I have to say that's not something that I've personally tried, but then I'm a research monster and I'll give what that's turned up regarding things like that.
Having multiple orgasms in a row for a guy is possibly, but actually requires training of sorts, so nothing your average Joe could likely handle. It's possible through basically tricking your mind into believing you've ejaculated, without ejaculating, because once fully ejaculated the testis become over sensitive and the system will go into refractory time. So, if you're looking for a guy to blow his load multiple times in very rapid succession, the only way to get that is through the use of half orgasms. However, these won't work for long because once the testis are spent, the guy is at best going to keep a slight hard on if light stimulus is continually applied. For most guys to maintain a continual hard on through something like that, it's going to likely take drugs to pull it off and even that's going to have it's limits.
Alright, for sensations, over-stimulation is very painful for men, largely because it takes place in multiple areas. There's the normal surface sensitivity problems which shouldn't be real hard to translate for women because to my knowledge you have that same issue. After that, our testis begin hurting when we try to use them while their spent, it's very akin to muscle cramping to my knowledge, a muted ache in general and a sharp stabbing pain when in use, but this only occurs when one tried to ejaculate with nothing left. Likely the last one to really come into effect is the throbbing pain from the swelling; while the penis is made to swell, after it's been swollen for so long (average being after a few hours of being hard), it starts to hurt from blood pressure and continual stress on the skin. Even with some training in handling pain, this is all likely enough to keep a guy from being able to keep it up, though the relief from losing the hard on is likely to make stimulation enjoyable again and will probably get the guy stuck at a point where he's half hard until he recovers some.
As for the half orgasms, I don't actually know a better name for them but that'll work for now, it's not nearly as powerful as a full orgasm, however the refractory time is dramatically shorter. There's usually only a little time where the guy is hypersensitive, if I had to estimate, between ten seconds and a minute, however before the refractory time has started it's very possible for him to be pushed into a full orgasm and leave him with the full after effects. During these short refractory times the hypersensitivity is dramatically less then after a full orgasm, so it's easy to "mingle pleasure and pain" during this time without any real bad effects. Beyond that, it's fairly normal, though the follow up full orgasm tends to be stronger for the same reason orgasm denial makes the break into it stronger.
Likely one of the biggest things to keep in mind is not just the emotional/mental state of the character, but also the physical reserves; an eighteen year old might have a recovery time of a few seconds allowing him to never skip a beat the first time or two if he's really got some stamina, but by the four or fifth without a break, he'll be agonized because he body can't deal with it.
Though, I recommend following Apollo's suggestion about asking a BDSM forum, they'll likely have a far better answer then the one I've given and likely have actual experience to speak of. I'd also like to say, I blame BronxWench and Jem for this.