Hey peeps. Iv bin wanting to step up my anal play lately. Have a few prostate massagers, only reached orgasm once with them and wanted to step it up a bit, bigger the better n all. Ordered one that was a bit bigger, tried it out last night n was way bigger than I thought once in. I presume I’m not the only one here that’s had this. Weather it’s anal or vaginal any tips be greatly appreciated
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Is it hurting you?
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Even having gotten used to some of the bigger prostate massagers and dildos we have, I still prep by using a smaller butt plug and some times going to a bigger butt plug to prepare for what I eventually am looking to use. Do this all the time before wife pegs me. I also recently bought a larger prostate massager and prepare for it by wearing a little smaller butt plug before diving in. For me makes it more pleasurable when their is no pain. Use plenty of lube as well.
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A small increase in plug diameter can make a big difference when you’re trying to insert it.
You may need to work up to it by using an intermediate sized plug first.
Alternatively use plenty of proper anal lube and insert it a little more each time over a few days. That’s how I finally got my big plug (9.5" circumference) to fit in.
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Jesus this one only 6 inches! Does it feel better when longer n wider? I worked out how to hit my prostate with smaller one but heave to keep my hand on it all the time. Rather my hands be free
I don’t try to force bigger vaginally because it hurts.
When I did participate in anal I had to use a plug initially and then really take to slow. I needed to be the one to back up onto him and it would be just a little bit at a time.
Saying that, my 2nd time having anal sex was with a guy that I named ‘cock can 
’…the original can 
I have no idea how he got thon thing inside me but I remember enjoying it!
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I found some inflating toys to slowly stretch myself out, and yes always use lots of lube. Slow and steady is the way with any anal play.
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@JoCat fucked up trying anal with the wife. It was me putting into her rather than her leaning onto me. Put her off it, even though was her idea to try it put her off. I will try use the smaller one first then. Thanks for all the great help dudes
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If I’m honest my medium plug at 7" circumference feels nicer against my prostate than the larger 9.5" one but I like a challenge.
I can push the medium plug in with my fingers whilst lying on my side but I have to place the larger plug on a flat surface (like a kitchen stool) and lower myself down on to it slowly and carefully.
Your wife might feel safer with anal if she straddles you in cowgirl so that she can lower herself down onto you. That way she can control the speed and depth of penetration. That’s certainly the position I used when we first started pegging.
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My smaller one was only 4 now gone up to six insertable length. Have it on charge now n chilling with a beer to loosen up a bit. Hopefully put me at ease. One thing I have learnt is of your not in the mood you can’t force it, lot more complicated than a quick wank! Yea we should have done something like that. She was jus lying on her front n I pretty much went straight in, she wasn’t spread or anything, very stupid way. It put her off a bit, hopefully she will come around to trying it again
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Gradually go up in size don’t force it. Make sure you’re relaxed and in the mood with lots of good lube too.
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Gone from 4inches to 6. Thought be a simple jump cause wanted bigger. I do want bigger jus didn’t realise the jump. Surprised me a bit, know what I’m getting myself into now. Gunna give it a go tonight hopefully
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honestly after failed / bad experience rushing into anal years and years ago we didn’t retry until recently. All I can say from a female perspective was gradually increasing from a finger to two to the tip of a small dildo to 6 inch to then my partner… was a gradual and slow progress. Lots of lube and breathing relaxation to get beyond ‘the second gate’. Now we have a blast, but no need to rush, don’t hurt yourself and stretch gradually and regularly
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I would advice you to get a plug or a toy like the Doc Johnson Titanman Intimidator, to work up in to bigger toys.
A small increase in diameter is already quite big a big increase in circumference. Desides going really slow and use lots of lube is the key with anal play.
Slowly get the toy a little bit further each time and never force anything.
When you pushing in the toy in try to bear down on the toy a little bit this will open you up your anus a little bit more. It will make working up in sizes a little easier, this at least is what works for me to insert big toys and getting anally fisted
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I will agree with everyone . No matter which toy I want to use , I always start with a small tee plug that is quite tapered . And depending on how large I want to go to , lube , lube and more lube for the larger toys . Whenever I am hungry for my 9" I make at least two warm up ( and lube up ) steps on the way up . I have three prostrate massagers and the largest is BIG . I rarely use them and the largest very rarely . I find I get much more enjoyment from my tee plug and my favorite WeVibe Ultra Egg because they both stay in while moving or walking around . And the egg has given me the best orgasm ever . I make funnest home videos while using my toys . The best is watching the 9" slide it for it’s full length , visually pleasing . A close second is my 6" rainbow dildo , watching each color disappear into my tanned back side . Third best video is watching me ride my 7" dildo with balls where I back into it " balls deep" . While using a large toy , remember that each time you insert it the entry point removes most of the lube . So multiple lubes and entries work more lube further up . Some times the anal slut in me demands the full 9" .
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I always say with anal, rest it against your hole and then kinda push your ass like the motion you would while having a poo, I find that’s what helps open me up
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Sounds like a case of eyes bigger than your manhole! 
yes plenty of lube and warming up to it is always a good starting point… maybe start off with one of your prostate vibrators to get you opened up a bit before trying the bigger one or even if you invested in a butt plug or an inflatable plug that will help you to transition to bigger sizes more comfortably 
I’ve run into this problem early on in my anal exploration days.
Hear a few tips. Maybe this will help a little.
- Try in the shower (by yourself), first. Warm water will relax you
- Lube as others have said. Plus water makes the Lube last longer assuming it’s Water Based Lube (and with few exceptions it should be).
- Try getting in the “pooping in the woods,” position. And slowly sit on your ankles with the toy in position. This opens your Anus much wider than you would expect.
- In spite of how big your toy may look. Take a deep breath and relax. This will help your Anus open more than you would think.
- Alternate between deep breath relaxing your anus and “pushing to poop,” while in that pooping in the wood’s position.
- Pushing actually opens your Anus the most, which seems counterintuitive but is true.
I went from a prostate massager to a waaaaay too big toy and letting my GF peg me with it which wasn’t a stellar success. It was after I had stretched in the shower with it though. It’s a process and if you look at it more like a challenge for yourself and a marathon. I think you’ll find that journey very enjoyable.
Don’t rush it. I did. But I’m a bit of a completionist. I’ve taken over 14 inches and made it all disappear and my GF semi regularly pegs me with the Intimidator now. It’s an acquired taste, but if you find the joys of deep penetration like I have. Well, deep long strokes are the only way I can have an anal orgasm, and with the right toy the prostate ones (with no penile stimulation), that come along with them are…unlike anything else I’ve ever felt is all I can accurately describe them as.
Don’t give up if it’s something you’re interested in. It’s worth it in the long run.
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Forgive my ignorance but 14” inserted sounds really long. Is it OK to put such a long thing up there? I’m not clued up on anatomy but could it do damage because I think the internal organs are pretty delicate?
I’d like to know more because Ive ordered jiggle balls and and beads from LH and i’m a bit nervous about using them.