Tranny Babysitter: She Owns My Ass! - Cover

Tranny Babysitter: She Owns My Ass!

Copyright© 2022 by JohnMurray4173

Chapter 2: The First Friday

BDSM Sex Story: Chapter 2: The First Friday - 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  

I usually use the main bathroom if we go out together because Courtney takes forever.

I came out of the bathroom that Friday night, completely starker, to find Hannah standing at our bedroom door talking to Courtney.

‘Oops,’ I thought.

I didn’t care. I’m 6 ft. 4 in. (193 cm) of lean muscle. I’m all long legs and long arms and less than 3% body fat. You can draw virtually all the various muscles on my arms, legs and torso. They’re that well-defined. Showing some skin doesn’t bother me at all.

Besides, Hannah might want a taste of it if she saw what I carry between my thighs.

Hannah, with a little smile playing about her lips, stared openly at my todger. She had gone quiet, though, so Courtney stepped into the hall to see why.

“Oh, FFS! John,” she said to me. “Stop showing off. The poor girl doesn’t need to see that!”

She threw me some boxers.

Twirling them around my forefinger, I strutted into the bedroom. Courtney rolled her eyes and shut the door behind me.

I began to dress before realising Hannah was on this side of the door, not outside, as I had assumed. Stunned, I faltered and almost fell over trying to get my trousers on.

Now call me dense, but I still didn’t figure out something was happening here.

Courtney and Hannah had a great chuckle at my expense.

“Need some help getting dressed, baby?” Courtney chortled.

“All I need to perform my best is an audience,” I returned. “The laughs are sure to follow.”

The girls went back to sorting out Courtney’s outfit for the night. They finished on a bright blue midi-dress that was tight at the boobs, flared out at the belly, and then cinched on the hips. The dress accentuated my wife’s magnificent breasts. At $12,000, they’d better be damned magnificent! Flaring to cover her pregnant belly, it tightened back into the hips, emphasising her toned ass and thighs. The dress was paired with 7-inch stiletto-heeled thigh-high black boots.

I knotted my tie and watched as Hannah slightly changed how Courtney applied her makeup. I didn’t understand the difference, but the effect was incredible. My wife’s eyes seemed wider and brighter than usual, and her lips fuller. Courtney’s already well-defined cheekbones looked quite angular in the light. She looked every inch the Queen of the WAGs that she was.

“There you go, my girl,” Hannah said in quite a proprietary way.

I thought it was a little weird, but shrugs ... I’m male, right? We don’t see even the obvious when we don’t want to.

I was a hit at the function. The audience laughed at all the right places and none of the wrong ones. I got a standing ovation at the end. The next hour was spent schmoozing with the sponsors. Shaking hands, letting them take photos, giving their wives the obligatory ass squeeze and peck on the cheek, and signing autographs.

One of the big reasons the club sends me to these events is because I like doing them. They’re fun, plus it’s an excellent place to meet sluts.

I probably spent too long with the daughters of a couple of the major sponsors because Courtney got a little pissy. When she gets pissy at me, she drinks too much. She doesn’t get loud or obnoxious. She just wants to sleep.

I took her home. It’s getting too close to preseason training, so I’m mostly off the grog. Audi is one of our club’s sponsors, so I’ve got an Avant as a family car and an R8 for me. We’d taken the R8.

Hannah was waiting on the lounge with her bag at her side when I carried Courtney inside.

“What did you do to piss her off?” She asked.

“Who says I did anything?” I replied.

“She only ever drinks too much when you’ve been an asshole,”

“What? Are you her mother?”

“Let me help you put her to bed,” Hannah said.

I carried Courtney to our bedroom. Hannah pulled the sheets back so I could lay Courtney on the bed.

Hannah began to strip Courtney off. I was like, WTF?

“What are you doing?” I asked.

“What does it look like? You can’t leave her to sleep in her dress, it’ll ruin it, and she certainly can’t sleep in those boots. Plus, it’s not healthy to sleep with a bra on,” Hannah replied.

I watched as Hannah completed taking Courtney’s gear off. Did her hands linger a little long on my wife’s breasts? I wasn’t sure what I’d seen, but my dick gave a jump at the thought of Hannah and Courtney playing together.

I’d had plenty of FFM threesomes, but never with my wife.

Hannah kissed Courtney on the cheek, stroked her hair, and then looked at me.

“So, what did you do?” Hannah asked.

“Nothing I haven’t done 1,000 times before,” I replied.

“Who did you hit on? Someone’s wife or someone’s daughter?”

“I may have done some harmless flirting with some of the sponsor’s wives or daughters,” I answered. “It’s expected and all part of the schmooze game.”

“How many phone numbers did you get?” Hannah questioned.

I blushed, “I don’t know what you’re talking about.”

“How many wives told you when they would be home alone?”

“What? None.” I managed to stammer.

I had gotten four numbers and two hints to come and visit when hubby was going to be out. But I rarely took those hints. The woman has to be an almost 10 for me to consider it.

“So Courtney just decided to write herself off because you were being a perfect gentleman then?”

“It’s not my fault she’s a two-pot screamer,” I answered defensively.

“So, are you going to kiss me or not?” Hannah asked.

“Wha _ What?” I said, shocked.

“Are you going to kiss me or not?” She repeated.

“Here in the bedroom with my wife two feet away?”

“Sure, why not?” Hannah stated. “Unless you’re chicken?”

That’s a dare I can’t refuse, so I reached out my right hand. When Hannah took it, I pulled her slowly towards me making her climb onto the bed and step over Courtney.

Courtney muttered something as she felt Hannah step over her, then rolled onto her side facing me. Her eyes were still closed, and she was snoring softly, so she hadn’t awakened.

Hannah was standing on the edge of the bed, and her groin was right at my mouth’s level. I grabbed her tight buns and brought her crotch to my mouth. Just when I thought my lips were going to press against her jean short’s zipper, Hannah stepped off the bed. Her huge tits rubbed across my face as she slid onto the floor.

“Kiss me first, John,” Hannah said.

I kissed her with every ounce of skill and passion that I had. I turned my head to the side and then ran my tongue softly across the corner of her mouth as I found her left breast with my right hand.

Hannah shivered, then softly moaned as my fingers stroked her nipple through her T-shirt, and my tongue probed her mouth’s erogenous zone.

Moving my lips to cover hers, I snaked my tongue out and brushed it across her lips. Hannah opened her mouth and let my tongue find hers. We tongue danced for a long time. I could hear and feel, Hannah’s arousal growing exponentially as she moaned into my mouth as I kissed her.

I reached for the button and zip of her shorts, but Hannah swayed her hips back away from me.

“My breasts next, John,” she told me.

I pulled the bottom of her T-shirt out from her shorts and lifted it over her head. Hannah’s massive melons came into view. They were so firm that she was braless. Her breasts were beautiful and perfectly symmetrical, a dead giveaway that they were fake because there’s always a slight variation between natural breasts.

I didn’t care. I know from making love to my wife that augmented breasts and their nipples are still as sensitive as natural breasts are.

I put my hands on Hannah’s waist, lifted her then lay her on the bed. A surprised grunt flew from her lips at how easily I picked her up. I can deadlift twice my weight, around 375 lbs (170 kg). Hannah wouldn’t have weighed 154 lbs (70 kg), so lifting her was easy.

I tried to slide between Hannah’s thighs, but she kept them tightly closed, so, a little awkwardly, I had to lie across her hips and stomach to be able to lash her nipples with my tongue.

Hannah moaned lavishly as she guided my head from breast to breast with her hands. Her eyes were closed, and her breaths were coming in quick pants. It was self-evident how turned on she was, but she still wouldn’t let me between her legs or touch her pussy.

Hannah pulled me insistently upward, and I moved at her urging. She quickly had my pants down and my wood in her mouth.

‘Now, this is good,” I thought.

I undid my jacket and threw it aside, then undid the buttons on my shirt before throwing that aside too. I kicked myself out of my shoes and out of the legs of my trousers. Naked, I held Hannah’s head as she bobbed up and down on my cock. I’m sure I’d had better blowjobs, but I can’t remember when.

She was bobbing up and down much faster than usual and sucking more insistently than a woman typically does. It felt fucking awesome!

Hannah cupped my balls, reached between my thighs and fingered my ass. Coming from a small town, I can be a little homophobic. I try not to be, but those small-town prejudices run deep, you know? The whole ass play stuff has always seemed a little gay to me, so I don’t usually let anyone touch my brown star at all.

Hannah’s blowjob felt so awesome that I just went along with it. Hannah wet her finger with her mouth and began to rim me. It felt pretty damned good, so I spread my legs to allow her better access.

Hannah worked a finger into my ass. By now, I was so turned on I would typically have cum in the woman’s mouth, but Hannah had circled my balls with her thumb and forefinger, holding them away from the shaft. I still could have cum, but it would probably have hurt, so I hadn’t yet.

I felt a second digit at my rosebud. Working moisture into my butt, Hannah eventually forced a second finger into me. I was about to demand she pulled them out because I wasn’t no arse bandit faggot when she found my prostate, and I was fucking gone!

“Oh, fuck!” I groaned.

I was about to shoot my load into Hannah’s wet and warm mouth when she squeezed my balls hard and hauled them downward.

Letting my cock slip out of her mouth, she said, “Not yet, Mister! I need you to beg me to cum first.”

‘What the fuck is this?’ I thought. ‘Is this ‘opposite day’? I’m the one that demands the woman cums. They don’t make demands of me!’

Hannah resumed sucking me and fingering my prostate, my P-spot if you will.

Desperate, I found myself pleading, “I need to cum, Hannah, please let me cum.”

She responded, “Do you want to fuck me, John?”

‘Does a bear shit in the woods?’ I thought.

“Yes,” was what I answered, though.

“Then you must let me blindfold you and tie your hands to the bed. I will then ride you. Okay?”

I like a bit of kink play. It’s one of the few things Courtney will let me do. That book ‘50 shades of... ‘ was fucking awesome. Courtney read it and then wanted me to do all of the things that were in the book to her.

“Sure,” I said, holding my hands out to be tied.

Hannah opened our walk-in robe and took a bag out. Out of the bag, she brought a pair of steel cufflinks and a blindfold. It was a fairly big bag, so I wondered what else she might have in there. I wondered briefly why one of her bags was in our walk-in robe, but those thoughts quickly disappeared as Hannah stroked my rampant dick.

I was soon tied to the bed. The blindfold Hannah had put on me bulged in the middle, so my eyelids were forced firmly shut. No matter how much I twisted my head, I couldn’t see a damned thing.

Before I could work out what was happening, my ankles were tied to a leg spreader. I mean, WTF! Right?

Hannah lifted my legs by the spreader. Holding my legs high, Hannah spread her thighs and slid up until her pelvis pressed against my ass.

‘This is a weird position for her to ride my cock,’ I thought.

Something was being pressed against my ass ring. Thinking Hannah would finger my prostate again, I relaxed my ring and let whatever pressed against it slide inside.

It hurt a lot, as whatever it was, was much bigger than Hannah’s two fingers. But after it got far enough in, it scraped across my P-spot, and it felt fucking divine!

I moaned in appreciation, “Fuck, that’s good, do me some more.”

“As you wish,” Hannah answered.

Whatever was in my ass was pulled back and then shoved in again.

I couldn’t help it. I groaned like a bitch, “Oh fuck, yes! Fuck me like the slut I am.”

Hannah began to stroke whatever was in my ass in and out of me faster.

I got very vocal, “Fuck me, oh, fuck me good. Fuck my ass, fuck me and make me your bitch,” I heard myself almost screaming.

The item rubbing over my prostate had driven me nuts. At that point, if someone had put a cock to my lips, I would probably have sucked it I was that horny. I had to cum. I just had to cum.

“Please may I cum, Miss Hannah?” I begged.

“Yes, you may cum,” Hannah answered.

With an expansive groan, I squirted my load onto my stomach. Hannah ripped the blindfold off as my dick spasmed for the second time, shooting cum two feet in the air.

I looked at Hannah’s sweat-covered breasts as she held my legs up and stroked the item into me. My eyes dropped down to see what was in my ass. It was Hannah. Her long thin cock was pounding into my ass as she thrust her hips forwards and back. Every stroke scraped the head of her long thin 8-inch penis over my prostate.

Unable to help myself, I squirted again and again. Her dick in my ass felt so fucking awesome that my homophobia was quelled.

“Told you he was a submissive cock sucker at heart,” Hannah said to Courtney. “Male sluts like him always are. I bet if I offered my cock to his lips, he would suck it without hesitation.”

I looked to my left. Courtney’s eyes were wide open, staring at me. It turns out the bitch had only pretended to get skunked. She hadn’t had a drop all night. This was all part of her and Hannah’s plan.

So there I was, handcuffed to the bed, my feet in a spreader bar, with a tranny’s dick buried balls deep in my ass, having just cum to a tranny cock fucking my rear passage, staring at my wife as she stared back at me.

‘Fuck.’ I thought. ‘How do you explain this?’

“Hammer that fucker’s ass,” my loving wife of five years said.

And Hannah began to fuck me again.

I guess that was how you answered that. You realised that your wife had set you up to be fucked by a tranny.

My brain was screaming at me that this was wrong. Men were supposed to do the fucking, not get fucked. My sexual urges didn’t care. Having cock in my ass felt so good and natural that I came again as Hannah fucked me.

Hannah pulled out of my arse and said to Courtney, “Suck me clean, slut. I want to be in your cunt next.”

Courtney was on her knees sucking Hannah’s wang in a flash. I had to suppress a sudden surge of jealousy. I wanted to suck that cock. I wanted to be Hannah’s submissive slut. My wife was in the way.

“Once I’m balls deep in your wife, you can fuck my ass, John,” Hannah said.

Now that sounded right up my alley.

Courtney uncuffed me and then released my ankles from the spreader bar. She rolled over onto her back, opened her legs, and then used her fingers to spread her pussy lips apart.

“Get your head over here, John,” my wife demanded of me. “I want you to watch as Hannah’s cock enters where you’ll never get to go again.”

“Wha _ what?” I asked, confused.

“We’re making you our chastity bitch, John. Look up there,” she pointed to our dresser. There was a digital camera recording every moment.

“If you try and fight this, we’re releasing this movie to PornHub and sending stills to every major news outlet,” Courtney explained. “You think you’re such a stud, but now you’re my cuckolded, cock sucking bitch.

Oh, you’ll still get to fuck Hannah’s ass as she likes being done anally, and I don’t have a penis, but there’ll be no more pussy for you. From now on, it’s all tranny cock and ass.

And you’ll get to watch as I fuck Hannah and as many of your teammates as I can seduce.”

“You can’t do this to me, babe,” I pleaded. “You’ll wreck my career, and I won’t be able to find a team to play for. Nobody will want a pooftah playing for them.”

“You’ve made plenty of money over the last six years, John. I’ve carefully invested most of it. At the moment, we have over 5 million in investments. Money won’t be a problem, even if you do get fired.

I don’t think you will, though. You won’t listen, but you’re seen as a talented player who is greedy and selfish—one that looks for individual glory and not for team success. Hannah and I will teach you how to submit to a more dominant force. How to be a team player.”

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