Str8 Turn Out Ch. 10: Sissymaid to Bride

Str8 Turn Out 10: Sissy Maid to Sissy Bride

Chrissy works as a sissy maid & dreams of her wedding day.

Thanks to all for all the comments! I truly appreciate them and please keep them coming.

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. You may want to see previous chapters to understand who the players are and how they descended to this level of depravity.

Everyone is OVER 18 in this twisted tale. This is a work of fiction with some unsafe practices. Please be careful in real life encounters.

"Good, girl. Now get the fuck out, I have work to do." Tyler said dismissively.

I staggered to my feet. "Um, Sir? My sissy collar..." I tugged on my pink sissy collar trimmed with sparkling rhinestones secured around my neck by a heart shaped lock with SISSY scrawled on it like I was a pet. Maybe I was now...

"I'll take it off later...IF you do a good job cleaning my apartment, sissy maid. Now, get out."

Fuck. I got dressed and prayed there was no one about in the hallway to see me collared.

Thank God the coast was clear. I ducked out with my key in my hand...Shit. There was an online shipping envelope at my door. I bent over to pick it up, which caused me to drop my key, which caused me to drop the envelope, just in time for Miguel to turn the corner and see me in my sissy collar and the cum in my hair. As I fumbled with my keys and the slick plastic envelope, he squeezed my nylon clad ass and whispered, "PUTA..." and then he continued down the hall like it was nothing.

I finally got my door open and ducked inside. SANCTUARY! My heart was pounding and I took a deep breath. Thank God only Miguel saw me. I would have died of embarrassment if anyone else had seen me like this.

But my dick was hard in my sticky panties...

I dropped the envelope and my mask on the counter and ducked into the bathroom to peel off my sticky panties. I closed the door and caught my reflection in the full-length mirror, OMG. It was no wonder that Miguel had called me a puta. I looked like a gay hustler in my black athletic top, white nylon short shorts, blond highlights, trimmed eyebrows, red fingernails, pink dog collar trimmed with rhinestones and a pink heart shaped lock with SISSY dangling from it!

I might as well have had a FUCK ME sign on my back!

I gargled mouthwash to get the taste of Tyler's ass and cum out of my mouth, peeled off my sticky panties and cleaned up my mess before slipping back into my short shorts. I headed back to the kitchen to see what was in the package. I looked at the envelope. I didn't recall ordering anything. Then I noticed that it had a gift label on it.

"Chrissee,

No maricon should sleep in just her panties.

XOXOXO

Miguel"

What the fuck? Miguel sent me something? With kisses and hugs? WTF?

My mind flashed on humming computer servers and satellites linking up in space transmitting an urgent message around the globe, "Christopher Smith, former straight college soccer player is now a cocksucking, crossdressing pantyboy with a regular hookup named Miguel!" I imagined that I would now be getting besieged with online ads for lingerie, panties, gay cruises, male only hookup sites, men's "fitness" magazines and other ads that I could not even imagine.

Miguel had digitally "outed" me!

Then I realized that the computer algorithms would just be adding this as a new piece of the puzzle that was my evolving sexuality. I had already left little sissy tracks all over the world wide web. How many dildos and vibrators had I bought since that months ago encounter at the new sports bar? Followed up by an enema kit, gallons of ass lube and setting up an account on a gay hookup site. How many hours had I spent over the last few months watching videos of guys getting fucked? How many pages and pages of "straight to gay" and "caught sissy" stories had I read on erotica sites? How many hours of pegging and sissy fucking videos had I jerked off to? How many "favorite" videos had I returned to again and again? When was the last time I had even bothered to look at a straight porn video? I imagined a future employer running a background check and a needle on an "orientation meter" moving quickly from STRAIGHT to BI to GAY until it buried itself at SISSY and started blinking bright pink!

FUCK!

I realized that I had already spent the last few months digitally "outing" myself!!

I felt like I was back in my sissy nightmare, inexorably sliding down that nylon chute into ever darker levels of sissyhood, filled with buckets of cum and ever more degrading acts of mansex.

With trembling fingers, I opened the soft packing envelope to see what gift Miguel had ordered for his personal maricon. OMG. It was a short pink nylon nighty with matching panties!

WTF? I had already fucked Miguel, so why was he giving ME a nighty...? Oh...

Puta...

That's what he had called me in the hall when he tweaked my bent over butt. Miguel wanted to fuck me. He wanted to claim my ass as his pussy - his puta. Then I remembered the hugs and kisses on his note. Was that a joke or did Miguel want me to be his girlfriend? Did he want me to be his sissy bride so he could spend the next few years fucking me to stay in the country instead of being fucked as Coach's sissy bride?

I couldn't blame Miguel if that was his plan. What straight man wouldn't choose a fuckable young sissy like me over being fucked by a man old enough to be his father? I held up the nighty in front of me in the mirror. Hmm... it was nicer than I expected. It was basically a short translucent pink satin slip with lace trim at the hem that came down to almost mid-thigh. The material was sensuously sleek and filmy. This wasn't a cheap knockoff. Miguel had generously spent some real money on my pretty pink present. I couldn't wait to slip into it and see his face when he saw his pretty maricon in it. I hoped he would wear his janitor uniform when he makes me his puta. The thought of my cute little macho janitor spreading my legs and climbing on top of me caused my cock to turn rock hard in my nylon short shorts.

The clock chimed, breaking me out of my sissy reveries. Shit. I had to get back to work. I spent the afternoon doing office work until quitting time. I had a quick microwave meal and prepped just in case Tyler wanted more than a blowjob. At seven I was at his door to clean his apartment dressed as a sissy maid.

I was surprised when he let me in that he was wearing the white trimmed turquoise blue nylon top and the white nylon short shorts with turquoise blue trim that I had worn for his lap dance the other day. It looked like he was planning on fucking me again, so I was glad I had prepped.

"Your maid uniform is in the bedroom sweetcheeks." Tyler patted me on the ass as I headed down the hall. I dressed myself in my maid outfit for the first time. I rolled on the sheer black stockings, stepped into the lace trimmed panties and with a bit of a struggle, managed to get into the short maid dress. I strapped on my high heels and did my lips in the mirror. I checked my look in the mirror and decided that I looked pretty damn fuckable as a sexy maid with a glittering pink sissy collar. I made Tyler's bed while I was in there and tossed his dirty socks and underwear in the hamper. I headed back into the living room to see what kind of maid service Tyler was in the mood for tonight.

My tormentor was sitting on the sofa, watching TV with his back in the corner of the couch, legs splayed with his left foot on the floor and his right leg running along the back of the seat cushions. He saw me approach, held up a leash and beckoned me with a finger. Sigh. So much for housekeeping. I dropped to my knees before him and Tyler hooked the leash to my sissy collar. My Master pulled my head down towards his crotch. I gently stroked his lightly haired inner thighs which caused a quick intake of breath. Tyler's might have my leash, but I was in control here. His white nylon short shorts started to tent in his crotch, so when I ran my hands up his thighs I gently stroked his growing cock through the filmy white nylon with my thumbs. Tyler moaned and after a few cycles, put his hand on the back of my head and pulled me to his crotch. I rubbed my face against the big tent in his shorts as I continued to gently stroke his thighs. My soft touch was reducing the little punk to putty in my hands. I managed to get his balls through the leg opening and gently blew on them. "Fuuuuck." Tyler moaned at my teasing. I slid onto the couch on my belly, grabbed his hips and slowly drew him closer as I licked his balls. He was really enjoying the feel of my tongue, so he didn't object when I grabbed his butt cheeks and kneaded them deeply. I grabbed the waistband in the back of his white nylon short shorts and slowly slid it down over his smooth butt, exposing his taint. I licked the bottom of his ball sack and worked my way lower as I lifted his thighs, exposing his hole. I licked down towards his rosebud and Tyler obligingly spread his thighs and cocked his ass, mindlessly exposing his most vulnerable spot to my evil intentions. I rimmed his hole and he started to moan submissively and my hands glided up over his nylon clad torso gently tweaking his hard nipples through the filmy material. His hole was still a bit loose from my earlier tongue teasing. Tyler was almost ready for me and he didn't even realize it yet.

I pulled away from his ass and slid my face over the tent in his shorts. I kept moving up, sliding my nylon clad torso sensuously over his hard cock until my panty clad boner was rubbing against his rigid cock. I kept humping Tyler as I leaned down and kissed him deeply. He instinctively returned the kiss and wrapped his arms around my back and his legs around my stockinged thighs. I smiled at the incongruity that while I was dressed like a sissy maid, I was assuming the dominant male role and poor little Tyler was easily sliding into the submissive female role. I broke the kiss and pulled away from him but kept rubbing our cocks together as I reached into the drawer in the end table to grab some lube.

Tyler looked more than a little nervous about his coming impalement. I brought my lips down to his and again took possession of his mouth, as I started to apply some lube to his tight little rosebud. Tyler squeaked into my mouth as my fingers started to apply lube to his virgin hole. Without warning I slid a greasy finger all the way up inside him. He tensed and tried to pull away, but I was there to talk him through it. "Breathe, Tyler. Breathe." I mimicked the short deep breaths for him and he followed my lead. "Good boy." I encouraged with a wiggle of my buried finger. I felt his sphincter start to release the death grip on my finger, so I continued the wiggling and kissed Tyler again. My tormentor now whimpered as my tongue violated his mouth while my finger violated his other orifice. As his ass relaxed, I switched from wiggling to gentle thrusting with my finger. I withdrew and added some more lube before breaching his hole with two fingers. Tyler moaned and puffed in discomfort as I stretched him out.

Finally he was ready. I withdrew my fingers from his bowels, pulled my panties down under my balls and lubed up my hard cock. As I pressed the head of my cock to his opening, Tyler instinctively clenched up. "I'm coming in." I told him flatly. "Push back and don't forget to breathe." Our faces were inches apart and he looked scared at what was coming, but I felt him push back and pushed the head of my cock into his ass. Tyler grimaced and started huffing and puffing. He looked very young, very small and very terrified. Damn, he looked so vulnerable I had to take him! But I controlled my passion. "That's it. Breathe. Breathe. Good, boy. Push back again." Tyler puffed a couple of times and I felt him push back. I pressed my advantage and my cock head pushed through his defenses and entered his body. Tyler groaned and huffed as his sphincter gripped my shaft. I let him adjust until I felt him relax slightly. "Push." I commanded and a moment later he did. I couldn't delay and longer and drove my full length deep into the furnace of Tyler's guts. He tensed and groaned. "Breathe. Breathe." Tyler started puffing as his body tried to adjust to the unfamiliar sensation of having a man's cock in his guts. I relished watching Tyler trying to come to terms with having my cock in his new boy pussy. I had done it.

I had taken Tyler's cherry.

When I saw his face relax, I started to slowly fuck his ass with short strokes. Tyler groaned and huffed beneath me but I kept up the pumping, slow and steady, relentless. I felt his ass relax it's grip on my cock a bit and Tyler opened his eyes and looked at me.

I took it up to the next level, long smooth strokes in and out of his once virgin canal. Tyler started to breathe and moan in time to my strokes while looking me in the eyes as I took him. He looked up at me seeking affirmation. "Damn your ass is so hot. It's so hot and tight up there. Take it, Tyler. Take it all." I kissed him again and he moaned as I continued to fuck him. I knew that he was melting inside as he surrendered his ass and mouth to me.

I broke off the kiss. "Ready?" He looked up at me with pleading eyes but gave a slight nod. I smiled. Like I was going to stop if he said no. I planted my hands on his pecs, my thumbs tweaking his nipples as I pinned him to the couch.

Then I started to fuck him for real. His ass was amazing but what I was truly enjoying was the expressions of surprise, lust, fear, disbelief, submission and ecstasy that kept cycling through his face as I reamed his ass causing him to moan like a cheap whore. There was no stopping me now. I leaned forward putting more pressure onto his chest as I piledrove into his ass. Tyler expression was now frozen into an open mouth look of shock as my hips slapped against his ass and he wailed as the nerve endings in his bowels formed new neuron pathways to the deepest pleasure centers of his brain.

Then I looked down and saw a spreading wet stain in his white shorts. Tyler was having an assgasm! I had fucked the cum out of the little twerp. That sent me over the edge as I buried my cock to the hilt up his ass and grunted volley after volley deep into Tyler's unprotected pussy. I collapsed on top of him as I shot my last loads inside him. I had deflowered and bred Tyler.

As we both came down off our orgasms, I gently kissed him stroked his hair and cheek, cuddled his smaller body under mine and whispered sweet nothings in his ear. I wanted his first time to be a special memory. Everyone deserves that, even a little bastard like Tyler.

Eventually he grew embarrassed as the reality of what had just happened started to settle into his brain and he headed to the bathroom on unsteady legs, telling me that the vacuum was in the closet. Really? He still wanted me to clean the apartment? Why the hell not. Maybe I'd get a chance to fuck him again. As long as I was dressed as a sissy maid in high heels, I ran the vacuum around, wiped down the kitchen counters, got the dishes out of the sink and other minor chores. Tyler was tidy around the house so there wasn't that much to do.

Tyler went from the bathroom to the bedroom, came out dressed in sweats and a tee shirt, grabbed a beer and sat down in front of the TV while I tidied up. I went into the bedroom and dropped his sweaty nylon shorts and top in the hamper. I fixed my hair and lipstick in the dresser mirror, taking a moment to admire my look as I pressed my cocksucker red lips together. I did a half turn to check out my butt in my lace trimmed black satin panties as it peeked out from under my short skirt. The heels accentuated the perkiness of my ass cheeks and my smooth legs looked awesome in black sheer stockings. I couldn't resist turning to face my reflection with red lips and shaggy hair with blond highlights, hands on hips, that I cocked to one side as I winked and blew a kiss at the hot collared sissy slave in the mirror. I was ready for round two if little Tyler was, so I strutted back to the living room with my hips swaying in my heels.

I minced over to Tyler sitting on the couch and knelt before him with head bowed and hands on my knees. "I believe I'm done sir. I trust my sissy maid service was satisfactory for you." I might as well have asked, "Was it good for you?"

Tyler was apparently NOT pleased. "You think you did a good job?"

"I'm sorry sir. It's my first day as a maid. I promise to do a better job next time."

"You MUST be punished. Go get three belts from my closet. Now." He snapped.

"Yes sir." As I headed for his closet, I realized that Tyler needed to reassert his dominance after he had allowed me to take his virginity. I stepped into the walk-in closet and saw that he had a belt rack on the wall above a low metal storage cabinet. There were a number of belts to choose from. I took the three widest jeans belts he had, reasoning that they would sting less than the thin dress belts. I headed back into the living room feeling a lot less cocky.

I knelt and presented the belts to Master Tyler. He reviewed my selection, "Very good. These will do nicely. Kneel there and bend over the table, slave."

"Yes sir." I shuffled on my knees to the narrow end of the coffee table and bent over until my chest rested on the top. Tyler buckled two of the belts together and then used them to secure my waist to the table. Fuck. This was serious. I was now defenseless to protect my vulnerable pantied ass.

"How many, bitch?"

Shit. I better lowball this. "F-Five sir? It is my first day and I promise to do better..."

"Hmm... Okay, five it is, but I'm going to make them count." From his pocket, my Master took out a ball gag, stuffed it in my mouth and secured it around my head. Oh, fuck. I really wasn't going to like... CRACK!

FUCK! I howled into my gag. That fucking stung! CRACK! I howled again as the leather snapped hard on my ass. My thin satin panties provided little protection. CRACK!

I was sobbing now. CRACK! I bucked against the belts pinning me to the table. Just one more I tried to console my... CRACK!

I was openly crying. Please stop...

"Have you learned your lesson, bitch."

I nodded my head like a deranged bobble head. "Yeth thir! Yeth thir!"

Tyler groped my stinging ass and I tried to pull away at the pain. "Who owns this ass?"

"Eww dew, thir." Please stop this so I can get out of here. Tyler pulled down my panties and stroked my sore buns. I heard him spit...

I looked over my shoulder and saw him rubbing his saliva on his cock. Thank god I had prepped and lubed my ass earlier. Without ceremony, Tyler mounted my ass and started fucking at full tilt. I screamed into my gag and tried to pull away but there was no escape. I held on as best I could as Tyler tried to re-establish his alpha status. After the pain of entry my ass pussy was able to accept his assault less painfully, but I put on a good show for the little twerp until he shot his load up my ass. "Yeah! Take it, bitch!" he grunted. After a minute he dismounted and pulled my panties back up over my bruised ass.

Master Tyler unbuckled the ball gag and unlocked my sissy collar. He held the belt in front of my face. "Kiss it." I gratefully smooched my instrument of torture. He unbuckled the belts securing me to the table. "Get dressed and get the fuck out."

"Yes sir!" I ran to the bedroom, stripped out of my sissy clothes, took a peek at my glowing red ass before throwing my clothes on and running for the door.

"Same time tomorrow, bitch."

I limped back to my apartment. As soon as I got inside, I grabbed a couple of bags of frozen vegetables from the freezer, wrapped them in a towel and dropped them on a dining room chair. I grabbed a beer and a bottle of bourbon and sat my sore ass down. I took a slug of hooch and cracked open the beer. In a few minutes, the cold pack and the alcohol started to take away the sting from my butt. What really helped with the pain was the sweet memory of taking Tyler's cherry, fucking his ass and seeding his pussy. No matter what he did to me from now on, we would both remember that memory that was delicious to me and unerasable to him.