How long have you been practicing anal play/sex or stretching?

First time I tried anal it hurt but it felt exhilarating and new its been about 2 to 3 years on and off and I have been able to get up to 2.2 in width and tried Glass, Silicone, everything…

I guess I am at a standstill here and getting frustrated. I think we know of that feeling when a new toy pops in and it’s bigger and how it feels!

Realistically because of work and priorities some weeks I try to use a plug or stretcher every day and sometimes I go weeks without, I was getting a bit upset but noticed I have more control.

Anyone who’s advanced how long did it take? Thanks!

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I don’t do any stretching bit have been searching for a prostate orgasm ever since I heard of it 2 to 3 years ago so have tried lots of different toys and have been close but no cigar yet.

First time we tried anal was close to 40 years ago. Wife wanted to try and it did not work out well, it hurt her too much and we were very inexperienced. We didn’t try again for about thee years and this time it went much better. Made sure we used plenty of lube and took our time. Wife had no issues with pain this time and we didn’t practice stretching or butt plug. Wife has been pegging me now for over 12 years, first time it hurt a little but we took it slow. Now I think because mutual anal is such a big part of our sex lives my wife has no issue being able to take me or most of our dildos in her ass and same for me. We do have one dildo we do have to work up to but it is pretty big and I do have to work up to wife fisting but other wise I would say take it slow and relax and in time it will be much better.

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Been a few years just like @Fire_Ice1 looking for the prostate orgasm been close nothing yet. But will keep trying

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I’ve been stretching ALL day today because I have a pretty urgent time consuming city job. I love dressing in lingerie and playing but my god I’ve been trying SO LONG To get this glass plug in me (when looked at in real life from medium to large it doesn’t look so big) I failed again tonight ugh

The medium I can wear all day so comfy with is

  • Length:3.93 inch
  • Diameter:1.96 inch

Large is
( * Length: 4.13 inch

  • Diameter: 2.36 inch)

Like damn I just want that gratification! I’ll upload a photo, (the way its shaped when I start to get it in it hurts like my ass cheek bones I will have to wait and keep trying :frowning:

ugh I have such a stressful emergency city position (which im grateful for and I barely get time to play I take care of my whole family and responsibilities I just wanted to get it in for my birthday in 4 days didn’t seem like a large gap. Also sitting on a LARGE MEO 24/7 Anal Stretcher for years now (was a mistake buy)

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Whats the biggest in width of a plug or dildo you can take? and awwww Im so happy for you. Currently looking for a partner but my life is so busy with so much I literally have to play at night and sometimes dont sleep it’s a shame it’s hard to keep a routine. :frowning:

I’ll have a partner one day to help 100%

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I have a bit of a compulsive personality so once I started using butt plugs 3 or 4 years ago I wanted to go bigger.

I used plugs of increasing sizes till I got to be able to take a 9.5" circumference plug and a 10" long x 7" circumference dildo.

Subsequently I bought a Doc Johnson Titan Intimidator (looks like a small traffic cone) and I can take that all the way in till I’m sitting on the base of the plug.

I find that if I don’t practice regularly though I tighten up again.

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Both me and my husband have been doing anal for some time - I have been doing anal for about 25 years as I found vaginal painful as my husband is very long and he has been doing anal for about 5 years when we started pegging

To start with I agree it’s painful and you cannot just slide it it - it takes a long long time and to start with I would use a thin vibrator and keep it there for about an hour before sex - and over time used bigger and bigger but then found that I could not take the length as he said he was hitting a wall (about 2 inches in)

As time went on I started wearing a butt plug and would wear 4-6 hours a day and then started wearing longer plugs that insert longer and then one day- it happened I was able to take the full length of his penis and wow- it’s totally worth it .

When we started pegging I got my husband to do the same but it took him over a year until he was able to take my 6 inch strap on penis - but again it’s amazing and worth it

Always use a lot of lube and as others say - keep it open as if you give it time you will close up again and can be painful - and tell your partner as well to go slow - I find these porn films you see are just not real when you see some tiny woman just take the whole length with issue ……??

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Since I was old enough to develop sexual feelings and urges.

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We’ve been training my husband’s ass for about 12 years, and it gets compulsive! I agree that you need to do it regularly so as to keep up progress. I’m happy with being able to take cocks easily enough, but I want to peg him with monster-sized ones, thus we keep with the training. to be honest, I’d be happy stopping where we are, but he wants bigger!

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@KinkyMira

I’m the same since I started pegging my husband I want to use bigger and thicker dildos and I secretly like it when there is some resistance and I tell him to take it like a bitch…

I do get carried away but I get very turned on wearing a large realistic cock and want to bang him

I love the power it gives me - I can understand why young men always wanted to f**k every woman they see

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@batjamboree Oh, I absolutely get carried away. And the language I used when I’m doing it sometimes - if he said to me what I say to him, I’d not be very happy! He loves it though. Handy it’s natural for me!

It’s the thickness I like. A nice hefty girth. We don’t really do power in our relationship, but I do a bit with that. I just can’t help it. I think my favourite time in when he gets a larger one just in, and we need to work it in further and further. I’m not very sympathetic!

Pegging is the only thing I get like this with. I suspect how I am is why he likes it. I think it wouldn’t hold the appeal for him if I was all “You OK babe?” :rofl:

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You see I remember the first ever time me and the husband had sex and I was not able to take his cock and the next day had to buy ky jelly to allow penatration

I remember it hurt - he is just massive and before I was used to much smaller

Now it’s my turn to scare him - and it’s such fun

The other night while a bit drunk was getting him to see how far he could deep throat it while I was wearing it and I remember scoring him 2 out of 10 and then getting him to lay against the bed while I penetrated him

It’s great having such a naughty boy of a husband- he will do anything

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About the last half hour or so. It’s just real pretty , i might even pop it in soon
:grin:

If you’re done stretching, go deep !
@Penelope25

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Wow. That looks a-may-zing. Just shown my husband and I think he’s in love. What’s the girth like?

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Thank you all for the replies! I work all day and its night now and I have work again in a few hrs its sucks to have a few hrs to play especially after a hard day but Im being consistent and I don’t feel crazy, I’ll keep at it (I’ve deffinently gotten looser ! my older toys that would hurt or steel stretchers feel like nothing now! I want to stop at like 2.5 or 2.75 or 3 in width

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I wouldn’t call myself advanced, and we haven’t been particularly consistent or regular with anal play on either me (man) or my wife (woman), though to be fair we are currently having anal intercourse about once a month or so. We first tried anal in 2014 I think - she found it painful and I was so cautious on her account that I didn’t get any more enjoyment out of it than vaginal, and so it went back in the cupboard for about 3 or 4 years. When she was pregnant with our second child we took full advantage of the rampant hormones and in that 2nd trimester she was regularly begging to have all of her holes filled and a DP with dildo vaginally and me anally became a regular occurrence. Now she only needs about as much lube and prep to take me (6.5" long by 5" girth) anally as she needed to have vaginal intercourse when we were newlywed virgins - and occasionally she doesn’t want the lube at all.

We’ve also been practicing pegging and some prostate massage/anal masturbation for about the same amount of time, albeit far less regularly (I guess I’m just a wimp). Our starter dildo remains our go-to for pegging - I think it’s just about 5" long and 3" girth - but we have a next up that’s 5.5" x 3.75" and I can take alright. I have a variety of massagers that are up to 4.25" girth that are enjoyable, and this dildo I was only just able to take enjoyably.

All that to say: sounds like you’re on the right path. Just have fun - it’s not a competition except with yourself. Maybe look into some of the dildos that are super tapered to help with the gentle easing to wider girth (I think some of the new monster dildos are shaped more that way - that you dont’ have to make a massive jump in girth from one to the next, just ease down to the base). Anyway. Be happy and have fun!

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I’ve been stretching for about 4 years but recently have got seriously committed. This is because I wanted to be fisted anally. I very much enjoyed the small MEO plug from competitor so sized up to the medium - no chance.

Then I started working my way through Topped Toys Gapekeeper range. I’m on the 85 now which is 8.5 inches in circumference. Interestingly whilst it slides past the sphincter, you meet another challenge. Is the anal cavity large enough to accommodate it? I get an incredibly full feeling and can only hold it for 10 minutes or so.

It turns out I was able to be fisted anally and frankly, it’s exquisite. There’s nothing like the moment when you both realise ‘OMG it’s actually sliding all the way in to the wrist’ !

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I started when I was in my 20’s I’m now 56, but started stretching gradually bigger and bigger about 20 years ago mid 2000’s went from your typical medium butt plug to the largest that will fit between my pelvis +12" circ. I can take my wifes fist/duckbill about 12 inch in my butt plug is quite soft so squeezes between my bones where a hard version wouldn’t.

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We’ve been training my ass for about 10 years now. It started with a with a medium sized plug. That was bought with the intension to use on my wife but was used on me. We bought bigger toys over time and my wife kept adding more fingers each time we played with my ass, until she had her whole hand wrist deep in my ass. Because I love being stretched and completely full, I just kept on slowly stretching my ass.

Now I can insert a 10.25” circumference buttplug and my wife can double fist me. I definitely agree that you need to do it regularly so as to keep up progress.

Momentarily we working on getting deeper to be pegged with a huge dildo balls deep. She looks incredibly sexy with a nice ans huge strapon, She gets really carried away by pounding my ass hard.

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