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!