Deflowering a Virgin
 

I can't believe I am posting this, because I already am pretty certain what I am doing... But for amusement's sake... What would you do if you were in the same situation.

Let's say you are an older (but not old) stunningly gorgeous female (ok, so I am reaching a bit) and you have a male friend about 15 years younger than yourself. The friendship has lasted about 3 years, and started as a mentor-mentee relationship, and has turned into a friendship, though somewhat one-sided.

This friend has approached a mutual friend to broker a deal, he's trying to feel me out before he asks the question.

He's 24, nice guy, a little shy, but other than that he's a good guy, he's also a virgin, just never met the right girl. Well he's kinda sick of his virginity, and feels comfortable enough in what he believes to be a really strong friendship to ask for a favor (though he's too shy to ask me directly, yet).

So, if you were this stunningly gorgeous female and you were asked this favor, to be the "first" for this young man, would you?

No. Not only do I think it would make things extremely akward and possibly ruin a friendship, but he may very well regret things later when he meets someone who's right for him, as opposed to rushing into things.

Concur. Sex is as much about the person as the actual act. He would be doing himself a huge disservice to just "get it out of the way" as it were. Tell him to wait until he finds someone that will make it special and meaningful.

MAL!!!!! WWWAAASSSUUUPPPP GIRL!!

oh my goodness, I never thought I would meet another old forum friend on here! (you are the Mal from D2 OTF, right?)

If I were the guy, I would prefer my first time with an experienced and good looking woman (that being you, of course). That's because he is 24 already. If he were 15, then no.

I find 35 ~ 45 woman attractive. They have this glowing female quality that draws me like a moth to the flame. Burn me, I say BURN ME!!!

So if he requests it and you are ok with it. Bone away my friend.

i don't see the problem with just getting it out of the way. just because you don't lose your virginity to someone special doesn't mean it's going to be ruined when you do meet someone special.

maleficent, in a way you'd be doing him a big favor because i'm sure you have a lot you could teach him. however, if the friendship is truely as one-sided as you say, then perhaps he thinks you are someone special and is just using the "just to get it out of the way" line so you're more likely to say yes.

but as you said, you pretty much already know what your decision will be, so good luck or have fun... whatever the case may be. :)

I would say as long as it won't ruin your friendship then it would be OK. When you say one-sided that means he likes you more than you like him? In which case that's perfect because you won't be losing your best friend of 20 years or something IF something were to go horribly wrong after this.

I know this is probably bad to say, but if I were a single girl his age I wouldn't be looking for a guy who's a virgin. I wouldn't want a man-whore either, but a guy with some experience is kind of expected by 24.

He'd probably be more confident if he wasn't a virgin anymore and maybe that would help him finally meet that girl he's been, apparently, holding out for.

I found that getting rid of my virginity helped me get rid of a lot of tension I had due to it.

I agree. Virginity is a big thing until you lose it. Then you realize it was nothing.

I would go ahead and go for it. It is probably the best thing you can do to help his social life.
As redgirl said,

I believe my tongue lost its virginity first cause I couldn't wait to go down on her first.

I lost my virginity to a 20-something woman when I was 14, but that's not a story I wanna get into.

I must say though that speaking of virgins, I've never gotten the opportunity of deflowering a virgin girl---but then again, the odds of that ever happening are slim to none anyhow.

just be careful... I personally wouldn't do it.

But then, I think your first time should be with someone you love. Having sex just to 'get it out of the way' seems like he'd be using you.

See,Heres the thing.... He will want more!
and in his head sexual thoughts will now = you,and he will bypass all of the romantical stuff that Is suposed to make the first time.. special.
A friend of mine took anothers virginity(as adults) and the guy has been *waiting* for three years now for her to do it again.
He will come into his own,in my opinion,You should let him.

if just thinks you are the foxiest goddess ever and has the hots for you,and you two do have a solid friendship,you could just... suck it a little?.. perhaps..

The opinions are interesting, quite interesting, and some folks make a compelling arguement both for and against. As soon as friend 2 told me what friend 1 was thinkin. (I wouldn't mind being thought of as the foxiest goddess ever - that'd make this older broad's day) There's no way I ever could.

Aside from the romantic part of my brain that pops up occassionally, that the first time it should be special. The first time should also have a willing participant and be completely and totally into him. I'm not. He's a friend. Any passion on my part would have to be faked and that's just not right for someone's first time. (Even though I could be quite the convincing actress).

Keep discussing - it's interesting...

Three reasons to do it: 1. You want him and you both know it is a one time thing. 2. You want him and you both know it will last for some time. 3. You want another notch in your belt.

Otherwise, it is just a sympathy f*** and in the long run he could do without it. If you are not excited by him or the concept of the act, then pass.

Why not? Males dont have the same feelings towards losing their cherry as do females. But show him the right way to do it his first time and he'll be damn grateful...

Please define how the friendship is one-sided.
Only go for it if
1. You find him sexy and you will be able to get into it. I would never want to be with someone who didn't really find me attractive.
2. You discuss the expectations for your relationship after the dirty deed is done and the terms are agreeable to you both.
3. You can deal with his inexperience, i.e., premature ejaculation, nervousness, awkwardness, possible impotence, etc...

If you ever change your mind, it sounds like the kind of story I would like to know about. **grin**

actually there are quite a few that do. I am one of these people. I had opportunities to have sex lots of times, but i held out because i knew that one day there would be that person that i would want to just be with forever. Glad i found that person. Love is a very powerful persuader. I hope people dont think i am like some straightedge religious freak for that because i am not. I just think its something very special.

So my advice would be to pass but hey maybe he just wants to get laid and thats fine too.

If you're selfish, you'll jump him and teach him all the great techniques you know. He'll have a great time. You'll have a fine time. And you'll remember it fondly the rest of your life.

But he'll carry the memory with him into bed with the next girl, and with his future wife. If will cause him to try to please her the way you taught him to please you. She'll probably know.

So it would be better for him to seek out a wife, and preferably one that's virgin. They might have a great marriage that way.

Still, when I was young, I tried to move on a woman more than 10 years my senior, and asked her frankly to show me the ropes. She didn't though. And that was probably best in the long run. But a horny young man would enjoy anything.

Confuscious say:

Virginity like bubble.
One prick, all gone.


Um....yeah....uh....I am a 29 year old....um....virgin, yeah, a vigin....and....I was kinda thinkin you and I could, um...uhhhh.... well you know......


All kidding aside, this could be both a good and bad thing. I was seeing an older woman when I was 21 and in college. We both knew we didn't want anything serious. Both of us wanted to experience each other....she wanted to be the mentor, I wanted to be the "mentee" as you put it. She taught me a whole lot about how to please a woman. I also gained confidence when it comes to women. *no pun intended*

If he seems like he is on the verge of asking, why not confront him. Talk about the friendship and ask him how he feels about messing around a bit. Perhaps it will lead to a heated discussion, followed by a heated class on Sex 101.

I'd only do it if you want to.
If you want to have sex with him then do it.
But I wouldn't "deflower" him; he's a grown man!

and

...are not compatible. The first one is correct, the second one is only good for a tease.

He'll want more if you (the woman) does anything. If you don't intend to go all the way, don't start. If you don't intend to do him occasionally afterwards, don't start. Or expect to have to rein him in after you reach your limits, and know he will indeed hope you'll go farther some day, until he finds a woman of his own.

I lost my virginity last year (age of 17)

I personally don't see sex to be as sacred as many other people do, but I do feel it has some significance in that you fee lcomfortable whipping your genitalia around in front of someone, and, depending on the person, this is pretty significant (I do however know people that will whip it out for a 10 dollar bet)

So, on this, I'd say if you felt that the friendship would not be harmed, and that it WOUDL only be a one time thing, I don't see the harm in it.

One-sided friendship - He tells me all his troubles. I listen. I won't solve his troubles for him, but will ask questions and keep asking questions until he gets the answers he needs.

He'll call me to share when good things happen to him.

He'll use my life experience as a sounding board for pretty much anything that goes on. I listen.

He really doesn't have a clue as to what goes on inside my head - not that he'd want to - it's a frightening place. And it's not that he's selfish, he'll ask questions, but anytime someone asks me something about me, if I don't want to talk, (I rarely do) I'll misdirect the questions back to him, so he's back to talking about himself.

Even though he's doing the asking, there's an extremely ethical side of me that says in some way I'd be taking advantage of him. For first time sex, especially, I really think that the people should be into each other, but that's the prudish side of me talking.

As a guy I say that the last thing I'd want to do is die a virgin. If he's 24 he has already missed out on several good fucking years. I think when I'm old and my soldier is at ease, I would regret all of the sex I didn't have when I had the chance. Do you really want him to become a 40 year old virgin?

I suspect that's the female side of you, actually. :)

what better experience for him to have on his first time than someone who is a really good friend, about whom he cares? i dont mean care like love, but care like just person to person i care about ya kinda thing.

plus, you are attractive, you should be very flattered that he has waited 24 years and chose you to be his special first time. make it special for him and enjoy yourself. :)

Going for karma, sex is good, but usually first times are really awkward. You need to help him along at least a few times, but lay down ground rules beforehand in extremely simple language (no ...) because I know I would want to push my luck in the heat of the moment. Esepecially since men don't have enough blood for both brain and member.
Enjoy your bad selves.

Why does the first time have to be "special", and what does "special" mean exactly anyway?

Simply sharing an intimate experience with someone you trust seems special to me. Engagement rings or marriage vows don't have to be involved.

Lack of sexual experience is a severe problem for a lot of men. In my personal experience, there is a switch inside a man's brain that gets turned when he pricks the pink for the first time. In my case, it made me feel male, and more confident in social and sexual situations. This of course is not the same with all men.

The reason "special" is important - if important at all - when it comes to one's first time, is because sex is such a major part of a human being's life, and he/she is experiencing it for the first time. There is certain vulnerability to it, and hence it is ideal that that experience is shared with someone with whom there is a sense of trust, safety and comfort. A mutual loving relationship typically provides that sort of emotional surrounding, but I would not say that a close friendship is far behind.

There's really no reason why his first time should be with someone he is romantically involved with.

No. Sex is a union of two people when they are in love or feel very, very strongly for each other. Sex should not be seen as a favour, as it can lead to a child or STDs...

not in my case.... which I think is a reason why I became more attractive for the prospect.... :|

I'd recommend against it. I'm in a similar situation as he is (minus the incredibly attractive one-sided older friend), and I think it would be something he may regret. It's not really something I'd want to "get out of the way," and as sick as he may be about it I suspect he's the same way.

A big part of it is that losing it isn't something I would later want to regret. I don't care if it makes me feel like more of a man afterward, or does any number of other things. Like every action in my life, I would want losing my virginity to be something I do no later regret.

So I vote against it.

Best answer is probably to ask him. Give him the choice: communicate, dammit. :)

I think that as time passes, it will become more of a burden to him, and the lack of confidence or knowledge will become a vicious cycle that only leads to more and more failures. I think as time passesm he'll have a harder time finding someone who he can honestly go to (that he'll have a connection with) and ask her to show him the ropes. he may just end up having a string of bad sexual encounters because he cant find someone willing to work with him. a couple of years ago, I met a girl who I thought was a grade-A chick. I asked her out (mind you, I'd been hinting at this for about 4 months). she turned me down, so I pretty much ended up looking for whatever I could find...never did find any other girl that was worthwile. the grade-A girl and I became progressively better friends, and one summer before I dropped her off, she told me to stop down the street from her house, and she started tickling me and the classic moment arose to kiss....but I didnt, I just backed away. There were too many questions in my mind about it, simply because i had never done it before. (no sh_t, I was 17 and never kissed a girl)
anyway, one day she was talking about how great of a "package" I was, I had the smarts, the looks, the money, the humor but she still wouldnt date me. she said she only had "flings" I told her fine, lets have a fling. she taught me many valuable things, and she has done an immense service for me. turs out that she liked me and we're still dating...

Thats a really long winded story to say this: if he's not ugly, and there's nothing overtly wrong with him that would make you disgusted at having a few learning sessions with him, I think you will be doing his social life an immense favor. Its all a mental block and I think you are in the perfect situation to remove it for him. my girlfriend got me started with what she knew, and we both learned together from there. I feel much more confident around...well everyone I suppose and im still a virgin.

I'd say to help him out if you think he's a good guy.

I say don't do it virgins are crazy.

I wish there were more women to mentor men on the in's and out's of sex. :-) (sorry, it just came to me, ha!)

It takes years to build up the experience to know how to satisfy a woman in bed, and you could be the Cliff's Notes to catch him up on what has passed him by.

I also believe being a virgin can really hold back self-confidence. Maybe that's my preconceived notion of older virgins, but I think the prospect of sex (real or perceived) drives us all in some manner or another. Subconsciously, people notice good looking people because they are wired to breed with fit partners ... survival of the fittest and all. It's a fact of living as humans.

But maybe I just have a high degree of interest in all things sexual ... subtle or obvious ... thus my TFProject account. :-)

Throw the dude a bone!! Or let him throw you one, whatever..

You could help prevent this guy from dying an old and lonely man. Add some positive karma points to your tab with the universe.

EDIT: Keep us updated on what happens;)

I do agree that guys do not see it the same way as girls- and learning the nescessary skills is quite important- and I do not think that there is any way that I could feel taken advantage of if I was a 24 year old virgin granted sex by an attractive woman- for most of us guys that would be more like winning the lottery than waking up and finding our appartment had been robbed.....