Tranny Babysitter: The Conclusion

"From behind or on your back like the bitch you are?"

I stripped my polo off and lay on my back with my knees raised and apart. I just couldn't imagine not kissing him as he fucked me. It would be so much more intimate.

Seeing that I was completely hairless from the neck down, Samuel took an intuitive leap, "Get your girliest thong out of your drawer and put it on for me."

I quickly donned an electric pink one that Hannah had chosen for me.

I adjusted it so that the string was between my ass cheeks and across my hole, the front was covering my balls, and my long cock was poking lewdly out the top.

"Very nice, girlie-boy," Samuel said. "You ready to be fucked?"

"Yes, please, Sir," I begged.

Samuel put lube on his middle finger, moved my thong aside, and gently inserted it into my ass. Working quickly, he added more lube and a second finger. Forcing those two fingers apart, Samuel rotated them slowly around my ring to stretch me wide enough to take his thick, almost 8-inch rod.

Satisfied, he lubed the head of his cock and the length of his shaft before kneeling between my spread thighs and close to my lifted ass.

Holding the back of my left knee, Samuel positioned the head of his beautifully thick penis at the entrance to my hole.

Pushing on my knee, he lifted me a little higher and then pushed his hips gently forward.

With a grunt from me, he popped through my knot and deep into my ass. The head hit my prostate almost immediately through my knot, and I gave out an ecstatic groan.

"You've obviously been well fucked in the ass, my boy," Samuel told me. "But you're still deliciously tight. I will show you some exercises to make sure you stay that way. You won't want to be my age and be too scared to fart in public in case you make a mess."

Samuel began to rock his hips back and forth, rubbing delightfully across my prostate the whole time.

Samuel was still upright as he fucked my well-lubed ass. He took my diamond-hard cock in his hand and began to stroke me.

"You will not cum until given permission, little one," he said.

I moaned in frustration as I already needed to cum very badly.

"If you let me cum, I promise I'll be able to go again very quickly, Sir." I pleaded.

"I do not wish to debate things with you, John," Samuel said harshly. "You are my toy to do with as I please. As my toy, your role is to do what you're fucking told."

"Yes, Sir," I acquiesced, trying not to cum to the delicious mind fuck of being dominated.

Satisfied with my obedience, Samuel began to fuck me again.

All I could do was screw my face up again and desperately struggle to stave off my almost overwhelmingly urgent need to orgasm.

Samuel's stroking started to heat up, and I could hear from his grunts and pants that he was surging close to orgasm. I was looking forward to feeling him spit his load into my gaping arse.

The problem was, as he fucked me harder, he stroked me more firmly and more insistently. I didn't know how to keep from shooting my jism between us.

Samuel seemed to instinctively know when I had reached the end of my endurance because, for the second time, just as I was about to lose my load despite being told not to, he released me from the no cumming prohibition.

With a deep, strangled groan, Samuel let go of my shaft, fell onto my chest, kissed my surprised lips and began to unload into me.

"Cum with me, boy," he instructed.

My cock burst its gooey essence between us as Samuel spurted over and over into my ass. His second, third, and fourth shots squirted deliciously over my prostate, and I spasmed cum in time with his cock's splashes.

Samuel rolled off me onto his back. Having been taught well by Hannah, I took his now flaccid cock in my mouth and began to suck and tongue him lovingly clean.

"She does train her boys well. I'll give her that," Samuel moaned as he began to harden in my mouth and hand.

Shocked, I stopped, "I thought you said you didn't know her?" I asked, dreading to hear that I'd been set up again.

"I don't. Not personally. I just know her by reputation."

"So this isn't another of her fucking setups?" I questioned, a little angry.

"No, John, it isn't. When you said who your mistress was, I nearly backed away. But you're so willing and eager to please that I just couldn't help myself."

Samuel was now rock-hard in my hand. I had subconsciously kept stroking him and fondling his big balls as I questioned why he was here.

"I want you to fuck me this time, John," he moaned. "Tongue my ass and get me ready. I have sex regularly, so I shouldn't need much stretching, just wetting and preparing."

"I don't want to," I muttered.

"You think you're a total bottom with men, John?" Samuel laughed. "You're kidding yourself still. Baby boy, you will do as I say or be punished."

"If you think you're strong enough to punish me, go right ahead," I challenged.

The lights were flicked on, and brightness flooded the room.

"You will fuck him, fagboy," Hannah demanded. "And you will cum in his ass. You're already going to be punished for disobeying."

Samuel sat up, seemingly unfazed by the sudden intrusion, "Hello, Miss Jovovich," he said in his deep urbane voice.

He turned to Courtney.

"And you must be his wife and Mistress, Courtney. Nice to meet you, my dear."

I could have sworn Hannah paled before taking control of herself. Strangely, she turned both cameras to the wall and put her phone in her handbag.

"This is your slut to sort out," she said to Courtney. "You should know what to do by now. I'll meet you in our room afterwards."

She hurriedly left the room.

'Interesting,' I thought. 'I wonder what power Samuel holds over her.'

I felt a faint hope that I could escape the trap I had been so severely caught in. I was sure if I could get Courtney alone and get Zac to tell her what he had heard, she would get rid of Hannah for good.

I determined to call Samuel when I was next alone.

Courtney looked a little baffled at Hannah's sudden departure, but she quickly took hold of herself and seemed eager to continue my subjugation.

"Where were we? Oh, yes. You were about to prepare your lover's ass for your cock. Get to it, my little fagboy husband."

With my wife's dominance over me fanning my flagging arousal, I turned back to Samuel, touched his shoulder to encourage him to roll over, and then started to tongue his rear passage.

Samuel was right. Once I had his rosebud slippery with saliva, my finger penetrated him easily.

With my wife watching, I wanted to put on a show. This act seemed different without Hannah there. I wasn't an unwilling participant being forced to make love to a man because Hannah's dominance had overcome my natural reluctance with the lust her domination of me had inspired.

I was doing it this time because my dominant wife, my Mistress, told me to.

I eagerly tongued the cleft of Samuel's ass, reached around his hip and took his rigidly hard tool in my hand.

I tongued him, stroked him, and worked my finger deeper into his arse simultaneously.

Hooking my finger down and a little back, I found Samuel's P-spot and rapidly swirled my middle finger over it. He rewarded me with a deep and guttural groan.

"I'm ready for you, my baby boy," he moaned. "No need to be gentle, fuck me like you mean it."

I quickly covered his body with mine, positioned my cock's head on his ring, then viciously shoved into him, just like I used to into some slut's cunt that I had teetering on the edge of orgasm from the oral stimulation I had given her.

I reached around and grabbed Samuel's thick shaft again.

Samuel reacted in almost the same way as those sluts did. His head fell back, then forward. He groaned deeply and lustfully, then pushed his ass back at me.

"Yes, baby boy, fuck your daddy's ass as hard as you can." He mumbled. I could feel his cock about to explode in my hand.

'Whatever floats your boat,' I thought, then did what I was told. I pounded him with everything I had.

"Fuck, this is so hot!" Courtney moaned.

She had hoisted her skirt over her hips, pulled her knickers down, and had two fingers jammed deep in her pussy. Thumbing her clitoris as I fucked Samuel, and she rogered herself, Courtney quickly arrived at the point of her orgasm.

"Cum in his ass, and I'll cum with you, honey," She said, calling me by a loving name for the first time since she forced me onto this journey.

It was too much for me. My cock erupted.

"Fuck, fuck, fuck, fuck, fuck," I groaned over and over again as I spurted into Samuel's ass, my swearing in time with my cum spasms.

Samuel came with us. I could feel his cock jumping in my hand and his ass clenching down on my now super sensitive cock head. This caused me to cum several more times.

Seeing me cum into Samuel sent Courtney off into orgasmic heaven. She shoved all four fingers into her tight, slippery cunt, slapped her clit with her other hand, and squirted over her fingers. The first time she had ever squirted for me.

In an almost daze, Courtney left the room and shut the door.

A short time later, I heard the unmistakable sound of an ass being paddled. It wasn't going to Hannah's, so that meant Hannah was punishing Courtney or maybe rewarding her. I wasn't sure.

What I did know was that Courtney didn't like pain. I had to be very careful when I nipped her clit or nipples during our lovemaking because I could turn her off in an instant if I were even the slightest bit too rough, so I doubted Hannah was rewarding Courtney.

'She may have made a mistake there,' I thought and wondered if I couldn't use it to my advantage.

Samuel rolled onto his back. He still hadn't excreted a lot of cum, but he had made quite a mess on the sheets.

Being the good boy I was, I went down on him and took him back into my mouth to clean him up.

I also hoovered all the semen off his stomach, abdomen, thighs and balls.

I expected Samuel to immediately get up and leave now that he had been satiated, as that had been my experience.

Instead, he said, "Come and spoon with me, baby boy. I need to sleep."

I lay on my right side with my ass pushed back. Samuel snuggled into my back and pushed his soft cock against my ass. He reached around, took my dick in his hand, and then kissed the nape of my neck.

Happy, I drifted off to sleep.

Twice during the night, I felt Samuel's hard cock pushing into my ass, it felt nice, and he didn't seem to need me to do anything but accept him into me, so I lay there, silently, and clenched down on his shaft with my ass as he slid backwards.

He came quietly into me both times. I could feel his fluids leaking back out of me after my second fucking.

Chapter 08: The Second Saturday.

I woke up in the morning alone. There was a card propped up on my dresser. I picked it up, and it read:

Samuel Brooks

Queen's Counsel

There was a law office's name, address and number underneath that, along with Samuel's mobile number.

He had written on the back: Give me a call when you need to talk. Do it, baby boy. I can help you.

He had signed it with a flourishing 'S'.

I got up and entered the en suite to turn on the shower. I caught sight of myself in the mirror and turned to look into my own eyes.

"Fucking fag," I told myself as tears filled my eyes. "Can't be a man for your wife, can't be a man for your kids, and can't be a man for your team, just another useless fucking queer."

I told you, those small-town prejudices run deep.

Please don't get me wrong here. I don't have any problems with men, or women, for that matter, being gay, even though it sounds like I do. I have teammates, who may not be openly gay because of the small-mindedness of some within the AFL community I know to be homosexual, and I have no problem sharing a changing room with them or showering at the same time as them.

Nor did I fear that they would hit on me or that their 'gayness' would rub off on me and make me gay, too. I just didn't want to be one. I loved my wife and wanted to spend my life with her, and I couldn't see how that could work if I was gay and couldn't give her the kind of love she needed.

I showered last night's sex off of me and washed my hair. Without really thinking about it, I checked my armpits and pubic area to see if any stray hairs had grown out.

I had been instructed to keep myself clean of hair from my eyebrows down, and I feared the punishment I would receive if Hannah found any hair where she had said there shouldn't be,

The wax job seemed to be still keeping me clear of hair.

I cleaned my poor abused ass and tried to check to see if my starfish had been too severely stretched. The problem was that I hadn't looked before, so I had nothing to compare. It still seemed to close firmly shut, though, so I hoped that meant it hadn't yet been forced out of shape.

I used one of the enema kits to clean inside, just in case.

I even added some lube, again, just in case.

Sipping coffee, I researched 'anal exercises for gay men' and found an excellent site that explained how to do Kegel exercises to ensure my ass' sphincter stayed tight and supple.

I sat there drinking and doing them.

Courtney came in, saw me, and walked over.

She gave me a light kiss, it was heaven, but then she ruined it all by saying, "Morning, my arse fucked fagboy husband."

In despair, I let my hands drop from where I had carefully placed them on her hips in a non-sexual way. My fingers brushed across her tight ass, and Courtney gave a quick suck in of breath as she winced.

"I'm going to head out to the farm. It's been too long since I saw my brothers, mum, and dad. Mum wants the boys for the week, so I'll leave them out there."

Courtney's mum and dad owned a combined wheat and cattle property outside Stanthorpe. I hadn't told her yet that her dad had offered the farm to us upon my retirement. Neither of her brothers wanted to run it. They had both taken city jobs after completing their uni studies.

It was a good property, turning a healthy profit most years. 'It's perfect,' her dad explained to me. "We're just getting too old. In the wet years, we sell the wheat at the end of the season. During the dry years, we use wheat to feed the cattle. We have a solid bore that provides more than enough water to grow the wheat and keep the cattle watered, so we're not reliant on good weather or water grants."

I planned to cut back on the area set aside for cattle and grow some grape vines. I'd been doing some courses to begin making wine when I retired.

Courtney was really a country girl at heart, and I knew she would love to move back to the family farm when my career ended.

Or, at least, she did until Hannah arrived on the scene. Now, I didn't know what she wanted other than to humiliate and subjugate me.

"I'm dropping Hannah off at Roger's on the way," Courtney added. "She, and all her femmeboy fags, have something planned for the day, so you'll have all day to do yourself with your machine. You have my permission to fuck yourself as often as you want.

Oh, by the way, stand up and spread your legs."

She handed me the cock cage she'd been holding behind her back.

I was made to unlock it, place it on myself, lock it, and then hand the key back.

"Good slut," she told me, then patted my face. "Now fuck off out of the kitchen. Hannah and I are going to fuck on the bench one more time before I leave for the farm."

Completely demoralised, I went back to my bedroom.

About an hour later, my phone dinged with a message. I looked. It was from Courtney. I opened it in the vain hope that she had decided to ask me to come with her.

There was a message above a 4-minute video clip, "Maybe this will help you to cum, fagboy. Or is watching a woman getting fucked no longer a turn-on for you?"

I pressed play on the screen.

Hannah had done the recording as she held my wife's wrists together behind her back with one hand. Courtney was bent over the kitchen bench.

I watched, fascinated, as Hannah lifted my wife's gown, exposing her badly battered ass. Hannah had paddled Courtney quite viciously last night as the marks were already turning black and blue.

With my cock trying to harden in its cage, I viewed Hannah's long thin cock sliding ever so slowly into my wife's delectably tight rear passage. I listened as Courtney groaned lustily and begged to be fucked harder and faster.

The recording became increasingly jumpy as Hannah started to fuck Courtney harder and harder in response to my wife's demands.

The video ended with Courtney creaming on Hannah's long tool and Hannah smacking her raw and tender ass to make her turn around and receive Hannah's load all over her pretty face.

Moaning with need and desire, I got the fucking machine out, cleaned and lubed the dildo, and then oiled my ass up so I could let it delve deep into my anal cavity again.

I got the positioning right the first time, and the dildo was soon sliding deliciously over my prostate, but it seemed less than before. It was great, and if I had all day to enjoy it ... well, I guess I did have all day, but I wanted to orgasm more than revel in the feelings ... it would have been fantastic, but it wasn't fulfilling my needs.

I tried turning the speed up and down, but nothing changed, it was nice and would have slowly brought me to the edge, but I wanted to cum now. I tried letting it fuck me at full throttle, but that was just pain. I tried turning it off and fucking myself back and forth on it, but that wasn't doing it either.

Frustrated, I tried turning it back on again. There was still not enough stimulation for me to cum. I was about to give up when the green light on the doorbell-type cam turned on.

"There's a good fagboy," came Hannah's powerful voice. "Did my ass fucking your wife make you all hot? But what do you imagine, my little queer? Fucking your wife's slippery, tight, gripping ass, or me fucking yours?"

At the exact point of Hannah saying '... or me fucking yours?' a vision of being on my back, with my legs tethered to a spreader then tied to my handcuffed wrists and Hannah slowly penetrating my tight but willing ass burst across my vision.

My cock exploded into orgasm, and I shot blast after blast out of my mostly flaccid cock's eye.

"Fuck me, what a fag," came Hannah's mocking voice. "If you're a very good boy, and slide across the floor on your naked body, like the lowly worm that you are, then get on your knees to suck me to orgasm, I may let Courtney get you off by fucking your arse with a strapon. But not until I get back late on Sunday.

Of course, I'll have to service your lovely wife first, so I might let you watch me do that."

The light turned off.

Visions of being pegged by Courtney played through my mind all day. No matter how often I told my cock that trying to go hard in its cage was a stupid idea, and no matter how often I told my balls that aching with the need to cum, when I couldn't get hard was pointless, I still throbbed with desire, and still ached with the need to cum.

I tried the fucking machine again, but it just wasn't bringing me to fruition quickly enough. I schooled myself to wait for my prostate orgasm to rise to fruition, but 45 minutes later, I got up and tried a cold shower.

That didn't help, either.

I considered going to the hardware store and getting a bolt cutter to take the cage off, but I feared what Hannah would do when she found out. I thought of going to a sex store and buying another device, hoping the key would work on mine, but the padlock on the device looked like a perfectly standard padlock to me, and I doubted another key would unlock it.

Around 5.00 pm, after another fruitless attempt to use the machine, a thought occurred to me. 'Courtney has a little box in her bottom drawer where she puts all the spare keys. She wouldn't have casually thrown the second key to the padlock in there, would she?'