Today I got this question from someone I have previously played with. I had opened him up in my sling but he didn’t manage to get my hand inside him. I remember thinking at the time that he had quite a way to go before he would be wide enough to take a fist despite his obvious enthusiasm – which is second only to his love of punctuation.  😉

Hi Andrew,
I would like your honest and experienced opinion on something!
This weekend my boyfriend and I spent time with a third person, had loads of hot fun, pretty much no holds barred, to the point of said person pretty much saying that he could fist me without a problem , even though I had told him I’d been unsuccessful in the past. Of course I ended up in the sling, totally relaxed and lubed, amyl etc. Black rubber gloves, lots of pre stretching, there couldn’t have been any more preparation!!!
As I feared, our goal wasn’t reached, no matter how we tried. He said at the end of our session that he didn’t think I would ever be able to take a fist because of my pelvic bones and their location???
I know myself that I’ve been able to increase the size of things going into my ass, and have always thought I would eventually reach my goal of the Fist!
My question to you is do you believe that someone could be anatomically unable to reach the stretch I want, no matter what???
Or…is this man just a bit pissed off he couldn’t deliver his promise???
Please be honest with me!! If its not going to happen (which I don’t want to believe) then it’s not! I know the feeling of the bones that are sort of in the way of my conquest, but assume I can work my way around that! What do you think????
One more thing… while training I tend to try bigger in width, and tend not to take no for an answer. Should I be training for depth as well ? Maybe something narrower and go for maximum depth??? I know I’m being impatient, but will appreciate any advice or answers you can give!

Hi David,
I have heard of people who haven’t been able to take a fist because of their anatomy but these cases tend to be very rare. Almost everyone can be fisted but it does take time and patience. I know of one boy who took three years to get to the point where he could take it. So take your time. From my one time play with your ass, I didn’t detect anything that made you think that you couldn’t be fisted – but I do think that you do have some time to go. You aren’t as loose as you think you are.   😉
I know that taking a baseball bat seems like a big deal (and it is – and it looked awesome in your ass), but there are some big differences between toys and fists.
The uneven shape of the hand means that even boys who have take toys much bigger than a fist can find it really hard to take their first hand – because it puts pressure unevenly on your hole.
So my advice is to keep trying – slowly and carefully. You expressed surprise at some of the large toys I had. The reality is that you’ll probably need to practice on toys that size. Go online and order yourself a Bam or Blackball – or really any 2.5 or 3 inch toy.
Fisting is a long term goal. To us older guys it always seems a bit unfair (in an awesome kind of way) that there are teens out there who can get punch fucked – but everyone is different (and teens love to practice putting things up their butts – remember how much spare time you had at uni?)
Personally I would focus on width rather than depth. I’m not a medical expert but it seems that the risks are lower and frankly its more fun.
I’ve been with boys, like Sissyboy, where I knew that he was ready to be fisted – the only question was ‘is tonight the night’. I didn’t get that impression from your ass – you have more practice and work to do.
There are some amazing fist tops with small hands. The size of the hand really does matter. But ultimately, you need to enjoy the journey. There is an end goal  – but you have to enjoy the process of having your hole opened up. You can’t only be fisted for the first time once – so take your time and enjoy the journey – it will happen when it happens.