Str8 Turn Out Ch. 06: Sissy Maid Dreams

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I did my best. "GULLUPK. GULLUPK. GULLUPK. GULLUPK... GULLUPK." The crowd cheered as I managed to swallow most of it, but then the Pantyboys unloaded. They moaned into each other's mouths as their balls unloaded volley after volley of sissy sperm all over me. My buddys Logan and Dillon's cocks spurted all over my face and into my open mouth. I was a slimy mess of cum when Coach Johnson exploded up my pussy. He unloaded such a torrent that I felt shoot into me with such force that some blasted out of my pussy around his cock. I swore I could feel and taste it in my throat.

I was a fucked-out mess, so Logan and Dillon helped me sit up unsteadily, but instead of facing the field, that sat me facing the crowd in the bleachers. I was a mess, covered from head to toe in dripping sperm. Logan and Dillon stood on either side of me with their softening cocks pointing at me. "Clean them off, bitch." Dillon ordered. My resistance gone, I took hold of their cocks and licked and sucked them clean. At that moment, the school photographer appeared before us and took a picture of me covered in cum and with Logan and Dillon's cocks in my hands on either side of my face. "Thanks, guys. That will make a great lead-in photo." Huh?

The announcer's voice came blasting over the speakers. "And now, the moment you've all been waiting for...Coach Johnson will present the award for the Pantyboy's MVP!!!" Coach Johnson stepped forward with a mahogany box about a foot square with M. V. P. in gold letters carved into each side and a purple velvet bag draped over the trophy itself. Suddenly I realized that Coach was heading towards me. Logan and Dillon must have realized it too. They put their clean cocks back in their panties and helped me to my feet. The photographer got into position as Coach handed ME the MVP trophy!

"Ladies and gentlemen, meet the Pantyboy's MVP!"

"Way to go champ." My dad shouted from the stands as the crowd cheered and applauded.

Tyler slid into position on the other side of me and the Johnson boys put their arms over my shoulders as we all beamed smiles for the camera. Then Tyler whipped off the velvet bag to reveal the MVP trophy...a giant golden dildo! The camera flashed to preserve the image of the two smiling Coaches with their arms around a cum covered, high school senior dressed as a sissymaid, mouth open in shocked surprise, holding an award that was a foot and a half tall golden dildo mounted on the box with softball sized balls included!

"And now, ladies and gentlemen, the Coaches will help the MVP accept her award..."

Tyler took the award and put it down on the bench. I heard a solid click and the trophy didn't budge when Tyler pulled on it. The next thing I knew, my Coaches had their arms around my shoulders, grabbed my legs behind the knees and lifted me off the ground and positioned my sore ass pussy directly above the golden dildo!

My high heeled feet kicked in protest. I'd accepted awards before, but not THIS way! The Coaches sat me down on the huge golden head and it tore through my panties into my poor ass.

"Ladies and gentlemen, the acceptance ceremony has officially begun!" The crowd started chanting, "Take it all! Take it all!" As I sank lower and lower on the golden shaft. It was ice cold and I started babbling, "It's too big. It's too big. Pleeeeaase stop it. It's too big..." My arms and legs flailed uselessly as gravity inexorably impaled me on the golden spike.

"Ladies and gentlemen, the acceptance ceremony has reached the halfway point!" The crowd cheered and kept chanting, "Take it all! Take it all!" I sank even lower on the golden shaft and was a mess of tears by the time I felt my butt cheeks inevitably come to rest on the cold golden balls.

"Ladies and gentlemen, the acceptance ceremony has officially concluded. The Pantyboy's have a new Most Valuable Pantyboy!" The crowd clapped and cheered at my successful skewering. My teammates pulled the wooden plank seat off the bench and lifted me over their heads chanting "MVP! MVP! MVP!" But on each chant, they pumped the plank into the air and I bounced up and down on the giant golden dildo in front of my parents and the entire school. With every thrust of the golden spike a feminine "EEP!" was forced out of my cocksucker red lips.

I saw my former girlfriend sitting in the stands laughing while the hot shot quarterback who stole her from me sat with his arm around her flipping me off and pumping his hand in time to my impalement.

Coach Johnson thankfully brought the ceremony to a close. "OK, Pantyboy's, take your new MVP back to the locker room and don't forget to bring your nighties to the slumber party at my place tonight where you'll all get a crack at her pussy."

My teammates ran to the locker room carrying the bouncing wooden plank over their heads chanting, "MVP! MVP! MVP!" while I squeaked," EEP! EEP! EEP!" on each bounce.

Then it took a darker turn...

I was in my high school locker room, dressed up in my sexy maid outfit, but it was all clean as if nothing had happened and the locker room wasn't the way I remembered it. It reminded me of a spooky set from a horror movie. Everything was just how you would expect a twenty-year-old locker room to look like with well used lockers, dingy paint job, the smell of dirty socks, but only the occasional fluorescent light fixture was managing to work with a lot of flickering and buzzing.

I walked through the room, looking for a way out. Actually, I was mincing through the locker room in my heels, with my elbows and wrists bent like a sissy, wiggling my butt like a streetwalker, all too conscious of the echoing click clack of my heels on the tile floor. Where the heck was the door? I kept making wrong turns into dead ends and I was getting more anxious as I realized I had no bearings and no idea how to escape.

Then I heard a door slam shut...

Sensing danger, I started to mince faster. Click Clack Click Clack Click Clack

My heartbeat and breathing increased as I minced faster through the maze of lockers. Click Clack Click Clack Click Clack

I froze. I heard someone following me...getting closer. I started to mince as fast as my heels would carry me. Click Clack Click Clack Click Clack

I turned a corner and I was hopeful I was getting close to an exit. There was a long line of lockers on my right and a mirrored wall on the left. The mirror had a bar about four feet off the floor like a dance class. Was I in the ladies locker room?

I hurried down the line of lockers, all to conscious of the mincing sissy maid in the mirror keeping pace with me. Click Clack Click Clack Click Clack

I noticed one of the lockers was open. OMG. Yes! It was my old high school gym locker with all my soccer gear in it. Sneakers, shorts, a top and best of all - men's underwear! Lord, I needed to get out of all this sissy stuff and dress like a man again. I reached out for the boxer briefs and the door slammed shut, the booming sound echoing through the empty locker room.

"You think it's going to be that easy to escape, pantyboy?"

I spun around to the voice behind me. Reflected in the mirror I saw my former self, dressed in jeans, sneakers and a casual top. We approached each other. He was taking the confident strides of an athletic young man in his prime while I approached with the mincing steps of a sissyboy.

We stopped about two feet away from each other with a pane of glass between us. I looked up and down at him, wondering how I had fallen so far so fast. He did the same to me and rated my appearance by giving me a derisive smirk.

"Please help me get out of here" I begged, desperate for a way out of this sissy hell.

"There's only one way for sissy boys to go. Down." He pulled a lever and the floor dropped out from under me. Somehow, I had managed to grab the horizontal dance bar that ran along the mirrored wall and stop my descent. I looked down and saw a fabric chute below me. It looked like I was about to drop down into a giant nylon stocking!

I felt my grip on the bar starting to slip. I looked up and saw my former self leaning on the bar on his side with his forehead resting on the glass and an amused expression on his face. My left hand lost its grip, but I managed to hold on and got both hands back on the bar. Why was it so slippery? My straight reflection rapped on the glass and held up an empty bottle. It was the lube I used to get my ass ready for a good fucking. He smiled and pointed to where the label proclaimed, "Friction Free".

I struggled to hold onto the bar and then I felt something grab my ankle! I looked down to see that there were nylon encased hands reaching out from the giant stocking. They were grabbing and stroking my legs. I fought back against them, but they kept pulling and my grip was slipping. I looked up one last time and my doppelganger waved goodbye to me like you would to a toddler.

I fell into the chute up to my elbows. The nylon encased hands grew bolder, groping my crotch, squeezing my buns, caressing my legs but all the while trying to pull me into the chute to join them. I clawed desperately at the slippery tile floor, but the hands were starting to succeed in pulling me down into the chute. There was something else in the hole. I started to feel nylon sheathed cocks poking into me too.

Suddenly a nylon clad arm reached up behind me, grabbed my shoulder and yanked me back into the pit. The rude hands started grabbing and stroking me all over and the only hand hold I had in the chute were rigid nylon encased cocks!

I quickly discovered that as soon as you grabbed one, it would start shooting jets of cum right at your face. The hands kept pulling me downward and the cocks kept blasting me with sperm as I slid inexorably downward in the nylon chute I had trapped myself in.

I felt like I was in a giant sissy pitcher plant where the only direction was downward into darker and darker realms until my satiny prison had digested me completely. I was sliding downwards faster and faster, falling...falling....

I awoke with a start.

I had to turn on the light to ensure I was safe in my own bed. My heart was pounding in my chest, I was sweating, hyperventilating and at first thought I had wet the bed. Turns out that I must have ejaculated several times during my sissy nightmares...

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5 Comments
MichaelfantasiesMichaelfantasies11 months ago

I agree. Wearing panties and a few other things I can agree to, but wearing a Maid's uniform, or dressing full time!!! Also, that face to face sex IS so personal and intimate! Having one man fuck me, like I was a girl had made me feel even more submissive to him. I became needful of him and that scared me. I LOVE that personal connection! However, the guys I've had sex with in the past, that I didn't know so well, I would purposefully lay on my stomach for them. I didn't want that personal connection with someone I didn't know so well.

About that dream sequence: I sometimes still have dreams that I'm wearing girls clothes out in public and others making fun of me. I know those dreams I have been having is because I was constantly picked on, punished, teased, and humiliated in my growing up years. I wish my dreams would be more to my liking.

HumiliaterHumiliater11 months agoAuthor

@bottomboitoserveyou - Buckle up! there are already two more chapters pending! He/she is on a VERY slippery slope to sissyhood! Thanks for the comment! Feedback is my rocket fuel.

bottomboitoserveyoubottomboitoserveyou11 months ago

Can't wait to read what happens next...as he/she falls deeper into being a sissy maid!

Cowboi_tex89Cowboi_tex8911 months ago

Great story amazing dream sequence would get season tickets to watch those games keep it going can't wait to see what other dirty stuff is to cum I will be

MarcLuciFerMarcLuciFer11 months ago

Great nightmare sequence! But now what are you going to do, a couple more nights dreaming like that, and you'll be too exhausted to act the part of the maid. Maybe it's time to assert yourself again.

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