Tranny Babysitter: The Conclusion

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?"

"Why, yes, I did," he said. "Even a bad blowjob is better than no blowjob."

"I don't give bad blowjobs," I informed him. "I give fucking awesome ones. Want to see?"

"Fuck, yes," was the response.

He took my hand and guided me up to the dancefloor.

It was fucking fantastic dancing with someone who could actually dance.

Jonas took my hand in his, put a hand immediately on my ass, squeezed it, and then led me through a series of dance moves.

I moved effortlessly with him. Courtney and I have learned both Zamba and Samba. The difference is slight but noticeable. What Jonas was doing was easy, in comparison.

Jonas switched to tango, and I followed that easily, too. The DJ noticed that we had created a circle of admiring patrons around us and increased the speed of the songs he was playing.

Jonas began to improvise, trying to put me off my game.

"Anything you can do, I can do, backwards and in high heels," I told him.

Thirty minutes later, Jonas kissed me, then whispered in my ear, "Let's get out of here. I need to fuck you so badly."

We raced downstairs and into a cab.

Using my 'Bea Arthur's' voice, I said to the cabbie, "I'm going to blow my partner on the way home. Do you want us to sit in the middle so you can watch?"

"Any chance of getting one, too?" He cheekily asked.

I examined him in the rear-view mirror, "No," I decided.

I slid over so that Jonas could sit in the middle, bent over, undid his fly and pants button, fished his rigid tool out of his underwear, and then went down on it.

Jonas was a nice 7-inches long. Neither thick nor thin. Just about a perfect length and width for anal sex, I decided.

I swallowed his entire length in one fell swoop.

The cabbie groaned, "Fuck, what a slut."

I preened under the praise and started bobbing my head up and down Jonas's cock. I delved my hand back into Jonas' pants and carefully brought his balls out so I could caress them.

Showing off to the cabbie, I swallowed, released, and then ate all of Jonas again and then again.

The cabbie took his tiny dick out of his pants and began to toss off as he drove us.

I showed my forefinger to the cabbie in the mirror, lifted my mouth off Jonas long enough to swallow, dribble spit over it, and then slipped my hand between Jonas' upper thighs so I could rim his ass.

"Where do you find a slut like that?" The cabbie asked. "I'd love to meet one."

"You can't beat a transgirl for good headjobs and easy sex," Jonas groaned.

"That's a fucking tranny?" The cabbie moaned in disbelief. "Bullshit!"

I pulled the arms of the jacket I had tied around my waist apart, exposing my rampant erection.

The cabbie turned back at the next red light and tried to stroke my hard dick.

I slapped his hand away and let Jonas out of my mouth long enough to say, "You may look and wank yourself, but you're not to touch."

Jonas came just as the cabbie turned into my driveway. I took all of his ejaculate into my mouth, lifted my head so the cabbie could see, opened my mouth to show him it was full of Jonas' cum, closed it then swallowed.

I opened my mouth long enough to show the driver I had swallowed everything.

The cabbie jerked brutally on his tiny dick a few more times, covered his cock's head with a hastily pulled hanky, and then came into it.

I held my hand out. Wonderingly, he placed his cum filled handkerchief in my hand. I opened it and then licked all of his cum out of it.

The cabbie was a smoker, and his semen was bitter. I swallowed it down, regardless.

"Fuck me, mate," he said to Jonas in wonder. "You've caught yourself a right slut here. Strange though, I thought this was John Murray, the AFL player's house. He must have moved."

'Just my luck to have gotten a cabbie that had taken me home before,' I thought.

Jonas and I raced up to my bedroom, and I quickly dropped onto my back on the bed.

Jonas lifted my legs and ripped my thong off. He dived down onto my cock and roughly shoved two fingers into my ass.

Although I'd been fucking myself on the machine all day, so I was well stretched, my ass was dry.

I opened my mouth to protest, but his fingers found my prostate.

Instead, I groaned, "Fuck yes, Jonas. Make your little slut girl cum."

Jonas circled my ball sack with his thumb and forefinger and forcefully pulled my balls away from my shaft.

"You'll cum when I say you can," he growled.

This is what I wanted, what I needed, I realised. I hadn't been able to cum because I wasn't being dominated. I wasn't being forced to do things outside of my comfort zone. Masturbating was something I'd done, like forever. Without someone dominant guiding me, forcing me, I could no longer get there on my own.

I craved my dominant's approval and permission. I remembered how quickly and easily I had cum when Hannah had spoken to me earlier this day. Cum hard and fast, even though I had struggled before the moment the cam's light turned green.

Jonas pulled his two fingers out of my ass and then offered them to me to make wet. Glad that I had used the enema kit earlier, I sucked and tongued those two fingers as if it was his cock.

They were slid back onto my prostate.

A short time later, Jonas groaned, "You ready to take me, baby?"

Irritated, I peeved, "Just take me. You don't need my permission,"

I didn't want him to ask permission. I wanted him to say, "I'm going to fuck you now," and then fuck me until we both came.

Jonas gently entered my ass and started to slowly fuck me. I wrapped my legs around the back of his calves and tried to pull him into me faster, but Jonas wouldn't take the hint.

"Fuck me, Jonas," I pleaded. "Fuck me like I'm the dirtiest whore in the entire world."

But he wouldn't. He was 'making love to me', I realised. I didn't want him to 'make love to me'. I wanted him to slut fuck me.

'What's the point of going to all this effort to make myself into the hottest 'gagging for it' slut on the planet if all my man is going to do is gently make love to me?' I thought.

Jonas was being too gentle, too considerate, and I still couldn't quite get over the edge into a blissfully orgasmic state.

"Fuck me, honey," I begged. "Fuck your slut girl like you want to pound her into next week."

"I will, my lovely," Jonas assured me, but he didn't.

He continued to try and gently lead me up the slope to Mount Orgasmic, whereas I wanted him to whip and flog me up that slope, driving me higher and faster than I had ever been before.

I changed my voice to my normal one, "Jonas, if you don't start fucking me like the slut I am, I'm going to roll you over and fuck you."

"That sounds like a plan," came Courtney's voice from the door cam.

My bedroom door opened, and Hannah and Courtney walked in.

You'd think, by now, I'd have figured out these two bitches were always a step or two ahead of me.

Courtney shook a bottle of pills in front of me, "Just one of these, and it makes you as horny as all hell but won't let you cum," she smirked. "I slipped one into your tea when I gave you that kiss this morning. You didn't even notice.

I left the key to your cage where I knew you would find it, dropped the boys out to the farm, and then came back to town to wait to see what you would do.

I hoped you would call Samuel because that would confirm you were gay. Instead, you dressed like a two-dollar fucking whore, and phoned my pooftah hairdresser."

She turned to Jonas, "And you, after all the business I turned your way using my position as WAG Queen, what do you do? You fuck my fag, crossdressing husband behind my back.

Well, Jonas, you're going to make it up to me. You're going to let my homo husband fuck you in the ass."

Chagrined, Jonas said, "I don't take, Courtney. I'm strictly a giver. You know that."

"Like I give a fuck what you do or don't do," Courtney vehemently told him. "I'll give you one last chance, Jonas. Let my poof husband fuck you in the ass, or I'll take all of the WAGs to another hairdresser, bankrupting your business at the same time. So, what will it be?"

Watching my formerly demure and self-effacing wife dominating the world had me even hotter than before. I firmly believe I could have drilled for oil with my red hot todger.

Jonas crumbled. What else could he do?

He turned to me, "Fuck me, Olivia, please," he pleaded. "Without the WAGs, I'm done. 90% of my clientele are either WAGs or come to me because the WAGs do.

Something weird was happening. I hadn't wanted to fuck Jonas. I had wanted him to fuck me, but he was shit at it. I'm sure new transgirls would have loved his gently, gently approach, but I didn't want that. I wanted, nay, I needed to be fucked, not made love to. But now, I wanted to do what my wife had demanded. I wanted to fuck this pathetic gay slut.

"Roll over onto your back," I roughly told him in my usual voice. "Lift your knees and spread your ass cheeks. I'm going to dry fuck you like you dry finger fucked my ass."

Jonas whimpered.

'What a fucking pussy,' I thought. 'If someone dominant told me that, I'd be gagging for it already.'

Taking pity on him, I lubed my cock before positioning it on his rosebud. I wanted to rip my hips forwards and tear his ass open, but I resisted and slowly slid past his outer ring and through his knot.

I came to rest with my pubis against his ass.

I applied lube to my hand and reached down to grab Jonas's cock. I gripped him firmly in my hand and began to stroke him as I waited for his ass to become accustomed to having a cock as big and as thick as mine in it.

After only a few minutes, Jonas was stiff as the proverbial board in my hand, and he was groaning and pushing his ass back at my cock.

Jonas eventually groaned, "Fuck me, Olivia, please. I need to cum on your magnificent girlie cock."

Stroking him faster, I began to gently fuck him.

Jonas wasn't reacting to my cock in his ass as well as I would have hoped. Remembering what Samuel had done to me, I lifted his left leg by the back of its knee. I kept raising it and stroking into him until I heard Jonas grunt in pleasure.

My cock had rubbed across his P-spot, his prostate.