My messiest orgasms have to be when I ruin them. I normally have a towel up as the first time I have a ruined orgasm I have loads of cum and seem to shoot quite a distance. Then after it’s still a fair amount but still needed otherwise it’s everywhere. Very fun too
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I don’t make a lot of mess but for my husband it is definitely when he gets a wet dream. Fortunately it is all in his underwear but always very wet and sticky.
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We’ve had a few squirting incidents which are pretty messy, but as sploshing fans the messiest orgasms all involve a few buckets of gunge and lots of custard 
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With my current partner one NYE, were quite drunk but also extremely aroused, we had the most amazing session, she’s a bit of a squirter and the bed was absolutely soaking! When I was about to cum, I pulled out and tried to cum all over her face and tits, only when you’re drunk you have absolutely no idea where it’s going to end up! All over the bed and a couple of walls. Got up in the morning to see cum running down the window 
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Probably when a previous partner first gushed, We had been trying for years and it just wasn’t happening. So we agreed we would forget about it. Fast forward a couple of years and she was kneeling down in the living room giving me a handjob/blowjob, I had slipped my fingers in her while she was servicing my penis,and would you believe it she gushed buckets full lol she was still wearing her knickers well they were soaked and so was the carpet. We were both 
She went to clean herself up and when I went into the bedroom she had left her knickers for me to keep.
Still have them even though we aren’t together anymore.
In my younger days I was nicknamed Canon Cock because if I was given a handjob it would literally shoot out and go everywhere, I remember someone’s house and the armchair got splattered and that’s when they nicknamed me canon cock.
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I had a 1 hour long prostate masturbation session (on my bed lying on a towel with my Lelo Wave 2 and tons of lubricant) that involved me having 6 wet prostate squirts (which is where you dribble out quite a lot of squirt from your penis) all over myself so by the end my entire stomach and the sides of me down onto the towel were covered in my squirt, very messy haha!
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For me it would be when I ruin my orgasms. During those sessions I cum multiple times so have to put a towel down or sometimes use a condom. If I’ve been edging too it can get even messier.
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Probably the messiest was after an intense session in the missionary position when we were using the withdrawal method.
I said I was about to cum, she told me to pull out and aim it on to her stomach, I said I am going to aim it at your tits, and it ended up missing her completely, which is lucky as if it had ended up on her face or in her hair, I would never have heard the last of it.
It plastered the headboard and wall just above her head. Whilst she was slightly annoyed by the mess, I was secretly quite pleased with range and quantity.
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My messiest orgasm was a quickie in a quiet place after a few drinks at the pub. We hadn’t done it for over a week due to hubby working away from home.
Fully clothed we had a standing knee trembler as we couldn’t wait until we got home. He made me come pretty quickly with his fingers then slid inside me and came extremely hard.
Walking home I could feel his cum dripping from me and soaking my thong, which couldn’t soak up such a load and eventually I had cum running down my inner thighs. Messy became uncomfortable by the time we got home.
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Probably when my OH give me a power wank with the Lovehoney Head Master Double Texture Blow Job Stroker. it was the tightest thing i’ve ever had round my member, took a lot of lube to get it on , I asked her to slow down but no 
and I was spraying like mad in no time, flying everywhere
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I am a big cummer, but if I haven’t cum for a week or two (I like to save it up as I work away all week) my huge load combined with making mrstoysrus squirt everywhere, is always messy, we always have a sex towel handy, and have a waterproof undershirt on our mattress or else it would definitely have rotted away by now!, it’s been a few weeks since I’ve last unloaded and mrstoysrus is out on the town tonight, so I’d imagine it will be messy later….always happens when we’ve just changed the bedding too!
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Messiest orgasm I have given OH was the first time I made her squirt.Neither of us knew she could squirt and were unprepared for it so it went everywhere bed was soaked as was my hand.my messiest orgasm was the last time OH had managed to fist me she was in what I call her dom outfit and gets me so turned on I was so horny .I was in missionary legs splayed open OH applied copious amounts of lube to her latex elbow length glove and my ass gently stated to finger me and eventually had her fist in me playing with my prostate I stroked and when I came I spayed so much it hit me in the face
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When much younger and single I picked up a hot woman from a bar . We went to her new step dad’s mansion . OMG ! The place was amazing , we ended up in the game room - bar that had a hot tub . She was riding me cowgirl style and started squirting , and squirting . The volume was the most I have ever seen . I was literally covered from my beard to my knees . As a footnote she passed out and did not come out of it . Checked her pulse ( I was an emergency medical tech at the time ) , no pulse . I was about to start CPR and she all of a sudden gasped and started breathing again .
A somewhat more recent time my wife and I had been drinking a fair amount and had been going at it in different positions . I had cum in her several times and she had a number of gushing orgasms . We finished up by doing the 69 clean up . Then we fell asleep . We were a sight when we woke up , my beard was covered in our mixed juices . We both had dried cum all over our bodies and were both partially stuck to the sheets . Clean up required a long shower where we. had to fuck each other again . Memories !
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A follow on from my above post, as I suspected I did cum a lot last night, in fact I’d say that’s the most I’ve ever cum in my life, and I unloaded inside her, but it was flowing out of her onto the bed, my cock, balls and asshole we’re covered and the tops of my legs, was a very intense sensation, it wasn’t just because of the time between when I last unloaded, it was a very sensual night
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When it comes to messy orgasms, this is something that has only really just started to happen with me and my OH as we explore our sexuality more. We have found that my OH is a bit of a squirter, not a gusher, but certainly squirting. She has done this a couple of times, once on my hand when I was using my fingers in her and once on my cock while we were PIV. As we explore more I have found that she can orgasm from being fingered while she is performing a BJ on me which makes for great PIV after. I am looking forward to the day that she manages to squirt on my face while I have my head between her thighs.
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Probably a couple of years ago. Just a normal solo session where I was turned on just that little bit more than usual, and probably a little harder than usual.
To cut a long story short when I came it SHOT further than I ever have before. Some went over my head, and a little landed on my cheek.
I was genuinely flabbergasted!
Would have been livid had any gone in my eye.
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I’ve just remembered another messy orgasm.
When we were in the early stages of our relationship my husband used to bring home porn DVD’s he borrowed from a work colleague. I was fascinated by the way most porn films finished with the girl getting cum shot all over her face. I asked my husband to copy a video that we had just watched as I wanted to experience having cum on my face like a porn star. He didn’t need asking twice and as we were both very turned on we went through the various tricks played out on the screen. I don’t know whether it was the highly sex charged situation we were playing but when he came to the orgasm it felt like he had literally covered my face and it started to drip down on to my breasts before I could stand up. I looked in our bedroom mirror and he had produced a monster load far more than the guy in the porn video. I had so much cum on me that I had to take a shower. 
And what did hubby do? He photographed the aftermath with me covered in cum all over my face and breasts. We still have that photograph in our sex album. Now that’s s good topic for discussion with others.
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Would have to say when OH squirted in my face we weren’t expecting it as she had never squirted before
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This morning, had been edging all week, so when we had sex this morning, there was a lot of cum, something special about a decent cream pie, but also her inner thighs being glazed as well as her trimmed bush.
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In recent history I’d have to say a couple weeks ago when I went down on the OH. I don’t think she was expecting it and she must have been pretty worked up that day because within minutes she was soaking me and the bed. I’m so thankful for waterproof blankets 
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