Depends. Are you the kind of guy who blows a load almost instantly? The kind who can't get it up due to stress?

None of it matters. Just have fun and make sure you're both comfortable. Take your time. You probably know enough from ze Internet about what women might actually like. Feel free to ask her what she likes.

Remind her that it's your first time, she'll understand if you're nervous and the problems that may arise as a result.

Thing is, it'll probably be awkward if it's your first time with a person, regardless of whether or not it's your first time period. If things go awkward, just laugh it off and move on, there'll be other times if it's serious.

It won't go as planned, it won't happen like you imagine it. But it will most likely go well.
Pro tip: Trim your fingering nails. They aren't always comfortable if you don't know your way around.

It'll be awkward and weird and very satisfying and then awkward again. Like any other first time ever.

Hey, chances are she ain't a Casanova either. Just relax.

Thanks, guys. This is helping me chill at least a little bit more. However, delve into >>266913 's question.

I haven't really told her it's my first time, not to be an asshole, just out of pure embarrassment I guess. I'm certain she wouldn't give a damn if I did tell her, but it's still tough to cough up for me.

Any insight here?

>>266909
Don't forget to bring cotton balls

>>266920
Don't spring it on her on the night. Give her time to think about it, process it, and maybe modulate her expectations. The next time she drops a big hint, you gotta tell her. I assume, since you are on a chan, she likes you because you are a big bashful nerd, so there's no shame in owning up to it.

If you want extra ~romance~ points, tell her you wanted to have your first time with someone you truly cared about, and you really think she's that girl. Which I hope she is, because it'd be a really shitty thing to lie about.

>>266920

Just bring it up if conversations ever lead close enough. If the subject starts delving into the relationship or what she wants to do in Vegas or whatever, just go "Oh, I keep forgetting to mention this, etc." Don't just bring it up out of nowhere to start a discussion, it'll make everything awkward, instead bring it up while you're both already gushing.

>>266922
... heh heh...

deal w/ it

>>266932
Anon will now commence to have sex for the first time with sunglasses on.

If you are careful and treat your first time as a first time then it should lessen the awkward a bit.
Be honest.
Don't go in there pretending to know what you're doing.

Thanks again, /baw/. This is helping me out quite a bit. For your kindness, have a chainsaw-ferret .

Good luck.

>>266941
I lol'd. What is that from?

>>266945

http://www.youtube.com/watch?v=0yfLD6E_5W8

>>266909
The akward and awful is the best part.

>>266947
Haha, that was great. Don't you just love commercials that have absolutely nothing to do with the product they're selling?

>>266949

How so?

Calm down, and maybe fap beforehand. And play safe, Anon. ^_~*

>>266952
Okay, remember back to when you were like, 12 or 13, and you discovered how to be master of your domain? Remember how awesome that was when you first discovered that in your undoubtedly akward and awful way?
Now, I'm going to assume because you're a virgin you're still master of your domain. It's not that great anymore is it? Even though you got probably a lot better of an idea what you're doing now.
It's the same way when you're with a girl. The first few times are akward and awful. You're going to do things that are going to piss her off. You're both going to do things that leave you wondering what the hell the other person is doing. And thats what makes it magical. It's something we're reminded of every time they come out with a new Pokemon game: Stuff is never quite the same as when it's new and exciting.

Essentially theres nothing to worry about in this situation. Either she's a virgin too, in which case enjoy the exploration together, or she was, at one point a virgin. Which means she knows exactly where you are and will not think less of you in the least for this, unless she's a total cockweasel.

>>266957

>>266959
I don't know what that reaction face means.

Also, if you smoke weed, do so beforehand. It makes you last for-ev-var.

>>266961
And on that note, try to avoid overdrinking. Nothing puts the cabash on your first time like whiskeydick.

>>266963
>whiskeydick
This word amuses me greatly.

>>266963

I don't drink heavily, so I think I'm ok there. Only a drink or two, nothing major. I just go for a light buzz, I hate the feeling actually being drunk.

Oh sweet, I have experience with this. I had the wonderful opportunity to deflower my now-husband.

Not that I had that much experience myself, having been with only one other guy before that. But still.

It was great, I adored his nerdy demeanor, and we enjoyed the time even though the sex was so-so and he had a hard time keeping it up due to being so nervous.

What he lacked in stamina and skill he made up for in heart and trying his best to make sure I was still satisfied.

Just remember. Sex isn't everything. She's obviously not with you just because she hopes/thinks your a god in bed. She'll probably be patient and understanding. It's fun to learn what each person likes.

Let us know how it goes. Interested minds want to know.

>>266966
And then I'll pay someone to make a comic.
Again.

Just go down on her and she won't care.

>>266966
>>266967

I'll do a follow-up when we come back on the 30th, sure. Thanks again for helping out guys, I appreciate it.

>>266969
This.

>>266969>>266976
Yeeeaaah, my advice was going to be along these lines.

ahem

FOREPLAY IS IMPORTANT I CANNOT EMPHASIZE THIS ENOUGH!

But at the same time you don't wanna overdo that too... Which you can, trust me. Timing and awareness of your partner is key.

>>266969
>implying a virgin would even know

Red, come on bro like really.

Unless you're like a secret master or something anon, then UNLEASH THE FURY

When you're done, post a picture that sums up how she feels on the inside.

Remember to bring condoms.

DO NOT FORGET THE CONDOMS!!

CONDOMS, Do NOT forget to get them!

Seconding the "go down on her like the Titanic" motion. Not sure how? Once you find her clit, trace the alphabet backwards and forwards with the tip of young tongue while finger banging her (and for the love of god don't get too rough, some women's clits can be so sensitive it's actually painful to stimulate it firmly or even directly). Try and stimulate the vaginal wall closest to where your face would be, I think the g-spot is around there somewhere.

Also, Kegel excercises increase stamina and orgasm intensity for men as well as women so although it's probably too early to make a difference now, keep it in mind for future use.

>>266983
I always imagined that your advice would involve more eating related quips and possibly concerns about vagina dentata.

>>266963
Like trying to play pool with a bungee cord.

>>266985

Well, I do have to get out of the monster stereotype every now and then. I also need sleep.
Besides CONDOMS haven't been mentioned yet.

>>possibly concerns about vagina dentata.

I believe this will cover any and all concerns about said subject.
http://www.teethmovie.com/home.html
....
......
CCCOONNNNDDDDOOOOMMMMMSSS!

>>266981
>UNLEASH THE FURY

Is still being a virgin at 22 all that terrible?

>>266995
No. Being a virgin at say... 30 and reaaaaally wanting to not be a virgin is pretty terrible. 22 is still rather young. It's just harder to find partners who are also new to the game so it can be daunting.

>>266998

> It's just harder to find partners who are also new to the game so it can be daunting.

Ahhh, that makes sense. I wouldn't sweat it so much, OP, just be honest with her and I'm sure she'll understand!

>>266981
It's not that hard. Tooth's advice is pretty good, but I would even put off the fingerbanging.
But here's the key - firstly, after being the awesome guy willing to go down on her after, even with your mouth up her vag, this is very important - ASK. HER. WHAT. FEELS. GOOD.
If you just head on down and go to town, you're going to end up going a lot of stuff that just doesn't work her. And then it's just going to end up with her getting bored and you getting tired and it'll suck.
Pause occasionally, ask her what's working and listen. Work in the fingers when she's ready. It'll end up being great for everyone.

also, there are instructional videos online. Not porn. Like, actual instructions.
Honestly, if you're that nervous about it try just sticking to oral/hand sex for the weekend - it's better for her anyway, normally, and you wont have to worry about performance.

>>266995
No, it's not. You choose when you want to lose your virginity and with whom.
I think everyone wants to make their first time memorable experience. Something to look back on with fondness.
OP here is saying that his girlfriend has decided it's time, but he has no experience to provide her with maximum pleasure.
So he came, not to suggest that being 22 and a virgin is a bad thing, but to seek knowledge to make sure that their first time will memorable and enjoyable for them both.
So I bid you luck and happiness, OP.
Luck and Happiness.

>>266949>>266952
I think it's more about after the awkwardness is gone. Because it's reassuring that you passed that moment.

Lots of good advice here, OP.

Another thing to remember: it's not all about sticking it in. Your first time can just be hands and mouth, and it can still be awesome. Don't go in there with the goal of literal fucking, but go in with the goal of both of you getting off and having fun. If she really wants it then by all means do it, but don't make it some all-important endgame.

Everyone forgets their first time.

>>267006
What if their first time is the only time?

Alright, so. To sort of toss all the info here in a blender to what's most comfortable for me...

I think I'll calmly tell her about me having never done it (should the conversation head in that direction), I will have condoms with me, when there...I'll probably start by making out with her, then slowly turning to foreplay, asking her what she likes and all that. Then, should actual intercourse be on the menu, I guess I'll just try my best I suppose?

This sound about right?

>>267014
AND HAVE FUN!

>>267014
WHAT DID I TELL YOU?
BRING COTTON BALLS

>>267014
Sounds right. And remember, sex is fun! It's about making both of you happy. Don't ever, ever do it because you feel you 'should'
Also, be as loud as the hell you want.

  >>267017
I think this is appropriate.

>>267014
You'll probably want to stick that in a somewhat intimate conversation that's already started heading towards sex.

>>267016
That wasn't funny the first time. Maybe I missed the joke.

Communication is very important. Think of it this way: if she comes (often and hard) she will be more forgiving of anything you might be lacking.

Also, advice for oral:
Gauge her highs and lows so that you keep her at like, say, an 8 out of 10. Bring her down to a 5. Then up to a 7. Don't switch too often or too low, as she'll get annoyed, rather than frustrated, which you want. Then, if you can, bring her to like a 9.5, keeping her on the precipice. The finally make her come; all that buildup will make it incredibly intense for her.

But yes. Alphabet works, but sometmes it's better to just alternate/change between using the sharp (but gentle) tip of your tongue to laying it flat so that it covers more area. Use both and see what she likes more.

With fingering, hook your fingers slightly in a "come hither" motion. You should feel different texture: this is the mythical g-spot. Either drum your finger on it in a slow tapping motion, or massage it in circles. Tends to work well.

Otherwise, stroke her leg with your free hand (or keep it wandering), or put a hand on her stomach. If she's the bucking type, put pressure on her to keep her down (if she's the type that likes you in control).

Entire thing ends with her meaning "it"==finally watching Penn & Teller live in Vegas

>>267025

"BULLSHIT!"

If you feel like that you'll preform like that, sex isn't hard, don't rush it, remember (in case) that just because you've arrived first doesn't mean you have to stop, you have things other than a penis, remember to consider her pleasure as well as your own.

Good Luck and keep your stick on the ice, I'm rooting for you.

>>267025
Well Penn & Teller is a great show to go to, I saw them live two years ago at the Rio, shit was awesome, got pictures and all that.

So at the very least, OP, you two could have a fun night of entertainment.

So is the girl a virgin too, or is she experienced? Or don't you know? Because oral could be really weird and new for her - to the point where she'd have difficulty getting her rocks off.

May I redirect you to http://www.99chan.in/docta/ and ask people to kindly not bring up this issue again. Ever.

I remember being unable to stop crying after my first time. It must have been hormonal, because I don't remember it hurting that much. Fortunately my boyfriend was very sweet and considerate in trying to comfort me, and I eventually got better about the whole crying thing thing. It took time, though.
I don't know how common that is, and I obviously can't predict how your lady friend will react, but if she does cry, know that there's a good chance it's not your fault. Figured it was something you should be prepared for.
Good luck!

Plusfour-kun I....I.... I want to be with you. This is my first time but I want it to be with you.

All of you. At once. Uguu~

seriously though, op, good luck to ya. Hope it goes well.

>>267056
Alright, we're doing this.

>>267056

>>267056

>>267056

That's...that's nice.

>>267070
Shut up Othar, You're joining in on this.

>>267056

>>267056
Well, it's gonna hurt you more than it'll hurt me

>>267056>>267057>>267058>>267066>>267070>>267072>>267076>>267087

>>266979
This.

Foreplay is 99% of all of it.

>>267056
<3 Oh god I've wanted you for so long Miley-chan. this is going to be my first time too and... Oh no I haven't even-! Kitaaaa!!!

Oh I'm so embarrassed... ._.

>>267107
I can't even keep it up with a condom. Feels like I'm fucking nothing at all. ._. Good luck.

Anyway, it's like riding a two-legged sex bike. You'll be fine.

>>267107
never used a condom

>>267109
Feels, like I'm fucking, nothing at all...nothing at all...nothing at all.

>>267109
> Feels like I'm fucking nothing at all.

I feel like that erryday

The best thing you can do is laugh at yourself. Ask what she likes, but also DONT BE AFRAID TO TELL HER WHAT FEELS GOOD.

So she's better at sex than you? Fine. Make her feel like a fucking champ.

"Baby, that's amazing."
"Never felt so good."
"Oh.. OH... God.. you're the best."

Girls like that shit. Also stop calling sex "it" you fucking faggot.

>>267116
>Girls like shit like that.
Seconding this. In my experience, it's really nice for the girl, and it at least does more good than harm.

Don't call her "mommy" half way into it.

Just...it needs to be said.

>>267121
And people think Freud was a stupid man.

>>267021
Clone High reference.

>>267116
If my man tried to stay stuff like that...I'd be unimpressed. The 'feels amazing' stuff is okay, but don't try to pass the girl off as some sort of sex goddess.

>>267123
I said you smell like mummon! Its a rare Egyptian flower.

>>267139

Ha ha ha. Wrong.

>>267142
I can vouch for TMC. My pet cat loves hearing "You feel amazing", "You're so tight", etc.

>>267141
>>I said you smell like mummon! Its a rare Egyptian flower.

Or its a Digimon.

>>267142
>>267144
"Well. I guess they have ONE thing in common."
"What's that?"
"They both go to the same place for pussy."
"DOOOHOHOHOHOHOHO"

>>266983
Oh, back to condoms. Don't put it on until you're sure you need it. Like it's time to actually penetrate her.

And in case you get a bareback blowjob, a good idea is to eat sweet for a couple of days before, like hard candy or grapes, and as little fat or meat as you can. It will make you taste sweeter.

>>267147
Pineapple is good too.

Truly this is the most cringeworthy thread.

Walk in with shades. The rest should be history.

>>267171
Only when the virgins chime in with "advice". I don't ask guys who watch Kung Fu movies how to fight but they chime in anyway whenever I talk martial arts.

>>267171

whats sex?!?!?!

>>267174
You see when a sow and a boar love each other very much the sow goes into heat and the boars murder each other to stick there dick into the sow for a few seconds. There's a lot of biting and scratching of the sow and eventually the boar gets bored and wanders off to leave the sow to raise his offspring, which he'll probably try and kill if he ever sees them.

>>267171
>female sex organs

bro you have to tell us how it went ok??