How to ask awkward questions?

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I'm dating a guy and I'm at the stage where I really want to know about his relationship history. I find it difficult to ask direct questions about people I prefer them to volunteer the information. I often prepare a question that I'm going to ask but get really nervous and shake and sometimes after hours of planning never get the courage to ask the question. But I understand he isn't going to give me a lecture on his relationship history so I'll have to ask him questions I want answers to.

I have twice tried to hint at what I want to know. An example of when I tried this is:
Him: What size are your ..... ? Size 5?
Me: No they're size 2
Him: Compared with my hand they're plenty big enough, they look like they should be called a 5 to me
Me: How many of these have you seen to make that kind of comparison?

He made an embarrassed giggle, was quiet for a while and then started a different conversation.

I get the impression he'd rather avoid the topic and I'm really embarrassed to talk about relationship and sex topics so I don't know if I can find out what I want to know.
Any advice on when, how, where would be gratefully received.

Could this type of conversation be done via email or would it sound a bit like a questionnaire and be more difficult for him to answer?

How to ask awkward questions?

Well, all I can say is, don't ask awkward questions.

Sometimes I find emailing/texting easier. The last guy I was with I was able to find out what I wanted to know by texting him. "When was the last time you had sex? How long did your last serious relationship last?, Why did it end"? I dont think I could have asked those face to face but really wanted the answers. I think as long as you don't ask too many questions at once it won't seem like a questionnaire.

Strange that he got all giggly about it. It something normal to ask, in my eyes.
Me and me ex could easily talk about these things

Agree that anything like that is best asked via text/message. What I've also found helps has been to ask if he minds if I ask a question, no pressure to answer. If he's ok to answer a question then I ask it. If he changes the subject then I know it's not a good question to ask. But the main thing I've found is to give him time to think about it, as it often takes him a long time to think about the question, and just be patient, as he often goes quiet when he thinks about how he wants to answer something.

I'm kind of confused... did you ask him what size his balls were? There's a sizing chart for that now??

What question are you even trying to ask him? I'm so lost..

Edit; I get it, you meant boobs..... I'm leaving the above intact as proof that I can be an idiot sometimes.
That's a pretty open ended question. Thanks to the internet most guys have seen hundreds if not thousands of breasts. I could probably see a few hundred in the next 10 minutes if I wanted to... kinda makes you wonder what life would be like if that weren't the case.

Anyway, I would suggest trying texting or whatever until you're comfortable in person I suppose.

Sorry for the confusing post I just didnt want to give too much personal information but yes I meant boobs.

Thanks for your replies I took your advice and emailed him and it turns out that was the right thing to do because he replied with the answers. He confirmed what I though and why he was too embarrassed to tell the truth when I joked/hinted about his experience. He had a girlfriend for week or so, at uni years ago and they only kissed, so we are exploring new things together which is kind of nice, kind of scary.

Thanks again.