Derek and the Dating App by Kurogane335

Rated: 🟡 - Sexual Themes
Word Count: 4200 | Views: 18 | Reviews: 1
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Added: 04/03/2025
Updated: 04/05/2025

Chapter 8

I prepared myself for this encounter of course. I even paused my account for up to a month. News flashes had said that most recent cases seemed to grow far larger than the previously affected and that some girls suffered from a form of long-growth which made them reach absolutely mind-blowing sizes, massive enough that it was hard for all parties – themselves included – to remember that they were born humans. At least, that’s what some tabloids said, but I didn’t really trust those and instead focused on physical preparation.

After one month, I was confident in my ability to survive such an encounter and I returned to the app. And just as I had expected, a forty meters tall colossus quickly matched with me. It was surprising because that girl, a black woman with breasts at least thrice as big as her head even before she grew, had kept a relatively similar physique than when she had clearly been very petite. If there hadn’t been tall trees reduced to a measly size next to her, I would have doubted that she had grown at all.

But if she was truly forty meters tall, give or take a few – and if I knew my giantesses by now, she’d be taller than she indicated – then each of the short legs she sported was probably larger than an old redwood tree and being more than a hundred times my weight. That was incredible, so I obviously started talking with Melissa, since I wanted to know more about her. It turned out that her story was rather sad. She had been married with a kid when she started growing up, and since her child was barely four years old, she had had to give him up to his dad when he refused to live with a woman who dwarfed him so much.

It seemed she wanted someone to spend some quality time with her, to still make her feel loveable and loved. Honestly I was really super angry with her ex. What kind of bastard would ditch a woman going through such a monumental change? And their kid, he probably felt terrible, not seeing his mommy when he may have been terrified by her growing so much in the first place. So, obviously, I volunteered for the task, hoping to try and help her repair her broken heart, if only a little. It was the least I could do, really.

We talked for about a week before she wanted to meet me. It was a little surprising at first because I had expected either a much shorter discussion if she just wanted some sex, or a far longer one if she didn’t want to be burned. But it seemed that she was taking her change relatively well, far better than she would have had before her growth, according to her. I couldn’t really be the judge of it, but Melissa – it was her name – certainly seemed, if not cheerful, at least relatively optimistic about her future.

When we met up, it was at her place. It was still being built but she had ushered the workers out for the day. Her reasoning had been that if things got a little heated, they’d have some more work the next day, and as far as she could tell, nobody dared talk back to her now that she was forty meters tall. Anyway, when I walked into her still far from finished abode, I was greeted by a stunning spectacle: Melissa was sitting on the ground, leg sprayed and entirely naked. She grinned at me when she noticed my stupor – I hadn’t been expecting that from her to be honest!

“I know, I know. That’s really not classy. But we’re both here for that, aren’t we? I need a good, long, sex session Derek” she explained to me, almost timidly, which contradicted with the sight of a super-heavy body and the way her massive breasts fell almost to her hips as she sat like that. “I want you to crawl into me and love me, Derek. Can you do that for me? I promise I’ll be super gentle and we’ll talk after the act. I always liked talking after sex” she giggled like an innocent schoolgirl as she said that, instead of the naked behemoth she was.

As you probably expected already, I did what I was told. I could lie to you and tell that I tried to convince her that we needed to talk some more; that I wasn’t that kind of guy but…  No, just no. There was no way I’d waste even one second trying to pretend I wasn’t here to enjoy sex with a real giantess. I almost jumped out of my clothes and walked between her legs. Her feet were far taller than most door framed I had ever passed and as I walked past them, the soles collided together, sealing any way out I could have tried to take.

From that angle, her legs were even more massive than I had expected them to be. At least three meters tall, almost as wide, if not more, even firmly planted on the ground. And before me, twenty or so meters away, a dense bush of black hairs covering the entrance of the womanly cave I was meant to crawl into. And above it, a mountain of a woman who was biting her lips and cupping breasts heavier than anything human had the right to be. I wondered if whales weighed as much as those mighty boulders or if they were even lighter than those.

It was a strange sight, to be able to approach a pussy almost as tall as I was, but hidden by a veritable jungle of hair. Its smell hit me like a wave and its warmth also. I felt my dick going full erect and it took a lot of willpower to not start to stroke it just yet. Melissa’s pheromones were so thick I swear I could feel them on my skin. I wasn’t brainwashed because of them but they made me feel a little drunk and extremely horny. If you’d asked me to talk then, it’d have been a really, really, hard task for me. And I wasn’t even that close to her cave.

I gulped when I was but a meter away from it, and while I couldn’t see her face anymore, since it was blocked by her vast belly forming a porch over her pussy, and even above it her tits which were absolutely monstrous from so close. In fact, I stopped for almost a minute, so surprised I was by this sight and the vastness of Melissa. It wasn’t until she gently nudged me forward with a finger taller than I was that I managed to focus on what I had to do. I finally touched her hair and I wasn’t disappointed.

They were black as night and a little rough, I think if I hadn’t been careful caressing this one, I could have scraped my hand! But it was also quite sensitive since she gulped loudly far over me and I swear I could see her tensing everywhere, and even her pussy seemed to become warmer and smellier. I shook my head, trying to focus but it was really hard to do that. I wanted to go beyond this dense jungle of hair and with a great steeling of resolve, I did just that. It was harder than expected because she had a lot of hair down there, it was extremely dense.

It was truly turning into a trek but it seemed that the giantess liked it. She was starting to make little sounds which were obviously due to her arousal and the pleasure she was deriving from what I was doing. I truly found her former husband pathetic and disgusting, since he had given up the opportunity to spend his life with such a behemoth who was clearly in dire need of sex. Suddenly I tripped on some hairs and caught something in my right hand which made Melissa scream so loudly my ears ringed.

I had caught her clitoris somehow. It was absolutely incredible, that thing was almost as big as my head! It was truly a soft ball of warm flesh that reacted to my most minute caresses. Melissa screamed again and again and the smell of her arousal became even more powerful as I gripped it a little and even gently slapped it. I don’t know how she didn’t close her legs on me just yet but she didn’t. In fact, she even had enough of a clear mind to actually growl an order at me, one I was more than happy to oblige.

“Get inside of me Derek! I want to feel you inside of me! I want to have a grown up man, taller than my husband entirely in my pussy! I want to show him what true domination is, so please, be quick about it, I don’t think I’ll be able to control myself much longer!”

“It’s easier said than done!” I yelled as loud as I could. “You’re really something down there, and I couldn’t just pass by that delicious fruit without tasting it” I added, before gently nibbling her clitoris before diving head first into her gawking vagina, which was now opened quite widely, as she shrieked in pure animalistic lust.

It was an otherworldly experience, as you can imagine. A pussy large enough to gulp down a man was something else entirely and in a matter of seconds, I was wholly inside. It was roomy, and I wondered if it had always been so or if her husband had enlarged it somehow – or her growth. Not that it mattered much. The walls were slick with her love juices and warm to the touch. It wasn’t uncomfortably hot here mercifully so I could enjoy my time inside. And enjoy it I did, as I explored her innards.

I enjoyed this place a lot. Perhaps I should have felt afraid that the walls of Melissa’s vagina would close on me, or because of the darkness, her hairs blocking out most of the light, and of course the deeper I went inside of her, the darker it became. But in truth, I enjoyed it a lot. It was a pure fantasy that came true, the likes of which I had talked with Tori, my ex-girlfriend, before we broke up. After some time fooling around and reminiscing about the past, I decided that I wanted to really stimulate the behemoth I was in and searched for her G-spot.

I had enough experience with women to know where to search for it so it didn’t take me more than a few seconds before I spotted it with my fingers. I had to really lift my hands over my head to reach it however, so it wasn’t the most comfortable position. Still I was rewarded by a sudden shift of the ground as I caressed the rougher – almost strawberry-like – texture of the G-spot. Clearly, it worked awesomely to stimulate Melissa and I wondered how long it’d take before she’d start playing with herself if I kept at it. There was only one way to know.

The smell of her was truly intoxicating and it helped me continue my task, even if I really wanted to masturbate or at least have some form of sexual release myself. But for now, it could wait as I caressed and pressed my hands into the G-spot with glee. A roar of pleasure rolled from high above and while I couldn’t see her, I was almost certain she was tensing all over thanks to my efforts and was absolutely closing in on her orgasm. It was awesome to be able to create such a reaction out of a being far larger than myself of course.

I wasn’t ready however for what came next: giant fingers entered Melissa’s pussy and pushed me aside as she started to masturbate wildly. It didn’t even bother me because I meant that I was now free to go deeper, toward her cervix. I had to crawl a little at the end but it was such an incredible opportunity that I didn’t care one bit and in absolute darkness I managed to find my quarry. And I fucked it. It was perhaps dangerous because she could potentially end up pregnant. But I was too lost in the need to mate with her by then to care.

I wouldn’t be able to describe to you what I felt then, as I fucked something which wasn’t meant to be fucked like it did. Absolute darkness, the smell of Melissa’s arousal and my own lust combined to turn this experience into something absolutely otherworldly. I may be going a tad too fast but I can tell you that if some things happened mere weeks after this encounter, perhaps I’d have ended with Melissa only to experience it on a daily basis. It was the absolute fulfillment of all my pent up fantasies and I couldn’t resist it, not even for a moment.

In the end, it took me a relatively short time to cum the first time. But it was only the first of several orgasms for both of us. As I searched for a better position to pleasure myself and Melissa at the same time, I unwittingly settled on her deep spot, as she’d explained to me later on, and it made her cum. I hadn’t been ready for such a tidal wave of flesh. If the conduit of her vagina hadn’t been so narrow where I was, I’d probably been washed away. As it was, I was simply drenched and constricted by her muscles until she relaxed, leaving me gasping for air.

The smell in here was driving me crazy with lust and of course it was even harder to resist it when I took my much needed oxygen. Melissa’s fluids covering me from head to toes were quite the aphrodisiac and the next half hour was something absolutely out of this world. I never had such wild sex, making love to a giantess while she pleasured herself, until finally I stopped, utterly exhausted. I almost drifted to sleep as Melissa's insatiable lust didn’t seem to abate at all. Finally, he felt powerful digits grasping for him and removing him gently from inside of her.

“Well, that was… wild,” she chuckled. “And just so you know, my husband, well, ex-husband now… he was a beast, even taller than you are, really. At least I think he is taller than you, it has become extremely hard to truly gauge the size of normal sized persons since I grew so big… but I’ll be honest, you really made me love it, Derek. So, how about some afterglow talking?” she finished, laying on her back and dropping me on one of her enormous tits.

“That sounds… like an awesome idea” I admitted, panting.

“Wonderful. So you know, I’m not usually that… voracious” she said, and as I looked up at her face she seemed a little embarrassed – but also quite happy with herself. “But ever since I’ve started growing, I had those pent up desires and, well, my husband… he wasn’t too keen to satisfy them, especially once he had to look up to me.”

“You grew fast?” I asked her, wondering how the experience had been for her.

“Yes, I doubled in size in a day at first. I almost stopped around the twelve meters mark, for a week or two, by which my man was already looking quite uncomfortable with me. And then, up to forty two meters tall in three days.”

It was a little mind-blowing to take in. I could understand how a very macho man, who loved to be the tallest, strongest one in the relationship, could find himself unsettled by his formerly petite wife turning into such an impressive colossus. Even I would have probably been a little taken aback by such a deep change in our relationship, if I had been in this man’s shoes. But on the other hand, as I looked at the incredible landscape that her body had become, I was certain I’d actually appreciated the changes, in due time. How couldn’t I when she was so massive, right?

“He had always been my big strong man, you know” she sighed, and I could tell she regretted his absence still, which was only natural, their break up was fairly recent. “He… didn’t take it well that I was the one lifting him now. And our son, he was really confused, he couldn’t understand why Mommy was… was growing” she continued, until her voice broke and she battled off tears and sobs. I squirmed a little on her, hesitating on what to say or do until I made up my mind.

“You’ll have a huge house and plenty of money to have a babysitter at home. Shouldn’t you try to get back your son, at least?”

She sighed and didn’t immediately reply, instead putting one of her hands on her belly. The sole reason I was able to see that was because I had unconsciously moved upward, toward her still erect nipple as we talked. That I hadn’t realized it was a little unsettling but I think neither of us minded it when I sat on the large cushion it offered and enjoyed the sight of her whole body laying out for me. It was truly a blessing to be here, and for the first time, I felt like I needed to find a giantess to build something that would last with her.

“Yeah” she finally said softly, her voice very low, as if she was talking to herself rather than answering me. “I think I won’t just get my son back. I want my husband too, just to teach him a lesson. He’ll be my little bitch and I’ll shove him inside of me whenever I want to. And if he doesn’t like it… well I could always invite you back to some good love making while cucking him!”

A woman scorned is already quite terrible to behold in her revenge, but a giantess? It’s something else entirely. I almost felt bad for her husband, because I was certain she’d do as she had told me. But it excited me, I won’t lie. My dick, sore because of how much it had come inside of her, became erect once more. She noticed it, cooed and lifted one of her fingers toward me. I sprayed my legs open so she could caress it, surprisingly tenderly. I let out a loud moan when she started to make it move gently, and she chuckled.

“Well, you weren’t lying when you said you liked big women” she said, and I could tell she was really getting aroused all over again. “You’re really cute Derek, I almost want to keep you with me… Who would even think about searching you in my privates if you were declared missing? And you’d like that, wouldn’t you honey?” she continued, still caressing my dick tenderly.

“Ah… ye… yes…” I stammered, my head a little cloudy because of her stimulation and my imagination starting to run wild about the possibilities. “I… I’d really like tha –ah-at!”

“That’s adorable” she whispered as she put one of her hands behind my back and laboriously sat back, making me fall into her inviting palm. “Would you be an adorable little morsel and fuck my nipple, Derek? Would you please your huge lover for a day like that? Hum?”

“Yes!” I yelped louder than I wanted, but she had ignited my fire again and I couldn’t resist it. I had been sitting on that nipple and the opportunity to be able to fuck it, properly, would be absolutely awesome. “I… Do you want me to, uh… have a specific position?”

“No, get conformable and don’t worry, my hand will remain there to protect you.”

I was elated and I searched for the best way to please Melissa. At first I suspected that putting my feet on her palm would be the best way to go, but it turned out the creases of her hand made for a poor ground to plant my feet. So instead, I climbed her tit a little, putting my feet on that enormous mass which didn’t even bulge under my – comparatively – insignificant weight, gripped the nipple over its edge and inserted my dick into her milk duct. Immediately, I was rewarded by a low growl of pleasure which pushed me forward.

It surprised me a little but Melissa didn’t touch herself while I mated with her nipple. She seemed to enjoy it tremendously as she moaned softly and her breathing became quicker, but when I looked up, she was only biting her lips and looking at me, enjoying the power they had over me more than anything else I suspect. I was obviously fine with it – how couldn’t I when I loved my women tall and heavy set? I couldn’t deny that there was something incredible in the fact that she had such confidence in her ability to subdue me that she allowed me to do what I was doing.

Finally, after a minute or two, I released my load inside of her and went a little limp, as if the exhaustion of the day was finally catching up with me. However, she didn’t gave me time to really recover before she gently lifted me from her nipple and cradled me in her left hand, while, with the right hand, she lifted her mammoth breast with an ease which belied its size and mind-blowing weigh and started to suck on her nipple. It didn’t take me more than a few seconds to realize she was sucking my cum out of her, since she looked straight at me while doing so.

She moaned a lot louder when she gulped and then let her tit fall back on her. It slapped on her torso with so much force I was almost catapulted out of her hand as the tremor coursed through her body. And the sound! It was as if a bomb had exploded here, but Melissa didn’t seem worse to wear since she used her now freed hand to trace the slow descent of her saliva and the large – for her, almost insignificant – amount of sperm I had deposited inside her nipple and she had sucked out with barely any effort at all.

“Hum, you taste delicious, Derek” she laughed and I blushed a lot. “I really should keep you with me, I’m sure we’d make beautiful babies. Perhaps you even put one in my belly already, didn’t you? I could feel you rutting in me. It was the best sex I ever had, so don’t feel too bad about it. If it’s a boy, I’ll even call it after you” she added winking, leaving me a stuttering mess – I had pondered the possibility of having impregnated some of my other giantess flings, but it was the first time it felt more like a certainty than a possibility and it was the girl bringing this matter on the table. “Oh, you look adorable when you’re worried!”

“I… uh… thanks bu-“

“Don’t worry sweetie, I’ll keep in touch” she cut me off while lowering her hand so I could hop off of it. “Seriously, don’t lose my number Derek. Depending how it’ll go in the next few months, a spot will definitely remain open here” she stated, caressing her bush. “If you’re still single when I call you back… well, you’ve already seen your room!”

“I… yeah, and it was great” I blurted – if she was really thinking what she was saying, I could envision a very sexy future for me. “I’ll keep in touch with you myself. Even if you don’t, you know?”

“Get pregnant?” she laughed as I gestured for a larger belly. “You know, if the baby’s your size, I doubt I’ll even realize I’m pregnant. But we’ll see that in due time. Off you go now, little rascal!” she said, chasing me away gently as she got up, dwarfing me so much that even her gentle tone was enough to make me scamper through her unfinished door.

I went out so fast in fact that I had forgotten my stuff! But just as I realized it, Melissa called me back and then flicked my stuff at me. For her it was clearly a very slow and deliberate way to not throw them too hard or too far away from me, but when her perfect shot landed on me, it was with enough force that I staggered backward and fell on my ass. The naked behemoth laughed so hard she had to grip her door frame and the concrete crumbled like dirt under her powerful digits. She didn’t seem surprised so I guess she had always known she could destroy her own house whenever she fancied it.

“Goodbye Derek! Be careful driving home, I do want to see more of you!” she yelled, waving at me as I got clothed, jumped into my truck and left, waving back at her through the window. “Perhaps I’ll be even taller and you’ll be able to park your car in your room next time!”