A gay sex stories: Str8 Turn Out Ch. 06: 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.