Back in early 80’s before meeting MrsIwill…i had been seeing a girl, but had gone on holiday with my mates.
When I got back ( i had been genuinely faithful while away.) , she was desperate for a good shag.
We were on the floor of her parents lounge ( a kind of coarse pile carpet). She was on top and riding me cowgirl, with me rocking my pelvis to meet her movements.
She wasnt in mood for a quicky and wanted a prolonged session.
Later my butt felt rather tender and the next day the cheeks of my ass were red raw…couple of days later, im bent over an examination table in Doctors surgery with boxers round my ankles.
" oh youve got a rather nasty skin infection " says Doc…what happened to cause this.
Embarrassed I stuttered that i was a van driver( i wasnt ) and had been driving extra shifts and it had been hot recently and had been sweating.
He goes in to an explanation about when you go to loo, you pass acid as well and if skin broken it can cause an infection.
Prescribed some medicated cream to be applied.
The girl i was seeing found it hysterical, she didnt even volunteer to apply the said cream.
Obviously not a keeper if she’s not willing to slap on some soothing ointment. Even though shag pile is in the name of the carpet doesn’t necessarily mean it’s up to the task. 
Hope not to repeat myself too many times on these pages on different threads 
Walking naked in woodland two years ago I got stung on the end of the penis by an unknown insect. It got somewhat inflamed for a week or two but the infection gradually reduced. I know I should have seen the GP but heyho.
When activities with my o/h next occurred, it must have still been tender. There was some blood afterwards. I thought initially that she had begun a period, but no It was me… I had torn the foreskin as it must have still been too tight.
Of course I didn’t get help this time either. It healed up by itself, but wouldn’t retract at all. Fast forward to now and after a couple of urology appointments, I’m on the waiting list for an operation I don’t want.
Wish I’d gone to the Dr right away, now I’m facing a general anaesthetic & weeks of pain.
But there’s a positive that comes after the all clear and hopefully a big celebration.
Thanks for your good wishes, I am just not looking forward to the procedure nor the recovery. The leaflet from the surgeon is enough to frighten anyone.
Does getting some skin from your penis caught in the zip of a latex catsuit you were wearing count ? 
painful and expensive day that was
Once cut my forehead on an unfamiliar headboard whilst on holiday 
This gave me a good chuckle, well done for getting it out I would have panicked so much
At least you didn’t have to get it medically removed, that would have been a fun one to explain (;
Worst injury I can recall was one night my wife was riding me cow girl style and getting extra wild . She was a woman possessed and by the end of that session I thought she had broken my cock , which years later I found out was a possibility .
Best was many years earlier , I had three exploded disks in my back that hurt all the time . Girlfriend and I went parking after an evening church service and were going at it in the back seat , POP ! My back pain was totally gone for multiple days .
As @WillC mentioned , I also often ate pussy so energetically that I got tongue cramps .
A previous boyfriend was a bit small in the penis department and we used to have sex in his car. I was not on the pill at that time, so he used a condom. This one night after we finished he said that the condom was missing from his dick! We had a quick look around the floor of the car and not finding it he said that he would look in daylight tomorrow.
Imagine my horror when I was sitting on the loo later and found a condom hanging out of my Vag!!! 
Not ever wanting a repeat of this experience, I finished with him a few weeks later. I think his reaction to my dilemma, by killing himself laughing, didn’t endear me to him. 
Aaaagghhhhh !!!
@Love_Stud_Too … No im sure it didnt endear him in anyway at all.
I would have kind of thought, that was the most obvious place to look, if he had shrunk quickly after ejaculation.
One of first girlfriends wanted a walk in the woods before I went on holiday. She picked a nice spot. Got naked and she went for it. Didn’t know what poison ivy looked like. We do now.
Very much soo
When I used to use condoms this was one of my worst fears, I’d probably be sick if it happened to me 
Not an injury, more at the “mishap” end of the scale.
Went to a country house hotel for a wedding years ago with my then-GF.
Arriving on the Friday we checked in to our room and did what everyone does when they arrive in a new hotel room 
In the heat of the passionate moment of undressing one another my GF, clearly getting frustrated with my typically male uselessness at removing her underwear, gasped at me “Just rip it off…”
So I did. And didn’t hold back
Shenanigans over, she rolled off the bed and stood up, clutching a shredded bra to her chest, snapped knickers hanging round one thigh and thoroughly laddered stockings falling down her legs, having a little giggle when she caught sight of herself in the mirror.
I lay there also feeling suitably smug at having ravaged her as per her instruction.
But…the grin vanished off her face and she looked horrified as she said “F***, I needed this set for the wedding tomorrow”
The bra she just about salvaged, but went commando otherwise so it wasn’t all bad.
Hahaha this is such a typical man thing I think.
My partner does this all the time, I can’t tell you how many pairs of tights and stockings I’ve gone through (;
Many many years ago we stayed at a B and B in Blackpool and decided to have some steamy shower sex the reality was it was a tight squeeze in the tiny cubicle parts of my body inadvertently turned the water temp up in a mad rush to avoid the scolding we both got jammed trying to get out until she popped out going boob over bum onto the bathroom floor legs akimbo on her back.
After laughing hard for five minutes I did check she was ok and help her up
I once had an ex accidentally cut my bellend with a tooth during a very enthusiastic blowjob. There was a surprising amount of blood.
It was well intentioned.
Oh goodness! Sex in a tight shower never ends well it seems. Hopefully she saw the humour in it too 
I once knew someone who set off the fire alarm in a travel lodge from having steamy shower sex with the bathroom door open