Str8 Turn Out Ch. 08: Coaching Sissies

Coach Johnson calls the plays!

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. WARNING! There are also elements of father/adult son incest in this increasingly twisted tale! 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.

"Well, that was hot as fuck!"

Coach Johnson's comment broke in on the post-coital afterglow that Miguel and I were sharing after an intense man-on-man lovemaking session while dolled up like sissy maids. Since it was the first time that I'd been the top in months, I wanted to show my former coach and his cocky son the difference between fucking and lovemaking. It turns out that I would pay the price for being so cocky. The only impact my display had on these two big dicked, alpha male clods was to crank them up to a new level of horniness!

"C'mon Chrissy!" Coach Johnson stood up and latched his leash to my pink sissy collar. "I'm gonna finally get a crack at that sweet ass!" Coach pulled me off Miguel and up to my knees on the loveseat. Coach grabbed and squeezed my pantied ass and raked his eyes hungrily over my stockinged legs. A freshly fucked "Michelle" lay splayed on her back between my knees.

Tyler quickly latched his leash to Michelle's pink sissy collar and pulled her unsteadily to her feet. "I call sloppy seconds on Michelle's ass!" Miguel tottered on his high heels as Tyler hauled the cross-dressed janitor to the end of the love seat and pushed him over the arm with his pantied ass exposed. "Por favor. No mas..." Miguel begged feebly as Tyler pulled down his panties and started to feed his rigid cock into his open pussy.

"On your back, Chrissy," Coach had me flip over on the loveseat with my head against the arm that Miguel was bent over. "You make such a hot sissy maid that I'm gonna fuck you like a girl." Coach yanked down his shorts and underwear, causing his rigid ten-inch cock to slap against his belly. Now I knew where Tyler inherited his huge cock from. Coach lifted my stockinged legs over his shoulders and pointed my high heels to heaven. "Damn. Gams this hot belong on a real girl, but I guess you're close enough, Chrissy." I blushed at what I assumed was a compliment, but it could just as well have been a put down. Coach squeezed a line of lube along the length of his cock, "Go ahead and spread that lube on my cock, Chrissy. Then line it up with your pussy, my slutty girl." I reached down and started to stroke Coach's cock from the tip to the root, getting it ready to violate me. His rod grew even hotter and harder in my hand as he slid my panties off my ass. Coach leaned forward and I obligingly pressed his mushroom head to my hole. Suddenly, I took a fresh look at the leering figure before me, holding onto my stockinged thighs. While he was in good shape, Coach was TWICE my age and he shouldn't me having gay sex with a former player dolled up like a sissy, no matter how eager the little slut was. OMG! I WAS an eager sissy slut. He was old enough to be my father and not only had I lubed his hard rod for him, now I was assisting in my coming impalement. Coach was all smiles as he pressed his cockhead into my ass ring. "Fuck, yeah, Chrissy. Have you been dreaming of this moment as long as I have?"

Dreaming of it? Only, if you counted the nightmare I had last night of being fucked by Coach while my parents watched from the stands! I gasped as Coach slowly slid his huge cock up my ass. My nightmare was coming true. Coach was fucking me while I was dressed as a sissy maid while his son Tyler was fucking my fellow sissy maid Miguel above me.

Tyler had trained me well, so I was able to push back as Coach pushed forward and with a lot of puffing and concentration on my end, he was soon balls deep up my ass. I glanced up and saw that Miguel was having a much harder time taking Tyler's cock. His face was grimacing in pain. "Breathe, Michelle, breathe." I advised my fellow sissy. It took him a minute, but Miguel started to pant like me and I saw his face relax a little. Good for Miguel, but I had big problems of my own, like Coach's big cock up my ass!

Coach had one knee on the loveseat and his other foot on the floor which gave him excellent leverage to dominate my ass. He was enjoying looking down at me as he slowly worked his cock in and out, savoring my moans as he slowly withdrew and my squeaks as he plunged back in. "Enjoying that big cock, Chrissy?"

Moan...SQUEAK!

"I've wanted to shove my cock in that pussy for years."

Moan...SQUEAK! I grabbed onto his thighs as he pistoned my pussy.

"I always knew you were a pussy boy."

Moan...SQUEAK! Coach was stroking my nylon encased legs again...

"You look so sweet in your new uniform."

Moan...SQUEAK!

"I guess you really have changed teams. Heh, heh..."

Moan...SQUEAK!

"You even moan like a girl."

Moan...SQUEAK!

"Let's see if I can make you squeal like one!"

Coach picked up the pace of his fucking.

I started to squeal as his plunging cock skewered my insides. Coach grabbed onto my leg that was on the back of the loveseat with both hands. My other leg slipped off his shoulder so I wrapped it around Coach and used the leverage to pull my ass onto his punching cock.

"Oh. Coach. Fuck. Me. Make. Me. Your. Sis-sy. Girl..." I moaned in sissy passion in time to his thrusts.             

Above me Miguel was less articulate as he was reamed by a younger Johnson cock. "Ay. Ay. Ay. Ay. No. Mas. Ay. Ay. Ay. Ay."

Our eyes locked as we each struggled to deal with a ten-inch cock slamming into our guts. Our mutual shame and lust was reflected in the other's eyes.

"ARGGH. Fuck. I'm cumming!" Coach bellowed as he rammed home one last time and pumped his load deep into my pussy.

His father's orgasm triggered Tyler's own as he howled, "Me, too!" Miguel gave one last "Ayyy." as Tyler plunged to new depths in the Latino's bubble butt and marked it with his scalding DNA.

We all laid there recuperating for a few minutes, a mass of panting and sweating man meat that reeked of sex and shame.

Coach broke the silence. "Damn, you are one hot fuck, Chrissy. I always knew you were a little faggot. Always hanging around me and swishing that sweet little panty ass." Spank. "I could use a beer."

"Me, too." Tyler agreed as he disengaged from Miguel. The Johnson boys went into the kitchen to share a cold one, clinking there bottles together in a toast. I laid there splayed on the loveseat, looking like a prostitute taken by Jack the Ripper, while a whimpering Miguel lay sprawled over the arm of the loveseat like a deer over the fender of a pickup truck.

After a few minutes, Miguel was able to move. While still lying over the arm of the loveseat, he managed to stagger around to the front. I sat up and pulled up his panties and guided him to take a seat, leaning against the arm of the loveseat. I felt very protective of the smaller young man for some reason and placed a comforting arm around his shoulder. Miguel buried his face in my neck, like he was pretending to be somewhere else. I hugged him close and stroked his stockinged thigh to try to comfort him, but also because his legs looked and felt great in nylons.

"You gals ready for round two?" Coach and Tyler came swaggering back into the room.

Miguel looked miserable. "Michelle's already been through two rounds." I reminded Coach while hugging Michelle closer.

Coach's eyes narrowed, then he smiled like an alligator, "Nice of you to volunteer to handle us both, Chrissy." I gulped. "Michelle should thank you for helping her out. Since you gals seem to be sweet on each other, Michelle can pop into your place a half hour before she starts work and you faggots can suck each other off."

Miguel and I both knew that Coach was serious. My mornings were about to get a lot more interesting.

Coach and Tyler sat on the couch. Coach patted the space between them, "Get that sweet sissy ass over here, Chrissy." I gave Miguel a last hug and managed to get my sore ass up onto my heels. I pulled my lace trimmed panties back up over my butt and staggered over to the naked Johnson boys. I gently sat my sore ass between the two big-dicked studs and put a hand on the bare thighs of father and son. It suddenly hit me that although I had been fucked by both father and son, this was the first time I was engaging with them simultaneously. I found myself crossing yet another line of perverted sexuality into incest. Gay incest.

With trembling hands I grabbed a heavy warm sausage of cock meat in each hand. OMG, could I really fool around with a father and son at the same...

Coach put his arm over my shoulder and pulled me into a kiss! Shit! Now I was jerking off a father and son AND making out with my fifty-year-old former coach! All this while dressed up like a sissy! I was losing track of how many depravities I had taken part in just this past week.

Add to that list that Coach was a good kisser and I moaned around his invading tongue as his hand stroked my stockinged thigh. Then I felt Tyler stroking my other thigh and his arm went around my shoulders too. Coach broke off the kiss, "Damn, you're a good kisser, Chrissy. You should try her son." It was hard to believe that after all the gay sex we had engaged in that this was the first time Tyler kissed me. I assumed that he figured that kissing another guy was too gay. It turns out that he was an even better and more passionate kisser than his dad.

I was getting seriously turned on. I was sandwiched between father and son, jerking their huge cocks while they groped my nylon clad body and I turned from one to the other and back engaging in a hot make out session with each of them. Then the unthinkable happened...while I was kissing Tyler, Coach held our heads still and slide his own tongue into both our mouths!

WTF?! What THE Fuck?! WHAT?! THE?! FUCK?!

I was now the meat in a father-son incest sandwich! Coach and Tyler started moaning and their dicks turned to iron in my jerking hands. My own cock was achingly hard in my panties and I moaned along with them due to the forbidden nature of this sex scene where I was literally the man in the middle. I opened my eyes and saw that Miguel was sitting on the loveseat stroking his cock through his panties as he watched with wide eyes the slow-motion train wreck unfolding before him. The Johnson boys turned more towards me as we continued to make out. I felt their hands move from stroking my thighs to stroking each other's thighs. Then their hands moved higher as father and son felt up each other's torsos as our tongues continued to duel voraciously. Something told me that this was not the first time Tyler and his dad had been intimate. Coach then broke off the kiss.

"Let's spit roast this bitch." With a yank on my leash, Coach pulled me to the coffee table and got me up on my hands and knees. Tyler grabbed my head and had me lick the underside of his rigid pole while Coach pulled down my panties and lubed his cock behind me. Miguel kept watching as I was about to become the meat in a sissy bitch sandwich. The Johnson boys started to feed me cock from both ends as I moaned at the thought of being skewered fore and aft on twenty inches of hard cock!

Tyler was holding onto my head as he started to use my throat, plunging a little deeper down my throat on each stroke until I was gagging and drooling with by nose bumping into his pubes. Coach was gripping my hips as he corkscrewed his way inside me until he worked the genetic twin of the cock in my throat all the way up my ass. They set up a slow rhythm withdrawing from my throat and well-used ass at the same time and then plunging back in to the hilt simultaneously. The moaning, squelching, groaning, choking sounds of man on sissy sex echoed through the living room.

"Break time is over, Michelle. Get your sweet ass over here." Through the corner of my eye, I saw Miguel totter over to us on his heels until he stood at my side. In the mirror over the couch, I saw Coach grab his leash, pulling him in by his pink sissy collar to deep kiss the cross-dressed janitor. The volume of the moans in the room increased as Tyler joined in the action and Miguel was now locked in a hot three-way incestuous kiss with father and son. Miguel reached into his panties and started to jerk his own cock as the cocks in my throat and colon started to plunge faster and harder. I was a drooling mess on the bottom of a sissy on man on sissy on father on son pyramid of homosexual depravity!

Miguel came first, moaning his orgasm into the two studs' mouths which set off the cocks inside me, blasting their loads so deep down my throat and up my ass that it felt like their genetic material was intermingling inside me. The depravity of the scene and being surrounded by orgasming men sent me over the edge and I shot a huge sticky load into my pretty panties.

After everyone caught their breath and disentangled, Miguel and I were dismissed for the evening and we went into the bedroom and helped each other out of our sissy outfits. We didn't even look at each other as we left, each lost in our own thoughts. As soon as I got home I hit the shower. I scrubbed down but soon was jerking off with a fistful of bodywash to the memory of being spit roasted by father and son while Miguel made out with them and also my incestuous makeout session with father and son on the sofa. It didn't take long for me to shoot a big load on the tiled wall.

I slipped into a clean pair of pink panties and zoned out in front of the tube with a well-earned beer, sitting on my sore ass in just my pink nylon panties with my feet on the coffee table. I found myself staring at my cocksucker red painted toes as I brought the beer to my lips and sucked on it with my fingernails painted the same cocksucker red. I wasn't thinking, just numbly staring off into space while the disembodied TV audience laughed at whatever was on the tube.

Maybe the cosmic joke was on me...

I went to bed a while later and passed out into a blissful sleep. I found myself dreaming of Miguel. I moaned as he was stroking my butt in my panties and my dick swelled in my pretty pink panties.

"Chreesie...wake up, Chreesie..." Huh? I wasn't dreaming. Miguel was standing over me and rubbing my pantied ass as I lay on my belly with my morning wood pressed into my mattress. Oh, right. He was supposed to come by in the mornings before work for us to blow each other. I glanced bleary eyed at the clock. 5:33 AM! I rolled over and he stroked my cock through my panties. "Mmm...Morning, Miguel..." I smiled.

"Buenos Dias, Chreesie..." Fuck. That accent again. "Pretty peenk panties." He smiled back at me . Miguel leaned down and kissed me. Then he took my hand and put it on his hard rod tenting his uniform pants. I stroked him as he broke the kiss and stood up. Miguel pulled my head to his crotch and humped my sleepy face as he moved back. I slid out of my bed onto my knees and looked up at him in the pre-dawn light. He looked very masculine in his well-worn dark blue janitor's uniform, keys on his belt, a matching baseball cap with his name on it, his long black hair in a ponytail and shitkicker work boots that had seen better days. He pulled something out of his pocket.

"For you, Chreesie..." Pop! I knew what it was. Cocksucker red lipstick. He took hold of my jaw and smeared it across my bottom lip. I obligingly pressed my lips together for him. He smiled down, "Preetty..." He put the lipstick on my nightstand. I knew what he wanted and what our roles were. Miguel was the man here and I was just a panty wearing sissy cocksucker.

I unbuckled his belt and undid his pants, pulling them down. I noted that my red fingernails now matched my lips. I was greeted with a tented pair of classic fruit of the loom white briefs. I looked up at him and pulled the waistband down under his balls. I started to pump his uncut cock, which was a new experience for me. Miguel put his hand on the back of my head and drew me close.

"Suck eet, Chreesie..." I parted my cocksucker red lips and took his head inside. I swirled my tongue around the sensitive head and was rewarded with a moan from my little Latino lover. His cock was silky smooth in my mouth and I really gave Miguel the best blowjob I could manage. I slowly worked down to the root with my tongue massaging the underside of his manly tasting cock. I could smell the soap on his balls when my nose hit his pubes and I played with his nice sized balls gently. "Si, Chreeesssieee..." he moaned, loving my blow job almost as much as I was loving his accent. With my other hand I reached around to knead his sweet bubble butt, eliciting another moan. Then I went into overdrive, bobbing my head faster and faster, sucking with hollow cheeks, lapping his shaft like a St. Bernard on peanut butter.

All too soon he grabbed my head and mashed my nose into his pubes as his cock shot jets of man cream down my throat and he grunted in orgasmic pleasure. I moaned too as his orgasm triggered my own and I made a sticky mess of my pretty pink panties. As he softened, I sucked as much sperm out of his cock as I could, savoring Miguel's manly taste on my tastebuds.

After we separated, Miguel smiled down at me and I smiled up at him. With surprising strength, he reached down, picked me up and put me back into my bed. He tucked me in and gave me a kiss on the forehead.

"Sweet dreams, Chreesie..." Miguel smiled and left. I hugged my pillow and nodded off to sweet sissy dreams about my sexy little janitor.

To be continued...