First time sex in a relationship

If it was me, I'd give him a blowjob first and see where things go from there. If you want to have full blown vaginal sex, then do it.

 

I don't think there's one ''good time to wait'' before having sex. All that matters is how you feel about it. If you're sure that you are ready and want to do it, then go for it! If you have any doubts, wait. Six months of waiting can be torture for one person, yet another person may need a lot more than six months to be ready. Just go with your feelings! Nothing's wrong as long as you're sure

 

Use a condom.
...
USE A CONDOM!!!

 

Why do so many people assume that you have to try to swallow it? Giving a blowjob is not the same thing as deep throating!

I dont have much experience so its probably best to ask someone else but I'd say that you should use your tounge to stroke the head of his penis.

 

The advice on "waiting" mainly has to do with getting comfortable with the person, and feeling you can trust them with letting them see what I call the "quivering gelatinous underbelly". You know, not just seeing you without clothes, but without inhibitions. The fact that you've known this guy for a couple of years, and presumably feel comfortable with him, assumedly means you're at that point. So don't feel the need to wait any longer if you'd rather not.

Random tips as I think of them.

* Ask what he'd like to do. I know it's probably a given that he'd like to do vaginal, and probably get a blowjob, but why not find out? Tell him what you'd like to do, and ask what he'd like as well. If he's not up to speed yet, let him set the pace. If he just wants to make out heavily, do that for now.

* A blow job isn't "see how much of it you can fit down your throat at once". It's making him feel good using your mouth - that's it. So feel free to give it a try. Kiss, lick, suck, whatever. Pull your lips around your teeth before you take him in. Stroke the rest of his penis with your hands while you lick the head. Stimulate his scrotum with your other hand.

* Here's a good thing to keep in mind. There's a spot about a half-inch behind the head on the underside of the penis. There tend to be more "pleasure points" here than anywhere else. There won't be any visual sign of where it is, really, but just know it's there. Any step you take away from that spot tends to be SLIGHTLY less enjoyable when stimulated. So underside more than the sides, sides more than the top, that spot more than the tip, that spot more than the base. This doesn't mean working the base or the tip won't be enjoyable to him - they will be. But if he seems to be getting a bit over-excited, move your tongue to the top of the penis. Or towards the base, or to the tip. If he seems to be plateauing or slightly losing interest, move around more, and hit that spot more.

* Protection, protection, protection. Don't start playing the "I know I'm clean" or "we'll be careful" games. Condoms condoms condoms. Putting a bit of lubricant on the inside of the penis (along the bottom edge) will make it more enjoyable for him.

* Have fun, damnit.

Lex

 

Personally I go by my religious beliefs and wait until marriage but I understand many people definitely don't want to wait that long. To that I say, wait until you think you're comfortable going all the way and make sure your boyfriend is too.

 

Inside.

Also, in case you didn't know this, if you're gonna do oral with a condom, you might prefer unlubricated or flavored condoms, because many people find the taste of lubricants gross. And of course if you decide to go all the way and have actual intercourse, you'll need a new one -- this time lubricated.

Have fun

 

Both inside and out would be good.

The relationship dynamics do usually change. I have noticed that I am more comfortable around the person, and have that "I've known you my whole life" feeling. I mean it is an incredibly intimate and powerful exchange of energy when you have sex. If one of you feels weird about this afterward, it can make things difficult. It comes down to whether or not you want to give that much of yourself to this person, and if you trust them to reciprocate. I am talking about a certain kind of sex here though. Hook-ups and one night stuff usually doesn't bring these deeper feelings out, but it can take the sexual tension out of the relationship nonetheless.

I don't think that there is a time limit. I would say that it is more about what you want out of the experience. If you want someone who isn't going to just fuck you and leave you then wait until you are sure that the relationship is pretty stable. If you want to just get laid, without having someone stick around and annoy the shit out of you then don't have sex with someone who you are always hanging out with.

Have an honest talk with each other before hand to figure out what each other wants and needs, and also any boundaries. This means both in the bedroom and in your relationship. Be certain to have a clear understanding of what each other thinks is okay as far as sex outside the relationship.

Safe sex, emotionally and physically.

 

Well, I would personally wait a little to get closer and fall more in love so when the time comes it's even more amazing. But it's up to you, there's no right or wrong anyway. Do what you (or your vagina ) want.