you lucky son of a bitch, take every mans dream chance and bonk the crap out of her!
on a serous not there might be problems due to the fact shes employed by your parents, but still go for it, sounds like a great chance!

This is the stuff of romance novels, porn flicks, and pipe dreams.

> Now recently she has offered to teach me how to have sex, so I don't completely embarrass myself my first time with a girl I am with.

Do you believe other boys who have yet to have their first sexual experience are so embarrassed that they fail to have a second and third? You and others are all too concerned about being "perfect" and not making any major mistakes. Every couple who has gone before you have these things in common--discovery, exploring and learning together, nervousness, foibles, and embarrassing moments. What a girl wants from you is knowledge more than experience, and then being kind, considerate, attentive, willing to explore and learn, and not be so up tight that you cannot enjoy yourself, each other, and have fun.

I'm surprised that in all the lurking you have done that you have not read the articles listed in the Index, especially this one:

HELP! S/He is more EXPERIENCED! To which I say:
The relevance of this article for you is to teach you that every time you have sex for the first time with a new person that it will be like "the first time" all over again. So, is your nanny going to be following you around for the next ten years or so?

> -after my 18 birthday (in a month) she will take me to her apartment and have sex with me a few times a week for a month ( she was thinking maybe 7-15 times) and advise me on performance, technique and help me build up endurance.

What are her qualifications? What is her education and experience?

What I think is that she is an opportunist and you are likely to be the victim. How do you know what she "teaches" will be correct, accurate, complete, and relevant? Will she teach you about birth control, yours, hers, ours? Will she teach you the importance steps of romance with regard to arousal? Will she teach you to take your time and devote no less than half an hour to making out and then how to kiss and caress in a variety of ways in order to fully arouse her as well as you? Will she teach you the gentle art of seduction? How many techniques for controlling your climax does she know about so you can keep from climaxing before you want to?

If you have read the articles listed in the Index at least once and hopefully more than once, you will have accumulated more knowledge and information than many young fellas. As for the practical knowledge, that changes each time you fool around and make out with a girl and have sex. In your lurking, I'd be surprised if you haven't read where I've stated more than once that making love is not what we do to each other, it is what we do with and for each other, together. Making love is not something we do by the numbers: Do, A, B, C, and Z will result.

My point is that being embarrassed is the least of a boy's problems. I recommend that you acquire the "working knowledge" required from the articles, first and foremost. Experience equates to knowledge, not skill.
What will work better for you long term is to gain self confidence based upon the knowledge you've gained, not the experience.

Assume that the Nanny is not a virgin, yet the first few people you are about to have sex with are, is she going to be able to give you practical tips on how best to deal with the hymen? Because she is not a virgin, what about your practical experience and thus your embarrassment about this? My guess is she will not be able to give you any practical experience, so, you will not be any better off than anybody else facing their first time.

> I am not sure if I should be totally stoked or creeped out. She is very attractive ( I have thought so since she started working) and to the best of my knowledge is completely sane. Basically what I am saying is that she isn't a pervert or anything like that. So I am asking should I take her up on it.

As nice as her offer is, as you have noted, there are other more important risks to be concerned about. My recommendation is to thank her and say "no thanks".

In your lurking about the site, did you read this thread?
Virgin, looking for 'first time' answers...

Here is what I want you to take from this discussion: Be honest with your partner as to your level of experience (although, do not tell her or discuss the specifics of your history with others) then explore and learn together in partnership. Know and understand that the first time or two you and someone have sex it may not go exactly as planned. There might be an embarrassing moment, however, this is not about you being inexperienced or inadequate, it is about the dynamics of the moment for which she may have contributed, also. So, begin your reading assignment, now.

I hope this is of help. Got questions?

Messing about with an employee is NEVER a good idea.

He's asking you this because why would a hot female of 20-something want you when by rights she should be out playing with men her own age and seeking a husband? There has to be a reason and most likely - it isn't good.

Whilst appearing to be a horny teen's dream (was there not a movie based on this premise?), it is fraught with dangers. Evil is spot on. Imagine a nanny pregnant with the little lord's child. Big payoff to disappear. If her schedule is such that she cannot get what she wants where she should be getting it, there are other problems and, with her own flat, this is not likely.

Not to mention sexual harassment lawsuits and issues with your parents.

Before our discussion progresses any further, I want to tell you that I am enjoying the dialog. You seem like a straight up young man who has his wits about him and truly looking for information and guidance. This is much more enjoyable than talking to a kid who wants what he wants when he wants it and will not accept an opinion different from his own. Kudos to you.

Yes, "friends with benefits" can and does work between a man and woman who both desire the arrangement. It also works best with people who are on the same page in life. "Page" is roughly defined as:
14: 13-15
16: 15-18
18: 17-20
21: 18-25
25: 22-30
30: 25-35
35: 30-40
40: 30-45
45: 35-50
60: 45-70

Granted, these are arbitrary ranges of age/maturity compatibility and not hard and fast, yet I list them to show you that the nanny is at a much different stage of life, maturity, and, interests than you. Better me thinks to socialize with people in your own age range.

For the sake of discussion, let's presume that her offer is on the up and up and genuine. As noted, she is an employee and regardless of the familiarity and closeness between you, there is an ethical line you do not cross, regardless of the job description. Other work related boundaries to observe are:
* do not date co-workers (if you do, make certain to work different shifts)
* do not date the boss

The mention of pregnancy was brought up, and this is a very real possibility. Even when using three forms of contraception, there have been many cases over the years in which Mother Nature did smite a couple in spite of their best efforts. You and every boy must understand that anytime your penis is exposed when in the close proximity of a girl, you are in fact playing a version of Russian Roulette. You must consider it to be a fully loaded cannon with a hair trigger! Any time it is aimed at or pointed toward a woman's vulva, she can become pregnant. Teens and women in their twenties are the most prone to becoming pregnant. One form of contraception is insufficient! Just a condom; just a pill; or, other highly reliable method is insufficient. It takes two, and many of us recommend three forms be used together: condom, pill or other, AND, spermicide. Both of you must be proactive by looking out for #1--each of you individually.

> Honestly I’m not 100% what you are asking with this question

I was asking the question to try and gain some idea of whether she is actually going to do any teaching, or, whether she was mostly going to say do this and then that and then critique you. Either way, I hope you are well into your reading assignment, here, by clicking on each of the articles in the Index. You can also go to the library or your local bookseller and get the book: "The Joy of Sex", for some great instructional and background information.

It wasn't too many years ago--probably when your grandparents were teenagers--that intercourse before marriage was very much frowned upon.** Oh sure, kids fooled around and made out {necking and petting) and had great foreplay but that usually was the extent of it. When the time did come for first time intercourse, what was pretty high up on the list was mutual discovery. I'm not against a couple exploring and gaining some experience before marriage; although, I still am a firm believer that first-time-ever intercourse is best saved for the second act of the marriage ceremony. Why? Because intercourse has more to do with a couple's emotional connection and melding of the psyches than the physical pleasure, not that this is not part of the experience. No matter how many other "firsts" a person has in their life, there is nothing as intense and emotionally rewarding as the very first time--and then, only after having declared: "I Do!".

If you want the most intense orgasms possible, then stick to foreplay activities. If you want the most intense emotional satisfaction possible, then have intercourse. There are valid arguments for both beliefs. All I ask is that you give due consideration for the belief that first time intercourse with a beloved having just declared your vows is very much worth the wait. This requires some faith that there is something greater to experience than purely getting your rocks off.

If you truly desire to be a world-class lover, my recommendation is to devote your time and effort into learning how to make love to a woman and this does not mean just how to finger and titillate her pieces-parts. Making love has much to do with learning to please and satisfy her emotional needs. Making love with a woman often begins hours or a day before actually getting your clothes off! Plant the "seeds of desire" and a hint of intent long beforehand. Make love to her mind FIRST, the rest will follow. Demonstrating your love for a woman means learning how they are different from you, physically and emotionally, and how best to arouse and excite these differences. Most young guys do not know until much later in life that women are "wired" much differently and that what works for them is not what works for their partner. Understanding these differences and how to work with them is the first step in becoming a world-class lover.

I've said more than once that a couple should explore and learn together; that making love is not what we do to each other, it is what we do with and for each other. If you read the article on "experience" and also the article that discusses the how-to of learning how to stimulate each others genitals that having had lots of practical experience beforehand is not necessarily going to be of any help with this particular person, now. Each of us is uniquely different in enough ways that what worked for someone else is not necessarily what will work with this new person; nor what will work for her later in the day or tomorrow. In addition to reading these two articles, please learn about the importance of communication and providing each other with verbal and non-verbal feedback.

If you are uncertain about what the female anatomy is like, Google the illustrations. Later, if you and a girlfriend (your own age) want to fool around and make out and explore each others body--fine; set the boundary at foreplay and not intercourse for the foreseeable future.

> And when we both aren’t dating anyone occasionally fool around a bit, and it hasn’t affected anything adversely. However (correct me if I am wrong) I would imagine that there is a bit of a difference between two teenagers making out vs actually having sex.

Not just with teenagers. Making out stops with or before foreplay. Sex=intercourse and as explained, above, there is a significant and profound difference between foreplay and intercourse.

When teens make out, the tendency is to throw caution to the wind while engaging in adult activities yet being unable or unwilling to foresee the consequences. Much of what teens do are not fully thought out because they are not yet able to "see around corners" and predict the consequences of their actions. The area of the brain that gives us this ability will not be fully developed until sometime during the the individual's 21st year.

> We still talk a lot and give each other advice on life/sex/relationships ect. And when we both aren’t dating anyone occasionally fool around a bit, and it hasn’t affected anything adversely.

Sounds like a win-win friendship. Keep on keeping on for as long as it is beneficial for the two of you.

Winding up this session:
** Most of what you want and need to learn about the physical aspects of making love can be discovered and honed with and during make out sessions and foreplay activities. Intercourse is not rocket science. Its actions are little more than placing P into V and stroking, then thrusting. The rest with regard to PA and PE should either of these become a challenge can be worked on one-on-one when the time comes. Don't sweat it. During your reading you will come across a discussion of why the Woman Superior/Cowgirl position is ideal for first time intercourse along with the knowledge that this places the woman in control of the action and activity more so than you. Now, ain't that just honky-dory?

I've had a lot to say the past several days about dating so I urge you to read those thoughts and recommendations.

Your turn....
-doc

All is good advice but not quite relevant to the social dangers being faced in screwing his former nanny who is still in the employ of his parents.

[QUOTE=Brandye;253553]All is good advice but not quite relevant to the social dangers being faced in screwing his former nanny who is still in the employ of his parents.[/QUOTE]

> For the sake of discussion, let's presume that her offer is on the up and up and genuine. As noted, she is an employee and regardless of the familiarity and closeness between you, there is an ethical line you do not cross, regardless of the job description. Other work related boundaries to observe are:

> > The mention of pregnancy was brought up, and this is a very real possibility. Even when using three forms of contraception, there have been many cases over the years in which Mother Nature did smite a couple in spite of their best efforts.

> > > Much of what teens do are not fully thought out because they are not yet able to "see around corners" and predict the consequences of their actions.

[quote=EvilEvilKitten] Not to mention sexual harassment lawsuits and issues with your parents.[/quote]

> > > > why would a hot female of 20-something want you when by rights she should be out playing with men her own age and seeking a husband? There has to be a reason and most likely - it isn't good.

> > > > > Messing about with an employee is NEVER a good idea.

[quote=]What I think is that she is an opportunist and you are likely to be the victim.

I recommend that you acquire the "working knowledge" required from the articles, first and foremost. Experience equates to knowledge, not skill.
What will work better for you long term is to gain self confidence based upon the knowledge you've gained, not the experience. [/quote]

Wordy or short and succinct, taking this young woman up on her offer is not a good thing to do.

Thought I'd tell you about how I lost my virginity:

When I turned 18 (and was still a virgin) I began exploring bdsm, a friend of mine who is a year older than me had already made some connection in my area's bdsm community and was able to get me into some exclusive parties. almost 2 years later I met a dominatrix 2 years older than me in a party (we had a nice session) and we later kept contact via the internet.

About a month later she invited me to her place (I still live with my parents, she was already living on her own).
I was afraid there was something sinister behind this but in the end I decided to go for it.

She was very patient, had plenty of condoms (she wouldn't let my thing go near her crotch without it) and taught me many things certain men won't learn on their own no matter how much sex they have.
We had a short relationship that really made my current one very fulfilling.

Bottom line is: If you're going to pass it up make sure you really don't want it because it could be a valueable experience.

[QUOTE=lovesfool;253485]you lucky son of a bitch, take every mans dream chance and bonk the crap out of her!
on a serous not there might be problems due to the fact shes employed by your parents, but still go for it, sounds like a great chance![/QUOTE]

Poor attitude. Bad advice.

> Bottom line is: If you're going to pass it up make sure you really don't want it because it could be a valueable experience.

This is not the issue. What is the matter is in gaining some experience and practice with his parents' employee and not as in your case, a dispassionate albeit experienced stranger.

There are many societies, existing and previous, in which sex is introduced by a mature, experienced member of the opposite sex. The "older woman" giving him experience is not the issue. The near family relationship is the reason for the warnings against.

I don't understand, why her being an employee of his parents should be his concern?

His relationship with her is personal and not an employer-employee relationship.
I do agree that if his parents become aware of this it might have bad results but since it's neither in his or her interest I doubt the parents will (especially if it's done in her place).

I guess it might seem weird to me because we come from different societies but I don't really see why this should be a problem.

[QUOTE=Grim;253585]
I guess it might seem weird to me because we come from different societies but I don't really see why this should be a problem.[/QUOTE]

Yep probably, but sometimes things are worth preserving as a fantasy...;)

Grim,

She was his nanny and is still in employ of his parents as nanny to a younger sibling. Think this through. What are her motivations for wanting to screw a 17 yo who was in her care for some few years? Teaching him how is the only nearly legitimate reason. The other possibilities are all questionable. What would be the result of a pregnancy for all concerned - him, her, parents. Doing any simple cost-benefit analysis you come up with risk that exceeds potential payoff.

That is free from any societal norms. Unless the father hired her as a trainer/consort for his son (yes, this happens).

With that attitude you can say there's a sinister motive behind everything.

While what you say is very reasonable and possibly true you can assume it about any girl.

There have been cases of women younger than the nanny extorting their male partners of the same age after sex with the threat of pressing false rape charges.

Any person, man or woman is a possible extortionist/rapist/murderer/thief, etc...

While I don't deny that what you said should be considered, I ask you:

How are you supposed to start a relationship with a stranger if you won't allow yourself to trust a person you've known for years and shares secrets with you?

If she were a stranger I would likely say "go for it!" It is the family relationship (not blood but employment and past near-parental role) that says it is high risk.

And I don't see why you, Grim, are having a hard time understanding why this is such a rotten deal.

Bottom line - she's been surrogate Mommy to this kid for several years. Now someone in that position has to have some screw loose if she's sexually propositioning her surrogate kid. CREEPY PSYCHO CHICK.

Now you may not have a problem "sticking your bits into Psycho" - but it is not recommended.

Just because you can does not mean you should.
Part of being an adult is knowing when to say "NO, thank you, but NO".
This is one of those times.

For her sake as much as for yours.

[QUOTE=thathornyguy;253648]
additional thoughts?[/QUOTE]

After what you said, only this:

[url=http://www.youtube.com/watch?v=aEC7FK0xVTQ]YouTube - The Penis vs The Brain

Good luck with whatever option you choose!

> Now she said that she is on BC and that I would be wearing a condom so pregnancy chance would be minimal I would imagine.

Reduced, although, certainly not "minimal". Did you read the part where I said some of us recommend three types of contraceptives be used together?

> like all teenage boys my dick is telling "I will murder you if you don't go for it!" And being a teenage boy I take my penis' consul very seriously.

From all you have written and put forth, it seems to me that you are still trying to justify doing this and ignoring your better judgment, being a right fighter than being safe and sane and ultimately happier than worrying. Rather than coming up with all sorts of justifications for, why not begin being learning to be an adult about possible outcomes and damage likely with your family dynamic. You also seem to be trying all you can to minimize what we've been recommending to you about boundaries, crossing certain lines, regardless of what is in her job description.

At eighteen, you have yet to reach your sexual peek, what are you going to do to handle several more decades of temptations that come your way, whether they involve your penis or not? It is time to be and act adult about adult activities. We understand about hormones and being driven by them. You are not experiencing anything different from any of the rest of us who have gone before you. Most of us did not have the luxury of a nanny and had to go out and actually begin dating. Why not try this and learn something even more valuable along this path toward sexual enlightenment?

With the added facts, including leaving this summer and attending a prestigious graduate program, this is looking too good to be true. Have we mature regulars been had, again?

Being accepted to a prestigious graduate program could mean that the person is a responsible, intelligent, and stable individual, or it could mean that they redirect energy used to deal with personal problems towards their studies and the issues build and build....

People have listed the very reasonable reasons why one shouldn't go through with this. While she might not appear to have played a surrogate mother, at the very least she played the role of an older sibling! I agree with the others who believe that this is not worth pursuing for the same reasons.

The only new thing I'd like to add is that you're about to go to college - do you really think there will be a shortage of females looking to have safe sex with no strings attached?

[QUOTE=funinthesun;253700]
The only new thing I'd like to add is that you're about to go to college - do you really think there will be a shortage of females looking to have safe sex with no strings attached?[/QUOTE]

That is such an obvious observation, I'm sitting here wondering why I didn't think of that, also.

I guess the o/p didn't think about this bit of logic, either, because he is too focused on immediate pleasure instead of long term gains.

this whole situation sounds pretty surreal.

do you feel like she's an older sibling to you? if so, then i'd definitely stay away. There are all the social issues that are very good points that everyone brought up, but I'll play devil's advocate just to get you thinking:

If you don't feel like she's an older sibling to you, you could just be friends with benefits. but, you'd have to talk to her about this, and tell her that you would just want a friend with benefits situation, not particularly a learning experience (she sounds like she's using that as an excuse).

However, it does seem like she has some other motives. Her motives may be as dark as wanting to blackmail, etc or it could be as innocent as she herself is just looking for some play with someone less experienced than her.

If you do pursuit it, sit down and talk to her about her motives and if she would still be interested if it wasn't for a learning experience. And be careful, obviously.