...should have been using a finger cot.

But it did happen with a civie. She was practically a virgin when I met her, and had not had sex for over 2 years when I finally nailed her. I pulled out and went to take off the condom and it was not there. I looked for it on the bed and then saw it still inserted in her pussy. Even without a dick inside of it, it snapped like a rubber band when I pulled it out.
I dumped her shortly thereafter because the sex was too arduous. Even with lube she was too tight.

Is it possible for a girl to be so tight that when she cums and starts to contract her pussy as you are still going in and out of her, she clamp down so hard that as you are using more strength to move in and out, the condom gets pulled off and gets stuck inside of her, even with plenty of lube?

I've had this happen once or twice when there wasn't enough lube.

There is this provider whose vaginal contractions are really strong and with me trying to push through while she's contracting my cock looks like it's been through a 100 round heavyweight boxing match.

Yup,
"Man who pull out fast leave rubber!"  However, Yes, if I cum first, I've had the condom stay behind.  The lady did not freak but used extra care in removing it.  
It's best to hold the condom during withdrawal...  
skb

not long ago, she put the condom after a wet bj, and in the K9 position, her contraction were hard that it pulled the condom of me. I was able to get it out easily.

The second, she was a petite lady, and her contractions were so powerful, that it really hurts. Again in the K9 position, I was in pain and instinctively pulled out fast, and lost the condom deep inside of her, I was able to get it out, but I had to go deep, and after several tries. She used one of those ultra-thin transparent condoms, and that what made it hard to get out as it had bunched up inside of her.

In both cases the condoms were not long enough, they covered about 2/3.

Happened once, she said her cervix is curved in an unusual way. Now I use pasante unique which adhere to the penis

If you cum 1st & she starts to come while your penis is no longer fully erect it is rather easy for a provider to steal the condom with strong vaginal contractions.  I would be willing to bet this occurrence might be more common with providers due to the pelvic muscle strengh and control most good providers have.  A condom that is too small or too large will only increase the chance that a slip may occur.  Pulling put as soon as you come should help prevent this.  I have felt this start to happen myself especially with one provider I used to see, her vaginal muscles were wrong enough that she would steal the condom when she came.  So I got in the habit of holding the condom when she was coming hard.  Don't forget to check condom position frequently.  If may benefit you to put on a new condom before you come.  If your having a marathon session it will help to make sure the condom is still properly applied, as thing do tend to shift in motion. I found some ladies are more likely to this then others.  So pay attention,  it's usually the ladies that have strong orgasms and strong pelvic muscles. At least you know she wasn't faking it.
Doc
p. S.  This can happen with any penis size so please ignore the alias chiming in with insults.  

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It happened to my babymama during a session with a client. Rookie mistake letting him convince her he needed Magnums when she knew better. Total fucking nightmare.

2 a.m. searching Walmart for a turkey baster and a set of tongs to perform condom removal "surgery" in the back of an SUV. Neither worked. Ended up going in by hand, practically had to fist her to reach the damn thing and pull it out. Ick.  

Hurt like hell for her; she kicked me in the face during the process, so it hurt like hell for me too. There's a memory I don't miss.  

 

Nope, regular size condom on an average size schlong, and only one girl who is really tight  has done this.now I am more careful and keep checking to see its still on.
And sorry to hear about your predicament tennyweenie, but those finger cots don't look safe. I imagine you've heard of them cause you have to use them yourself right.

be careful about lube (hers or artificial). If the condom is not rolled on all the way it is possible for some lube to get on you and work it's way under the condom. Happened to me recently, but not that often. I think this is more likely if your not at 100% wood, as it is then tougher to get the condom on fully. Then, if you get full wood during the action you have room for problems.

The lady, if well lubed can generate enough suction to pull the cover off, under these circumstances, especially if you have gone soft after finishing.

A bit of lube on the head, for you, can improve sensation, but be careful to not get lube elsewhere on you.

this has happened with me quite a few times, with either the condom being stuck inside after he pulls out, or nearly coming off as he pulls out. because i am the one who chooses the condoms, and i am very meticulous about ensuring proper fit, improper condom size has never been the cause. neither can it be blamed on the vaginal contractions which come with orgasm, as i am not very orgasmic. fortunately there has never been any spillage or lost condoms in these situations...the condom is always fully intact and in the proper position, it's exactly as if my hand were placed on the tip of the condom and pulling it firmly as he is backing away. it is the tightness, utterly beyond my direct control, which causes this. and as a couple of others have noted, there are definitely downsides to being so snug. this is only one of many.

I didn't cum and was still hard as a rock when I went to pull out. And Yup, just like some of you have mentioned, the condom was hard to get out of her, it was stretching out until it finally snapped out.  Looks like it hurts her and I kinda don't want that to happen.does it hurt you ladies who this happens to every now and then?

a little pain is not necessarily a bad thing. i'm no masochist, but i look at the pain of vigorous sexual intercourse as something akin to the high an athlete gets in the midst of a really intense, physically challenging game. yeah, you are getting beat the heck up, but in the moment you don't feel a thing because you're so focused on the goal. for the athlete it's the win, and for me during sex it's about pleasing my partner to the absolute best of my abilities...just providing (an in doing so, having) an awesome sexual experience.

so the answer to your question is, yes it hurts, but i won't know that until early the next morning, lol.