shirt, had a bite and fell asleep on the couch watching the Justice League movie. I didn't even look at my computer! I was up early, refreshed, and took a moment to check into my profile - there were more emails, but for now I was avoiding them. More importantly, I grabbed an overnight bag, put in a couple of changes of clothes, cosmetics and some of my favorite toys and put it in the trunk of the car.

Worked seemed to go on forever - or maybe I was just anxious. In any case, I stayed late to finish some things, but mostly so I wouldn't appear overly anxious by arriving an hour early. I finally left, and before I did I stopped in the ladies room and took off my bra and panties. If there was ever a night for going commando, this was it! Then I headed for the restaurant and my meeting with Sally. As I walked in I was a little self-conscious, wondering if people would notice I was bra-less. When I heard myself worrying about what they would think, I laughed. I was a cum crazy slut who loved stuffing big things into her pussy, coming to meet up with a woman of similar tastes. Who cares what others think! I was chuckling as I entered the restaurant, and saw Sally (thank goodness for Facetime, right?) at the bar at the same time she saw me. We wound up embracing as if we had known each other forever. I already liked this woman!

Taking a seat, she asked me what I had been laughing at when I walked in. "Simple," I said. "I came here tonight after placing an online ad for some pretty perverted actions and discovering that others didn't think them perverted at all. I was coming here to meet with you because we both have an affinity for extreme sex and we already knew it - and I was laughing because I heard myself worrying about what others might think if they noticed I had taken off my bra - let alone come in with any panties on. Watching how automatically I worried about 'what they might think of me' when I really don't give a fuck struck me as funny. What do you think?"

Sally started giggling. "I for one definitely noticed how freely your boobs moved, and I liked it. Makes me think I should do the same thing - except mine are bigger and they sag a lot more. We will definitely get some attention if I lose mine!"

"Then do it! I'll order drinks while you do. I'm having a slippery nipple - you?" We laughed.

"Make that two - and I'll be right back. See if you can see the difference when I come back."

It didn't take very long. The drinks were at the table as I saw Sally emerge from the ladies room. There was a definite difference - her big boobs moved freely as she walked back to the table. I noticed a number of heads turn as she did.

"You know, every once in a while, I wonder what it would be like to have a pair as large as yours. They are eye catching, and very inviting. I notice you unbuttoned a good deal as well. How much are you planning to show?" I asked.

"As much as I can without legal consequences." And with that she unfasted another button to show a v of flesh that almost reached her navel, and displayed the inner halves of her large tits. I had to work to drag my attention from them to her face. "And while the girls can definitely draw a crowd, they're also heavy. That bra now sitting in my back is specially made to add back support. I'll live, and I like the attention. Especially from you! Drink up!"

I downed my drink and let the waitress know we wanted another round with our dinner (we both ordered burgers and fries). It was fun watching her try not to stare at Sally's display of mammary flesh. We laughed about it when she left, and then I gave her a commentary on who I could see around the place still staring, hoping to see more. She, in turn, let me know that I evidently had some admirers there as well.

"Probably because of your nipples appearing very prominently" she said. "Aren't we the pair? Sluts-are-us, at your service!" We were still laughing when our food arrived, and I made sure to stick out my chest was the waitress placed my meal in front of me. I watched her eyes as she did - it sure looked to me as if she would be very happy if we invited her to join us for a more private meal. When she left I checked in with Sally.

"She seemed awfully interested. Maybe we should see if she's interested..."

"If we come back here for any reason, and she's here on duty, we will. The more, the merrier. But not tonight, Ann. Tonight you are mine to manipulate. Mine to tantalize. Mine to torture. After that, we'll see. So let's leave and get dessert back at my house, shall we?" I nodded, we called for the check, and walked out to the parking lot, well aware of all the eyes on our boobs. Just before we walked out the door, Sally muttered "Watch this," then turned around to face the room and pulled her blouse open, flashing everyone. The reactions were wild - and then she closed the curtain and we left, laughing.

We somehow made it back to her house, a single floor, single family home in a neighborhood with lots of space between homes. I mean, we were both under the influence, and I was following her since I didn't know where to go. She pulled into her drive, I pulled up behind her and we stumbled to the door, her shirt flapping in the breeze and her boobs seemingly with a life of their own. We got inside and she turned on some lights.

"The bedroom is down the hall. Use the bathroom and get good and empty. Then get naked, get up on the bed and on your hands and knees. I'll be there in a minute. Now move, bitch!" I was a little surprised at what seemed to be a change of personality, but I had put myself in her hands, so I simply followed instructions. When I got to the bathroom, I found an enema kit in the sink. In lipstick, on the mirror was a note: "Use it!" and an arrow pointing to the sink. So I did. I was never a big fan, but she was in charge, so I got naked, set my clothes aside and did what was needed. I stepped out of the bathroom into a darkened room, lit by candles. Sally stood there, naked, with a very large dildo protruding from a contraption around her waist. I stopped and looked at it.

"That's bigger than I'm used to" I said.

"I'm sure it is. But don't worry - by the time we use it, you'll be ready. Now, up on the bed. Face the wall and spread your legs wide. And the proper response, by the way, is yes, Mistress. Understood?"

"Yes, Mistress."

"Remember what you are here for. You came here for pain and pleasure. You came here because you can only be satisfied by suffering as you come. I know that. I am an expert in that because I am the same way. You are mine. Your pussy is mine. Your ass is mine. If you need me to slow down, the safe word is yellow. If you need me to stop completely, use the word red. We'll pause on yellow and drop out of role to discuss things. We'll stop immediately on red and do the same. Other than that, you are free to say anything you want and I'll probably ignore it. Are you nervous?"

"Yes, mistress."

"Good. As it should be." And then I felt the bed shift as she got on it. Suddenly, warm hands were holding the globes of my ass and caressing them. The circles they were making were getting closer and closer to my sensitive spots, and soon her hands were toying with my lips. They were moving up and down my crack, slowly pressing into the flesh around both my asshole and my pussy. I felt myself getting moist, and my hips began to respond to her strokes. Then I felt hot breath in my crack and the sudden stabbing of a hot, wet tongue on my newly freshened asshole. I moaned.

"You like that, don't you? You weren't expecting that, were you? No need to answer, just enjoy the sensations." Then her tongue was once again probing that rear hole, pressing harder until I began to relax the muscles and allowed her entry. The minute her tongue was in me, she inserted a finger deep in my pussy. As she continued her oral attack, she soon added another finger, then another, and when she slipped her pinky in as well, I began to come!

"Oh, this is going to be fun! I need to record this!" With that she left me on my hands and knees, my asshole wet and now empty, my pussy pulsing with the remains of the orgasm. I had put my head down on the bed and had closed my eyes to enjoy the sensations. Though my eyes were closed I heard a snap as sensed the room brightening as she turned on the lights. As I found out later, she had a pretty elaborate camera setup that she then activated - it later let me watch my facial expressions as she kept expanding me, as well as what and how she was doing. The end result is far better than any amateur porn I ever encountered. I became an art film, essentially.