Anal Plugs, Pegging, and Historical Connections

Several years ago, my Mistress sent me a link to a bunny tail anal plug and told me I would be getting one for Christmas.  At this point we hadn't quite reached a full understanding on a fetish level.  Well, to put it more bluntly, she didn't quite understand the fetishes that would push me into the deepest realms of subspace and to my own credit, I was unable to adequately communicate just how and why I would respond in certain ways, partly because of shame and partly because it's somewhat complicated if someone hasn't fully grasped the idea of the mindfuck.

She had thought the bunny tail butt plug would go perfectly with my other outfits but I told her not to spend the money on it since I wouldn't wear it and referenced one of my hard limits which was nothing up my butt.  I have a past history of abuse from my childhood and when anything gets near my rectum I go into a state of extreme panic and usually start crying.  Basically, that kind of thing was off-limits.

As things have moved on since then we went through a stage of problems and in order to help rectify them I waived my no anal hard limit.  This led to a rather intimate and heavy emotional experience that left me in tears but at the same time it has pushed me to an even deeper state of subspace that I had not experienced before.  I knew that I wouldn't be able to respond in a rational manner when the moment arrived so we planned beforehand and devised a method of restraint that would prevent me from blocking her (wrists chained to the ankles and a spreader bar chaining the ankles together, everything secured by locks) and included a blindfold and a gag.  This held me face down in the butt up position.  We had agreed beforehand that she didn't have to stop no matter what I did unless she wanted to stop.

I was breathing heavily and my pulse was racing.  Immediately upon contact I began to cry.  I was writhing around, tugging against the chains and sobbing into a pillow.  A few minutes into it something odd happened.  I felt like I "left myself" and my mind just surrendered to the situation.  I had a bit of a flashback to a Greek history class I took back in college.  One day we covered the portrayal of anal sex between men and women (if you aren't familiar, there are lots and lots of paintings and pottery portraying women being penetrated anally, sometimes while being forced to perform fellatio at the same time).  The professor explained how this exemplified the status difference in Greece between men and women and how anal sex portrayed symbols of one-sided pleasure.  Basically, if a man fucked a woman up the ass it was to ensure that he received pleasure and she received none.  Strangely enough, it was this lesson that ended up showing up in my brain and this set on a big feeling...

I was being used... this was one-sided pleasure pointed in her favor.  I was her fuck-hole.  I plunged deeper into subspace full of a new type of shame and humiliation I wasn't accustomed to.  A deeper shame and humiliation aided in the fact that she had dressed me up to the gills before we started.  Around this time she noticed that I had a raging hard-on (I hadn't even been aware of that).  It was a bit of a shock because it was more intense than my usual erections, I thought the skin around my penis was going to burst.  She started giving me a reach-around and commented on it, making it fully aware in my mind and adding another dimension to the subspace.  Not only was I being used but my submissive self was enjoying being used so unilaterally.  While I hated the penetration, the experience itself had every nerve in my body firing and my brain was spinning out of control.

This was about 8 months ago when all of this happened and we have had several more intense experiences of this nature since then.

I guess what I'm getting at is that I've started to reconsider the idea of an anal plug.  I know anal plugs are used frequently when it comes to sissification.  From what I've gathered it gives a feeling of being "filled in" and forces the hips to sway in a more feminine motion while walking.  I don't really have any draw to that but the symbol of it all does "get me" in that way.  That way meaning that it keys on the Dominant/submissive inequality to a rather hefty extent.  The plug gives no directly pleasure to the Domme.  For the sub it delivers quite a bit of discomfort and humiliation.  For the Domme, I can then see only two reasons for doing it both revolving around the same scenario.
1.  She has him wear an anal plug for discomfort and to serve as either a punishment, for training purposes, and/or reminder of his status. 
2.  She has him wear an anal plug for discomfort and she takes pleasure in his discomfort (that requires no effort on her part to inflict). 

The odd thing for me is that both of these things appeal to some level of subspace for me but each caters to a different type of subspace.  This is where things get blurred for me... I hate the experience of it but I like the feelings it brings.  Such is the craziness of being a submissive male.

Pegging is something that sort of makes sense to me and sort of doesn't.  My Mistress has a strong fetish for pegging (which sometimes makes/made me wonder why she chose me even though I was forthright with my "no anal" hard limit).  Standard strap-ons don't make a lot of sense to me both in Lesbian and heterosexual Femdom sex.  Feeldoes, double-ended strap-ons, etc. do make sense to me.  In Lesbian sex, both parties receive pleasure, in Femdom sex, only the woman receives pleasure.  With a single-ended strap-on, unless the Domme has a direct fetish for pegging (or the side-effects on the sub emotionally from being pegged) these just don't make much sense to me.  The one-sided pleasure idea behind pegging tickles my submissive fancy but the actual act of being pegged isn't something I'm fond of.  I guess I just don't quite connect with a pegging fetish on its standard levels as I've met several women and men who get completely aroused by strap-on play.  I have used male strap-ons before during sex with my Mistresses and those did "do it" for me because it was also one-sided pleasure in her favor.

I guess my thoughts are just all over the place on this one.