Per the request of my MISTRESS, i am posting my first anal experience. Last night, my MISTRESS and i arrived at HER apartment and SHE proceeded to get me drunk while we watched a movie, and SHE playfully licked and grabbed my cock occasionally. i didn't know exactly why, but i knew that SHE only fed me copious amounts of alcohol when SHE had devious sexual schemes in HER head. After a couple beers and the majority of two bottles of wine, SHE took me into HER bedroom. i laid on my back and SHE spread my legs wide open. SHE then placed a vibrator between my balls and asshole and asked me how it felt. "Good", i honestly replied. The next thing i knew, my ass got cold with lube and i knew something was going in there. As previously mentioned, i had a bit of alcohol, so the timeline from here on out somewhat escapes me. What i do remember is my MISTRESS putting a finger in my ass and gently massaging it to get me warmed up for the toys SHE had. It felt incredible and i didn't want HER to stop. SHE made sure to always ask if i was feeling okay, or if it was too much. W/we have talked about anal play before, and i knew it was something SHE had planned on starting me in. i wasn't expecting it to be last night! However, once i knew what HER intentions were, it took me no time at all to be very aroused and excited at the prospect of trying something new. i didn't know quite what to expect, but i do trust my MISTRESS wholeheartedly, so with that undercurrent, i knew (as i always do) that anything SHE did would feel good and only serve to propel O/our sexual relationship. SHE flipped me on my stomach and inserted a "small" buttplug into me, which felt enormous. i remember thinking it was both painful and extremely pleasurable at once. My ass felt hot when SHE pushed and pulled on the plug inside of me. Eventually my MISTRESS worked the entire plug into my ass and asked me to keep it there. Much to HER dismay, i repeatedly pushed it out after just a few seconds. i wanted to keep it in, and i was trying to keep it in, but i have never trained those muscles and i just didn't know how to keep the plug in place. Next, SHE moved onto petite anal beads. Those were fantastic. There were five beads in all, and SHE slowly inserted them into my tight asshole one by one. At one point, SHE told me i was a good boy for having all five beads in me at once. i am HER puppy and that sparked in me the desire to pant for HER and lap at HER pussy. i couldn't, however, because of my position on my stomach, but mentally that's all i could think about. SHE eventually used a vibrator in my ass, which was quite an experience. SHE used two settings; the first setting felt stimulating and erotic, but the second was a bit too much. i immediately gasped in pain when SHE turned it on, but before i could even let my MISTRESS know how badly it hurt, SHE had stopped. The only other time i had an uncomfortable amount of pain all night was when SHE attempted to put the level 2 buttplug all the way into my asshole, and i was nowhere near ready for that. Overall it was a wonderful experience. The entire night, my thoughts consisted of two primary things. my first and most prevalent thought was "this ass belongs to my MISTRESS, and this will help train me to give HER more pleasure." My other, more selfish thought, was that "This will train me to experience my own pleasure in new ways." The entire night flip-flopped between pain and ecstasy, with a very blurred line in between. My little ass is sore today, but it feels sensual and keeps me aroused because i know its from my MISTRESS dominating and invading me. W/we start officially anal training tonight.