Tranny Babysitter: The Conclusion

My cock began to pulse in anticipation. My brain was already waiting for the endorphin signals from my prostate.

"Open your eyes, turn 180°, and worship what is in front of you," came Samuel's voice.

Turning, I saw the monster in front of me.

Bevan, Samuel's assistant, was naked and hairless in front of me. His semi-erect penis had to have been at least 12-inches long and was incredibly thick to go with it. This was by far the biggest dick I'd ever seen. Not even in the porn I'd watched had I seen one bigger.

'How the fuck am I supposed to suck that,' I thought. 'And now I know why Samuel stretched me so far open.'

Gamely, I wrapped my hand around the massive shaft in front of me and tried to accept it into my mouth. Even with all the cock sucking practice I'd had, I couldn't get more than about half Bevan's stupendous length inside my mouth. I'd been able to let the head passed my gag reflex, but my throat refused to relax and stretch wide enough to let him down my gullet.

"You're doing way better than most, Johnny boy," Bevan groaned. "Press your tongue on my shaft and hold still. I'm going to face fuck you, okay?"

In answer, I blinked my watering eyes rapidly. Bevan seemed to understand this meant 'yes', or maybe he just didn't care because he started to pull back out before shoving back in. As Bevan's cock's head reached my lips, I'd swirl my tongue rapidly around the glans and push the tip into his cock's eye.

"Fuck, Master," Bevan moaned. "He's as good as you say he is! I'm going to cum in his mouth."

Using his 'voice of command', Samuel said, "No! You will not. You will pull out and take his ass. I'm going to cum in his mouth."

With some quick shuffling, Bevan was soon squatting down behind my ass and positioning the head of his cock at my ring. I was trembling with fear and trepidation. I couldn't see how this was not going to hurt like a 1,000 wasp stings.

Samuel stroked my neck and back as Bevan took position.

"Just relax and breathe, baby boy. It will only hurt for a little while until your ass stretches to accommodate Bevan's colossal girth. After that, it will be so divine you'll find yourself begging Courtney to fist you so you can experience that pleasure again.

You'll definitely want to make sure you do your Kegel exercises every day after this, though."

I felt Bevan pushing more insistently at my rear fuck hole. Groaning, I sagged down onto my elbows and tried to relax.

With a violent twitch of pain from me, the head of Bevan's colossal cock popped through my knot, and the rest of his dick slipped inside me.

"Fuck, fuck, fuck," I was mumbling and muttering.

I felt so full I thought my ass just had to tear, but that was when Bevan rocked his hips back and forth. Bevan's dick was so huge that at least eight inches of his cock pressed deliciously against my prostate or slid over that spot.

My flagging erection sprang back to full bloom.

"Good boy, now show daddy your cock sucking skills," Samuel said as he wiped the already precum leaking head of his cock over my lips.

Using my well-developed skills, I soon had Samuel grunting and groaning as he sawed his cock back and forth in my mouth.

Bevan was slowly withdrawing almost all of his massive shaft from my ass before changing directions and pushing back in. It felt, well, weird. I'd heard of prostate milking. I'd even watched some milking porn to satisfy a morbid curiosity. This felt almost how that looked and was having the same effect.

As Bevan pushed in, my sphincter would open to allow him easy progress, and as he pulled back, his shaft would drag across my prostate forcing cum out of the eye of my cock. As I involuntarily squirted, my sphincter would clench down on him, eliciting a long, drawn-out groan from his mouth.

"Stop playing with your food, Bevan. Fuck this slut's ass like you mean it." Samuel demanded.

Grabbing my hips, Bevan started thrusting into me harder and faster.

Grunting deeply, Bevan moaned, "I'm going to cum in his ass."

"Do it. Do it, and I'll fill his mouth at the same time," Samuel responded.

I was filled from both ends simultaneously. It was great, but even though I'd cum from being 'milked', I hadn't orgasmed. My cock was still twitching and throbbing.

Samuel saw my ... distress, shall we call it? "Stand up, baby boy. Daddy will take care of that for you."

Samuel gives great head. It only took a few moments of him tonguing my glans and sucking on my cock before I came into his mouth.

Smacking his lips with evident pleasure, Samuel sat behind his desk.

"Bevan, get dressed and go about your business. You, my boy, because you are so gorgeous, can sit there naked whilst we talk.

I'm going to ask you some questions, John. These questions you absolutely must answer truthfully and honestly as these are the questions the defence lawyer is going to come at you with: "Did you, at any stage, by any indication, give Hannah permission to record you in the privacy of your own home?"

I shook my head.

"You're absolutely certain? She never asked, and you just shrugged because you didn't think anything of it?"

"I had no idea I had been recorded until Courtney pointed the camera out."

"Fuck!" Samuel said. "Courtney pointed the camera out? Whose camera is it, though? Hers? Yours? Hannah's?"

"It's not mine, and I don't think it's Courtney's unless she bought one for that night, so I'm thinking it's probably Hannah's."

"When did she take the next recording?"

"The next morning in the spare bedroom."

"The one that Courtney said was now yours? Yours and yours only?"

"Yes," I answered.

"I've got you, you fucking bitch!" Samuel crowed. "Three times I almost had you. This time you're screwed!"

"You know that she's done this before? Courtney told me of another one. I didn't know there were more."

"A teammate's wife? Unlikely your teammate knows?" Samuel said, then held up a hand, "No names, client confidentiality and all, just a yes or a no."

"Yes."

"If she had followed through on the complaint, you and Courtney would have been spared."

"Mi ... that woman came to you for help, chickened out, and then seduced Courtney to stop the recording from getting out? Wait until I tell Courtney. She'll rip the bitch a new one."

"Fine, as long as Courtney doesn't tell that woman that she knows she was seduced by her only after that woman chickened out on the court case."

It took months, I had to go into the coach's office and tell him most of the story because rumours were starting to leak about what had happened, but Courtney and I were finally able to have Hannah convicted of blackmail, illegal recording, and distributing pornography without a licence.

The club offered me as trade that spring. There were no takers, so we headed back to Courtney's parent's farm. I was offered a small appearance fee contract to play in the NEAFL for one of the Brisbane teams.

I was a fucking star, we won the premiership, and I kicked a season-high 66 goals as full-forward.

The best thing was that I gave away to my teammates probably another 40 goals that were almost certainties. I was voted MVP and won the team's best and fairest.

The club that had let me drop sent a 'fixer' to talk to me.

He said, "Keep your head down, keep playing like you are, and we'll pick you up in the rookie draft at the end of the season."

But I don't care. I like my life. Courtney and I are happier than ever. The new bub, a girl who looks an awful lot like Courtney, is a joy.

Samuel became our dominant. He hosts the most exquisitely debauched private, invitation-only parties you've ever not seen. I mostly attend as Olivia and happily service every single cock that is offered to me. Sometimes two or three or four at a time.

Courtney spends her time on the cross, in the cage, or in the play pool. On the cross, she gets whipped and spanked, and anyone who wants to can fuck her ass, cunt or mouth. She still protests, half-heartedly, that she doesn't like pain.

In the cage, she is locked on all fours with her ass out one end and her head out the other. Anyone there can use any of her holes as they see fit.

In the play pool, she is naked and will lie on her back masturbating as anyone, man or woman, or somewhere in between, who wants to, urinates on her. If asked, she will open her mouth to have it pissed in. Or she will swallow your load or allow you to cum on her face, tits, or anywhere.

We have only one rule for that night. We can fuck anyone or everyone we want except each other.

Our sex lives on the farm, in between visits, is wondrous. Courtney wants another baby. We've decided we don't care whose baby it is, so Courtney doesn't use birth control or make her lovers wear a condom.

The End.