About breaking your virginity

[Tinaaaaa]

Hello, I am a 27 year old virgin. Due to personal reasons which are very intense and hurtful, I have not been able to get into a relationship, hence I have not been able to have sex. People get very surprised by that but after 22-23, guys did not want to sleep with me because they felt pressured. Cut to today.

I met someone a while ago. Because of his travels, we will be meeting after two months. We have done stuff, but we havent done the 'deed' if you know what I mean. We plan to do it when he visits after two months.

The thing is, that he is 3 fingers thick, and I have only been able to pleasure myself with two fingers down there. I have been trying to put in three fingers but everytime I do, it burns and it hurts. I want to be ready when he comes but whenever i try to put a third finger in, there is so much pain and the burning lasts for a long time.

I am worried that this what will happen when he comes and we wont be able to do it because of the pain. I even tried a thick vibrator and other tools, but nothing is going in there. I desperately need help with this and I want to know if I should go see a doctor or I should wait for him to do the deed. Please help me out with this

[Amanda B]

Hi Tinaaaaa,

The first thing I'd like to know is where this three-finger measurement is coming from. Is this something you've measured yourself, during the "other stuff" you mentioned? Or has he just told you he is "3 fingers thick"? It's pretty common for people to overestimate when it comes to size.

It sounds like there has been some stress and anxiety around this experience. When you say "doing the deed", do you mean vaginal intercourse? It's completely natural to feel anxiety before new experiences, especially something that can be as intimate as this. Please make sure to not pressure or force anything, as it can cause that pain and burning to become even worse. It's important to be aroused before trying any penetration. It can be helpful to envision fantasies, explore touch around your body, including the external part of the genitals, or whatever works for you. Try to relax, take some deep breaths, and communicate with your partner about what feels good and what doesn't feel so good. When you feel like you're happily aroused but still experiencing some difficulty, lube is always helpful to create a safer, more pleasurable experience for everyone involved.

Lastly, I am sensing some urgency around wanting to "do the deed". Is this something you're genuinely excited about? How do you feel towards this person you've been talking to? There is plenty of pleasure to be had with many forms of sexual activities, and it's important to enthusiastically consent to each one.

[Amanda B]

P.S. we disapproved the other thread you had posted as it had the same content as this question.

[Tinaaaaa]

Hi Amanda,

Thank you for replying, somehow it didnt show up in my notifications which is why I decided to post the other thread that was discarded.

Getting back to the points you have mentioned, yes I meant having vaginal sex when said 'doing the deed'.

We have done oral and hand stuff with each other which is why I have an idea of his size. Although, he might not be fully three fingers thick, girth wise, but he is definitely bigger than two fingers.

I am really excited to do this with him, so there is no pressure or urgency and he is a very respectful person. But the thought that it might hurt me because I have only been able to insert two fingers down there is what concerns me. What if we have to stop mid way because it hurts?

I want things to go perfectly

[Carly]

Hey Tinaaaa -- I want to gently challenge you saying there's no pressure on the situation. You also said you want things to go perfectly, and your thread is about trying to make sure you have what you consider a perfect experience. Do you see where I'm coming from here? Perhaps the pressure is not coming from him, but from you on yourself?

To move away from the "getting ready" piece of this question a bit -- have you thought about what would happen or how you would feel if, for example, you tried to have sex and it were uncomfortable?