Tranny Babysitter: The Conclusion

It should go without saying but: This is a work of fiction. Any resemblance to actual people alive or dead is merely coincidence.

Warning: There is a lot of use of words that are currently deemed derogatory, insulting, and demeaning. The characters, who are mainly a mixture of gay, gay curious, bisexual, or bisexual curious, trans or trans friendly , call each other names such as fag, fagboy, poofter, pooftah, queer, and worse.

If this offends you, this is not a story you need to read.

Chapter 07: The Second Friday.

I didn't want to use the fucking machine, but come early Friday evening, after the group fitness session, I was horny with aching balls again, so I positioned the dildo where I could back my ass onto it. Changing the tilt on the fucking machine's arm brought it into close contact with my prostate.

With a needful moan, I turned the motor on and adjusted the speed of the dildo's rotations until the sensations it was giving my prostate were exquisite to the point of pain.

Moaning and groaning fit to shake the house down, I held myself just short of that indescribably delicious point of no return, where your orgasm is coming regardless of what you do for as long as I could stand.

I wanted my orgasm to be so intense that it would be days before I needed to cum again.

I was vaguely aware that the light on the camera had turned green. Either Courtney or Hannah or both were watching the show.

Five minutes passed, then 10, then 15. I was getting louder and louder but still had myself under control. I felt almost like I did when I was filled with the need to cum, but I was denying myself, waiting for the woman to beg me to cum because she could take no more.

I thought I might make 20 minutes when I heard Courtney go, "That is so fucking hot! I want to see you cum, baby."

Mind gone, I blew immediately.

"Fuck yes," Courtney exclaimed through the camera's speaker.

I could hear her cumming, too.

The cock cage was a cum filled and covered mess. My semen had filled the cage up and then leaked out everywhere. My balls, inner thighs and abdomen were covered in salty, gooey liquid. The bed sheets were soaked from where my cum had shot out through the hole used for pissing.

"Shower and come to my bedroom naked," Courtney instructed.

It was around 6.30 pm.

When I knocked on her door, Courtney said, "Come in, my getting ass fucked loving poof husband."

I entered. She and Hannah were getting ready to go out.

"On your knees at the end of the bed, hands behind your head, shoulders up and back, head up, but your eyes down and closed," Courtney demanded of me.

I took up the required position.

"Spread your knees a little wider."

I did as instructed.

I felt a hand at my balls, there was a click sound, and my dick was released from its cage. It immediately began to go hard. Courtney dominating me had me needing to orgasm almost as severely as before I had cum.

"Go get ready to go out," She peremptorily dismissed me.

"I moved to the vacant vanity to begin putting on my makeup.

"No. Grab some boy's clothes and everything else you need to dress for dinner at a pub," I was told.

I looked at her, startled.

"Do what you're told, John," Courtney demanded.

I grabbed some jeans and a polo from my side of the closet. I dug out some socks and black dress boots and returned to my room.

"Your mum's coming to pick up the boys. Once you're dressed, wait for her in the lounge," Courtney called as I exited her room.

I asked Zac if he'd been fed.

"Nana's going to treat us to Maccas on the way to her place," he informed me.

"Can I tell you a secret?" He whispered.

"Sure," I answered.

"Don't tell mum, okay? But I don't like Hannah. I don't want her living with us. She says bad things about mummy when mum isn't there."

"Like what?"

"I heard her on the phone to her boyfriend, and she said, 'I've got her under my spell, the stupid _ '. I don't know what the word was, but it wasn't nice. Then she said, 'I'll have access to her bank accounts shortly.'"

"That isn't very nice, is it?" I said. "But you're right. We'll have to keep this our secret, won't we? Cos mummy really likes Hannah, and she won't believe us."

Zac nodded his head, "I won't tell."

Mum banged on the door and walked in.

"Your father's waiting in the car. You know how impatient he gets. Are the boys ready?"

"Hello, mum," I answered with a grin. "It's good to see you, too. Oh, and yes, I love you, too."

She gave me the gimlet-eye, "You're not so old, bubs, that I caint smack your ass for being a smart ass," she growled at me with feigned indignation.

"Oh, mum! How delightful! Shall I get the wooden spoon?" I riposted.

She laughed loudly, "You always were an impossible child," she told me fondly. "Now, kiss your mother and help me put the kids in the car. I have never been able to figure Isiah's baby seat out."

She was gone.

I waited in the lounge for Courtney and Hannah to appear.

They appeared hand in hand around 7.45, looking like the last two Miss Universe contestants waiting to see who would be crowned the winner.

'Courtney, by a hair,' I thought.

"They finish taking orders at 8.30, so we'd better hurry up," Hannah said as if it was they who had been waiting for me.

"Where are we going?" I asked so I could order an Uber.

"The Sportsman Hotel," Hannah answered.

Courtney and I often catch the drag shows there, so it didn't occur to me that I should be frightened about what these devious two bitches had planned for me.

We made it with about 15 minutes to spare. Courtney had booked us a table, so we were able to sit and order straight away.

I was relishing the giant, rare, rump steak chips and salad I had ordered when Hannah said, "After dinner, Courtney and I are going to act as lesbian lovers. You, fagboy, will take a seat in the downstairs Karaoke bar and allow yourself to be picked up by a gay man. You will let anything and everything he wants to do to you happen, and you will do to him anything he asks for.

"I fucking will not!" I tried to mutter, but heads turned our way, so I guess I wasn't that quiet. "I can't be seen taking a guy home!"

"In the Karaoke bar, the only teammates you'll see, or who will see you, will also be gay. They won't say anything about it, just as you wouldn't say anything to anyone about them being there." Hannah pointed out.

"I'm still not fucking doing it," I replied.

Hannah got out her phone, hit some buttons, and then turned the phone to me. The first video was a short one. It was of me taking my cock in my mouth and sucking myself off. The second was much longer. It was the one from earlier this evening.

She turned the sound up enough so I could hear myself moan.

"Shall I press send, John? She asked as she hovered her finger over the 'share' button.

My steak now tasted like ashes. I pushed it aside and made my way downstairs. Taking a seat at the bar, I decided to write myself off.

"10 scotch rocks," I requested of the barman.

"Do you have nine friends about to join you, mate?" he asked.

"No."

"Sorry, babe," he said. "The binge drinking laws mean I can only serve you two at once."

Fuck.

I handed him my credit card, "Just keep them coming until I fall off this stool," I told him with a forced smile.

He shook his head again, "Can't do that either, sorry, mate," he said. "As soon as you show signs of intoxication, I must stop serving you."

Double fuck.

"Keep them coming for as long as you dare," I replied, then pushed a $50 note under the apron string around his neck.

"Will do, buddy," was his reply. "Bad day, huh?"

"You have no idea," I honestly told him. I doubt anyone would believe what I've been through this week.

"Hang in there, mate," he said, then patted my shoulder. "It gets better. It always does."

Maybe, but I couldn't see how.

It was only 9.00 pm. The drag shows didn't start until 9.30, and the place wouldn't fill up until after the first show, so I had a bit of time before choosing whom to let pick me up.

A few guys sat next to me and tried to start a conversation, but they were all old, overweight and gross. I tried to be polite, but I knew I was being quite brusque with most of them.

At about 10.00 pm, an older, distinguished-looking gent sat next to me.

"Johnny Blue, please, barkeep," he asked of the bartender in a smooth cultivated voice.

My ears pricked as I'm a scotch enthusiast. Johnny Walker Blue isn't cheap, but it's a great, smooth drink.

"I'll have one of those, too, please," I said.

The man turned to me and looked me over, "Samuel," he said, offering his hand.

"John," I answered.

"You look like that AFL player," he told me.

"I am that AFL player," I replied.

And you're gay?" he asked.

"Tonight, I am," I told him truthfully. "My wife, and her Mistress, have decided to turn me queer."

"It doesn't work like that," he told me. "You're either gay, bisexual, or not. Nobody can make you gay."

"Then I guess, at the very least, I'm bisexual," I told him. "I've sucked more cock, and taken more cock in my ass in the last almost two weeks than most street hookers."

He laughed, "You like to please your Mistress, your wife. Yes?"

Maybe it was the alcohol talking, but I answered, "Yes. Her dominating me makes me so fucking hot."

"And she's sent you here to seduce a man?"

"Not quite," I replied. "She's sent me here to be seduced by a man."

"Consider yourself seduced, then," he said confidently. "Will she be joining us?"

"I don't think so," I expounded. "At a guess, I'm supposed to take you back to my place and let you fuck me on my bed so she can record me being fucked."

"There are cameras in your bedroom? He asked.

"Yes, at least two."

"Interesting," he mused. "And your wife has a Mistress?"

"Yes, Hannah Jovovich."

"The tranny?" he questioned.

"You know her?" I returned.

"Of her, not really 'know her'," was the careful response. "And she has recorded you in numerous sex acts?"

"Yes."

"And you gave her permission to do this?"

"No."

"More and more interesting," he said.

"And you are your wife's submissive?" he asked.

"That's that 50 shades bullshit, isn't it? I have no idea what it even means."

"But you do what she wants, and you get sexually aroused by her telling you what to do to whom?"

"Best orgasms I've ever had," I told him as the Johnny Blue warmed my stomach.

"I'm going to kiss you now, John," he informed me. "You will either enjoy it or not, but you will let me do it."

He had the same kind of voice control that Hannah used on me, and I found myself helpless to resist.

He tenderly held me by the back of the head and lightly brushed his lips across mine. I met his lips with a slight widening of mine.

Gawd help me, but I felt a rise in my pecker.

Samuel pushed his lips more firmly against mine, then snaked his tongue out to brush across my teeth. I opened my lips a little wider to let his tongue inside.

"Good boy," he told me as he released me. He then openly grabbed a feel of my cock. "And you're going hard, good signs."

Samuel turned to the barkeep, "My friend and I will have another, please, my man."

"There are booths in the back, John," he told me. "We're going to take a seat back there. Once I'm settled in place, you will slide under the table, take my cock out of my pants and suck me off."

"Yes, sir," I found myself answering.

We moved to a vacant booth around the 'L' in the bar. It was dark. You could make out vague shapes but not much else.

With a shiver of anticipation, I slipped under the table and got on my knees before Samuel. Working by touch, mostly, I managed to unzip his fly and find the dick inside. From how it felt in my hand, it was only a little bigger than mine in length but way thicker.

As I stroked it, it began to harden. I gently pulled his balls out of his underwear to cup them and rubbed my index finger across his taint.

"For a newcomer, you've learned some good skills, my boy," Samuel moaned.

Forming my lips into a perfect 'O', I took the head of Samuels's 7+ inch cock into my mouth. I wanted to show this sophisticated man that I wasn't some gauche youth. I wanted to please him, and for him to like me, so I relaxed my throat and allowed all of his length into my mouth, over my gag reflex and down past my tonsils.

My lips came to rest against Samuel's abdomen.

"Oh, my goodness, baby boy," Samuel moaned. "You are quite the cock sucker. Do you want to take my load?"

I groaned my affirmation.

Samuel gripped my head in his manicured hands and thrust three times up, in and out of my throat. Samuel held my lips firmly against his abdomen at the apex of his third thrust as he squirted. He didn't have much semen for me, but what he had was deliciously sweet.

"Sit next to me, boy," Samuel instructed.

I crept out from under the table and sat beside him.

"Take your cock out."

I eagerly unzipped and fished my rock-hard 7.5-inch dick out of my jeans.

Samuel handed me a napkin, "Cum into the napkin, my little slut," he said.

His control of voice intonation and inflection had me mesmerised. When he told me to cum, I couldn't have stopped myself even if Courtney or Hannah had told me no. I spat cum viciously into the napkin.

"Give it to me."

I handed him the napkin, then looked on, fascinated, as he opened the scrunched-up part and licked my cum off it.

"I will allow you to cum in my mouth at some stage tonight, little one," Samuel told me. "But, for now, it's time you took me back to your place."

"I need to ask permission," I told him.

"By all means," was Samuel's reply.

I texted Courtney, 'I have made my selection. See you tomorrow.'

'Good fagboy,' came back.

Samuel and I caught a taxi back to my place.

I opened the front door and let him inside.

"My bedroom is upstairs to the right," I told him.

"On your knees first, my boy," Samuel said. "Time for you to swallow another load."

I was quickly on my knees in front of my man.

"You will open your mouth, cover your teeth with your lips and tongue, and then allow me to roughly fuck your oral cavity until I cum. I will punish you if you spill a drop," Samuel said authoritatively.

"Yes, Sir," I groaned, then opened my mouth wider.

Samuel grabbed me by my ears, then rudely shoved all of his thick, close to 8-inch penis into my mouth and down my throat.

Holding me tightly to him, Samuel brutally fucked my mouth for what seemed like an age. I was so turned on at being used by this dominant, older man that I had to firmly concentrate on not cumming.

In my aroused, submissive state, I wanted his permission before coming.

"Swallow it all, my dear," Samuel said before erupting into my mouth. I gleefully sucked it all down.

I was almost disappointed there wasn't more.

Samuel sat on the couch.

"Stand there," he pointed at a spot just in front of where he was sitting. "Drop your pants and undies."

Pants around my ankles, I stood where he indicated.

"Hands behind your head, eyes on the wall in front of you. You will not look down, nor move your hands, nor move from this spot until I tell you that you can," Samuel instructed.

Samuel gently took my balls in his right hand, then slid his left hand between my thighs, over my perineum, and onto my ass cheeks. He used his thumb and the last three fingers of his hand to spread my ass cheeks so he could finger my rosebud.

With my eyes clenched tightly closed, I groaned as he fingered my chocolate starfish.

I felt a warm, wet mouth circling my cock. Involuntarily, I began to hump into the mouth around my dick.

A thumb joined the finger on my rosebud, and I was pinched hard, "Do not move, slut," Samuel demanded around my cock.

Trembling, I froze in place.

Samuel returned to sucking my cock and fingering my ass.

"I need to cum, please, Sir. May I?" I pleaded.

"No, you may not!" Was the response.

Samuel held his hand up, "Make my finger wet," he demanded.

I bent over, took his finger in my mouth, and then 'made love' to it like I would have his todger.

Samuel returned that finger to my ass. A few moments later, he offered his finger up again.

Using the wetness I was providing, Samuel was able to lubricate my anal passage enough to slip his finger into my ass. He quickly found my P-spot and began to scrape his fingernail across it.

I didn't think I could stand another second, "Please, Sir. I have to cum."

In response, I received the 'hammer' part of his hand, where the palm joins the wrist, into my aching balls, and Samuel let my throbbing cock out of his mouth.

"You will not ask again, John," he growled. "You will stand still, hands on your head with your elbows back and accept what I decide to give you, and you will cum when I say you can."

"Yes, Sir," I moaned, returning my hands to where I had been told.

My aching balls were massaged, and he took my twitching with the need to cum cock back into his mouth. He held his finger up again. I wet it, and it was soon back rubbing on my prostate.

Samuel gave me fellatio and stroked my prostate for what seemed like forever as I trembled, groaned, moaned, and fought not to cum.

I was desperately holding my imminent orgasm at bay with my knees buckling, and my eyes squeezed tightly shut with my face screwed up when Samuel changed his right index finger for his left middle one.

With his right hand, Samuel let enough of my thick dick out of his mouth to circle the base of my shaft so that he could say.

"You may cum, slut."

Samuel then jammed his middle finger as hard and deep into my ass as he could whilst deep-throating me down to his circled and pulling thumb and forefinger.

I almost literally exploded, "AHHHHHH FUUUUCCKKKKKKK!" I unselfconsciously screamed. "AAAAAAAgggghhhhhhhhh FUUUUUUCCCCCCKKKKKKKK! AHHHH FUCCCCCCCCKKK!

Seriously, I would not have been surprised if my shoes had shot out of my dick. I came that hard. I came so hard and copiously that even an experienced cock sucker like Samuel couldn't swallow it quickly enough. Some leaked back out of his mouth.

Samuel stood up, "Lick your cum off my lips and chin, then kiss me as well as you can", he demanded.

My cock was still throbbing in post-orgasmic ecstasy, and I already felt ready to go again, so I eagerly lapped my juices off Samuel. Then I threw out all my small-town misconceptions and prejudices and kissed Samuel the way I do when I'm overcoming a girl's reluctance to fuck on a first date by kissing her into heaven.

I held his head gently in my hands and touched my tongue to his surprisingly soft lips. I tilted my head to the side and ran my tongue over the corner of his mouth, where the upper and lower lips meet, then across his lips and onto the same place on the other side.

I slid my hand behind his head, held his lips a little more firmly to mine and sent my tongue out to brush his lips, gums and teeth.

Samuel opened his teeth a little wider, and I slipped my tongue between them and into his mouth.

'If I wasn't gay before this,' I thought wonderingly. 'I sure as hell am now.'

Samuel lifted his tongue to meet mine, and we let our tongues dance around each other. Reaching down, I took Samuel's rampantly stiff cock in my hand and tugged it insistently.

Samuel grabbed my wrist, "Show me to your room," he said.

I kicked my shoes off, pulled my legs out of my jeans and briefs, took his hand, and led him up to my room.

"Lube?" He asked.

I indicated the bottle on the dresser.

"Do you want me to wear a condom?"

I shook my head. I wanted to experience the full feeling of this wondrous man's thick 8-inch cock in my ass. I wanted to feel his semen squirting across my prostate, and I was already anticipating cumming to that sensation.