Originally Posted by nicelyvillainous
Oh, and for plug sizes, generally a finger is the smallest size, at abt .5-.75 in in diameter. Go up by about .25-.5 inches in each size, most toys are tapered, so to put them I get in a position where your ass is spread and slowly fuck them in with plenty of lube, gently push them in until there's too much resistance, pull them out halfway then in again, don't push so hard there is pain, stop at gasps or whimpers of mild discomfort, each time you do this the sphincter will get tired out, so it will slowly start going deeper and deeper. There's often a tiny spike of pain when it the sphincter stretches over the bulb and "snaps" shut, pulling the plug into you to quick and stretching the inner sphincter. Butt plugs are the shape they are so your outer sphincter holds it in place to gently stretch the inner one.
Let it sit until your body gets used to it, then you can start stretching by slowly pulling it in and out to stretch you around the thickest part. Once that stops feeling uncomfortable you can move to the next size. Butt plugs also work if you just wear them for 30 mins -1hr before moving to the next size. It is entirely possible to need several stretching sessions to successfully stretch to move up to the next size, because stretching makes you sore you you stop with pain.
The most common size of cockring is 1.5" diameter, I have a very big cock and wear a 1.75", porn cocks get up to 2 or 2.25" but 95% of those are dildos shot so they look real.
See what size he fits, you can pick up rubber washer prints at the hardware store pretty cheap. Have safety scissors to be able to cut them off if he swells and can't get out using ice.
If he has a 1.5" cock, it is up to you whether you want to get a 1.5" or 1.75" plug so he can slide in easily excel when you squeeze down on him, or to stop at a 1.25" or 1.4" diameter size so he is the "next size up" and an uncomfortable stretch which means he'll have to go slow.
Position also matters, you want your knees near your chest and together for the most space available it'll line everything up etc. so it can be on your back in a piledriver position, in a crouched doggy style on the bed, or, probably the best because it gives you most control on speed at first, a seated reverse cowgirl, where he's sitting declined at the edge of a chair/bed with his legs spread and you with a hand on each knee and slowly sitting on it. There is no obligation to go all the way down, and I would suggest you talk to him, because he will be happy to be making progress and not demand that you finish him off with that hole on your first few tries. On your back with on the bed with him standing and your feet on his chest also will help because feeling like you can get him to slow down/back off if you need to safeword will help you relax more so you DON'T need to.
In fact I think I'm going to assign you two a task to do once you are healed and haven't gotten any red stripes while wiping for at least a week. Get on your shoulders with your ass in the air in front of the couch, with your back against it. Have him sit on the couch and play with your ass, with his feet on the ground just above your shoulders so it helps you not slide down. I would suggest that he tell you he's decided not to use more than one finger before he starts, to help you relax, but that is up to him. He should make sure to trim, file smooth, and scrub clean at least that finger (probably the middle finger on his dominant hand), or you can provide service by doing it for him. He should put on tv that he enjoys, and enjoy gently spanking and kissing his girls ass, and absentmindedly rubbing his new hole to play with in circles, pressing his finger against it and tapping on it, rubbing lube into it, slowly pushing lube inside it to the first knuckle over and over, then slowly sinking his finger in and claiming it, and gently pumping it in. He doesn't have to fuck your hole for you to submit it for his pleasure. He may have you play with your clit while he does this, with or without permission to cum, or he may have you kiss and worship his feet, or he may have you wear earplugs and close your eyes and focus on the sensation while he watches his show. Make sure to tell him when you start getting stiff or sore, so he can decide when to stop with all information, and depending on your relationship, clean the mess you made in his finger (likely just lube), either by getting a warm soapy cloth to wipe it clean and sucking him dry, or right away with your mouth.
Seriously though, have a conversation about what he wants from you. I think that he probably just needs to know that you don't look down on him for knowing different things than what you learned in college, and that you have plenty of reasons to respect him even if he isn't eloquent. And I read between the lines that you may have some ego tied into being "smarter" and throwing it in his face on occasion, but the point to address there is arrogance and discourtesy at flaunting vocabulary you don't expect your audience to know. But rules should be designed to remind you to be considerate instead of condescending, not to punish you for being "uppity", if that makes sense. And I suspect he will agree if you discuss it and he isn't adressing the issue while frustrated with you. Of course, I could totally be projecting my baggage history with the reading between the lines.
If you are still a fan of the "Sir" rule, I would suggest going even more old school and childlike, and having you address all other men as Mister, while keeping Sir reserved for your master.
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