So, I have this friend who I hang out with about once a week. I really want to bring up and try mutual masturbation with him (I'm a 14 year old male), but don't have the courage. I am always thought of as the "innocent one" with him, because he makes all the dirty jokes and I am not brave enough to even say "that's what she said" around anyone.
This all started about when we were both 10, and were having a sleepover. It was a sleepover between two boys, so things (of course) got crazy. We had to sleep in the same bed, and it was about midnight, so his parents were asleep, and we were starting to get hyper. He pulled his pants off and his shirt, and jumped on me, with only his boxers. He had just learned from one of his friends about humping (and me too), so he started to hump me, saying "I'm humping you, I'm humping you!". I could feel his erection against mine, since he was in boxers and I had thin pajamas on. I pretended that I didn't like it and fought back, when I actually wanted him to continue and do the same to him. Then, we went on the floor, and we both had obvious erections. We were looking at each others, and he said, "hey, look at me". I look over, and he pulls down his boxers and humps me, again, but this time, naked. He pulls off all my clothes down to my boxers and started to hump my butt. Again, I struggled, but really enjoyed it because I wasn't brave enough to just let it happen. He then pinned me to the floor because he was stronger, and (pretending) to give up out of exhaustion. He then turned me to my back and started to hump my pelvic area again, and it felt really good. I turned over, and here he pulled off my boxers, and was feeling my butt. I pulled back because I was too shy and put my boxers back on. For the time I was running away, he couldn't stop looking at my penis and I couldn't stop looking at his. He told me to touch his because his had the foreskin, while mine didn't. He reached for mine under my boxers, while I still rejected the idea of touching his or him touching mine and pulled away. Then, unfortunately, he put his boxers on, and we were just laying there, but with his penis hanging out, and me staring at it. We both fell asleep there.
To this day, I do regret not taking it further because I now know the pleasures of masturbating, and hear that doing it with a friend is way better. Also, I feel like a situation like that will not occur again. I feel like we both want it, but he doesn't want to bring it up because he thinks I am innocent and would say no, but I'm not brave enough to. I know it's not as easy as just saying "you wanna masturbate together?" and him saying "yes", but I am still scared to just talk about masturbation. I've seen other advice that is just to ease into it by watching some sexual videos together, or starting the topic of masturbation, but I'm too scared. He is definitely very comfortable around me, though. Once, he just started looking at his penis and moving it around. I looked at him, and he told me "I'm having some adjustment issues". I have tried to ease into it physically, like by pinning him down, and laying on top of him and moving up and down, but he doesn't seem to get the cue, and if he did, he would say something like "getting a little close there" even though I can tell he's fine with it. He's even cued at it a little, too, but I was too scared and acted like I didn't notice. Also, I know that he would be my only friend who would be willing to do this with me, but I am just too scared :(.
I guess that was pretty long, but the main question I have is, I want to try mutual masturbation with a friend, but don't know how to bring up the topic. Thanks!
Also, just some extra stuff:
1-Neither of us are gay, we are just going through puberty and are experimenting. We both have our interests in girls, too. I don't have anything against gays, just don't want to be flooded by people calling me gay.
2- He also has looked at my penis (for example) when I use his doorless bathroom. I pretend not to notice, but he doesn't do anything other than look.
this is noting to worry about just spend quiet time and tell him u liked it
dear
SO you need some thing really wenjoyable and avilable to insert inside p***y ?
wel first may I ask if you are virgin or not
NOW . thats great and enjoyable for a boy/guy so that he needs a lot of efforts in f*****g and opening your hole hard and difficult.
i suppose you have to start with small tingy nice pretty short things inside your c**t.
then lisstle by little try to WIDEN it by using vegetables like cucumbers, cabbages and then you can use yur hair styler
even if yo are virgin you can use them around the hole and not deep inside your p***y
best wishes