Jump to content
  • entries
    65
  • comments
    130
  • views
    15,831

Boxing Day? Well, He Tried...


A man wrote to me yesterday, seemingly quite fascinated by this pic I have on multiple hook-up sites...

https://assets.s3xstatic.com/bz/uploads/monthly_2018_09/large_Hole.jpg.02a8bd1d5df855bbf957d4576683793a.jpg

Now, I don't know what it is about this pic that makes men like him think I'm an absolute slut-bottom - apart from the blindfold, the poppers and the hungry, gaping hole - but he started out suggesting a solid, old-school fuck with his 7" cock. That sounded appealing enough to me, so we exchanged a few more messages and I checked out his profile where he listed "fisting", "outdoor fisting" and "group fisting" among his interests... 

Yeah, you're writing to me about my gaping hole and you just want to fuck me with your cock? Sure... 

And true enough, a few more messages and he began mentioning toys, fingering and so on, so I jumped the bull and straight-up wrote to him that he would be unlikely to be successful if he tried fisting me - but that he was welcome to try if things were going well.

So I showed up at his place by 10pm, and within 30 seconds I was on hands and knees in my jockstrap - next to an assortment of dildos ranging from "YES, PLEASE!!!" to "that looks a bit daunting". But you know me; I stuck my hole in the air, took some deep hits of poppers and hoped I could satisfy him.

I had told him I'd be tight, but he seemed a bit disappointed that it took a fair bit of pressure to get even just two fingers up my arse. I think he had expected them to just slide in, but hey... I might become a gaping hole after a fair bit of work, but my sphincter is in full working order, so it's normal for me to be tight at first. Anyway, I begged for his cock - as you do - and while he got himself undressed I loaded up on poppers and told him to shove it completely inside me from the start so I could REALLY feel I was getting cock-stuffed!

And boy, oh boy... 7" of good, hard cock went inside me in one go, making me whimper but also getting me into the right head-space where I was just there to take as much as possible, even when that included some minor discomfort.

He clearly knew what he was doing, pounding my hole from different angles and spending a bit of time just punching his cock head in and out of my hole, softening the rim and opening me up. I love how an experienced top can open a hole with just a regular-sized cock...

Then came the smaller of the dildos - a standard 8" model that I've been fucked with by lots of tops. It was filling and satisfying, being a bit thicker and longer than his cock, but he soon tired of that and upped the game to a longer and thicker dildo that definitely went a bit deeper than my comfort zone but it was still reasonable and I knew I'd adjust to it. (Also, that's what poppers are for, right?)

Every so often he'd pull out the dildo to check on the progress, and eventually I could feel my hole staying open when the dildo was pulled out, so I reach back and put two fingers from each hand in my hole and pulled it wide open for him. Well... That point was definitely what he had wanted when he initially contacted me!

My hole remained open when I let go, and he was able to just slide his cock in and out of my hole with zero resistance, each time punching it in balls-deep and then pulling out entirely - repeat and repeat... 

He was definitely a bit of a demanding top - but then, I can be a bit of a demanding bottom at times, so I reached back and started putting my own fingers inside me alongside his cock, giving him a bit more resistance and giving me a bit of stretching. And eventually I reached for the 8" dildo and when he at one point pulled out entirely I quickly inserted the dildo all the way in my hole and pulled down on it, indicating ever so subtly that it might be possible to him to slide in alongside it...

"Might be possible" - yeah, right. I knew I was open and ready for it! So he double-fucked me with his cock and the dildo for a while, but then pulled out the dildo again. I guess he really wanted to feel his cock in an open, un-resisting hole - and there's something very satisfying about taking a hard cock balls-deep and just being completely relaxed about it because your hole is so open.

And yeah, he tired of that after a while and gave me a single finger instead of his cock, probing around and feeling how soft and open I was. Then one more, one more, one more... Yup, he was definitely going to try to fist me!

And we really gave it a pretty good go; I haven't been stretched that open for a long time, so I doubted if I was in shape for it - but we definitely got a LOT closer than I had thought we would! Not quite the hand, but certainly five fingers. He worked me for quite a long time, and it felt REALLY great - but I could also feel that I wouldn't be able to get that little bit extra open it would take for his hand to get fully inside me. 

He seemed happy enough with how far we actually got, though, so when I eventually warned him my hole would soon be getting sore he pulled out the hand and resumed fucking me until he dumped his load in me.

When I got home I had a wet patch at the back of my jeans where cum and lube had leaked from my open hole... The next time I visit him I should really bring a fat butt plug to prevent that - because there definitely WILL be a next time. We got so close, so I'm sure he can get a hand inside me if we just keep at it - and he seemed pleased enough with what we managed last night, 

https://assets.s3xstatic.com/bz/uploads/monthly_2019_08/large.IMG_4338.JPG.823f131b4d5e204374e3970306854f59.JPG

When I got home there was a message from him, telling me he'd like another visit soon - and that I should try to keep my hole in practice by playing with it on my own as often as possible... Well, it was time for me to go to bed anyway, and my hole was open and wet, so I spent a good 15 minutes with four fingers in my hole before I finally went to sleep - and this morning I could still manage 4 fingers, just with the lube that was still in my hole! 

I haven't been fisted in years, but I'm quite determined for it to happen again soon. 

0 Comments


Recommended Comments

There are no comments to display.

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now
×
×
  • Create New...

Important Information

By using this site, you agree to our Terms of Use, Privacy Policy, and Guidelines. We have placed cookies on your device to help make this website better. You can adjust your cookie settings, otherwise we'll assume you're okay to continue.