Virgin bfs first time

BlueBearCub

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Hey guys so I have been dating my boyfriend for over a month and it has been great so far. He is a virgin and has never done anything sexually with a guy until me including kissing. I have showed him a bunch so far like kissing, mutual jerking off, oral giving and receiving. He has loved all of the above so far, but I am not sure when I should introduce anal play. I feel ready to take the next step, but I know anal is a huge step for a first timer. Especially since I am well hung hence why I am on this site. I don't want to scare him away from anal because of my size. Does anyone have an recommendations? I am planning to gauge his interest when I see him later today.
 
Let him know what you want to do, start with finger massage, go to rimming, and no more. You've both got time, when he decides he's willing to try, he'll tell you. Just go in very, very slowly, use a hell of a lot of lube, and understand that you are going to hurt him and that you are going to stop the moment he tells you to. Deflowering a girl is just so much easier than deflowering a guy.
 
Hey guys so I have been dating my boyfriend for over a month and it has been great so far. He is a virgin and has never done anything sexually with a guy until me including kissing. I have showed him a bunch so far like kissing, mutual jerking off, oral giving and receiving. He has loved all of the above so far, but I am not sure when I should introduce anal play. I feel ready to take the next step, but I know anal is a huge step for a first timer. Especially since I am well hung hence why I am on this site. I don't want to scare him away from anal because of my size. Does anyone have an recommendations? I am planning to gauge his interest when I see him later today.
You have been dating him for over a month...why rush things?
 
Well you can introduce butt stuff in a different number of ways. For example; dry humping him while jerking him off. Or if he wants to do the fucking then you grind you ass on him while jerking off. And if he's still shy about penetration you can simulate it by just making him close his legs and you slide under his balls between his legs. The taint is pretty sensitive and feels great, at least to me it does. It won't be true penetration but it might get him used to the idea of a guy physically on top of him. It's all about patience, really. Ask how he feels but not too often to make it sound tedious or redundant. I hope you find a way to open up in a reasonable manner!
 
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Why not ask him about some of his fantasies. Perhaps he is fantasizing about getting fucked. Perhaps he is fantasizing about fucking you. You didn’t mention that you getting fucked is an option.

I like both. I was thinking about asking him what he usually likes to watch porn wise to gauge what hes open to trying.
 
I think the key here is to TALK! As you have already had horny times together and he is aware how big you are then just talk ,relax and enjoy the journey together. I would not agree that breaking a girl in is easier than a guy IMO.I have broken 2 girls in and the 1st took 4 sessions before the pain stopped for both of us. Buy DO use a good lube -Astroglide is terrific. Be happy!
 
in 30 years I've been with 2 anal virgins, I was upfront with both in that I said I like anal sex and would like to do it with them. Patience is the key, let them play with your dick, get used to how big it is, play with their ass, get them used to having their asses touched, kissed, rimmed, fingered just lightly, an he'll tell you when he's ready. With one guy it was relatively easy, he wanted it and was more than up for it, the other guy was a built Asian guy, smaller than me physically but had a (very) tight muscled butt so it took a couple of months and when he was finally ready I laid on my back, let him take control holding my dick and lowering himself on to me, he could then control all the action and I think giving him that control was the key. It took another couple of months for him to really get used to taking dick and properly enjoying it.

So just let him guide you, but if you want anal sex with him let him know.
 
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Sadly this post is now a moot point as we broke up. Nothing related to the sex since I never got a chance to even bring it up. He was not ready for a "next level relationship" whatever that means. THanks for all the advice everyone. Back to the single life for me sadly :/