I mean this in the nicest way. Be prepared for a big letdown. You've put sex on way too high a pedistal. It'll be awkward and crappy, and later on in life you'll wonder why you held out for arbitrary reasons.

Just take care, be safe, and have fun. Don't be caught up in who was before whom. :)

Welcome to the SI101 Board and its Forums. I hope you will enjoy participating. Please begin by familiarizing yourself with the Index found at the top of the main page. It contains links to helpful informative insightful, as well as how-to articles that discuss the most common questions and concerns people ask about. In addition, if you click on the site's Home Page you will find even more information. I recommend that you read every one of the articles and add the information to what you already know. Knowledge is empowering.

I agree with Firmus, you need a bit more insight into all of this. In this regard, please do a site search for discussions on this as it has been the topic of discussion recently.

> I have had many times to lose it in the past, currently I have passed it up with over a dozen girls, some more than once, but none of them i felt like having sex with.

I understand and concur completely; however, several knowledgeable contributors also recommend just getting it over with with the assistance of someone you do like.

> i told myself that i would not lose my virginity to someone who has had sex with someone that i know aka a best friend or a family member or something of the matter.

This is a valid concern; however, if a sufficient period of time has elapsed with one or more of these past individuals, then there should be no harm and no foul. If your trust issue happens to be one of the particular girl having a loose tongue and blabbing about what the two of you just did then you have a valid concern, as far as I'm concerned; otherwise--no.

Please read the article on the matter of trust.

> I didn't trust any of them close enough to take my virginity so that is why i'm still a virgin. Is this bad?

Not necessarily. In my never to be so humble opinion it depends on why you do not trust these women. That said, what is/are the reason(s)? Your answer will provide insight into helping you get beyond this.

> she is the first one that I feel comfortable saying the "L" word to in the open

How long do I wait to tell someone I LOVE YOU?

> one day I found out that she had sex with one of my ex best friends!!!! So it completly threw me in a loop as I have no idea what to do now.

As Dr. Phil often offers as a retort: "the past is over, the present is now, and the future has not happened yet." What are you going to do, date only virgins, and how are you going to determine this? We only have a person's word on the truth and validity of her "status". In western cultures we take the word of a woman. In some Middle Eastern cultures women are physically examined by a senior family member or community elder.

It is important to know that many people you (will) date have had sex with someone prior to meeting you. The older you become the more likely the probability. If a person is divorced, widowed, separated, and you step into this person's life, what now? Are you going to eliminate this person as a possible love interest?

Please understand that relationships are formed by two people, each with a past who choose to come together in order to create a future that is greater that the sum of its two parts. Relationships are partnerships. Making love is not what we do to each other; rather, what we do with and for each other. Making love to a person we love is the outward expression of that love. So while fooling around and making out, foreplay, and intercourse can and often are means to an end (our orgasmic pleasure), more often than not, the activity is so much more.

> So if there is anyone out there that can help me it will be appreciative. Thank you.

Begin as suggested: read all of the articles and add the information to what you already know. Pay particular attention to those that concern dating. The charter of this venue is to "pay it forward" by passing along information and skills to make life easier for those coming up thru the ranks. You are in good company.

I can see why it'd be awkward if she had past relationships with people close to you in your life. But since this person she slept with is now an EX-best-freind, then it's all in the past. Presumably neither of you will have to socialise with him again, or at least not much.

I say go for it, it doesn't make that much difference who her exes were if it doesn't affect your other CURRENT relationships. She is with YOU in the present moment.

----

That said Firmus is right, it will be awkward and weird and (if you are a guy) you will probably have trouble keeping it up and/or come too fast. This is totally normal.

Actually, I take that as a good reason to wait for someone you trust. You need to be sure they aren't just in it for kicks, and will accept the crap sex with you and not judge you on your performance when you're most vunerable. And most importantly.. someone who will give you a chance to try again, and again, and again ;) and work on achieving great sex with you over time.

We have a New To Sex forum area below that you should look at, by the way :)

You have made the mistake of thinking sex = love. Love is an emotional bond. sex is the physical expression of desire. Clearly, they are not the same. You will also find that the 'trust' you speak of is little more than your own insecurity -- you fear being 'hurt'. ALL of that is a direct result of your thinking sex= love; confusing the physical with the emotional.

It doesn't really matter with whom she has previously enjoyed sex as long as they practiced safe sex. In fact, you should happily go with a more experienced woman since you have got a lot to learn.

> LL69: One day I found out that she had sex with one of my ex best friends!!!! So it completely threw me in a loop as I have no idea what to do now.

> EEK: It doesn't really matter with whom she has previously enjoyed sex as long as they practiced safe sex.

> Doc: "the past is over, the present is now, and the future has not happened yet."
What must matter to the two of you is each other--dismiss the "ghosts" and concentrate on her and this relationship.

HELP! S/He is more EXPERIENCED! To which I say:

Next: If you are new & have no experience (Pt. 2 of HELP! S/He is more EXPERIENCED!:
If you are a guy who happens to be shy or uncertain about making the first move, know that this is OK. My suggestion is:
(Part 2 of Chapter 5)

> EEK: ...you have got a lot to learn.

You have an Action Plan, above, from which to begin. Please know and understand that first time intercourse, virgin or not, is likely to be more pleasurable for you than for her, although no less enjoyable. This is because the two of you have some fine-tuning to do in order to be comfortable with each other and to know what each other wants and what pleasures each desires. There are some "mechanical" matters to work out and this simply takes time and communication. So, while your initial connections with each other can be pleasurable, it is unrealistic to presume, that all will go as you hope for. If it does not, do not get upset--explore and learn together.