Coach lifted my legs by the ankles and made me grab my legs behind the knees and pull them up, spreading them wide for easy access. I felt so vulnerable as he slid the back of my panties down to my balls to expose my hole. “Damn, that’s so hot sweetcheeks. Let me take a picture for you, pussyboi.” Like a pussy, I lay on my back dressed like a sissy maid, willingly spreading my legs like a whore for this young punk to mount and fuck. Tyler held my phone in landscape mode and took a photo, then he had me smile for another, then lick my lips for another, finally he had me make a kissy face to the camera. He flipped through them, “I think this on is the best!” He showed me the photo of me licking my lips. OMG! I was almost unrecognizable, almost. It was me, looking like a tranny whore with highlighted hair and cocksucker red lipstick, dressed like a whore with stockinged legs with little pink ribbons on the back just above my bare ass and exposing my man pussy to the world! How had I sunk so far in three days? How low would I sink in another three weeks under Tyler’s coaching? Was there any bottom to this slippery nylon slope I was on?
There was no time for introspection now. Tyler dropped my phone on the nightstand and pulled down the front of his white nylon shorts, hitching them under his balls and rigid ten-inch cock! Oh fuck. For the first time, I was actually going to be seeing his huge cock fuck my pussy up close and personal. Coach Tyler slipped on a rubber and poured lube over his cock. Oh, no! I was going to have to watch Tyler fuck me, face to face. This was going to be horribly intimate and personal versus having a man behind you fucking you “back there”. But there was no turning back now. Tyler was now pressing his cockhead against my open hole between my spread legs. I didn’t want to witness my violation, so I closed my eyes. Tyler smacked my head, “Keep your eyes on mine while I fuck you, sissyboy.”
“Yes, Sir.” I replied miserably. I didn’t want this, I didn’t want to be a sissy maid, I didn’t want Tyler inside me, but I was so under his heel I didn’t resist either. I had finally realized that Tyler was not a Coach training me for a greater purpose, he was just a mean kid with a magnifying glass and I was the ant.
His cockhead popped into my ass and I gasped. Tyler was watching my reactions carefully as he pushed a third of his cock up my pussy.
“Please go slow, Sir.” I begged.
“Push back and let me in or I’ll take it, sweetcheeks.” He warned without any hint of mercy.
I looked my tormentor in the eye and managed to push back, opening my pussy for him so a couple of more inches could glide in. I started to breathe in short gasps like I was having a baby in a desperate attempt to adjust to the incredible sense of fullness. I looked up into Tyler’s face with pleading eyes for mercy but there was none to be found. He maintained the pressure on my colon and I managed to push back again. Tyler took that opening to slam the rest of his cock home. I screamed at the shock of the penetration and he put his hand over my mouth to muffle my scream. I had tears in my eyes and my high heels kicked as I struggled to adjust. “Try to keep it down you slut. Do you want the whole building to know you’re taking it up the ass?”
“Mo, Fir.” I mumbled back.
“Okay. I’ll start out slow like you asked.” Tyler started to slowly fuck me with a few inches sawing in and out of my pussy. I started to open up and the fuck became much less painful and a lot more pleasurable. I was squeaking every time his huge cock bottomed out in my pussy. I looked down at Tyler’s cock moving in my pussy and wondered if this was what a woman experienced when being fucked.
“Okay, sweetcheeks. I’m gonna fuck you for real now. Wrap those legs around me like the slutty girl you are.” Tyler grabbed the headboard and I wrapped my stockinged legs around his narrow hips as he started to long dick me. I continued to squeak as eight inches of hard dick slid deliciously over my prostate on each withdrawal and on each plunge forward. I was actually loving the feeling of our nylon clad bodies sliding against each other. He started to pick up the pace and I grabbed onto the sides of his slim chest, admiring the youthful muscles flexing beneath his blue nylon shirt. Being fucked by Tyler’s shorter and smaller framed young body in his shiny nylon blue top made it feel like I was being screwed by a horny smurf!
“Move that ass and hang on, bitch.” Tyler grabbed onto the headboard with a tighter grip and got serious. He started to really fuck harder, longer and deeper. I kept my eyes on his as I gasped on each downstroke, aided by my stockinged legs wrapped around him pulling him into my pussy. We were in full rut, moaning like animals as the bed protested beneath us.
Tyler pulled with his arms and pushed with his legs in one final thrust and unloaded in my ass. I was almost folded up in two beneath him. He yanked my hard cock out of my panties and jerked it in front of my face. I immediately shot into my gasping mouth and all over my red lips. That was the first time I tasted my own cum.
After we disentangled, I changed back into my usual outfit and staggered back to my place. I saw Miguel the little janitor’s assistant again in the hall and gave silent thanks for the mask mandate, because I had forgotten to wipe off my lipstick before I left!
I washed it off in the shower and again tried to scrub the shame off too. Even if I could wash the shame away, it would do no good because I would be dolled up as a sissy maid again tomorrow to clean Tyler’s apartment. I went to bed early and quickly passed out.
Then I had the most fucked up dream of my life!!!
I was back in my senior year of high school. It was the day of the big game so the stands were packed with parents, students and teachers. I’d intercepted the ball from our rival team and was driving down mid-field setting up my kick on goal when the ref blew his whistle, threw down his flag and stopped the game! Sonofabitch!
I turned to the ref. “What?!”
“You’re out of uniform.”
I looked down. OMG! In front of the whole school, I had no clothes on! All I was wearing, which only made it worse, was a pretty pair of pink panties!
Suddenly, everyone in the stands and on the field seemed to notice at the same time and I was pelted with wolf-whistles, laughter and more than a few rude comments.
“Pretty panties, sweetcheeks!”
“Talk about pretty in pink.”
“Forget the yellow card, ref. Just give her a spanking!”
Coach Johnson called for a time out and waved me over. Dying of embarrassment, I ran to the sidelines with my hands over my crotch. OMG! As I drew nearer, I realized that my parents were in the stands. “Looking good, champ!” my dad called out. “This is why I tell you to always wear clean panties.” My mom nagged.
Then I noticed my teammates. All the guys were dressed like sissy maids and Coach Johnson’s jersey proclaimed the name of our team – the PANTYBOYS! But it wasn’t all spelled out with letters. The Ys were skinny cartoon twinks in pink panties, opera gloves and go-go boots with their legs crossed at the ankles, hips saucily cocked and their arms held aloft to form a Y. The twink at the end was facing forward while the center twink was presenting his pantied ass and winking over his shoulder!