Obligatory forgive my formatting mistakes, currently on mobile.

Some background:
My (33F) ex-boyfriend and I dated for about 6 months. He was my a lot of my firsts, but we never had PIV sex. It’s important to mention that I was raised in a conservative Catholic house, with a strong emphasis on purity culture; I believe this impacted my ability to have PIV sex, as I broke down and had panic attacks prior to penetration. Throughout most of our relationship, my ex-boyfriend was very understanding and introduced me to sexual acts slowly.

Now my ex-boyfriend and I have been having phone sex on and off for the better part of a year. We often role-play, send pictures, and sext each other, with small breaks when we were seeing other people.

My ex-boyfriend has hinted that he would like to meet up to hook up when we are both free.
Personally, I feel very conflicted. I feel very insecure about being a virgin at my age, and I sometimes worry ill never meet someone who’ll want to be in a relationship with someone with as little experience as me.
I think my ex wouldn’t be a terrible first partner, as we are familiar with each other’s kinks, likes, and dislikes. However, my feelings for him are…complicated. I’m worried that I’ll get attached to him again, and if he breaks it off I could have my heart broken all over again.

Sorry if this rambling or confusing. I guess I’d like to know if it’s possible to hook up with an ex, and not have it turn out badly? Should I hook up with him, just to get over my insecurity about being a virgin? How do I handle my feelings around sex with him, especially if I start to get attached again?

2 comments
  1. Honestly, if you are a virgin at 33 it is safe to say you have trouble opening up and being comfortable. If you feel that comfort with your ex, then use that. Otherwise you’ll be able to talk yourself out of it forever. I think this is one of those times where you have to stop trying to analyze every potential outcome and just see what happens. Good luck op. Whatever you decide I hope it’s what you want.

  2. If you think it’s likely to get attached, you probably shouldn’t do it. Unless he’s open to getting back together. Ex-sex is a dangerous game and can churn up a lot of feelings that are unpredictable, and you might not be prepared.

Leave a Reply
You May Also Like