He slept with someone- I'm having a hard time

My boyfriend and I recently broke up after nearly 5 years because he was having a hard time remaining monogamous. Since then we have been seeing each other again without any clear guidelines as to what it is. Last night he had sex with someone for the first time. I was somewhat mentally prepared for it but I'm still having a hard time processing it. It doesn't feel like jealousy as much as sadness, a feeling that the bond we shared is broken and can't be fixed. Does anyone have some advice as to getting passed this. It's someone he met online and said it was just a friend. He also took a bottom position which is something I had really wished he would share with me only. I just feel broken

Are you asking for advice on how to move past this with the intention of staying broken up/reshaping your relationship into friendship only? Or, advice on how to move past it with the intention of reshaping your relationship into an open or poly relationship? Because those are two very different things...

In the event it's the first, I'd suggest getting some breathing room. Go little/no contact for a short while to give yourself a chance to heal. Then, you can slowly work on reshaping your relationship into a friendship only.

In the event it's the latter, I'd suggest that you first ask yourself WHY you want an open relationship? If it's just because that's the only way you can be with your boyfriend and you don't want to lose him, I'd still recommend going little/no contact for a while. Long enough to heal and give yourself time to really consider whether being with him is worth the pain you're feeling right now. Consenting to something you really don't want is ripe ground for pain, resentment, and unhappiness. There are plenty of monogamous men you could choose instead.

If I'm reading your post incorrectly and you really are excited about the prospect of an open relationship and just want advice on working through your insecurities and jealousies, please ask

Good luck in whatever you decide!

ETA: I apolgoize. I should have re-read your previous post. I'm leaving what I said up because I do still think it applies. I don't believe anyone should be in an open relationship in order to "keep" the relationship. Resentments will just build and it will erode the relationship. I guarantee there are men out there who would love to be monogamous with you. That said, it is possible to work through the jealousies and insecurities. Like AutumnLeaves said, treating yourselving lovingly & gently helps...so does deconstructing your jealousy to get to the core fears/insecurities behind it so you can work on those. I also find it helpful to look at the relationship (excluding the openness part). Is my partner loving and affirming? Are my needs getting met? If the answer is yes, or mostly, then tweaking a few things and working on myself helps. IF the answer is no or mostly not, then maybe this isn't the right partner for me.

You're allowed to feel your feelings. I think bad feelings in that situation are perfectly normal to have.

I usually process things by going "why why why" like a curious child, trying to get to the heart of what's really bothering me instead of dwelling on the bad feels. If I can figure out where my jealousy is coming from (fear of loss, fear of replacement, me-too), I can figure out what will help me stop feeling that way. I also try to engage in self-love instead of moping. I moped through my first major jealousy wibbles and that obsessing over my pain didn't help.

If I remember right, you're still dating you ex-bf? In good news, your bond isn't any more broken than you decide it is. I'd guess that your jealousy is rooted in insecurity (not feeling special enough). Maybe you should focus on finding something he can do for you to make you feel special and more secure and bonded right now.

And if he's not willing to do that, you should DTMFA because you aren't going to be able to "handle" this if he's not willing to meet you half way. You clearly have some security needs. This might not be the relationship, or relationship model for you. I wouldn't give up YET, but it's something to think about.

I am confused. being open is not something I've ever done. I'm still in love with him and I do believe He's in love with me. Every monogamous relationship I've been in has fizzed out and most of the time I ended up leaving to be able to be intimate with someone else...Serial monogamist.

So We've decided to just see each other with no strings or rules right now, until Experience can show me what I want. With him I have very little need for someone else, but I've hooked up with others and it hasn't changed the way I feel about him. I've only know one thing and I don;t know that I would have considered it if he didn't need it but that doesn't mean that it may not be right for me.

I don;t feel jealous but I feel slightly possessive and insecure and a little like I just found out Santa clause isn't real. If anyone else had ever slept whit another man I'd be done with it. However it's different with him I'm still in love with him and I recognize that he hasn't seen sex as sacred like I have and maybe that is something that needs to change about me.

You don't need to change anything about you, except maybe your belief that you have to be what *he* wants instead of being what *you* want. It's fine to choose to change something about yourself in order to make a relationship work better--if it's YOUR choice and not something you feel that you have no choice about.

It sounds like you don't think you have a choice in this case. You either deal with him having sex with others while also having sex with you, or you lose him.

That is a choice. You could choose your comfort and emotional well-being over his desire to include you as one of his multiple partners. Losing him would hurt you, I get that, but the current situation is hurting you as well.

If you do consciously choose to continue seeing him under the circumstances, where "consciously" means recognizing that it is YOUR choice, not his, and that you have other options, you might ask him whether he would be willing to help you feel more comfortable about it by reserving something for just you and him. For example, you say you wish he wouldn't bottom for anyone other than you; if that's something important to you, ask him if he would be willing to keep bottoming exclusively something he does with you. (I see that he's already bottomed for someone else, but I mean going forward.)

You can't control what--or who--he does, but you do have control over what you are willing to accept and how you respond to his actions.

I agree with KC43 that *you* don't have to change how *you* feel about something - unless of course, those feelings genuinely aren't working for the person you want to be.

I think you might want to work on applying your definitions or meaning about things/activities to other people. For instance, you mention sex being sacred to you. What does that mean? Does someone who also feels that sex is sacred, but in a *different* way than you do somehow violate your feelings of sacredness? Have you actually had a convo with your BF about your feelings about what makes sex sacred?

Also, you mentioned that you've hooked up with others and it hasn't changed your feelings for him - presumably this happened recently? How does hooking up play into your feelings about sex being sacred? Or was the hooking up not actually sex, but making out or something less involved?

Either way, if you've hooked up with others and your feelings for him haven't changed, then would it be surprising if him having sex with someone hasn't changed his feelings about you? How do you reconcile hooking up with someone and still wanting your ex/wanting him to want you whereas you feel upset that he did the same thing, and are in pain about it? Do you think that sounds like a bit of a double standard?

Lastly, FTR, nothing you're saying sounds like you actually want to BE poly. It sounds like you might try to live polyamorously to make your guy happy. There are some people here that are poly people with mono partners (and I know a couple in real life that are truly happy that way), but most of what I've read about that - the mono person is miserable much of the time, and really can't deal with it. Do you want to live like that, and close yourself off like that, when if you keep yourself out there & dating, you might find the perfect mono person for yourself?

It definitely has more to do with him. I have hooked up meaning everything but full on anal sex. I have a very limited history with casual sex. He's much more experienced and open than I have been in the past. We are not officially back together. We both want to be sure that this is something that's right for me. My hookups haven't changed my feelings but knowing he's slept with someone else is difficult for me. That leads me to believe is mostly possessive which is not a good emotion to have in a relationship or in general. He doesn't want to feel owned and I understand that. I need some advice and tips for getting over my posseveness.

I want to make sure that I'm clear on this.

You want to work on your possessiveness for you, because it bothers you, or because you want to have a relationship with this particular man, and the only way to do it is for you to be poly?

Or both?

If he was fine with your possessiveness and being monogamous, would you be happy with yourself as you are?

Also, when you say "possessiveness" do you simply mean feeling possessive, or are their possessive behaviors that go along with this? Questioning him a lot? Being angry at him? Checking his email? What does possessiveness mean here?

I am sorry you struggle.

I was somewhat mentally prepared for it but I'm still having a hard time processing it. It doesn't feel like jealousy as much as sadness, a feeling that the bond we shared is broken and can't be fixed.

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Under the circumstances, that is normal to feel. If you guys had been exclusive for 5 years, then broke up, the first time he sleeps with another person, something HAS been lost. That exclusivity to you. Just like when you sleep with someone else – it's been lost on your side. That exclusivity to him. I wonder if you guys did not give it enough time between breaking up and trying on this new model?

We've decided to just see each other with no strings or rules right now, until Experience can show me what I want.

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I don't know that I would have considered it if he didn't need it but that doesn't mean that it may not be right for me.

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If this (non-exclusive, no strings, no rules) thing with him is a trial run, try on it for the time frame specificed. Then make the call if it is for you or not. What was the time frame?

I recognize that he hasn't seen sex as sacred like I have and maybe that is something that needs to change about me.

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Or you accept you have different views on sex. He believes X and you believe Y.

I need some advice and tips for getting over my possessiveness.

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Could be exes who are NOT also casually hooking up. Then you are not sharing non-sacred sex with him feeling all weird.

Could change the model you practice together because that "no strings/no expectations" model doesn't groove for you. Bring that "officially together" and "sacred sex" thing that matters to you back into the arrangement. Whether or not that ALSO includes some kind of open model is another thing to resolve... but you don't sound "possessive" to me as much as you sound sad that you are going against your own grain and not getting some things you value in the current arrangement.

You value "official" dating and sacred sex -- and there's not any of that here.

You aren't all that keen sounding on open relationships. Yet here you you are just going along with it to be with him (?) or to figure out if it is for you or not and sad it is looking like not. (??)

I could be wrong though. What do you value in your romantic relationships?

Galagirl

LizziE said:

I want to make sure that I'm clear on this.

You want to work on your possessiveness for you, because it bothers you, or because you want to have a relationship with this particular man, and the only way to do it is for you to be poly?

Or both?

If he was fine with your possessiveness and being monogamous, would you be happy with yourself as you are?

Also, when you say "possessiveness" do you simply mean feeling possessive, or are their possessive behaviors that go along with this? Questioning him a lot? Being angry at him? Checking his email? What does possessiveness mean here?

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Yes of course I want to work on my possessiveness for me. Can possession be healthy in any relationship? Monogamous or not? Where that leads me ultimately is yet to be seen. Should I have a problem with him sleeping with other people simply because I don't like to share? Probably not. Do I still want a relationship with him? I don't know. That also remains to be seen but the biggest issue is the no monogamy and weather or not it's something that will work for me. And yes, I have spud on him before and I do still check up on his Facebook and dating sights so I am definitely possessive.

If we were both ok with monogamy and possession would I get back into a relationship with him? I don't know? I don't know if my reasons for not wanting him o sleep with someone else are fair. If it's silly possessiveness it's probably not fair. At this point it does t matte because he has slept with someone so that part of us is gone for good. Yeah my heart is broken a little broken but mostly because what I believed in us officially gone. He isn't mine anymore. My illusion that we would only be together is over so one way or another I need to move on ok just not sure what direction yet. I can't decide what's right for me at this point because I've never even considered this as an option but I'm starting to wonder if it's mainly conditioning and the way I was raised.

You sound upset. I'm so sorry.

My illusion that we would only be together is over so one way or another I need to move on ok just not sure what direction yet.

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I think you could focus on being exes. A break up with firmer boundaries. Could stop casually hooking up with him and focus more on accepting and healing from the break up first. Rather than try to change all these things about yourself so it can keep on going.

You don't sound like you dig non-monogamy and you don't dig casual hook up sex. It is OK to have those preferences. There's nothing wrong with them.

Galagirl

GalaGirl said:

You sound upset. I'm so sorry.



I think you could focus on being exes. A break up with firmer boundaries. Could stop casually hooking up with him and focus more on accepting and healing from the break up first. Rather than try to change all these things about yourself so it can keep on going.

You don't sound like you dig non-monogamy and you don't dig casual hook up sex. It is OK to have those preferences. There's nothing wrong with them.

Galagirl

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I'm not upset just confused. We took time apart and it helped but this is the first time he's been with someone else. I know I still love him. It's just that what I originally envisioned for us is not a reality anymore. I can't really decide without more time I just want to know how to deal with the possevness. I don't know if it'll work for me but assuming it won't just because I've only known one thing is closed minded. I'm not willing to give up on us if I'm just closed minded

That's the thing though. You don't sound close minded to me. You were willing to give it a try for a while. Just maybe turning out that "no strings/no expectations" isn't your thing. What you call "possessive" I see as "I don't feel safe and secure in this model." What time frame did you guys agree to try this model on for before making final call? Is the time up?

The only other choices I see so you can feel safe and secure are

a) change the model. Non-monogamy with some expectations.
b) end the model. No hooking up. Be friends rather than dating partners or sex partners.

Both give you some clear cut boundaries and you can know what's going on/what to expect.

But going at it "neither here nor there" sounds confusing for you.

Galagirl

Based on what you've said, I agree with GalaGirl, in that it sounds like a full break-up with him for a while might be good.

It sounds like you are questioning a lot of why you feel the things you feel. That can be a really good thing; it can lead to learning how to be a better you. And by a "better" you, I mean coming closer to the person you truly are, finding all the places/thoughts/modes of being that are most comfortable to you.

But that's a hard thing to do, while you're trying to pursue or have a relationship with another person. Because we can (even unconsciously) shy away from some paths of personal growth because those paths would take us away from the person that we're hoping to grow towards.

If I were you, I'd definitely explore why you do things like check his dating sites and spy on him (I think where you typed "spud" you meant "spied", please correct me if I'm wrong). Mono or poly. behaviors like that are definitely unhealthy for both you and for him.

Also, and I say this from the heart, before you do anything else, please take a big chunk of time to grieve that what you thought would happen won't happen anymore. I've been through a few experiences in the last few years where I had a major change in my life. In one of them, I slowly came to the realization that the polycule (group of poly people I was a part of) that I thought I was going to buy a home with and spend the rest of my life with had one particularly toxic member who was so toxic and attempted to be controlling so much that I ultimately had to walk away from that polycule. That was my whole life, something that we'd been planning for several years, gone. Over.

I didn't take the time, at the time it happened, to fully mourn it, and not taking that time is part of why I feel a bit burned out on relationships now. I am taking that time now. I wish I'd taken it then.

So imo, before you go farther, I'd say that taking a full break from this guy, maybe for a month or two, to mourn and also give yourself time and space to figure out what YOU want and why might be a really good idea. You could always try go back to this guy, if you find yourself feeling comfortable with poly, and he is poly, and you still want to be with him. There's no guarantee that would work, but whether it would or not, it sounds like the first thing you need to focus on is you.

Just curious, are you sure you are monogamous. You do not sound like you were happy with being a serial monogamous person.

That's the whole problem. Monogamy has been all I know. My past as a serial monogamist does make me wonder if I'd be happier in an open or poly situation. However, I'm having a hard time dealing with the idea of him sleeping with someone else.

I'm insecure- the man he slept with has a gym body, he's older, has money and is more masculine than me.

My friend/ex assures me that is just a matter of variety. I'm a fairly vain person. I feel inferior and like the only reason he wants this is so that he can be with men who are more muscular than me. I wonder if the other man is better in bed. I wonder what positions they got into and if they did things we haven't done or haven't done in a long time. I wonder if he's giving this person who he just met more than he gives me.

I'm disappointed in myself . I feel like I let him down- like I want good enough or adventurous enough in bed. I am angry that I don't know how to just be ok. I don't know why I have to make sex such a powerful thing. I wish I knew how to just let it be something free. So many of my friends are able to do so, but the thought of him sleeping with someone else ( especially as a bottom) feels like he's stabbing me in the heart and saying " I don't care if this hurts you".

Fear of loss there is some of that but I do have to say that it's less of a concern than anything else.. We seem to have a very hard time staying away from each other. I do believe that if he thought I could be a partner who doesn't chain him down and make him feel "owned" then I'm sure he'd want to be back together. However, if I am polyamorous and become comfortable with it. I'm not sure he'd be my primary partner. In addition to sex he wants a lot of freedom. He doesn't want to "answer" to anyone. I definitely know that I enjoy being coupled. I enjoy having someone I can count on t make me number one. If we were to get back together I may want to seek a more relationship minded primary partner.

Experience He's( my ex) so much more open and free with sex than I am. I know he will have so many experiences I'd never consider: things that scare me or make me feel uncomfortable. He will probably also have more sexual partners than me. He's bisexual and will be with men and women. He's also less discriminating than me and will sleep with people I find unattractive while I'll only hook up with people I find very attractive.

He's so skilled in bed. He's the first person to really open me yo new things sexually and it meant something to me. He's the first and only man I have bottomed for( so in a sense he took my virginity at a very late age). I've only given that to him, my entire life. He's so free about giving it to others it makes me feel like I'm not special. For years I let myself believ
e that I was privileged that he gave that part of himself to me.

I want to be happy for him. If any of my friends had been with a man that looks like that I'd be happy for them.

Jealousy I was so numb when he first told me that I couldn't process the jealousy. I'm jealous now. Will this man take his time away from me? Will it change our sex life? I wanted to have sex the other night and he wasn't up for it. I immediately felt heartbroken because he'd done it with someone else 2 days ago and now I felt like he was holding out on me or exhausted himself with someone else. He is online right now and I keep thinking that he's planning his next tryst with this man. I keep wondering how I'm going to suffer in comparison.

Disgusted by his choices . He's chatting with a girl I've may and find to be unattractive, he's hooked up with another guy who I can't understand how anyone could want to see unclothed( and who claims to be straight). Now he's slept with a man who is muscle bound and old enough to be his father. My friend/ex is a small guy who looks very young and weighs about 140 pounds. I am older than him and I'm a more masculine build but I'm not this man. The thought of this man, who has three children and just separated from his wife of 17 years being inside the person I love makes me sick to my stomach.

Thank you everyone for your replies. They are helping. As many people suggested, I could be someone who could benefit from being poly or being monogamous. However in order to know for sure I have to experience the emotions I go through knowing he is intimate with others. I don't seem to have a problem with being with others myself and I always thought I would. I feel that the emotions I'm going through are all negative ones that will hopefully get better over time and with diligent work on myself. I do feel that I'm exploring this for myself. He is a factor of course but again, there are other things about him that make him less than an ideal relationship for me. I'm aware of that and that if I do enter into a polyamorous relationship he may still not be an appropriate primary for me. Even my therapist agrees that continuing to see him may be good for me. I'm not good at pushing my comfort levels unless I have to. By choosing to continue to see him I am forced to push the comfort levels that otherwise may just force me to go back to monogamy because it's all I know.

If anyone has some good advice to help me work through the emotions I'm going through, please let me know. I need advice but I don't need people to tell me who I am or what I should be trying. Only experience and time will tell me that

Be patient. You will work it out I am sure. Give yourself time and maybe a little space.
I think you are going through something I went through and that is what you believe and feel are not always what you were taught to believe.

It sounds like he might be a solo poly person. If his freedom is the most important thing to him (a reasonable life choice), then it's possible that you could be partners, but it sounds like even then, you would need to keep in mind and be comfortable with/come to terms with his freedom coming first to him.

One thing that concerns me is if you're disgusted by his choices. I know you've said that you love him; how do you feel that someone you love so much also does things that you find disgusting? Is this a new experience for you - in other words, have you had previous partners who did things that evoked disgust in you or it that unique to this partner?

For how to process some of your feelings, especially those of inferiority, I'd suggest reframing your view on some of those things to be about how you view friendships. I'm going to assume that you have a couple of friends, and that you enjoy different aspects of their personalities. Spending time with one friend doesn't mean that you dislike the other. And yes, there may be some things where you say "I really like going kayaking with Greg and Matt, but given the choice, I'd rather kayak with Matt and go canoeing with Greg, because Matt is more physically fit and able to kayak at the speed I want, whereas Greg is much better and synchronizing padding, so going canoeing with him is more fun". Neither of those is an insult to Matt or to Greg; but it is an evaluation of what you enjoy the most with both of them, and reordering your time with them (perhaps) to do things with them that are the most fun.

For the sex stuff (what positions were they in? were they doing things that I'd love to do with him, but he and I haven't done in years?), I'd ask if you have the kind of relationship with your guy where you could ask him something like "Is there anything we're not doing that you'd like to do?" And if ruminating over the sex he was having with someone else caused you to remember a position or style of fucking that you used to do with him and loved, but haven't done in a while, you could follow that up with "Because I really loved it when we did XXX, and I'd love to do that with you again soon", if you're still having a sexual relationship with him.

Speaking from personal experience, doing something sexual and new (or not new, but something I'd forgotten I liked doing) with one partner often causes me to "bring it home" to my other partner(s) if it's stuff I'd like to do with them too, or think they'd like. I think the only time that I ever "held back" on a sex act with a partner is when I knew that they had ZERO interest in that thing - my partner Jon, for instance, has no interest in ass play with his own ass. Nothing. Zero. Nada. So, when I had a partner for awhile who loved pegging (which I also love), I scratched that particular itch with that partner, and never brought that home to Jon, because I knew he would have no interest in it.

But when that partner and I did other things (not remembering what, but just remembering the situation) that I thought Jon would like, I either suggested it to him as a future thing (if it'd take planning or I'd want to make sure he wanted to do it) or just tried it out with him, if it was something close enough to our usual activities that it didn't involve making sure he'd be comfortable.

I hope those help. It sounds like right now you really don't know what would be good for you. I don't mean that meanly, I mean that in a "this seems like a growing time for you" kind of way. The main thing I would say about that is that I still feel strongly about always checking in with yourself, and making sure that what you're doing is being done FOR YOU, because YOU want it, and because it furthers you growing more into you, and making sure that you're not trying to grow towards your guy. I know I said it already, but it's one of those things that I remind myself of too, because it's so important.

nycsinger2000 said:

My past as a serial monogamist does make me wonder if I'd be happier in an open or poly situation.

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That is issue number one. We all know open model relationships are more common in gay male culture than in MF or FF ones. But you need to take the time to see which better suits you personally. Maybe you're polysexual but can only love one at a time. Maybe you can find "sacred sex" with several partners. I can and do feel the divine when I am with any and all of my lovers. It may not feel sacred to them, but it does to me! But if feeling "sacred" for you means monogamy, and you don't want sex with several partners, that is your choice.

However, I'm having a hard time dealing with the idea of him sleeping with someone else.

I'm insecure- the man he slept with has a gym body, he's older, has money and is more masculine than me.

My friend/ex assures me that is just a matter of variety... I feel inferior and like the only reason he wants this is so that he can be with men who are more muscular than me.

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OK, your vanity and pride are impacting your sex and love life. Perhaps you could let go of some of the vanity. Perhaps you exercise more if you feel your partner is disappointed in your body. I know that some newly poly people have "let themselves go" in comfortable monogamy, and do start back into more care about exercise and diet when their partner begins to date. Not just to look better for their partner, but also because since the partner is out more, they have more free time and decide to work off some of their stress at the gym, or in sport.

I wonder if the other man is better in bed... what positions they got into and if they did things we haven't done or haven't done in a long time... if he's giving this person who he just met more than he gives me.

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You know what? Some of my partners ARE better in bed than others. But all of them are damn good in bed (couch, blanket in front of the fireplace, kitchen counter, shower, tent, back of the van, etc). If they weren't, I wouldn't be dating them. My LTR gf might not be as objectively "good" in bed as my aggressive sexy male Dom, but she is more tender and cuddly and kissyface and praises me more, and showers with me, and loves the same TV shows I do, and loves my cooking and decorating skills. The Dom doesn't even know what my favorite TV show or meal is! He might be colorblind for all I know, and unable to appreciate the fall display of collectibles I have on the mantelpiece right now. So, just because miss pixi may not make me cum as hard, or as often, does not mean I value her less. When you seek variety as a polyamorous or polysexual person, you don't look for the "best" person (whatever that means), you get off on appreciating each person's *uniqueness.*

I'm disappointed in myself . I feel like I let him down- like I wasn't good enough or adventurous enough...

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Had your sex life actually gotten stale and infrequent, or is this just a fear?

I am angry that I don't know how to just be ok. I don't know why I have to make sex such a powerful thing. I wish I knew how to just let it be something free. So many of my friends are able to do so...

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The more open model in male gay culture is more common, since all men are trained to believe frequent casual sex makes them a "stud." (Of course, women are taught that having frequent casual sex makes them a filthy tramp.) But your preference as a human being is quite common. Many people do honestly prefer being committed to just one other, and it brings them joy. Being polysexual makes them anxious. Try not to judge yourself as you experiement with open models.

but the thought of him sleeping with someone else... feels like he's stabbing me in the heart and saying " I don't care if this hurts you".

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And your feeling is valid. He may not be thinking that, and probably isn't, but the fact remains, you ARE hurt. If he needs to be poly though, the only way to make the hurt go away is to leave him. It's not fair, and doesn't work, to demand he be mono.

Some couples, where either or both of them are poly, can choose to "close" for a time, or permanently, but it's a choice each of them has to make for themselves individually, for personal benefit and not just to please one while the other feels stifled and suffers.

Fear of loss there is some of that but... We seem to have a very hard time staying away from each other. I do believe that if he thought I could be a partner who doesn't chain him down and make him feel "owned" then I'm sure he'd want to be back together. However, if I am polyamorous and become comfortable with it, I'm not sure he'd be my primary partner. In addition to sex he wants a lot of freedom... I enjoy having someone I can count on to make me number one... I may want to seek a more relationship minded primary partner.

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Good insight.

Experience He's so much more open and free with sex than I am. I know he will have so many experiences I'd never consider... He will probably also have more sexual partners than me. He... will be with men and women. He's also less discriminating than me and will sleep with people I find unattractive...

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Maybe it squicks you out to be with someone who is so undiscriminating compared to you.

He's so skilled in bed. He's the first person to really open me to new things sexually and it meant something to me. He's the first and only man I have bottomed for... He's so free about giving it to others it makes me feel like I'm not special. For years I let myself believe that I was privileged that he gave that part of himself to me.

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I am a little confused whether you two switched up who got the anal, and what he is doing now, but either way, I sense your insecurity about who he's fucking now, whether as the penetrator or penetratee.

Jealousy Will this man take his time away from me?

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It could. You need to assess how much time you need with your guy... Talk it out. Maybe you could still have as much time, and he would drop a hobby or something else time consuming, to be with another partner. Otoh, maybe you'd grow to enjoy more "me time."

Will it change our sex life? I wanted to have sex the other night and he wasn't up for it. I immediately felt heartbroken because he'd done it with someone else 2 days ago and now I felt like he was holding out on me or exhausted himself with someone else.

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Could be, or he could've just not been in the mood. Had he ever not been in the mood before?

He is online right now and I keep thinking that he's planning his next tryst with this man. I keep wondering how I'm going to suffer in comparison.

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Comparison is a bitch. Generally there is less jealousy when you trust and really understand what your partner is getting out of their other relationship(s). I've been on both sides. I wasn't (and am not) jealous of my gf's others, but I was of my bf's since I didn't know or trust him as much, and I also questioned his taste in partners, and his lack of ethics in how he dated.

Disgusted by his choices . He's chatting with a girl I've met and find to be unattractive, he's hooked up with another guy who I can't understand how anyone could want to see unclothed (and who claims to be straight). Now he's slept with a man who is muscle bound and old enough to be his father...

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These concerns can definitely affect your desire for your partner! Sometimes you can grow to accept it, and sometimes you can't. With my ex bf, it affected my desire for him to such a huge extent, it was a large part of the cause of our breakup. It wasn't their physical attractiveness, or lack thereof, as much as it was their personalities, their ethics, and the fact that 3 women in a row he chose to date had herpes. Herpes isn't the end of the world, but both he and I are free of it, and I just really didn't want to risk getting the disease. Also, we had been fluid bonded, and I was not really thrilled to consider going back to condoms (not that condoms entirely prevent herpes anyway).

My friend/ex is a small guy who looks very young and weighs about 140 pounds. I am older than him and I'm a more masculine build but I'm not this man. The thought of this man, who has three children and just separated from his wife of 17 years being inside the person I love makes me sick to my stomach.

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This is the messy ethics idea. It can give one pause, for sure.

Continued:

As many people suggested, I could be someone who could benefit from being poly or being monogamous. However in order to know for sure I have to experience the emotions I go through knowing he is intimate with others. I don't seem to have a problem with being with others myself and I always thought I would. I feel that the emotions I'm going through are all negative ones that will hopefully get better over time and with diligent work on myself. I do feel that I'm exploring this for myself. He is a factor of course, but again, there are other things about him that make him less than an ideal relationship for me. I'm aware of that and that if I do enter into a polyamorous relationship he may still not be an appropriate primary for me. Even my therapist agrees that continuing to see him may be good for me. I'm not good at pushing my comfort levels unless I have to. By choosing to continue to see him I am forced to push the comfort levels that otherwise may just force me to go back to monogamy because it's all I know.

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This is also good insight and hopefully writing here, and talking to your therapist, and going out of your comfort zone a little, will continue to help you question and grow, and work from a place of information and security, and not just feel like you're floundering rudderless in a sea of fears.

I don't need people to tell me who I am or what I should be trying. Only experience and time will tell me that

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Yep! Relationships are hard. I hope you will continue to feel stronger and more confident, and end up in a good satisfying relationship, or more than one, with someone(s) suited to your new self.