Admittedly I was a bit cautious to even touch her hair, despite the appropriately sexy bob hairstyle she wore.
What the fuck was I doing???
Yes, I had requested to rent her for the hour.
Yes, I had talked with the owner for weeks to set this up.
Yes, I had some reservations initially.
But, I was getting a truly a novel kinky experience – which honestly is hard to come by when you’ve been at this kinky fuckery as long as I have been! And I was on vacation.
So, yes, I kind of had to rent her, even if only for an hour.
I looked over at my new sissy boy. He was caged as instructed, wearing a pair of booty revealing pajama shorts and a matching pink mid drift tank top. Oh, and how could I forget the gimp mask with an attached platinum blonde ponytail to finish the look.
As I put out the items I planned on using; paddle, strap on, claws, condoms, and lube, I glanced at myself in the mirror.
‘DO AS DADDY SAYS’ read the reflection of my own tank top and I knew he had no idea what I would be saying right now.
“Well?” I gestured to the feminine figure, face down, ass up, on the clearly well used bed.
“Yes, Mistress?” he responded softly.
I gestured harder, as if that would help. I was honestly holding back a fit of giggles. After the 10 minutes we spent upon arrival just laughing at the absurdity of this play date, with a total stranger, I didn’t want to derail us again.
“Greet Gretta,” I ordered.
“Hi Gretta!” he boomed enthusiastically as he raised his hand to slap her perfectly round ass. Luckily, she didn’t make a peep as told.
“Hey, now!” I corrected him. “You do not have permission to touch her like that. Be respectful,” I said glaring at him down the bridge of my nose.
“Yes, Mistress. I’m sorry Mistress,” was all he managed to eek out with blushed cheeks.
Her role here was to be a silent sex object and for that she was excelling. I watched him lean down to offer a mostly sincere apology. His heart wasn’t in it but I didn’t care about that at the moment.
“Now get on the bed next to Gretta and assume the position.”
“What position Mistress?” he asked through the mouth hole of the gimp mask.
I pointed my long black polished nail at Gretta’s unabashed stance, face down, hips spread wide, bouncy ass high in the air. He mimicked her perfectly, protruding his own small but highly spankable ass out. I gave him a few warm-up spankings with the leather paddle and then focused on what I really orchestrated this scene for.
“Sit up slut and lay on Gretta,” I said sternly. Him and Gretta both looked back at me, her with a blank stare.
He looked confused for a moment before doing as I instructed while I stepped into a pair of red, silk panties. I took out my strap-on in front of them both and lubed it up nice and slow.
“Oh don’t be shy slut,” I said as I pushed his body closer to hers and moved his arms so they were on either side of Gretta’s very curvy body.
This was on purpose. I’d already told him not to touch her without permission, now let’s see if he could resist with a pair of perfect breasts, literally at his fingertips. I was taking my time climbing on the bed, as three bodies on a full size bed was not ideal but it was all we had. He attempted to turn and look at me, she did not. I shoved his head down into Gretta’s back.
“Keep still slut, you’re here to be used, now eyes forward,” I reminded him as I found his sweet spot using the head of my strap-on.
I applied nearly effortless pressure before I could feel his sissy hole give in.
“Wow sissy, I think Gretta is going to be tighter than your slut hole,” I teased as I pushed further in.
He let out a soft moan and nodded his head. I could tell he was already feeling very submissive given the newly strange and amusing circumstances. I grabbed his hips and firmly pulled him back into me and slammed my strap-on deeper while still being mostly mindful.
“Are you going to be a good fuck toy?” I asked, spitting on the back of his gimp mask.
Before he could respond I picked up the pace, I could definitely see why boys favored a fast and hard fucking as givers. Definite power move. I looked at my own soft breasts bouncing in the mirror and smirked. I used that as a cue to wrap my hand around his throat carefully.
“I want to be a good tight sissy slut for you,” he half whined.
“Show me then,” I said taking my strap-on out of his ass, only to open it again for my projectile spit.
I mostly stopped because of the angle, again the precariousness of the bed was the main culprit. Fucking him this hard was wearing out my thighs with no room to move them. I got up and removed the panties and the strap-on, and retrieved the new cock I had been training him to suck nearly nightly.
“You’re going to be Daddy’s good cock sucker, that’s the only way you’ll be of any use to me.”
With this statement I walked back over to him, admiring the future to come, his mouth wrapped around cock for me. I placed the 8 inches of thick, veiny, brown cock in front of him on Gretta’s back. She didn’t stir.
“Gretta’s being a good girl, now you will too,” I leaned in and whispered as I guided his sissy mouth to the stunt cock.
He moaned with delight. Admittedly, that sound is what turned me on the most when I was enjoying turning him into the cock sucking sissy servant toy we both wanted him to become. Step one was getting that pesky gag reflex of his to tamper down. I increased the force of my hand on the back of his head. He took more in. This was one of my favorite things to watch closely, the excess drool running down the cock he was sucking and him lapping it up neatly. Certainly tickled my wet and messy fetish.
I grabbed a fistful of the hair attached to his gimp mask pulling his head back towards me, craning his neck into a stress position.
“That’s enough for Daddy, you’ve been locked up for almost all of Locktober and I want to reward you,” I teased.
I could see his eyes light up as I took the hidden key from my bra, unlocked the cage and freed my property. He was still hoovering over Gretta, who, bless her, had barely moved an inch. I ran my hand over the cock he had just sucked covered in his own spittle and used that as lube to get his sissy cock mostly hard. He was a little shy with Gretta being present but when I produced the condom I’d brought along his member twitched in anticipation.
I ran my hands and fingers along Gretta’s cheeks and between the folds of her lips. She was warm but not as wet as I wanted.
“You’re not even turning Gretta on,” I mocked, stopping to slip a finger inside her in case it helped. I pushed him upward so he was more or less kneeling on the bed, replaced his hand where mine was.
“Hold my place,” I ordered.
I continued getting him hard with the other hand and gingerly placed the condom on him. I was pretty sure this was his first ever wearing one. He was after all my little slutty sissy virgin.
“Since Daddy got to fuck your ass, you’ll get to fuck Gretta’s. I want to keep you a virgin and this seems like the only way to ensure that,” I purred in his ear.
I lightly rubbed the lube from the condom onto her ass and slapped it hard making a loud ‘POP’ in the air. Gretta was unfazed by my dominance. He paused looking at the glistening ass before him and scooted closer. I watched as he struggled to stuff himself inside her very unyielding hole.
I chuckled to myself, she wasn’t making this easy. Then I let that chuckle into the air out loud.
“You can’t even get hard enough to fuck a desperately willing tight hole,” I laughed in his face.
He tried harder to wiggle in but I could see there was no way he was fitting inside her, she wouldn’t let him. We hadn’t discussed this before but I found it highly amusing that she simply would not open up wide enough for him.
“What’s wrong sissy?” I taunted again.
His eyes cast down to his pathetic penis as I came in close to bite his lip. I put his hand on my property, got back on the rickety bed and bent him back over. Now it was all three of us, a sissy sandwich, with him between two big breasted beauties.
“Let’s try this again sluts,” I told both of them not waiting for any response.
This time when I put my strap on inside him, his face was pressed against Gretta’s back and he was allowed to manually stimulate himself outside of her body. I kept my rhythm up, not allowing any breaks in motion. This subtle difference was enough to get him close to the edge.
“Daddy I’m close, may I come?” he asked breathlessly.
I didn’t reply.
He asked again.
I still didn’t reply.
“Please Daddy I’m very close,” he begged.
I looked over at Gretta to see what she thought but her face was mostly being pushed into the pillow from the weight of us both. Did I want him to come or did I want him to ruin?
“Daddy…Da…Daddy,” his pleas echoed.
“Fine slut, but you’ll owe me a ruin if I let you have this a full one.”
“Yes yes Daddy, of course,” he agreed without hesitation
“Beg for it!” I barked still not breaking my porn worthy pace.
“Please…Daddy…please…may I have an extra ruin orgasm this month?” he said with ragged breath.
I was silent.
“Please Daddy you’ve been so kind…” He was toiling to get the words out as the waves of pleasure creeped steadily over him.
“…You’ve locked me up, taken care of me, teased me…”
I slapped his ass in between my strokes now.
“You even let me play with Gretta. Please I’ll do anything Daddy.”
“Good girl,” was all I said.
He knew in this instance that meant he was granted a release and without further words I could feel his body do just that. He shuttered between Gretchen and I as I pulled myself out of his ass. He collapsed a little deeper into her back, the used condom dangling between his legs.
“That’s it slut? That’s all the sissy come you have? Wait until Gretta sees this, it’s pathetic.”
I helped remove it but not before dipping my finger into it and making him lick some off.
“Thank you Daddy,” he mumbled curling up into his usual position after being used. I curled up with him.
“You aren’t going even invite Gretta to our aftercare?” I asked half jokingly.
“She’s just a lifeless sex doll Daddy, you have your own doll now,” he said as he buried his face into my chest snuggling into my flesh deeper.