One
Any man will agree that sometimes you will do anything to get out of a dry spot. It had been nearly two years since I'd last been with a woman and not through lack of trying. I'd done the traditional meetup, talk, get to know one another and that went nowhere. I'd tried the go out, find someone, make it happen, but that hadn't worked either. I'd even tried a few online dating apps but got absolutely nothing. So understand before I start relaying what happened to me that I was in a weird place, yeah?
Going back to those apps for a moment, I'd sent out so many messages and never heard a single thing back. So, you can imagine my surprise when, one weekend after a week of typical drudgery at work, I got a message through from someone I'd never even seen before on the app.
'Hello Christopher,
You seem to be just the kind of boy I'm looking for. My name is Estelle and I would very much like to meet you. Respond and I will send you my address and a time. I look forward to hearing from you.
E x'
The way she had written the message was a little odd, certainly not what I was used to with any other woman, but the fact she had messaged me first and not the other way around was enough to make me abandon all caution. Well, almost all. I took a quick look at her profile and found out absolutely nothing. She had no photo, no bio, no nothing. She could have just been some bot account for all I knew but as we've established I was desperate. I messaged her back and almost immediately got a response.
'Wonderful. Come to my home at 36 Willow Grove for 1pm sharp. Make sure to have eaten. You will need the energy.
E x'
I wasn't too familiar with the address, so when I looked it up I was surprised to see it was in quite a high class part of town. Ideas about who this 'Estelle' was were starting to rush through my mind. Maybe she was the unsatisfied wife of some rich businessman who was away screwing his secretary, or maybe she was the daughter of some stuffy, upper class parents who was rebelling against them by bedding random strangers. Either way she wanted to meet at 1pm and it was almost 11am. I had just enough time to shower, eat and then make my way over there.
As I walked across town I took time to think about what she had said. 'You will need the energy' had been her closing words. I've never been much of a stallion in bed, but that seemed to imply she was planning to make this last a long, long time. I started to feel a swelling in my pants just thinking about it.
As I approached the address I saw that the house looked old but well kept. I entered the property through a wrought iron gate and noticed the garden was almost immaculate with identical rows of flowers either side of a stone path leading to the front door. Whoever she was she clearly had enough money to pay to keep her gardens maintained so that was a good sign. My predictions were looking more correct by the second.
I checked my watch as I approached the main door. 12:59. I was almost exactly on time. Clearly that was something that mattered to her so I hoped it would make a good impression. I rang her doorbell and waited. An intercom just below it crackled into life and I heard a female voice speaking from it.
"Yes?"
"I'm here to see Estelle?" I said, trying to hide my nerves behind false confidence.
"One moment please," the voice said.
I gave myself one more brush down and took a deep breath. Soon my dry spell would be over.
The door opened and I was met with maybe the plainest looking woman I had ever seen in my life. I don't mean that in a derogatory way at all, please understand, but nothing about her in any way stuck out as a prominent feature. She had short brown hair, very non-descript facial features, wore no makeup and had little to no visible body shape. She was wearing a plain white blouse, black slacks and flat shoes. It was like she was trying to be as ambiguous and forgettable looking as possible.
"E-Estelle?" I asked, nervously. Shamefully I was really hoping she was just the housekeeper or something but then she spoke and proved me wrong.
"1pm exactly," she said, checking her watch. "I do love a good boy who can follow instructions. You've eaten, yes?"
"Yes," I answered on autopilot, not really sure what was happening.
"Good. Follow me," she said, turning away from me.
I walked into the house and closed the door behind me. It looked as non-descript as she did, nothing at all out of place or remarkable in any way, almost as if it had been done purposefully. She took me into her front room, a weirdly clinical space that had two armchairs either side of a coffee table. She instructed me to take a seat in one. As I did, she sat opposite and picked up a journal and pen. It suddenly felt like I was in some sort of therapy session.
"So, Christopher, before we do anything else I have some conditions I require you to meet. Understand?" she asked.
"What conditions?" I replied, becoming more and more certain this had all been a terrible idea by the second.
"First and foremost, you must do everything I tell you without question or pause."
"W-wait are you some sort of dominatrix?" I asked her, preparing myself to bolt.
"No, just a woman who knows what she wants and expects to get it," she told me bluntly. "Secondly I will require you to sign a document that legally excludes you from discussing any of what you experience today with anyone else."
"Like some sort of NDA?" I asked.
"In a manner of speaking, yes. Thirdly, I and only I will dictate and decide what happens and when. We will be finished when I say so and only when I say so. Understand?"
I nodded, but admittedly my earlier trepidation was starting to become frustration instead. Who did this woman think she was? I didn't mind handing over control in the bedroom but she seemed to be taking this way too close into slave territory for me.
"Meet these conditions and I promise you you will leave here today having had one of the best sexual experiences of your life."
Her expression was unchanged as she told me this, as if it was something as inane as where to find the toilet in her home. I considered it for a moment. They say you shouldn't judge a book by its cover and there was a good chance that for as plain as she looked, she may have been an extremely experienced lover. Whilst there's definitely something to say for the enthusiasm of youth when sex is new and exciting, I'd heard that older women, even if only slightly older, were a different experience altogether, better in many ways. She had such an air of unwavering confidence about her that made me believe she meant everything she said.
"Ok. Where do I sign?"
She produced a document that had apparently been tucked into her journal and handed it over along with the pen. I looked it over and it seemed to legitimately only have the exact details and conditions she had explained so signed it and handed it back.
"Good boy," she said, taking it back from me.
"So, what now?" I asked.
"To begin with, Christopher..."
"Sorry, do you mind calling me Chris? Only my mom calls me by my full name," I asked, interrupting her.
"I prefer Christopher. Now, I am going to ask you a series of questions. These questions require complete honesty and so to ensure that, I will be connecting you to a lie detector."
"W-what?!" I started to protest.
"Or you can immediately disobey me and breach the conditions of our agreement. The door is right there and you can leave..." she replied coldly.
"Oh, s-sorry," I replied, immediately backing down.
"You are clearly new to this so I will allow some leniency. But do not presume to test my patience, understand?"
I simply nodded this time.
"As I was saying. Once you are connected to the lie detector, I will ask you a series of questions. If you lie to me more than twice, I will throw you out of my home and you will get nothing. Tell the truth, and you will be handsomely rewarded when the time comes. Now, wait here whilst I fetch the machine..."
I did as she asked, wondering how on earth I'd gotten myself into this and whether sex with this weird woman was worth it. Had she taken any longer I might have gotten up and left, but she returned quite quickly, wheeling in the machine and stopping it next to me. She motioned for me to hold out my hand and placed small clips on the end of my index and ring finger that held in place cables running off to the machine. She switched it on and I heard it whirring into life.
"We need to calibrate the machine so I will start by asking you a simple question with an obviously right answer. I first want you to answer incorrectly and then I want you to answer correctly. This will not count towards your permitted lies."
"Ok," I said with a gulp.
"What colour is the sky?"
Fighting the urge to answer correctly, I said, "green."
The machine buzzed to my right, a harsh electronic sound that almost made me jump.
"Good. What colour is the sky?"
"Blue."
No noise this time.
"Excellent," she said, taking a seat. "So, let us begin. Do you find me sexually attractive Christopher?"
I must have gone pale at that question. It caught me completely off guard. The simple answer was 'no' but if I said that, how would she react? Would this mean the whole thing was called off? But if I said 'yes' the machine would rat me out, and then not only would I have used up a lie but I would have to admit it to her anyway and I would have drawn her ire even more for lying. What should I do?
"No," I said, to silence from the machine.
Bizarrely, for the first time I saw her face curl into a slight smile.
"Good boy. I almost expected you to use up a lie, but I am pleased to see you are taking this seriously."
"You're not mad?" I asked.
"Of course not. Anyway, now that we have established that you don't find me sexually attractive, we're going to establish what you do. First let's start with hair colour. What hair colour do you find most sexually appealing?"
I was unsure where this was going, but there was no use in lying so I told the truth.
"I like black hair."
"Ok, interesting. Most men go for blonde," she said as she took notes. "Length?"
"Long."
"And what about complexion?"
"I quite like pale I guess..."
The machine suddenly buzzed.
"Wait, what?!" I said.
"And things were going so well," Estelle said with a disapproving look.
"B-but I do like pale girls, that machine is broken!" I said incredulously.
"Then have more conviction in your words!" she told me sternly. "Saying you 'quite like something you guess' isn't answering my question is it?"
"Ok fine. But that didn't count right?"
"Oh no it did. Hopefully it's a lesson well learned, yes?"
I was getting mad at this point. I was playing by her rules to a tee and it seemed not to be getting me anywhere. I decided I'd give her one more chance. I'd answer her questions truthfully and brutally if needed, but if that machine went off for a bullshit reason again, I was out of there.
"So," she continued, "pale skin and long black hair. Would it be fair to say that your ideal sexual partner should have quite a gothic aesthetic?"
"Yes," I said curtly, to silence from the machine.
"Hmm, ok. Not had that one before..."
"What do you mean by that?" I asked, curiosity suddenly piqued.
"No, no, no. I am asking the questions now. You may ask later if I so deem it."
I was annoyed that she'd brushed me off, but at least it didn't use up a lie.
"Ok. Describe to me the ideal figure for a potential sexual partner?"
"Well, she'd need to be a little shorter than me so let's say 5"2'. I'd want her to be slightly chubby, like not overweight but with a little meat on her bones. She'd have big boobs..."
"How big? Do you have a size in mind?" she interrupted.
"I don't know cup sizes," I fired back.
"Use your imagination then," she prompted me.
"Ok, err, well you know like a soccer ball?"
"That will do. And her nipples?"
"Her nipples? Erm, thick, like a cigar butt."
"Good. Continue describing the rest of her."
"She would need hips wider than her shoulders, a butt that was so big and round it stuck out twice the depth of her body and thighs to go with them."
It felt oddly satisfying saying all of that out in the open. I knew my 'ideal' was unrealistic to say the least, but nothing other than honestly would work here. I thought we were done but then Estelle caught me off guard with a final question.
"And what of her vagina? How would you like that?"
"Shaved or hairless and really tight. So she feels every inch inside her."
"I see," Estelle said with a slightly raised eyebrow. "And is this for her benefit or yours?"
"Both. Although I'd want her to cum first."
I saw Estelle look at the lie detector, still silent, and then grin slightly.
"You are going to work out far better than I'd hoped," she told me. "And with that my questions are over..."
"Oh thank god..." I began.
"All barring one. Christopher, how big is your penis?"
"Oh..." I said. "Err, I don't..."
I stopped for a moment, looking at the machine still whirring away. Estelle knew damn well I would have measured it at some point, what man hasn't? But even given the conversation we'd just had I was embarrassed to admit it.
"About 4 inches," I said with a slight grimace. The machine remained silent.
"Not bad," she replied.
She removed the clips from my fingers and powered down the machine. I was glad to be free of it and was now intrigued as to what would happen next.
"As you have shown that you can be a good boy and follow instructions, I have decided that you will be rewarded and that we will be having sex today."
She was very matter of fact and blunt, as if we had just agreed on some business deal, but I supposed that must be what this was to her. At this point, whether I was sexually attracted to her or not didn't matter to me. I had jumped through all her hoops and felt I was deserving of whatever she was able to give me.
* * * * *
Two
Estelle beckoned me to follow her so I did. She led me to a door that looked out of place compared to the mostly wooden ones adorning the rest of the house, this one being quite metallic. There was a keypad on the right hand side of the door which she tapped a number into, prompting the door to click as it unlocked. She opened the door to a set of stairs going downward, into a basement I would have guessed. Perhaps she had some sort of sex dungeon down there, I thought, and followed her in.
She led me into an open space that had what looked like some sort of lab equipment in it, all test tubes and computers and various machines that I hadn't got the slightest clue about. Most prominently in the room however was a large circular pad of some sort that was connected to a number of computers. I wanted to ask what the heck everything was, but thought better of it.
"Remove your clothes," she told me.
I did as she asked, nervously fumbling at the zippers and buttons of my clothing before removing it all and exposing my naked body to her. She seemed to look me up and down for a moment before approaching me and placing her hand on my currently flaccid penis. She started working the shaft up and down and I could feel myself starting to harden. She carried on until I was fully hard and then stopped.
"I can definitely work with this," she told me, a fire lighting behind her eyes that I hadn't seen before. It was strangely alluring.
She turned away and went towards one of the computers. I watched patiently as she seemed to be typing a few things into it and then heard the machine start to whir into life. She turned back to me and without saying a word began to remove her own clothing. Her body wasn't unappealing as such, but she had nothing about her that particularly stood out. She was slender but had almost no hips, bust or butt to speak of. I would still be more than happy to have sex with her, of course, but she wouldn't have turned my head on the street.
"Come here," she beckoned.
I walked to her and she once again took hold of my cock and started to stroke it.
"Now listen carefully Christopher," she said, staring dead into my eyes. "In a moment I am going to stand on that pad. I need you to do just one tiny thing for me."
"Name it," I said with a gulp, her hand moving more and more rigorously up and down my cock.
"Just press enter on the computer," she said. "Understand?"
"Y-yes," I said with a groan, the pleasure building in my cock as her strokes started to become too much for me.
"Oh, you're not about to ejaculate already are you Christopher?" she asked, quickening the pace of her pumping as she did. "Because if you ejaculate without me telling you you can, you won't get your reward..."
I desperately started to try and think of anything I could to ignore the pleasure I was experiencing. It was like some weird form of torture. Eventually I managed to get myself under control and mercifully she let go.
"Good boy," she said, that slight grin curling onto her mouth again.
She walked over to the pad and stood in the middle of it facing me. I waited for her command and when she gave it, pressed enter. The pad beneath her lit up, and the whirring from when the machine had been powered up intensified into a loud drone. I had a moment of clarity for a second and suddenly panicked. What the hell was I doing here? What was this machine? What was about to happen?
Before any of these questions could begin to be answered, my attention was drawn back to Estelle. She seemed different somehow. I couldn't put my finger on it at first but soon I realised that she was looking a little plumper than before. Not by a huge amount, but certainly noticeable. She also seemed to be a little paler too, her facial features much sharper and the hair on her head had started to darken and lengthen, I was sure of it! What I was seeing was impossible but my brain slowly started to put together what was happening. Somehow the machine was making her into exactly what I'd described. She even looked a little shorter, possibly 5"2' as I'd asked for. But if that was what was happening, that meant...
I watched in amazement as her breasts suddenly swelled and ballooned out into two massive and prominent globes on her chest. Her nipples had followed suit, like a pair of cigar butts, just as I'd asked for. Her hips started to widen past the width of her shoulders and simultaneously I could see her thighs bulking up. I couldn't see it yet, but I was certain her ass had also grown to the ridiculous proportions I had asked for. As a final touch it seemed, I saw the hair disappear from around her vagina. The drone of the machine started to wind down to nothing as I tried to pick my jaw up off the floor.
"Well?" she said as the machine came to a stop.
"T-th-that was..."
I couldn't even conjure words in front of the pale goddess in front of me now.
"It's certainly different than what I am used to but I could grow to like it," she said.
She looked herself up and down for a moment, casually squeezing her new giant breasts, and then looked over her shoulder for a moment.
"Oh my, you do like big things don't you Christopher?" she said with a grin.
She turned and presented the most enormously perfect ass I had ever seen. It was easily her most prominent feature and looked so soft and jiggly and yet firm.
"Ok, now it's your turn," Estelle said.
"Wait, what?"
"I gave you what you wanted. It's only fair if I get what I want in return, yes?"
"Erm, yeah. Yes, of course," I obliged.
I was a little hurt that she didn't want me as I was but then again that was pretty hypocritical of me in hindsight. I walked towards the pad and watched with bugged eyes as she confidently strolled past me, parts of her jiggling and bouncing in ways I couldn't have dreamed of before. I stood on the pad and watched her typing into the computer. She looked back at me for a moment as if considering something, grinned and then returned to her computer. I saw her press enter and the machine began to whir again.
"You know, I actually quite like you, Christopher," she said, "so the changes I've made will be minimal... in a manner of speaking."
The machine was running at full capacity now judging by the noise and I nervously awaited what she would change. Would she make me taller or more muscular perhaps? Maybe she'd change my hair colour or my face somehow. As I pondered this, I started to feel a tightening in my crotch, similar to the feeling of getting a boner, which made no sense as I was already hard. I looked down to see my cock gradually increasing in size. It was getting thicker as well as longer and pretty soon I started to look like the kind of stud I'd only seen on the internet.
"I guess you like big things too," I said to Estelle.
"Very, very big things," she replied, lust dripping from her words.
Realising what she meant, I stared back down at my cock, expecting it to stop growing any moment, but it didn't. It just kept growing and growing and growing. I could feel it throbbing with my rapidly increasing heartbeat and the weight of it against my body. By the time the machine started to settle back down, I had been endowed with a cock that would rival a horse.
"Holy shit!" I said, staring perplexed at it.
"It's bigger than I've ever dared go before..." Estelle told me.
"H-how big?" I asked, still trying to wrap my mind around all this.
"18 inches with a 10 inch circumference. In layman's terms you should be about 3 and a half inches wide in all directions," she said proudly.
"Fuck..."
* * * * *
Three
The term, 'third leg', is about the only way I could really describe my cock right then. It felt heavy but somehow remained fully upright, bobbing slightly with each beat of my heart. Estelle walked back towards me, her eyes glued on the cock she had made. She reached out her hand and gripped a hold of my cock, leading me by it to a bed I hadn't yet noticed in the corner of the room. Her hands had almost enveloped it before, but now her fingers barely went half way around it.
"Lay down lover," she told me.
I did as she asked, my cock sticking upwards like some obscene tent pole. She had to basically stand above me to have any chance of fitting me inside her which gave me an incredible view of her altered physique. Grabbing hold of my cock and holding it in place, she began to lower herself onto it.
"W-will this even fit?" I asked as I watched her struggle with the head.
"Hush now, Christopher, I'm concentrating," she told me.
I could feel the pressure building up at the end of my cock as she continued to try and push down. There was no give yet, but the feeling of her warm, wet hole at the end of my cock was heavenly in of itself.
"I'm beginning to think I should have disregarded your request for such a tight vagina," she said, a little strain in her voice from the effort she was exerting.
I was personally convinced that with the size she had made me, it wouldn't have mattered how tight she'd made herself, it still wasn't going in. I could see her becoming increasingly frustrated and was about to ask if she had any lube or something, before she uncharacteristically shouted, "fuck it!" and slammed her whole body weight down on top of me.
I yelped in pleasure as my ridiculous cockhead finally breached her pussy. She was still mostly squatting above me as it was just the head that had gone in but I could see her pussy was stretched wide, wider than should have been possible as if her hips would have also had to separate to make it happen. And she hadn't lied about the tightness. It felt like there was a warm, velvety clamp around the top of my cock as if it was being squeezed by an overzealous hand.
"Oh yes," she moaned. "This might be it, this might be the one..."
"What do you mean?" I somehow managed to ask.
"The one to finally satisfy me," she said with a victorious grin. "Now be a good boy and keep those lips closed while I work on this."
I nodded and watched as she edged herself up off my cock ever so slightly, just enough to gain a little purchase but not to remove me from her entirely. She slowly began to work her way up and down my cock, getting just slightly deeper each time. I've never known pleasure like it and it seemed to only be amplified by the fact she'd made my cock so obscenely big as if there was way more information being sent to the pleasure centres of my brain than usual.
Once she got halfway I felt an enormous amount of pressure on the end of my cock again as if I had reached some impenetrable part of her that I couldn't go past. She must have read my expression because she decided to explain.
"From previous experience, I'd say we've reached my back wall. I'm guessing that's something you've never done before Christopher?"
I shook my head.
"Don't concern yourself over it, very few men ever manage it. No man I'd ever been with did before I made my machine. We just need to give it a few moments for my body to adjust and then we can carry on. In the meantime..."
Estelle adjusted so that she was on her knees mounting my prone body instead of squatting over me. In making the movement, her enormous breasts swung increasingly close to my face and I had to fight with everything I had not to dive forward and suck on one of them. For some reason I felt like I needed to wait for her permission to do so. As she couldn't quite bring herself back further down on my cock yet, she remained in this position with her arms propping her up either side of my shoulders and her breasts hanging like some sort of exquisite forbidden fruit before my face.
"Since you've been such a good boy so far," she continued, "I will allow you to suck my breasts. However," she added before I could make a move, "I expect you to acknowledge me as I talk to you and if you don't you will lose the privilege of my breasts. Understand?"
I once again nodded, but far more fervently than before.
"Good. You may begin..."
She let out a contented 'mmmm' as I grabbed her breast with both hands and latched onto her nipple, immediately beginning to suck and tug at it as well as to lash at it with my tongue. Her breast was so huge that I thought it might envelope my whole face, the warm, soft meat of it covering my chin and both my cheeks at least.
"You probably have questions about my machine, yes?" she asked.
I made sure my eyes met her and nodded, not letting go of her breast as I did. She grinned at this as if acknowledging that I'd found some sort of loophole to her demands.
"Despite my natural appearance," she began, "I've never been wanting for sexual encounters. In my experience most men will sleep with you regardless of outward appearance if you show willing.You are quite simple creatures in that respect."
I don't know if she was expecting some sort of rise out of me at that comment but as far as I was concerned, she could say what she liked at that moment. I was way too lost in her breasts and the feeling of her warm pussy around my cock.
"Additionally I have found that the only real use men have in my life is the provision of sexual pleasure. Beyond that they are distracting and tiresome. And even then I eventually found that the pleasure I received was waning. Do you know what the average penis size is for a man Christopher?"
I looked up and shook my head.
"It's a shame you don't still have that lie detector connected to you as frankly I don't believe that you've never checked. I'll allow it though as I still have use of you. Anyway, the average erect penis size is just over 5 inches with an around 3 inch girth. So bigger than yours basically."
She was once again trying to bait me into making some sort of comment, but I merely looked back up at her as if to say 'ok, continue'. She seemed to like this.
"Some men I was with were above average, some below. Quickly I learned that size was the key to my pleasure and that any man I was with who was anything less than exceptional in that regard was barely worth my time or effort. As you can imagine with that low number being the average, it was very difficult to find exceptional. I found a man who was 8 inches once with a 5 inch girth, but that was an anomaly."
I had moved one of my hands onto her other breast and started to fondle it, which made her gasp slightly and made me feel very smug.
"My parents left me enough wealth to live a hundred lifetimes over and I have always had a frankly brilliant mind so I did what any self respecting person would and I started to research ways to bring that average up for myself. That led to me building the machine which I won't explain to you as you wouldn't possibly understand, but let me assure you it took a massive amount of time and effort."
I was starting to feel like this was some sort of rehearsed speech that she'd delivered many times before.
"Once I had my machine, I called upon a previous sexual encounter who was all too happy to answer my request for more sex. He had been one of the below average ones which made him perfect for my tests. I swore him to secrecy as I did you and made him a very respectable 9 inches with a 5 inch girth. He was delighted as you can imagine and we had very acceptable sex. Are you still following me Christopher?"
I almost missed her request that time but was quick enough to once again make eye contact and nod. I felt her starting to gyrate her hips slightly and let out a moan of my own as I took in the sensation of her insides moving against my cock again.
"I followed up my experience with him with a slew of others, subtly increasing the size each time. Eventually I ran out of previous partners and had to resort to how I found you, by posting on the internet. To my annoyance, however, many of these young men were either too proud or too dumb to agree to my terms."
Her gyrations were starting to increase in pace and depth and it was becoming increasingly hard to maintain my attention on her, so I ended up having to let go of her breasts.
"I started having to promise the best sex they would ever have, despite the fact that was undoubtedly true anyway, but then some of them even refused on the basis of lack of attraction to me. So I decided to make use of my machine to help the process along by determining what exactly they wanted. It had the added bonus of making sure they stayed fully erect throughout the process and maximised the pleasure they could give me. So as you can imagine I've spent much of my time as a tall, buxom blonde, not the curvy, gothic woman of your desires Christopher."
Her gyrations had started to turn into bounces and there was no doubt in my mind that I was starting to get deeper inside her again. She began to moan involuntarily as she continued to talk and slowly made her way upright.
"Before today... ah... the biggest I'd... mmmm.... The biggest I'd dared to go was.... Was... 14 inches with a... oooohhh... with an 8 inch girth. This is the... oh god... this is the biggest penis I've tried to take... and... aaahhhh yes!"
She cried out in victory as her hips finally met mine. I'm no scientist but what I was seeing should have been anatomically impossible. Her pussy was stretched wider than I'd ever seen one before and was accommodating what I've since learned was the equivalent of about four soda cans stacked on top of one another at a time. Despite this she'd somehow managed it and all I could do was stare in awe as she sat panting on top of me.
"Oh my god," she said through her panting. "This is the most incredible feeling I've ever experienced. It feels like your penis is inside every inch of me right now! This is my new standard, I can't go back after this!"
With that she started bouncing up and down on me again sending all of her own incredible proportions jumping around creating a visual for me that almost exceeded the pleasure I was feeling in my cock. I could hear the slap of her ass cheeks clapping together as she rode me adding to the cacophony of sexual noises sending my senses into overdrive. I reached out behind her as best I could and grabbed each of her ass cheeks, barely covering a meagre portion of each but enough for me to grab on and start to pull her down as I pushed up.
"Oh you good boy, yes, grab my backside and push deeper into me!" she moaned.
I started trying to fuck her in return with all I had, matching her bounces to my thrusts and generally losing all inhibition and control. Her breasts were flailing wildly in front of me and her face was curled into an expression of constant pleasure, somewhere between a smile and a grimace. Suddenly she lurched forward and locked her lips with mine, forcing her tongue in my mouth like she was trying to devour me. I happily reciprocated. When she finally pulled away she moved towards my ear and spoke.
"If you're a good boy and make me orgasm before you ejaculate, I'll let you have anal sex with me."
I have never concentrated so hard in my life. I kept every thought away from what I was doing, trying to imagine I was someone else for a moment like some sort of out of body experience, whilst maintaining the pounding motion I was making into her pussy. I took one of my hands away from her ass and planted it on the back of her head, taking a handful of hair as I pushed her back into another carnal and animalistic kiss.
"Oh good boy Christopher," she moaned between kisses. "Yes, pull my hair, make me do what you want!"
For the first time that evening, I felt some modicum of control coming back to me and I decided to use it.
"Get on all fours," I told her, sternly.
She looked at me for a moment, grinned excitedly and then did as she was told. She dismounted my cock, a task in itself, and then crawled up the bed presenting her enormous ass to me. I followed and lined myself up, a task that required far more distance than usual, and placed my cock head at the opening of her sodden and damn near ruined pussy that was still gaping slightly from the drilling she'd already received. I slipped back inside her and moved up the bed towards her until our hips were once again touching, relishing in how she moaned as I did it. I grabbed her hips and thrust forward with all I had. She threw her head back and screamed in pleasure which allowed me to grab another handful of hair. It had driven her wild before so I was going to make sure to do it now.
I started to well and truly fuck her with everything I had. She wanted an orgasm and she was going to get one or I was going to pass out trying. Her whole body jolted with each thrust, in particular her ass which rippled and clapped with each collision of my hips on hers.
"Yes, yes, yes, yes, yes!" she screamed with each thrust.
"Cum for me Estelle, I want you to cum right now!" I ordered her as I pulled on her hair and made her arch her back.
"Oh god, oh yes, oooh, ahhhh, aaaaahh!" she squealed, her moans getting higher and higher pitched.
Her whole body began to shake as she came and I instinctively smacked her ass cheeks as hard as I could as I continued to fuck her through her earthquake of an orgasm. She made noises I've never heard come out of a woman before but that I could only describe as what I imagine someone's soul orgasming would sound like. How I didn't blow my own load there and then is beyond me.
I felt her body go slightly limp and let go of her hair allowing her to slump forward onto the bed. She was breathing heavily and her body kept involuntarily shaking every few moments or so with the aftershock of her orgasm. I was still hip deep inside her and enjoying every little involuntary movement.
"You... you did it... Christopher," she panted. "No one... no one has managed to before. They always... always ejaculate before we're finished."
I felt a sense of pride that matched my own disbelief that I had outlasted her. I was desperate for my own release now though, particularly at the prospect of that release being inside Estelle's ass. I moved myself out of her pussy and started pressing my cock between her ass cheeks only to feel very confused as she moved herself away from me.
"Hold on, I thought we were..." I said, bemused.
"I am absolutely spent after that I'm afraid," she said.
"No, I am going to fuck your ass like you promised," I told her, trying to assert dominance like I had done before.
"Nice try Christopher," she said with a smirk, "but remember the conditions were that we're done when I say we're done, and I am done."
The walk home had been an odd one. Whether they could or not, I felt like everyone could see my new endowment. Certainly it felt a lot tighter in my pants, and I found myself trying to subtly turn away from any women I passed in the street. Checking out a woman and maybe getting a little worked up before would have been no big deal, but if it had happened now it would have been disastrous.
As I arrived home, a message came through from Estelle. In fact it arrived basically as I walked through the door to my apartment, a little unnerving really as if she could see I was home and had waited until then to message me.
'Hello Christopher,
I have taken the liberty of creating a profile for you on a site I have frequented before called 'SizeQueens'. Go to the site and use the username 'YesItsReal' and the password '18inches'. You should take some photos and add them as soon as you can. I've no doubt you'll have lots of interest. Let me know how it goes.
E x'
In a weird way it felt like Estelle was pimping me out or something, but as she had made it very clear that she saw what we did as entirely transactional (which worked for me to be fair), I suppose it made sense. I'd never heard of the site before but I figured I'd really had no need to beforehand, particularly if this was some sort of thing for women who enjoyed 'larger' men.
I went to the site as suggested and found I needed the login details to even just enter the main part of the site itself. Once I had entered the details Estelle gave me, I was redirected to my profile which Estelle seemed to have also taken the liberty to start filling in, listing my general location and age as well as my 'measurements'. There was an option to add photos but before I did that I wanted to get an idea of what I was getting myself into and decided to view the site's homepage.
Immediately I was met with a scrolling feed of naked men, particular emphasis being paid to their cocks in the photos. I had to admit, prior to my experiences that day I would have felt incredibly inferior next to most of these guys. They were all ridiculously well hung with the smallest among them being just over 8 inches but looking positively enormous compared to what I had been packing originally.
I started selecting some of the individual pictures which also had comments sections attached to them. My eyes widened as I scrolled through at the number of ridiculously horny commenters and some of the back and forths they were having with the original poster.
They were full of things like, 'I need a big cock like that inside me right now,' and, 'I want to be bred by a big bull cock like yours,' to which the poster would typically reply 'DM me and we can make it happen'. I selected another photo and the same thing. Lots of horny comments and offers to take things further. The same thing on another and another. It seemed that this site's only purpose was to get men with big cocks laid. Men that, only recently, now included me in their ranks.
Out of curiosity, I checked the profiles of the men I had viewed and whilst they all had impressive measurements, none of them went beyond 11 inches or came even close to my thickness.
'Wait till they get a load of me,' I thought to myself, excitedly.
With that I quickly stripped down and got my phone ready. Most of the pictures I'd seen were all of the dudes already hard so I figured I'd take a similar route. It wasn't difficult as I'd already started to swell at the idea of what I was doing. I took a moment to admire myself once I was hard again, the sheer size still being something that was a novelty to me.
Taking the picture proved surprisingly tricky as I struggled to get a good shot that would actually show all of it whilst also demonstrating that it was a real thing connected to a real human man. I had to get creative in the end and set up my phone to take a timed picture in my bathroom. My physique isn't anything to write home about but the photo got what I wanted and showed off what I was now packing very well.
I giddily posted it to my SizeQueens profile and waited. After I hadn't had any hits or comments for 15 minutes, I suddenly started to feel quite annoyed. I knew for a fact I was bigger than anyone else on the site and was expecting to immediately find myself inundated with requests, but nothing came. I almost jumped out of my skin in excitement when my phone vibrated to indicate a message coming through but then was immediately disappointed to find it was only Estelle.
'I see you've added the picture like I asked, good boy.
It will take some time for you to start getting hits on the site so in the meantime I want you to visit an acquaintance of mine tomorrow for lunch. She is a very graceful and elegant lady who enjoys a man in a suit. Whilst it's possible you may have one, you are partially representing me in this endeavour so I have decided you need a properly tailored suit.
You have an appointment at 4pm with a tailor's in town that is owned by a personal friend. They have been informed of your arrival and I have insisted on their best whom I am told is a bright young lady called Talia. I will of course cover whatever the resulting bill is.
Don't be late.
E x'
4pm left very little time for me to redress and arrive at the building in question. I was familiar with it but looked it up on my phone just in case, confirming that I would need to leave shortly to make it on time. Estelle seemed to have a penchant for timeframes that left very little wiggle room as if she enjoyed the challenge of everything running perfectly.
I caught a glimpse of myself in the mirror just before I left the apartment and could see, as I had suspected walking home, that my bulge was very prominent and noticeable. It seemed to naturally snake down the upper part of my right thigh and, whilst nowhere near as much of an issue as it would have been hard, stuck out like a proverbial sore thumb. I had just enough time to try and find a different pair of pants that might be less 'revealing' but if anything the rest of what I had in my wardrobe would only have accentuated the problem. I'd need to bite the bullet on this particular issue if I was going to make it on time, so, trying not to feel self-conscious, I left the apartment.
* * * * *
Five
It wasn't until sometime after leaving the apartment that it suddenly dawned on me that Estelle had effectively done exactly what I had mused over earlier and pimped me out to one of her friends. On the other hand however I'd had sex today and it now seemed I would be having more by the time tomorrow came to a close. After two years of nothing, it seemed like the universe might finally be cutting me a break.
I began to think about what Estelle had said about her friend in her message. She described her as 'graceful and elegant' which translated in my mind to her being one of those upper class, high art and ballet loving types. It also meant she was likely an older lady but if my experience with Estelle had taught me anything so far it was that that meant very little. I also started to wonder exactly what Estelle had told her given her secrecy surrounding her machine. I guessed I would find out in due course.
I arrived at the tailors almost to the minute that I had been told to and was greeted by a lady with a very refined accent who quickly confirmed with me that I was there for the 4pm appointment. I looked around at all the fine suits adorning the walls as she walked me through to the private fitting room she said I'd be using and tried to imagine myself in any of them. It was something I struggled to do, being more of a shirt and jeans kind of guy when it came to formality.
The lady ushered me into the room and told me that Talia would be joining me shortly. I took the time to take stock of how today had gone so far, starting with Estelle's first message that morning leading through to me standing in a high end tailor's in the afternoon. My life had gone from ordinary to extraordinary in a very short space of time.
Before I could muse any further, a young woman walked into the room.
"Hello sir, my name is Talia and I will be serving you today."
I was struck first of all by how pretty Talia was. Compared to the nondescript appearance of Estelle that morning, Talia in contrast had finely defined cheekbones, large, glittering, hazel eyes, a petite nose and small but plump lips. Her hair was a mahogany shade of brown and pulled back into a neat bun and she was wearing a similar suit pants and blouse combo to what Estelle had been wearing this morning, but the similarities ended there.
"Sir?"
It was at that moment I finally realised I'd been silently staring at her and so I finally acknowledged her, telling her my name and trying to hide the embarrassment from my voice.
"If you'd like to stand just there in the middle of the room please Chris and we'll start to take some measurements." she told me.
I did as I was told and moved to the centre of the room, standing patiently as I watched her arrange her equipment. She was very slender and didn't seem to be hiding much bust under her top, nor did she seem to have much ass beneath her suit pants. Whilst I definitely class myself as being drawn more to women with larger assets (my experience with Estelle making that very clear I think) Talia could definitely have been an exception to that rule. I caught myself before I could think about that any more as I felt a little pressure begin to build in my pants at the idea.
She turned back around with a tape measure in hand and approached me.
"Arms outstretched please," she asked.
I did what she asked and she took a measurement across from one arm to another. She then checked around my upper arms and my chest. I was starting to feel like a big shot but my daydreaming was broken into as she continued further down my body. She was now knelt at eye level with my crotch taking a measurement of leg. I fought with every fibre of my being not to get hard as the thought of what she could do in that position filled my mind.
I felt her hand brushing against my left leg as she measured and tried but failed to resist the urge to take a look down, just in time to capture her starting on my right leg. I watched her eyes move up her tape measure but then very clearly move to and widen at the sight of the bulge in my pants. She lingered there for a good few seconds and I could swear I saw her mouth open in shock a little before she quickly composed herself and then took back to her feet.
"Um, stay here please whilst I take the measurements to my boss," she said, before quickly exiting the room.
I let out something of a sigh of relief. Talia had seen the outline of my cock, and I'd supposed there would have been no escaping that given what she needed to do, but more importantly I hadn't gotten hard in front of her which would have been even more of a disaster. Talia returned to the room looking a little sheepish.
"What's wrong?" I asked.
"Nothing, nothing to worry about," she said, sounding as much like she was trying to convince herself as she was me. "My boss has asked me to get some additional measurements. They will require that you... strip down to your underwear please."
I must have gone a little pale, but before I could say anything she turned and said she would give me a moment of privacy. Left with few options besides just refusing and leaving (which I oddly felt was the worse thing to do as it would mean letting Estelle down), I removed the clothes I was wearing to discover my cock hanging out from beneath my underwear. I took a second to quickly adjust, thankful that Talia had looked away and hopeful that the material would hold me in place long enough for her to do what she needed to.
I let her know I was done and she turned back around. She was trying to maintain eye contact with me, I could tell, but her eyes kept darting downward to my cock. She once again approached me and I spread out my arms ready, allowing her to take the measurements she had before, and observed that she seemed to be following the same cycle. That meant it wouldn't be long until she was back on her knees before me again...
I tried to snap myself away from the image. For as crucial as it was before that I not get carried away, now it was critical because one wrong move and she'd be seeing all I had to offer. Once again she made her way up my leg, the touch of her hand on my bare skin now far harder to resist than before. I could feel it, the rush of blood cascading its way towards my cock, ready to make it swell and grow to an unreal size all while this poor girl just knelt there perplexed and likely disgusted.
She made her way up my right leg just as she had done before and I tried everything I could not to look and see if she had that same awed expression as before, but ultimately I failed this time. She was once again glued to my cock like she was waiting for me to grow it for her so she could see my full size. I might have been getting a slap or possibly even a restraining order for my actions, but I just decided to let go.
I watched her intently as I felt my cock finally growing free of my self imposed mental restraints. The shock in her expression grew exponentially along with my cock and I could see her breathing had gotten heavier too. I allowed myself to fantasise that she was imagining all she would do with such an enormous cock as it grew to the point of tenting the material of my underwear. The pressure being exerted on the end of my cock was becoming more and more intense as my underwear fought to keep it concealed, but even the waistband had pulled away now showing the thick and still thickening base of my cock as it protruded from my crotch.
I started to hear a tearing noise as I became aware that my underwear was finally losing the battle, but the ecstasy of the growth was too much for me to even think of stopping it and with a loud 'shriiiiip", my underwear tore and fell. Talia jumped in surprise as this happened but as she looked back up saw before her my fully erect cock in all its glory.
I could have basked in the look of awe and shock she was giving me for hours but now that the initial pleasure of my erection had somewhat abated, I started to apologise.
"I'm very sorry Talia..." I began.
"I... I thought that thing was a fake!" she stuttered.
"Um, no, it's all just me. Listen I..."
"And it actually got bigger! How is it so big?!"
"Err, I'm just naturally very gifted?" I offered as my explanation, just like Estelle had told me.
"Good god. You are the most 'gifted' man I've ever seen, Chris!" she said with a slight disbelieving smile.
The fact she was still on her knees had not escaped me. Increasingly bold thoughts started to swim through my mind.
"Erm, seeing as you have that tape measure there, do you think maybe you could measure it for me? I mean, if that's ok, I get it if not, it's just I don't have anything... big enough at home."
"I shouldn't," Talia said before looking around at the door. "B-but ok."
She adjusted herself into a better position and started to unravel her measuring tape.
"I'm going to need to, um, touch it to measure," she said looking up at me with those brilliant hazel eyes.
"That's ok," I said, trying not to sound too eager.
She hesitantly held the end at the base of my cock and I tried not to shudder as I felt her fingers running up the shaft as she measured. Again I watched her eyes widen as the tape went along further and further until it finally reached the head and she pulled it away.
"J-just over... god... just over 18 inches," she said with a gulp.
"What about around?" I encouraged her.
She nodded and wrapped the tape around, the pressure feeling heavenly against me.
"Ten inches," she read out.
If nothing else, Estelle's machine was definitely accurate.
Talia looked a little shell shocked so I decided it might be an idea to bring this to a close.
"Thanks for that Talia and sorry that this happened," I said.
"Don't worry about it," she replied.
I expected her to maybe stand and leave but she remained where she was, just staring at it. She opened her mouth a few times and quickly shut it again as if she was trying to say something but it kept getting stuck.
"Err, do you have a question or something?"
"I-I mean yeah I do but, well it's inappropriate and very personal to say the least..."
"Please go ahead," I said, intrigued.
"What's it like having to hide something as... just big as that?"
"It's challenging. Most of my clothes don't hide it that well. Particularly not when I'm turned on like this."
I figured the truth was probably best here, no need to make up some elaborate backstory.
"And have you ever, you know... done it with someone?"
"What do you mean?" I asked, starting to enjoy her line of questioning.
"Well, I mean it's just so damn huge, Chris, it can't possibly fit anywhere right?"
"It takes a lot of warmup but it's possible..." I told her.
Her eyes once again widened at that.
"In fact," I continued, "I was with a woman this morning who managed to take all of it."
"No way!" she said, jaw dropping to the floor again. "How do you even begin to approach that, I bet most women would be too scared to even try!"
"Are you one of those women?" I asked in a moment of uncharacteristic boldness.
Talia was speechless for a moment. I could see her cheeks turning red as she fought the embarrassment of whatever her first thought was and finally managed to break her stare away from my cock.
"I-I've got what I need now so I'll just leave you to get dressed," she said.
"Of course, sorry Talia. I got way too carried away here, with the whole thing. The woman I was with completely blue balled me, not that that's an acceptable excuse, so I'm kind of over-horny right now."
"S-she did?" Talia said quietly as she started to turn back towards me.
"Yeah, after I held back to give her 'the biggest orgasm of her life' in her words," I added.
Talia seemed once again to be stuck. She was looking between my cock and the door, her head going back and forth as she tried to figure out what to do. Finally her gaze fixed on the door and she moved towards it. It was to be expected I guess and I supposed I was just lucky she hadn't had me thrown out of the store as soon as I'd started getting hard. To my surprise however, she locked the door and turned back towards me.
"J-just to be clear," she started, "I never do this. This isn't a thing I do. But... well if she didn't let you cum earlier then you must be in a bit of pain right now, yeah?"
"Yeah a little," I told her.
"Ok. Ok."
She seemed to be taking a few deep breaths before continuing.
"I'll help you to cum, alright? But it'll just be with my hands because that thing would ruin me even if we only even tried to do anything else."
I immediately imagined how tight her slender body would be and felt my cock swell and pulse in response.
"And we're not supposed to lock the doors for safety reasons so if my boss or anyone else comes and tries that door and can't get in, we've got about 30 seconds before someone knocks the door in, ok?"
"Sure," I said, scarcely believing my luck that I would be getting pleasured by another woman today.
"Alright. L-let's do this then."
Talia got back into position on her knees and, after another deep breath, tentatively reached out for my cock. Her fingers were soft against it and I felt bolts of pleasure course through my body as she tightened her hold slightly and began to slowly work her hand up and down the shaft.
I was furious. I had deliberately held back based on the promise of anal and now it had been taken away because of some stupid contract the stuck up bitch had forced me to sign.
"Oooh, look how angry you are," she mocked me. "Well never fret my dear. You've been a very good boy today and followed all of my instructions. I am a woman of my word and you will get to have anal sex with me... just not right this second."
"Well, when will that be?" I asked, feeling both frustrated and confused.
"Whenever the mood next strikes me to have anal sex," she smirked.
"You absolute bitch," I seethed.
"Aww, I know you feel a little cheated but those are the rules you agreed to," she continued. "I tell you what though. Seeing as I like you and you succeeded where all other men have failed, I'll let you keep that penis at the size it is until we next meet."
"Are you serious? This thing is way too big and unwieldy, I'll be knocking things over with it!"
"You'll get used to it," she dismissed me. "And maybe in the meantime you can get a little more use out of it. I'm sure there's plenty of women out there like myself who would relish the opportunity to be filled past breaking by a giant penis."
I had to admit she maybe had a point, as much as I didn't want to give her any credit right now.
After waiting for my ridiculous cock to finally soften (and being slightly amazed that it was still just above the size of the average erect penis when soft) I got dressed and ready to leave. Estelle had gone back into her machine and returned herself to normal before also getting dressed.
As we left the basement and she closed the door behind her, she stopped me in the hallway.
"Remember, Christopher, you are still under contract. You cannot share any of what happened here or the contents of my basement with anyone, are we clear?"
"It might be difficult to do that when you've left me with this thing," I said motioning towards the outline of my cock in my pants.
"Then simply do not explain it. Just tell them you are naturally gifted. Now, more importantly you should be aware that my desire to have anal sex may come at any time and that if I tell you I am ready, I expect you to be here and ready within the hour, otherwise the offer is rescinded."
There was no point arguing with her now so I simply agreed.
"Good boy. Now run along and have some fun. I expect you to keep me in the loop about all of your experiences. It may even prompt me to be ready for anal sex."
With that I was finally out of the door. What a wild few hours it had been, certainly not what I expected. I had to admit that despite not finishing, Estelle's promise of the greatest sex of my life had been fulfilled but now I could feel that my balls had begun to ache from lack of release. I would surely have to do something about that soon but for now my thoughts turned to how to use my new equipment to my advantage...
"God, my fingers don't even fit around it, they're barely half way!" she said with a laugh of disbelief.
She added her other hand and it only compounded the effect.
"Holy shit, look! They barely meet!"
I don't know if she was doing it deliberately or not, but her strokes started to become more heavy handed and I let out an involuntary groan at the pleasure she was putting me through.
"I-is that good?" she said.
"It's amazing," I told her. "God you're stunning."
Whilst true I hadn't intended to say that but in the heat of the moment it just came out. Fortunately it made her shyly smile and giggle slightly before letting out a small 'thanks'.
"I wish I could see what's beneath those clothes," I told her, hopefully.
"Sorry, it's too risky," she told me. "But perhaps..."
She thought for a moment.
"Perhaps you could tell me what you'd do to get me ready to try taking this thing if I were naked?"
'What wouldn't I do?' Was my first thought but she clearly wanted more detail and I was all too happy to give it.
"Well, I'd start simple. We'd kiss until we'd kissed every corner of our mouths..."
"Yeah?" she said, her pumping increasing in speed slightly.
"Then the kisses would lead down your neck until I reached your breasts. I'd suck on one of them and use my fingers to tug and squeeze your other nipple."
"That sounds good," she said, biting her lip a little and once again pumping just that little bit harder.
"Then I'd continue to keep kissing down your body until l reached your vagina..."
"And then what," she encouraged me, her pumping starting to reach fever pitch.
"Then I would eat you out and make you cum so many times that your vagina would just be drenched in your own juices and my saliva..."
"That's sounds so fucking good," she continued, her pumping frenzied now.
"And then I'd..."
"Y-you'd what baby?"
The pressure building up in my cock was about to flow over in the biggest way imaginable.
"Oh god, I'm so close, I'm gonna cum!" I warned her.
This was going to be big, I could just tell. For a brief second the thought of 'where am I going to cum that will cause the least damage?' flashed through my head, but Talia apparently had different ideas. Without warning, she placed her mouth on the head of my cock and continued to pump ferociously. It was too big to have any chance of going in further but she had the danger area covered, ready for me to unload in her mouth.
I wanted to reach out and grab her head to maybe try thrusting in a little more, but the size of my cock made that too difficult. Instead I braced as I felt my first shot shoot up my cock ready to unload and then moaned as what felt like the longest blast of cum I had ever produced exploded out of the end of my cock and into Talia's mouth.
Into Talia's throat may have been more accurate, as I heard her cough and gag in surprise at how much semen had just filled her mouth. To her credit though, and perhaps with cleanup in mind, she managed to not let a single drop escape the edges of her mouth and remained locked on the end of my cock. With nowhere else for it to go, I remember hearing her swallow what sounded like a large mouthful.
She kept this up as I continued to cum, filling her mouth and then her swallowing with an almost rhythmic motion. I started to hear muffled moans of her own trying to escape her throat and looked down to see she had undone the front of her pants and was furiously working away on her clit as she continued to swallow my load. A minute or two later and I was done.
Talia continued to run her tongue and lips around my cock as if French-kissing it and must have came whilst doing so but was trying to keep quiet as possible as I felt the air leaving her and her body trembling. She removed her hands from her underwear and then finally pulled away from my cock.
"Holy hell," I told her with a grin.
"Sorry, I got a bit carried away myself," she said with a shy but knowing smile.
"I'll say," I said, indicating her hand.
She raised it up and I watched as her vaginal juices started to drip away from it in strands.
"May I?" I asked.
She nodded and I gently took each of her fingers in my mouth in turn, sucking them dry of her nectar. She tasted unbelievable and I was suddenly sad I'd not be getting to drink from the source. She grinned lustily as I did it.
"That was one hell of a load," she told me as she buttoned her pants back up and started to try and make herself presentable. "Is it normally like that or are you just a bit backed up?"
"Well it's been a while so I'd say the second one," I laughed.
My cock had finally started to soften now but my underwear was beyond help so I had no choice but to go commando. All it did was make it even clearer that I was packing an unusually large cock, but somehow I really didn't care right now.
Talia unlocked the door and turned back to me as I got dressed.
"Once I get these last measurements to my boss, she'll start work on your suit right away. I think she said it's already been paid for and there was extra for a quick turnaround?"
"Yeah that sounds about right," I replied as I pulled my shirt back on.
"It should be ready to collect tomorrow morning."
"Brilliant," I said.
I made my way towards the door and turned towards Talia.
"Thanks... for everything," I said with a grin.
"My pleasure," she grinned back.
* * * * *
Six
I had returned home with a certain spring in my step after my experience with Talia. I caught one or two shocked glances towards my crotch and a few averted eyes on my way home but rather than being embarrassing, they seemed almost humorous to me now. Estelle messaged me as I walked but I decided to leave her message for after I got home in case she dulled my buzz in some way.
Once I got home, I opened my phone and read what she'd sent me:
'My friend has informed me you arrived at the shop on time and the order has been made. Good boy.
She also tells me that her young assistant Talia seems to have been in a good mood ever since she served you. Do you have something to tell me about Christopher?'
For a moment I was a little unsure whether I should tell Estelle what had happened. I didn't want to get Talia in trouble after all. But then I remembered she'd made me agree to tell her all about my exploits so I decided, 'what the hell,' and gave her a brief roundup of what had happened between Talia and me. I waited a moment for her to message me back.
'Well done. I'm impressed you managed to talk her into doing that. I'd anticipated she may agree to a separate meeting before going ahead with some kind of sexual intercourse after seeing your size but you are perhaps more adept at seduction than I thought.'
I was taken aback a little at this as, so far as I was concerned, the visit had solely been about getting my suit and the experience with Talia had just been an unexpected, but very welcome, bonus. I asked her if she had sent me there with that in mind.
'Not initially. But once my friend told me about the young girl she had on the staff, my curiosity was piqued as to what you might do in that situation and by proxy what she might do. It is satisfying to know your penis proved irresistible, particularly to an unknown party who may not have the larger size preferences some of us do.'
I decided to not ask further about this as Estelle was slowly making me feel like a lab rat and the experience I had decidedly less sexy. She seemed to want to move on herself however as I could see her typing another message.
'Now onto other business. You should check SizeQueens, I believe you have some comments on your picture.'
I quickly went back onto the site in excitement, wondering what horny delights might await me in the comments only to be immediately disheartened. Of the 13 or so comments all but one of them just said 'fake' or words to that extent. The one exception was a little more promising, saying 'would 100% ride this until I couldn't walk anymore... too bad it's probably fake.' I decided to make a note of the username on that one (hornygurl616) just in case, but otherwise I was really annoyed. Estelle was typing again and another message popped through.
'I take it you've read them now.
I had my suspicions this would happen as you are far bigger than anything else to offer on that site. I should know, I wouldn't need my machine otherwise. You'll just have to provide them with a little more compelling proof.'
As I took a moment to figure out what this proof would be, another message came through.
'You should take a video of yourself. First demonstrate that your penis is one hundred percent connected to your body and then give yourself an erection and show off the full size. It'll be a little harder to call you 'fake' after that.'
Less than 24 hours ago, the idea of posting a video of myself like this online would have terrified me, mainly out of fear of being discovered by someone I knew or the potential for outright rejection by so many people. Right now though it seemed like a great idea, any other consequences be damned.
I rushed up to my bathroom and set my phone back up in the position I'd used earlier on that day before stripping off. I was getting used to seeing my cock being so huge now but it was still making me grin like an idiot. I took a quick test video just to make sure my face wouldn't be in frame before starting the video properly; it was the last bit of caution I had for my privacy I think, plus it seemed the standard thing to do in the pictures I'd seen. I hit record and got into position.
I decided to narrate what I was doing on a whim.
"Seeing a lot of comments saying what I'm packing here is fake. Well, as you can see..." I said whilst moving closer to the camera, "this is all 100% me."
I moved around a little and thumbed and fingered around the base of my cock to demonstrate there were no grooves or seams to it and that it was completely connected.
"But it wasn't me soft you were all calling 'fake' right? Let's see what you think after this..."
I started working my already hardening shaft up and down. It was only the second time I'd done this to myself since Estelle gave it to me, the first time not really commanding as much attention, and it was bizarre to say the least. My starting point was already bigger than I'd ever been when hard before and feeling it swell and grow to such a huge size, forcing me to work more for it than ever, felt both amazing and weird at the same time.
I had to step back a little as I noticed I was quickly getting too big for the camera frame, despite only being half way done. I started to imagine the reactions of the women watching this back, picturing their mouths watering at the sight as their breathing grew more heavy and their heartbeats rose. It was an image that only served to harden me even quicker and soon I was standing at full mast.
"There. You want any more proof? DM me and we can arrange a more personal inspection..."
I felt pretty smooth as I switched the camera off. I decided to wait a few minutes for my cock to soften, mainly so it wasn't an obstruction more than anything else, before watching the footage back. I made a quick cut at the start and end of the clip to remove me switching the camera on and off respectively but aside from that, I was very pleased. In a weird way I was a little transfixed by the video as if it wasn't me I was watching but some other ridiculously well endowed dude.
I went back to the site and uploaded the video. Now all I had to do was wait. A minute or two later, I received what should have been the expected message from Estelle.
'A very nice video. I enjoyed seeing my work in action again and I see that your confidence is improving too. Perhaps my prompting you to take control in the bedroom has helped with this. Expect to be doing that more often, even the seemingly most in control and dominant women desire to become submissive and will do so once they experience your penis first hand, although many on this site are naturally submissive anyway.'
Estelle's assessment about dominant women was one I might not have believed without my experience with her, but she maybe had a point. It made me start to think about the women I knew I would have classed as being 'in control' or 'dominant'. Immediately I thought of my boss, Leanne, at the store I worked at. I had something of a crush on her but would never have dared approach her in that way. Besides, she could be a harsh taskmaster, needlessly so sometimes depending on who you asked, so it had always felt like everything was firmly off the table as far as she was concerned.
'Whomever it is you're currently thinking about seducing will have to wait.'
Her messages were starting to get borderline scary in their timing and accuracy now.
'Tomorrow you have a dinner date with an acquaintance of mine. Her name is Alexia Cavendish and yes, she is the billionaire heiress you've heard about on the news. To be clear, absolute discretion will be necessary here. You will be meeting her in her home at around 11:30 am where you will talk, eat and be generally civilised. Once she is ready, you will then be taken to her bedroom where the two of you will engage in intercourse. You will then leave and never speak of it to anyone other than myself ever again, is that understood?'
This was all starting to feel very secret agent, but for the little I knew of Alexia Cavendish, it certainly made sense. She'd made the news for arguably all the wrong reasons having been caught out by the media on multiple occasions with multiple different men, much to the chagrin of her real estate tycoon father.
'Alexia and I met via mutual friends where she expressed similar desires to myself in terms of the size of the men we preferred. Her exploits of late have been purely in the pursuit of this but of course as she's a woman in a position of wealth and influence, the media have crucified her over it. She isn't the brazen harlot the media would lead you to believe she is, hence you will need to observe some pleasantries first, but I can assure you that once in the bedroom she will likely do things you have only ever dreamed of.'
I could remember seeing pictures of Alexia in the news and from what I'd seen she was quite a pretty woman. Probably not as stunning as Talia had been but still something of a head turner. To be honest, I'd never paid the stories about her much heed, but I'd definitely be looking her up before tomorrow.
'Now, your suit will be ready to collect by 9 am tomorrow morning when the store opens. At 9:15 you have an appointment with a barber on the same street and then immediately after that you should return home to try on your suit and be ready to be collected by Alexia's personal driver at 10:30. Seeing as you've been such a good boy so far, Christopher, I don't see any of this being an issue. Make sure to get an appropriate amount of sleep tonight and message me in the morning when you leave the apartment.
E x'
Estelle seemed to have officially signed off for the night having given me my marching orders. It was still early evening so I wasn't going to be going to bed just yet, leaving me time to research and plan for the day ahead of me.
I got myself dressed into the loosest fitting nightwear I had and went back to my computer. In the matter of half an hour, I had already read multiple articles about Alexia and perused over a number of photos of her, including a fairly candid set taken as she bathed on her father's yacht in a bikini. Looking her up and down properly for the first time made my anticipation spike. She had a fairly average bust that was made to look bigger on her slender frame along with a skinny waist and a slight but pleasing curve to her hips. Her legs were long and toned and easily stood out as her most compelling feature, even for a man such as myself who wouldn't describe themselves as being a 'leg man'.
I also found a number of more raunchy sites online where men hidden behind anonymous usernames discussed what they would do to her in the bedroom. I felt a sense of smug satisfaction that I would likely be living out the fantasies of these men in less than 24 hours time.
After leaving it as long as I could stand (including a quick break for something to eat), I checked back in on SizeQueens for comments on my video. Estelle had predictably been completely right about the effect the video would have. Already I had at least 10 comments and they were looking far more promising.
'Holy shit!! Such a bull cocked stud, I'm literally drooling right now!!'
'You would put a horse to shame! Didn't think it was real but fuck me!! In fact, yes, yes please!!'
'Imagine the load that thing would blast all over you...'
'I never thought 'too big' could be a thing, but now I'm not sure...'
'Will the cock god message back?'
I was feeling decidedly big headed at that moment (in more ways than one) but was looking for a particular commenter before I did anything else, the only commenter that had been positive about my previous photo to be exact. I scrolled through and found exactly what I was looking for.
'I can't even describe how much I NEED this thing inside me. DM please?????'
I fully intended to offer DMs with anyone who commented, but I wanted to make a point of asking her first since she was the only one who had shown any real willingness before. It struck me as odd in this moment that she hadn't just messaged me directly already, but Estelle later confirmed for me that it was considered an etiquette thing on the site that only the posters could initiate the first message, further solidifying the notion of these women being submissive, she added.
I replied to her comment telling her to DM me and immediately her message came through.
'So happy you said yes to this. That cock is easily the biggest I have ever seen! And it's all natural? Like, you've never had any surgery or anything?'
I replied telling her it was 100% natural and that I'd never had surgery. I wasn't really lying after all.
'Watching that thing just keep growing and growing got me so fucking wet. You want to see?'
I wasn't about to say no to that. About a minute later I received a short video. She was completely naked and had a nice body, a bit on the chubbier side but that really works for me anyway. Her breasts looked to be a large handful each and I watched in the clip as she pulled her hand away from her pussy and her juices dripped down in long, sticky strands from her fingers. It reminded me of Talia earlier that afternoon in a very good way and I felt my cock begin to swell again.
'Do you think I'd be wet enough to take your monster cock?'
I assured her that she'd get as much as she could take. A moment later she sent me another video. As I played it I could see she had a tape measure and was slowly pulling it upwards from the entrance of her pussy up past her stomach to in between her breasts where, by the time she stopped, it had reached 18 inches. It was quite the visual and needless to say I was rapidly hardening now, so much so that I decided to just whip my cock back out so it could grow without restrictions. That and so it wouldn't tear my nightwear. I waited until I was fully hard, snapped a picture and then sent it back.
'Oh my god baby, it's so huge! I want that thing to RUIN me, I don't care if it's too big!! Please tell me we can meet soon!'
I was very tempted to ask her where she was right now, but I had a potentially important day ahead of me tomorrow. I asked her if she could wait until Monday and where she wanted to meet, hoping to avoid my place if possible, and her response was exactly what I wanted.
'Anything for you my horse cocked stallion. Can you come to my place?'
She sent me her address and we agreed on a time. She lived closer to where I worked than where I lived so I decided I would take a change of clothes to work and go on to meet her from there.
'I can't wait to feel you stretching me open baby.'
I bid her goodnight and closed down the site for the evening. This was incredible. When I'd woken up this morning it was with the same, longing morning wood that had remained untouched by another's hand for nearly two years. Since then I'd had my cock greatly increased in size, fucked the literal woman of my dreams and had my cock sucked and cum swallowed by one of the most stunning women I'd ever seen. Tomorrow I would be having sex with a gorgeous billionaire heiress and the day after that I'd be bedding a woman who seemed to want to worship at my feet. The phrase '1 to 100' went through my mind as I smiled and laid down to sleep.