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Couldn't ejaculate while having sex? (Foreskin prob?)

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To cut a long story short, I recently met up with this guy after texting and chatting with him on IM. He's really nice, and we eventually get it on, mostly with foreplay and oral sex and even so, I can feel we're not that experienced especially that being my first time, and that was his second.

The strange thing was, after almost two hours of jacking each other and sucking each other off, I couldn't ejaculate. The 'horniness' wasn't there, not because he wasn't attractive (I think it doesn't matter). My foreskin covers my entire head and it does not slid down at all when I wank alone at home. However, when he jacked me, he pulled my foreskin down, exposing my head, and continues doing what he thought would be pleasureable for me.

But it wasn't that pleasureable for some reason, and I thought it may be due to my foreskin being pulled down too much for the first time, that I wasn't used to it at all. I eventually didn't cum, and he didn't either, because he wanted me to cum first. :/ (which makes me feel guilty, and very embarrassed)

Right now as I type, while my dick's flacid, when I pull or stretch my foreskin I feel a little pain. Is this normal? I have only recently known that I have to actually pull back my foreskin to clean the head off smegma (blame it on the lack of education as a kid) and I only clean it occasionally, which means I don't pull down my foreskin very often because of the stinging/pain sensation when I pull it down.

What are you thoughts?
 
A lot of guys I've been with who don't have experience with a foreskin think that vigorously jacking it up and down must feel good, when instead, it feel uncomfortable and rough. It's mostly in the head when a guy jacks me off and you have to let the foreskin roll over the head instead of just pulling it up and down like a pump.

So I don't think it's you at all. Just let him know next time how to make you feel good.
 
The guy I'm with is uncut like me, so I imagine it'd be the same to the both of us. Looks like this is not the case.

I probably wasn't relaxed, what with us getting it on, and his mum is in two rooms away. I was so focused on wanting it to be nice for the both of us that I didn't speak out my mind. I probably should have.

So it isn't a foreskin prob? Because I'm still having a tiny, tiny pain stretching my foreskin - probably have to give it more rest.
 
The foreskin is supposed to be able to retract without pain by the time you are about 10 years when the forsekin should be completely detached from the glans. Cleaning the penis is important to prevent any kind of infection. Also in penetration the forskin retracts outomatically.

If it is painful when the foreskin retracts, then you should see a doctor. It can eighet be treated or if you continue to have problems, then the doctor may recommend circumcision.

P.S. How old are you?
 
I don't understand if you are feeling pain only now, following the over enthusiastic jacking or if you have always felt discomfort or pain when the foreskin is pulled back all the way?
 
Maybe it is just air sensitivity. Since you're covered all the time when the head is exposed it is sensitive to the air and feels uncomfortable. I had a BF a long time ago that was like this. Clean regularly and gradually expose the head to the air every so often to get accustomed. Cutting off your foreskin is a bad answer IMO.
 
I'm 19. As I have mentioned, my foreskin does not slid down to expose the head 'easily', because it's certainly far from easy, without encountering some slight stinging sensation.

I have indeed seen a doctor who said that I need to pull it back gradually to get used to it or something, saying it's normal to feel a stinging sensation.

Adidasluvr, I certainly wouldn't imagine problems if there aren't. My foreskin does not retract easily, so I guess I have to work on it.

3nipples, I only felt the pain only now, after our 'session'.

cityboy, that's interesting to know. Yep, guess I'll do the same since it's like the only possible solution.
 
yeah, doctors usually suggest that young boys begin pulling it back carefully and washing the head. I believe that this is not only hygenic, but also because they want the boy to start stretching his foreskin. Try stretching it back a little when you go to pee or when you wash it. Gradually, it should become more flexible. Your doctor can probably also prescribe some steroid creams to help it out.
 
The foreskin is supposed to be able to retract without pain by the time you are about 10 years when the forsekin should be completely detached from the glans....

Some authors stated a range starting at 5 yeras old, as always it's different from person to person. In my case, since i remember i can pull it back, i have never had any problem with it.

And the pain after all? probably he pulled too much, if this is the case the pain must be gone in a day or two. And again, in my experience i have found guys who like to be hard pulled (like me) and guys who like a short motion becuse they say it hurts, last ones are almost always cut-at-birth guys, the lack of foreskin in some cases don't allow too much room to pull like my last exbf.
 
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