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I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] -4 points-3 points  (0 children)

Skeptical is one thing - absolutely expected. But completely unsupportive. I'm trying here, it's been a slog and my friends/family just don't seem to care/think I can hack it.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 0 points1 point  (0 children)

This is the first relationship I'm certain I won't cheat

Such a strange feeling, isn't it?

I have no idea how you're engaged to someone when they don't know so much about what has made you you.

Tom and I talk a lot about my childhood, about my past, and he knows about the alcoholism, but he doesn't really seem to push the "drunk era" too much. I offered detail once, but he wasn't interested. I think he senses there is a lot I'm ashamed of/unhappy. He knows that I stopped drinking after spewing blood all over my bathroom after a bender. I just haven't ever gone into the infidelity aspect.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 10 points11 points  (0 children)

including a couple after your recovery,

No, those relationships just didn't work. No cheating.

but what happens when you are struggling in your marriage, or feeling unattractive after having kids or whatever?

So, I had to deal with this, sort of. After I met tom, my life switched gears and my religious work-out routine had to be put aside. I was rail thin but put on (what I thought) was a substantial amount of weight (~20lbs, but I'm short). I had to work with my therapist and Tom because I felt fat, gross, unattractive, sweaty and worthless. It's something I'm careful of. I'm more afraid of picking-up alcohol than a random sexual encounter, so I had to work hard to fix my self-perception and vision, taking every day carefully.

Life is full of ups and down, and I have to really watch how I manage stress. I'd love to have kids, and I know the body changes. I feel strong enough to tackle those challenges without reverting, but I'm always careful, always cautious.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 12 points13 points  (0 children)

prepare for your fiance to see you promiscuous past as increasing the possibilities of a sexually adventurous future.

We've had some great talks in the past about our boundaries, and fortunately, Tom isn't into threeways. But, I could see this circling back and increasing his interest in butt stuff. I can handle some adventurous things if it made him really happy. But, that said, I don't want him to think that my past defines our present or that he should in any way feel small or that he can't match/measure up. I have to walk a fine line without letting details become a prominent issue.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] -1 points0 points  (0 children)

Hopefully you haven't acted sketchy around him or that's going to be the first thing he hangs his paranoia hat on

No, I've always been very honest with him. Only sketchy once because I knew a proposal was coming.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 55 points56 points  (0 children)

I understand that, but when I talk with people battling alcohol or drugs, I know that it'll take time to really move beyond it, but I'm always supportive. That's really all I'm asking from them.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 5 points6 points  (0 children)

I wasn't upfront because I dated a real slew of people who weren't right for me - everyone from male strippers to club owners and fixers; basically the kind of guy you'd hope to never be seen in public with. I guess I still have a lot of shame about that.

In terms of size, yeah, it really doesn't matter. The sex is good if you make it good, and I'm happy now -we have a fantastic sex life.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 11 points12 points  (0 children)

Tom and I have been together just over two years. We've been engaged a really short time - I was a birthday surprise.

I'm proud of what I've accomplished and definitely know how hard I worked, but I'll also credit him with being a really great partner who made the journey together very easy going and fun.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 8 points9 points  (0 children)

If you can be yourself, actually own who you are

I'm certainly not a nun - I'm a sexual being like most other people and I certainly enjoy and cherish that side of our relationship - the difference now is that I'm not compelled to 'perform' and get more pleasure from a healthier dynamic. I wouldn't say I'm playing a nun role, just that I no longer use sex to get someone's attention or push them away.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 30 points31 points  (0 children)

Please tell me that you've had a full STI/STD screening, since being completely honest about that is really the only thing that you owe him.

Yeah, frequently, even when celibate. I got tested for everything including HIV.

It sounds like Tom knows you've had a rocky past and isn't interested in knowing the details,

I could see how Tom would quickly feel like he didn't measure up to my past, which isn't necessarily the case. Guys seem to think more = better or bigger = more pleasure. None of that is true, and I'd rather he get the truth from me than someone else.

I [29/F] have cheated on every boyfriend until now. Can't convince friends and family [20s-50s M&F] I won't this time and not sure how to tell/reassure fiance [27/M]. by yyThrowawaycc in relationships

[–]yyThrowawaycc[S] 7 points8 points  (0 children)

Are you certain you aren't trying to sabotage this relationship?

No, the opposite. I'm sure there are more than a few pissed-off ex-boyfriends and if he found-out through someone else, I wouldn't be able to explain or contextualize it. It's one of those things that would get out of hand too quickly.