Derek and the Dating App by Kurogane335

Rated: 🟡 - Sexual Themes
Word Count: 4033 | Views: 16 | Reviews: 1
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Added: 04/03/2025
Updated: 04/05/2025

Chapter 4

I had half expected for it to be hard – some of those girls really didn’t want to post pictures of them after their growth, and didn’t presented their height, which made it harder to guess if they were just slightly taller than normal peoples, or already in the mini-giantess zone I wanted to get out, to meet some really big gals. But there were some, in the ten meters and plus range, which attracted his attention. They seemed harder to please however, because he hadn’t a match with one of them until several hours after he started liking their profiles.

And one of those really struck my fancy. For starters, she seemed really proud of how round she was, which was great. I didn’t want to meet up with someone who was ashamed of herself anymore. Secondly, she didn’t hide that she had sexual needs equal to her size. And finally, she loved her new height, towering at a whooping twelve meters tall, making her some really big gal. She was called Jessica and she seemed to be really funny and dominant. She didn’t shy away from the fact that if I wanted to meet her up, it was because I loved big girls and she told me in no uncertain terms that she’d make use of it.

And she had one picture in particular which impressed me. She was standing tall next to what was clearly an old, rusted, bus which had been lifted to stand on its rear. It was a little bent and broken and I was almost willing to bet that when it had come crashing down on the ground again, it had broken into many pieces. But most importantly, it was slightly smaller than she was. And there were traces of her fingers imprinted in the rusted hull. It was absolutely stunning and a good reminder that those giantesses were really extremely tall.

We agreed to meet the next day. She had some things to do and she would be here only around noon, but I was okay with it, since it could possibly mean that I’d have time to prepare the ground, especially by buying a lot of food. She was an eater after all, I already knew she had been before the Pandemic, and there was no way she wouldn’t be one now. It occupied most of my day, and the next morning of course, but I felt I was able to cook enough for both of us, with time to spare for a quick shower, before I jumped into a short t-shirt, waiting for Jessica to arrive.

And what a sight it was when she did! She was absolutely gigantic compared to me, easily dwarfing all the women I had met who had changed because of the Pandemic. It was absolutely mind-blowing and I won’t lie, I had a sudden wave of terror wash over me – how couldn’t I, when I noticed that she could easily crush me, and possibly even eat me whole if she wanted to – which seemed dubious, to my knowledge no giantess had eaten anyone –yet. I couldn’t wait to see how the ground endured her stomping around.

“Hey Derek! I’m glad to see you’re really here! And damn, it smells so fucking good! I hope you’ll have prepared something for you, because I’m famished, and in case you haven’t noticed, I eat a lot, especially since I grew a little!”

She stopped just close enough to be able to see me beyond the rim of her enormous tits, which protruded far from her torso since they were massive and supported by a belly which, while not monstrously bloated, was large enough to support her rack easily. It was a sight to behold. She had a far more casual look than Christina, and also a lot more confidence. She made me feel incredibly small, and yet I wasn’t afraid as much as aroused. After all, I could tell she would be playful, and it opened a lot of possibilities.

“Man, you look absolutely stunning” she boomed, waving at me and smiling as she did so. “It’s a fucking shame I’m as tall as I am – or you’re so short – otherwise we’d have been able to have some serious sex before lunch, it always makes the food taste better in my experience” she finished, before letting out a roaring laughter.

I won’t lie, I was a little surprised by how open she was to her sexual desires. Most peoples – men and women of course, but mostly women – were kind of too shy to voice such ideas. But I could tell from her grin that she wasn’t doing it to make me confused or anything, she really meant it and she wanted to see what I’d do now. I guess it was a way for her to set the mood and let me know what she wanted most and then act accordingly. After all, I suspected that if I tried to weasel my way out of it while still clothed, I’d have a lot of trouble coming my way. So I did the only thing I could.

I looked at her straight in the eyes as I removed my top. She gasped loudly and blushed, her pale white skin turning quite an interesting shade of red, even as her long black hair swayed around as she shook her head, clearly pleased by what I was doing. And she didn’t seem to want to be outdone because she started to struggle with the buttons of her shirt. I didn’t stop too long to look however, I wanted to show her that I really meant business and was more than ready and able to have sex before eating.

“Well, I’ll be damned. Didn’t expect you to be so eager Derek” she laughed as she dropped her shirt, revealing her titanic bra and starting to unclasp it, looking mightily sexy doing so. “I’m really glad I came here today. Just so you know, I always loved dominating my mates, so I hope you’re really ready for me, little man!”

I nodded, unable to say one word as she finally ditched bra alongside her shirt, letting them fall to the ground to her left. I kid you not, those things fell very slowly, her bra cups acting more like parachutes than anything I had ever seen, which should have been impossible, because when they collided with the ground, they did so with a loud thud, betraying the reinforced steel used to try and contain the glorious mammaries of the giantess, which a very honorable result, to be honest. And her shirt was definitely large enough to be a tent for me.

And she wasn’t over. It was clear than when she said she wanted to have sex, Jessica meant good old fashioned fucking, because she started to remove her trousers. Those were probably a size too small I guessed, or she had had them made before fully stopping her growth, in all directions. Or she had just gained some weight since then, which was a little frightening, because she’d need to eat a monstrous amount to do that, at her size. But her clothes were definitively plastered on her skin here, there was just no denying it for me.

“Hum, do you think you could help me with my shoes?” she suddenly asked me. “Honestly, they are a pain in the ass to remove, especially the knots. I’m just too big for that. It’d be awesome if you could at least unknot them, you know?”

“Uh… yeah, sure, I can try it” I replied, a little taken aback by her request, but I guess it made sense – if she bent forward to remove her shoes, she’d have a hard time reaching them indeed. “Not sure I’ll be able to remove them without your help however.”

“Oh, don’t worry, I’m sure we’ll be fine once you’ll have done that!” she chirped, grinning at me. “But you won’t get to see the real treasures I have until I’m out of my shoes!”

It was my turn to grin now, and I had a great incentive to make sure those knots would be undone fast. But as I approached her shoes, I realized it’d be harder than I assumed. For starters, the top of her feet were easily forty centimeters above the ground so I’d have to squat for quite some time or sit on her foot. And then, the knots were made of what looked like cables. I don’t know who the idiot who designed them is, but untying them would be an uphill battle, one I was very willing to wage, for the opportunity to see Jessica’s panty and what lay beyond.

“Okay, so it may take me a little time” I grumbled as I started to try and force the cables to move, even a little. “I hope you’re not in a hurry…”

“Don’t worry, I’m fine! Take your time, I like a man who endures things for a long time” she replied, and even if I didn’t look up, I could picture her smiling widely.

It wasn’t necessarily really reassuring, but I had no other choice than to try and do that. I decided to blindly pull the laces. I needed to understand the knots first. It turned out that they seemed rather basic, the same ones I used for my own shoes. Of course, their size meant that it was harder to unknot them, but I took my time and after almost five minutes, struggling with their friction, I finally managed to do it with one of her shoes. I just had to do that a second time, but first I let out a roar of victory, before falling to the ground when the giantess moved her foot as she laughed.

“Oh man, I had forgotten how funny it could be to be with someone. Ever since I broke the five meters mark, nobody seemed brave enough to meet me. I’m really glad that I came here, Derek. But do you think you could do it quicker for the other foot? I wouldn’t want you to make you go crazy, but I’m starting to get a little wet down there – or well, up here for you, I guess!”

I didn’t answer just yet, instead getting up, removing some dirt from my naked torso, and then sat on her other shoe. It was easier and quicker to unknot them, since I knew where I needed to pull, even if it remained exhausting, since I struggled with the laces themselves. Still, in half the time it had required me to undo the first one, I got up and moved away, so that Jessica could remove her shoes. She noticed right away and did so, by sending them flying over my head and crashing down a dozen of meters away or so, mercifully not colliding with anything I owned.

“Oh shit, I hope I didn’t break anything” she mumbled, before shaking her head, letting her dark hair cascade on her shoulders. “Oh well! You have earned some great reward anyway, so I hope you’ll like it!” she finished, letting her trouser fall down to her ankles before stepping out of it, giving me quite a sight indeed. “And just you wait until I’ll have removed that little, irritating, piece of cloth” she finished, laughing and pointing at the string she was wearing.

“Yeah, I can tell it’ll be incredible” I bubbled, as I couldn’t take my eyes off her.

I was stunned by the very fact that a string, a lace string even, was able to endure the strain that Jessica’s enormous ass and equally large thighs had to exert a lot of pressure on it. And yet, the pink thing managed to still hide the maw beneath. But it couldn’t do anything for its juices, which seeped through it, a testament of the giantess’ arousal. And I was the cause of it, even while I hadn’t done anything really remarkable. I won’t lie, it’s an awesome feeling, especially because I knew that physically stimulating her would be harder.

“But if you get yourself cleaned, at least the whole upper torso, arms included, it’d be great” she then told me, as she played with the rim of her panty, clearly teasing me.

I got the message loud and clear. She wanted me to use my whole upper body to get pleasured – perhaps she just even wanted to shove me inside of her, which I was in all honestly perfectly fine with. And I needed to be clean – or clean enough – for her to do that. After all, at her size, cleaning her insides was easy for someone like me but far harder for her, and if she could avoid getting anything dirty in it, it was definitely the best. I didn’t want an angry giantess who knew where I lived who had had an infection in her privates because I didn’t clean myself well enough!

I rushed inside to my shower. Better to be safe than sorry, but I wanted to do it fast. I almost jumped out of the few clothes I still had, and walked into it without even waiting for the water to get a little warmer. I shivered but didn’t care one bit. In less than five minutes, I had washed my hair, and my whole body, and walked out of the house, entirely naked save for my lace-less shoes. I didn’t want to get even the sole of my feet dirty. And I was greeted by an incredible sight, as Jessica was laying, her feet toward my house and her legs wide open.

“Come on tiger, don’t be shy. It doesn’t bite… but it sucks quite a lot” she guffawed as I stood frozen in place.

Answer honestly. What would you have done if you had been in my shoes? Would you have really turned around and run, terrified? Stuck in place, perhaps? If so, we are very different, because I dived right in. I kept my shoes for the time being, but I started almost immediately to caress those pink folds, which I clearly liked, considering how Jessica almost immediately started to moan and shiver lightly. And I could do that and lick the tangerine-sized clit of the giantess, without even having to truly bend or lean toward it at all. Truly an incredible experience.

It was even easier than I had expected. Jessica turned out to be very reactive to my lightest touch, and while I didn’t want to enter her just yet, because it did seem dangerous, I felt I could make her cum without risking a limb. Of course, it’d only hold true for as long as she wanted it, because she could probably catch me, lift me and drive me down without me doing anything to prevent it. Not that I’d want to do that, mind you. But it’s always best to not get away with the pleasantries when you’re having sex for the first time with a new partner, if you ask me.

“Of yeah, that’s wonderful” she moaned, when I lightly pressed her clit.

I must tell you I found myself a little tired in the arms, fast. Not because her folds were as hard and resistant as a normal person’s back or arms. But it was dense enough that I couldn’t just caress it and produce the best effects. I guessed it was because her size had made her a little less reactive down there, or she had always been harder to please than most of my former partners. I continued undaunted. I knew I had what it took to really make Jessica go wild before going wild on me, if you get what I mean by that.

I couldn’t see her face, of course, partially because she was too damn tall, but mostly because of the size of her breasts and – to a lesser extent – of her belly, which totally blocked my view. It was a little frustrating – because I love to see the effect of my work on a woman, often they look absolutely magnificent when they are reaching their orgasm, if you ask me. But it was also exhilarating, the very fact that I was going down on a woman over ten meters tall. I felt myself getting real hard, and I almost gave in and tried to ride her just yet, but I wasn’t willing to give in to temptation just yet.

I was startled when one of the enormous legs around me lifted itself and then fell again on the ground, with a loud thud, leaving a deep imprint into the ground. It was really a good reminder that, no matter how much I seemed to be in charge here, I wasn’t at all. If Jessica just closed her legs a little, I wouldn’t have been able to do anything to prevent her from doing so. Her legs were high enough that to get out of them, I’d need to scale them, which wouldn’t be an easy fit in a bind. And it turned out I was right to be worried about such an event.

“Okay, enough of that” she sighed. “I need to be in charge, and that’s how I’ll cum, little Derek” she groaned, as she closed her legs on me – not brutally but fast enough that I couldn’t avoid being trapped by them, as expected I guess. “Yeah, now that should be good. Lick me lover, it’ll be the best sex you’ll ever have, believe me!”

I panicked for a moment, who wouldn’t have? But I quickly realized that she wasn’t trying to hurt me, she just wanted to assert her dominance over me. So I did what I was told, which was easier said indeed than done. You see, her thighs were close enough that leaning forward to lick her down there turned out a little hard, since her flesh didn’t seem to be pliant at all, which surprised me, until I realized that I’d have probably needed a lot more strength than I possessed, if I really wanted to free myself, even just a little.

So I did what I was supposed to do and licked her. It wasn’t comfortable, not one bit, but it was also somewhat arousing. She dominated me so thoroughly that I couldn’t help but be impressed by her boldness. She truly wanted me to be submissive and I was happy to oblige, at least for the time being. Not that I’m a super submissive man, of course but I really appreciated the way she was happy to make herself the dominant one today. It wasn’t brutal or anything like that so it was incredible to be a part of it.

It was then that her hands descended on me – at least one all the time, sometimes the two of them – which massaged and scratched my back. It was a surprise but I appreciated it, it made it clear that I wasn’t just a prop and that Jessica cared about me enough for the whole experience to be pleasurable. It became clear however that it wouldn’t last, since I couldn’t do more than caress and lick her and I could tell, from her smell alone, that the giantess which was pinning me down wanted more – and so did I, even if I was afraid of what she’d do now. Well, not really afraid but you get my meaning.

“Oh yeah, that’s great. But I want you inside, Derek. Inside of me, and not just your dick, stallion” she sighed, giving shape to what I both dreaded and waited for with bathed anticipation.

She unpinned me, letting me fall on the ground when the support of her thighs was removed. I shook my head a second before I felt large fingers coiling around my torso. I marveled at their size, since each of them was almost as wide as my arms. She lifted me from the ground with such ease that I realized how strong she was, it was absolutely mind-blowing. And she chuckled when she saw my erect penis, going so far as to play with it a little with her other hand, whose fingers dwarfed it – and by now you should know that I’m quite large down there!

“Well shit, I’d loved for you to mount me before my growth” she sighed, looking longingly at it. “But then again, I guess you are bigger than your dick” she added, looking straight at me and grinned, licking her lips.

I wondered for a split second if she’d just shove me inside of her head first, which was an experience I both craved and dreaded. But thankfully, she didn’t. She lifted me high and then put my feet into her folds and pushed until I was waist deep inside of her. She hollered and shivered and I felt a great pressure on my lower body, especially my dick, which was pressed against the slippery walls of her pussy. It was absolutely incredible and I felt my eyes rolling as Jessica started to grind me down inside of her. We both gasped and our breathing quickened in unison.

Obviously, I struggled a little, but it was more to stimulate her than out of fear for myself. The suction on my lower body may have been extremely powerful, it was also quite pleasing, if I’m being honest. Even the pressure of her fingers on my torso, which made it a little harder to breathe, was surprisingly pleasing, if only because she massaged me, caressing me even as she used me as an oversized dildo. Don’t ask me why, but I found it surprisingly satisfying and stimulating knowing that I was too big for her, in a way. Dumb pride I guess.

We kept at it for god knows how long. I came inside of her, several times even, and I’m pretty sure she noticed, but she didn’t seem to care one bit. None of those women did, it was really strange. Usually, they were naturally very against me not wearing protection. I started to wonder if it wasn’t an after-effect of their growth. Perhaps that they have their inhibitions erased by it, or perhaps it’s even replaced by an urge to mate. I wasn’t sure which I found more frightening, that they could get pregnant without caring one bit or actually wanted to get a child!

In any case, I hadn’t much time to ponder about it just yet, since Jessica increased her pace, as she pushed me deeper in her, only to almost remove me. Her voice, as deep as it was because of her size, nonetheless became high pitched as she fervently pleasured herself, nearing her climax. Even then, I felt relatively safe, she didn’t increase the strength of her grip on me, after all, which was great and I focused on becoming as still as possible while also making sure that my legs didn’t get caught into something – I was fairly certain that she’d sooner break them than realize the danger I would be in if it happened.

“Oh fuck, yeah!” she wined, as she kept increasing her pace, so much that I started to feel a little nauseous and I swear I started to feel my brain colliding with the inside of my skull. “That’s so good! That’s so good!”

She let out a loud roar when she finally came, her fingers leaving me to grasp at the ground near her legs, burrowing deep into it and opening small trenches, as I’d discover soon enough. As it was, I was left panting – and cumming, inside of her as her whole body tensed, her humongous breasts seemingly increased in size before my eyes, until I realized it was just her breathing increasing so much that it gave me this optic illusion. In any case, it was absolutely awesome, and I felt very sad when I was removed from inside of her.

“Oh, that was awesome” she said once we had gotten cleaned and clothed again. “I’d really love to do it, but… you’re a tad too tall for my likes Derek! Sorry!”

And with that she was gone, leaving me scratching my head. I certainly hadn’t expected to hear that I was too big while meeting giantesses!