kinda apprehensive about sticking the thingy in the hoo ha

If you use contraceptives (including but not limited to condoms) the way they say to on the packaging you should be fine.
Especially if she's on birth control. When used correctly it's like 99% effective.
And use lube, it'll help with any sticking that could compromise your condoms.

So, as long as you're being careful, you should be in the clear! It's okay!

 

Also, make sure that you use silicon-based or water-based lubricants if you use one. Not Vaseline. Vaseline doesn't work with condoms at ALL.

 

Contraceptives generally work. Combined, they work really freaking well. It's like gun safety. One safety measure is generally enough, but when put together with the rest of them, failure is functionally impossible.

 

I don't mean to scare you...but as one sex book pointed out, if a couple moves to penis-vagina sex, they have to be ready for the possibility of unplanned pregnancy.

On a practical level, using multiple forms of birth control at once should drop the chances rather dramatically. This means you use a condom (And by the way--do not--and I repeat do not--use two at once. That will actually increase the chances of something going wrong.) Water based lube, as mentioned above, might help.

Meanwhile, your partner should use something.

Another thought: perhaps you might be happier waiting to have vaginal intercourse. There is no reason why you should feel forced to do it, until you feel ready.

---------- Post added 29th May 2013 at 11:43 PM ----------

This one line concerns me. If you don't know for sure she'll be using birth control of her own, I don't honestly think the time is right for you two to have sex. You need to have an honest discussion about birth control, and come to decisions before even thinking about sex

 

Yes the risk is always there, but with both a barrier method (condom) and a hormonal method (le pill) you're as safe as it gets.

As mentioned lube helps and be sure to put the condom on before the thingy gets anywhere near the hoo ha, as precum can contain sperm.

When I was sleeping with men I made sure I explained my feelings on abortion and how I would handle an unplanned pregnancy. I know that isn't a conversation most people want to have when things are starting to get sexy, but it helps knowing if your on the same page if the "worst" happens.

 

I mean, of course, do not use 2 condoms at once.

Do use at least 2 different types of birth control--a condom on you, and your partner doing something like a hormonal birth control.