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Anal Training Progress Report
Written by thepoolboy
Anal Training Progress Report

I was lucky enough to have a very sexy mistress begin training me in February. It took her a little while to decide exactly how she wanted to train me. I was trained to her liking in oral and personal service, CBT, NT and anally. This progress report focuses on her anal training program.

I have enjoyed anal play for many years, but it had been a long time since I experienced receiving any. In the past I was able to take something around 1.5" in diameter with some effort. I could never take muh more than one finger without getting worked up to it.

The first time she played with my ass she just flipped me over her lap on the bed and started fingering my ass first with one lubed finger, then she worked in a second after ten minutes. I moaned like a whore the entire time. I loved it. She did a great job hitting my prostate. She loved how she could make me moan so loudly and constantly just by fingering my ass. This is when she decided she really wanted to take control of my ass.

Shortly after that night she explained how she wanted to train my ass. I thanked her profusely. I confessed my desires to be her strap-on butt slut. She loved the idea of pounding my ass with a thick plastic cock strapped to her body. She's in very good shape so I knew she could probably work my ass with the strap-on for quite some time. I also confessed to her that I'd used my rather thick cock (a little under 2" thick) to take many girls in the ass and wondered what it would be like to be taken with a strap-on of the same size or a little bigger. She was eager to train me to take something "at least that big."

I quickly found myself buying some toys at her 'request.' I was instructed to buy a leather cock and ball harness, a 2" leather ball stretcher, the Tantus Ryder butt plug, the set of five plastic Anal Dilators (Rectal Dilator Kit). She bought a lockable leather collar and leash for me. I order all of these items from Extreme Restraints. I quickly found my ass filled with something on a regular basis. I was pretty much constantly wearing a pair of nipple clamps (I already owned them) and one of the leather toys around my cock and balls. In addition, she would _always_ make me wear my collar, when we played.

Many times she would have me stroke my cock while I viewed naked pictures of her sitting in my chair with the plug or a dilator in my ass. She never let me orgasm except in her presence, so I was terribly horny the entire time she was training me. I also had to lick up each and every drop of pre-cum that leaked from my slutty cock. Withe the amount of teasing and denial she did, this was a very large amount over the training period.

I would wear one of these for anywhere from 15 minutes starting out to around 4 hours on average when she was almost done training me at a specific size. I wore the Ryder plug to bed one night and slept fine with it stretching my ass. That was about 11.5 hours total. By that point I could slip the lubed Ryder (1.5" thick) or medium rectal dilator into my ass in under 5 seconds.

She trained my ass consistently for about 8 solid weeks, before her career began to interfere (hours & a relocation). At the end I picked another couple toys, the Tantus A-bomb and the Suction Cup Anal Initiation Kit (three suction cup dildos). I have not been able to get the A-bomb into my ass, but that was her objective for me so that she would know I could easily take a 2" thick strap-on dildo as rough as she wanted to give it. She knew I was an anal slut and used that knowledge to control me and push my limits regularly. At the end of each session, which was at least twice weekly I would provide her with a detailed training report via email.

Near the end of her training, I stuck the smallest of the suction cup dildos (1.5" x 5.5") on a chair and was able to ride it up and down from tip to base for 10 minutes. I moaned like a whore again the whole time. I wished I was riding her strap-on, while she pinched & clamped my nipples, stretched my balls and talked dirty to me about how I was her obedient slut.

I haven't progressed much beyond where I was, when she stopped providing me training assignments. I am proud to say I have not regressed either (so far). I'll summarize my current level of training. I can take a lubed 1.5" thick by 6" long object in about 5 seconds. I can take a 1.75" thick object with some effort, but I can only take about 4" of it today. If she hadn't stop training me, I think I would easily be taking on of the 2" thick toys with little effort.

Occasionally, I still practice a little self prescribed anal training. It's not the same as having my sexy domme assign it or do it herself. I would love to find another sexy domme to complete my anal & other training.
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