Tranny Babysitter: The Conclusion

"OMFG!" He groaned. "Do that again!"

Holding him in place, I pulled my hips back and thrust into his ass again.

"One more time, Olivia, please," Jonas begged. "One more time, and I'll cum."

I pulled almost out of his ass, leaving just the tip of my rigid dick in his fuck hole, before slamming back into him hard. It was not as hard as I could because I didn't think Jonas could handle it, but it was much harder than I had previously.

He exploded into orbit. "I'MMMMMMMM CUUUUUUUUUUMMMMMMMMIIIIIIIIIINNNNNNG!" He screamed.

His man juice shot up and landed on his face, chin, and throat.

"FUUUUUUUUUUUUUCK YESSSSSSSSSSSSS!" he yelled as I stroked into him again.

More cum was squirted.

Jonas collapsed, and his head fell to the side.

I let my cock slide out of his ass. I still hadn't cum.

Ashamed at what I'd done, I raised my eyes slowly to meet Courtney's.

Hers were full of lust and desire. She held my gaze for a few short seconds and then looked down. My eyes followed hers down. Somewhere in the time that I had been fucking Jonas, she had buckled a strapon into place.

It was huge, at least 9-inches long, thick and purple, and it arced upward. I realised that every stroke would slide across my P-spot if I were on my back and being fucked with it. My mouth went dry at the thought of Courtney fucking me with this giant fake phallus.

Courtney quickly dismissed Jonas, "Call an Uber and fuck off. You can keep the WAG account for now, but I don't ever want to hear you trying to seduce any of Hannah's femmeboys again."

Jonas scuttled from the room.

"Hannah will feed you her ladyboy dick, and I'm going to fuck your slutty ass. If you don't cum at least twice, you will be locked into chastity until the day you or I die. Never to be let out again. Never to be able to orgasm except from prostate stimulation for the rest of your misbegotten life. Do you hear and understand me, my fucking queer-boy husband?"

"Yes, Mistress," I responded. I held my breath in fear and anticipation.

"On your back then, slut," she commanded, much to my relief.

I lay down, lifted and spread my legs, then put my right hand between my thighs and over my balls so I could spread my ass cheeks to expose my rosebud for Courtney's assault.

I watched Courtney spread liberal amounts of lube over and around the strapon's dildo. Satisfied it was lubed enough, Courtney inserted three fingers into my well-used ass before rotating them back and forth as she forced my ring even wider.

Happy that my rear fuck hole was gaped wide enough to take the giant cock she planned on fucking me with, Courtney moved between my spread thighs.

She leaned forward and placed her left hand in the middle of my chest to balance on, then guided the head of her 'cock' to the entrance to my asshole. Moaning with undisguised lust, Courtney slowly forced the giant dick into my ass.

I desperately wanted to impress my wife, so I forced my ass' sphincter to relax and accept the massive intruder that was being shoved into it.

I couldn't help the violent twitch I gave as the large 'head' popped through my inner knot.

I was sure I couldn't take another inch or even a millimetre when the dildo hit my prostate.

My stifled moans of pain turned instantly to groans of pure pleasure and lust. "Yes, please, my Mistress," I panted. "Fuck your dirty slut's cum hole as hard as you want."

Courtney had released her hold on the strapon's 'cock' as more than two-thirds of it was now buried in my severely gaped asshole. She took hold of my cock and began to stroke it. Somehow she had managed to lube her hand, so I was treated to a nice wet handjob as she continued forcing the rest of the strapon into my ass.

The head of a cock was poked at my cheek, so I turned my head and took all of Hannah's long and thin penis into my mouth. Concentrating on the sensations in my ass and on my cock, I tried to make Hannah cum as quickly as possible, so I could focus on achieving the first of the two orgasms that had been demanded of me.

I cupped her tiny smooth balls and started to stroke her perineum as I sucked and swirled my tongue over and around the glans of her cock.

Just as I thought she was about to cum, Hannah pinched my nose shut, making me stop blowing her and open my mouth so I could breathe.

Once she was sure I had lost the path to my orgasm, she released my nose.

I returned to eagerly trying to make her cum.

Courtney had finally forced all her 'cock's' 9-inches into my hugely gaped arse. The shaft of the dildo was pressed exquisitely across my P-spot, and she was gently rocking back and forth but not moving, just a very soft push and pull.

The sensation on my prostate was fucking awesome, and I started to climb the slopes of Mount Orgasmic again quickly.

My nose was pinched shut again.

'Fuck!' I thought. 'It's almost as if Hannah doesn't want me to cum. That she wants Courtney to lock me into chastity forever.'

It occurred to me that that was precisely what Hannah wanted: Me effectively off the scene. Who was more likely to take Courtney back off her other than her husband and the father of her children?

I had begun to believe that Hannah was aiming to take total control of Courtney and me through Courtney so that she could access our money. Perhaps she wanted Courtney and me to break up so she could marry Courtney and eventually get half of everything.

My next realisation, from how Courtney was making love to me and not just sawing into my ass as hard as she could to humiliate me and get herself off, was that Courtney wanted me to cum. She was trying to help me reach her goal so she wouldn't have to put me permanently into chastity.

With this sudden insight, hope surged, and I blew a massive load out the eye of my cock and up across my chest and stomach.

I didn't go even the slightest bit soft. I remained rigidly stiff, and with some stimulation, I'd cum again almost immediately.

"One, fag boy," Hannah said. "But it gets more challenging now because you get no stimulation other than what's in your ass.

Good luck," she facetiously added.

I looked at my wife and saw pity in her eyes.

'Okay, there's something else going on here.' I thought. 'What hold, other than sexual delusion, does Hannah have over her? If she doesn't want to do this, why doesn't she just tell Hannah to fuck off?

Could my wife be being blackmailed into doing this?'

I was determined to win this contest, but I knew the only way to win was to surrender. To give myself body, heart, and soul to my wife. I loved her. I had from the first class we had together at high school years ago. I was sure she still loved me. She just wanted to punish me for the years of infidelity.

"You win, Courtney," I told her. "My life is yours, my body is yours, and my mind is yours. I will gladly live my life as your chastity fagboy slut if that is what you want from me. Do with me as you will."

"Then what you will do for me is cum, my gay, crossdressing, gladly taking homo dick in his arse, husband. You will cum for me right now!"

There's an old saying for exquisite lovemaking, 'The earth moved'. That's how it felt, only it didn't just move. It was shaken to the very core. I came so hard and violently that I was almost surprised the house didn't fall around us.

I was peripherally aware of Hannah removing her dick from my mouth, tucking it back into her knickers, and then storming out of the room.

After coming down from my orgasmic high, Courtney gently slid the giant rubber phallus out of my overstretched ass.

"You're going to catch hell for this," I told her.

"I can handle it. You worry about yourself. You have one more task to complete for me, and then we can try and figure out how to get you out of this mess."

"What task is that?"

"You must recruit one of your teammates to fuck me tomorrow, and it must be tomorrow. You must tell him what you want, bring him home, and encourage him to take me to bed."

"Am I allowed to watch?"

"Through the curtain?"

"No. If I replace the door to the walk-in robe with one-way glass, I'll be able to sit in there and watch you two fuck."

"If you can get it done by tomorrow, sure. After that, you can watch anytime you want."

Courtney left for her room.

I put some headphones on and turned the music way up so I didn't have to listen to her being punished.

I considered the unmarried guys in my team that might like a chance to fuck Courtney and how I would go about convincing them to do her.

I was no closer to an answer when I drifted off to sleep.

Chapter 09: The Second Sunday.

In the morning, I left as soon as I thought the shops would be open. I didn't want to risk being caught by Hannah and forced to do another humiliating task.

It took a bit of searching, but I found what I was looking for and got it cut to size. I wasn't worried about fitting it. I could do that myself.

I bought a jigsaw at Bunnings, some sealant and new mirror trims in case I damaged the ones currently holding the wood panels in place.

When I got home, Hannah and Courtney were gone. Neither responded to my text or answered my call.

It didn't take me very long to remove the two wooden panels and replace them with one-way glass. I found one of the old square padded leather footstools I had inherited from my grandfather out in the garage where it had sat for years, dusted it off, and then moved it inside the closet.

I had to move some more of my clothes down to my room before I could create enough space to sit comfortably. I added some lube and a box of tissues to the walk-in robe.

I walked around the room, and there was absolutely no way of knowing the mirror was one-way glass. A thought occurred to me. I turned my phone on and placed it on the stool.

That you could see.

I thought that I had dodged a bullet there. I was pretty sure the devious Hannah would have waited until whomever I had chosen to be my wife's lover was balls deep in my wife and then called me so he would know I was sitting in the closet watching, further rubbing my nose into my degradation and humiliation.

Having your teammates know your wife is cheating on you is one thing, but they would probably keep that to themselves. Having them know that you were a cuckold and enjoyed watching your wife fuck other men was a completely different story.

Sunday was a lay day, with no scheduled practice, but I knew there would be a few guys at the club in the gym or doing extra training. There were always a few. I was often one of them, so I drove to the club around 4.00 pm.

The gym was mostly empty, but it was only early, and as preseason training hadn't officially started yet, a lot of the guys would have been still partying hard, so I knew it would only be a matter of time before the gym filled up.

Our gym is open to the public. You could become a club member, join the gym, and 'Train as the AFL Players do'. A couple of the footy sluts were already in there 'working out', but mostly trying to get the attention of one of the players and, hopefully, become their wife or girlfriend. Moving from 'footy player's slut' to WAG.

For a change, I didn't even look at them or stop and see if I could talk one of them into giving me a blowjob in the loos.

One of the recruits, Harry, was working the chest press machine trying to add some much-needed strength and weight to his skinny frame. Harry was a bit of a 'pretty boy', and his reputation was that he needed to 'harden up' if he was going to make it at the AFL level.

He was also a known slut, often taking two or even three girls home on his days off. I'd also seen him checking Courtney out when we were out at club functions, but then again, he checked every girl out, and almost every guy checked Courtney out.

I began on the treadmill, just loping along, getting warm. Over the next 15 minutes, I slowly increased the speed until I was flying at almost full speed. I held this for another 5 minutes. It felt good to work some kinks out.

I grabbed my towel and walked to where Harry was working with the free weights.

He was trying to lift way too much. As AFL players, we don't want bulky muscles. We need lean muscle to get over the ground quickly.

As the coach says, "There's no substitute for speed. Speed of leg, yes, speed of mind, better."

"Need a spot?" I asked.

"Yeah, mate, if you could," Harry panted.

I lifted the bar just before he dropped it on his damn fool neck.

"You gotta build up, you know, bro?" I said. "You can't jump from 80 kg (175 lbs) to 100 kg (220 lbs) overnight. You probably don't want to add more than 5 kg (10 lbs) at a time."

I took some weight off the bar, "Try that."

Harry pumped it easily. I added another 5 kg.

By the effort he took, it seemed about right, so I said, "There you go."

Harry was trying to impress. I was a senior if fringe player, so he wanted my approval. He lifted the weight way too many times.

"Hold up, mate," I told him as I had to retake the bar's weight to stop him from dropping it.

I removed the extra 5 kg, "We're trying to add some weight, but not bulk. Bulk muscle is too heavy to run effectively with.

Why don't you try this: 5 presses, rest for 30 seconds, 10 presses, 30 seconds, 15 presses, rest, 10, rest, finish with 5. Make sure you do your stretches and don't do another arm exercise today, do some work on another area, abs or legs, probably.

I watched him work through the sets.

"Good lad."

'He'll do if he wants in,' I thought. 'Wonder how big his cock is.'

"You're from Western Australia, aren't you, Harry?"

"Yeah, mate."

"Did any of your family or friends come over with you?"

"Nah, mate."

"Must get a bit lonely? Are you sharing with someone?"

"Not at the moment, mate."

"Do you know my wife, Courtney?"

"Not really, mate," he answered. "I know she's as hot as fuck, though. Number 1 on the boy's fantasy hit list."

I hadn't heard of this list.

"The whole club has a hot list?"

"Nah, mate, just us new guys. We're all looking forward to building a rep so we can get hot girls like most of you have. Look at you, a fringe player, but with the hottest chick in the place."

He coloured, embarrassed.

"Fuck," he said. "Me and my big mouth. I didn't mean that as an insult, mate."

"None taken. I try, but I just can't seem to crack that full-time spot, ya know?"

"Yeah, mate. Maybe try and do some more of the team things, right? The 1 percenters coach is always rabbiting on about."

"Good advice. I just might try it. But when you get as few opportunities as I do, you need to try and shine in the ones you get, you know?"

"Yeah, but maybe if you do the team things, you might get more opportunities, yeah?"

"You're probably right," I told him. "Anyway, point being, would you like to come home to mine for dinner? Courtney's a pretty good cook, and she does like to wear short skirts in the kitchen," I joked.

"Yeah, all right, mate. That'd be grouse."

"You got clothes, or will we need to go past your place so you can get changed?"

"I was going to head out for a beer after the gym, and I was going to see if one of these slags wants to come home for a root. If she does, I'll buy her dinner first," he said with a smile. "I've got jeans and a T-shirt, okay?"

I laughed, "It's my home, not a fucking nightclub. I just meant, did you need to get out of your sweaty gym clothes?"

"Oh. Nah, I'll be good. I'll grab a shower here. Do you mind if I catch a lift with you? I don't have a car yet."

"Sure," I said. "Let's finish our routine, shower, and head to mine."

"Sounds good, mate,"

About 30 minutes later, we were in the showers.

Now, ladies, we don't look, okay? You just don't. Not unless you want a punch in the face. So I had to be very discreet in checking Harry's tool out.

He looked like he was carrying a pretty standard 6-inches or so, not thick, nor thin, just, well, standard.

'She'll love that in her arse,' I thought, then had to flick my thoughts to somewhere else quickly before I went hard.

On the way home, I said, "Listen, mate, I don't want to shock you, so if you're not into it, say so ... "

"I'm not gay, mate," Harry interrupted.

"What? Oh. Neither am I," I lied, but was I? "No, not that. Our babysitter is staying with us, at the moment, troubles at home, I think. She's as hot as hell, and I'd like to fuck her, you know?"

Harry nodded his head.

"So, if you can get Courtney into bed, I'll be able to fuck the babysitter, yeah?"

Harry looked at me, "You want me to bang your wife so you can bang the babysitter?"

"In a nutshell, yes."

Looking doubtful, Harry said, "That's fucked up, man. Your wife is as hot as all fuck, so if you'd rather fuck your babysitter, your babysitter must be like, Gal Gadot or something."

"More like Jennifer Lawrence, but I hear you. Listen, mate, if you're not up for it, I guess I can see if one of the others is."

"And you're not going to freak out or anything? Try and punch me in the face for touching your wife?"

"Nah. If you fuck her well, and she loves it, she might even let you do it again. I'll tell you what. After I've fucked the babysitter, I'll send her into you, and maybe you'll get to do her and Courtney at the same time."

"You're bullshitting me. There's no way you'll let me do it. This is some kind of initiation thing, isn't it? Testing how loyal your new teammate is?"

"It's up to you, Harry," I said. "Squeeze Courtney's ass, see how she reacts. Take it from there."

"So you're telling me you're married to a chick that looks like young Courtney Cox and have a babysitter that looks as hot as Jennifer Lawrence, and you want me to bang Courtney Cox so that you can fuck JLaw?

You know I'm going to, John, right? If she slaps my face or freaks out, I'm going to punch you in the face, and you'd better grow eyes in the back of your head cos I'm going to fucking smash you every time you sit under the high ball from then on," Harry warned me.

"And the babysitter's as hot as Courtney?"

"It's a close-run thing, you know? If Courtney's a 10, Hannah's like a 9.995."

"Fuck!" he said. "And you don't get jealous?"

"You know how many of the footy sluts I've fucked, Harry. You've even fucked some with me. How big a hypocrite would I have to be not to let Courtney have some fun?"

"Does she get it on with the babysitter? Cos fuck, that would be fucking hot."

"I guess you'll have to ask them and find out, won't you? But I doubt you'll be disappointed."

"Shut up! I'm getting a fucking woodie. You're not a fag, or anything, are you? You're not going to want to get it on with me after I've done your wife?"

"Nah, mate. It's strictly pussy only for me," I lied again. "I just need someone to take care of Courtney so I can safely bang the babysitter and not get in trouble."

"You're fucked up, man. But I'm game if the girls are up for it."

"You can't go bragging about it after, however. If I hear any rumours whatsoever, you're off the list, and none of us ever talk to you again."

"All good, mate. You never tell about banging a teammate's wife. Not unless you want to find yourself on the transfer list."

I glanced across at Harry. He was looking out the window, so I snuck a quick glance at his groin. It was severely tented.

I felt a frisson of excitement at the thought of watching him use it to impale Courtney's ass.

We arrived home, "Ready?" I asked.

"Yeah, mate. This had better not have been all bullshit."

"I guess you'll see, right?"

He nodded.

Courtney was in the kitchen, wearing a sheer blouse without a bra. Her nipples were hard and clearly visible through the blouse's material. She was wearing a slightly longer skirt than I expected, but then I remembered that she was probably wearing even more bruises on her ass than before after being punished for her latest indiscretion.