Squashed by Shemale Amazon (Part 1)

**Disclaimer: The following is based on real sessions I've had with Amazon Ashley. Some details and the plot are embellished for story's sake, but the important stuff is all accurate.***

I approached the hotel hallway and looked for the arrow pointing towards room #419. I had never given a self defense lesson in a hotel room so I was sort of anxious and suspicious of their motive. This perspective client seemed nice enough over the phone. Ashley was her name. She said she was a dancer who wanted to learn some moves to defend herself from the seedy patrons at closing time should the need arise.

I strolled down the hallway and found the right room, giving a little knock on the door. Ashley opened the door and what I saw forced me to confront every urge I had to run. She was a giantess. She made no mention of being 6'7" and 300+ lbs, not to mention in her wedge heels she stood well over 7 feet tall, dwarfing my 5'10". I was in good shape but slim, and pure physics and geometry told me this was going to be a near-impossible feat: Teaching self defense moves to someone literally twice my size.

"Hi I'm Ashley," she said softly, extending her hand out, or rather down to me. I was speechless for 10 seconds, which felt like an hour, before finally responding "Alex...n-nice to to meet you..."

She giggled. "Don't let me size fool you, I am a giant pushover. I guarantee you are a stronger than me." She was right about the "giant" part, but likely very wrong about the rest.

She was wearing black spandex shorts which were stretched to the breaking point by her enormous, round ass, and a white sports bra which was similarly struggling to contain her massive breasts, and contrasted with her smooth brown skin. She moved gracefully and almost seductively, which was probably just natural for her while sporting that extraordinary curvature. My gawking was not lost at her as smiled at me, her beautiful brown eyes smiling down on me mischievously.

“You’re a little cutie, I can’t wait to learn some moves so I might have my way with you,” she cooed. The irony was not lost on me that not only did I have virtually no shot to demonstrate my ability to fight off an attacker, but also that my instruction might also lead to my own demise. I was wearing gym material, a snug dry fit which hugged my lean upper body and gym shorts.

“I suppose the best place to start would be assessing your abilities. Let’s imagine I am an attacker and you want to neutralize me, what would you do?” I asked, suddenly realizing the implications of my question.

The comical size difference re-registered as she towered over me, my eyes staring directly at her stomach, her breasts hovering above my head. One of her thighs was literally larger than my torso.

“I’m not sure really. I guess you would need to show me,” she responded.

“Ok, if I wanted to take you down…” I said, honestly clueless as to how I could do that.

I assumed a grapplers stance and reached out in an attempt to grab her wrists but she swiped them away. This told me she either knowingly or instinctively already knew the cardinal rule of grappling, not letting your opponent gain control by controlling the wrists. Not a good sign for me.

I tried to lock up her up again but she pulled away and grabbed me into a head lock. Although her curves indicated some softness and a layer of fat, once she applied pressure it was solid. My face was smashed into her skin and I could not squeeze out or breathe very well.

“Hmm maybe I should be the one teaching you the lesson,” she pondered, ruffling my hair with her free hand.

“Ok you got me, you can let go” I muffled into the side of her torso.

She released but then walked me back into the wall, pushing her large hand into me by my sternum.

“I’m very interested to see what’s under this little shirt of yours,” she said while rubbing suggestively on my abdomen.

“We, er…I really…I really shouldn’t,”

“Looks to me like you might not have much to say in the matter, Alex.”

“This, we shouldn’t” I protested, but she cut me off and wrapped her hand around my mouth.

“Ssshhh,” she said, bringing her large leg up menacingly between my legs and into my groin, putting pressure on my manhood while lightly rubbing her leg against it.

The 7-footer had no problem keeping me pinned against the wall, her hand smothering my audible refusals.

“Let’s see what’s going on with this tight little body of yours,” she said, snapping the band on my gym shorts. As she did she got a peak of my bright blue bikini briefs which, at this point, despite my insistence against the situation, were starting to become snug as her thigh grinding began to have it’s desired effect.

“I bet you’d like to see this without these spandex in the way,” she gestured towards her behind, turning around and pressing it into me. Seeings how I was basically a midget compared to her, her posterior was pinning me to the wall by my chest!
I was never particularly attracted to larger women in fact. I had never dated a girl taller than 5’3”, yet here I was being held captive by a girl near two feet taller than that, and despite wishing I could escape my dick was growing hard in betrayal. She reached behind and pulled my shirt up, then turned around and pulled it over my head.

“Mmmm, I like that,” she whispered, rubbing my skinny abs.

“Ok I should probably get going, no charge” I quivered as I tried to walk away, but she grabbed my throat and threw me back against the wall.

“Actually you’re going to pay me,” Ashley growled, “but first I am going to teach you a few things since you weren’t able to demonstrate any skills.

Great, a robbery. I should have known. I realized my wallet and phone were on the other side of the room, so calling the police was out of the question. Even if I could get over there the giantess would pounce on me before I had a chance to dial.

Suddenly she wrapped her hand around my face with one hand and slapped a claw on my balls, eliciting a whimper.

“Here’s the deal, Alex. I charge guys for doing what I’m about to do you, but since you’re a sexy little guy I’m going to give you a discount. We are going to do a little bedroom wrestling. These walls are thick and there is no one in the rooms next door so no one is going to hear you. If you make it out alive I may reward you,” and she winked as she said the last part.

I was in pure terror now, starting to wonder about my own mortality.

“You should be smart enough to see how helpless you are. I am 6 feet 7 inches tall and weigh 330 pounds. There is no way for you to escape unless I let you. So I suggest you lose the shorts and let me see those cute little briefs.”

She was absolutely right, and I realized my only option was to comply and indulge in her sadistic demands, whatever those may be. I dropped my shorts and stepped out of them, now virtually naked except for the superman blue bikini briefs. After eyeing me up and nodding in approval, she pulled down her spandex to reveal a black cotton thong that disappeared into her impossibly large brown ass. She kicked off her heels bringing her height down to breast level for my eyes.

“Ok let’s see what you got little man,” she said.

I figured my best strategy would just be defensive and try to keep from being trapped underneath her. A sound strategy, if only I wasn’t dealing with a person almost a foot taller and over 150 lbs heavier than myself.

We locked arms and she snaked her arms through me, wrapping me up in a belly-to-belly bearhug and lifting me effortlessly off the ground. I grunted as she swung my flailing body left and right, my feet dangling more than a foot off the ground. After shaking me to and fro she whipped me onto the bed. I tried to scurry off of it but pounced onto my back, forcing me to collapse from the weight and force. She climbed up and sat on my upper back. Something felt odd on my neck as I felt the cotton of her thong poking me. Oh my God…no wonder she’s so big…she’s a man! I tried to stifle this mortifying realizing, fearing it won’t only anger her, or him? Whatever, I was going to try to convince myself I hadn’t noticed.

She gently bounced on my back, whooshing air out of my lungs each time as it felt like my ribcage was collapsing. Heck it probably was! She stood up, turned me onto my back, pulled me by my arms so my head was hanging of the bed, then in a swift motion laid on top of me facing my feet, wrapping my face up high into her crotch and applying a deafening reverse headscissors. She was saying something but I couldn’t hear the words since my head was swallowed by her thighs and ass. She grabbed my dick, at this point flaccid after the realizing that she also had a dick, and was probably twice the size of mine. She gave it a few slaps left and right before gripping my balls, alternating between squeezing and slapping it. I tried guarding my manhood with my arms but each time she would slam my arms down and continue to maul my prostate.

She mercifully unhooked her legs but did not get up, just spread them slightly to give my head some pressure relief. I was starting into the abyss of her ass and could see the outline of her package.

She slid back slightly and pressed the bulging cotton into my face.

“As you can see Alex, I’m not like other girls. I have a little something extra. And when I wrestle little boys like you into submission, it grows into a lot extra.” And by that point it had swollen into a semi erection.

“Please Ashley. Don’t do this to me. I will empty my bank account for you if you just let me go.” I was scared to death. I was being robbed by a 6’7” transsexual who was also crushing me. My dick was being pulverized and I was about to become a cadaver if she continued the violence. I was also equally humiliated. This woman had a dick that was bigger than mine. My brain was confused.

She pulled my arms and tossed me like a rag doll, reorienting me back onto the bed. She crawled on top of me, pulling her tits out of her sports bra and smothering me in a grapevine position. I could feel her dick digging into mine, putting it to shame and also some pain. My arms were pinned over my head so I could not even attempt to defend my manhood. She arched her back and slapped my face with her tits before plopping back into the naked breast smother. Tapping was futile but I tried, only to have her ignore it. She was hugging my face into her breasts now and I was struggling to catch breaths of musty air. She could tell I was catching some air and this did not agree with her suffocating sadism.
She scooted back, pulling my towards the foot of the bed. She climbed back on top of me, planting her humongous ass on my face. My arms were overhead and pinned to the bed by her kneeling on them. Deciding this wasn’t enough pressure, she spread out her legs so now she was sitting fullweight on my face, holding my arms down with her hands. My world was now black and I couldn’t hear anything, as her asscheeks enveloped my head and my face absorbed all 330 of her flesh. I began squirming and flailing my legs trying to wiggle at least to the side to breath. I was close to blacking out when she finally lifted her butt off my face, at the expense of my wrists which were still pinned. Her massive cheeks hovered a few inches from my face while I grabbed two, maybe three deep inhales before plopping back down on my face full weight. She repeated this four or five times, each time staying on my face for almost a full minute and bringing me to the brink of unconsciousness. I was starting to see stars behind my eyelids, which were smashed shut by the weight of her ass.

She rolled off of me, letting my flattened face expand. But the relief was short-lived as she tugged me by my legs closer to the foot of the bed. She climbed on top of me reverse cowgirl style. My hands were at my sides but she pinned them down. She slid back until her ass was just inches from my face, enveloping my neck.

“Time for a little game. You didn’t realize but I was giving you practice just now. So I’m going to sit on your face again until you can guess how big my ass is. Everytime I lift my butt up you get one guess. But I’ll give you a little hint: The length of time I sit on your face is equal to the circumference of my ass in inches. Good luck!” she said, laughing menacingly.

With that she propped her self up and slammed ass into my face, swallowing it and sealing my mouth and nose in her moist crevasse, separated only by a thin cotton thong layer.

Again panic set in after about thirty seconds but I knew this was nowhere close to her measurements. Her clue was deceptively cruel in hindsight, since concentrating on a simple thing like counting became virtually impossible when struggling against suffocation. I got to 45 before I abandoned the count and violently slithered my head to the side, able to grab precious oxygen, albeit damp and humid air since I was still pinned by her ass.

“50. Please Ashley, no more of this,” I said through contorted fishlips

I couldn’t even tell what she said since she was sitting on the side of my head, but obviously it my answer was incorrect because she repositioned my face with her ass and settled back on top of it.

This time she added a layer of difficulty in the short of ballbusting, squeezing and slapping my vulnerable package causing me to squirm while still trying to keep count. I was starting to lose consciousness but was once again able to pull my face to the side, out of her buttcheek vice.
“55, Please Ashley you’re going to kill m-“

“Oooo you’re getting close. A little too close actually,” she said as she stood up to her feet.

She wobbled perilously as the mattress formed an unsteady ground underneath her 330 pounds. She pulled down her thong and it dropped onto my face. When I moved it away from my eyes I was staring up at her crotch and I got the first glance of her massive dick, which looked to be about ten inches and twice the girth of mine. She stroked it gingerly.

“I can’t wait for my victory blowjob,” she growled.

She gave a couple trampoline bounces before jumping back down on my face, crashing down on me as she extended her legs. My entire face felt like it had been punched by the world’s biggest fist, and once again all 330 pounds crushed my head as her naked ass sealed off my air supply. I was starting to flail as my oxygen levels plummeted and I was seeing stars, both because I couldn’t breath and from the impact of her lethal butt drop. This time I could not reposition my head to gasp for air and I could sense the end was near. I bucked my pelvis only to be met with her hand slapping a claw on my balls. I started to see weird bursts of light and soon I had no memory.

I woke up to something firm and fleshy slapping my face. When I came to I realized I was still in hell, as she was slapping me with her erect penis. Beads of precum were leaking from her tip and smeared across my face.

“It was 55, Alex. But I don’t play by the rules.”

I had forgotten what she was even talking about but I no longer cared. I realized I had gone unconscious from the facesitting and had no energy to fight anything.

“I think I’m ready for some 69,” Ashley said.

With that she returned to her reverse head scissors position, only instead of scissoring she pressed her dick against my face. I dutifully opened my mouth to accept her throbbing penis.

“Looks like I’m too tall for you Alex, so unfortunately only one person can do the sucking.”

What did I care? I was being violently molested and suffocated to the brink of death. I had an erection, but it was due to the asphyxiation. She shoved about half of her meat into my mouth, which was enough to fill it. Anymore and I would start to gag. Not her problem she decided, as she began slamming all 10 inches into my throat. I was being facefucked and gagged by a dick as big as a flashlight. Her smooth black balls slapped against my eyes. Once again she felt the need to pin my arms down, more for leverage than anything else. My eyes were bulging as I tried to keep from gagging. I had never given a blowjob before (as much as this could be called a blowjob, anyway) but I did everything in my power to make sure I was not teething, just using my tongue and throat to bring Ashley to climax as quickly as possible. I also did not want to anger the giantess shemale kidnapper. My jaw began to cramp from having to stay open as wide as possible, and out of necessity I started to close it.

“No teeth you little faggot!” she yelled, slamming her fist down on my balls.

Her dick was slimy with my saliva as it smeared across my face.

“I’m sorry. I’ve never done this before,” I pleaded.

She didn’t address my humiliating apology.

“Open your mouth!” she yelled, and I complied.

She slid her veiny prink back into my mouth and resumed fucking my face. Once again I tried to keep my jaw open as wide as possible so I could make her nut as soon as possible. With each thrust of her hips her penis filled my entire throat.

“Oh I’m cumming! Fuck I’m gonna cum!” she said frantically.

I could feel the warm cum hit the back of my throat as she continued to pump my throat. I started to swallow it, seeing no other option and yet more cum continued to flow to the point that I couldn’t swallow it. She pulled her dick from my mouth and finished her orgasm on my face, leaving warm stringy ejaculate on my lips and nose.

“Oh my God. Wow. That was fucking awesome!” she said, as if a new kinder, gentler personality had overtaken her. Her face was flush in post-orgasmic glow. I was beaten. Trapped underneath an Amazonian BBW transsexual wearing only blue bikini briefs, her still erect cock resting on my face, aglow with pearly semen.

“I think you’ve earned a reward. Scoot up!” she said, pulling my back up the bed by my ankles. She remained on top of me in the 69 position, only now I was being smothered by slippery stomach. She stood on all fours facing my feet so that once again I was starting at the abyss of her cheeks. She settled back down and resumed the facestting, once again suffocating me with her sweaty ass. She reached into my briefs and instead of smashing my balls, she wrapped her long fingers around my dick. I was fully erect from the suffocation, despite the fact that I identify as straight and had hard black cock resting on my neck. It was not all gentle though, as she used her other hand to squeeze my balls while she pumped my dick.

“You better cum before I make you pass out again,” I heard her say, as if she had no other option but to smother me while bringing me to climax.

I tried to imagine I was anywhere else, in a situation I actually found hot, and not buried in the ass a 330 pound black amazon who also happened to have a ten inch penis. She gave me periodic breaths, otherwise the facesitting was just as intense as before. My balls were aching as she squeezed them and the feverish heat of her booty was uncomfortable.

I finally felt the orgasm coming on, and the extreme pressure all over my body caused the semen to shoot onto her stomach. She game my balls one last slap for good measure, then wiped my nut off her stomach and smeared it onto my face.

“There’s washcloths in the bathroom if you want to wipe yourself,” she said, in a comically casual fashion.

I hurried to the faucet and began splashing water on my face, rinsing semen and ass sweat off my face. As I reached for a towel and dried my face, I turned to leave the bathroom but as soon as I turned to leave she was standing in the doorway, resting her arm on it. I noticed she had another erection and a sultry look in her face.

“I’m ready for round 2.”