Tranny Babysitter: She Owns my Ass

Before too long, he was entirely inside my mouth, with my lips against his hairy abdomen. I cupped his big balls with one hand and pushed and pulled with my other on his hip, encouraging Roger to fuck my mouth. Working slowly, Roger moved his hips back and forth, sliding his length across my lips and tongue, past my gag reflex, and down my throat.

Roger groaned deeply and lustily, "Fuck, that's good. Only one other has ever been able to swallow me whole."

I felt a hot breath at my rosebud, followed by a wet tongue. Hannah tongued my chocolate starfish before she started to work her finger into my partially stretched ass. My 'boy cunt' had been able to accept her thin ladyboy penis quite comfortably, but Roger's massive wang was another matter.

Working quickly, Hannah added a second, then a third digit. Forcing her fingers wider, Hannah stretched my ass enough to be able to take Roger's large cock.

Hannah took the tube of lubricant off the top of the dresser and smeared it over Roger's head and shaft.

"Fuck this slut's ass,' Hannah told Roger. "I'm going to get on my knees beside her. Feel free to fuck me as well."

Roger moved behind me as Hannah took position beside me. Copying her actions, I pulled my thong far enough down that my rear fuck canal was exposed, but the tape holding everything in place wasn't. In passing, I noticed that Hannah had done to herself what she had done to me. She'd taped her balls into their canals and taped her dick back along her perineum.

I felt the head of Roger's huge wang against my ring.

Fearfully, I turned my head to Hannah,

"Just relax and clench down rhythmically on his tool as he pushes into you, baby girl. Once he hits your P-spot, you'll be gone," she whispered to me.

The pain as Roger forced the head of his massive cock into me was extreme. I grunted, and tossed my head.

"You want me to stop, Miss Olivia?" he asked.

In reply, I clenched my ring down on his cock's head and then relaxed it before pushing my ass back at him. Another three inches slid into me.

Gasping, with my eyes watering, smearing my mascara down my face, I struggled not to squeal and demand he withdraw. But something had gotten hold of me. I wanted to be fucked by this tremendous tool, submit to the power of the penis, and to be Roger's baby girl ass slut.

I forced my ass back another inch.

The head of Roger's massive dick rubbed across my prostate.

This time I grunted in surprised pleasure. The pain hadn't gone away, but it was being subsumed by the pleasure my P-spot was receiving and the signals to my brain to release endorphins it was sending out.

I took a deep breath, exhaled slowly, relaxing every muscle I could, and shoved my ass back at Roger hard.

His hairy abdomen hit my waxed ass cheeks. I'd done it, taken all of Roger's giant thick magic fuck stick in my boy cunt.

Hannah kissed me, "Well done, little one, you ready to be fucked?"

I nodded eagerly. Roger's tool was pressed hard against my prostate and pulsing with Roger's arousal. This caused the shaft to stimulate my P-spot deliciously. I couldn't wait to feel it scraping over my prostate as Roger thrust that massive tool in and out of me.

Roger placed his hands on my shoulders, moving only a small distance back out of me at first. He then began to pull me back onto his pelvis as he thrust back in. His enormous fuck pole was dragging delightfully across my prostate.

Trying my best to moan and groan softly so that it wasn't apparent that I was a man, I began to involuntarily push back at Roger's dick as he pumped it into me.

My cock was tearing at its binds it was hardening so much. The pain of this, and the ache in my taped balls, seemed to only add a poignancy to the pleasure my P-spot was receiving.

Roger built up momentum. Before long, he was pushing and pulling at least half of his shaft in and out of me. I wanted more, so I started moving my hips forward as he pulled back, slamming my ass back at him as he shoved in.

His abdomen began to slap against my ass as he fucked me harder and harder. I love that sound. It usually means I'm ploughing some slut for all she was worth, but now it was me being ploughed, my 'cunt' full of cock, and my moans that could be heard.

I was the submissive slut to a dominant man, and I fucking loved it!

After one particularly vicious thrust across my prostate, I couldn't help myself, my mouth fell open, and I moaned lustily. It was fucking evident Roger wasn't in a woman, but he didn't stop. He just fucked me harder. My moans rang out again and again.

Unknowingly, I had closed my eyes to revel in the sensation of being beautifully and totally fucked. I heard moans other than my own coming from next to my right ear. I opened my eyes and turned my head to look.

Roger was groaning, and I could hear the sounds of pelvis against ass that wasn't Roger's against mine. I let my left arm sag so I could put my shoulder on the bed and try and peer past Roger to see what was going on.

Hannah had stripped to naked, ripped the tape off, and was busily pounding Roger's ass with all of the 8 inches she had.

I'd been set up again. Roger was one of Hannah's femmeboy fags. She and Courtney had chosen him for my first gay lover because they knew he wouldn't be bothered by my masculinity or care when it became apparent that I had a penis and no cunt.

All of tonight's performance from when we got to the restaurant had been a sham. A construct to have me willingly let a man fuck me.

Roger was still fucking me, but he was way too invested in the pleasure he was receiving by being 'rogered' by Hannah's long slim tool to concentrate on me.

Desperate to cum, I found an edge of the tape holding my balls and shaft down. With a grimace of pain, I ripped the tape off, and my thick 7.5-inch cock immediately sprang to full attention. My balls slithered out of their canals and took their place along my shaft in the 'ready to cum' position.

I took myself in hand and began to thrust my ass back and forth on Roger's huge dick. I had to shift positions a couple of times before I had it sliding across my prostate all the way in and all the way out.

I found the right spot, and my cock erupted. Groaning in ecstasy, I shot glob after glob onto the bed. I spurted at least seven times before the spasms ran dry. I must've cum at least three more times after that as Roger's magnificent rod sent explosions of pure pleasure through my P-spot and into my brain.

My sphincter gripped tightly on Roger's cock's head as I orgasmed. This extra tightness, and the pulses of my ring, sent him over the edge. With an even louder moan than mine, he began squirting into my ass.

Feeling his semen splash over my prostate sent me into another frenzy of orgasms. I spat only a bit of semen from my now mostly empty ball sack, but even without spurting, these events were fucking awesome. I groaned lustily again.

Exhausted, Roger slid slowly out of my ass and rolled onto his back. Hannah's cock fell out of his ass as he did.

Hannah straddled my chest, her ass resting on my breast forms.

"Suck me off, slut," she demanded.

Despite her beautiful ladyboy penis having just come out of Roger's arse, I quickly gobbled her down.

Hannah held the back of my head and began to thrust forcefully into my eagerly sucking mouth. I wanted to receive Hannah's gift so I could thank her for procuring so much pleasure for me. Never in my life had I had such a momentous cum event. I wanted to experience more.

'You may not have been a nancy boy when you woke up this morning,' I thought. 'But you're sure as hell one now.'

I cupped Hannah's balls, then stretched my finger along her perineum so I could rim her boy cunt. Twirling my finger around her rosebud, I swirled my tongue around her cock's head and glans before bobbing the whole length of her shaft in and out of my mouth.

Hannah squeezed my lips and nose painfully against her pubic bone before, with a deeply satisfied groan, unloading a torrent of shemale sperm into my mouth and down my throat. I gleefully swallowed it all.

"There's a good little fagboy queer," she told me. "You haven't completed your duties, though. You left Roger's cock all messed up. On your knees, and suck him clean."

I almost lovingly licked, nibbled and sucked Roger's sperm off the head and shaft of his gorgeously long and thick cock. Hoovering his juices off his balls and groin area, interspersing little kisses and sucks on his cock's head and shaft, just because I couldn't help myself, soon had Roger's dick showing signs of recovering.

I took his thick shaft in my hand and began making him hard again. My sphincter was already clenching rhythmically in anticipation of receiving this huge magic stick again.

Pumping his shaft and swirling my tongue around his cock head soon brought Roger to full attention. He pushed me off his dick and onto my back.

I lifted and spread my legs just like a woman would and took hold of the shaft of his cock to guide it into my backdoor fuck hole.

Feeling that stupendous tool sliding into my ass gave me a weird feeling of completion, as if taking my man's tool was my job, my offering and my gift to him. I felt so sexy, slutty, and submissive. Fuck me. I felt so feminine.

Dressed as I was and submitting to a masculine man, giving him full access to all my holes felt natural. It felt like it was only fitting. I moaned like a bitch as the head of his giant cock slid across my prostate and into place buried deep in my ass.

I wrapped my legs around the back of Roger's calves and pulled him into me.

Taking the hint, Roger began to fuck me. I grunted with delight every time his pelvis hit my ass. His hitting my ass cheeks completed the journey across my P-spot in the one direction. Now the shaft would be dragged exquisitely across my prostate for almost nine delicious inches before beginning its descent back into me.

A dick was poked at my cheek. Turning my head, I let all of Hannah's gorgeous ladyboy penis slip across my lips, over my tongue and down my throat.

I sealed my lips around her shaft and sucked insistently. Flattening my tongue out, I surrounded as much of Hannah's dick as I could. Giving her hip a bit of a push had Hannah pumping her cock back and forth. By her appreciative moans, I could tell it wouldn't be long before I was given my cum reward again.

With another huge sigh, Hannah blew into my mouth. Her load seemed undiminished as I joyfully swallowed it down. Hannah dropped onto her back with a satisfied groan.

Roger slowly sagged until all his weight rested on my stomach and tits. I lifted my legs higher and wrapped them around his hips.

Roger kissed me tenderly, and I eagerly returned the kiss. We pashed like star-crossed lovers as he gently fucked my tight ass.

This new angle made his cock press even more firmly on my prostate. I was in seventh heaven. Groaning with delight, I fell off the edge into bliss. My cock erupted between us. Squirting copiously, I soaked both Roger's and my stomachs.

Feeling me cum was too much for Roger. With a groan as deep as mine, he came in my ass for the second time. I was almost disappointed because I would have liked to taste him.

"Don't forget your duties, my little fag," Hannah reminded me.

I got up on my knees and sucked Roger clean. I even gathered all of my cum from his stomach and abdomen and swallowed that, too.

I ran my tongue around the head of his cock and lapped at the eye in the hopes he could go again. It seemed like I just couldn't get enough of his magical fuck stick,

I stopped when I heard Roger softly snoring.

Now we were quiet. I could hear a rhythmical thump, thump, thump coming through the walls. Josh was giving my wife a proper royal fucking. As well as the thumps, I could hear her moaning, "Harder, harder, oh fuck, that's so good. Fuck me harder."

I started to harden, but it wasn't at thinking of fucking Courtney or Courtney being fucked. I wanted what she had. I wanted Josh's cock in me.

Hannah noticed my thick dick rising to the occasion again.

"I haven't been fucked tonight yet," she said. "I've only cum in a mouth and an ass. Do you want to fuck me?"

'Do bears like honey?' I thought.

I lowered myself down so I could take Hannah back in my mouth. Once she was nice and hard, I encouraged her to roll over so I could prepare her boy cunt to be penetrated.

"I'm going to let you do me doggy, my little cum slut," she told me. "When I tell you, I want you to pull my hair and smack my ass. Don't think for a moment this changes our roles, though. You're still my fagboy bitch."

"Yes, Mistress," I replied.

Hannah got up on her hands and knees. I took my position behind her ass and guided my thick cock into her ladyboy pussy.

"You have such a great cock, Olivia. No wonder Courtney put up with you fucking around on her for all these years."

Rocking gently, I started to fuck Hannah's extremely tight rear pleasure hole. Hannah was clenching and releasing her sphincter on my cock as I slid in and out. It was fucking awesome, but I didn't need her to tell me what would happen if I came before her.

I hoped I would get to cum into Hannah's delectable ass, but I suspected the hope was a forlorn one.

Hannah wasn't reacting to my cock as well as I had hoped, so I shifted angles slightly. Hannah responded with an immediate grunt.

"Fuck yes, right there. OMFG! Yes, that's it, fagboy, do me, and do me right now!" She growled.

I grabbed a handful of Hannah's long blonde hair and hauled her head back. I followed that by smacking her ass hard.

Oh my lawd"," she moaned. "I'm going to cum. On your back, slut boy."

I flipped quickly onto my back, spread my legs, and opened my mouth. I wasn't sure what hole Hannah wanted to cum in, but I wasn't taking any risks in offering up the wrong one.

Hannah pushed my legs back and placed the back of my thighs over her shoulders. Taking hold of my todger, she slid her long thin tranny penis into my well-gaped ass. Because I hadn't jumped as her dick slid in, Hannah lifted my legs a little higher and squeezed them together.

The next time she slid into me, her dick hit my prostate. My moans instantly mirrored hers.

It didn't take her long before she unloaded into my hole.

Hannah sagged down, letting her cock fall out of my well-used ass.

I hadn't been able to cum, so my erection was still rampant. Hannah placed the toe of her high-heeled shoes against my balls, pushing on them to the point of pain. I didn't dare move.

"Does my faggoty little pooftah slave need to cum?" She asked.

"Yes, please, Mistress."

"You can have me double you over so you can suck yourself off or cum in an ass. What would you prefer?"

Without thinking, I replied, "Cum in an ass, please, Mistress."

"Very well," Hannah told me. "Help me roll Roger over. The fag loves being fisted, so, with a little lube, you should slide straight in."

I looked at her, horrified. I didn't want to fuck no man's ass!

Hannah pushed even more firmly against my balls.

With a raised eyebrow, she said, "You defying me, slut?"

"No, Mistress," I quickly averred.

"Then what are you waiting for? Help me roll Roger over so you can fuck his ass."

Roger was already naked, so it was a simple task to roll him over and push his thighs together so I could spread mine around his and access his rear fuck hole.

I was slowly deflating at the thought of fucking a man in the ass, but Hannah wouldn't allow that. Telling me to lie back and hold still, she squirted a good-sized dollop of lubricant onto her hands. Working the lubricant onto the fingers of her left hand, she slid two fingers into my ass. Finding and then massaging my P-spot, she took my softening tool in her right hand and began to stroke me off.

I tried to cum, so I wouldn't have to fuck Roger, but when I thought I would pop over the edge, Hannah removed her fingers and released my shaft.

"Get to it, fagboy. Once you're inside, you'll find it's just as nice as a woman's."

Crying, but desperately needing to cum, I covered Roger's body with mine. There was a little resistance at his knot, but I pushed a little more firmly, and the head of my cock popped through, and I slid in.

Hannah was right. Roger's ass around my hard cock felt no different to any woman I'd been in.

Roger awakened as I slid into him. I had wrapped an arm around his neck to balance on. Roger grabbed my arm and then kissed it.

"Hmm," he said. "What a delightful way to be woken up. I hope you're not a two-pump chump, Olivia."

Roger lifted his hips high enough to slip his hand under his body and grab his cock. I could feel him wanking himself under me.

"Fuck me, baby girl," he begged. "Make me your bitch."

My balls were aching, and the head of my cock was throbbing with the need to cum. In the end, I closed my eyes to try and think about something else to distract myself from knowing what I was doing.

Me, John Murray, super stud and footy star, fucking some poofter's ass.

I thought of all the babysitters I had fucked and couldn't get close to the edge. I thought of the night I had deflowered Courtney, usually a guaranteed cum vision, nothing. I relived deflowering Courtney's youngest sister on her 18^th birthday as Courtney slept not three feet from us, still nothing.

I remembered doing her sister for the second time on Courtney and her mother's kitchen bench as the rest of the family, including Courtney, watched TV in the lounge, just an open door away, and couldn't get there.

Finally, I thought of Josh pounding Courtney just a couple of bedrooms away. But it wasn't Courtney that he was hammering in that room. It was me.

I came like a fucking freight train. I couldn't help myself, and I almost screamed my way through my orgasm. It was so intense.

"There's a good girl," Roger moaned. "Do you want to swallow my load?"

In a daze, I rolled off of him. Roger got on his knees and offered his penis to my lips. Raising myself on an elbow, I accepted the head into my mouth and held his shaft about halfway down its massive length.

Pumping his shaft, I milked Roger until he exploded into my mouth.

We cuddled up on the bed, Roger spooning me, Hannah facing me with her head on my upper arm and shoulder. It was time to get some much-needed sleep.

End Part I