Anal Etiquette Ch. 00: Politics as Usual

Both Bill and I were rock hard but the size of Bill's cock made me almost feel sorry for Ashley – hell, it almost made me feel sorry for Ashley's mother! It was easily the length of her forearm and bigger around than it. It was hands down the biggest cock I've seen in person! While I wasn't as impressively gifted as her father was, I still packed a respectable dick of my own.

Bill had grabbed a towel nearby and wiped down the couch with it before sitting down. Without words Ashley moved in front of where he was sitting and lowered herself onto his dick in a reverse cowgirl. Despite its size, she never seemed phased by it; but I was willing to bet that by this point these father-daughter training sessions were a regular occurrence.

Once situated on her dad's massive schlong, she leaned forward giving him access to her asshole. He wasted no time in slipping his hand into her loose nether hole. Neither one of them were moving very much – even when he managed to get his huge hand up to the wrist in her backside there was hardly any movement to be seen. I knew what was going on! This was one of my favorite positions and I was pleased that Ashley seemed well acquainted with it. Sure enough I could tell from Bill's forearm movements he had gripped his cock from inside his daughter's asshole and was jerking himself off. I stepped up to Ashley's head, she gave me a quick glance and then grabbed onto my cock, pumped it a few times then abruptly swallowed the whole thing down her throat without the slightest hint of a gag reflex.

I was expecting a slow buildup and getting deep-throated right out of the gate was nearly too much for me, but thankfully I was able to reign in my impending orgasm. We continued like this for several minutes. Bill started giving me pointers on the best way to face fuck her but I think he was just talking to make it seem as though this was a teaching moment.

"Okay, let's try something new. I want to cum before I show you how far along her anal training is and you probably feel the same, right?" Bill had started removing his hand from Ashley's blown out rectum.

"It couldn't hurt." I backed up a little removing my cock from Ashley's throat and mouth.

"Go sit down, Cy. Ashley, you get on top of him." I moved to the chair I had been in

when this whole thing started and took a seat. Ashley quickly joined me straddling my hips in a normal cowgirl, she reached down grabbed my cock and impaled herself. Her pussy was so hot it felt like an oven. She ground her hips on my pelvis for a bit as we sat face-to-face with one another. I grabbed her by the back of the head and she leaned in for a kiss, soon we were both making out and fucking; that's when I sensed another presence joining us.

Bill had moved in behind his daughter and used a hand to press her flat against my chest. I felt some pressure on my cock and Ashley – of whom I was beginning to realize didn't make a whole lot of noise during sex – had that scrunched up nose look again as her dad worked on what he was doing. Ashley let out a "oomph" and I felt Bill's cock slide into her pussy pressing against my own. Things got a whole lot tighter all of a sudden, and whereas before I was in no real danger of cumming, now I was being forced to concentrate.

Once Bill was situated with his cock comfortably buried alongside my own, I saw him grab a 3" or so butt plug and start working it into his daughter's open ass. Ashley was grunting heavily at this point but I could tell when the widest part had slipped in because she got a lot calmer and her pussy got even tighter. Now it seemed like any movement caressed every part of my cock. Bill started rhythmically pumping and I did as well – as best I could. Ashley started to get comfortable with the intruders packed inside her and she started making her grinding movements again.

This continued for about 10 minutes when suddenly Ashley seized up and I felt her pussy spasm so hard I thought I might pop out of it, this was followed by a great gush of wetness. Her pussy continued to spasm and that was too much for me. I fought it as best I could but I gave up at that point. I felt the orgasm hit me suddenly and a great glob of cum shot into her squirming snatch; followed by another, then another, then another. The whole time, Bill kept pumping away, as my softening cock started withdrawing from her pussy. He started cumming just as I exited.

Bill finished up and we all stood up – Ashley somewhat weak in the knees from her ordeal. A glob of white cum splattered on the floor as she stood and I could see the absolute mess we had made of her pussy. Cum was dripping out of her opening and had covered a large portion of her inner thighs. She squatted on the floor in front of me and cleaned off my cock with her mouth; and then did the same for her dad. I backed away for a moment to get a better look at her as her dad grabbed the towel from before and wiped down the chair we were just in. She noticed me watching her still squatting in the floor. She reached down with her left hand and popped it into her pussy, even with the plug still in her ass the motion seemed effortless. She pumped her fist in and out a few times then brought her hand to her mouth where she cleaned the whole thing of our combined juices.

Bill had gone into the kitchen and was returning with a retaining plug significantly larger than the one that had been extracted from Ashley's asshole. While the length appeared around the same the width was much larger. So much larger, that when Ashley saw what her dad was carrying she did a double take. She knew what was coming though and maneuvered herself back onto the couch. Laying on her back she pulled her legs back behind her head exposing her dripping snatch and plugged ass to us.

I reached down and grabbed on to the base of plug seated in Ashley's backside and gave it a good yank. It popped free with no effort and her asshole remained agape. I grabbed the bottle of lube and coated my right hand and a good part of my forearm. Bill had set the retaining plug next to his daughter on the couch and had taken a seat in the chair we had been using to fuck minutes before. I kneeled down to get better access to Ashley's holes and promptly inserted my fist into her ass. My hand slipped into her easily enough. After letting her adjust as much as she needed to, I made a fist inside of her and popped it out of her asshole, then quickly reinserted it. I continued this action a dozen or so times then stopped flattening my hand out on the reentry and just started working my balled fist into her back hole.

She grunted in discomfort at first but her hole adjusted quickly, and after another dozen or so insertions pulling my clinched fist out of her ass and then shoving it back in, I started the process of forcing a deeper insertion. I slowly started pushing inch by inch into her intestines, she groaned and started wiggling her ass towards me resulting in my arm sinking deeper into her depths. It wasn't long until I had made it almost to my elbow. At that point, her ass stopped wanting to open up for me and I gave a few final shoves just to be sure, something gave and my arm slipped in another two inches or so.

Ashley was grunting and straining at this point and the current situation had her making more noise then she had made during any of our previous activities. "I think that's as far as it'll go Cy." Ashley looked down at me from between her legs almost pleading. As it was, I pretty much agreed with her assessment; but gave another few hard pushes anyway just to be sure. Once satisfied, I started jackhammering her asshole with my arm – slowly at first but speeding up with each stroke. After what must've been ten minutes, my arm was sliding from wrist to elbow with minimal resistance from her overly stretched back hole. I'd let my closed fist nearly pop out of her anal ring before pushing my arm all the way back into her until my elbow meet her asshole, then the process would start over.

After I was satisfied with her progress I pulled my fist free and examined her gaping hole. Happy with the progress made, I grabbed onto the retaining plug lying beside her and worked it into her ass. I could see the bulge form in her abdomen as I forced the last couple inches of the plug into position. Once in, I had to slide it back and forth and move it around some to make sure it was seated properly. The whole process took maybe another 10 or 15 minutes. By that time my cock was hard again and after standing I took advantage of her position and sunk my cock into her sopping wet pussy. The retaining plug had made her pussy so tight I was barely able to squeeze myself into her; but once inside, any concerns I had had about the fit melted away as I started pumping her snatch.

Bill at this point had started getting dressed and said he was going back out to finish the yardwork. Both Ashley and I waved him off and he exited the front door. I returned to the task at hand. Paying attention to her nipple jewelry for the first time I could see it was a clamp similar to an alligator clip accompanied by small pins sticking into her areola to stabilize itself. I grabbed onto the piece and started jerking and twisting it. For the first time since we began, Ashley started making some real noise now; her quiet fuck moans were turning into loud screams. I continued the assault on her nipple reaching down with my other hand and twisting the bare nipple in between my fingers.

Ashley's pussy was getting slicker with the nipple torture she was enduring. As a result, I knew I wasn't going to last to much longer. I gave a few last quick pumps and started refilling her with my cum. I finished up and pulled out her sticky snatch and let her clean me off again. With that I started getting dressed as she sat up and started readjusting the massive plug now seated in her backside.

"I'll see you tomorrow, Ashley." I reached out gave her nipple one last twist and headed for the door.

She called after me "I'll be looking forward to it!" as I headed back outside. I didn't realize it at the time, but his was the beginning of what would turn out to be a lifetime commitment; or at least so far it has been.