Sissy Step Dad - Ch. 01

"A sissygasm? Oh Teddy, you really are too much."

The cock in my ass started to fuck me in slow deliberate strokes; clearly she was giving signals of some kind. In and out. In and out. Too slow, it was not enough. I tried to move to change the pace, but I was strapped down too well and couldn't move. A moan of frustration escaped my lips.

"So tell me Teddy, have you ever had a sissygasm?" I pictured her twirling her hair as she asked.

"Not until today mistress, when you fucked me earlier."

"That's right," she gushed. "You blew a huge load while I rammed that baseball bat in and out of your sissy cunt. And no one even touched your clitty. You came just from being ass fucked." She sounded like a school teacher admonishing a student. "Did you enjoy that sissy?"

"Yes mistress."

"Yes, just yes?" and the fucking stopped. I moaned in frustration.

"Please don't stop. I need to be fucked," I whined.

"Well then, tell the truth about this morning sissy," it was a command not a request.

"It was the most intense orgasm I've ever had mistress. It was incredible. I came for what seemed like minutes; and over and over again. It was beautiful and I want to experience it again, and again. Please give me another sissygasm Mistress." I was begging and pleading and telling her the absolute truth. I really did want to experience that feeling again. I hadn't even realized it until now. The day had just been too chaotic for me to even think about it.

The fucking started again, this time in earnest and with force. The speed picked up and you could hear the flesh slapping, when the strap-on driver's hips and my ass came together. Whoever she was, she definitely knew how to wield a strap-on, but I wanted her to grab my hips and really lay into me.

"Please grab my hips and really drive it into my cunt. Rape my ass. Please!"

"Sissy! You are here to be fucked; not to make demands. You will be fucked as a piece of meat and if you orgasm it will be because we are merciful, not because you deserve it or beg for it!" Danni was in front of me again and I felt her strap-on touch my lips.

I opened my mouth willingly and wantingly. Desperate for more stimulation. Danni wasted no time teasing me this time and slid her cock deep into my mouth. She got into a good rhythm with the person fucking my ass. Skullfucking me this time; not relying on me to do the work. They were stip-roasting me. Glorious spit-roasting! Laura has done this a few times; the fucking machine in my ass and her fucking my face. But this was a new level.

With every thrust, Danni was berating me, degrading me, and spurring on the person that was fucking my ass. "Take it bitch. You sissy faggot. Fucking cum slut. Dirty anal whore. Ram his sissy cunt. Drive that cock into his ass pussy. Make him your bitch. Breed the faggot." Ramming her own strap-on into my throat to punctuate each sentence. But she was pulling out enough so I could breathe.

I could hear Danni's breathing increasing and her voice quavering. I sensed her orgasm was approaching. Suddenly, the person fucking my ass grabbed the strap across my back and I felt finger nails scrape as she did. She started bucking hard into my ass and came to a jerking halt. I assume she had an orgasm. I groaned around Danni's cock. I needed the ass fucking to continue.

Then, Danni rammed her cock down my throat a final time and started to buck, also apparently having an orgasm. I could smell her pussy and wanted desperately to eat her. But more than anything, I wanted, no needed, my ass fucked. I really was becoming an insatiable anal whore.

I laid still, like a good sissy meat puppet, hoping, praying, that Danni would do something to ramp it up and get me off.

"Well sissy? nothing to say?" Danni asked.

"Thank you mistress, I hope you and your friend enjoyed your sissy slut."

"You're learning fast sissy. No pleading or begging, just acceptance. That's good. But I need to know, did you enjoy your ass fucking? Was it enough? Or are you now a size queen that needs huge cocks to satisfy you?" Followed ominously by, "Answer truthfully or you'll be punished."

"Mistress, it was an awesome ass fucking. Done by someone that knows how to fuck. But as you suspect, I have become a size queen. I would love for a huge cock to ravage my ass," which was the truth. But I seriously hoped my answer was phrased correctly, and that I hadn't pissed her off by insulting her friend.

"Well said sissy. There's hope for you yet. However, there's only one huge cock in this room; and you don't deserve it. And just to be clear, no more baseball bat, the only thing going in your ass is cock." Danni stroked my cheek.

"Please mistress, fuck me with your big black cock and show me your power and skill. Make me moan with pleasure and beg for more," I was desperate for more cock in my ass.

"Oh sissy, you misunderstand. My cock isn't the biggest, not even close. No... someone else in this room is truly packing; and I don't think your ass can take it. Also, you definitely haven't earned it." She was mocking me, but also letting me know I needed to do more groveling if I wanted to get off.

"Please mistress! I can take it! I need it!" I was getting desperate. "I need a huge cock to rape my sissy man cunt and make me a woman. Please have your friend rape my ass. I promise I'll beg for more no matter what. I'll... I'll suck my ass juice off the last cock that was in my ass. Please I beg you! Unleash the monster cock on my ass and make me your sissy slut forever." Danni may have initiated the gender bending role play, but I was totally getting into it.

"Forever sissy? You're on dangerous territory with that statement." She chuckled. "I'll let that go for now, but you need to convince me, and everyone in this room, that you want a huge cock buried deep in your sissy ass."

"Mistress, I swear, there is nothing I want more than a huge meaty cock in my sissy cunt. To use my pussy to squeeze their shaft and milk it. To make the cock's owner moan with pleasure, as they rape my sissy cunt. To squeal in delight as I'm ravaged by a huge manly cock in my dirty little sissy hole. The thought of it is making me hard and wet. Check my sissy clitty, I can feel it leaking. I'm getting so horny, I feel like I might cum just from begging for the cock. Please Mistress! Have your friend fuck my eager sissy cunt." God, all this dirty talk really was getting me off.

"Well Teddy, that's quite the speech. It seems everyone in the room, except me, believes that you've earned the cock. However, before I allow this, I need you to know understand the rules. If you beg for the cock again, you lose all control. You will be fucked. You have no say in when it ends. And if you say anything other than how much you love it, you'll be gagged until it ends." Danni warned.

I was wondering how big this monster could be. I had seen some enormous strap-ons and dildos during my porn watching and the size of some had been truly frightening. But I had taken a baseball bat just a few hours earlier, and loved it. How much bigger could it be? Fuck it I thought. I was desperate for more action and another sissygasm. I wanted this. No, I needed this to happen.

"I understand Mistress. Not only will I not stop it, but I promise not to scream or cry out. I want this, no I need this. Please Mistress. Please." My last word sounded like a 7 year old pleading to stay up late.

"Okay then..." she drawled out. "But remember sissy, you not only asked for this, you begged for it. Proceed!" she ordered to the room.

I felt a bunch of lube being dripped on my ass. It was different. It seemed warm and seemed to be getting warmer. My back was also getting warmer. I realized that they probably had a light over my lower back pointed at my ass for better lighting, and that the light was heating things up. Then two hands pulled my cheeks apart, while another two started fingering my hole. Two fingers; then four; then six; then all eight fingers. Working from side to side and in and out. Stretching me. Loosening my ass. They pulled my hole apart and poured a bunch of lube directly into my ass; it was almost hot. Then they worked me some more.

Everything stopped. There was no noise. Nothing touching me. No one talking or moving. It was intense. Like everyone was waiting for a free-throw or penalty shot. Waiting. Holding their breath. The tension built.

A huge rock hard log fell on my ass crack. Just like the baseball bat earlier, but this one felt like a dildo. Hard, but with some flex. Like the lube, it was also warm. Probably covered in more warming lube. I didn't think it was as big as the bat, but it was hard to tell. Maybe the length was what Danni had been warning me about. Oh shit I thought. "Mistress! I'm worried about the length," I blurted.

"Silence!" She cried still standing by my head.

"But..." and the penis gag was shoved back into my mouth before I could utter anything else. She had warned me. I had begged and pleaded for it and now I was going to get fucked. No backing out. I was about to struggle, when I remembered the crop.

The log started sliding along my ass crack. Back and forth. Back and forth. Stopping briefly each time as the tip reached my pucker hole. I was getting excited again, and they could tell.

The next time the cock reached my hole, it paused and changed angle. It pressed against my hole, not hard, but persistent. It may have been big, but the head was rounded, unlike the bat, and it started to enter my asshole fairly easily. Danni rubbed her thumb across my cheek, and I realized I was holding my breath. I relaxed and pressed out, like I was taking a shit, hoping to allow entrance to the monster cock without pain. It continued to ease forward and the head popped passed my sphincter. Just a slight pinch of pain, but it lasted only an instant. I sighed and moaned with pleasure, as I felt the cock slide deeper and deeper.

It stopped, about five or six inches deep, and started to pull back out, until just the head remained in my ass. Then slowly the fucking began; to the same depth each time. It was rubbing my prostrate with each stroke. I was moaning and drooling like a complete slut. I was in heaven.

"Nod if you're loving this sissy." Danni demanded. I nodded furiously. "Do you want more?" Again I nodded yes. "You truly are a gifted sissy fuck slut." she chuckled. "Fuck the cunt!"

The pace increased. The cock drove in and out faster and faster, but the depth never seemed to change. I started to wonder if it was attached to the fucking machine, but then I felt sweat dripping on me. It was a person and they were fucking the shit out of me with a huge strap-on, but it was definitely a person.

Danni started to get involved. "Fuck that sissy cunt. Breed him. Make him your cock toy. Make the faggot beg for mercy. Rape his pussy. Deeper! Come on... bottom out in his man cunt."

The cock started to go deeper There was a bit of discomfort, but it subsided after a minute, and there was only pleasure.

"Do you want it deeper sissy? Come on... moan like a sissy whore if you want more. Let your mistress know that you want more. I know you want it. I can feel the lust pouring out of you."

I moaned into the gag. Over and over. Desperately trying to convey that I wanted more. I wanted it deeper, faster, harder. I needed it. The combination of degradation and ass fucking was taking over my mind.

"Listen to you moan... like a two-bit whore. You really are a sissy cum slut. I really wish that you weren't gagged. I'd love to shove a big cock in your mouth and spit-roast you. Make you the meat in a cock sandwich. Watching you drool and slobber all over a big manly cock while your ass pussy gets raped. God, I'm fucking wet just thinking about it."

Her dialog was driving me crazy. I did want a big cock in my mouth. To be spit-roasted. To be the meat in her cock sandwich. She was a virtuoso and I was her instrument; being played; making her beautiful music. I would have done anything for her at that point. It was pure ass fucking ecstasy. Destroying my mind. I was moaning in bliss with each trust. A bitch in heat.

"Well, the pussy definitely wants more, so give her everything you've got. Long dick the bitch!"

A final push and their hips met mine. They were fucking the shit out of me; ramming me into the A-frame with every thrust. A pair of hands gripped my hips and they started driving harder. Big hands. Too big. And then I noticed something slapping me between my ass and balls. My eyes flew open in recognition - hairy balls! Oh fuck! I was being raped by a guy! I started to thrash my head and try to move but I was too well secured and only my head moved. The fucking continued unrelenting as I tried desperately to get lose and away from the cock. Completely freaking out.

Two hands touched and held my face. Firmly, but gently; reassuringly. Then Danni's voice in my ear. "Don't sweetie", she whispered, "Just seconds ago, you were loving this. Don't let the fact that it's a real cock ruin it. It's going to happen. You begged for it. Remember?"

She stroked my face and cooed to me like I was a child in need of soothing. I was freaked, but her whispered reassurances were working. I stopped thrashing but was still completely tense; fighting with the contradiction of being raped by a guy and the endorphins flooding my brain.

"That's it sweetie", Danni continued. "You want this. You need this. You crave this." The emphasis on the word crave was nearly guttural. "You want to feel what it's like to be a woman. A big hard, fat, cock, driving into your sissy pussy. Fucking you. Breeding you. Raping your sissy cunt. Big and hot and hard as a rock. Rubbing your prostrate and bringing your sissygasm nearer and nearer. You feel it, right? You need it, right?, You CRAVE this!" she hissed into my ear.

It was working. My homophobia driven fear waned. I started to relax. Not really accepting that a man was fucking me, but accepting that I loved being fucked by a real cock.

Suddenly the cock was pulled completely out of my ass. The tip just touched my asshole. I lost it. I wailed in frustration and tried to buck my hips back. I needed that cock. I needed to be fucked. I needed to cum with that cock fucking the shit out of me. I was a cock whore and they were denying me my prize. I flailed my head about; trying to convey that I needed his cock back in my ass. I no longer cared that it was a real cock or that it was a dude. I was devastated and needed the fucking to continue.

I tried to look at Danni through the blindfolded. She seemed to sense I was looking for her and removed the blindfold. She gave me a shit eating grin.

"What's the matter Sissy? He stopped. Isn't that what you wanted? For the fucking to stop. I mean you don't want to be fucked by a man, do you?"

I blinked a few times. The cock rubbed up and down my crack a few times and caused me to moan involuntarily. I was on the edge of the abyss and she new it. She gave a nod to the person fucking me. He slipped his cock into my ass; a single long, deep stroke; and then slowly pulled out again.

My eyes rolled back and my neck arched up; as a guttural moan escaped from my throat. My pucker hole gaped and winked and begged for more. When I had come back down I looked at Danni pleadingly.

"If I take the gag out, will you behave? No shouting or freaking out. You don't talk until I give you permission."

I nodded enthusiastically. Danni beamed and removed the gag. I did as instructed and said nothing. She tossed the gag onto one of the side counters and looked back at me.

"So Sissy... here's the situation. You desperately need to get fucked. We can all see it. So you can either beg to be fucked again, or everything stops now." To reinforce her words, the cock made another full deep stroke into my ass pussy and pulled out.

"Oh fuck..." I moaned involuntarily.

"I did not give you permission to speak yet!", a strong hand cracked on my right ass cheek and I nearly yelled in pain. But some how I managed to hold my tongue.

"So here's what I need you to do. I need you to beg for that big hard cock, to fuck your stretched out sissy pussy. You can address the lovely man fucking your ass as 'Daddy' or 'Sir'. You will NOT address him as Master - I am the only one in charge here today. If he and I are both pleased by your begging, I'll let the fucking continue. If you fail... I haven't decided yet. Punishment; frustration; or perhaps both..."

I opened my mouth to start and then closed it again. She had not given me permission to speak. She smiled and nodded at me; then let out a small laugh. His cock continued to slide up and down my crack and prod my sissy hole.

"Very good Sissy. I did forget to give you permission to speak. You may beg now."

"Please Sir, fuck my sissy ass. Make me your sissy cum dumpster. Ram that huge magnificent cock deep in my pussy. Rape my sissy hole." I begged.

"Oh come on. You did better than that earlier.

His thumb started to press in and out of my asshole. Just enough to cause it to feel good, but not deep enough to give any penetration. He was really working me.

"Please fuck my cunt. Rape my hole. Make me your bitch! I need to be fucked! I'm desperate to feel your big hard cock deep in my pussy. Please Daddy; fuck my ass and breed me like a Sissy cum whore. Slap your big beautiful balls against my taint as you drive your fuck stick deep in my man cunt. Fuck me! Please god fuck my cunt!", and I started to try to buck back to get his thumb to pop into my pussy.

His thumb pulled away from my ass; as did his cock. He was no longer touching me at all. I looked at Danni in desperation, thinking I had failed. Danni was smiling, but not at me, she was looking past me. I had no idea what was going on.

"What are you?" Danni commanded.

"I'm a sissy whore."

"No," she countered quietly.

"I'm a cum slut."

"Uh uh."

"I'm a cock slut."

"Keep trying."

Oh fuck, I had to guess what she needed to hear. I thought back on all the things she had called me and things she had yet to say.

"I'm your Sissy slave."

"Oh I will have to remember that, but still not right."

"I'm a cum dump for cocks. A whore to be used!"

"I'm loving your attempts Sissy. So imaginative. Perhaps I should give you a hint, hmm? But, if I give you a hint, it'll cost you later."

"Please Mistress, please give me hint. I'll do anything."

"It starts with an 'F'," she provided in a singsong manner, clearly enjoying my desperation.

There it was - the dreaded 'F' word, that all heterosexual men fear for some reason. I didn't want to say it and she could tell.

"Is the little sissy afraid to say the word? You clearly enjoyed being ass fucked; begging for more like a bitch in heat; moaning like a whore; and nearly going crazy when the fucking stopped." She drummed her fingers on my cheek. "But if you want to pretend that this isn't you, well... I guess we'll just pack it up, and leave you to your machines."

She stood up and I panicked. She was gonna stop this. I couldn't let it happen.

"I'm a sissy faggot. I need to be fucked. Please Mistress." The words streamed from my mouth. "Daddy, please don't go, fuck my pussy. I need to feel your big cock deep in my cunt again. Please fuck me and cum in my sissy hole. Make me your bitch Daddy. I'm a faggot cum slut and need it desperately!"

I was swung my head from side to side, trying to see where Danni had gone. Danni slapped both her hands down on my ass, then pulled my cheeks apart. Then she did it again, three more times. The final time, just as my cheeks reached the zenith of the spread, Daddy's cock slammed home all the way to his balls in one single thrust. It was a master stroke and they had clearly planned it well.

It caught me completely off guard and it caused a fair bit of discomfort, bordering on pain, when he bottomed out.