Tranny Babysitter: Force Femme

Tranny Babysitter: Forced Gay and Feminisation.

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

Warning: There is a lot of use of words 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.

All characters are a minimum of 18 years old.

Chapter 05: The First Sunday.

Note: This story takes up from the end of 'Tranny Babysitter: She Owns my Ass.' The 'action' scenes, I hope, are hot enough for you, the reader, to not need to read the previous story. But to understand and appreciate the journey the main character, John has been forced on, you will need to read the first part.

Cheers, JohnMurray4173

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Hannah woke me around 6.00 am the following day.

"Josh is fucking your wife again. You'd better go shower and get changed into your boy clothes. Wait in the garage until you hear us all in the kitchen, then come inside.

Pretend you've just gotten back from your mother's and believe Josh and Courtney when they say Josh brought Courtney home because she was a little under the weather and then slept on the couch because Roger and I were in the spare room."

Rushing, I quickly complied. I sure as hell didn't want Josh to realise I'd spent the evening partying with him and then spent the night being fucked by a homo.

As I headed out the door after my shower and changing, I said, "Won't he ask where Olivia is?"

"I'll tell him she caught an Uber home early this morning," Hannah replied.

The curtains to the main window of my bedroom, sigh, Courtney and Hannah's bedroom, don't close properly. There's always a little gap either in the middle or at one end. I kept meaning to get someone in to remeasure and cut some new drapes but hadn't gotten around to it.

I badly wanted to see how big Josh was, so I crept around to that window. The gap was at the same end I was.

Slowly lifting my head, I peered through the gap into the room. Courtney was wearing her thigh-high fuck me boots and nothing else. Her toned body and 34C breasts were displayed as she rode Josh's cock facing me.

To my disappointment, Josh was only average in the tackle department. I wasn't worried about Courtney catching me peeking, and Josh couldn't see me past Courtney, so I stood up.

Courtney saw me. She gave me a smile and a wink, lifted her pussy off Josh's cock, and then lowered her ass onto it.

Fuck! Was everyone except me going to get to fuck her ass?

With her heels on the bed, and her knees bent, Courtney leant back onto Josh. His arms snaked around her body and began to maul her tits. Josh was squeezing and pinching my wife's tits quite mercilessly. He found her nipples and flicked them both with his finger and thumb.

Courtney moaned in appreciation. Her cunt gaping lewdly at me Courtney began to raise and lower her hips. I watched as all but the tip of Josh's dick came into view, then disappeared back into Courtney's dirt hole. It was fucking hot!

I took my cock out of my pants. This side of the house is well fenced so no neighbours could see. I began to jack myself off to the show.

Courtney came, I was grateful she didn't squirt as she had for Hannah, but she did cream deliciously on Josh's tool.

I heard Josh mutter that he was about to cum. Courtney slid off his cock and moved her pussy onto his face. Showing me his cock, Courtney lowered her head down and swallowed all of Josh's meagre 6-inches.

Lifting her mouth a little, Courtney wrapped her thumb and finger around Josh's shaft and milked him into her sucking and slurping mouth. Accepting his entire load, Courtney opened her mouth to show me she had held it all in there, then swirled it around her mouth with her tongue before swallowing it down.

Watching, I came onto the wall.

Courtney gave me another smile, and a wink, then swung off the bed and walked over to the window. I ducked down quickly.

"Enjoy the show, my little fag hubby?" she whispered loud enough for me to hear. "Maybe we can build a hidey-hole for you to sit in and watch as I fuck each and every one of your unmarried teammates."

Courtney pulled the curtains open as I slunk back to the garage. To my shame, I was considering where I could build a hidey-hole that wouldn't be immediately obvious what it was.

About 20 minutes later, there were unmistakable sounds of people laughing and chatting in the kitchen/dining room area, so I opened the car door before shutting it firmly and opening the door into the lounge.

With her boots still on, Courtney wore a short diaphanous gown that barely covered her naked ass. Her nipples were hard and plain to see. Josh was wearing one of my dressing gowns, the cheeky bastard. Banging my wife and wearing my damned clothes like he was king shit of the hill.

"Hey, babe," Courtney said. "You're home earlier than expected."

"I had to drop dad off at the airport," I lied. "So I thought I'd come home for a while to see you before going back to check on mum."

"You mum not well, John?" Josh asked. "That's a shame. She's still looking after the kids, though?"

"My sister's got them with hers," I further lied.

Hannah was in a tiny baby doll nightie, and her huge tits bulged out of the top. Where she had tucked her penis, I had no idea.

"Glad you're home," she said. "You can give Roger and me a lift to my place."

"What are you doing here, Josh?" I asked. "Why are you in my dressing gown?"

Courtney broke in, "I got a little tiddly on our girl's night out, baby. Josh saw me and decided to look after me and ensure I got home safely. Roger and Hannah were too busy fucking to look after me, so Josh made sure I didn't throw up and asphyxiate.

I spilt some wine on his pants. I gave him your robe so I could wash and dry them.

He slept on the couch."

"Thanks for taking such good care of my wife, brother," I said to Josh. "If there's anything I can do to return the favour, let me know."

The prick didn't even have the grace to blush.

"No worries," was all he said.

Courtney made some breakfast, and we all acted like everything was normal. It was surreal. Roger and Hannah acted like lovers, Josh and I like mates, and Courtney and I like we were a loving married, faithful to each other, couple.

After breakfast, I told Hannah, "I'll take you back to yours on my way back to mum's now if you want?"

Turning to Josh, I asked, "Do you want me to drop you home as I go?"

Courtney interjected again, "His trousers are still drying, so I'll have to drop him home later. If you take the Avant, I can take Josh home in the R8."

'Neatly done,' I thought, in grudging admiration. 'You've just bought yourself a whole day, nearly, to fuck Josh in as many ways and positions as you want.'

Hannah and Roger were holding a bag each. I was perplexed because Roger hadn't been carrying a bag last night.

We got in the Avant, "We going back to yours, Hannah?" I asked. She had been living with her mum.

"Of course not. I live with Courtney now."

Roger spoke, "No, we'll go to mine, I live alone, so it'll be more fun."

I suspected my ass was about to be filled with cock again. I'm not sure it had even remotely recovered from last night's shagging.

Following Roger's directions, we were soon outside his unit. When we entered, it was apparent this was the unit of a femmeboy crossdresser. There were outfits carelessly flung everywhere. All kinds of wigs, in many styles and a rainbow of colours, were hung on every available space.

Many styles of shoes, from white sneakers to 7-inch pumps, from low sandals to high-heeled strappy ones with platform soles, had been casually kicked off and left where they landed.

How he found anything again, I couldn't fathom.

My 'gaydar' is usually pretty well-tuned. How it had misfired so badly last night, I have no idea.

There was one fastidiously clean area, though. Roger had a double seat vanity along the back wall of the lounge/dining area. This area was clean, tidy and well organised. It was almost like two different people were living here. A man that was a grub and a woman who was neat and tidy.

Good to see you've cleaned up since the last time I was here, babe," Hannah told him facetiously.

Roger giggled effeminately, "I'm afraid Roger is a bit of a grot. Fortunately, I have Rashida to clean up for me, but she only does the vanity."

'That I can see,' I thought.

"Go wet a couple of tea towels, Rashida," Hannah told Roger. "Give it 100 seconds in the microwave. I'm going to straight shave you and Olivia. Then we're getting dressed and out of here."

I didn't want to be out as Olivia in the middle of the day, "I don't have anything to wear," I pointed out.

Roger handed me the bag he was carrying. I looked into it. Hannah had selected an outfit with shoes, underwear and something called a gaff. It was designed to hold the balls back up in their canals and your penis along your perineum.

There was no point in arguing, even without the electric shock cuff on my balls, so I sighed and took a seat at the vanity.

Roger explained as we waited for Hannah, "You have to do your day makeup a little differently from your night-time one. The light during the day is natural and much softer. If you do your makeup as thick as last night, you'll look like a drag queen dragging her sorry arse home after an all-night rave.

Day makeup must be lighter, softer, and more blended to look natural. Think of the girls in the office who always look like they're about to go clubbing. Does that look good?"

I shook my head.

"For daytime, it needs to be understated, so we'll go for a foundation a shade or two lighter than last night. This one, I think."

He handed me a bottle of Shiseido Synchro liquid foundation.

"With your skin and eye colour, brown is still good for the eyelids, but a little lighter than last night, and no white in the corner."

He handed me the items I would need.

"You'll also need a lighter blush with the lighter foundation."

He added what he thought I'd need to the growing pile in front of me.

"Lippy is last, same approximate colour as the blush."

It joined the pile.

The microwave went ding.

Hannah wrapped Roger's face with one towel, mine with the other. Roger was taking HRT pills sporadically, so his skin was already softer than mine, and his facial hair was more delicate. Hannah would shave him first, as his skin didn't need as much time to soften up.

As long as the towel remained hot, my skin and face would soften under the moisture and heat, making shaving a more effortless and closer experience.

"We're going to book you in for laser hair removal for your body and electrolysis for your face, bitch," Hannah growled at me. "Because I'm fucked if I'm doing this every time we go out.

That didn't bother me. A few of my teammates had opted for the hairless look, so I wouldn't stand out.

"Come and blow me whilst I shave this slut's face," Hannah demanded of me.

Eagerly, I got on my knees before one of my two Mistresses and guided her soft, thin tool into my mouth. I wanted to see how quickly I could make her cum, so I cupped her balls and slid my finger along her perineum to finger her rosebud.

I kept bringing that finger back to my mouth to work some moisture into Hannah's ring. Once I was satisfied her starfish was wet enough, I circled it in smaller and smaller circles before homing in on the centre.

Applying a little pressure, I managed to slip my finger through her ring. I kept adding moisture and worked my finger in slow rotations until all of my forefinger was buried in her ass.

Letting go of her balls, I changed to my middle finger. Thinking about where Hannah had found my prostate, I searched for hers. I hooked my finger up and back and, by the little jump and groan she gave, found it almost immediately.

"I just about cut his fucking throat," Hannah growled. "Oh fuck, right there, yes, there, OMFG! I'm cumming," she moaned as I stroked her P-spot repeatedly.

Hannah filled my mouth with her delicious excretions again.

Fuck! Was it only yesterday that I was disgusted, to the point of throwing up by cum? Now I loved the taste of her ladyboy sperm.

But, secretly, I think it was the power to make her cum that I enjoyed. Its why, amongst the footy sluts, I had the best reputation. I revel in making my partners cum. It is the best part of sex. Having your fuck buddy beg you to hurry up and cum because they can't take anymore is such a power trip.

In my mind, I was starting to rejoice that I could now make both sexes cum almost equally and as often.

Hannah finished shaving Roger, "You should reward Olivia for giving me such a fine blowjob by sucking her off as I shave her, don't you think?"

I was doubtful. I hadn't had a man suck me yet. Hannah had, but she's definitely not male, despite the long penis.

Roger was a skilled headjob exponent, though, and hey, a blowjob is a blowjob, right? I came into his mouth almost as quickly as Hannah had cum into mine.

Roger sat beside me, and we both applied our makeup.

He turned to me, "Almost," he said. He took the blending brush, smoothed the transition from blush line to foundation makeup and painted my eyelids a little wider. He also added about another millimetre to my lip line.

He turned me back to the mirror, the difference seemed minimal, but the effect was dramatic. My skin looked natural, the blush a bit of high colour on a warm day. My lips looked full and plump, with a perfect cupid's bow.

Roger sorted through his collection of wigs and found a long tousled black one. My natural hair is a dark brown, bordering on black, so the wig went well with my eyes and skin colour.

I slid the stay-up stockings onto my waxed legs. These had a pencil line up the back. Roger helped me to get it perfectly straight. I put the gaff on and then tried not to go hard as Hannah helped me tuck my balls and cock away.

When she finished, I could see no sign that I even had male genitalia.

I put on the bright blue bikini brief and the matching bra Hannah had chosen. I had already painted in my 'cleavage shadow', so I slipped the breast forms into place.

"Bend over at the waist and give your shoulders a shake," Hannah said. "It'll settle the forms into a more natural position. That's what the bra is designed to do."

I did as instructed, and my 'breasts' looked awesome in the mirror. Even from this close, it was hard to detect they were merely forms, not natural boobs.

I put on the ultra-small red miniskirt and then pulled on the black V-necked stretch cotton top that she had chosen to go with it.

Hannah had added a pair of low-heeled strappy black sandals to the bag. She showed me how to tie the straps around the top of my calves so they wouldn't fall.

Hannah handed me a short jacket top to put on if it got cold. It was late spring in Brisbane, so I doubted it would.

The last item I was given was a small red shoulder bag.

"Lippy, blush and foundation, your mobile phone, and credit cards are all you ever take out with you. Those women that carry everything but the kitchen sink in their oversized handbags are only waiting to be robbed before they learn better," Hannah told me.

Putting the bag over my shoulder, I pulled some gowns off Roger's full-length, freestanding mirror and examined myself. From the neck down, I was a definite 10. With legs and arms as long and well-toned as mine, and a firm, taut ass shown off in an ultra-mini, plus huge double D firm tits, I was an easy 10. Higher if the scale allowed.

"Butter face," I muttered.

"What was that?" Hannah asked.

I turned to her, embarrassed, "Butter face. Great body, but her face, ahh well."

Hannah turned me back to the mirror, "You knew the boy that came before Olivia. He was all you knew, so that is what you see when you look at yourself in the mirror. Roger here hadn't seen the boy until this morning. Roger, when you met us at Daniel's, what did you think?"

"I couldn't believe she was a he," Roger answered.

I could see the sincerity in his face.

"You'd roped me into your scheme to turn him gay, but I honestly thought you were trying to turn me straight with a genuine girl that you were pretending was a man.

It was only when you started the charade of not talking because of the operation that I began to think she might have been a he, but it wasn't until he peeled the tape off and took his cock out that I was sure."

Roger turned to me, "Look, honey, you're not going to win any beauty contests, that's true, but you're at least a 6.5. In the right light, you're a 7. If they're legs and ass men, maybe even a 7.5. 'Butter face' is way too harsh. I'd call you pretty. Not beautiful, but pretty."

I was nearly in tears. Fuck me! Why would I be filling up with tearful pride because some faggot thought I was pretty? I liked the compliments, though. I liked them a lot!

Roger, or Rashida, as I should call her now, looked fucking awesome. She had done her makeup just a hair off Gothic. Pale foundation, dark red blush, blood-red lippy and inch-long false eyelashes.

She had paired this with a short black spikey wig. If you've seen the movie 'Beetlejuice', she looked a lot like a taller version of how Winona Ryder looked in that film.

Roger/Rashida wasn't as tall as me, but he was taller than the 6-foot (183 cm) Hannah. He was a little, not fat... I guess the fitting description is 'soft'. Like he could have done with a few months in the gym to tone up.

If he did go to the gym, he would have put weight on but lost a couple of clothing sizes.

I had no idea if men are handsome, other than the obvious ones like Brad Pitt, Johnny Depp, Chris Hemsworth, etc., but I would have thought that, as Roger, he would do well with the ladies if that was what he was into.

Rashida put on a full-length black dress that buttoned down the front. He had unbuttoned the top until his 'breasts' gaped out. And had undone the bottom ones to just short of his crotch.

Rashida's cock was so long that she didn't need to gaff or tape her appendages, she could push her balls up into their canals, then push her shaft so far back along her perineum that her thighs held it there, and the shaft held her balls in place.

Rashida put on some Doc Martens boots.

"We're ready, darlinks. Shall we go?" She lisped outrageously. "We have the beautiful," she indicated me, "the sublime," pointing at Hannah, "and," with a flourish indicating herself, added, "the ridiculous."

"I think you look as hot as," I muttered before thinking. "Even before all this shit happening to me, I probably would have hit on you."

Then, in a voice indistinguishable from a 1,000 other woman's, Rashida blushed and said, "And I, honey, would probably let you buy me a drink. I may even have let you feel me up."

She gave me a wicked grin, "Even before you had 'all this shit happening to you'."

"You're going to have to teach me how to talk like that," I told her.

"I have no idea, but I'll give you the number of my vocal coach. She can try and train you if you'd like?"

"Yes, please."

We exchanged numbers so she could text it through.

"Hurry up, or we'll miss our appointment," Hannah exclaimed. "Rashida, call us an Uber. Olivia's driving Courtney's car. The licence plate "Courts One" is a dead giveaway. Let's not advertise ourselves too much just yet."

Confused, I asked, "Where are we going?"