Can A Girl Be Asked A Question This Early?

Hi all,

Here's my situation - I'm 41 years old and single. Ive dated intermittently over the years., but never a serious girlfriend. Part of what contributed to my situation was taking care of a ill relative for a majority of my 20's. I started to date a woman later on - we made out a few times but no sex. I got friendzoned by her due to in retrospect me acting too much like a simp.

After that I got caught up with the healthcare of said relative. Then I got hit head by a driver high on drugs walking across the street. I broke both legs and arm, got metal plates and rods installed. But I had an infection and I had to take a new anti-biotic medication. Only downside I was warned would be my testicular skin receding/shrinking.

I took the medication because otherwise my leg would be cut off. It worked but it did damage where my penile skin receded. My penis size went from 5 inches to about 4. At the time though I got focused back on handling the affairs of ill relative full time. I had somebody help while I was recovering and learning how to walk.

My relatives health took a turn for the worse two years later and they passed. The expenses of healthcare and other things left me with a small budget. Due to intense grief I decided to move out of the city I lived in to a different state. For the next couple of years I went through major struggles - a brief period of homelessness, people who exploited my situation to their benefit. But in the end I was able to get back on my two feet and live on my own. I had interest from different women over the years of struggling which i ignored since I was at rock bottom financially

But now since Im in a better situation, I was focused on getting my penis situation treated with a new procedure which helps bring the penile skin out of being receded. But I need to save money for travel since I live in another city and it is in san francisco. But the ironic part is Ive gotten interest from multiple girls. One was forward enough to give me her number. So with my schedule being busy Im ironing out when to meet up with her.

My question is this - I cant confess that Im a virgin given my age. But at the same time, knowing my penis is presently small, I need a girl who has a small vagina to be able to have sex. Cause I know a woman with a big vagina wont give me the time of day after finding out Im packing a shrimp di-k. I dont want to waste going on a bunch of dates then get to sex only to be rejected for my size.

One of my strategies is if it gets physical, to do oral sex and find out the vagina size. If the vagina is big, get her off, then bounce. And send a text telling her Im not physically compatible with her and delete the number. 2nd option is waiting until I have kissed her, and then asking if she has a small vagina. I get how awkward the question is but is it also too early to ask even if minor physical contact is made? I much rather ask ahead of time over getting to oral seeing its big then finishing her off and nicely nexting her. Just curious on your opinions