Tranny Babysitter: She Owns My Ass! - Cover

Tranny Babysitter: She Owns My Ass!

Copyright© 2022 by JohnMurray4173

Chapter 3: The First Saturday Morning

BDSM Sex Story: Chapter 3: The First Saturday Morning - A hyper-masculine alpha male is subjugated and sissified by his babysitter and wife.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Ma/Ma   Blackmail   Coercion   Consensual   NonConsensual   Reluctant   Lesbian   BiSexual   Heterosexual   CrossDressing   Shemale   TransGender   Fiction   Cheating   Cuckold   Slut Wife   Wife Watching   Wimp Husband   BDSM   DomSub   FemaleDom   Humiliation   Light Bond   Rough   Spanking   Anal Sex   Cream Pie   First   Facial   Pegging   Sex Toys   Babysitter  

The following day I woke up to a cock being forced into my ass.

“I’ve got morning wood,” Hannah moaned. “Courtney’s ass and cunt are worn out, and you need to relieve me.”

I thought to resist, but the head of her magnificent cock scraped across my prostate, and I couldn’t suppress the moan of desire that escaped from my lips.

“Cum in my slut hole,” I found myself pleading. “I need to feel you shoot your delicious lady juice into my ass so I can cum, too.”

“Such an obedient whore,” Hannah said. “You’re going to swallow my load, though. I’m not wasting it in your ass. If you cum before I say you can, your balls will never recover, John. Do you hear me?”

“Yes, Mistress Hannah,” I groaned as her cock slid deliciously over my P-spot.

Desperately, I thought about anything else I could to distract me from cumming. I even imagined the coach’s wife, a fucking giant, 300 lb (136 kg) woman with a better moustache than I can grow, naked, to stop orgasming too soon.

Hannah grunted in what seemed like 10 hours’ time and pulled out of my ass.

“Get ready to receive, bitch,” she said.

I was quickly on my hands and knees, ready to accept Hannah’s load.

Hannah jammed all 8 inches down my throat. My subconscious remembered my training from the previous night and I was able to relax my throat and swallow swiftly so I could stand Hannah’s long tool sliding over my gag reflex and down my throat.

With a satisfied groan, Hannah came into my mouth. To my shock, I nearly came to the exquisite feeling of swallowing her female dick’s juice.

“Do you want to cum, my cum swallowing whore?” Hannah asked.

In tears, knowing what was next, I begged, “Yes, please, Mistress.”

“Assume the position then, my wannabe cock sucker.”

Even though I did not want to be a cock sucker, I was swiftly on my back. Without being asked, I lifted my hips off the bed and wrapped myself around myself so my ass was up in the air, and my knees were almost on the bed.

The eye of my cock greeted me again.

Hannah bent me even further over than before. My cock was inches from my face.

Forcing me down even more, Hannah demanded, “Open your mouth, lift your head and suck your cock.”

I’d never imagined being 7.5 inches long was a liability. I needed to lift my head off the mattress only a small distance before I could suck the head of my cock into my mouth.

“Cum just as quickly as you can, my cum receptacle,” Hannah told me.

I sure as fuck didn’t want to suck myself off, but Hannah slid a long-nailed index finger into my ass and massaged my prostate.

I blew immediately.

“Not a drop shall you spill, slut,” Hannah dictated.

Bawling like a baby, I swallowed all of my excretions.

“Good girl,” Hannah said.

‘Girl?’ I thought. ‘I’m about as manly as they get.’

Hannah had other ideas, though.

“You football players all so nearly queer, anyway,” she said. “All waxed off from neck to balls and man buns galore. Courtney says you take longer in the bathroom to get ready than she does and use more product on your face and body than any woman she knows.

Have a look in the wardrobe robe. I got you some new outfits. Well, Courtney paid for them, but I chose them.”

Fearfully, I opened the wardrobe door. The robe was full of women’s clothing. Mostly skirts and tops as very few labels make anything suitable in a dress for someone as tall as I am.

“Who are these for?” I asked, already knowing but dreading the answer.

“You, of course,” was the obvious reply. “I’d suggest you choose an ankle-length skirt for your visit to the waxers. Hairy legs look so stupid sticking out the bottom of a short skirt.”

“I’m not wearing a dress!” I emphasised.

“No, you’re not. You’re going to wear a top and a long skirt. And you will wear it, or...”

She held the remote to the electric collar up.

“Dresser drawers,” Hannah pointed demandingly.

In trepidation, I opened the drawers Hannah had indicated. The top left had a selection of women’s knickers. Mainly control briefs, but also, some other ‘more sexy’ items, including thongs and bikini briefs. The other drawer held bras of various colours and designs.

Hannah reached into the drawers and removed a matching electric pink control brief and bra.

“I’m not putting those on.” I tried to explain.

Hannah sighed. I thought she was going to zap me into submission. Instead, she said, “Okay. I guess I’ll head back to my house and edit the recording from last night. Oh, and this one of you sucking yourself off,” she pointed at the camera I hadn’t noticed sitting on the bedside table. “PornHub viewers are going to love that one, I think.

Do you want to drop me off? I’ll let you kiss me as much as you like when we get there, or you could let me drive and give me a blow job along the way?”

Shoulders slumping, I put on the items Hannah had chosen.

“Second drawer down,” Hannah said peremptorily once I’d figured out how to get the bra on.

I opened the drawer. There was a heavy black box in there. I took the lid off and saw a pair of tit falsies looking back at me, or so it seemed.

Taking the forms out, I slid them into the bra cups. The breast forms were massive, at least a set of 18 Double Ds.

“Choose a skirt, slut,” Hannah demanded.

Every skirt was form-fitting. Whichever one I chose would emphasise my ass and legs. I’m an ass and leg guy. Ass, legs, and then boobs, in that order. A lot of my teammates are the same. I knew that if I wore any of these skirts, the ass and leg guys would check me out.

To my shocked disbelief, my dick jumped at the thought of being checked out by males in an admiring way.

I put on a long stretch cotton black skirt.

“Come to the kitchen, John.”

I meekly followed Hannah down the hall.

Hannah wet a tea towel under the tap and then put it in the microwave for 90 seconds. It came out steaming hot.

Showing me a straight razor and a can of shaving foam, Hannah said, “I’m going to wrap the towel around your face, jaw and neck to soften the skin up and then give you a straight shave. You’ll need to hold completely still. I don’t want to cut your pretty face.”

“What’s wrong with my usual 5-blade razor?” I asked.

“A straight razor shave is as close as you can shave. I can do your makeup with Dermablend to hide your beard line, but a straight shave first will make that job much easier.”

“I don’t want to wear makeup,” I protested.

Hannah patted my cheek, “I don’t care what you want, my little cum whore,” she told me. “This is about what Courtney and I want. And we’re going to make you our faggoty, cock sucking, and crossdressing bitch.”

Utterly deflated, I sat and let Hannah shave me.

Once she was satisfied my face was as smooth as it could be, Hannah made me follow her to our bedroom and sit at Courtney’s vanity.

Courtney stretched luxuriously as I took my seat, “Good morning, my fag husband. Did you get your cum breakfast?”

“He swallowed both mine and his loads. What kind of a man swallows a ladyboy’s cum, and then sucks himself off?” Hannah answered for me.

If the ground had opened up before me, I would gladly have jumped to my death.

“You made him suck himself off?” Courtney chortled. “Why didn’t you come and get me? I would have loved to see that!”

“I’m sure she’s up for another load, babe,” Hannah told her. “Look at the wet spot on the front of her briefs. The slut’s leaking precum already.

Hang on. I’ll get him hard. Then we can double him over and let him blow himself.”

The constant changing of pronouns was confusing me. My head was being done in.

I hoped Hannah would blow me, but knowing she would feed me her ladyboy dick again, I waited for what was next.

Sure enough, Hannah pulled her long thin todger out of her knickers and wiped the head across my lips.

This act was humiliating enough. Worse, I eagerly opened my mouth and let her cock inside.

The fact that my brain rejoiced in feeling Hanna’s shemale dick hardening in my mouth only confirmed the two were right. I was a cock sucking fag.

Feeling my wiener hardening even faster than Hannah’s completed my subjugation. I wanted Hannah to cum in my mouth again. I wanted to taste her cock juice in the back of my throat and feel her slimy essence sliding down my throat.

If that doesn’t make me a poof, I don’t know what does.

Hannah held my ears and pounded down my throat. She didn’t last long.

“Fuck!” She groaned. “I think he might already be a better cock sucker than you, my little cunt meat. You better lift your game, or maybe, I’ll take him as my lover, and we’ll make you our bitch.”

I swallowed Hannah’s load joyfully. What the fuck was wrong with me? I felt a surge of pride at being called a better cock sucker than my wife.

Pulling her softening tool out of my mouth, Hannah ripped the skirt and briefs she had made me put on down and off.

“On your back, slut,” she ordered.

Once again, my ankles were hauled back over my head, and my knees were forced onto the bed beside my ears. The head of my cock was only bare inches short of my mouth.

“Suck, bitch,” Hannah said.

Tears of resignation pouring from my eyes, I tipped my head forward and took the head of my cock in my mouth.

“Fuck me!” Courtney exclaimed. “He can suck himself off. Well, I’ll be damned.”

“He doesn’t like to make himself cum, though. Stick your tongue in his ass, and he won’t be able to stop,” Hannah instructed.

Courtney’s moist warm tongue slid across my chocolate starfish. With a totally useless groan of denial, I came into my mouth again. I was getting used to the taste. It was almost like swallowing heated raw oysters.

“Time for your makeup lesson, bitch,” Hannah told me. “If you think I’m going to do it for you every time, better think again.

Hannah started with the Dermablend foundation. This foundation is really thick and covers men’s skin exceptionally well. It smooths out all of your little nicks and scars. It’s very good with acne scars, not that I had many of those.

Once she had smoothed out my features, Hannah expertly blended blush along my cheekbones, jawline, and nose, softening my features and feminising my appearance.

Hannah used her blush brush to shade a curved line between my pecs, creating the illusion that my falsies were real.

Hannah did my eyes. Skilfully, she outlined my eyes and shaded my lids in, making my eyes appear brighter and wider than they were.

Finishing by drawing a lip line 5 mm wider than my actual lips, she shaded them in with a dark red lipstick. To complete the look, she handed me a long straight, honey blonde wig. She had to show me how to put it on and adjust the clips so the wig would stay in place.

Courtney was watching gobsmacked.

“He actually looks quite pretty,” she mused. “If I were a lesbian, I’d probably go for him.”

I looked at myself in the mirror and I could barely recognise myself. I wasn’t going to be winning any beauty contests, but I was at least a solid 6. With my long-toned body and lean features, I could easily have been a ‘butter face’ footy player’s slut. ‘Hot body, but her face, ahh well’.

Hannah handed me a V-necked stretch cotton top to wear over my skirt. The V emphasised that it looked like I was a massively titted woman.

“With your ass and looking like you have a canyon of cleavage, there’s not a straight man on the planet who is looking at your face,” Hannah told me. “I’m driving, and you can blow me on the way to the waxing salon.”

Courtney handed me a pair of low-heeled strappy sandals. I never thought they would make women’s shoes in sizes big enough to fit my feet boats, but they do.

I knew how badly fucked I was when I, without hesitation or being asked, handed Hannah the keys to my tinted windowed R8 and then got on my knees on the seat so that I could lean over the centre console, fish Hannah’s delicious, delicate ladyboy cock out of her jean shorts then happily suck it all the way to the waxing salon.

I was even disappointed when we got there without her cumming.

The woman who owned the salon was Isla, an old friend of Hannah’s.

“This your latest fagboy toy, babe?” She asked.

I wanted to deny it, but the salon’s waiting room had full-length mirrors, and I caught sight of myself. Fuck, maybe I wasn’t a fag, but I sure as hell wasn’t masculine.

“What are we doing, honey?” Isla asked.

“Full service, please, babe,” Hannah answered. “Back, sack, and crack, then full frontal. We’ll finish with a full leg wax.”

She jerked her thumb in my direction, “He’s paying. Charge him plenty, cos he’s got plenty.”

“Come with me, fagboy,” Isla instructed.

Helpless to resist, I meekly followed Isla down a short hall and into one of the waxing rooms.

“Strip naked, then get on your stomach on the table, honey. You don’t want to piss Hannah off as I see that she has got her favourite poof-making device with her. A zap to your balls will only make waxing an even more painful experience.

Don’t worry, though. Once she’s finished with you, you won’t even remember you used to like pussy.”

I did as was told.

I don’t have much hair on my upper back or shoulders, so that was a quick and relatively painless experience. I’m very hairy from the mid-back down, though, and my chest, stomach, and legs are a veritable forest.

Having my mid and lower back waxed was mostly pain-free. Having the hair ripped off my butt cheeks, ass crack, and perineum was fucking painful. Having my balls and the rest of my pubic area done was agonising.

Like many males these days, I already have my chest and stomach done regularly, so that didn’t hurt much.

The armpits and the insides of my upper arms stung like a bitch, as did having the hair ripped from my inner thighs. The rest of my legs and my lower arms were merely uncomfortable, not painful.

Isla began to rub some soothing gel and moisturiser into my legs. Working upwards quickly, her hands soon rubbed the lotion on and around my balls and shaft.

I like a wet hand job. It’s one of the things I love Courtney doing to me when she has her monthly break. I was hard in seconds.

“Very nice,” Isla hummed as my thick 7.5-inch dick rose to full form.

“I’ll french it for you,” she crooned. “But you have to return the favour.”

Wha _ what?” I asked, unsure what she meant.

Isla straightened up, lifted her skirt above her hips, moved her thong aside and brought out her hardening 6-inch penis.

‘Fuck me,’ I thought. ‘Is every pretty girl I meet from now on going to be a fucking tranny?’

I didn’t hesitate, though. Before Isla even took me back in her hand, I gobbled her ladyboy cock down.

“Start without me, did you, sluts?” Hannah grumbled as she stepped into the room.

Hannah said to Isla, “Pull your stool over so you can feed your boy clitoris into his mouth as he’s lying down, you short ass.”

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