Sissy Step Dad Ch 01

Story contains Femdom, Pegging and forced MM sex. If this is not your thing, please don't read it. This is my first submission so please don't be too harsh - but comments and suggestions are welcome.

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It started like most of our special Saturdays. This time, I was the one locked to a padded A-frame in our basement playroom. My ensemble consisted of black Cuban heel stockings and matching garter belt; a lovely pair of slut red 'please fuck me' strappy heels; a 3 inch penis gag locked in my mouth; and a VR headset looping through a playlist of my favorite porn clips.

I couldn't see or hear anything going on in the playroom - or the rest of the house for that matter - because of the VR headset I was wearing. My ass was slowly being fucked by a small realistic 6 inch dildo attached to our fucking machine. A dish soap bottle filled with lube was supported over my ass and dripped lube in my crack about once per minute; allowing me to be fucked for a long time without injury.

How did I get in this position? Well, after a few years of tinkering; a lot of time; and a fair bit of money; I'm able to get into this position all on my own. I own a company that builds electro-mechanical control systems, I'm also the chief designer and engineer, so it wasn't hard, it was just time consuming. Originally, the submissive person would have to be strapped in by the Dom. That took some of the surprise out of play time. Now, either my wife or I can strap ourselves in, then wait while the anticipation builds. Being able to lock ourselves in self bondage adds an extra layer to fun time. And we've accumulated a large assortment of toys, bondage gear, and homemade machines to further enhance our fun.

So, I cleaned my bowels; shaved my ass, cock and balls; and strapped myself in. Because I was feeling adventurous, I laid out my favorite paddle and flogger. I wanted Laura, my wife, to know I was in the mood for some discipline.

Laura, went out before I got out of bed. We had made plans for the day when we went to bed. She didn't tell me where she was going or how long she would be gone. That's what makes it so fun. She's getting really good at mixing it up. She has shown up anywhere from ten minutes to two hours after I've strapped myself down. Some days she'll leave me strapped to the system and use me two or three times before she releases me. She's also teased that she's might pimp me out to her girlfriends; and that she might have already let one of them fuck me. But I don't think she has. She always seems a bit reserved when sex talk comes up around other people.

I was strapped in for about 20 minutes, based on the clips that have played, and the fucking machine was working it's magic. I was getting into a rather spicy clip - a shemale stroking her huge cock, telling how she's gonna use it on me - when the fucking machine shuts off. FUCK! Goddamn random setting. This elicited a moan of frustration from me, and a fair amount of drool being released around the penis gag in my mouth. I felt a fingernail traced up my back, which scared the hell out of me initially, and then caused me to shiver. Here we go, I thought.

The VR headset effectively made me blind and deaf, which kept me on edge. Laura made me wait. No contact, just the VR input. My mind played out previous sessions; trying to deduce her plan. Would she take control of the fucking machine and use it to rape my ass?. Would she pull it out and beat my ass with the flogger or paddle? Would she remove the gag and skull fuck me? Or would she use one of her many strap-ons, to fuck the shit out of me? Maybe, she'd make me eat her pussy until she screamed. I love it when she does that. But that's a rare occurrence, since it requires her to remove the VR headset (for her comfort - not mine).

The wait was becoming unbearable. The VR clip changed, and the fucking machine started again. Suddenly the paddle struck my ass, which caused me to jump. Luckily the straps kept me from moving and dislodging the dildo. Laura must have moved the automatic lube bottle to be able to hit my ass where she did. This is something new, and new is almost always good. With the dildo buried in my ass, the paddle strike caused my cheeks to pinch around the dildo. It was a little uncomfortable, but exciting.

Another whack with the paddle; this one much harder. I yelped into the gag. The paddle rained down on my ass; she was really laying into me. She hadn't beat my ass like that since I forgot a promise to clean out the garage. I wondered what I had done. My ass was burning, but I've gotten used to spankings, so I was able to tolerate it without crying. I was however, screaming into the gag as each stroke landed. I was also drooling like a Bulldog.

The spanking stopped. My ass was on fire. The lube was not returned, but the fucking machine continued to pound my ass. I was beginning to worry; was this one of Laura's friends? Someone that didn't know how to play safely with our toys; or was she messing with my head? No, Laura wouldn't have allowed someone to play with me without supervising. And she would probably have been masturbating furiously as she watched. That thought spurred my excitement.

The VR headset played another couple clips with no further contact. She was really getting me frustrated with all the waiting. I could tell the lube was becoming less effective, and I started to struggle, hoping I could get her attention.

The fucking machine was suddenly pulled from my ass without being stopped. It stabbed my balls on the way out which made me groan in pain. Hands touched my ass and spread my cheeks. My pucker hole was not really gaping, as the dildo was pretty small, but the stimulation to my ass was still welcome. I shivered in anticipation.

A large amount of lube was dropped on ass and spread around my cheeks and into my crack. I felt a finger pressed against my hole; it slipped in and started to fuck me. After the dildo, Laura's finger seemed pretty small, and a bit unsatisfying. But her knuckles were bumping my perineum, which felt really nice. A second finger was added and the fucking continued. I started to get into it and tried like hell to fuck back. Unfortunately, I was strapped down tight and couldn't move; shit! A third finger was added and I started to moan like the anal slut that I've become.

Her fourth finger penetrated my ass easily and she used all four to fuck me for a while. I was waiting impatiently for her to fist me, but instead, she stopped and pulled her fingers out. Noooooo! My ass was empty and gaping. I needed to be fucked, but I was tied down and gagged. I screamed "Fuck Me" into the gag, but all that came out was incoherent sound. (Penis gags work so much better than ball gags - if you can get use to them.)

Again all contact stopped. I was alone with my thoughts and the video clips. My cock was dripping and pulsing. My asshole was winking; waiting for the penetration it so desperately craved. I tried too buck my hips again. Hoping of provide some stimulation to my cock by rubbing against the bench. but I was too well secured. I wailed into the gag in frustration.

I felt a heavy weight drop across the width of my ass; it felt cold. I wondered what the hell it was. Had Laura bought a new toy? I felt her pour lube all over the object as it laid across my ass, clearly making a huge mess. Then she lifted it; and let it drop into the crack of my ass. With all the lube coating the object and my ass, it made a sound like a fish dropped on a table; and it stung a little as it hit. Slowly, deliberately, she started to rub it up and down the length of my crack.

It was huge and seemed solid. There didn't seem to be the normal flex you feel in a large dildo. She moved the end down to my asshole. She changed the angle and applied pressure. The end felt somewhat flat and I knew this was not going be an easy entry. What the hell was it?

She began to rotate the upper end of the object in a circular manner. This caused the edges to start to slip into my pucker hole. The edges were rounded, but the bottom was flat. I was thinking maybe a wine or pop bottle. She continued teasing my sphincter to open. Urging the monster to invade my ass. My outer sphincter ring surrendered, and the brute slip started to slip in. But because it was flat, it stopped at my inner sphincter muscle, and I grunted.

Laura seemed to know that this was a real stretch and was taking it slow. Thank god! She started to thrust the object lightly but rapidly against my inner ring. She prodded my inner sphincter muscle; insistently; unrelentingly. Bump, bump, bump. Over and over again. Trying to loosen me up. Urging the the invader to enter my ass.

Suddenly, she pulled it out. My ass clamped shut and I screamed into the gag. It stung, but only a little bit. The scream was more of a reflex - like when you bump something and say ouch. She placed a hand on my back and rubbed soothingly. I sighed. It was ramping up to be a fun day.

The process of entry started again with more lube. The end of the new toy bumped my inner sphincter again. Faster and with more force. I moaned in pleasure and frustration, and tried to buck my hips back into the monster. Fucking bondage straps! I needed it in me! She placed her hand on my back again, which caused me to relax. As I relaxed, she pushed hard, and the monster slipped past my inner ring. It felt like someone shoved a bowling ball up my ass. I screamed into the gag and shook my head. It hurt! Fuck it hurt. I needed her to take it out.

All movement stopped. Her hand was still on my back, rubbing in small circles. I eventually calmed down and started to breathe again, as the pain became tolerable. The invader started to move forward and back and then side to side; like the stick-shift of a car. The movement repeated to loosen and stretch me. I felt my sphincter loosen and pain begin to subside.

Huge amounts of lube were poured down the toy and pooled around my asshole. So much of it that it ran down over my balls and onto my now flaccid cock. The circular motion started again and it caused the toy to hit my prostrate once per circle. The feeling was intense. My limp cock started to leak as I was milked; and I moaned in delight.

Again, all motion stopped. I waited patiently for Laura to fuck me. The minutes ticked by. I noticed that the VR clip changed (I swear to god I forgot I had been watching it). The monster started to rotate like a drill. First left, then right. Back and forth. Only a little bit at first, but then more and more. I realized she's working the lube into my ass to prevent the toy, or whatever it was, from sticking to my inner ass membrane. God I loved her.

Laura started to add thrusting to the twisting motion. Bit by bit, the toy moved deeper into my ass. Six inches deep and she showed no signs of stopping. Deeper and deeper she kept thrusting and twisting into my ass. The angle of the toy being changed as it meets resistance or I showed discomfort. I was drooling and moaning around the cock gag. The intensity of this new toy was like nothing I had ever experienced before. It was bigger than Laura's fist and it was absolutely solid; no give at all. I felt every movement through my sphincter and prostrate. Pure heaven.

It hit the end of my rectum, which caused me to grunt in discomfort and arch my shoulders and head up. She stopped and slowly pulled it out about 2 inches. She must have had nine or ten inches of the monster up my ass; I couldn't believe it. I felt her lay something on my ass and wrap it around the object. I had no idea what it was or what she was doing. Suddenly, she pulled the toy out rapidly, and left just enough inside so my sphincter didn't close and force it out. It was one of the most intense sensations I've ever experienced through my ass. It felt like the toy was trying to suck my guts out with it. I howled in discomfort and a little bit of pain. Laura noticed and slowly pushed the dildo back into my ass. She continued to push until whatever she had wrapped around it, was pressing against my cheeks again. This, of course, elicited a moan of pure pleasure and caused my body to shudder. Slowly, she started to fuck me.

My ass became accustomed to the monster, and the speed picked up. Faster and harder. The wrap around the invader bumped my ass on each inward thrust. It prevented her from going too deep and hitting the end of my anal cavity. But more than that, it added to the sensation. Like when her hips bump my ass during pegging. Not something you normally feel with a toy; it was new; it was good. Really good!

She had never hammered my ass like this before. I was loving it. Suddenly, the paddle started to rain down on my ass cheeks. First one cheek, then the other. In time with the fucking. Thrust, smack. Thrust, smack. Not too hard; not too soft; the Goldilocks zone. Over and over. Trust, smack, it continued.

The assault overloaded my brain and I start to cum! My guts clenched and my ass tried to eject that magnificent toy. Oh my god, it felt like the end of my dick was connected directly to my ass. I squirted every time the toy was rammed back into my ass and cried out in ecstasy and discomfort. Eventually, there was nothing left to come out of my dick, my balls were empty. But the sensation continued. My ass spasmed and continued to try to push out the invader; and my dick spasmed in orgasm, over and over again. It went on forever. I screamed into the gag in pleasure, pain, and pure sexual overload.

The fucking stopped. Apparently the spanking had stopped too, but don't know when. My ass continued to spasm and I continued to orgasm. I eventually came down and started to relax and breath normally. My ass cheeks were raw and on fire from the paddle. The toy was still buried in my ass and every movement of it was fantastic agony. It was like it had attached to my nerve endings and any movement plucked the nerves like guitar strings. Nothing had touched my dick, but I had just had the most intense orgasm of my life. My ass and cock were still contracting as a single unit.

Her hand touched my back and I flinched. She rubbed reassuringly and glided her hand down to my ass cheeks. I stopped breathing, expecting more spanking. But her hand just slowly rubbed my cheeks, like she was admiring her work. Her hand lifted and I held my breath, waiting for the paddle. Nothing happened. I'm was in sensory overload, with no sensory input, except the damn VR.

She twisted the toy, slowly, about a quarter turn. My brain nearly exploded and I thought I might pass out. I screamed in rapture and anguish and my ass gave a mighty push to force out the attacker. The toy was yanked from my spasming ass; in concert with my push. My asshole closed a bit, but then opened again; gaping; flexing. It called out for it's lost lover. Begging it to come back and invade once again.

A finger ran around the inside of my gape and it winked a bit, but stayed open. I could actually feel my ass gaping, and air invade my anal cavity. Her finger continued to circle my gape lightly. A hand slapped my ass cheek sharply, which caused my gape to slam shut on her finger. She pulled her finger from my ass. God I would loved to have seen that, I thought, as I relaxed a bit.

After a few minutes, I felt a small dildo pressed between my ass cheeks and into my stretched out hole. Lube was still running out of my ass, so it slipped in easily. The dildo started moving in and out rhythmically and thought I recognized the fucking machine motion. A drop of lube hit my ass and I knew I was back on the fucking machine.

I waited patiently for more - but Laura seemed to be done with me. Minutes went by and there was no further contact. The fucking machine random cycle was in action and I figured I was alone again. It was a hell of a first session for the day and I wondered what she had in store for me next...

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It had been close to 2 hrs since Laura left (based on how many times the VR clips had looped). The fucking machine stopped and was pulled from my ass. I tensed, expecting more paddling or flogging. Instead, the VR headset was lifted from my head. Laura squatted down so she could see my face, her look ominous. "We need to talk." She didn't undo the gag, or any of my restraints. Seemed she was gonna do the talking and I was gonna listen; not good.

"Either you didn't read my note on the Fridge this morning, or you wanted to get caught like this," she was definitely displeased and watching my face closely. "Okay, your eyebrows indicate you didn't read the note; which is a damn good thing. But it doesn't change things you dumb shit. Because you were caught; you were used; and, you stupid fuck, you were FILMED!" The last word nearly screamed.

My mind was shattered. Was she fucking with me? Had I really been caught? Who the fuck had been in the room with me? Filmed? Holy Shit! I was freaking out and struggling to get loose. I wanted to talk; to find out what the hell was going on.

Laura stood up and moved out of sight. "I left you a note on the fridge this morning. It said that Danni was coming over. That she wanted your help to design some shelves for her apartment."

Oh my fucking god! Danni! Laura's 28 year old daughter. She's the one that fucked my ass and filmed me. I started to hyperventilate and struggle violently to get loose.

"I expected that you'd at least get a coffee this MORNING," she cracked the paddle on my ass viciously, and raised her voice on the word 'morning'. "But NO," another wack of the paddle when she said the word 'no'. "You're such huge anal SLUT, that you didn't even go in the KITCHEN before you came down HERE and RAMMED a COCK up your ASS!"

The paddle landed on my ass every time she raised her voice. The force made me scream into the gag, and forget that I had been caught momentarily. "I knew you were becoming a real anal WHORE, but I didn't think it was this BAD." Beating me twice more, then she paused, composing herself I suppose. "I just spent over an hour listening to my daughter's plans for your 'sissy ass'- as she so succinctly put it. And let me tell you, you're NOT going to like IT!" The paddle landed twice more.

"Or perhaps, as she suspects, you will like it. But that's pretty much irrelevant at this point. You either accept what's coming, or you say no, in which case the video gets posted all over the internet". She was clearly exasperated, and pissed, and distressed.

I was lying still; I had pretty much gone numb. Not just from the beating, but from the humiliation of the whole situation. What the fuck had I done? How was I ever gonna face Danni again? What the fuck did she mean by 'plans for my sissy ass'? I wanted desperately for Laura to release me so we could talk about this, but I was still gagged and she didn't seem in the mood. The force and anger behind the beating of my ass made that clear.

The paddle crashed into the wall behind the counter. Laura was clearly trying to vent her rage. Her legs came back into view. She was standing to avoid the puddle of drool, tears and snot that had accumulated on the floor below my head. She squatted again, and lifted my head by the gag strap, careful to avoid the drool. She waited until I opened my eyes and looked at her. "You stupid fuck," she whispered, shaking her head, sad and distressed more than angry. "You have no idea the shit storm you've unleashed."

I pleaded with my eyes for release. Which seemed to work, as she began to removed the gag.

Once the gag was removed, I began talking, trying to fix this nightmare. Or to at least stop Danni from releasing the film. "Laura," I pleaded, "even if there is a film, it can't be used to identify me. Danni never took off the head set or took out my gag. My face would have been hidden the entire time. And," I continued, "there are laws preventing the disclosure of harmful sex videos. Danni's a security consultant and knows that."