Who ever thought I'd write a post on this topic? :(  The above image should give you a pretty good idea of how I feel about anal sex. Up until I met S, no man had gotten anywhere near that part of my body! Not with their cock, not with a toy, not even with their fingers! The minute anyone tried, I'd spin around and fix them with my best evil eye and icily inform them: "That attraction is closed for the season!" I guess there must have been something in my tone because no man ever questioned me on it or pushed their luck a second time!!!

And then along came S... whom I love. And adore. And very much want to please. S. who is my darling Dom and makes me feel wonderfully submissive. And what does S.'s number one desire just happen to be? You guessed it: Anal sex. Cryyyyyyyyyyyyyyyyyyyyyyyyy!!! S. and I discussed anal sex at great length at the start of our relationship. He expressed his deep desire to have anal sex. I expressed my equally deep desire NOT to have anal sex. So we were at a stalemate. Except, of course, for the teeny weeny little fact that he's the Dom and I'm not... So where does that leave me now? Smack in the middle of anal training...

When thinking of limits, anal comes extremely close to being a hard limit for me. It's something I have never in my life so much as considered doing. It is NOT something I have fantasized about, unlike spanking, paddling, whipping, bondage, etc. And I'm extremely squeamish so the entire thought of anything being in there grosses me out. And to top it all off, I have a fair amount of fear associated with worries of ripping, bleeding, damage, etc. So, I was very tempted to just shut the entire discussion of anal sex down completely by making it a hard limit and enjoying using my two other holes to please S. instead.

But what stopped me was the sheer excitement that was apparent when S. spoke of putting his cock inside me there. He said he had dreamed of doing so his entire life. He was practically panting just at the very idea. The thought of doing something that would please him so much excited me. Plus, to me, it was pretty much the ultimate act of submission because I honestly expect pain and discomfort and so it will be entirely about his pleasure, not mine. So how could I refuse to even consider it? I couldn't...

Also, by the time we discussed the topic in earnest, S. had already used the whip to establish his ownership of my ass completely and irrevocably. Prior to meeting him in person, he'd say "mine" when referring to my ass and I'd giggle and contradict him: "nooooo mine!!!" But a couple of evenings with him and the whip cured me of that forever. Now when he points to my ass and says "Mine!" I shut my mouth and nod in enthusiastic agreement. I did try to beg him to let me retain ownership of just 5 percent of it (I bet you can guess which 5%) but sadly for me that wasn't gonna happen.

At first, S. was gentle with me, probably sensing what a delicate topic it was for me, and didn't push me to do much. He told me that I could take my time and prepare for it. (I told him I liked the idea of a 5 year plan. But sadly he didn't go for that. Ah well, a girl can dream!) He had me use a toy from time to time to train myself back there but never for more than 20 minutes at a time, and after a few weeks he let it slide altogether. He used his fingers when we were together and put toys inside me twice. If I hadn't been securely tied down the first time, I absolutely would have bolted right off the bed. But by and large, I thought I might be getting away with indefinitely postponing the whole anal thing and I was very pleased by it.

However, as Christmas approaches, and so does his trip to come see me, it appears that S. has decided that I'll be giving him a gift of anal sex for the holidays. Personally I'd rather sell everything I own and buy him a new car, but once again we run into that little issue of him being the Dom so I don't always get what I want, do I? Bleh...
So, last week, S. texted me that I was to start using the anal beads for 2 hours each day Monday through Friday, and the larger plug for an hour each on Saturday and Sunday. The second week, it increases to 3 hours a day, the third to 4 hours, the next to 5, and I'll be at 6 hours a day with the beads deep in my ass by the time he comes. Now the anal beads may not seem like much because they aren't terribly wide but they are terribly LONG. And let me tell you after my first week of experience with them, when you sit on them, it's like they are impaling you! By the end of 90 minutes, my ass was aching! I'm definitely not looking forward to increasing to 3 hours tomorrow! :(
When I typed back a response of sheer horror at this anal training plan, S seemed to find my discomfort greatly amusing. His last text on the matter said: “I’m not taking it easy on you. when I have you tied up and your legs spread far apart by the spreader bar, I’m going to penetrate your ass with my entire cock. You’ll have to feel how wide I am soon. If you aren’t prepared in 5 weeks, I will have no sympathy for you as my cock opens your ass for my shaft to drill.”

Is this the part where I run away and hide under the bed?