Chapter 8: 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?’

I looked in the drawer and brought the box out. It took five different tries, but the padlock suddenly released, and I could take the cage off.

I lay down on what used to be our marital bed and tied to have a wank. I got as rock-hard as ever but couldn’t quite get over the edge. I tried imagining fucking Courtney, fucking Hannah, fucking Roger, being fucked by Roger, being fucked by Samuel, same, same.

It was great, but I still couldn’t pop over the edge.

I imagined fucking Samuel. I got close but couldn’t quite get there.

Feeling as horny as all fuck, and as frustrated as a mime artist in front of an audience of blind people, it occurred to me that I came really hard when dressed as Olivia. Maybe that would get me there.

I went to my room and selected the sluttiest outfit I could find. It was a dark blue ultra-miniskirt, barely two hand widths in length. When I tried it on, my hard and thick cock showed at least three inches over the top of it.

I got out my skimpiest thong, a tiny lime green number, and a matching bra. My balls hung lewdly on either side of the front piece, and the string was between my butt cheeks.

A package had been placed on my dresser on Tuesday morning. When I opened it, I found a breast chest plate. This item was to be worn almost like a T-shirt. It was in a natural skin tone and fit over my head and down across my back and chest. The breasts on it were so enormous that they would barely fit in my bra.

Eagerly, I donned it and then adjusted it until it sat evenly and smoothly on my upper body. I gave the breasts an experimental squeeze. They weren’t going to fool an experienced lover, but they might just fool an inexperienced one, especially on a woman as hot as I was planning on making myself.

I sat at Courtney’s vanity and did my face to the nth degree, using every ounce of the skills Roger/Rashida had taught me. Once satisfied, I looked as hot as I could make myself. I got out the 7-inch stiletto heels with the platform soles the girls had bought me.

My ‘whore heels’, Courtney called them. They were for a casual sexual encounter where I didn’t care if the man I was going to let fuck me knew I was a tranny or not. It was probably preferable that he did know and didn’t care.

I practiced walking in them until I could do the toe-in-front-of-heel walk Hannah and Courtney had shown me, and Hannah had insisted I learn.

Once I was sure I had the walk down pat, I chose a top. Settling on a lime green to match my bra and thong set, a string-strapped backless number that would barely cover my enormous breasts, I put my bra on and then strapped the top into place.

‘Looks silly with the bra,’ I thought. I undid the shoulder strings of my top so I could take the bra off.

Tying the top back into place, I checked myself out in the full-length walk-in robe door mirror in Courtney and Hannah’s bedroom.

‘Hot as fuck!’ I thought. ‘At least from the neck down.’

I even loved how my precum-leaking cock looked poking out of my skirt.

I was leaking so much precum that I had to keep a facecloth close to wipe up the dribbles before they dripped onto my skirt, and I would have to change.

“If a ladyboy looking like this had approached me on those end-of-season trips to Bali, I would have sucked a dick years ago,” I told myself.

I turned back and forth, admiring myself in the mirror. My ass was fantastic, and my calves popped.

‘At least a 10 from the neck down,’ I thought. ‘Maybe a 7 with the face added in.’

As I looked into the mirror on the bedroom’s built-in closet’s door, another thought flew through my mind.

‘If I put a one-way glass in this door, I can sit there and watch Courtney being fucked without ever being caught.’

I made a mental note to ask for the girl’s permission when they returned on Sunday.

My plan tonight was to go out and be picked up. I knew, as soon as I had a penis scraping across my prostate, that I would orgasm numerous times, whether I could take the tape off my balls or not.

There was a huge problem, however. I couldn’t make myself go soft enough that I could tape my balls and shaft away. My lust was raging, and I needed to cum so horrifically that I would throb until I did.

I tried to masturbate again, but still no luck. In desperation, I set up the fucking machine and rode it for about 10 minutes and was just about to cum, when there was a sizzle, a smell of burnt wiring, and the motor gave out.

“Fuck no!” I screamed in frustration.

I fucked myself on the dildo, but the sensation of cumming had gone, and I couldn’t get back up there.

My cock was still rampantly stiff and was still throbbing with my desire. My balls were aching.

I couldn’t figure out what the issue was. I had my choice of visions, women, men, women and men at the same time, men and men at the same time, women and women with men and men at the same time, but I just couldn’t get over the edge.

I went to my computer and brought up some lesbian porn, something that has always gotten me off before. I still didn’t find fruition. I switched to gay porn, but it didn’t do anything for me at all. In fact, I even softened some.

‘That will work,’ I thought. ‘Soft is soft. It doesn’t matter how I get there. Once I’m taped into place, it won’t matter how hard I try to go the tape will hold it down.’

I looked at the worst gay porn I could find. I know, I know, each to their own. If watching hairy 300+ pound (135+ kg) gay guys going for it is your thing, help yourself, but it sickens me.

It did soften my erection for as long as I kept watching. But as soon as I stopped and tried to tape myself into place, my erection returned. It was as if my fucking dick had decided to help Courtney and Hannah by not letting me out of the house.

I took my shoes, skirt and knickers off, filled a bowl with iced water from our fridge, and then turned the gay porn back on. Once I had softened some, I poured the ice water on my crotch.

Success! I was soft. But as soon as I took myself in my hand to tape myself away, I began to go hard all over again.

I was just going to admit defeat, accept that without Hannah’s or Courtney’s permission, I was never going to cum again when it finally occurred to me that I knew four guys that don’t care that I’m male, and would probably want to see, and to fuck me.

I didn’t have a phone number for Bryce, Roger would be out with Hannah, Samuel was gay, attracted to the masculine, and I didn’t want to present that way, so that left Jonas.

I practiced my voice for a few minutes, recording it and then playing it back. Once I was happy it was as feminine as I could currently make it, I got out his card and phoned him.

Jonas picked up immediately. I could hear dance music blaring.

“Hello?”

“Hello, lover,” I mouthed breathily. “Remember me?”

“Can’t say that I do.”

“You fuck me, make me pregnant, and then tell me you don’t remember me?” I hummed.

“Listen, honey, I don’t know who you think I am, but I’ve never fucked a woman in my life. You’ve got the wrong number.”

“It’s Olivia, Jonas,” I told him in my normal voice.

“Olivia? Who the fuck was on before? Was it Hannah playing a joke?”

“It was me, Jonas. I was having some fun at your expense.”

“In a week? You got your voice to sound like that in a week? Leaps and bounds, baby girl,” he told me. “You’re progressing in leaps and bounds.”

Cutting to the chase, I said, in my ‘Bea Arthur’ voice, “So, baby, do you still want to fuck me?”

“Come to The Beat,” he said. “Text me when you’re inside. I’m about to have my cock sucked. See you soon.”

‘Damn,’ I thought. ‘Now what?’

Then I remembered that The Beat has literally dozens of transgirls, drag queens and gay guys pouring through it. As long as I covered my naked cock up, for as long as it took to get to the dance floor, nobody would give a fuck.

I found a jacket that I could tie around my waist to hide my dick, clipped the wig Jonas had moulded for me on, called an Uber, and went out.

I joined the line-up outside the entrance to The Beat about 20 minutes later. The guy behind me kept nudging my ass with his stiff cock. I probably wouldn’t have minded, except he was gross, you know? Way overweight, smelly, and as hairy as fuck.

Turning around, I said in my usual voice, “You’re about to be bitch slapped by a 6 ft. 4 in. (193 cm) tranny in front of all of these people. What the fuck do you think you’re going to do then?”

The guy made a run for it.

The line applauded me. Apparently, he had been doing it to a number of the girls, cis and trans.

My ID was noted, and my picture was taken. They didn’t care that my name and the photo didn’t match my appearance, and I was inside.

I phoned Jonas, “I’m here,” I said, using my new voice when he answered.

“Wait there, and I’ll come and get you,” he replied.

Jonas came down the stairs from the higher level. He took my hands in his and then kissed me.

“You look fucking fabulous, darling,” he lisped outrageously. “But what’s with the jacket around your waist? It’s like 30° (86f) fucking degrees outside, more in here.”

“I’m so fucking horny that I can’t get rid of my erection,” I informed him. “If you don’t take me home and fuck me until I can cum no more, I swear my balls are going to fucking explode.”

Jonas slipped his hand inside my tied jacket and stroked the head of my steel-hard dick.

“Well, why didn’t you tell me? I would have cum straight over, literally.”

“You were about to get your cock sucked, remember? You hung up on me before I could invite you.”

“A new girl,” he dismissed airily. “All enthusiasm and little skill.”

“You gave her a load, though, didn’t you?”