Worried about comfort while penetrating with a tight foreskin...

Please be relaxed about the whole thing!  An anxious mind = unsatisfactory sex!!  Sex is completely possible with your foreskin just the way it is!  No hurting, no discomfort!!!  Of course you are acting differently when penetrating, from masturbating.  But, your penis will NOT react differently in any way whatsoever!  Just find the right partner, get the permissions bit sorted out (i.e. you both agree / partner gives permission) for what you are doing.

I had a very tight foreskin, and, like you, I was only able to retract it just a little bit.  I eventually stretched the skin so that eventually I was able to completely reveal the glans/head.  If you want to try this look up how to do this online.  You should avoid exposing the head of the penis to ANY skin cream / lotions / or skin repair ointments that are oil based (i.e. all of them).  If you want to try, simply draw (very gently at first) the foreskin forward as far as it will go in front of the shaft / head of the penis, and, let it relax back again before repeating.  Start doing this for a minute at first (say, stretching 5 to 10 times) - IF you experience pain, STOP immediately!

Do this 2 or 3 times a week.  The second week, add another minute, 3 times a week - and build up so you are doing 12 to 15 minutes, regularly, at least once or twice a week.  Don't be tempted to use baby lotion / oil / gel or oil based lubes - as you will need to continue this practice over an extended period of months, or even years, if you eventually want to expose the entire head.

Once this is established on a regular basis, (very slowly) the head of your penis will comfortably be able to be exposed.  AT ANY POINT in your exercise regime, if what you are doing cases pain - STOP, and check for other foreskin stretching techniques online, and try those.  BE WARNED, you may get to the point where you can expose some of the head and you want to try masturbating with it retracted to where you can reach.  Your penis head WILL enlarge as you become more stimulated, AND, it may become very painful / impossible to even try to pull it back over the head of the penis.  You get round this by trying to masturbate for a very short period of time, then, fully covering the head of your penis with the foreskin, and then, learning how far, in terms of time / amount of stimulation you can actually get to, BEFORE you get any pain, or the foreskin refuses to retract.  Here, the 'thumb squeeze technique' comes in very useful if you need to loose your erection very quickly (look it up online, and other techniques too).

THE ESSENTIAL is, you find how how to be squeaky clean in terms of the hygiene of the glands / head of the penis.  Obviously, you cannot properly clean the head of the penis if you cannot retract the foreskin!  This will unlikely be a problem unless you intend never to use a condom!  Or, you become adventurous and have several different sex partners. 

In terms of having a healthy penis, it is not a good idea to stick with having a really tight foreskin - as you will never get to the point of having a hygienically healthy penis.  YOU can either work on this as I suggest above in terms of stretching the foreskin of your penis, or, seek medical expertise and go to a GP and get it sorted.  Try stretching first if you like, but if you get in a position where you are experiencing too much pain regularly, you MUST seek medical advice!

In the mean time, even AS YOU ARE (your foreskin I mean), simply, sex will be comfortable, and obviously, in every way possible.  In terms of getting your penis used to different amounts of 'being exercised' vary the length of time you masturbate, slow down, try pulling the skin down the shaft, slightly more each time.  Again, stop if you get too much pain.  Develop a sense, not so much that you are doing some form of gym excercise routine, but are experimenting with different types of self-pleasuring with the penis - learn what works for you.  But, sex that is enjoyable for both you and your partner comes from being able to last longer with an erection, before you ejaculate.  This itself comes from you practicing self-pleasuring on your own - and building the amount of time you have with an erection, before you conclude in what ever way (stop, or ejaculate) you wish.  But you should try stopping before you ejaculate, some times - and see what that feels like.  You could do worse that looking up what some people call 'kegels for men' online, and try a few of these tips.

ULTIMATELY, relax - enjoy, being on your own with your erection, and you will likely feel much more relaxed than you are now, once you are with a partner ...... GOOD LUCK ........

Thanks for the reply - as you have exactly the same problem I had with a tight penis I hope you get some benefit from the detail I have provided.  You can let me know how you are getting on in  2 or 3 months time - remember it is all about learning to be relaxed and comfortable with handling your penis when you on your own, then you are more likely to be relaxed with a partner at a future date.

*If you have any particular doubts to resolve, or you have problems making progress let me know?