Hey! So we're both on antidepressants and we're both new to sex (we are each other's firsts) which could be a contributing factor. We're both very into each other however and in love.
I'll get into a lot of detail below, just so I can show what advice we've used and how we're doing things right now.
We still had a lot of fun, from what I could tell. There was lots of communication to do what felt best, questions like "higher or lower?" "Up and down or circles?" "Harder or lighter?" Things like that to make things feel as good as they could. He was very loud. It did sound and look genuine since it was accompanied by body reactions, like there was also times he couldn't stop spasming/shaking and his cock would twitch.
He is submissive. I tied him up to his request, used a vibrator at some points, dirty talked the way he likes it, we took turns topping, etc. Reverse cowgirl, cowgirl, missionary, doggystyle, but still nada. I scratched and spanked him (he likes a little pain) and though it made him more verbal, still nada. We were at it for hours.
He said he had an amazing time, it was very hot, it was great, etc. But I'm just a little insecure considering I didn't get him to cum.
He likes the area behind his balls massaged and sometimes likes his balls squeezed as I ride him.
We haven't tried prostate play, which I heard can help men who have trouble releasing. He is interested in trying this someday when he's ready, but until then, is there anything else I could try?
When I was riding him, I made sure to ask which methods of moving felt best for him and moved that way until I got too tired. He had his eyes closed and couldn't be quiet, but a part of me wonders if I wasn't riding him right. I usually rolled my hips in different ways, it was more risky to go in and out too much because he kept slipping out. Sometimes I'd lean down and kiss him or suck his neck or nipples. He said it felt amazing and couldn't keep quiet
When he was on top with missionary we tried a lot of different thrusting methods. Sometimes he'd go in all the way and go out all the way(not as much trouble slipping out in this position), rotate his hips in small movements, try different angles etc. He said that he was close for a long while, but he couldn't quite get there. Dirty talking the way he likes helped a little.
We also put pillows underneath our butts to help the angle.
We had plenty of lube, but we didn't use anything like viagra. I was also able to get him hard quickly every time he got soft. We took turns between heating lube and oil.
He does say he likes me being spontaneous and surprising him. Maybe I'm not creative enough and I can't think of more ways to be spontaneous. Is there any more ways I could surprise him? I'll do things like kiss, scratch, target his sensitive spots, bite, VERY lightly choke (ask him the right pressure), spank, etc.
Tools I have
Belts, rope, heating lube, coconut oil, avocado oil, dildos(to get him hard after he got soft, I had him use one on me), rose toy(he LOVES the rose toy used on his tip and behind his balls), electric toothbrush, butt plug. He likes bdsm
In case this helps, his most sensitive spots, from what I've noticed: balls, cock tip, behind the balls, ass(playing around the rim, not inside), neck, nipple, tongue
I give him permission to feel me however he likes while we have sex. Sometimes I put his hand on my chest or ass to encourage him.
Also we don't use a condom. We don't need to, since we're both heavy introverts who don't get around and there's 10000% no risk of pregnancy. I have no doubts we're the only ones we're fucking, he's a shy person and it takes a lot getting him out of his shell. Same for me.