I cannot believe I haven't had sex yet!

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In her case it wasn't completely unvoluntary because if you read the whole topic, OP said that she refused a proposal to have sex because she didn't feel ready.
(by reading this topic, I manage to conceptualize that the context was not favorable to her).

Now, she is.

PS: that said, I have the same opinion as everyone else that it is probably not advisable to date someone who has just been in jail.

Most of society, or just a portion with unrealistic understandings of the struggles other people encounter?

Has anyone mentioned contraception yet?

You can get pregnant the first time you have sex, or any other time. What would you do if you got pregnant?

But what if we were to start with just oral sex without penetration then pregnancy wouldn't be possible

If I somehow did fall pregnant I would either have an abortion or go through the pregnancy anyway and learn how to take care of a baby

Same for STDs.

Prisons can be wild.

Good point.

People can still get STDs through oral sex even though you can’t get pregnant that way.

Honestly I think Jerry has sex in mind for when he comes to see me because in his letter he wrote I can't wait to hug you and stuff which might mean sex

But maybe not

It almost certainly means sex. He could be trying to romance you in order to get sex. I’d just ditch Jerry right now if I were you.

It would be better to make a careful plan for contraception well before having any kind of sex. You could start with oral sex and get carried away in the heat of the moment and move to intercourse before you know it.

Just because mentally or emotionally you don't think you will get pregnant, anyone with a female body will get pregnant regardless of what their brain thinks. Please believe me and take care.

And having an abortion or a baby will change your life forever, they are huge steps to take.

I know

I think that is part of why I have held off on sex for SO long!

Honestly IDK if I'm ready for a baby but I also know that I am desiring intimacy and true connection

You don’t just need to worry about pregnancy. There is also the risk of sexually transmitted diseases.

Which is why if I ever have sex I might want to start with being fully-clothed before getting naked

The best thing to stop both pregnancy and STD is for him to wear a condom, and not one he's kept in his wallet for years. A brand new condom he has just bought.

Do you think Jerry is willing to wear a condom? Can you ask him? Have you talked to him about contraception?

I know it's not romantic but it's very important for your own health.

I think Jerry should be ditched altogether. People who are fresh out of prison aren’t in any position to date.

Someone more suitable will come along eventually.

I can't disagree with you there.

We aren't at that point in our relationship yet but once we get to the point of being intimate I will discuss birth control and condoms with him