Tranny Babysitter: She Owns my Ass

"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."

A little smile quirked Courtney's mouth.

"We'll teach you how to take one for the team. Well, I'm going to take one from the whole team. You get to watch.

Now get your ass over here. Mumma needs some girl dick in her fanny."

What choice did I have? I reluctantly knelt beside my wife's pussy and watched as Hannah slowly slid all 8 inches of her gorgeous ladyboy dick into my wife.

"The best thing about Hannah's cock is how long and thin it is. It feels so good in your ass, doesn't it, baby?" Courtney moaned.

Courtney wouldn't let me near her ass. She always said I was too big and it would only hurt.

"You want to show your pussy husband how much you like shemale cock in your ass, slut?" Hannah asked Courtney.

"Yes, please, Mistress Hannah," Courtney groaned.

Hannah slid her dick out of my wife.

"Get your tongue in there," Hannah required of me. "Get her ass ready for my ladyboy cock."

Courtney rolled onto her stomach and spread her ass cheeks.

"You want me to tongue her ass?" I asked, horrified.

I love having my ass rimmed by a wet and willing tongue, but ass play was 'too gay' for me. I never returned the favour.

"Get used to it, slut," Hannah told me. "You're going to be preparing many an ass to take my girly cock."

Reluctantly, I began to tongue Courtney's ring.

"Shove that tongue right in there, my hubby cock sucker," Courtney encouraged. "Get my ring all wet and ready for my Mistress' lovely ladyboy penis. Remember how many times you tried to stick your dick in my ass? Tonight my cuckolded man, you're going to watch as Hannah fucks a hole you've never been in and never will be in."

I was being slapped from shock to horror to stunned disbelief. This moaning slut was my wife? My prim and proper little woman who was so under my spell that I could fuck whomever I wanted, and she didn't say anything because I was her man. This was her?

What the fuck had happened?

As I knelt, tentatively licking Courtney's starfish, Hannah had taken something else out of the bag. Before I realised what she was doing, Hannah tied a strap around my balls and then attached a leather cord to it.

I wasn't licking enthusiastically enough for her liking, so Hannah hauled on the cord and whacked my ass with a broad leather flogger.

"Fuck!" I swore.

I'd had enough. I tried to round on her. I'm 85 kg of muscle. If I can't handle a couple of girls, I deserved to be their bitch.

As I turned, Hannah pressed a button on what looked like a TV remote. My balls exploded into pain. The strap had a built-in electric shock. I collapsed on the bed, writhing in pain.

Hannah smacked my ass again, "No, you don't, my pretty," She told me. "You need to learn your new role. You're our toy now, our pet. Your role will be to procure men, and sometimes women, to fuck Courtney and me, to prepare their asses for my cock, and to swallow cum loads from everyone we decide needs to be blown."

I'd played through pain before. Broken fingers, dislocated shoulders, and even a dislocated ankle hadn't prevented me from playing the game I love. I was able to force myself to my feet. I advanced on Hannah again.

Hannah pushed another button and then pressed the button for the shock again. I howled in pain as I collapsed to the floor, retching. There were levels to the amount of shock, evidently. I was to find out that the first shock was only on level 1. The second was on level 3. There were seven more levels to go after that.

"Don't worry, honey," Courtney told me. "The boys are at your mother's. I called her and said the babysitter was sick. Could she come and pick them up?"

"Help me get him up on the bed. I'm going to fuck him again," Hannah told Courtney. "Zapping his balls has me as hot as all fuck."

I could see the truth in her assertion. Hannah's long tool was rigid enough to pick ice with.

The girls dragged me onto the bed.

"Up on your hands and knees, slut," Hannah compelled.

Groaning in pain, I managed to comply.

"Spread your knees and lower your ass down. You're too tall."

With no other choice, I did as told.

Hannah squatted over my ass. Holding my butt cheeks apart, she spat on my ring, then used the head of her girl cock to spread the spittle around. Homing onto the centre of my brown starfish, Hannah began to shove her dick into my ass slowly.

Balancing herself by leaning on her hands that she had placed in the middle of my back, Hannah slid all 8 inches into me. About halfway in, the head of her lady cock rubbed over my prostate.

I couldn't help the grunt of pleasure I gave. Even though I was basically being raped, her cock sliding across my prostate felt just as awesome as the first time.

Involuntarily, I pushed back at invading protuberance. As I did, my sphincter relaxed, and Hannah was able to come to rest with her pelvis pressed against me with all 8 inches buried in my gaping ass.

She held still for a moment to let me get used to having her cock in me in this position. I wasn't able to control my urges. I pushed my hips forward, then back at her pubis.

"You want me to fuck your arse, slut?" Hannah questioned.

I nodded, then received another whack with the flogger.

"The correct answer is 'Yes, please, Mistress Hannah,'" Hannah snarled.

My cock was on fire. I'd fucked probably close to two hundred different women in the six years since I turned 18. I'm sure I'd never been this turned on or as hard before.

I shook my head in denial, but then Courtney's warm wet mouth surrounded my todger. Courtney fondled my still aching balls as she deep-throated me.

"I need you to fuck me, Mistress Hannah, please," I found myself begging as the intensity of my feelings overwhelmed me.

"Good slut," Hannah replied. "But you took too long. You may hump my cock and make yourself cum, but I'm not going to help you."

Groaning in pure lust, I humped into Courtney's greedily sucking mouth and back onto Hannah's gloriously rigid shemale cock.

It took a couple of slight position changes before I had the head of Hannah's dick sliding consistently across my prostate, my P-spot, and then it felt like I was in orgasmic heaven. My dick swelled even bigger, I'm sure. It felt full enough to burst inside of Courtney's mouth.

"I'm going to cum," I told the two.

"Not until you beg me to," Hannah growled.

"Please, may I cum, Mistress Hannah?" I pleaded.

Hannah slid her magnificent tool out of my ass and then pushed me over on my back. She and Courtney grabbed an ankle each and doubled me forward and over. My knees were forced back onto the bed beside my ears.

Luckily part of our training is both core and flexibility work. This position wasn't too uncomfortable. I was painfully aware that the eye of my cock was now pointed at my face.

"Try and move, and I'll zap your balls until they fucking explode," Hannah threatened.

She forced her long thin cock down so it could be shoved back into my ass. Courtney leant forward and sucked and tongued my balls as Hannah slid back inside me.

"Make sure he cums over his face," Hannah requested of Courtney.

Hannah started to fuck me again. Her dick was once again scraping delightfully over my P-spot.

Courtney circled the shaft of my cock with her thumb and forefinger then began to jerk me off firmly.

The third time Hannah's head slid over my prostate, I lost the control I was desperately trying to hold on to. With a deep, guttural groan, I began to shoot cum out of my cock. This was the best orgasm I'd ever had. I spasmed at least seven times, spraying cups full of cum every time.

Every single squirt hit me in the face.

"Open your mouth, slut," Hannah demanded. "Swallow every drop that goes in there, or suffer the consequences."

The last three loads all went in my open mouth. It was all I could do not to throw up, but my brain was betraying me. The last three cum blasts were the most intense of a cum event that was already better than anything I'd ever experienced.

"Open your mouth, show you Mistress that you've been a good boy and swallowed everything," Hannah required of me.

Embarrassed, I complied.

"Good boy. Now you can fuck my ass and watch as I fuck your wife's delectably tight ass," Hannah informed me. "She's so fucking tight in there, tighter even than you, that I'm sure it won't take long before I need to cum. When I say 'now,' you will get off me, onto your knees, open your mouth and swallow my load. Do you understand?"

Miserably, I nodded my head.

The problem was, I was going hard again at the thought of sucking Hannah's lady donger.

Hannah pushed her toes against my cuffed balls, "There's a good pet," she said as my wang grew visibly harder. "Already learning to accept your role."