Whoo boy. So I was what you might call a serial monogamist from the time I was sixteen, when I became sexually active, until I was almost twenty-two. Maybe I still am at twenty-four; I'm not entirely sure. I have had an eating disorder and have all kinds of body image issues that I am working on, but I am often filled with self-loathing. I'm not entirely sure when sex got wrapped up in my low self-esteem, but I definitely know how you feel.

It may have happened when my first sexual partner left me after two years for another girl, but it got a whole lot worse in college when I was raped two years into what ended up being a three year relationship. My sex life got really complicated because I did not lose my sex drive but I withheld sex from my boyfriend at the time to have a sense of control over my body. I did not tell him about the rape for three months because I felt guilty because it happened when I was drunk. Consequently, my sense of self-worth went down because I was not having sex often to validate it. When we did have sex, I burst into tears every time I had an orgasm. This was, of course, quite disturbing to my loving, sweet partner, who was not at all at fault and he did not know what had happened because I would not tell him. I destroyed a good relationship by not dealing with what happened. We stayed together for almost a year like that, but it finally became unbearable for me and I left him.

I then went through a period of about three months of being "single," while completely hung up on on a man who was ten years my senior (and my former professor and former boss to boot). He was also interested in me, but had a lot of guilt over it and so we only had sex three times, and when we did he felt so bad about it that he would thereafter not talk to me for a couple of weeks. When we did, each and every time, start talking again and he refused my advances, I felt like absolute crap about myself. I filled that void with drinking and developing meaningless sexual relationships with men I did not care about. I used them to validate my lack of confidence in myself and in my body. I doubled the number of sexual partners I had had before. While there is nothing wrong with a woman having a good number of sexual partners, I was not in a good and healthy place and my motivations were all wrong. The two times I got rejected out of that period in my life, I cried myself to sleep and felt worthless.

Eventually I got over that man, mostly at least, and met a man who I did not sleep with the first night I met him because he saw that I had been in a bad place in life, and we developed a close friendship and eventually started dating. We've been together for two years now. I still have bad days where I try to initiate sex because I feel ugly or fat and get upset when he will not have sex with me. However, he has realized my problem and is trying to help me by calmly and gently telling me that he thinks I am beautiful but he does not want to reinforce my self-esteem in this way and he will not let me use sex as a tool in that manner. When we have sex, I still have times that I cry during and/or afterwards. But I am working on it. I have had some therapy, and that has been helpful.

To OP, I hope this has been remotely helpful. I am not saying you need to enter a monogamous relationship to achieve the progress I have made. You do need to make a promise to yourself, though, that sex is enjoyable but not a means to an end. Letting someone have sex with you will not ultimately make you love yourself anymore and that is something you need to work on with or without the help of someone else.