Str8 Turn Out Ch. 07: Living The Dream

"Enough preening, sweetcheeks," Tyler attached a chain link leash to my new sissy collar and pulled me towards the door. My heart started to race. He wasn't taking me outside, was he?! Somehow, I managed to easily follow him, mincing in my heels as he led me down the hall and then turned into the living room.

My jaw dropped!

"C-Coach Johnson??!"

"Christopher Smith..."

I instinctively covered my pantied crotch with my hands and turned to retreat to the bedroom. Tyler yanked my leash and pulled me back into the living room, "Is that any way to greet your old coach, Chrissy?"

I felt like I was having another sissy nightmare, but this was REAL. Couch Johnson sat on the couch with a shit eating grin, holding a leash of his own that was attached to another sissy maid of his own. I recognized him/her immediately. Miguel.

The little janitor's assistant looked as mortified as I was to be exposed as a sissy. Unlike me, Miguel actually looked pretty dolled up as a sissy and kneeling on the floor at the side of the sofa. He was only about 5'-3" and had a small frame which helped with the illusion. I had seen his cute little bubble butt around the building in his janitor's uniform with a ponytail reaching down to between his shoulder blades, but now his hair had been brushed into a more feminine hairdo. In a word he was cute. Coach Johnson stood up and walked towards me with Miguel crawling behind on his hands and knees. I felt like a tired swimmer who suddenly realized he is way too far out from shore to avoid drowning.

Coach came up to me and placed his hand in the small of my back like he used to do back when I was a straight eighteen-year-old jock. My head was bowed and I stared at the floor. I saw Miguel doing the same thing, probably hoping like me that the floor would open up and swallow us. "Turn around, Chrissy. Let me see if those cheeks are still as sweet as I remember them."

"Yes, Coach." I turned around on my heels and presented my pantied ass to my former coach. I felt the coach's hand slide over my butt, exploring, kneading and patting it. My cock sprang to life and tented my panties. Please, no...

Coach turned me back around to face him. He gently ran a fingertip over the bulge in my panties, causing me to gasp. "Looks like someone's happy to see her old coach," he pulled me in by my leash and kissed me! His tongue invaded my mouth while his hands explored my nylon clad body. Finally he broke the kiss, leaving me panting. "You make a very sexy sissy maid, Chrissy."

"Thank you, Coach." I mumbled staring at the floor.

"Hey Dad. I have an idea. Before we get to the main event, how about a little girl-on-girl action between these two sissies?"

Miguel and I locked eyes. Neither of us liked this idea - at all.

"Great idea, Tyler. Grab us a couple of beers." Coach yanked Miguel up to his feet by his leash. "C'mon, Michelle. You and Chrissy stand together right here in front of the loveseat." Tyler brought in the beers and he and his dad sat on the couch waiting for us to put on a peep show for them.

"OK, girls. Let's start with some hot kissing and heavy petting."

Miguel and I turned to each other. He was still looking at the floor. I chucked him under the chin. He looked up at me with pleading eyes as I brought my lips down to press against his. I kissed him gently then slid my tongue slowly between his lips. His mouth tasted sweet and his tongue started to hesitantly duel with my own. My hand slid around his back and pulled him in closer. He was smaller and prettier than me, so I was instinctively slipping into the role of a sissy top.

"Careful, Michelle. It looks like Chrissy wants to make you her sissy girl." The Johnson boys laughed heartily as their newly minted sissy boys made out. "Why don't you gals have a seat on the LOVE-seat." Tyler guffawed at what he probably thought was a clever pun and his boorish father laughed along. Apparently, the apple didn't fall far from the tree.

"Chrissy better not fall in love with my Michelle. We have to get gay married in a few months if she wants to stay in the country." Coach Johnson chided. "She's gonna make a beautiful bride!"

More guffaws.

The Johnson boys may have carried themselves with a certain swagger and air of inner strength, but they also possessed all the well-earned cliches of the alpha male. They were loud, boorish, arrogant, self-centered, inconsiderate social boobs that I had little respect for.

Miguel and I sat down on the loveseat and he looked up at me like a lost puppy. I understood that look of vulnerability, fear, lust, uncertainty and hopeful nervous trust. It was the same look that I had given Papa Bear. I put my left arm over his shoulder like I used to do with my jerk off buddy Tony, smiled down at him and whispered, "Beautiful Boy," before I kissed him. I felt Miguel melt under my gentle kiss and he returned it with passion. His right hand reached over to gently massage my growing cock through my panties. I reached down with my right hand and gently stroked his stockinged leg. It felt amazingly smooth and silky. I lifted his thigh over mine and we both moaned at the erotic sensation of feeling another stockinged leg brushing our own.

I started to stroke Miguel's respectable panty bulge as we made out on the couch while the two alpha clods watched. They had grown uncharacteristically quiet as they watched the hot scene unfolding in front of them. Two fit young men dolled up like sissy maids making sweet love right in front of them, had exposed the Johnson boys' Achilles heel. They may have big dicks and know how to fuck and dominate, but they knew nothing about making sweet love. Miguel reminded me of Tony with his small frame and long hair, so this was going to be like finally making the move I had regretted not making all those years ago. Also, I had a lot of sympathy for Miguel after Coach had spilled the beans on how he was exploiting his future sissy bride. I wanted Miguel to experience a true lovemaking session that would raise his expectations beyond what Coach could ever deliver.

Miguel reached up with his free hand to cup the back of my head as we kissed. I did the same and was surprised at how silky his fine black hair felt. I took things to the next level by slipping my hand under his knees and gently lifting him onto my lap. He was having trouble sitting still due to the sensitive backs of his stockinged thighs rubbing against my stockinged legs. It also didn't help that I was groping his butt and stroking his hard cock through his lace trimmed panties.

We took a minute to come up for air. He looked up at me with his red lips parted, panting with arousal, permission to take him but to please be kind and gentle in his eyes. I smiled down at him and again called him my, "Beautiful Boy." My smile widened when he blushed sheepishly at the compliment. Dear God, I had to take him. I gently leaned to the left until I had Miguel on his back, then moved to my hands and knees above him, gently spreading his stockinged legs with my own. I lowered myself until our fronts touched gently. Miguel sighed, "Oh, Chreesie." Damn, his accent turned me on big time! He wrapped his arms and legs around me in real passion and I kissed him deeply as I rubbed our pantied cocks together.

I reached down with one hand and slipped my panties below my hairless balls, releasing my hardon. Then I pulled Miguel's panties down his smooth cheeks to gain access to his hole. I slipped a finger in gently and he moaned into my mouth as he easily accepted my finger into his pre-lubed pussy. This was not virgin territory and he easily accepted another finger. I fingered Miguel's boy pussy to ensure he was ready to accept me, then rubbed some of his lube over my rigid cock. I moved forward until I was pressing against his yielding rosebud. Our faces were inches apart, I looked into his eyes and told him, "Push back if you want me to take you."

Damn, he was adorable! Miguel looked up at me nervously, biting his bottom lip he gave an almost imperceptible nod of approval as I felt his pussy open for me. I moved forward smoothly into his open quim until I bottomed out. Miguel drew in a drawn-out gasp of surprised pleasure as I claimed him. "Ohhhhh, Chreeeeesie," he gasped, causing me to moan in pleasure too. His accent was driving me crazy, along with the fact that it had been WAY too long since I had my dick in a pussy this hot! I slowly started to fuck little Miguel and we were both moaning and gasping as we looked into each other's eyes. I had been playing the role of a gay bottom for so long that it felt awesome to be fucking again. Miguel started to match my thrusts with his hips as our pace and moans increased in speed. I loved how his moans went up a pitch and his eyebrows arched and knitted together when I bottomed out. It was awesome, but I needed to go for the goal, "Ready?"

Miguel gripped me tighter and nodded in nervous anticipation. We got down to some hard man on man fucking. Our hips were slapping, the loveseat was squeaking, I was grunting and Miguel was moaning. I may have been dressed like a girl, but I was fucking and loving every inch of it. It also helped that Miguel was a much better fuck than most of the chicks I had nailed and in his maid outfit was a lot sexier. I was loving Miguel's hot pussy and I could see in his face that he was loving my cock. We were in a feedback loop of fucking where our pleasure only increased the pleasure for the other and we were rutting like a well-oiled machine. If only we could do this forever, but all too soon I fucked him past the point of no return and Miguel unloaded his balls into his panties, but what pushed me over the edge were his moans, "Oh, Chreesie, Oh, Oh, Oh, Chreesie, Ohhhhh, Chreeeeesie!"

I lost all control and jerked spasmodically as I blasted my biggest load ever up Miguel's pussy in the most mind-blowing orgasm of my life. It was that damned accent...and that Miguel was suffering from a case of terminal cuteness. When I finally managed to regain my bearings, I held Miguel close and kissed him gently. The poor little guy was splayed out under me like a spent cheerleader slut after homecoming. We gently kissed and caressed each other in our sweaty maid costumes as we shared a pleasant afterglow.

Until I heard Tyler say, "Wow...!"

Miguel and I looked over at the Johnson boys sitting on the sofa. I think we both had completely forgotten about them in the throes of our passion. They were both just sitting there watching us with their empty beers between their thighs.

Finally, Coach said, "Well, that was hot as fuck!"

To be continued...