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Hi Guys! I've been looking some more through the site and found someone's post that recommended some hole training. Goal is to have something in there every day. I've modified it for my situation of not getting fucked much. The idea is kinda like working out, you might have chest day, rest day, legs day, rest day, back day, rest day, rest day. So, if my goals are width, depth, duration, and puffy lips, then I need to have days where I focus on those. Ergo, I'm dividing my 7-day week into: Stretch Day, Depth Day, Rest, Grip Day, Rest, Piston Day, Rest. What do those mean? Stretch Day: Goal is to stretch my hole across, get it used to being open wide. To do that, my target is to train with dildos and/or plugs, where I should be able to sit on the dildo or walk around with the plug for some period of time, at least 5–10 minutes. If I can do it longer, maybe it's time to size up. I want my lips trained to welcome in those larger-across objects. The goal isn't pain, but if there's some stretching pain that then feels okay after some poppers, then we're good. This should be progressive, at least 3 sizes each night, starting small and getting larger. Each size should be in for at least 10 minutes. If it slips out because my hole's too loose, size up and add remaining time to that object's time. At the end of the training, which should go for at least 30 minutes, if it's a plug and I can leave it in longer, great. Or, take whatever's in out, and try sizing up to a 4th item. If I can, then that item's the goal for next time. If that largest size I had in (the third item) I couldn't keep in the full 10 minutes, then back to the 2nd one and leave it in longer, then try for the 3 at 10 minutes each for next week. Depth Day: Goal is to stretch my hole deep, and breach the second hole, get both used to being probed, touched, and caressed. I have trouble taking 6" right now, my hole's too shallow. Since the goal is to get used to being filled deep, it's again a case of mostly plugs or plug-like things, or just sitting on a dildo and maybe doing work on my laptop (multitasking!!). I have Topped Toys' Deep Space 70 and 80, and I have trouble keeping the 70 in more than 5 minutes. So, the goal is to keep that 70 in for at least 30. Then let it slide out, and try for the DS 80. If I can get it in, keep it in as long as I can. If not, well, try again next week. [Destroy] Grip Day: Goal is to bust my ring so a top can slide in, nice 'n' smooth. I realize the ideal for this is something that has a gradual taper and then a "snap" closed neck, but I don't really have anything like that. Well, maybe the "Hunter" dildo from Bad Dragon. So, the mechanics of this one are to get the toy in, then bust it out. Over and over again. Really popping my hole, assaulting it, forcing it wide open again and again. Not a gentle stretch except at the start, but really busting my ring. Of all the "exercise" days, this is the one that gets me the hardest just thinking about it. Piston Day: Goal is to practice riding / sliding on a nice dick / dildo. It's not to push depth, not to push width, not to bust my ring, but get used to that sliding motion. If I owned a fuck machine, I'd just strap myself onto it and put a reasonable-sized dildo on and let it go to work at maybe 50 strokes/min. Just ... get fucked. Rest Day: No rest for the wicked. There should be something in my hole no matter what, unless it's really too sore. The idea is simply to use a small plug and go about my business, be it sitting to work, or grocery shopping, or napping. It's been suggested I work more with poppers for this, so I'm looking to get some more, especially for the [destroy] Grip Day. I'm also trying to decide if I should get a chastity device to help focus on my hole more. Anyone have any thoughts on this?

Starting my journey to reach 100 loads this year I started by taking a 135 mile one way trip the Club STL bathhouse. I was there from 12:00pm to 6:00pm. I spent the entire time alternating between being ass up in the dark room, in the sling and blindfolded in my room with the door wide open. In that time I got ONE. ONE GOD DAMN LOAD after a 270 mile round trip. I dont understand the STL bathhouse, ive really never seen much action there but Friday felt exceptionally off. When i was in the dark room there was a young twink getting hammered by a young hot guy. There were 4 older guys watching, stroking themselves. I presented ass up but nothing. When the twink finished the old guys swarmed him but he pushed them away like a vegan getting a complimentary ham sandwich. But the just went back to stroking and doing laps in the dark room. Never did they do anything with anyone. There was another bottom posted on the fuck bench. He was there for several hours with no action. The entire time I was there I saw the twink get fucked and i got one load. That is all i saw. I may have missed some action, but what i saw was dead. This is the shit that really discourages me. The time and money i spent going there for this outcome is a gut punch. But oh well, 1 load down 99 to go. I have a party scheduled on the 16th, so we will see then.

Tonight I had T for the first time and sucked this silver haired older man. He partied the night before so he got me cloudy. Fuck did I love sucking his cock. He thought I did such a good job that he paid me money and gave me some cash for my troubles. It started out with ten bucks but after we were done and I had him cumming down my throat we were up to $50. He was trying to constantly pimp me out. But it just didn’t pan out. I think I’m going to go over tomorrow!