Chapter 14:

I stood on the bed butt-naked, just as Jackie demanded. That was becoming a common theme. She demanded, and I carried out her demands.

Two minutes later, she emerged from the bathroom with her luscious blonde hair down. To my utter dismay, she was still wearing her maroon lingerie. She must’ve seen the disappointment in my eyes because she immediately squeezed my cheeks and mocked me, saying, “Awww, is the little guy upset that I’m not naked like he is?”

Standing on the bed, I nodded.

“Don’t worry. I will be naked soon enough, well that is, if you’re strong enough.” She sat down on the bed with her back to me, still almost a head taller than me.

“What do you mean?” I asked.

“Undress me.”

I scoffed. How hard could it be to unhook a bra strap and pull down some panties?

She had me start with her bra, but it was so tight that I could barely budge the hooks from their current position.

“Having trouble back there, Casa Nova?”

I quickly thought of an excuse. “No, no! Just, um, savoring the moment.”

And she didn’t really buy it. “Hmmm, interesting. Well, I’m done savoring, Dessy. Get it off.”

“Ok, ok!”

With all my might, I pulled both straps the opposite way, hoping they would snap off. Again, I failed.

Without warning, her hands shot back and grabbed my hands. She made me take hold of the hooks once again, and with her strength behind me, the bra came off.

She turned around and said, “See that wasn’t so hard, right little guy?”

I said nothing, beholding the glorious sight in front of me. Her breasts were impossibly round and high up on her chest. They were close to the same skin tone as the rest of her body, which made me wonder if she sunbathed in the nude. Her nipples were perfectly symmetrical, assuaging all my fears that she had fake tits. She had all-natural, size Out-of-this-World boobs.

“Can I touch them?” I asked.

“I was waiting for you to do that,” she giggled.

I lightly, and ever so gently touched both of her breasts with my hands. I caressed the top halves of her boobs, getting a feel for their smoothness. I also immediately noticed how fantastically dense and firm they were. I pressed inward with a fair amount of force (for me) and my fingers popped right back up.

I was amazed with how firm her breasts were, even though they were so comfortable to have my face buried in. But what I was truly amazed with was their size. Their size was further put into perspective when my hands were touching them. My palm wasn’t even big enough to cover her nipples, let alone cover the entirety of her breasts. I truly didn’t know any more if this ungodly size imbalance was due to me being so fucking small, or if it was her immensity.

My thoughts weren’t that complex in these moments though. All I could think was, I want to fuck these tits so bad.

Seeing that I was in another one of my trademark boobie trances, Jackie grasped my chin and turned my attention to her face.

“I’m glad you like my boobs, Desmond. But if you stare at them all night, we’re not going to get anywhere.”

Embarrassed, I apologized, “Right. Sorry.”

“No need to apologize. I’ll turn around again so you can focus a little more.”

She turned around, but I could still see the outer curves of her boobs peeking out from her toned, muscly back.

“Now, I want you to take off my panties.” She stood up, giving me a world class view of her ass. It was respectable. It wasn’t even close to as enormous as Audrey’s. But it was tight, and oh so beautiful.

Before I could lose myself in the sight before me, I hopped down off the bed, cracked my knuckles and readied myself. Her panties looked form-fitting, which wouldn’t make them easy to just pull off. I wondered if she was wearing undergarments that were a size too small, just to make it difficult for me to pull them off.

About as tall as her butt, I actually had to reach upwards to pull down her panties. I slid my hands down the back, grabbed a handful of the fabric and yanked downwards. I didn’t think anything could be harder than taking off Jackie’s bra; I was wrong.

As soon as I pulled, I lost grip of the fabric, and my hands were trapped between the fabric of her panties and her ass. And I don’t mean ‘trapped’ in the superficial sense. No, I was stuck like an animal lured into a trap with a piece of watermelon. In this case the ‘watermelon’ was her ass and the ‘trap’ was her panties.

To my chagrin, Jackie took great pleasure in this. She began spinning around the room with my hands halfway down her panties. I would’ve expected to come free, but I stayed firmly where I was, spinning around with her. I never thought being intimate with Jackie would resemble going on a carnival ride.

“Are you sure you’re tall enough for this ride?” asked Jackie as she spun me around. Evidently, she saw the parallel to a ride just like I did.

“I fucking hope so.”

Sensing I was getting a bit annoyed, she finally stopped twirling around the room, which gave me a moment to gather myself. My hands were still stuck where they were until she conveniently pulled them out.

“Here, we’ll do this together.”

Just like with the bra, she took her hands in mine, and guided me in taking off her remaining undergarment. It was amazing how much easier it got when I had her strength to work with.

She slid her panties down painfully slow, keeping her gash out of view for as long as humanly possible. And I knew it wasn’t because she was shy. She was a tease. And I loved that.

Then, we hit the point of no return. A simple shift of her legs inward would cause her panties to drop, and in turn, her pussy would come into view.

Suddenly, she did just that. Her panties were in heap around her feet, and her pussy was right there staring back at me, glistening with pre-wetness. I wasn’t the only one in eager anticipation.

From this moment on, there was no more talking. I started slow and found the clit with my finger. Her emphatic moans confirmed my discovery. After only half a minute, she begged me to use my tongue. With both of us standing upright, I only had to bend down a few inches to stick my tongue in. I slowly lapped at her pussy, until I could feel her growing impatience. I quickened the pace ever so slightly, and she squeaked a moan of absolute pleasure. Just that squeak alone caused me to start leaking.

Before I knew it, my tongue was getting exhausted. But she kept saying “faster, faster, faster!” Each time, I was less confident I could quicken my pace any more. Unsatisfied, she grabbed my head, and shoved my face nose deep into her vagina.

“Ohhh!” she yelped.

I tried to tell her that I couldn’t breathe, but it was no use. She was in the clouds. This was when I went all out on her clit, stabbing it with the tip of my tongue, slapping it, sucking it. I needed her to orgasm now, or else I was in danger of choking on her damn fluids.

“Oh, oh, ooooh! Desmond! You’re…amazing!” I heard her saying. And then, even more forcefully than before, she said, “Keep fucking going!”

I went in harder than ever, not knowing how long I could keep up this insane pace. My vision was blurring, and I was getting massively lightheaded. With all the strength I had, I rotated my head so I could suck in some air. Unfortunately, that hindered my ability to lick her G-spot. And she noticed.

“Did I say stop?!”

Without getting even a sip of air into my lungs, I was thrust back into the wet cavern that was my girlfriend’s pussy.

“I…can’t…BREATHE!” I screamed.

“Dessy, I’m so close! Just keep going! Fuuuck…”

I didn’t know if she didn’t hear what I said, or if she didn’t care, but either way she wasn’t letting me out until I licked her to orgasm.

Over the next thirty seconds, several things occurred. First, my tongue cramped up; something I didn’t think was possible. But I guess with overuse, anything can cramp. Second, after my tongue was out of commission, I just started grinding my face into her pussy. Up and down, side to side, in circles, quick movements, slow methodical movements. I did whatever got the best response.

“Oh Dessy! Ohhh, that’s so…fucking good! Oh, oh, OHH!” was her response.

Third, my air was quickly running out. When I began to see stars, I knew my window of staying conscious was closing fast. I kept up the face grinding, hoping the slow leaking of her juices would finally transition into the waterfall I was trying so hard to coax out.

Fourth, my head felt like it was detached from body. I forgot that I had arms, legs and a torso. It was like I was only a mouth with a respiratory system. It was the first out-of-body experience I’d ever had.

Fifth, she screamed louder than I’d ever heard her scream. It was primal and vulnerable at the same time. And a moment later, the dam exploded, and the waterfall I was yearning for finally came. She exploded into orgasm just as I was about to give up and fall to the ground in exhaustion. 

She squirted, so my face was instantly drenched in Jackie’s juices. She finally let my head out of her pussy for a moment, and I gasped for air, sucking in as much as I could. It turned out it was good decision, because she shoved me right back in during mid-orgasm.

“Lick me! Lick me! Oh, Dessy! Fucking lick me!”

Back in her pussy, I had no choice but to swallow her juices. Even still, I couldn’t swallow fast enough, so much of it leaked out the sides of my mouth and down my shoulders. The fluid came out so fast and in so much volume that I couldn’t even get my tongue out of my mouth to lick her.

“I said…lick me! What the hell are you doing!”

She tilted my head up to look up at her. The sight was nothing short of fantastical. Her belly-button smiled down at me. It was an innie. She was the only girl gorgeous enough that I could get lost in the beauty of her belly button. My eyes climbed up her golden waist, tanned and toned to perfection. I could see droplets of her juices on the undersides of her breasts, demonstrating the forcefulness of her orgasm. I could see her face from the eyes up. Her tits were so huge that I couldn’t see the majority of her face, which almost made me sad knowing how beautiful the rest of her was. Her ocean-blue eyes lasered down on me, and my euphoria was broken when I met her gaze. My overwhelming sense of jubilation was replaced by a growing fear of what she was going to do for directly disobeying her directive to lick her.

The fear I had for Jackie made me want to talk her down from whatever punishment she was considering for me. I opened my mouth and tried to speak, but all that came out was a loud wail and a flood of tears.

I collapsed and began crying into the puddle of Jackie’s juices that had formed on the ground. I uncontrollably gasped and wept as I retreated into the fetal position. I closed my eyes and awaited Jackie’s wrath.

But it never came.

She sat her naked ass next to me and ran her hands through my wet and sticky hair.

“I’m sorry I pushed you too hard, Dessy. I’m so so sorry. I didn’t care about your sexual inexperience. All I wanted to do was get off, and I wasn’t thinking about what you could handle. Clearly, we’re going to have to build you up.”

Still sobbing, I managed to get out, “Build…me…up?”

“Yes. We’re going to have to train you in eating me out. And as you get smaller, the training will have to get more rigorous.”

“More…rigorous?”

“Yes, little guy. As you inevitably shrink down further, my pussy will be bigger, stronger, more intimidating to you. You’re going to have to build up your endurance. Eventually, you’re going to have to be able to hold your breath for minutes on end.”

“Minutes?” I was hyperventilating at this point.

She made me look at her, getting very close to me. “Relax, Dessy! That’s way down the line. You don’t have to worry about holding your breath for that long yet. Only when you get small enough to, you know…well, fit inside me.”

Still breathing fast, I was beginning to freak out. This was too much for me. I could handle being this height or even a little smaller, but being small enough to be a literal dildo was too much.

“Jackie, I can be this height. Or even a little smaller. But this is going too fast. I can’t—I can’t do this!”

She lifted me into her lap and smooshed her tits around my body. My dick twitched when she closed me into this boob sandwich.

“Desmond, I know you’re scared. I would be too if I was in your position. But don’t deny your desires. I can feel your cock poking into my stomach right now. And I bet you feel smaller than ever right now. Stuck in between my boobs. You think there’s a correlation there? When I make you feel small, you love it. Admit it.”

My eyes darted away sheepishly.

“You don’t have to say anything, Dessy. I know you love being my shrunken little boyfriend. But tell me, what are you scared of? I want to know.”

I looked back up at her and tried to find a way to say what I wanted to say.

“I- I—just,” I stammered, “I like where I’m at now. I don’t want to shrink down to a size where I can’t do normal things. I like being, uh, dominated by you. I’m afraid that if I get too small, I won’t ever be able to have a ordinary life again.”

Jackie thought over my answer for a second. She looked back down at me, jostled me in her tits, and kissed me on the forehead.

“I adore you, little guy. But I don’t buy that explanation. An ordinary person would’ve gone home with his mother to cure his shrinking disease. Instead, you stayed with me, which was against what any sane person would’ve advised you to do. You aren’t looking for an ordinary life, Dessy. You’re looking for an extraordinary life. And what’s more extraordinary than having a giantess girlfriend?”

I couldn’t refute a single thing she said because it all rang true to me. I did want this. I did want to shrink away into Jackie’s arms. I did want to get shoved into her pussy. I did want to use her boobs as a trampoline. I did want to climb locks of her hair like they were vines. But I was still confused.

“Then why am I having second thoughts?” I asked her.

“I think you’re scared. I think you’re scared that if your life changes that it will get worse. I can assure you, Dessy, you’ll love being small.”

“How do you know? How do you actually know for sure?”

She squeezed my cheeks lovingly, muzzling me in the process.

“Do you trust me?”

I nodded.

“Shrinking will be the best thing that ever happened to you. My body will be your vacation getaway. Your oasis. Your heaven. Because when you get small enough, you’ll always be with me. You won’t have to worry your pretty little head about anything anymore. All you’ll have to focus on is your unquenchable sexual desire for me.”

That sounded nice. Actually, it sounded better than nice. It sounded like a dream: the best wet dream in the world. Only, it would be real. And there would likely be no room for anything else. Friends, family, and school would become distant memories.

“Jackie, that sounds like a dream.”

“You say that like it’s a bad thing,” she said.

“It’s not a bad thing. I’ve been daydreaming about being tiny every single day. But it’s a dream. Are dreams supposed to be real?”

“But if it’s your dream, and there’s a way to achieve it, why wouldn’t you?”

“I don’t know, Jackie. I just don’t feel…ready. Do you know what I mean?”

“Yes. I do. If you’re not ready, we’ll go as slow as you want. We’ll fit you with a chastity belt, and when you’re ready to fuck me and shrink, I’ll let you out.”

Jackie proposed the only real solution to my fears, but it just seemed hollow. I didn’t want to shrink, but I also didn’t want to be sexually frustrated.

“Jackie, I don’t want to do that though,” I whined.

“Nobody does, little guy. But that’s the only way you’re going to delay the shrinking process, and you know that. If you really feel that you’re not ready to shrink any more, you’re going to need to stop having orgasms.”

“I’m stuck between a rock and a hard place,” I said.

“You’re actually stuck between two giant boobs, but…”

“Yes, that too. That’s where I’d rather be stuck.”

Jackie let out an exasperated sigh. And for good reason. She was expecting to have a night of sexy fun, and I was derailing that. I was waffling between two hard choices, and that didn’t exactly make for an entertaining night.

“Can you make the decision for me?” I asked, “Sex or chastity. I can’t fucking choose.”

“As crazy as this may sound coming from me, I feel like this is something you have to decide for yourself, Dessy.”

“Hey, listen, I know I’m boring you, but—”

“No, you haven’t been boring me, Dessy! I know this is hard for you. I just wanted to tell you that. Now what were you saying?”

“I was saying that we could make this interesting. Let’s play poker. If I win, I choose what I do. If you win, the choice is yours. And I promise I’ll stand by whatever you decide.”

She lifted me out of her tits and sat me back down next to her on the ground.

“That is certainly an interesting idea. But I don’t know, Dessy. Are you sure you want to play poker with me? I’m pretty good.”

“Hey, you know what? I changed my mind. We can play poker another night. Tonight’s special. Let’s get in the bed.” I made a snap decision.

“Are you saying you want to…?” she trailed off.

“Yeah.”

“Right now?”

“Yeah.”

“Right here?”

“I’m starting to wonder who’s more excited about this,” I joked.

She stood up to her full height and pulled me into her body. She let out moans of pleasure and fulfillment.

“I thought I was the tease here,” she said, “but you really had me thinking that we weren’t going to fuck at all tonight. You little tease, you!”

She flipped me upside down, held me by my ankles, and dangled me above the bed.

“Does it turn you on that you could never hold me like this in a million years?”

“Yes. So much, goddess,” I slurred, staring at her navel upside down.

“Does it turn you on that my fingers can go around your ankle almost twice over, but your fingers wouldn’t even go around my ankle?”

“Yes. Yes!”

“Does it turn you on that your legs are ten times weaker than just one of my arms?”

“Yes! And if you keep saying all this stuff, I’m gonna cum!”

“Weak little boy. He hangs on his goddess’s every last word. And if she says just the right thing, she can make him cream himself. Oh, boo hoo!”

“Oh my god, Jackie. You’re so fucking hot. You’re gonna make me shrink down to nothing!”

“Let’s get started with that then, shall we?”

She dropped me headfirst on the king bed, and then she crawled up onto it seductively, like she was a predator and I was her prey. As she got closer and closer, I found myself lowering down, cowering in front of her, until I was lying flat on my back and she was on all fours on top of me. Her tits hung from her chest, swaying inches from my nose.

With no warning, she dropped herself right onto me. Her boobs came down right on my head. The way they bounced and squished and conformed to the shape of my body drove me nuts with angsty lust. With her giant orbs of womanly flesh right in my face, I couldn’t help but imagine sliding my dick between them. They were so giant, in fact, that they were in Jackie’s face too. I was beginning to wonder if her boobs were always this big. I remember noticing her boobs the first time I met her, but I never remembered her boobs being this big.

“If you want to fuck me, I think you’re going to have to be on top. I don’t want to kill you with my boobies.”

She raised herself just enough, so I could talk and so she could tease me with her boobs.

“Wouldn’t be the worst way to die,” I said.

“No, it wouldn’t,” she said as she rolled over on her back next to me, “Take me, my little stud.”

With no more second thoughts, I got up and started rubbing my dick on her pussy. Unable to kiss her on the lips when I was going down on her, I kissed her boobs instead. They tasted of sweat and vaginal juices, and I loved it. When kissing wasn’t enough, I transitioned to licking them. She seemed to like that, but she wanted more.

“I want you inside me, Dessy.”

Suddenly realizing that I didn’t have any protection, I asked her if she had condoms.

“I’m on birth control. Just go!”

I shouldn’t have taken her word for it, but I was already so hopped up on pheromones and sexual angst that I would’ve believed any excuse she offered up.

I grabbed my cock and positioned it right above her pussy. I slid in and a moan of satisfaction immediately escaped my lips. Her pussy hugged my cock tighter and tighter as I plunged it deeper.

“Oh god,” I exhaled heavily. Having sex for my first time, I was overcome with how good it felt. When I was confident that I wouldn’t immediately explode if I moved the wrong way, I wrapped my arms around her thighs and quickened the pace of my thrusts into her.

“Don’t go too fast,” she said.

I slowed down again, but a few moments later, I found myself speeding up.

“Dessy, you don’t have to go fast right from the start. Build up to it.”

“O-Ok, J-Jackie…”

“Are you gonna cum?”

“Maaaybe,” I said.

“Let it happen.”

“Are y-you…close?” I asked.

There was a palpable hesitation from her. And her answer wasn’t encouraging.

“It’s been…only two minutes,” she said.

No need to be so condescending, I thought.

I tried to slow down to a more rhythmic pace to last a little bit longer for her. Lasting any longer was super difficult considering my present circumstances. The vastness of the woman I was trying to be intimate with, was mesmerizing to say the least. Her legs stretched all the way to the end of the bed, and her head was all the way up at the headboard. She was easily five times heavier than me, and her boobs alone were likely a fourth of my entire body weight. She belittled me simply by existing. No words had to be spoken. It was innate.

“You’re so huge. I can’t believe it,” I babbled as I fucked her.

“You’re so tiny. And I’m starting to believe it.”

I was ready to cum. I wanted to explode inside her. So, I got her to repeat herself.

“Say that again. Say I’m tiny. Tell me how fucking small I am!”

She obliged, “Dessy, you are a shrimp. So tiny. So itty bitty. So, so small.”

At this point, I was practically stabbing her with my dick. I wasn’t trying to last anymore. I was reaching for ecstasy. She, on the other hand, was rooting for me to shrink.

“Shrink for me, Dessy. Shrink! I want to watch you dwindle into my little, itty bitty, teensy-weensy, tiny little plaything! Shrink! Shrink!”

I no longer needed incentives to cum and in turn, shrink. But it wasn’t really about me, I suspected. Getting her to tell me how small I was, turned me on. Her raving about how small I was about to get, turned her on.

Unable to hold on any longer, I shot my load straight up her pussy. Jackie squealed with satisfaction and my orgasm was stronger than anything I’d ever felt, reverberating throughout my entire body. Every muscle I had tensed up, and I collapsed into her, laying my face on her stomach. I enjoyed complete bliss for a good while, as my face bobbed up and down with every rise and fall of her diaphragm. My bliss though, was soon replaced with a nervous anticipation for what inevitably came next.

“That was good, Dessy. Really good. I got so hot near the end. I just can’t wait to see you get smaller.”

Still recovering from my earth-shattering orgasm, I just laid there trying to catch my breath. But then, an annoying thought kept poking at me from the periphery. I was about to literally shrink and get weaker in my girlfriend’s arms, but as a man, I was still concerned about my sexual prowess. I wanted to know if it was as good for her as it was for me.

“Did you, um, cum too?”

“I got really close, Dessy. Really close. It felt amazing, don’t worry about it.”

“Damn it,” I whispered to myself inaudibly.

Jackie got off the bed and beckoned me to join her. She was standing upright.

“I just wanna lay here,” I whined.

“Well, don’t you want to see what it’s like to shrink right in front of me? I bet that’s one of your little fantasies, Dessy.”

“Yeah, but I pass out every time I shrink.”

“Maybe it won’t happen this time. But I’ll hold you just in case.”

I rolled off the bed onto my feet and stood in front of Jackie. At that moment, I was exactly level with her hip. Not for much longer though. She placed her hands on my deltoids and squeezed a bit, so in case I passed out, I wouldn’t crumple to the ground.

“How much do you think you’re gonna shrink, Dessy poo?”

What kind of a question is that?

I mustered up a response anyway. “I don’t know, what do you think?”

“Come on, party pooper! You wanted to make this fun before. Here’s my idea. If I guess closer, then you will have to cook me dinner one night this week.”

“What?! That’s nuts! I’m already too small to do that with those giant counters in your kitchen,” I protested.

“Then you better guess right! Because if you do, you avoid chef duties, and you get to fuck my tits next time.”

My mouth hung open. It was like she read my mind for the past hour. All I wanted to do get my skinny little dick in between her heaving breasts.

“Oh yes, Desmond. I picked up on the fact that you haven’t been able to keep your eyes off my magnificent tits. You thought I didn’t notice?”

Not hearing a word she said, I just looked straight up at the undersides of her breasts. I imagined her squeezing her tits around my dick as I just plowed them back and forth. I imagined her boobs soaking with lube, bouncing as I did my thing. And I imagined shooting a load right onto her neck, drenching her in the process.

She snapped her fingers in front of my face, whipping me back into reality.

“So tit boy, what’s your guess? How many inches do you think are evaporate into thin air, never to be seen again?”

She truly had a way with words. The way in which she described me shrinking struck deep at my heart. The idea of inches evaporating into the void, never to be seen again was terrifying. Nonetheless, I swallowed back my terror for the moment and offered up a guess. It was the highest number I was slightly comfortable with.

“Five inches.”

Jackie chuckled, presumably because she thought I was wrong.

“That’s all? Nah, I think it’s gonna be way more than that. I think you’re about to lose a whole foot.”

“No way.” I shook my head in disbelief.

“I guess we’ll see who’s right in a moment,” she said with a wry grin.

I felt my stomach lurch, but this was unlike anything I’d ever felt before. If I had to describe it, it was like falling on one of those drop towers they have at boardwalks. Except I wasn’t on a ride, and I wasn’t anticipating any drop. If Jackie hadn’t been holding me up, I most certainly would’ve fell from the sheer force of whatever had hit me.

“Oh my god! You’re getting smaller! Right in front of me! This is just…amazing!” she shouted in a giddy outburst.

I was so preoccupied with the aftermath of the incredible falling sensation I’d just had that I didn’t even notice. Then, I looked. I couldn’t see anything different. Then, I got the falling sensation again. This time, I was paying attention, and I saw Jackie’s body rise up in height. One second, my shoulders were above her crotch and the second, they were perfectly level.

“There it was again!” she said, “Did you see that?”

“I felt it—whoah!”

The lurching feeling came once more, a feeling I knew now was indicative of me shrinking further. I watched as I got closer and closer to the floor, and Jackie’s face went further and further up. I stared intently as I slowly got shorter than even her legs. I shrank and shrank and shrank until I was staring right into the middle of her thick, meaty thigh. A thigh, by the way, that was the same width as my shoulders.

In fact, I was so short now, that Jackie had to bend down into almost an “L” shape just to keep her hands on the sides of my shoulders. 

“Your legs…”

“What are you tryin’ to say, little guy? What’s the matter? Tall girl got your tongue?”

She was partly right. Her the beauty and utter massiveness of her leg got my tongue. And it was just one leg that I was staring at in awe. There was still another leg that I would have to handle. At this point, I was so small that her legs felt like they were full-fledged person. Just a single one of her legs would be an adequate wrestling partner, and it would be a tough match too.

“You’re so beautiful, Jackie.” I looked up at her.

“And you mister, are so handsome.”

In a moment of pure adoration, I inched forward and hugged her. Well, I hugged her leg. That was the best I could do now. And even my best was quite pathetic; I couldn’t even wrap my arms fully around the entire diameter of her thigh. I desperately squeezed and stretched what little muscles I had left, but I didn’t even come close. I started pouting and whining, realizing I wasn’t even big enough to hug a girl’s leg.

“Awww, you’re so cute when you pout.” She peeled me off her leg like I was a child clinging to her and hoisted me up onto her hip with one arm, with my face resting on her boob. “Are you sad that you can’t reach around my leg?”

Unable to look at her, I nodded sheepishly.

“Let me tell you something,” she said, “You are good enough. You’re good and handsome and funny at any size. In fact, you get even more handsome and cute as you shrink. There’s no need to feel inadequate, Dessy. I love you at any size.”

She loves me? I thought.

I panicked. I didn’t know what to say to that. I knew what I felt in my core, but I didn’t know if I should tell her my deepest emotions.

But then, I scolded myself internally. I couldn’t lie to her.

I raised my head over my boob and looked her in the eyes, “I…love you too, Jackie. At any size.”

Her face softened and her cheeks flushed red with hot passion. Her smile melted my heart, and she pulled me over and laid me stomach-down on top of her boobs.

“Desmond, you’re gonna make me cry,” her voice cracked.

I panicked. “Why?! Did I say something wrong? I’m sorry!”

She sniffled and wiped a tear from the corner of her eye. Then, she laughed.

“No, no, no! Dessy, you just made me the happiest girl in the world! I can’t even describe how happy I am to know that you love me.”

She cradled my head and brought me to her lips. One thing I noticed immediately was that her lips felt substantially larger and thicker than ever before. One of her lips was equivalent to both of mine. Kissing Jackie was an all-encompassing experience that got me in the mood every time without fail. The way her tongue just filled my mouth always made my dick shoot up. And that was why after several minutes of the hottest make-out session in my life, I had to pull away.

“You’re gonna make me cum again, Jackie. Please, have mercy on me,” I breathed heavily.

“Do you want to cum again for me, Dessy?”

She was asking dangerous questions, because if she was persistent enough, there was no doubt that she could get me to cave.

“Not yet. Please don’t be disappointed. I know that you love it when I shrink right in front of you.”

“I do love it,” Jackie said, “But I want us to enjoy it together. If you’re not ready, my love, you’re not ready. I won’t ask again.”

She brought me in for another peck on the lips, and then squeezed my butt. I yelped, not in pain, but in surprise. But I immediately liked her new expression of intimacy.

“I wish I could grab your butt,” I said.

“Do you want to?”

“Oh, more than anything.”

“You’re quite short now, we’ll just have to see if you’re tall enough get a good handful.”

She put me back down to the floor and turned around, presenting her ass in its full glory. My head came to the underside of her ass cheeks now, a fact that Jackie squealed in laughter about.

“Go on, Dessy. Squeeze it. Feel it. Get lost in it.”

I reached up straight up as high as I could and was pleasantly surprised with my range. I took my hand and gave her left butt cheek a playful slap.

“Oooh, that a hurt a little, Dessy,” she said.

“Really?” I asked, excited that I perhaps still had some untapped strength.

“If by ‘hurt’ you mean it felt like a toddler swatting me, then yes.”

She picked and chose when she wanted to be nice and when she wanted to be mean. Right now, ‘mean’ was winning the night.

Amazingly though, her ass was that amazingly perfect that I was able to ignore her mean-spirited gibe. I began massaging her butt, kneading into the soft flesh like it was dough. I was so enamored with her ass and so frustrated that I couldn’t stick my whole face into it, that I climbed her leg like it was a pole and clung to her as I rubbed my face all over every crevice of her behind (every crevice that I could reach, mind you. I had climbed up her body on the left side, so her right side pretty much off-limits).

My face was now drenched her sweat, her vaginal juices, and my own sweat. And I loved it. I loved the feeling of being soaked in her bodily fluids. I loved the smell that constantly worked its way into my nose. I was intoxicated by her very presence.

“You are like a little monkey. Climbing me like a tree,” she said as I dove face deep into her butt crack.

Then she said something that genuinely shocked me. She said, “Let go of my body, Dessy, and stick your face all the way into my butt. As deep as you can go.”

I was nervous of falling, but I did exactly as she told me. I burrowed my face as deep as I could possibly go, which was quite deep actually. My head totally disappeared in her ass, and all that was left hanging out was my body from the neck down.

All muffled, I heard her say, “Now let go!”

I let go, just like she said, but fully expecting to fall to the ground. Not so. I stayed right where I was. The pressure on my head increased threefold because Jackie was clenching her butt to keep me from falling.

I hung there, totally helpless and unable to move. If I tried to escape, I would likely just tire myself out and lose consciousness in seconds. So, I remained motionless, focused on my breathing and enjoyed being neck deep inside the ass of the woman I loved.

I realized that this sexual experience was unlike anything any other guy would ever experience. Nearly choking on a girl’s pussy juices and hanging out of a girl’s butt was something no guy, to my knowledge, had ever truly experienced. And in that sense, I was happier than ever before. In a way, I was special.

All these thoughts occurred in a matter of several seconds. Specifically, they were the few seconds before I passed out.

I woke up lying flat on the bed, and I opened my eyes to see Jackie looking down on me with her face stricken with worry.

“Are you ok?” she asked.

“Yeah, I’m more than fine, actually. How many guys can say they’ve passed out with their face buried in their girlfriend’s ass. Not many.”

She laughed, locks of her hair bouncing from around her ear and falling down to graze my face. “That’s true, Dessy.”

“You know, I just want you to know that you beat me to it,” I said.

She squinted in confusion, “Beat you to what?”

“Telling me how you felt. Tonight, was going to be the night that I told you, well, that I loved you. I thought about it for such a long time, obsessing over how I should tell you. And then you just, said it first. I really want you to know that I didn’t say ‘I love you’ because you said it first. I said it back because I really do love you.”

She smiled warmly and her eyes were wet, “Dessy, you’re gonna make me cry again.”

“Give me a hug, Jackie.”

She lifted me off the bed with the strength of four running backs, and nearly squeezed me into a paste.

“I love you Desmond! I love you so much!”

“I…love…you…too,” I croaked under the pressure of her arms.

Thankfully, she eventually calmed down and placed me back on the bed. She crawled up next to me and laid down. We both stared up at the ceiling, knowing that if we gazed into one another’s eyes for too long, I would end up even smaller. Then, all of a sudden, she said, “The night is young, Dessy. Should we get something to drink?”

“Like what,” I asked.

“Like vodka,” she said.

Knowing I would regret what came next, I still said, “Yeah. Some vodka would be good.”

“I knew you would be down to get frisky with me, Dessy poo. Let me call down to the front desk, and we’ll have it in no time.”

Our night of sexy fun had just begun.