TLDR; I have been in an open relationship with my boyfriend for almost a year, which I initiated. However, after a couple of experiences where I felt insecure and unloved, I've been struggling with our intimacy and communication. Recently, I broke up with him after feeling like a second choice due to his interest in others. He expressed regret and wants to improve. I'm conflicted about staying together but worry about feeling hurt again. How should I handle this moving forward?

Me (FTM23) and my boyfriend (M22) have been seeing each other for almost a year now. The relationship has been open since the start. I was the one who asked for it to be opened. But, we haven't had many experiences of sleeping with others. The two situations where we slept with other people will be talked about later in this thread. But, both situations have made me feel insecure and unloved.

We have rules for the open relationship. One of the rules is that we are the primary relationship, and most of our attention should be focused on each other, rather than the people we hook up with. For example: If we are wanting to hook up with an individual or couple more than once a week, we must spend more time with each other so we aren't spending more time with the hookup. The rule is kind of vague, but has implications. Another rule is that we are to ask each other if we can hook up with a person and to not proceed until permission is given. 

The first time we hooked up with someone, it was together. I have this really sexy friend and she was interested in a threesome with us. The experience started off really fun, we were touching each other and all involved. My boyfriend was rock hard for her, but the second he looked at me he would go soft, and have to go back to her. It made me feel ugly and disgusting at the moment. I tried rationalizing it- usually he only has one or two rounds in him, and he was on his second round. I started cramping violently, and started bleeding a lot from my hooha. I was still trying to be involved in any way but I soaked through my tampon and blood got all over my legs so I went to shower and clean up after they stopped having sex. While in the shower they started fucking again and I came into the room mid fuck and I was admittedly sad. I didn't get penetrated at all that night. I still tried to be involved but I bled through my next tampon. I went to the bathroom again and my IUD fell out. I was bleeding so much, I was scared and crying. I was contemplating going to the emergency room. My boyfriend came in checked on me for a little bit, and after I came back to the bedroom, they fucked again as I watched and wanted to cry more. They were fucking all night long when he usually only fucks me for 30 minutes tops. The bleeding slowed down after I removed my IUD, but both her and my boyfriend showed little to no concern and kept going at it. At one point during the night he told me I need to learn how to give a good blowjob because my friend does it better.

Since then, my boyfriend has been begging me to invite her over again, and has been talking about how big her ass is, how grippy she is, how nice her tits are, and overall how attractive she is. Which is true, she is very beautiful. She is now in a monogamous relationship so we are respecting that. The other day he commented "I cant wait for her to be single again so I can fuck the shit out of her." Which I wouldn't be opposed to. I would love to mess around with her again, but the issue is my boyfriend never says these sorts of things to me. The most I ever get is a "I want you" like Tow mater. Which he has said to his platonic friends before in a joking manner. I have brought up how insecure I feel. Compare myself to her, and other people. I've told him I feel fat, and ugly, that I need affirmation. All I get is a "stop talking bad about yourself. You're my Pookie." Which intensifies my insecurities. Our sex life has also become less and less intense and passionate. Foreplay will last for a minute, and he is ready to go- will fully focus on the TV and not me. He does let me orgasm most of the time, but will finish right away and be done, sometimes he won't do any aftercare and jump up and put his clothing back on and start watching Instagram reels. I'm the one who initiates sex the most and either he will flat out decline me, say he is too tired or not in the mood. Or, he will reluctantly agree and seem uninterested while we fuck. He will almost never fuck me more than 2 times a week, and I don't want to be too pushy so I have tried to not complain too much.

Recently he has been talking about femboys, and his interest in hooking up with one. One of my old fuck buddies is in a relationship with a femboy, so we met up a few times to hang out and to feel out if we would want to do a foursome. Ever since the first hang out my boyfriend would constantly ask to have them over so he can fuck them. Tension was building in between the group and Hurricane Helene hit our area really hard. Power was out. They had a small electric generator and fans, they invited us over, so we spent the night. The experience was fun.  But my vibrator died before I finished so I half jokingly told my boyfriend he owes me an O later. We slept at their house that day.

 My boyfriend was being sweet and teasing me more than usual the next day so I thought perhaps I was going to have some fun with him. My boyfriend's house also got power back before me and the couple, so we ALL went to his house. He still lives with his family still, and siblings so it was a house full of people. We all hung out that night. I pushed for intimacy with my boyfriend in his room right before we went to sleep but he declined. He told me to wait until my power comes back on so we can do it at my house. (which was estimated to be at least 3 days before my power comes on.) 

All of us were still at his house the next night. Just all hanging out, but I had to go to work that night. I left for work and my boyfriend texted me at midnight asking if my grandmother usually keeps our house unlocked. He then “joked” about sneaking into my room to fuck the femboy friend. I told him no, that I wanted intimacy with him and that I was upset that he proposed the idea of having a night with my friend after declining me the night before. He then tried to change his story and say they were all gonna wait until I get off work, and then we can go to my house together. I  called him out on twisting the original idea to make me feel included. I still declined the proposal. I told him I was upset that he wasn't even thinking about intimacy with me, and that he was just thinking about the femboy. I told him he doesn't ever want to fuck me anymore and it was making me feel shitty.

At 4 am he messages me again. He says the femboy and his partner invited him to have a threesome in the backyard of his house. I was in emotional turmoil as soon as I read this. I reluctantly said “yeah I guess” he wanted to make sure, and I told him “You've been wanting to be inside this friend again so go ahead and enjoy. You've been begging me to fuck him all night.”  He said I'll have sex with you in the morning when you get back from work. I declined the offer. I told him he was being hypocritical with the boundaries he set with me the other night JUST to fuck the friend and that the sex with me would be more of a chore for him than exciting. 

He texted me an hour later at 5am asking me to sleep with him again after work. I declined again. He told me that he decided not to do anything with them because of how upset I was. He asked me why I was upset and this is the message I sent him. “it doesn’t really matter that you didn’t do it or did do it. It's the fact that you are doing everything you can do to have sex with (femboy) again. Staying up all night, asking to go to my house while I'm not there and at work, going outside to fuck, when you told me to wait for my power to get back on so we can do stuff when I've been wanting to be sexual with you. 

It’s almost like I'm an always available option so you don’t have the need or want to fuck me. It’s like you don’t even want to fuck me half of the time because it’s too much work, I take too long to cum, I'm not the most pleasurable hole to stick your dick into, makes you sore, or you’re too tired. 

But you’ll twist your own “boundaries” you set with me just to fuck someone else after I've told you multiple times about how I feel when you decline my advances and not being in the mood. You obviously WANT sex and you’re in the mood. You just don’t want to have sex with me. You didn’t come up with any plans or ideas to have fun with me. You’re just thinking about (femboys)  ass right now. I feel undesirable and unwanted … And I hate having you sigh and seem uninterested when I start touching you. It honestly just fucking hurts.

As someone you say you love and are a partner with, clearly you don’t really show sexual compatibility with me and it sucks.  I don't feel like a priority at all. And clearly I'm not. Honestly, I do not know if I can trust how you feel for me. If I was acting the same way to other people in our open relationship and towards you I'm sure you’d also be feeling the same way.”

He ignores the majority of my message (I talked about the bleeding out situation, and the never complimenting me as well)  He repeats that he doesn't want to do anything in his room, that he is paranoid that his family will hear us getting busy, and he doesn't want his parents to know that we are together. (and I'm sure you readers remember, but I want to emphasize that he was willing to have sex with me in his room only if he got to have sex with the femboy.)  I responded very passively aggressively. 

“Does not stop you from thinking with your dick when a femboy is there. I guess you prefer them listening to that.”

I broke up with him. 

My emotions were crazy and I was crying at work. I left and went to my unpowered home and cried even more. He kept apologizing and kept begging me to come back. I didn't come back until later that day, and I tried my best to sleep on their couch but his family kept me up. I went to his room eventually and we slept in the same bed. I was too tired to care. I got up to leave for work and couldn't even look at him. He waited at the door expecting a "I love you" or a kiss, but I only hugged him, and he broke down and started crying and saying I'm sorry a few times. He has never really been one to be emotional, talk about his emotions let alone cry, so it made me feel awful and conflicted. I started crying in the car on my way to work.

We had an exchange of messages that night while I was at work. To sum things up I told him I didn't know if I wanted to have sex with him anymore because I felt insecure and unloved. I also shouldn't depend on him to feel good about myself.  I'm scared of falling into a codependent relationship like my last one. I told him my self negative dialogue has been leeching into how I perceive the relationship and that my trust issues started flaring up. I haven't healed completely from my last relationship and it's taking a toll on us.  Maybe I need to work on myself and I am not ready for a relationship. He just kept saying that he loved me, and that I was the best partner he ever had and was sorry. He told me he hasn't been a good partner and will do anything to make things better. He suggested only having sex with me and nobody else moving forward. He didn't want me to break up and leave him. He said he loved me more than life itself and he would be miserable without me.

I came back after work back to his place (still no power at my place) and as soon as I got to his room he latched onto me and sobbed. He kept saying he was sorry. That he didn't mean to make me feel unloved. I started crying too. I was  imagining my life without him in the picture and it was a hard one to think of. To be fair besides these issues in the post, he is perfect, The healthiest relationship I have ever been in. I'm willing to give him another shot but I don't feel like I'm mentally prepared if this happens again. I want to keep it open. I just don't want him to get "comfortable" and make me feel like a second choice again.

I have been very conflicted. I want to continue a relationship with him, but don't know if I'm willing to feel this much hurt again. OR how we should handle things moving forward. Hell, does reddit think I was overreacting to this situation or could have handled it better? What do you think I should do? Any advice or criticism on how the situation was handled would be ideal.