Guys, When and How often do you ride your dildo?

I just am struggling with my first one! Desperate to get it up there but am tighter than tight! TMI?
 
Butt plugs are a great training tool. You can increase csize gradually over a few days and soon your dildo will fit just fine.
 
As often as I can get the chance. I have had the medium sized butt plug in all day while I interviewed secretary's. I am so ready to cum.
 
Wife' dildos

Like the heading says the dildos aren't mine but a couple of times a month I really get the urge to ride them so I tell my secretary that I have appointments out of the office and I go home when no one is there.
Once home I take off my clothes and start to play for a few hours. I use condoms on the dildos since they aren't mine. I'll start small and go up from there, the best one for me is one from Adam and Eve called X5 realistic dildo, we got it in black and not the cyber skin. Once I'm up to this size I like the ride it or keep it in for 30 - 60 minutes in which time my head goes blank of troubles and problems and I can just enjoy my alone time.
I don't always masturbate during or after my dildo play because not getting off keeps me happy and mello for the rest of the day and when I'm having sex with my wife later I can dream about the big dildo in my ass all the way to the balls - I'm not gay buy gay guys would love this s treat he'd deep ass!
Then when all done its time shower clean up the toys and any evidence and head back to the office with a sore, gaping ass!

Oh and my wife has no idea and would not be keen with it.
 
Love the feeling

I had a small vibrator that broke, that gave me the best orgasm you could imagine. Only used it a couple times but oh my! I NEED to get another one to replace it, it had a little curve that did me just right.
 
not enough

I used to have a nice sized dildo/vibrator but during our move it got destroyed so I have resorted to improvising. We have bought this plunger and its black and has an awesome handle with a large end and then tapers in and out. We never used it so I tried it omg it feels incredible and will milk my prostate quick as hell and talk about hands free orgasm booya this will do it. Its a cheap filler for now like 6-8 dollars at walmart. Ill put up some pics when I can.
 
I want to get a realistic dildo. It has been a while,but I am feeling the urge.
 
Mmmmmmm not as often as I would like but it's nice on a lonely night. I love to be tenderly fucked by a gentle, well-endowed man and imagining that while I'm doing myself is a nice fantasy.
 
I like to 'Save' my times with my vibe. I almost don't want to lost that awesome feeling that I get.

I think if I did it too often it would become less epic than it is now... If you get my drift?

So, yeah.... Once and month or maybe bi-monthly... I have been known to actually take it out and just hold it in my hand and then put it away and tell myself "Next Saturday" even though I could have used it there and then.

I have a VERY active and vivid imagination and so in those intervening days I would use my finger a little knowing full well what Saturday will bring for me.
I guess I enjoy the anticipation of using it as much as actually using it!
 
Well, I try to have the real thing more often BUT that being said during a dry spell I'd say every other day, maybe twice in the span of those days. Or if I'm busy and REALLY antsy a vibrating egg with a thigh-strap control GODS its intense trying to jog while that's buzzing but I love testing my willpower.
 
I slipped a butt plug in a couple hours ago. I've been out walking the dogs while wearing it, and I'm currently writing this with it in. I'll likely take it out before I go to bed, but I'll probably put it in again sometime in the morning.
 
As often as I can. Tonight for example but it has been ages since I have before.
 
I like riding mine 2-3 times a night. the orgasms are wonderful. also in the mornings on the weekends. I just love my toy.
 
justme

The girlfriend rimming and probing my anus with a Vibe while getting my cock sucked on, usually when were out camping...
 
Maybe 3 or 4 times a year tops getting ready to do it now, luv how it feels when the mood strikes have had several free hsnd organism, from the prostate rubbing, had a girlfriend that would fuck me with a dildo loved it now I do myself but would love a partner love sexy with girls best but I am horny and cum from masturbation every day. And luv anal
 
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