schoolgirl cross dressing

Note: This story is a continuation of the previous three and will be best understood if those are read prior.


I proudly reached the ground without breaking my neck. It was my first time walking any distance or down stairs in high heels, and I could see why they are despised by many women. My pulse raced with anticipation, unsure of what twisted mix of degradation and abuse Za’ana was in the mood to dish out tonight. She was especially sweet and affectionate earlier today in public, once her hangover had disappeared, touching my face, encouraging me to smack her ass, kissing frequently, looking at me with those mesmerizing brown eyes. On several occasions, she whispered into my ear, with that Russian-French accent I had grown to love, how good my cock felt in her ass and that she couldn’t wait for another night with her ‘very nazz-tee guy’.

I hoped I had assembled my clothes how she wanted for tonight’s activities. In addition to the black leather heels, I wore a tight but stretchy white, long-sleeved turtleneck top, thin enough to reveal a flattened black lace bra underneath. My tiny, pleated, red and gray plaid wool skirt barely covered my naked ass and hanging balls, and left a gap of hairy, bare leg before the wide elastic band of the white thigh-high stockings began. My dick was growing a little already, as I felt especially filthy-minded, as I did when I had worn the garter belt. Compounded by the humiliation of wearing ill-fitting female clothing, and knowing how ridiculous I must have appeared, there was something about having my legs and body covered but dick and ass exposed or under a short skirt that I liked; I wasn’t sure why. Back when I was younger, at home alone in my room with the door locked, I wore a t-shirt or hoodie and boots but nothing else if I was in a horny mood. That was probably one reason my dick loved it when I jerked off with only a shirt on in front of her that very first time in Rodanthe, even though I was embarrassed. This night I felt like I was ready for anything, whether it was wallowing in her stinking shit, or having my freshly emptied and lubricated asshole pounded by her dildo. I was already craving it, despite the fact that I could still feel the effects of her recent violations. People in chat rooms said anal gets addicting, and they were right.

My girlfriend, as she called herself for the first time earlier today, was waiting for me, sitting on the pastel yellow blanket sideways on one hip, her legs curled up, sipping a plastic cup of wine. After our fourth day in the sun, her flawless skin had taken on a luxurious, exotic dark bronze hue, which contrasted with her sexy white smile and framed her stunning eyes. Behind her was the view of the cove, darkened but dotted with lights from distant boats and buildings. Next to her was the carton of food and one of her gym bags. Za’ana’s clothing continued the naughty schoolgirl theme, with her dark but sun streaked hair in ponytails on the sides of her head above her ears, tied with long pink ribbons. She wore a white dress shirt, and the outline of a white bra was visible beneath in the moonlight. The shirttails were not tucked in and the lower buttons were undone, revealing her sculpted abs and navel, which was sometimes hidden by her long, striped necktie. A short, dark green pleated skirt flowed around her hips. The Middle Eastern beauty’s long legs were covered in sheer dark blue stockings, which led the eye down to her feet, tucked into burgundy leather loafers.

She kissed me as I sat down and we sat close while nibbling on our fancy sandwiches, fruit, and cheese, talking quietly. In the middle of me thanking her again for the vacation, I spilled some wine on the blanket.

“Don’t worry. I tipped the housekeeper fifty euros to overlook anything that might be ruined or go missing.” Za’ana said with a grin.

We had nearly finished our food when her mood suddenly turned sour.

“Now, it’s time to find out what the fuck you’re doing in those clothes, Robert.” The Middle Eastern beauty asked angrily, her widened eyes catching the light from the cabin behind me. Her pony tails and ribbons flowed with the breeze, in contrast with her serious expression.

I sat dumfounded at the unexpected statement. My pulse began to race.

“I left out one of your shirts and a pair of shorts for you, didn’t you see them? You could have come out here dressed like a man, ripped open these stockings, and fucked me like a man! Are you stupid?”

“I saw the others, but I…thought this is what you wanted…” Again she was messing with my brain. I had never been given any choice before and it was obvious she had wanted me to wear this stuff, but I played along. Still, the thought of missing the chance to slide my dick into her without the theatrics lingered in my mind.

“How do you know the girl’s clothes were not for me to wear on another night? You had a choice and just chose to dress like a little girl, didn’t you? You sick bastard!” She slapped my cheek.

“I’m trying to please you…um…” I stammered, my face stinging.

“Well I see you’ve made your decision, pervert. If you want to look like a fucking little girl, you should act like one!” She said angrily, a moonlit scowl on her face, reaching into the carton of food.

She handed me two oranges, and pointed at my chest, indicating where the fruit was to go. I reached up underneath my top and stuffed them into the empty cups of bra that tightly stretched around my ribcage. I had wondered why the bra was a C cup tonight, up until now, she had given me smaller sizes to wear. The weight against my chest felt weird.

“Here, you need some nipples,” she said, pulling two grapes out of a bunch and handing them to me.

I slipped the grapes into the bra as well, and tried to line them up so each side would match. I felt strange as I looked down at the bizarre transformation. Suddenly a wig appeared, retrieved from Za’ana’s gym bag. It was blonde, almost shoulder length, with large curls that swept away from the front and smelled of hairspray. The purpose of putting me in the lingerie up until tonight, seemed to be for my embarrassment, not an actual imitation of a woman in nearly full dress. I slipped the wig onto my head, and the hair tickled my neck. She ignored my annoyed expression as she reached into her skirt pocket and retrieved a tube of lipstick.

“Stick your lips out like this,” she said, then made a pouting expression.

I did as she said and felt stupid as she dragged the soft, waxy red stick across my lips and around in a circle twice, applying what seemed like way too much, at least compared to what rubbed off of the few girls I had kissed previously.

She commented in French with a condescending tone and made kissing motions at me, then laughed. “It was embarrassing going through customs with the box containing the strap-on cock I purchased for you, and I almost didn’t pack the wig,” Za’ana said, referring to the sloppy imitation of a Farrah hairstyle clinging to my head. But I’m glad I did, because now I get to watch you prance around the yard, my little bitch! Stand up, you fucking pervert!” She slapped me again and spoke several insults in other languages.

I hesitated after I stood, my cheek throbbing and pulse racing, hoping I hadn’t heard her correctly. The roar of an airliner briefly overtook the sounds of the chirping insects around us in the night, and reminded me I was essentially trapped on an island, thousands of miles from home.

“Go on! Prance like a girl!”

I hadn’t felt this much reluctance to do anything she asked since our first days at the Outer Banks. Maybe I wasn’t as ‘ready for anything’ as I thought. This crossed a new line. Despite the lingerie she had me wear previously, I was never asked to be effeminate or act like a sissy. The look on my face must have revealed how I felt.

“I’m waiting, Roberta!” She yelled, using the woman’s version of my name. “If you refuse or fail to perform to my satisfaction, I will go inside and pack and we will be on the next fucking plane to New York!”

I took a deep breath and hopped a couple steps, beginning my latest descent into depravity. My family and friends would disown me if they knew about this secret life I was now living.

“Hold it like this and skip around the yard for me!” She sat up and hiked her skirt above her waist at each hip with her pinky fingers extended to demonstrate, an annoyed look on her face. “Toss your head from side to side!”

At least it was nighttime, so it was difficult for anyone to see me. My stomach was in knots as I clumsily began to trot across the small yard as best I could in the heels, moving the hem of my skirt up, down and around, twisting my hips, and tilting my head occasionally. The oranges bounced inside my shirt, and the breeze passed across my ass, jiggling balls and dick. I passed through the rectangular patterns of light cast across the grass by the cabin’s illumination and reached the edge. Dreading more, I turned around and squinted as the glare of a small flashlight burst directly into my eyes. Just great, I was being spotlighted like a deer in the woods. The glow of the moon and the interior of the cabin was adequate enough for her to see, but that wasn’t enough for Za’ana. The people out on the boats were getting another show. The beam of light was lowered out of my eyes and she barked another command.

“Pinch and roll your nipples!” She demonstrated on one of her own breasts. “Fling your arms around like this!”

I played with my mock mammary glands, pinkies extended, then grudgingly copied her limp-wrist gestures as I hopped back toward her in the light, feeling like an idiot. I scanned the bushes to see if anyone was watching, even though I knew it was not likely. My bigger fear was that this was a progression toward making me a total drag queen. The only thing missing was eye makeup, nails and body-wide shaving, activities she had already begun to share with me as she undertook them. I started to think maybe I should try to end my romance with her before I lost my normal, acceptably macho, small town persona entirely. But outside of her sexual tastes, most of which I willingly acquiesced to, she was a captivating, beautiful, attentive, terrific girlfriend. I was obsessed. Conflicted, my stomach began to knot. I knew I had to at least ride out this week.

“Again!” she shouted before I made another swishy, bouncy, erratically illuminated lap around the perimeter, bra straps digging at my shoulders. “Do some kicks like a ballroom dancer!”

I flung my foot into the air, the hair on my leg visible through the white stocking that covered it. I could feel my meat catch the breeze as the skirt lifted.

“You love doing this! Your circumcised cock is nice and hard!” She smiled.

Sure enough, between the lack of a release after my first official penetration of her the previous night, seeing her nearly naked all day, the physical bouncing around just now and rush of this new level of humiliation, my dick was totally stiff. I had really hoped she wouldn’t notice, as I didn’t want to encourage her to make the cross dressing and prancing a nightly routine. I returned to a spot on the blanket at her command as she rose. I had noticed before that she was wearing a narrow black leather belt, and now she was sliding it out of the loops around her waist and looking at me with her serious, sadistic smile. Dutifully, I turned to face away from her and tucked the hem of the back of the skirt into the waistband, exposing my ass to the breeze. I bent over to receive my lashing, feeling the bra strap tighten across my back due to the weight of the oranges. My cock throbbed in anticipation, and soon the sting of the belt on my bare ass burst into my senses.

“Now I want you to act and sound like a little girl as I whip your fucking derriere!”

Another first, imitating a female voice.

“Let’s hear your little girl squeal!”

I made a short squeaky hum.

“Louder!” she demanded, lashing me once again. Previously during her spankings, I just gritted my teeth and grunted through the pain, holding onto my thighs. “Wave your arms like a surprised, silly teenager!”

I increased the length and volume of my high-pitched cries. Keeping my voice elevated and flailing my arms, with elbows bent downward, limp wrists and fingers spread became easier, almost natural, as the pain of the repeated, randomly timed lashes registered from my throbbing cheeks.

“Now I want to hear you orgasm like a sorority slut! Jerk your cock! Keep your ass exposed, you sick bitch!”

Still bent over, my grape ‘nipples’ pointed at the ground, I reached down and yanked on my dick. My upper arm rubbed against the side of my fake tit, and I raised my other hand to react to her continued, but fortunately less frequent, lashings. It felt comforting and familiar stroking my meat and I began to moan in an uneven falsetto, crying out, jolting and squirming with each strike of the belt. I watched my elongated shadow, cast onto the blanket, whack away as my free forearm swished around.

“Let your mess drip, you stinking little whore!” she yelled as my breathy, high-pitched moans became more frequent.

It wasn’t long before my left hand flapped excitedly as I shot my satisfying load and let out several whiney outcries, simultaneous with each burst of jizz and diminishing as their output lessened. My pulse was pounding in my head as she cursed in some language, flinging the narrow belt across my raw, stinging ass a final few times.

“On your knees! Rub your fucking face in it!” she yelled from behind me. She asked me repeatedly if I was a disgusting, nasty whore.

I answered a squealing ‘yes’ each time as I dropped down and backed up, found the small puddles of cooled semen and complied, but the wig, which was making my head begin to sweat, kept getting in the way. Most of the smelly jizz had soaked into the blanket but I still got a little on my nose and cheeks.

“Are you ready for some cock, little whore? Stand up!”

I arose to see that Za’ana had removed her skirt, and had replaced it with the strap-on, apparently pulled from the gym bag. It looked strange over the top of the blue stockings, but I didn’t care. I wanted her to bend me over, grab my hips and plunge it into my ass. She barked another command before I could start begging for exactly that.

“Tuck your penis behind your legs so you look like a real girl with a hairy vagina!”

I pushed my sack and limp, dripping dick up and back, and closed my thighs.

“Hold up your skirt to show me. Beg for permission to suck on this cock, mon petite bitch!” she said, referring to the protruding dildo, and mixing in a little French. The small black flashlight was pointed under my elevated skirt.

“Please, oh please let me suck your cock! Pleeeease!” I said in the ‘girl voice’, holding up the front of my skirt with one hand, pinky finger extended, and waving my other around, upward, palm facing the sky , excitedly, timed along with my pleading. I gyrated my hips around, still keeping my dick behind my thighs. “I promise to suck it really, really hard! Pleeeease?” I whined, making kissing motions with my coated lips, running my tongue across my teeth and bending at the waist, bouncing slightly for emphasis. It scared me that I seemed to be catching on a little too quickly to the female persona Za’ana demanded of me, although the vocabulary was not any different from what I had used before.

“Show me what you will do to my cock with your nasty mouth!” she demanded.

I started kissing and licking an invisible dick in midair, then bobbing my head back and forth with my lips open and extended, hands out to the side, flailing around. After a minute or so of my pantomime, she sat down on the blanket and spread her legs, leaning back on her elbows, with the brown strap-on pointed right at me.

Moments later I had removed my skirt as ordered, which was irritating my reddened ass anyway, and was on my knees, thighs together, ‘pubic mound’ exposed. I was kneeling between her widened thighs as I ran my tongue up and down the shaft of the brown latex cock. I knew its undulating, vein-crossed, and now, lipstick-smeared surface well, as I was in charge of washing it each night, along with any other cleanup needed after our encounters. In Za’ana’s spotlight, I grasped the base with my thumb and index finger, pinky extended. I held my free hand at shoulder level, elbow bent, palm upward once again, wiggling my fingers around. I got my whole body from the knees up into it, flexing and bouncing to the point I could feel my genitals shaking behind my thighs. After several minutes of sucking it noisily, moaning and answering, in syrupy tones with the high-pitched girl voice, her questions about how good it felt to have a cock in my mouth, Za’ana suddenly pushed my head away and stood, muttering in one of her languages. I sat up, still on my knees, sitting back on my legs, as I saw the latex dick and its leather harness fall to the blanket, which disappointed me, since I again hoped it was butt fuck time.

“Time for a dessert, one suitable for a whore like you!” she said, and pushed the back of her stockings down. Her legs widened, upper body tilted forward slightly, as her gorgeous, exotic face stiffened into a look of concentration for a moment, then a moan and a smile. Soon the breeze delivered a foul smelling hint of what had transpired behind her. Still tingling from the first load, my soft cock twitched and began to grow at the sudden presence of her shit, but then she reached into one of the open white Styrofoam restaurant boxes that contained our unfinished picnic dinner. My stomach again knotted as she assembled her treat, holding the flashlight in her mouth for a few moments like a burglar deactivating an alarm. Her dessert for me was an uneaten segment of her sandwich, complete with a fresh chunk of turd mashed in the middle like a small hamburger.

“Eat this, you disgusting bitch!” She wiped her hand across her white shirttail, leaving a dark smudge.

Another first. The act of consuming her feces in its various forms had of course been purely sexual, but eating normal tasting food at the same time brought on a rush of mixed signals, and I gagged and felt nauseous and dizzy at the thought of the bread, hummus, cheese, lettuce, and tomato in my mouth, mixing with her gummy shit. Za’ana’s hand was soon approaching my open lips, parted to aid in my breathing and still tingling from their recent rigorous contact with the dildo. The putrid excretory creation fell apart as its entirety was forced into my mouth, its multiple tastes and textures fighting for attention. I squinted in the light and gagged as I quickly chewed, moaning complaints in falsetto. I found it was easier to think of the horrid mush as shit that tasted like food, rather than the other way around. She held my jaw and covered my mouth so couldn’t spit it out. I stared at the loosened crotch of the blue stockings as a distraction, since the light from behind offered a brief silhouette of her protruding labia. I finally swallowed the last of my nasty sandwich as Za’ana spoke, standing above me.

“Was that not delicious? You just love eating my bowel movements! You are so fucking disgusting!” Despite her insult, she seemed pleased.

As I responded affirmatively and gushingly thanked her for the dessert, the breeze blew her shirt up for a moment, revealing the lower band of her white lace bra. It was a thrill, even though I had seen her naked most of the week. The flashlight fell to the blanket, casting bizarre shadows on the thick green foliage next to us.

Za’ana reached into her discarded skirt and had me freshen my lipstick, and I smeared it on as best I could. She then spun around, her pony tails swinging, reached down to her rear and raised the blue stockings back up to her waist. She then poked her nails into the fabric, ripping it, and yanked violently on the opening. The beautiful brunette’s bare, tan flesh bulged against the elliptical holes in the stretchy material as it gave way and split across her ass cheeks. She had worn no panties, and her gorgeous brown ass was backing toward me. I was still sitting back on my calves, the heels of the shoes rubbing against my naked, sore butt.

“Beg for more, you sick, nasty bitch!” she said, then spread her gorgeous cheeks, her manicured fingers depressing the dark, soft flesh where they grasped it. The broken-ended remnant of the first turd peeked out of her partially dilated hole. Her labia and the lower half of her rim glistened, lit from below.

“Beg!” she yelled as the log slowly emerged. Random crevices crisscrossed its moistened dark surface, contrasted by a few light-colored spots. Its progress was restricted to about three inches by pressure from the expanded, protruding ring of darkly pigmented flesh surrounding it. The smell was sharp and strong, although my own breath had echoed her stink each time I exhaled, thanks to the ‘dessert’ I had just consumed.

“Please oh please let me eat your shit, Za’ana,” I whined in falsetto as one of her hands abandoned its grip on her dark flesh and two fingers pushed the sepia mass back into her body. She stomped her feet and shimmied her hips slightly, I guess at the pleasing sensation of pressure in her rectum. I felt blood begin flowing into my dick.

“Awww! It’s so beautiful! I want it!” I sounded really pathetic. “Why can’t I have it? Pleeease?”

The begging continued as she repeated the exit and reentry display, although the turd didn’t project as far the second time and stubbornly seemed to resist being forced back inside.

“Please oh please shit in my mouth!” I was bouncing, arms flailing as she looked back over her shoulder at me.

Answering me angrily in a Middle Eastern language, she consented. Za’ana’s ass crack, its less tanned skin, smooth and inviting in the strange light, quickly filled my field of vision and soon my nose was buried in its soft surrounds. I reached out and held the front of each of her upper thighs, grasping the stretchy material of the stockings. My meat began to twitch happily. I opened my lips and planted them firmly against her lower cheeks; a hint of her perfume was still detectable among the heavy fecal stench. My tongue instinctively reached out to taste the blandly bitter log, but was soon forced to retreat by the lengthy, warm, solid invader. I caressed her thighs and whined in extended high-pitched notes of twisted pleasure as I took it in and cradled it for several seconds, feeling it caress the roof of my mouth. I then pushed it between my molars, and slowly ground her putrid, dense turd into a gritty, pasty mush as my cock grew. I didn’t even gag as I swallowed what was once an innocuous breakfast and lunch, before its trip through Za’ana’s beautiful body.

“Is my maird not delicious?” she said as I took a final gulp. “Don’t you love my bowels?”

I nodded and squeaked a positive reply, thanking her, my lips, chin, teeth, gums, tongue and palate coated with her rotten vegetable essence. I had probably built up enough tolerance to E-Coli by now that I could drink the water in any foreign country, I thought as I watched her asshole, glistening with smeared shit and red lipstick, and her quivering cheeks, unevenly framed by the torn stockings, move away in the moonlight. To my surprise, Za’ana picked up the waiting dildo and let its harness fall away. She turned to walk toward me, and I noticed the front center seam of the blue leggings had not ripped entirely up to the waistband as they had in the back. The stockings had split just enough to partially expose her labia, and they flexed from one side to the other as the opening varied with her movement, their brownish pink hue a contrast to the blue surrounding them.

My enjoyment of the view did not last, as she stepped around beside me and bent down, looking at me with those gorgeous brown eyes, lit from below by the black flashlight that remained on the blanket. Her lips approached mine as I looked up at her. Instinctively I parted my lips to accept her always forceful tongue. A large excess of saliva shot out of her mouth into mine, its pinot noir taste only briefly detectable. She moaned loudly as we shared the sharp, slightly diluted taste of her shit for a several seconds. Suddenly she pressed back and down on my forehead, causing me to look up at the stars, mouth open. I could feel the wig slip a little and one of her knees pressing into my back. Her demanding touch felt great. Once again the lipstick appeared, and she quickly added to the thick coating that was already present. Again, my hopeful assumption that it was time to take it up the ass was wrong. The head of the dildo was the next thing I saw, then the shaft and her hand, as the latex cock descended past my open lips. I expected her to begin fucking the hell out of my mouth, but realized she had something else in mind as it continued to descend.

“Take it deeply, you nasty, cocksucking whore!” Za’ana said through clenched teeth, her lips still smeared with shit from our kiss. She then began her usual tirade, this time I think in Russian. Twice she let go of my forehead, but only long enough to give me a quick slap on the cheek, switching back to English, repeatedly yelling “Take it!”, all while holding the dildo, then resuming her pressure, keeping my throat straightened.

Of course I began to choke almost immediately as she shoved the rubbery dick down further, twisting it slightly. My upper body convulsed violently as I noisily gagged and felt the orange titties bouncing and my stomach churning. My eyes watered and dripped down into my ears. My lips, surrounding the shaft, made involuntary flapping fart noises as air was forced out, flinging the snot now leaking out of my nose airborne. Just as I was about to spew, she pulled it out and released her grip, allowing me to face forward, choking and coughing. Thick strings of cola-colored spit dangled from the head of the dick, all of which glistened in the light, and I could feel slime hanging from my nose and jaw.

“Beg for more, you disgusting bitch!” she yelled, smacking me. “I don’t see your hands moving!”

Despite my outfit, I had forgotten about the girl act. So, I raised my arms like a poodle, and pathetically whined for more, admitting I was a disgusting, shit-eating, cock-hungry whore. I looked up and opened my feces coated mouth again, pointing to it and bouncing slightly. She slid the dildo down my throat again and my hands jolted to a mock surrender, then I spread my fingers and flexed my wrists loosely and shook them both rapidly like a baby bird as it descended. I moaned in a high a voice as possible, then had to beg again in gasping falsetto after the latex erection was extracted. Za’ana took me to the verge of puking a couple more times. My upper body, with the bra stretched tightly around, was cramped from the convulsions, and my chin was dripping with thick snot and saliva as I expressed, in the ‘girl’ voice, how much I loved gagging on cock. Finally she released her grip and pulled away. I thought the worst was over until she spoke.

“Hold this right there.” My girlfriend handed me the flashlight, and had me hold it up over my head, pointed down at my jaw.

Suddenly my throat was filled again by the slimy rubber dick and my stomach wretched. The rigid latex cock stopped for a moment, then slid out, the brim of the head striking the back of my upper teeth on the way. I was beyond control and violently and loudly projected what seemed like a quart of stinking, horrible tasting vomit upward and back down onto my lower face and chest. It looked like a muddy volcano as the light momentarily shone through it. I could feel some of the warm, chunky, sticky liquid instantly soak into my shirt, while the rest cascaded off my fake breasts and splattered onto my dick, thighs and stockings.

Za’ana immediately cried out in disgust at the smell, covering her nose with her forearm, still holding the dildo, slimy strings suspended from it and drifting in the breeze. She continued to comment in some language as she adjusted the light beam toward my coated face and forced the dildo past my lips again and down my throat, burning from the acidic vomit. I felt the lower flange of the rubber dick press against my nose for a moment before it jolted upward, followed by grunting convulsions and an overflowing mouthful of thinner, more bitter tasting puke. It was a less efficient ejection, and Za’ana kept my head tilted back as I choked on the liquid, deeply coughing and unable to breathe. Finally she released me and harshly jerked my head forward, but only long enough that my mouth emptied onto the ruined white stockings, briefly warming my thighs. The combination of sour digestive acid odor and the sulfuric feces that had been in my stomach was horrible. I hadn’t smelled anything so awful since I had the flu and diarrhea simultaneously as a kid. She kept the pressure on my forehead as I looked toward the stars, face lit by the tiny spotlight.

The dark night sky and the silhouette of Za’ana’s exotic face above were a tranquil contrast to the chaotic sensations of the pain registering in my burning throat, the muscular fatigue in my throbbing and heaving chest cavity, and the discomfort of being soaked in my own putrid, viscous emulsion. I optimistically hoped that my submission to all of this was satisfying my first love more than any other man ever could.


Realizing what was next, I reluctantly spread my jaws as far as possible, causing the puke on my face to drain down the sides of my neck and inside the high collar of the shirt. Two of Za’ana’s long fingers became enveloped by her shimmering dark lips. I braced myself for the worst, but my cock continued to grow at the idea of this extreme degradation. I continued to shine the light on myself.

Her beautiful face contorted, brow lowered and eyes closed. A hollow gulping noise emanated from deep in her throat as her shoulders lurched and she bent forward, less that a foot from my open lips. She pulled her hand away from her mouth quickly and my eyes closed in reflex as my face was instantly covered with hideously putrid, thick, chunky vomit. I tried to let out a squealing protest, which was stifled as my mouth rapidly filled with the warm stew. I did the spastic baby bird motions again with my free hand as the wig slid off, weighted down with liquid. The differing, stale food and wine taste and stink made me gag once more. I could feel glop sliding down my cheeks, neck, into and behind my ears. One shoulder was now warm, coated as well.

“Swallow!” she yelled, pressing my jaw shut.

I loudly complied, gulping down the lumpy mouthful of horrible tasting mush. It stung my throat all the way down. I then snorted the puke out of my nostrils so I could breathe as I heard Za’ana laugh before plunging her fingers into her throat once again. Her second deluge was mostly liquid, successfully aimed once more at my open mouth. I tried to swallow as she grasped my jaw again but was in mid-breath and ended up coughing most of it out through her fingers. She harshly let go of my head, pushing it to the side and snatching the flashlight from me. I remained in place, facing down and to the side, eyes closed, nearly dizzy, noisily trying to clear my airway as the warmth of our combined stomach contents which coated the front of my body, faded quickly in the breeze.

“Put that back on!” she yelled, referring to the wig, her voice raspy from the liquid in her throat. She began to noisily force up and spit her phlegm, I assume, at me, adding insignificantly to the sticky, reeking gastrointestinal soup I was already drenched in.

Still unable to see, I clumsily felt around back behind me and grabbed the wig. It was soaked in puke. I placed it back on my head, and felt moisture on my shoulders as the remnants of my girlfriend’s dinner dripped off it. Finally I wiped my eyes, and through a squint, saw she had torn open the front panel of the hose and was standing, legs widened, admiring her work and rubbing her clit. Za’ana’s long dark fingers were glazed and dripping with vomit, fresh from their plunges toward her esophagus and where she held my dripping jaw shut. Strings of yellow spit hung from her chin as she began to moan and breathe heavily. The flashlight was once again lying on the blanket, but pointed at me. She stopped when she realized I was watching her.

“You’re not finished, you fucking whore!” She lunged toward me and crouched down, reaching toward my soaked shirt. My fake tits had a valley between them where cleavage should be, and it was filled with cooled puke, most of it the darker shade of my girlfriend’s turd. She scooped an overflowing handful and held it to my chin.

“Eat it, you sick bitch!”

My mouth was already thick with the taste of vomit, but the lukewarm, lumpy mass she shoved into my mouth was still unpleasant as I chewed and swallowed loudly with exaggeration so she would see. Suddenly I felt the wet front of the shirt, now nearly transparent and stained a peanut butter color, being peeled off my stomach. Za’ana held the soaked top open and outward horizontally under my chin, displaying the extent of the vomit and fecal matter sticking to it. It looked almost like a hideous pizza. Most of the liquid began to flow to the center and drip through like a coffee filter into my bra and drain down my stomach toward my nearly stiff cock. The breeze was cool on my bare, damp skin.

“I let you borrow my top and you fucking ruin it!” Za’ana pressed a palm upward under a large splatter and toward my jaw. “Clean it off!”

I began to slurp up the gummy, putrid bits of food in various pre- and post- digestive stages clinging to the stained fabric. I continued for nearly another minute, and switched to using my own hands at her command. She pointed the light at my face and watched, commenting in a few languages what were probably insults. Besides lumps of shit, I frequently encountered fibrous vegetable remnants, still slightly crisp, seeds, nearly intact olive slices, and pieces of tomato skin, all suspended in a tart, slimy, bile-flavored sauce. She then began to make slurping noises and mock me in a falsely high voice.

“Oooo! I’m Robert the nasty bitch! I dress like a girl and act like a whore! I love Za’ana’s rubber cock and I love to eat her bowels and vomit!” She copied my flailing arm gestures and then switched to her own voice. “I don’t hear you telling me how delicious it is, you nasty, ungrateful whore!” She smacked me so hard the wig flew off , and then took advantage of the missing hairpiece to strike me twice more, forcing me to lean to my right and nearly knocking me off balance.

As I straightened up and replaced the soggy wig, the left side of my head throbbing, I looked up and saw the un-harnessed dildo and its belts flying toward my face. I caught it as it bounced off my nose.

“Place it on me, you stinking whore!”

I thanked my standing girlfriend excitedly and crawled over to her as a light rain of puke juice fell off me and onto the blanket. I slid the soft leather strap between her thighs, covering her tanned, beautiful, bare pelvis. She turned around so I could buckle the back above her jiggling ass cheeks, as remnants of the blue stockings clung to her hips. To my surprise, she stepped away and poured herself another cup of wine, upending and emptying the bottle. I realized how much I enjoyed the sight of her, beautiful and in charge, with the dildo sticking out. Along with the anticipation of being violated, my meat stiffened completely in the breeze.

Still on my knees, I happily started whining to be fucked, and pivoted around, reaching back and grabbing my hairy ass cheeks to show her. I leaned forward and spread them, then felt the cool air in my crack. The head of my hard dick was getting dipped in a puddle of vomit as I groveled. I pleaded like a kid in a toy store, bouncing my hips and flexing my already lubed asshole. I began flailing my arms and telling her, in the high voice, how good it was going to feel to have her cock up my ass.

“Okay whore, maybe I will allow you to stick it in your stinking hole for a few moments,” she said, lying down on the blanket, face up and propped up on her elbows, sipping the wine. The rubber cock was pointed skyward, ready for me to straddle her and sit on it.

Less than a minute later, lipstick once again reapplied, I was moaning loudly in falsetto, gushing about how awesome it felt as I rode quickly up and down on the dildo in a squatting position, facing her. I was really getting into it, leaning in different directions, arching my back, and occasionally pausing to rotate my hips in a small circle when the latex cock was only about halfway inserted, reaming out my happy rectum. Chills overtook me as I waved my arms, limp wrists sloppily flinging my hands in random directions. My meat was pulsing, nearly red and extended to its full length, but had lost enough rigidity to make it flop up and down with my hip motion, slapping my puke-coated lower stomach with each bounce. Wild shadows were created by the flashlight, which Za’ana had pointed right at my hole. After several minutes, to give my knees a break, I leaned back into a crab position, arms locked straight behind me, holding my body more or less horizontally as I rocked back and forth, joyfully satisfying my anal cravings. I began to cry out in short rhythmic high pitched tones, sounding like a porno movie overdub. After looking at the sky for several minutes as I rode, my cock flailing, I noticed Za’ana was sitting up, her white shirt completely unbuttoned and blowing in the breeze, revealing her white bra. Her nipples protruded, casting small, moonlit shadows onto the lacy cups.

Apparently she thought I was having too good a time with the latex dick, because I felt her grab my bouncing nuts and slip something around the base, probably the necktie. A broad, satisfied smile from her was the only warning as my groin and lower stomach immediately cramped and I cried out in pain as she yanked violently. The slipknot made my captive nuts feel like they were going to burst, and I fell from my crab position. Za’ana shifted her hips at the same time, and the dildo flexed and sprung out of my spotlighted hole, flinging a sparkling mist of lube into the air.

“I don’t see your arms waving! Squeal like a girl!”

The next couple minutes passed way too slowly has I writhed in agony on my back, trying my best to sound like a girl as she sat opposite me, keeping almost continuous pressure on my nuts. I flailed my arms and raised and spread my legs, covered by the drying puke-encrusted stockings and the heels pointed skyward, at her command. The worn leather sole of one of her loafers appeared, and intermittently kicked or pressed down, adding even more pressure to my balls. I did spastic flutter kicks with my elevated calves as my eyes watered from the pain. Still, I managed to watch her tugging and slapping her tits, exposed and overhanging the underwires of the white bra. Her free hand then released the strap-on harness. Za’ana began to moan and look upward as she frantically rubbed her clit. Soon she convulsed for about a half minute, breasts jolting. After her groaning orgasms, she released my aching nuts, but left the necktie looped around them. I laid there, trying not to break out into sobs. As the pain slowly lessened, I took in the sight of my gorgeous girlfriend. Her face, heaving stomach and chest glistened with perspiration as she rose to her knees.

September 2018
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