When does sharing fantasies become topping from bottom

Although I have been reading BDSM-type stories for a long time, I am new to actually trying to live my fantasies. My master/lover is very experienced and very patient. My question, and I would love to hear from tops and bottoms (or whatever words you prefer for yourselves) is this: when does sharing fantasies become topping (or trying to) from bottom. He and I have a long distance relationship, so I have a lot of time to myself to imagine/fantasize/dream about what he/we will do next. He has already pushed my limits on pain--I took way more than I ever thought I could, without using, or needing, my safe words. But is telling him my full fantasy, from start to finish, too pushy?
I'm sure this has been discussed before, but I did not see this topic, and I haven't yet been able to read everything on the site. (I have a little one, so I can only hit this site when I am sure she won't be around. She's only 8----NOT involved in any way, except knowing Mom has a boyfriend, so please don't think I am trying to violate the age rules.)
Thank you to any who take the time to reply, as I can really use the advice.

Sharing your fantasies is a very important part of communicating both your desires as well as dislikes. Dislikes are not necessarily limits. Knowing what you don't like can be useful in pushing those limits and exploring things that may be exciting that you never expected. As far as topping from beneath, unless you are rigidly specific about following your fantasy; that is using it for a script to follow, I wouldn't consider it in that vein at all. Even then, following a script may be used as a reward or if your master enjoys it as well, be the basis of a play time. Fantasies are just that; and trying to create them in real life may be either disappointing or a tremendous thrill - for both of you. Demanding that he satisfy your fantasy might be construed as topping from the bottom; but sharing them....hardly.

Some fantasies are best kept as fantasies.

In some peoples opinion..."topping from the bottom" is just a bad face saving excuse of those who are perhaps not as dominant as they would like to think they were.

Timing is everything. Discussing your fantasy and your needs between active play sessions is not topping. Doing so during a play session, even one where your expectations were different and are not being met, is topping.

During play, unless demanded so by the dominant, the dominant expects to lead and expects you to follow, take it, suffer, and/or enjoy. If he demands you reveal all during a play session, then you aren't topping, you are submitting to his demands. Otherwise, discuss it later. Or reveal all during your journaling... he does make you journal for him? It's something I demand from my (once) online submissives as a way to know them better. In-the-flesh, it's not as important to me, I get to look in their eyes and their reactions.

No, he does not make me journal--we have a strange relationship: part him Dom, me sub, part vanilla, and part me trying (and failing so far) to top him. He may be afraid--my last letter was 11 sheets of looseleaf, filled front and back. We are not online-I commute from New England to FL (except when his job brought him up here to me,) so we do have face-to-face time. Just not enough--hence my backlog of fantasies. I never meant for this to be a BDSM relationship. Heck, I never meant to start a relationship; we are old friends, and his greeting used to be, "Want to sleep with me?" to which I always replied, "No." I had a boyfriend most of the time, and he was a friend who hated watching me with a (non-consensually) emotional abuser. But we got started, and now I can't tell him (my current) no. I just want to please him, whether as a bottom, a vanilla, or a top. Some of what he wants scares me, but when I think of it WITH him, it gets less scary. He was my true anal first (I tried before, but it didn't work.) He just makes everything so good that I am willing, even eager, to push my limits. He gave me my first real beating (for us, impact play with whatever toy, or just his hand) and, while it hurt, it was sublime pain. He has introduced me to so much, and taught me so much already, but calls what we do "slap and tickle." I want to learn enough to take it to the next level, which is why I was so excited to find this site. I have already learned a lot from the people-including getting an idea for topping him that I think I can do. Do Dom/mes ever have trouble hurting (in play) their subs? I love him so much that hurting him, even though he wants it, is hard. His ideas of being a bottom are so different from mine--that is where I failed at topping. I did what I would want, and pulled him completely out of sub space. I guess I would also ask for ideas for pulling his fantasies from him.
I know I am asking a lot of the people on this list, but you all seem so, well, not nice, but willing to help someone who sincerely wants to learn, that I feel comfortable asking you all for help. Sorry if I am asking too much, and thank you for everything you are willing to share.
So here is a question that might deserve its own thread: can a true sub learn to top well? If so, do you have any suggestions regarding sources?
Thanks again, all of you, whether you respond here or not. I am trying to work my way through all of the forums, but it is taking a while. But I am learning a lot. I have joined the Tasking group, as a Taskee-Would joining the Tasker thread help me?
Special thanks to Ozme-do you think started a journal on my own might help?

Yes. Even if only for yourself, writing makes you organize your thoughts... helps you find yourself.

Thanks--I know it helps me with lots of things. (And you may have noticed I have Stephen King-itis, also known as diarrhea of the mouth/word processor!)

Can/would anyone share what sorts of things might be in this type of journal in particular?

I don't really have a journal, but my Master wanted me to write fantasies for him, so I have a little book of them. Sometimes I write things that I like, sometimes things that I think he would like, and sometimes they are the same things because there is a lot of overlap. Some types of things I write: describing actual sessions that we've already done together and really liked, pure fantasy set in another world with other rules, fictional scenes set in our society, or describing a session between us that I'd like to try (those are the hardest).

Last night he held up the little notebook and said it was the best book he ever bought, which was amazing to me and felt so good. I'm not a great writer, or a professional writer. It's even harder for me to tell fantasies out loud than to write them, but he always wants me to do that too. I'm easily embarrassed by some of my fantasies. I'm even more embarrassed that one time I got so disgusted I ripped out half the pages from the journal and threw them out. Boy was he mad. I won't do that again no matter how lousy the story seems later on.

Most of my fantasies are things I wouldn't really want to do.

So many good points were made so I'm just going to agree and repeat lol

I would communicate all fantasies in between sessions. I would never do it during a session. Sometimes by expressing what you'd like to try before hand allows your Dom to add his own little twists to it to where it is fulfilling for both people involved. And as said above, some fantasies are just left best at being a fantasy.

Communication is the most important factor in any relationship. Be it friendship, vanilla marriage, or hard core BDSM. Do not be afraid to say something. A good partner will respect what you have to say and, whether good or bad, will support you through it. Just be sure to show the same respet and understanding in return. ny fantasy worth playing out is worth talking about.

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Originally Posted by Dog's Lady

Thanks--I know it helps me with lots of things. (And you may have noticed I have Stephen King-itis, also known as diarrhea of the mouth/word processor!)

Can/would anyone share what sorts of things might be in this type of journal in particular?

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Once I had a Dom who wanted me to write 'reports' (he had a military background) after sessions. It worked for us both.

I know I haven't been on much lately--I was stuck without internet for a while. Thanks for all your responses; they have (at least) given me food for thought. Look for my new thread on training--I look forward to your responses there, too.