I couldn’t help myself…

W has presented me with a list of “preparations” he would like me to make in advance of our upcoming trip to NYC:

I think it’s fair to say that while we are in New York I will want you to have your holes filled and cunt lips stretched as we enjoy the city.  Therefore you should start conditioning your holes and lips now.  Every day something should be conditioned, though it need not be continual.  Starting today, a goal (conditioned by safety and practicality) should be to have either a cunt insertion (dildo, chime ball, etc); a butt plug; or a ring attachment (weight, ribbon, puller) in place at some point every day. These conditioning tasks would optimally be in place while you are out of the house.

Provide me with regular reports.

I wore bells Saturday night as my first execution of his instructions. That turned out swimmingly, for him, for me, and for Ad.  Hopefully I’ll post my notes about that night soon.
Today I wore a buttplug. My missive to him:

Glass buttplug in.  Pussy wet.  God, I’m easy.

An update on Fetlife, later:

“Preparations” update: Plug out. Time worn: 4 hrs. My bum is tender! Glass plug definitely harder to keep in than the Njoy when moving around, tho it didn’t almost fall out. This time.

“This time” was in reference to the last time I wore it, and yes, it fell out: That sound you heard…
I also said, in email:

I wish you were here and I could go over to your house at lunch and get my ass fucked by you.  Seeing as it’s all open and ready. Damn.

His response:

Excellent job today. The plug has performed its function.  I want you prepared and receptive to an ass fucking at any time. Wear an ass plug again tomorrow and consider that I may direct other cocks to perform the ass fucking. Observe men around you tomorrow and speculate as to whether I would select them to ass fuck you. Report to me on three such speculations.

I’ll tell you, that was all it took. If I wasn’t a wet, quivery, horny mess already (and I was), that note made me one.
Yes, I am easy.
And I had to assuage that “itch.”
First, the funny part.
A while back, while W was out of town the first time this past month, Ad and I had a date night. I was dying for an ass-fuck. Every once in awhile, I just need it/want it/gotta have it. I’m lucky (depending on how you look at it): I have two men that like to use my ass in two completely different ways.
Ad loves to fuck my ass, but he is rather well-endowed, and frankly I can’t take it often, at least not comfortably. For that reason, he enjoys fucking my ass best when I am drunk, or does it gently, prepping me considerably, with fingers and lots of lube and pushing in slowly, allowing me to relax and open up to him, before fucking me hard.  (And even then sometimes I can’t handle it for long.) If properly prepped, though, it is actually an orgasmic experience, and one I quite enjoy on a physical level.
W is thick, but not as long, and actually is much more pleasurable in terms of how his cock feels in my ass. But he seldom (if ever) “preps” me the way Ad does, and I can count the times he’s used lube to fuck my ass on one hand–and that usually only my own spit or cunt-juice.  His ass fucking is more about brutality and dominance.  And, as such, turns me on wildly, so that even though it hurts, I usually orgasm from it (even as I am whimpering and trying to escape.)
That night, the date night with Ad, I wanted to other kind. I wanted to be filled, but not brutalized, I wanted to be stretched, but not ripped open, I wanted an ass-fucking that was about me.
So I prepped myself by wearing my Njoy buttplug out to dinner and by having several drinks (liquid courage) so that I could get up the nerve to ask for it. Also, as noted, there’s something that appeals to Ad mentally about fucking my ass when I’m drunk, so I figured that couldn’t hurt.
Unfortunately, because I had W on my mind as well, I decided to use the Njoy the way I imagined W would like best: with no lube.
(An aside:  as I write this I can imagine W reading it and shaking his head: “This is why I don’t let submissives hurt themselves!”  Also, I have to confess to the rest of his “Preparations” instructions, above: “If you have any questions regarding what is safe, ask me or Ad. The applications need not be all day or even very long. DON’T HURT YOURSELF, or be overly ambitious.” He wrote that before he knew about this story, so I am sure he will be shaking his head at me.  Because yeah–he does need to tell me that. LOL)
Anyway, I tried to shove it in dry, but just could not get it to go.  So, feeling like a wimp (and I know that it’s not wimpy to use lube, that was just where my head was at), I wet it with my tongue and bent over in a stall in the women’s room at the restaurant (while a woman texted on her phone in a chair just on the other side of the stall door) and shoved and twisted and pushed until I shoved that fucker in.
I am certain she could hear my stifled gasps and moans and whimpers as I did so.
Insertion accomplished.  I wore it for the rest of that night, until we got ready for bed, when I removed it. I had mentioned it to Ad, and he had grinned, but although we had some fantabulous sex, we never actually got around to the buttsex.
And I wasn’t sorry one bit that we didn’t. See, when I pulled that damn plug out, my ass was sore. I couldn’t believe how sore it was!  I would never have turned him down to fuck my ass if he’d wanted, and in fact, if it had been a W-scene it would have been hot as hell for him to take my ass, brutally, as raw and sore as it was. But, as I mentioned, that’s not Ad’s style, and if it had been, it probably would have killed me. So…I did my best to make sure Ad was totally satisfied without going anywhere near my ass. LOL
It was only two days later, when my ass was no longer tender, that I told Ad how glad I was that we hadn’t had anal sex, about how I’d used the Njoy, and how sore I’d been.
He laughed and gave me the line about “submissives hurting themselves.” Oh, he also might have said, “Did you tell W?” because he’s sweet that way. Wants to make sure that W always knows when I’ve gone and done silly things.  I may mumbled something that sounded affirmative, but actually wasn’t.
It’s been long enough now that I figure I can tell W.  Also, I have an even better story to tell now.
So I told ya’ll about how worked up I got wearing the plug, etc. I was obedient, not hurting myself, using a bit of lube (but not enough to shoot the damn thing out of my ass) and not wearing it for too long.
But goddamn I was worked up. After I took it out, my ass was just so…open. Waiting to be filled. I wanted to be fucked so bad.
I knew I couldn’t have that (at least not immediately) but…I could have an orgasm. But I wanted more than a quick fingering in the car someplace. (Besides, it wasn’t dark, and it wasn’t raining–hard to do it in the car without creating a spectacle under those circumstances.) And…I wanted something in my ass. And my cunt.  And lucky me, I knew just where I could have all three things: W’s house!
At lunch I drove to W’s, ran upstairs, got out the Hitachi and the glass buttplug and then searched around for a suitable cock-replacement. And found one.

Yeah, yeah, I could have chosen any number of toys that wouldn’t have been quite so…filling. That might have fit more easily and been more comfortable. But damn it, this was W’s house, I had to do it his way, which meant a large, not “nice” fuck toy, and no lube.  Even the way I used the Hitachi was the way he would have used it:  when I realized it was going to be a painful fuck, I didn’t stop.
And ohmygod was it a painful fuck. I was wet enough in the cunt for the toy to push in pretty easily, but even after having worn the plug for 4 hours (or maybe because of it) my ass was soooo tender when I shoved the plug back in!  But I persevered. I was desperate for an orgasm, and the pain was only making me hotter and wetter, and the thought of W, imagining him there, doing these things to me (or making me do them to myself) was making me crazy.
And god was I tight!  Wow…I’ve done DP with the guys, but those times I’ve been pretty liquored up, which always relaxes me down there, and besides which, bio-cocks are malleable, to a degree. These were hard and unforgiving and I could feel them both inside me, filling me and stretching me and pushing against each other. And when I came…I nearly screamed, the pleasure and pain was so intense, as my muscles bore down on both toys at once.  And it all happened within about ten minutes of walking in his back door, because I had to be back to my office in an hour.
“I just couldn’t help myself,” will be my excuse, when he shakes his head and says that’s why he doesn’t allow submissives to hurt themselves.