I'm 19 and I've been sleeping with a 39-year-old for a few months—which I know sounds like a really bad idea but he's really kind and I've enjoyed the time we've spent together and I'm really attracted to him. My problem is I've never been able to cum with a partner in any capacity, I can't even make myself cum in front of them, I've just kind of accepted that I can't cum with another person only on my own. I knew it bothers the guy I've been sleeping with he's tried really hard to get me cum with his mouth hands, and dick. He's said that he thinks I'm mentally having problems letting go, which is absolutely true but I still can't cum. The other day I went over to his place and he had bought like 4 different types of dildos anal beads and a vibrator. I still didn't cum, I don't know what to do. I want to continue to sleep with him but I feel if I continue not to be able to cum he won't want to. I have a lot of issues with my self including body dysmorphia disorder, eating disorders, and problems with self harm that I'm trying to work through. I feel that this is why I can't cum though I've never told him about any of that and I really don't want to but I really think that's why it's so hard for me to be open. I am really attracted to him, and I really like sleeping with him. What else do you think I should try to do to solve this issue?

Come On Already

My response to COA—and hers to mine, and mine to hers—after the jump...

A quick note before we get to my exchange with COA: I somehow misread the first line of her email as "I'm 39 and I've been sleeping with a 19-year-old." Adult onset dyslexia—is that a thing? Suffice it to say, I probably wouldn't have sent my initial two-word response to COA if I had realized that she was the teenager in this relationship. Anyway...

Try pot.—Dan

I smoke often.—COA

Have you tried masturbating alone in a room while he is somewhere else in your apartment?—Dan

No only when he's in the same room watching me.—COA

But you come fine when you masturbate solo?—Dan

Yes it's pretty easy to cum alone.—COA

My advice for you: plant that boy outside your bedroom door—your closed bedroom door—and masturbate solo. Put a pair of headphones on him and play some loud music so he can't hear you. If you can come that way, try again with the door open but still with your boytoy blindfolded and headphoned. Come that way? Great: next time put him in the room, at the foot of the bed, sitting in a chair—also blindfolded, also headphoned. Now you can see him, COA, but he can't see or hear you. Gradually bring him a little bit closer after each successful masturbation scene until he is in your bed without a blindfold or headphones on. It'll take some time to get there, COA, but think of all the orgasms you'll have along the way.—Dan

Ok I'll give that a try. Thank you!—COA

I didn't realize my mistake—COA is 19, her boytoy is 39—until I pulled her letter up for the SLLOTD. Oops. I would've mentioned the "campsite rule" and the "tea and sympathy rule" to COA if I had caught the mistake while we were emailing. I probably should've urged COA to tell her 39-year-old boytoy to stop pressuring her, as that's probably not going to help. There's a difference between being invested in your partner's pleasure and putting pressure on your partner to perform pleasure for your benefit.