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» Scarleteen Boards: 2000 - 2014 (Archive) » SCARLETEEN CENTRAL » Sex Basics and Sexual Health » First time, condom issues, etc

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Author Topic: First time, condom issues, etc
Member # 21720

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My boyfriend and I have been together for quite some time now (almost a year), and we decided to take the next step and have sex. Unfortunately, we had quite a few problems. My boyfriend tried a couple of different condoms, and both were extremely tight and very painful for him. As a result, he was unable to maintain an erection (granted, part of this was probably also due to the fact that we were both nervous).
Penetration was very difficult, despite the fact that I was aroused and we were using a lot of lube. We tried several times over the course of a couple of days, but he was only able to fit the head of his penis... and he kept sliding out.
I guess I'm asking for advice on a couple of fronts... for starters, some condom suggestions for my boyfriend, because this is suppossed to be pleasurable for both of us, and we refuse to try without condoms (despite my being on birth control). Any other advice would be greatly appreciated. Communication isn't a problem with us, since we've talked this out, know what we're doing, and there isn't any pressure on any of us to get it to work immediately...
Also, we're currently using astroglide, but it wears off quickly and sometimes burns me a little bit. Does anyone have any other suggestions for a different lube?

Thank you very much!

Posts: 29 | From: NY and Boston | Registered: Jan 2005  |  IP: Logged | Report this post to a Moderator
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Actually, while pain would inhibit erection, tight pressure usually does the opposite. But that's academic.

Good on you both for taking a stand with condoms. Sounds like -- since the shaft of a condom tends to be REALLY stretchy, no matter the brand -- you might want to try a condom with a larger ring size. Durex makes a larger sized condom, as does Lifestyles. It'd be a good idea for you and/or your partner to buy a nice big box so he can try putting them on and wearing them for masturbation alone -- away from the nervousness and pressure anyone is likely to feel when trying something new with someone else, no matter how much they like them, and no matter how great your relationship is.

Per your issues, really, it'll likely just take time: what's going on is likely due to all these factors -- his erection issues right now, the condom discomfort, both of you figuring out how intercourse works, etc. Like you said, there's no hurry, and that's FANTASTIC. There shouldn't ever be for anything sexual. I'm actually guessing the lube is burning because of microtears to your vaginal opening (normal at first), and because of pre-existing irritation due to the penetration attempts. Astroglide is pretty gentle because it's water-based, but you might try a lube with a littl less glycerin like LiquidSilk if that keeps being an issue.

So, might want to "try" a little less for the time being. It might also be helpful to pretty much leave intercourse for dessert, if you follow me, engaging in other sexual activities together for pleasure and leaving that for the very last thing when you do attempt it.

One last thing: it ALWAYS makes my day to hear from a user really approaching sexual partnership in a patient healthy way AND with their own health and safety in mind. Give yourself a cheer!

Heather Corinna
Editor, Founder and Head Hussy in Charge
ST homepage ST blog about Heather & Scarleteen

Posts: 68290 | From: An island near Seattle | Registered: May 2000  |  IP: Logged | Report this post to a Moderator
Member # 21720

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Thank you Miz Scarlet.

We actually were trying Durex XL, along with Trojan Large... neither were comfortable in the slightest for him. And as you say (and kudos for finding an amusing way to say it), we do try leaving sex for "dessert."

You're probably right that we just have to take our time a little more... and that's not a problem. It's frustrating, of course, but in the end, this is something for both of us and shouldn't be rushed... I guess I'm quite a lucky girl to find a guy who agrees with me on that.

Do you have any other condom suggestions that might work better for him?

Thanks again!

Posts: 29 | From: NY and Boston | Registered: Jan 2005  |  IP: Logged | Report this post to a Moderator
Member # 20990

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Well, I sympathise. Penetration can actually be pretty tricky; it certainly has been for me and my girlfriend.

Getting a whole bunch of condoms and practicing putting them on is a very good idea; I don't think I would ever have managed without that. I assume you've read the condom how-to at Scarleteen -- I had too, but it still took quite a bit of practice.

I found that I sometimes have very dry skin on my penis, and the condom, or indeed anything else, could be very irritating -- unless I put a little lube over my whole penis first, in which case it's fine. (Not much lube, so the condom still goes on tight and doesn't slip, isn't in danger of coming off, or anything; this is for mosturizing.) I mention this because the dry-skin problem feels sort of like the condom being "tight". I also had to be careful about public hair, which kept trying to get trapped in the condom. :-P

Trawling the board, I found this thread, with lots of comments by Miz Scarlet:,
This also mentions the actual width measurements of some condoms:
Apparently Trojan is somewhat deceptive in their marketing. And Miz Scarlet doesn't think much of their quality, either.

This site also has some suggested condoms listed at . (But note that the link for MAXX is broken, apparently because has stopped carrying them.)

I also discovered that sells 55 different specific measurements. (!)

Wow, I just learned a lot from searching this site. :-)

Of course, he *could* be really, unusually big -- if he's more than 2 1/2 inches in diameter (width across), for instance, you would really have problems finding comfortable condoms. That's unlikely though.

As for slipping out after getting just the head in, it just takes practice. I must have slipped out dozens of times the first time I and my girlfriend tried penetration. If you can laugh about it and find it sexy, then that's OK. :-) Some positions might be easier to "figure out" how to line things up in, for your first time, than others.

We ran into and dealt with yet further problems, but they are probably not relevant to your experience and this post is long enough already.

[This message has been edited by N (edited 02-05-2005).]

Posts: 37 | From: USA | Registered: Nov 2004  |  IP: Logged | Report this post to a Moderator
Member # 21720

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Thank you, N. Our basic attitude as of now is to keep trying, but there's no rush. We've run into our fair share of problems too, but that's another point entirely. We're just taking our time and enjoying eachother's company and affection. And yes, we were able to joke around about our first few tries.

Thanks a bunch!

Posts: 29 | From: NY and Boston | Registered: Jan 2005  |  IP: Logged | Report this post to a Moderator

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