SL Letter of the Day: First Timer


I find myself wanting to know how this turns out.
A LITTLE BIT of that champagne might help before too, wouldn't it?
@2 one stem would be just about right...
Margaret Cho tell you to walk up to the guy and say: Hey, um yea.. Stick it in!
Be sure you take a sense of humor. It may come in handy. Most importantly, just enjoy yourself.

We want a report.
@2/3 are good suggestions. You'll be nervous, so try not to do things that stress you out more.

Yes, it will get better.
As a straight guy, I've turned away thousands of virgins who showed up at my door without something for stain protection.
Who says "heavy petting"? Are we in health class?
Have a great night! From a straight girl:

I think a *little* bit to drink might not be a bad idea - like above, maybe a single flute of champagne (depending on your tolerance - if one flute is enough to knock you on your ass, then just go without).

Also, I don't know what you call 'heavy petting,' but: get something up there before he gets his dick up there. Fingers, vibrator, whatever. Hopefully, you'll climax, which will loosen everything up a bit. And if not, you'll still get prepped for penile penetration. And the whole cultural thing about bleeding on a girl's first time is vastly overrated. If you bleed at all, it'll probably be a few drops at most (especially if you've already played around with fingers and dildos, or were incredibly athletic). It's far more likely you'll get lubricant on his sheets than blood (yeah, I know, someone will pipe up here and talk about geysering blood their first time. They are outliers, not the norm - and the norm being the norm, you're far likelier to adhere to that than not).
@7: I've found that a clear "No stain protection, no service" sign on the front door helps immeasurably.
The bleeding is usually very minimal. If you get any on the sheets, just wash it in place with a washcloth and COLD water.
You're probably more likely to get blood on sheets during a period.

But there may be a big wet spot afterward. :-)

I do remember it hurting a bit, but I was only 12 at the time.
Take it easy and have fun.
@10: I keep my sheets in plastic slipcovers so they stay pristine.
Make sure he has a penis.
I don't know about anyone else, but my first time sucked. Not because it hurt [which it did] but mostly because it was awkward.
I imagine it would've been different we hadn't BOTH been virgins, though. We were so inept.
#2, NO! Pop the cherry, then the champagne cork!
Love "Dan the matchmaker."

@14--my first time sucked, too...but that was primarily b/c my parents came home in the middle. Thank goodness we had a dog that barked when he heard the garage door go up! (You can guess, though, what the guy was still wearing under his clothes in those post-dance photos my parents then took!)
I think it's advisable to use a waterproof mattress cover under the sheets anyhow, unless his mattress is already uglified. Even when you don't plan on bleeding on the sheets. I've seen mattresses with some seriously grody sweat stains. I'm not talking about like a rubber sheet or anything extreme, just the pretty-much-waterproof fitted sheet things they have at Target.
Only suggestions:

1) Have fun

2) Abandon expectations (doing this will help you with the first suggestion).

What 25 year-old, virgin or no, still has a hymen in this day and age?
@18 seconding both points (and that 2 will help lead to 1).

Don't stress afterwards if it wasn't THE MOST AMAZING THING EVAR. It gets better every time.
Inebriate and lubricate.
Can you do this at your place and then the clean-up will be on you and you won't have to worry about how he feels about his sheets? Other than that, how exciting. I wish I could have a first time again, so much anticipation and fun!
Am I the only one who wants to keep my sheets and mattress as stain-free for as long as possible, much less someone else's?? Besides, putting down an old dark towel also gives me somewhere to wipe the excess lube off my hands. As for bleeding, I didn't until my third time (girl-on-top did the trick).
Fuck the sheets - you don't bleed galleons of blood! Maby a tiny drop or two - I didn't notice anything at all my first time!
My first time (w/a guy) was fact, it was one of my best ever experiences. I tripped out on the "physicalness" of it all (I'm a more "mental" type of person). It did hurt, but I got used to it. And I'm squeamish about pain. He was very careful, and after entering, he just held still until I got used to it.

If I'd been w/more guys like that, I prob wouldn't have tried women.

Unfortunately, it was my only time w/him. Sex w/other guys wasn't as good. With women it was better, but a lot more infrequent. Aside from a mind blowing make out session of a few years ago, I have no sex at all now. But that's another subject...
Don't have an orgasm first -- the muscle contractions can make you very tight. Just make out until you are really wet and really really wanting it. If you just decide mentally "Now I Shall Place This Penis In My Vagina," like you were inserting a tampon, you might have the "Uh, that was it? That's what the big deal is about? Oh." feeling so many women get. On the other hand, if you wait until your whole body is begging for it, you will have a much better experience. Trust me. (You will know when that happens.)

In tantric sex they recommend lots of nipple stimulation first (LOTS). Also, don't feel like he has to have an orgasm inside you if you don't feel like going that long. Too many people feel like that is a requirement. You can get him off in other ways, or he doesn't even have to come at all. He also doesn't even have to be pumping away all the time if you don't want him to -- it can feel absolutely incredible if he stays still (and will give you a chance to use a vibrator or your finger then on yourself if you want).

I highly recommend reading about tantric sex once you get going with this -- a totally different, woman-focused, non-goal-oriented paradigm that can be a real mental health break in a culture that insists (like some capitalist) that everyone accomplish something during sex. Dan never discusses this, but it really is a lot more than hippie/Sting/new age woo-woo, and can be an incredibly healthy thing for both men and women, even if all you ever do is think about it.
The only women I know who've bled at all were the ones who had sex in their very early teens. My best friend and I were actually disappointed because we'd both read a lot of 90s style rape-y romance novels and had assumed that we would have crimson streaked sheets as evidence of our deflowering.
I'm with 14. The first time was awkward and painful. Lube might have helped. Some of the advice above might have helped. If either one of us hadn't been a virgin, I think that would have helped.

I bled, but not much. My husband had hoped to leave enough of a stain on the sheets to impress the hotel staff, but I doubt they noticed.
@24: I don't know anyone who magical currency.

... for the non nerds: Galleon = HP dollar. The word @24 was looking for is gallon.
I, uh, haven't bled yet.

Was I supposed to?

Have a laugh though, because it won't be all romance and hot, squeaky passion! He's going to pull your hair when he tries to move you into position, you're going to accidentally smuck him in the balls with your foot. He could bang your head with his, and you could end up screaming in his ear loud enough to give him a mild hearing problem.

Relax, have a giggle, and don't try to marathon it! The immediate release of post-coital hormones is sudden, your body might welcome them but mine didn't. I got angry, for some odd reason and when he was done I just wanted him OFF me.

Oh, and cuddle. Nude cuddling is fun.
@29 While not dissing Harry Potter, a galleon is also an old European sailing ship. Maybe she meant "boatloads" of blood? And I can personally attest to that one: I didn't bleed a galleon's worth, more like just a small dinghy.
Don't be afraid to laugh!

Sex is messy, noisy, and crude...

Wow, I could have written that letter, so I have a follow up question? Am I absolutely required to let him know it's my first time? I just feel... silly.
I have recently learned that straight hydrogen peroxide poured on a blood stain before washing takes it out fabulously. Bubbles away.
This letter could've been written by me, except I'm 21, not 24, and living in a red area of a blue state. Thanks, Dan (and commenters) for the advice!
@33 I think you should be comfortable enough with the guy who takes your virginity to tell him what he's doing. I understand how you feel (see my comment above), but not enduring this little bit of awkwardness now could mean major awkwardness later on if he realizes you kept it from him. Also, it'll hurt a lot more if he doesn't know to be gentle.
@37: Never say 'anii' or 'penii' again.
As a girl who lost it at 30 and has no regrets (waiting that long, or losing it when I did), bleeding likely won't be an issue that a doubled-up, dark-colored old towel won't take care of. If it's an issue at all. If you've played around with dildoes at all, it probably won't be.

Echoing what some other people have said, use lots of lube and don't expect it to be fantastic. And if you haven't spent a lot of time with this guy doing a lot of really fun things together before now, not only is it probably going to be weird and uncomfortable the first time, it's not going to *get* fantastic any time soon. In other words, don't have sex the first time "just to get it over with." (No indication that's how it is with you, but just in case...)

And nobody laugh at me. I had some lonely years in my teens and twenties, but I can't convey just how glad I am that I waited until my head was screwed on straight. (I more regret how long THAT took.) A few years of Savage Love under my belt didn't hurt either.
Hey all, it's GGG! I just thought I'd give you guys an update and answer questions at the same time.

8: Confluence - Sorry, would "fooled around" have been better?

19: Fistique - My hymen is still intact because when masturbating with vibrators I've never pushed past it. It hurts too much and I don't know about you, but I like masturbation to be fun and feel good, not hurt like a bitch.

37: Lose-Lose

I hesitated to use the word virgin at first but it really did fit the situation. Until tonight I had never done any sort of sexual activity.

1. I plan on taking one of my vibrators with me to help "loosen" me up. I actually have a whole bag of shit, but he says he doesn't mind all my toys. He's very GGG.

2. Tonight I payed quite a bit of attention to his penis. I used my hands, mouth, and boobs to take him over the edge.

3. I'd like to do the long romantic weekend thing, but to tell you the truth I'm just not that patient. I've been waiting for too fucking long. No pun intended.

4. He's given it a nice rub down through the clothing but I'm waiting on him spending more time with my kitty until Aunt Flo leaves town.

5. I like your idea of starting with the kinks but I've decided to go with Dan's advice. After all, he did answer my letter. I squealed like a five year old on Christmas when I saw the link in my email.

Saturday has moved up to Thursday now because I am getting impatient. I'll let you guys know how it went. Thanks for all the wonderful advice!!!
Can't get the image of Daniel Day-Lewis as Daniel Plainview out of my head here. "Drainage! Drainage!!!"
Oral sex is really fun , too! I would have a morning after pill handy in case of spill or break in condom. I don't know about anyone else but my first time still makes my heart beat fast forty five years later!
@ 37 - "each other's anii" ??? You mean some people have more than one?
Echoing the preparation for LAFFS.
A bit of preparation is nice but isn't this overkill? Most of the rest of us just got on with it, and it was good for some of us and great for some of us and okay for others of us. Too much pressure, too much prep, too much drama for me.

Maybe I'm just a crabby old fogy.
didn't read all the comments yet so i'm not sure if anyone else has mentioned it but - did anyone else notice she specifically stated she's an atheist and dan ended his response with "god bless"? a little incongruous isn't it?
but other than that, good advise, as usual.
seriously, everybody, do we have to use the euphemisms? VAGINA, not kitty. PERIOD, not "Aunt Flo." it's like the adult child from this week's i, anonymous took over in here.
@47: I make a point of calling it "MENSTROOOOATION" in my boyfriend's presence.
@ 47: Oh lighten up Amy. I always called my period (back when I had periods) Bleeding Like a Big Bleedy Thing. So fairly literal for an euphemism.
You are displacing your anxiety onto worrying about the sheets and over-preparing. It's natural to be nervous about your "sexual debut".

From what I recall about sex with virgins, if you are on top, it might feel better. You'll be more in control of the depth of penetration and pace.

Try to keep a good sense of humor about the whole thing ... laugh at how totally absurd it is. It's both absurd and beautiful.

I think it takes at least 20 times with one person before you begin to really know someone sexually, regardless of how experienced you are with others. That's when you might let the kink out to play. This is the beginning of a life-long adventure.
I'm happy to see that laughter is such a common component of folks' experiences. I was 24, and a guy (which has its own peculiar set of complications) when I first had sex and I can assure you that laughter, giggling, and just playing around without any expectation of having to slide flap a into slot b is really the only way to way to approach the event. And if the build-up is too stressful to muster up a sense of playfulness and joy, and if things don't quite go according to plan, remember that it will only get better from here on out. Sex is the very best thing in the whole world so have fun!
Gee I don't know, GGG. Are you sure you want to have sex with this guy? I mean, you say you're really attracted to him; that he's "funny, sweet, gentle, and a great kisser", but you shouldn't sell yourself short, you can do so much better! Listen GGG, your virginity is a prize and you shouldn't give it to just anyone. I know you've already waited 25 years for the PERFECT man, but there's nothing wrong with waiting another 25 (or 30) years for Romeo Incarnate to come along. Right now you're a sweet and innocent virgin, but if you lose that precious flap of skin to anyone but your SOUL MATE then you'll be a dirty whore the rest of your life, just like the rest of us. Of course I'm sure you knew all that, having waited so long, I just don't want you to give up the struggle.
Okay, intervention time here. If penetration with a vibrator hurts, sex is going to hurt. It may or may not be an intact hymen causing it - it may just be a really tight vagina.

From how enthusiastic and impatient you sound, it's probably too late to call this off. But if it's not, I'd advise you spend at least a week stretching yourself with smaller dildoes/vibrators, then working your way up to larger ones until you're comfortable being penetrated with something the size of a penis. Whether your pain is caused by an intact hymen or a tight vagina, this should take care of the pain problem when it comes time to actually have sex.

If you do decide to go for it on Thursday, be prepared to be sore for a few days, and expect your bajingo to be out of commission for the duration. If the situation doesn't improve after having sex several times, see your doctor. Also be advised, if the issue is a tight vagina, it'll probably tighten back up if you don't have sex for a while, which means you'll have to start over with the dildoes/vibrators when you want have sex again.
"4. He's given it a nice rub down through the clothing but I'm waiting on him spending more time with my kitty until Aunt Flo leaves town."

Wait. So, it's been less than a week since you've started being at all sexually intimate with this guy? And you have in fact never been naked with him? And now you're planning to get right to the sex?

Am I misinterpreting here? I don't mean this in a prudish way, but it seems to me like you might want to take a little more time to get familiar with each other's bits. It just sounds kind of like you're talking yourself into this before you're quite there. I get that you're impatient, I know exactly where you're coming from, but as others have noted, there's a lot left to do here, and I think everyone can agree that there's a fair amount of ground to explore between "a nice rub down through the clothing" and first-time penetration.

On the other hand, if it feels right, go for it. Good luck!
@53 - I have a friend who was super tight (smaller than 2 of her rather narrow fingers), and just lost her virginity at 25. After that initial time where it DID hurt, she has been fine. I think they waited like 2 days after the first time for the second time and now she's loving the PIV sex.

Someone earlier said it takes 20 times to get the hang of sex with someone - I agree that it takes a while and definitely your fist time is most likely not going to read like a trash romance novel. I usually figure that it takes 5-10 times to get the hang of one person, but then I have been practicing for 13 years and used to get bored easily :-)

Also, I bled, but mostly onto him. For me at least, it didn't really hurt, but it made a weird popping noise that I felt more than heard. Still can remember that.... Anyway, a quick shower for both of us took care of the mess that wasn't picked up with the dark towel. So yeah, checklist:

1) condoms
2) lube
4) sense of humor
3) towels
5) sense of humor
Wow. Preparation and scare-comments unnecessary. Just smoke a bit of weed, and relax. Don't effing plan it.

And the beatles said it best when they said "all you need is lube."
@33, yes, LaPuerta, it would be best. Your prospective partner has the right to make an informed decision. Knowing it before hand gives them the opportunity to take it slow and easy. Finding out afterwards makes them say things like, "I knew something was weird, why didn't you just tell me? I could have made it so much better for you!" So tell him and give yourself every opportunity to enjoy this!
I echo the recommendation for girl-on-top, at least for the first penetration. You have more control over the speed/angle so it hurts less. You can always flip around if you'd prefer another position after he's in.
@40 Thanks for commenting back in, GiggityGirl! I hope that you have lots of fun exploring each other's bodies, and I note with humor your impatience with moving up the date. I also saw with some trepedation how much it hurt for you to shove a vibrator up yourself. Is it at all possible that you can put this off and get that hymen surgically trimmed? or to go ahead and break it yourself? A painfully intact hymen can put a real and unnecessary damper in your first time. Just a thought, and I apologize for putting a shadow on your excitement.


For the Latin-deprived: the plural of anus is "ani"; the plural of penis is "penes". Thank you for your support. I'm now going impale pieces of octopi on some cacti, and then tour some circi.
@33, 36: My first time, I had planned not to tell the guy. I thought 'why bother with the unnecessary embarrassment?' But it became immediately evident that he should know. Because it was quite painful (I hadn't done any "prep work"), and yeah, he needed to know to use care, not plow it.

And in the end, I needn't have been embarrassed, because he was someone I trusted - that's why I'd chosen him in the first place, ya see.
Hmmmm....I'm pretty sure she wouldn't have to worry about bleeding so much if she masturbated prior to losing her virginity. Getting to know your own body first usually takes care of all that.
@61 unless it hurts so you stop pushing with the vibrator. She may have a thicker hymen which will take some force to get through. I wouldnt want to pierce my own ear, either, but I can let someone else do it!
The existence of hymens must give Intelligent Designers wet dreams!
"As for bleeding, well, that's a possibility. You could bring along a rubber sheet for his bed, I suppose, or attempt to place a towel and then check to make sure it stays put. But here's better idea: fuck like you don't give a shit about his sheets. Because in the grand scheme of things, GGG, the damage he's going to do to your hymen is much more significant than any damage you might do to his lousy old sheets."

Um, maybe, but at 25 probably not, unless a) GGG had/has a hymen that mostly covers her vaginal opening (rare); b) has led an extremely inactive life; and therefore c) her hymen has not worn away of its own accord, through hormonal weakening post-puberty and daily friction from walking around, bicycling, rubbing or penetration during solo or partnered manual/oral sex, tampon use, etc. For many women, bleeding the first time or first few times they engage in vaginal penetration is due to VAGINAL (and not hymenal) tearing, due to a lack of arousal/lubrication from nerves about it being the first (few) time(s). In fact, the hymen does not typically have any arteries/veins running through it that are large enough to cause noticeable bleeding even if it does tear, though it's also perfectly normal if it does (this is more common with an imperforate or microperforate hymen, which should be excised by a medical professional for safety's sake). The hymen is extremely elastic, particularly after puberty, so even if it hasn't worn away, it can and will stretch around objects inserted into the vagina. A little fewer than half of women report bleeding the first time they have penile-vaginal intercourse, and a good portion of them are experiencing bleeding due to a lack of arousal.

GGG: I agree with Dan that you shouldn't be concerned about bleeding, particularly since it's likely to be minor if at all extant, unless blood is a major squick for your guy. Hell, I have a few tiny blood spots on my sheets from cuts I didn't notice, bug bites, etc. I'm guessing most people do; unless they're super-OCD about their sheets or really squicked-out by blood, they're not gonna care. If you DO gt a little blood, just wash the sheets (in COLD water) with some bleach (color-safe oxy-stuff if sheets are colored), and it should come right out.

Go check out; they even have a first-time vaginal-penetrative-sex checklist somewhere on there, as well as great general sex/sexuality/sexual-and-emotional health information. And a lot of the staff (and the creator, who writes lots of articles for and answers lots of questions on the site) have vaginas and are a bit better-informed about them than Dan (who, by his own frequent assertion/admission, is not an expert).
50 mentioned this, but nobody else has really touched on it--if you hadn't talked about it with your doctor, you should know that it's actually a really simple, short operation to just get your hymen cut for you, allowing both the vibrator and the first-time-guy to be able to go in without having to make it painful for you. I don't know if the Idaho redness extends to medical professionals in your area being unwilling to talk about this sort of thing, but in my area (middle-of-nowhere Iowa) my best friend was able to talk to her doctor, go in, come out, come. She said it wasn't anywhere near as traumatic as having oral surgery for braces. I can figure if you aren't close to your doctor (my friend and our doctor are pals, she babysits the doctor's kids) you might not have felt comfortable talking to her/him about this, but bringing it up can't hurt, and having it done might *really* not hurt, if your hymen is as tough as you've described.
Oops, that should be 59.
I was a similarly late virgin for basically similar reasons. When I finally decided to sample the waters, it went fine -- no orgasm, but plenty of fun. Based on my experience I would say that with lots of pre-sex foreplay and lots of lube (and a partner of average endowment) and it should be fine. I recommend investing in a red towel, however. Can give you peace of mind the first time if you position it under for the act and you can use it to clean up after. And a dark burgundy towel will hide most stains you're likely to encounter down the road.
From another female going through something incredibly similar, the best advice is to do as much as you can to relax your muscled. Vibrators are great. A hot bath befor would help as well. I also reccomend tons and tonds of lube. Try out the lube BEFORE you try intercourse. You don't want to find out in the middle of the act that you are alergic to something in it.

I also reccomend you being on top. Squat onto his penis and try to let the weight of your whole body help push him in.

Have fun!
I'm kinda surprised no one posted a link to this yet:…

Maybe you can contact the author and tell your story, too!
@59, octopus is actually Greek, and therefore the plural is "octopodes." Pedantic moment of the day :)
@70: Zing! :P

I just never understood why people couldn't be content with "octopuses." I think it's a nice way to acknowledge that yes, it is an English word now. We've adopted it and made it our own, and the Greek form can remain whole ... in the *Greek language.*

We don't say "stadia" or "podia", though we could. And everyone keeps calling multiple pressed Italian sandwiches "paninis"! "Blonde" goes for men and women, even if it's the feminine form in French! I mean, people. Either you're a stickler for foreign forms or you're not. Bah!
@71: I use "blond" for both men and women, even though I'm fairly fluent in French. XD
@56 - Giggidy said being penetrated with a vibrator hurts. Stands to reason being penetrated with a penis will too. "Smoke some weed and relax" didn't seem like the right kind of advice to give under the circumstances.

And a whole lot of people here are assuming hymen = pain, no hymen = no pain. It's not necessarily true. My hymen was long gone when I had sex for the first time, and it still hurt. I figured out through trial and (painful) error that my vagina is naturally pretty tight and it needs regular penetration with a penis or a penis-sized substitute to keep it "in shape" for easy and pain-free sex. Once I get it there things are great, but getting it there is something I have to take a little care with.

I honestly have no idea how common this is, I just wanted to give Giggidy a heads up in hopes of saving her a few days of soreness. And I'm pretty sure my advice in 53 applies whether her pain is hymen related or something more similar to my issues.

Of course, since I'm unregistered I could just be talking to myself here.
@70 I think 59 was kidding about octopi & cacti -- it was a joke about incorrect "Latin" plurals.

My personal bĂȘte noir is "syllabi." It looks ridiculous. Just call them syllabuses, people.
Um, wow, I think you're way overthinking this.
sooo did you do it?