Unfair to ask a female friend?

Barely Big

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I have a long time (over 10 years) close female who I know has been/is sexually active. I myself am a virgin and we never discuss such matters except maybe briefly in passing, usually in a joking context.

I have a question pertaining to sex that I'd like her advice on because I know I can trust her no matter what she says. I know I could ask the board, but there's something to be said about the word of a long time friend that trumps the advice of people over the net who I don't know at all. The thing is that I've never really talked to her about anything even close to the subject and I feel like it might be kind of unfair to her as a result. I think that subconciously I kind of want her to think of me sexually, but am too ashamed to actually admit it to myself. I would like her to find me attractive, but just as I'd like all women to find me attractive.

To give more context on our friendship: We're both over 18 but under 20, been friends since the 2nd day of kindergarten. We dated really briefly in jr. high, realized that in jr. high dating is pretty much just being friends but acknowleding attraction to eachother and then broke up. I know I'm still attracted to her some, and have a feeling she still is some towards me, but we both value our friendship way too much to take a chance with dating. We recently decided that she is somewhat of a sister/girlfriend combination without the gross incest thing.

My only solutions to this quandry as of yet are to not ask her at all or asking her if she would mind fielding a sex oriented question and going from there.

It really comes down to: Is it unfair to her to ask a sex related question if I have doubts of my motives? I do really want an answer to the question, but I am trying to be the best friend I can at the same time.
 

Lordpendragon

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I think that you are going to have to tell us the question - it might make a big difference to what people advise. Does she know that you are inexperienced and that you know that she is not?

These things are awkward at your age, but quite natural for friends and your friendship will have to deal with the developments in your lives.
 

sares

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Lordpendragon said:
I think that you are going to have to tell us the question - it might make a big difference to what people advise. Does she know that you are inexperienced and that you know that she is not?
that's pretty much it. I can't personally promise no one will be a dick (as it were) about your question, but I certainly won't. it's just that there's such a huge difference between something like,

"hey Friend, I really need to ask you a question about sex, is that okay... all right... is it really difficult for girls the first time?"

and

"hey Friend, I really need to ask you a question about sex, is that okay... all right... what kind of foreplay do you like? show me!"

I kid, but you see what I'm saying. so I can't judge what her reaction could be, or put myself in her mental shoes, until I know what the question is.
 

Barely Big

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Spladle said:
Oh my God. Stop thinking so damned much. You're gonna give yourself a stroke.

This made me laugh and realize how absurd the whole situation is. I am probably way overthinking this thing.

Yes, she knows that I am totally inexperienced. She has in passing told me of her sex life as either good or bad, but without any other details. She is (of my friends) the most willing to talk about sex and I know she is very concerned with sex safety.

What I want to know is: how far down to the body should a condom fit? Should it be flush (or almost flush) against the body or is it supposed to not cover the whole penis?

Clearly this is a question many on the board can answer, but again I am much more trusting of the advice of a long time friend than an anonymous name over the net. And before anyone asks, I've tried search engines for relieable resources but have found nothing that directly answers my question.

Thanks so far :smile:
 

AlteredEgo

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Barely Big said:
This made me laugh and realize how absurd the whole situation is. I am probably way overthinking this thing.

Yes, she knows that I am totally inexperienced. She has in passing told me of her sex life as either good or bad, but without any other details. She is (of my friends) the most willing to talk about sex and I know she is very concerned with sex safety.

What I want to know is: how far down to the body should a condom fit? Should it be flush (or almost flush) against the body or is it supposed to not cover the whole penis?

Clearly this is a question many on the board can answer, but again I am much more trusting of the advice of a long time friend than an anonymous name over the net. And before anyone asks, I've tried search engines for relieable resources but have found nothing that directly answers my question.

Thanks so far :smile:

Is that it? Ask her. You are a sweetiepie for being so worried!

I want you to know that it is taking way more self control than I thought I possessed not to answer your question. I'm seriously dying to give you an answer, and also worried that she doesn't know the answer. I know you don't want to get this info from a bunch of strangers, but where do you think she's going to get it from? You think she was born with the knowledge, or do you think she got it from an outside source (if she has it in the first place.) Just food for thought.
 

sares

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Barely Big said:
What I want to know is: how far down to the body should a condom fit? Should it be flush (or almost flush) against the body or is it supposed to not cover the whole penis?
well, actually, this is the thing. there are a couple options for how she'll respond, here.

EITHER

she'll realize you are trying to tell her you're hung, and be curious.

OR

she'll realize you are trying to tell her you're hung, and be disgusted.

...just don't get any ideas that you're being subtle. :tongue:
 

B_NineInchCock_160IQ

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Barely Big said:
We're both over 18 but under 20


otherwise known as 19?

Anyway, I don't think it would be unfair to her. It's probably going to be difficult for you to bring up the question, but you could start by asking her if it was okay if you asked her for some advice of a sexual nature. That would at least give her an out if she didn't feel comfortable talking about that with you. If you've been friends for so long and have previously dated I don't think it would be a big deal, and even if you do have some ulterior motives... so what? If you REALLY value the friendship and don't want to do anything to jeopardize it, then you probably wouldn't be struggling with this anyway. So clearly you still like her, might as well go for it. Trying to introduce this subject matter into your conversations seems like a pretty innocent way to go about doing that, too. It might work.

[edit] after reading your actual question... I'm not sure. You want her to think of you as a sexual being, but you're going to ask her something like this that clearly indicates your lack of experience? I also think Sares may be right. But if you ask in the right way it should be fine, though. Careful, as most men are notoriously bad at asking questions in the right way.
 

Wonderboy

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Hmm...seems like a ploy.

I can tell you now that, in an ideal world a condom should cover the entire penis and stop around the shaft. I don't think it does often...at least not for bigger guys. I've never had a condom go all the way down. Maybe in inch or so away but never all the way down.

Anyway, its obviously up to you, maybe you know what she's like. If she's the kinda girl that is into innuendo and would like to see just how hung you are. Or if she'd be disgusted by your blatant come-on.

If she fancies you, and you are pretty sure that that is the case I'd say go for it. I wouldn't do that but then again I'm not in the situation, its different for me...
 

Matthew

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In most cases, I think it's a great idea not to count on advice from the internet (here not least of all). But with this particular question, why would she have an expert answer compared to people here (or anywhere else for that matter)? It's not like it's super-technical or anything.
 

sares

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Matthew said:
But with this particular question, why would she have an expert answer compared to people here (or anywhere else for that matter)? It's not like it's super-technical or anything.
it's not about the question, it's about trying to catch the attention of his unrequited love. but that's not anything Barely Big doesn't know already; he told us in the first post.

see here:

Barely Big said:
I think that subconciously I kind of want her to think of me sexually, but am too ashamed to actually admit it to myself...
but you just did honey.

Barely Big said:
I know I'm still attracted to her some, and have a feeling she still is some towards me, but we both value our friendship way too much to take a chance with dating...
so what you mean is... she decided this, and you decided to live with it.

Barely Big said:
It really comes down to: Is it unfair to her to ask a sex related question if I have doubts of my motives?
unfair isn't exactly the right word, but yes, she may consider it a betrayal, since she has been confiding in you and treating you like a non-sexual friend, and it is a pick-up line, of sorts. because of the simplicity of the question, she will be able to determine that the answer is not its purpose.

it's a risk. maybe you really will pique her interest. but what you have here is not a friendship, not a "girlfriend/sister combo," you have unrequited love. there is no friendship to save. when one person falls in love, it isn't a friendship any more. See also cuddle bitch.

I wish you luck.
 

Barely Big

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In order of appearence,

BronxBombshell: very good point. Feel free to unload your answer. I have no reservations about seeing information on the net, I just have a hard time trusting people through mediums like the internet or even the phone. I don't know what it is, but I've always needed face time. Thanks for one perspective.

sares: I'll address all of your posts here. I do indeed love this person, but have no intention or desire to date, or sleep with them. I love her in the same way I love my best friend (a guy). The only difference being that I am straight and therefore more obviously recognize when she is looking good as opposed to my best buddy. I could understand where you get the idea that I want to do such things from what little I have said. A big reason I was afraid of asking her is that I was afraid of sending the wrong signal. Yeah, it sounds like a pick-up line in some way, but it is my actual question. Could you perhaps try giving a different phrasing for a similar question? Yes I am also afraid there is some latent attraction, but again I don't want to fool around with her, date her, marry her...anything like that. I truely value our friendship above all else. The break up in jr. high was indeed her decision, but it was jr. high for goodness sake. It wasn't serious and it was for the reason(s) mentioned before. Thank you for offering another perspective on the matter.

NineInchCock_160IQ: she's still 18, I'm 19. It's just the way it came out :biggrin1: She already knows that I have no sexual experience. I don't want this to sound like (or be) a come on at all, but she happens to be a fairly open person who is one of my closest friends. The reason I'm struggling is because I don't have anyone else in my life at this time who I feel is both sexually experienced and also (reasonably) open to conversation on the subject. My initial conclusion when the oppertunity presented itself was to let it go, and just keep on wondering and hope my first time is with someone more experienced than I. This isn't the kind of thing I want to talk to a parent about, so I figured an anonymous situation such as this board seemed like a fine way to get my thoughts critiqued without having to suffer the embarressment of such a conversation with a parent.

Wonderboy: Good to know.

Matthew: The same point as BronxBombshell, yet still a good one. It likely goes back to my somewhat unfounded distain for the net, phones, mail, etc.

To all: You can choose to believe me or not about our relationship, but really I don't care much what you kind folks think about it. I know we're friends and I don't want to be anything more. I may come off a bit brash or defensive and I apologize if I am sending the wrong vibe. I was concerned about asking this question because I thought it would send the wrong message and be an unfair spot to put her in. I do find this person attractive, but I have seemed to be able to get around that point thus far and plan on doing so as long as I know her. I am slightly suspicious of my own motives because she is a girl I find attractive and I am scared that I'm doing something really dumb like making our friendship uncomfortable.

I hope that clears up everything :smile:
 

JustAsking

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Barely,
Here are a few disconnected observations about your postings. I put them out because they might be helpful, but I don't think they add up to an explicit conclusion.

- You seem to be very articulate and intelligent. Its possible you could find a way to express your question so as to not jeapardize your relationship.

- You seem to have a talent for overcomplicating emotional things.

- There is something oddly contrived about your question, but I believe you are sincere in asking it. There is no way to say this without sounding harsh, but I don't mean it that way. And that is, you seem to be very much in love with your own gallantry. As if you relish the burgeoning sexuality of you and your friend and the drama involved in keeping it from affecting your relationship.

- Platonic relationships amongst young people used to be a very rare thing in my day. However, I think it is much more common now amongst young adults. I think it is a beautiful and valuable thing and you are right to want to shield it from your own sexuality. You will have many lovers in the future, but not many female close friends who you have known since early childhood.

Here is a suggestion. Open a new topic with your friend in your ongoing discussions about your respective lives. The topic is your separate sexualities in this new and wonderful time of life. On top of that topic should be the meta-topic of how for the first time, comparing notes on life could possibly introduce some sexual tension into the relationship even if its not something you both would want. Like all relationships, awkward topics should always be worked out through lots of discussion.

While doing this, practice examining your motives and when you find something you are not proud of, bring it up in the conversation. In doing so, you will be able to practice recognizing and curbing your motives, and also diffusing the tension it produces.

Does this help at all?
 

Barely Big

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I may as well resolve what I started, so here goes.

JustAsking: Thanks for the compliment for one. I tend to overcomplicate most things, emotional even more than others. It's something I've tried to work on in the past, but haven't made much headway on. I am not offended at all by your phrasing. In fact I think it's rather accurate. I am almost boastful about the nature of our relationship because I am so happy with where it stands. Your experience is a valuable asset to this conversation and I will take what you said to heart.

sexykimmy19: Any reason why, or just want to hear a good story?

I've decided to put the question by the wayside and not risk anything. I'm sure out friendship would be fine regardless, but if it means avoiding a week or so of awkward glances then I'm fine with it. Nothing lost, something gained. I got an outside perspective on (my perspective of) our relationship and where it stands. I'm happy and as far as I'm concerned that's the end goal of most things I do.
 

baseball99

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im not gay but if you want her to think of you sexually you should definitely ask her a bunch of questions about condoms. Make sure you have a bunch of questions in mind or you'll forget. Like start the conversation with "What are your thoughts on condoms? How do they feel for girls? What kind of lube makes it feel the best? then ask How far should the condom roll down? Have you ever had a guy break a condom or have it slide off?

if all else fails you should tell her you have some lower abdominal pain and show her your abs ;)
 

MXM107

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Barely Big said:
What I want to know is: how far down to the body should a condom fit? Should it be flush (or almost flush) against the body or is it supposed to not cover the whole penis?



Rather than asking her to tell you, ask her to show you.

then take it from there.
 

bakardi420

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Sounds to me like a confidence issue!

Like you said, you are a virgin. You're 19, and obviously feeling very sexual. You want a sexual relationship, but with no prior experience you lack the confidence to begin one.

You have an attractive female friend who you are very close to. Because of your raging horomones and need to connect, your brain is telling you that this might be your best shot. But your lack of confidence is also telling you "We're too good of friends to try that." Bullshit! There is never such a thing.

There are lots of females out there who think you are attractive. Your friend probably does too. But you have to be confident, see yourself as good as everyone else. What reason is there for your friend to see you differently than a friend? From being so close to you she know's your insecurities, knows how you might not be so confident sexually with woman.

But get over it! You're only 19! It may seem like everyone around you is scoring all the time, but you'd probably be surprised how many guys are also in your shoes too.

As for your question, I think it will not improve any chances with this female (if that is what you truly want). She knows that you don't have sexual experience and will probably just see the question as a way of dealing with your insecurity. If you ever want to be sexual with this girl, you are going to have to be sexually confident to some degree.

As for the condom, if you want to be properly protected you need to roll the condom down to the base of your cock. Don't they teach this in health class? In porn they never roll it down all they way to make the dicks look bigger.

Hope I helped somewhat. You have it in you, just be confident! Some things take time.