Sissy Maid Dreams

Or a sissy nightmare, plus a Coach Johnson cameo!

Thanks to all for all the comments! I truly appreciate them and please keep them coming. I promise that there will be a much-requested sissy spit roast between Coach Johnson and Coach Tyler later in this chapter. I hope you enjoy it.

This is a tale of male-on-male sex with some non-consensual elements including forced feminization as a young man comes to terms with his evolving sexuality, so if that offends, please look elsewhere.

At seven on the dot, I was ringing Coach's doorbell while dressed in my black and white outfit with my black panties underneath. When he opened the door, he was hiding behind it and nodded me inside. As expected, he was wearing the turquoise blue top and white shorts I had left behind this morning.

Somehow, Tyler looked even younger in the outfit, much like a high school senior in a track and field uniform. The top and shorts were a bit looser on him than they were on me, except his package was obviously a lot bigger than mine!

Coach walked me to the living room with his hand on my butt. "Did you remember to wear your pretty black panties, sweetcheeks?"

"Yes, Sir."

"Good boy." He patted my butt. My dick jerked in response. I was a good boy again! "Are you all prepped for me to fuck you, pantyboy?"

"Yes, Sir."

"Good boy." Coach squeezed my cheek possessively. My ass was still a bit sore from his last fucking, but I was looking forward to having him inside me. That empty feeling inside me was starting to return and if Coach didn't fuck me tonight, I knew I would be begging for his cock tomorrow. We entered his living room and Coach asked, "Like your new uniform? Strip down to your panties and I'll help you put it on." Coach gave me a playful swat on the bottom.

You've got to be kidding me! Spread out on the sofa was a maid's uniform. It was one of those sexy maid costumes in black nylon and white lace trim with a very short skirt with a tiny apron and petticoats attached, sheer black stockings with little pink bows on the tops, a black lace choker and black three-inch-high heels!

Wearing a pair of sexy panties under your regular clothes just for giggles or some sexy fun is something that a lot of guys have done, but dressing in full drag was taking this to a whole different level of emasculation and humiliation. "Umm, Sir. This seems like a bit much."

"Hey, nothing's too good for my pantyboy!" Pat, pat. "Now strip down to just your panties. Good boy. Now sit those sweet cheeks on the edge of the sofa." Coach was rolling up one of the stockings. "Put your leg out. Point your toes." I mimicked what I had seen my former girlfriends do and Tyler started to roll the sheer black stocking up my leg. OMG! The sheer nylon felt amazing on my smooth leg! "The little pink bows go in the back." he explained. Then he grabbed my calf and slipped on one of the heels. His hand felt electric on my stockinged calf. The heel had an open back and a strap that went around my ankle. They were a bit snug, but the size seemed to be perfect.

Coach did the same thing on my other leg and now I was sitting on his couch in panties, stockings and high heels! But there were more frilly things to come! He slid the elastic black lace choker over my head and adjusted it around my neck. "That should hide that Adam's apple." I gulped. One more emasculation had been inflicted on me. Then came the headpiece, an elastic band of black and white lace that he placed on the top of my head just behind the hairline and pulled it back to almost the nape of my neck. Then Coach pulled something out of his pocket. Pop! It was lipstick. He grabbed my chin and smeared it across my lower lip. He motioned for me to press my lips together. Oh, crap. I wasn't into dressing up at all, but I pressed my lips together. "Perfect. That's your color, sweetcheeks. Cocksucker red!" he smiled. But I wasn't smiling. Coach grabbed my wrists and helped me to my feet. I tottered on my new heels. He then picked up my dress. MY dress. I had to hold onto his shoulders as I stepped into it as he directed. Was this really happening? Why was my cock getting chubby in my panties?

Coach slid my new frilly dress up my stockinged legs. I inhaled sharply at the glorious feeling of nylon sliding over nylon. I inserted my hands into the short sleeves and Coach slid the tight tube of frilly nylon up to and over my shoulders. It was so form fitting that I would need help to get out of this thing. Coach had me turn around, which wasn't easy in the heels, so he could tie my apron strings in a big bow at my waistline. I looked down at the short puff sleeves, the tiny frilly white apron that went from my chest down to the hem of the skirt. This costume was obviously made for someone shorter, because the waist ended in the middle of my belly with the six-inch skirt pushed out almost horizontally by the frilly white petticoat. I could feel that my crotch and at least the bottom half of my pantied butt was left totally exposed.

Coach finished tying the apron strings into a big bow in the small of my back. Pat, pat. "All done sweetcheeks! Don't you look just precious." I felt ridiculous. I was enjoying the feel of the stockings on my legs and the feel of silky nylon wrapped around my torso, but I found being dressed up like a sissy maid was simply humiliating. "Why don't you take those heels for a test run back and forth here in the living room. You'll need to get used to them."

"Used to them, Sir?"

"Well, I don't expect my new sissy maid to just look pretty and take my cock. You'll be cleaning my apartment twice a week, too." I was stunned. Tyler had to be kidding. There was no way I was gonna dress up like a maid twice a week, clean his apartment and get fucked by him. I wouldn't. Would I? "Don't look so glum, princess. We both know you'll do anything for a good ass fucking, so start walking." Pat, pat. So I did. I clumsily walked back and forth in the living room while Tyler coached me. "Small steps. Take your time. One foot in front of the other. There you go. Just relax into your heels, don't fight them. Better. Swish those sweet cheeks, pantyboy." I was doing it. Walking in high heels. Well, since I had to keep my arms bent with my forearms parallel to the floor because of how my skirt flared out, I was actually mincing like a little sissy. I was enjoying the feeling of my stockinged thighs rubbing against each other as I minced back and forth. I looked up and froze. Coach was holding my camera and filming me! "You're gonna love the way you look, sweetcheeks. Grab that lube and let's head for the bedroom." I bent over and grabbed the lube off the table. Coach pocketed my phone as I minced past him on the way to the bedroom. He followed close behind admiring how my pantied ass moved alluringly in my new heels. Pat, pat. "That sweet sissy ass is just begging to be fucked, sweetcheeks."

We entered his bedroom and I climbed on top of his black satin bedspread on my hands and knees. "I want you on your back with your head on the headboard. I wanna fuck you like a girl." I rolled onto my back and shimmied into position. Wow. The satin felt amazing on my smooth stockinged legs. Coach propped my head up on a pillow against the headboard, then had me lift my butt and put a pillow under me so I was in the perfect position to receive his cock.

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!

Coach Johnson blew his whistle and called the whole team over. The Pantyboys came mincing off the field. All my eighteen-year-old teammates were there, looking exactly as I remembered them, except now they were all dolled up as sissy maids! "Okay, ladies. Get this princess into her Pantyboy uniform stat! Get a move on, we're burning daylight."

Right in front of the packed stands I was grabbed by a dozen sissy maids that started dressing me in full drag! My pink panties were pulled down and I was forced into fresh black panties. The crowd cheered and whistled, the band started playing "the stripper" and one of the sissies tossed my pink panties into the crowd. One of my friend's dads caught them and waved them around to the other cheering dads before melodramatically taking a deep sniff.

Stockings were pulled up my legs that were spread obscenely open to the crowd. I felt dozens of soft sissy hands groping my bare torso, my pantied ass and stockinged legs as heels were strapped onto my feet. I got hard in my panties, which caused another ripple of laughter through the crowd.

I was so embarrassed to be publicly exposed that I was somewhat relieved when I was finally forced into a sexy maid's uniform with a very short skirt. Then they went to do my lips, but nobody had lipstick, until my high school sweetheart volunteered hers from the stands, saying, "She always loved this color. COCKSUCKER RED!" It was done, I was now a Pantyboy. The crowd applauded that I had been publicly transformed into a slutty sissy maid. "Looking good, champ!" my dad called out again. "No girl is dressed without lipstick." Mom reminded me.

Coach Johnson gave me a visual once over. "Any sissy can dress like a Pantyboy. Let's see if those Cocksucker Red lips live up to their reputation. Ladies, get her in position." My cross-dressed teammates manhandled me onto my hands and knees on the bench while Coach Johnson pulled out his equipment. My mouth dropped open. Coach was even better endowed than his son. He didn't pause in shoving the head of his cock between my painted lips.

Wanting to prove to my Coach that I was worthy of being one of his Pantyboys, I bobbed my head forward while swiping my tongue on the underside of his huge cock and applied as much suction as I could manage. As Coach Johnson started to feed me more of his awesome cock I felt my Pantyboy teammates groping my body and rubbing their pantied cocks against me. The crowd had gone quiet like they were at a golf tournament as I worked deeper and deeper on Coach's twelve-inch cock. The Pantyboys kept feeling me up as I got closer to my goal, the crowd was tensely watching until my red lower lip touched Coach Johnson's balls. The ref blew his whistle while making the goal signal and the crowd went nuts!

"Hey, dad. Mind if I take her other end?"

"Sure, Tyler. Let's spit roast this little bitch." Oh, no. Not Tyler. Before I could even try to object, I felt the now familiar sensation of his cock sliding up my ass just as Coach Johnson slid his cock out of my throat into my mouth. My sissy teammates held me in place as father and son started to work their cocks in and out of my orifices in perfect unison, like they were working a two man saw.

"Looking good, champ!" my dad called out again. With Coach Johnson's huge cock ramrodding my throat, all I could get out as a reply was, "GGUULLICK. GGUULLICK."

"Hey George. Is that your little sissy boy?" one of the other dad's called out.

"She sure is."

"Did you teach her to take dick like that?"

"Not on your life. The Johnson boys trained her, broke her in and turned her out. They made her the Pantyboy she is today. Your boy has a sweet little panty ass. I bet they could train him too."

The Johnson boys sure were training me. It felt like there was one continuous log of cock sawing up my ass and down my throat. Then Coach Johnson decided to mix things up. "Tyler let's switch. I could use a ride in between those sweet cheeks. Flip her over ladies." The Johnson boys withdrew their cocks and I was flipped head over high heels so I was on my back on the bench. I looked up to see my best buds Logan and Dillon standing over me with their cocks hanging out of their panties. They grabbed my hands and had me start jerking their hard dicks right over my face. My two straight buds wrapped their arms around each other, brought their red lips together and got into a deep sissy makeout session above me. My other sissy teammates got the idea and reached over to the Pantyboy on the other side of me, grabbed his hard cock, began jerking it and started making out too! I looked down the line of sissy cocks being jerked off to Coach Johnson sliding his cock between my spread stockinged legs. There was no pain. Only pleasure as he slid his extra huge cock straight up my boypussy. I moaned as I looked up into a sea of jerking sissy dicks with Coach Johnson's plunging prick taking center stage. I felt like that huge dick was pulling me inside out when it withdrew and then almost squealed when the full length rubbed against my prostate on each deep dive back inside me.

I guess Tyler was getting off on the view too. He moaned loudly, "Here it comes, sweetcheeks. Drink it all." His cock exploded about a pint of cum into my open mouth. The crowd chanted, "Swallow. Swallow."