Tranny Babysitter: The Conclusion

Holding a wooden stirring spoon, she came over to us. She lifted the hand holding the spoon to her forehead and wiped some sweat away. Her nipples jiggled sexily as she did it.

"This is Harry," I told her. "Harry thinks you're as hot as all fuck."

I gave Harry a conspiratorial wink.

He blushed but gamely said, "Well, you are, Mrs Murray. All the guys agree."

"Call me Courtney, honey," she said.

She stood on tiptoes, then leant forward to plant a soft kiss on his surprised mouth. Courtney let her hard nipples rub across Harry's forearms as she kissed him.

Hannah entered the room. She had dressed in a crop top that ended in two long strips. She had tied those strips off under her huge melons. Her midriff was bare, with her belly button pierced. She was wearing the tiniest pair of shorty-shorts I'd ever seen.

What she had done with her dick, I couldn't fathom.

Harry gaped from woman to woman, "Fuck me," he muttered. "At least he wasn't lying about how hot the babysitter is."

Harry had another look from Hannah to Courtney and back, "Fuck me," he said again, a little louder.

"Maybe later," Courtney said impishly. "Dinner first, then maybe 'fuck me'."

Harry's tongue needed to be fed back into his mouth. It was currently on the floor.

"I hope you like Spag Bog," She told him. "Carbs for quick energy, lean mince for low GI and protein for building muscle. Grab a seat at the table. Want a beer?"

Harry blinked, "Umm, yes, please," was all he managed to get out.

"I'm Hannah," Hannah said, introducing herself. "It's okay to stare. I like it."

A bemused "Fuck me" was reissued from Harry.

"Maybe later," Hannah echoed Courtney. "But you'll need to beg me to first."

The girls mercifully left Harry alone during dinner, but when Courtney served some ice cream and brandy snaps for dessert, they insisted on taking turns feeding him.

Courtney and Hannah started to 'one up' each other. Hannah started it by dipping her fingers into the ice cream and insisting Harry suck it off.

Courtney took some ice cream into her mouth and then kissed a surprised Harry, feeding the ice cream into his mouth as she did.

Hannah undid her blouse, exposing her braless chest, used her fingers to wipe some ice cream onto her nipples then asked Harry to lick it off.

I think Harry had forgotten I was even in the room.

Courtney finished this round of activities by lifting her skirt above her hips and sitting on the table in front of Harry with her calves over his shoulders and her feet on the back of his chair. She then smeared ice cream across her vulva and clit.

"Well, honey? Are you going to get your dessert or leave me wanting?" She purred to him.

Risking a quick glance across to me, Harry eagerly moved forward and began to lick the ice cream off of Courtney's cunt and clit.

Courtney moaned her appreciation, "That's it, honey-chile. I'm sure there's more cream further in. Better get your tongue right in there and suck it out for me."

I'm pretty sure Harry lost his first load into his underwear at that stage.

"Come on, fag boy," Hannah muttered to me. "Time for you to go have a wank in the closet as you watch a real man fuck your wife. Don't worry, though. Harry's an even bigger fag slut than you. I'll soon have him begging you to let him sit in there with you. He'll probably even want to blow you as he watches."

I eagerly raced up the stairs and into the closet. One of the girls had glued a thick 7-inch, natural skin colour dildo to the stool. There was an envelope leaning against it.

I opened it, then read the note: "If you want to watch, and you will watch, you will strip to naked and then ride this cock the whole time you're in here. Don't even think of not doing it. I've set a cam up so I can confirm that you're obeying."

It was signed with an 'H'.

I looked around and eventually found the hidden cam. The flashing green light had been covered with some masking tape so it wouldn't be seen from outside the closet.

With a large part of my ardour silenced, I stripped as requested, lubed the dildo and my ass, and then held my ass cheeks apart so I could lower myself onto it.

I had taken so many things up my clacker, including the huge one that Courtney had fucked me with last night, that this comparatively small cock slid into me without any protest.

I rocked and wriggled my ass until I felt the dildo hit my prostate. Biting my wrist to muffle my immediate groan, I settled myself down to wait for Harry and Courtney to arrive.

I didn't have to wait long.

Kissing and tearing each other's clothes off, they crashed into the room. Courtney swung Harry around, gave a little leap, and wrapped her legs around him. She leant back, causing Harry to stumble forward a little before regaining his balance.

Courtney's back and ass banged against the glass.

There I was, less than 2 inches, and only a sheet of hardened glass from me and my nearly naked wife, who was about to be penetrated by a teammate I had hardly known until talking to him in the gym less than an hour ago.

I couldn't have been happier or any more aroused. I fucking loved watching my wife being gloriously fucked, and I loved that she loved it.

Harry had entered my wife and was roughly fucking her, shoving his length viciously into her hot, wet, and very tight cunt.

I had taken myself in my hand and had begun lifting and lowering myself on the dildo. In my mind, it was Harry's cock that I was riding.

As that image played in my mind, and with a stifled groan, I came for the first of what I knew would be many times that night.

Courtney dropped her legs and gave a little hip shake to make Harry let her go.

She dropped to her knees, turned Harry sideways to the glass, circled the base of his shaft with her right index finger and thumb, and then cupped his balls in her left.

Courtney pulled insistently up and down on Harry's shaft as she slowly sucked every millimetre of Harry's schlong into her oral cavity. From this close, I could see Courtney's cheeks bulging as she swirled her tongue around and around Harry's cock's head.

Courtney extended the index finger of her left hand and started to finger Harry's taint.

With a surprised grunt, Harry lost his load into my wife's voraciously sucking mouth.

I lost my second load into a tissue as he did.

Courtney tipped her head back and then opened her mouth to show him it was full of his cum. She tilted her head back to level, swallowed, tipped her back and then reopened her mouth to show him her oral cavity was now empty.

"You still good to go, baby?" She asked him. "Or do you need to rest?"

"I'm good to go," came Harry's response. "You've got me hotter than a steak on the grill."

Courtney pressed her tits against the glass right in front of where I was sitting, then pushed her ass back, "Want to try my ass?" She purred.

"Fuck yes," came Harry's guttural response.

"Get your tongue in there, then, baby. Get me ready for your magnificent cock."

I couldn't help myself. I lifted myself off the dildo to lick the glass between me and Courtney's nipples.

My feverish mind was imagining Courtney riding my rigidly hard dick with me licking her nipples as I felt Harry sliding his hard dick into her ass.

I came again.

I then 'joined' Harry on my knees before my wife. I licked the glass where Courtney's pussy was as Harry tongued Courtney's ass.

Courtney's ass obviously wasn't the first that Harry had fucked. He was way too skilled at preparing her for him to be inexperienced at it. I watched in eager fascination as he expertly stretched and lubed Courtney's ring in preparation for penetration.

Harry spotted the sex lube on Courtney's dresser. He quickly covered the head and shaft of his dick with copious amounts of lubricant.

"I'm ready, honey," Courtney moaned at him. "Take my ass."

She turned Harry around so that his ass was against the glass, then turned and bent over.

I quickly lowered my head to the ground so I could look up between Harry's legs.

Harry bent his knees, spread Courtney's ass cheeks with the fingers and thumbs of his left hand, and then took hold of his shaft.

Using his right hand to guide it, Harry introduced the head of his cock to Courtney's rosebud. He slid just a little inside, stopping to give Courtney a chance to say 'no' or for her to adjust to his dick being in there.

He didn't know he didn't need to do that as he had no idea what an anal slut my wife had become in the last few weeks.

"Fuck me, baby. Fuck my ass like you mean it," Courtney moaned.

She wriggled her hips and then pushed her ass back onto Harry's pole.

Harry's ass was right there, I remembered. I could tongue it, or at least pretend to, through the glass. I knelt with my hands on the glass, being very careful not to open the door accidentally, and tongued the glass where Harry's ass was.

Strangely, given my recent experiences pleasing men, it really didn't do anything for my sexual arousal. If anything, it dampened it some.

'Weird,' I thought.

I'd been off the dildo for too long, and I was terrified that Hannah would use that as an excuse to humiliate me with Harry by storming in, opening the wardrobe, and demanding I get my ass back on it, so I lowered myself onto it again.

I couldn't quite seem to find the right spot this time. My ass just felt full, almost like I needed a dump. It wasn't unpleasant, but it just wasn't stimulating, either.

I was considering what it meant when I heard Courtney command Harry, "Come in my ass, stud! Come in my horny slut ass, and I'll cum with you!"

My flagging erection raged again, my ass clenched down on the dildo, causing my prostate to be rubbed beautifully, and I almost came.

Harry was vociferously filling my wife with cum.

"Ahhhhhhhh!!!!!!! ARGGHHHHHH!!!!! AHHHH, FUUCK!!!!" He grunted and groaned. "FUUUUUUCCCKKKKKK! You're one hot fucking bitch!"

Courtney swung him around again, bent at the hips and took him in her mouth to suck him clean.

She 'free-handed' him, using only her mouth to lick and swallow his cum off his cock.

When she spread her ass cheeks to the glass, I knew she had done it for my benefit.

I came again as I watched her push a massive glob of Harry's cum out of her ass.

"I need to pee," Harry said.

"Use the en suite, baby. Wash your cock in the sink, then come to bed. I'm going to blow you so well you'll think I'm about to suck your balls out of your dick."

As soon as Harry closed the en suite door, Courtney slid the door to the walk-in robe open. She took in the stool with the dildo glued to it, and a frown crossed her face.

But all she did was whisper, "Enjoy the show, my cock sucking fag hubby? Now fuck off back to your room. I want to concentrate on enjoying this hot boy without worrying about you falling out of the closet. In the closet, but not for long. I'll have you out and proud soon."

The door to the hall opened, and Hannah walked in.

Courtney shooed me off, then turned to Hannah, "No. Tonight, he is all mine. Next time, you can see if you can seduce him to ladyboy penis," she said quietly.

"You defying me, my little whore?" Hannah responded.

"No, Mistress, but I want this man for myself for one night."

"You will be made to pay for this, slut," Hannah said, then flounced out of the room.

Harry came out just as I shut the door. I listened with my ear pressed against the door.

"Everything okay? He asked. "No dramas?"

"John was just making sure I was happy with the swap, babe, that's all."

"Oh. Are you? I could go and see your babysitter if you'd prefer?"

"You don't want her, honey. Trust me on this one. Let John have her. He's better equipped to deal with her."

Harry sounded crestfallen, "Oh, but ... "

"If I'm not enough for you, you can always fuck off and catch an Uber home."

"What? No, Courtney, you're as hot as all fuck. It's just that John said you and Hannah sometimes get it on, and I've never seen two women going for it before, so I hoped, ya know?"

Mollified, Courtney said, "Maybe next time, just be careful what you wish for, okay? Now, get your taut buns over here and show me how good you are with your fingers and tongue."

I crept back to my room to find a seething Hannah standing there with her arms crossed under her magnificent bosom. She was tapping a finger on her lower arm.

"On your back, hands above your head and clasped together, knees up and apart."

Knowing I was about to receive some of the punishment she had in store for Courtney, I determined to see how much I could take for her. Any of her frustrations that Hannah took out on me would lessen what she took out on Courtney.

I was going to 'take one for the team', team 'Murray'.

"You don't scare me, bitch," I told her. "Do your worst. I can take it."

I took up the required position.

"You're defying me, too? I've obviously been too lenient with you pair of useless fucking sluts. Well, that changes tonight!

Do not move!"

My wrists were handcuffed together and then tied to the headboard. The leg spreader was placed onto my ankles. A thick dildo, about 10-inches long, was shoved into my ass without any lubrication except for what I had already put in there before sitting on the one in the closet. The electric cock cuff was buckled securely around my balls.

Hannah lifted my legs and then chained them to the cuffs. She didn't release the rope holding my cuffs to the headboard this time.

I had a choice: Hold a virtual crunch to stop my legs from hauling severely on the handcuffs, cutting off the circulation to my hands, and putting my shoulders under tremendous strain, or relax the crunch and suffer the above.

I'm supremely fit. It's something I pride myself on. I follow all my training regimes strictly, completely, and faithfully. I diet correctly, do all my stretching and Pilates exercises religiously, keep my alcohol intake to a minimum, and minimise any food high in sugar.

No coach will ever be able to use 'unfit, doesn't try' as an excuse to drop me.

I was too smart to try and hold the crunch indefinitely. All that would do was exhaust my stomach muscles and force me to let my legs haul on my wrists and shoulders until they recovered, if they did.

I held the crunch until I felt the burn, relaxed until my hands throbbed with the built-up blood pressure, and then returned to a crunch.

By the clock on the wall, 10 minutes passed, 15, 20.

There were moans and groans and the sounds of people deliciously and skilfully fucking each other wafting down the hall.

"What kind of fag husband lets another man fuck his wife in the ass as he rides a dildo in the closet?" Hannah asked.

"The kind that loves his wife and wants to see her enjoying herself," I replied.

Hannah pressed the button on the remote, and pain surged through my balls. I hardly even blinked.

"Did you learn how a real man fucks a woman?" She asked. "Or do you need to go back in the closet for some more lessons?"

I laughed, "He's not half the lover I am. Courtney only came once the whole time I was in there. With me, she would have cum three or four times."

I received another, more intense blast.

"Harry gets to cum inside your wife. He can cum in her ass, mouth, or cunt. You can have a wank and cum in your mouth or onto the floor. That's gotta hurt."

I forced myself to smile at her, "Courtney owns me, body, mind, heart, and soul. Even if she told me I was never to orgasm again, I would accept it, as she is my entire world. She and my kids."

The jolt this time was excruciating.

'Fuck!' I thought. 'If that was only 3, I'm never going to make it to 10.'

"Suck my cock," Hannah demanded.

I was willing as I enjoyed sucking her. Strangely, though, I didn't go hard. All I could think of was how sweeter Courtney's pussy tasted than Hannah's dick.

Hannah came pretty quickly as I was now quite an accomplished cock sucker. She pulled out, spoofed on my face, and then took a picture.

"Courtney already has the phone numbers of two of your teammates. Once she has five, I will send this picture to all of them."

I shrugged, "Either you will, or you won't. It doesn't matter. I'm proud of the actions I have taken to please my wife."

I barely managed to stifle my groans of pain.

This fucking bitch wanted me to scream, I realised. She wanted me to beg her to stop. She wanted me to cry out so loudly that Harry would feel he had to investigate and catch me in this position.

'I don't fucking care if my balls fucking explode,' I decided. 'It's worth it if it stops her from punishing Courtney.'

Hannah took hold of the dildo in my ass and began to rip it back and forth.

It hurt, but I was able to lift my hips a little higher. The sawing in and out dildo hit my prostate.

"Fuck yes, Mistress," I moaned. "Fuck your little fag boy."

Hannah tore the dildo out of me and flung it at the wall.

"I'm sorry, Mistress. Has your tranny cock loving, gay boy, submissive slut displeased you? Please, Ma'am, tell this worthless worm what I must do to make it up to you?"

"No," she said. "I see what you're trying to do. You think that if you pretend to like it, I'll stop hurting you."

I couldn't give a fuck if this bitch killed me, as long as she left my wife and kids alone.

She hit the button on the remote. The pain in my balls was so severe that I almost passed out.

She hit it again, and I did pass out.

I came to with Hannah fucking my ass. With a very male-like grunt, she came in me.

Her shemale cum splashed across my P-spot, and I came with her.

"OMFG, yes, Mistress," I moaned. "Please, Mistress, cum in me again so I can cum with you."

Hannah pressed the button again, and I fainted with the pain. I never emitted one word of pain, or complaint, however.

I eventually forced my eyes to meet her gaze, "Tell me, Mistress. Has anyone ever voluntarily cum for you? Or have you had to force, subjugate, or bribe every one of them into cumming?" I asked.

Hannah punched me in the balls. I hadn't realised that the last two jolts had been at full strength. Full throttle, so to speak.

"You think you won't break," Hannah growled in a very masculine voice. "But when I have your wife suffering, you will beg me to stop. I won't. I'm going to fucking destroy her."

"Courtney is way tougher than you," I taunted Hannah. "Do your worst. We Murray's can take it."

Hannah stormed out of the room and left the house. I listened to my R8 screaming its way out of my drive.

I lay on my bed listening to the sounds of Harry and Courtney fucking with a slight smile on my face. I was happy that my wife was enjoying herself and that she had no idea what I endured so that she could.

I knew that if Courtney didn't come looking for me soon, the pain I would suffer would be beyond endurance, but I also knew I wouldn't offer a sound of complaint.

Around two hours later, I nearly reached the end of my strength. My hands were a deep purple because my stomach muscles were exhausted, and I could no longer hold the 'crunch' position.

For the last 15 minutes, I had been biting my lips to prevent myself from crying out in pain.

The door to my room opened, and Courtney stuck her head inside.

"Jaysus!" She exclaimed and then rushed over to my side.

Courtney lifted my legs to relieve the pressure on my wrists. Blood began to pour out of the capillaries of my hands and up my arms. The pain was extreme but felt like a release.

Crying, she said, "I can't unlock you. I don't have the key."

"Get a knife to cut the rope holding my hands to the headboard," I calmly said to her. "Once I can settle into the same position as last weekend, go and get the spare key you put in the box."

I didn't know if she had done that, but I needed Courtney to calm down and think.