Consider why you've been holding off in the first place. Is it because you've been busy launching a new business or finishing your dissertation? If you've simply been concentrating on other aspects of your life, you may want to jump-start your return to dating with a (safe) fling. On the other hand, if the reason you've been staying out of the action is because you equate sex with a relationship, a down-and-dirty affair is unlikely to satisfy you. Stop torturing yourself with an arbitrary timeline and work on the dating thing. And don't worry about your inevitable return to the land of the sexual -- it's just like riding a bicycle.
You've been dating for a few months when something starts to feel itchy. Is now the right time to talk about STDs?
This question is always a tough one -- you don't want to bring it up while you're still making out on the couch, but if you wait until he's reaching for the condom, can you even expect honesty from a man with an erection? Wait until the pants are coming off and then say, "I just got tested for STDs and I'm a clean teen [this had better be true, BTW] -- how about you?" Volunteering the information makes it clear you don't consider him just a dirty man ho. But no matter what the moment is or the response you get, you are always taking a risk. People lie about having been tested and they lie about having diseases. Use condoms until you are in a relationship, and get tested regularly.
You have an STD. How and when do you 'fess up to your bed buddy?
This is definitely a question of when, not whether -- you must tell your prospective sexual partners if you have a communicable disease. Never risk another person's health because "it's so unlikely that I'll pass it on." Tell your date in a neutral setting that's not sexually charged (i.e., don't wait until you are grappling on his kitchen floor). Calmly relay the facts of your disease -- how it is transmitted and how likely it is that you will pass it on during safe sex. Then give him time to think things over, and be prepared that he might bail. Just know that, no matter what you have, you're in good company. There are plenty of dating sites and support groups for people with STDs if you want to find a partner who knows exactly what you are going through.
You get caught with your pants down -- literally.
If you are having sex in a shared space, well, pull up your pants and apologize. If kids are involved, you might have to give the old "when two adults love each other very much . . ." speech, which is no fun for anyone. Or if they are young enough, do what my friends do and tell then you were wrestling. Though then, of course, there's the danger that they'll want to join in! If you've been caught by someone over drinking age, just promise to be more respectful in the future and change the subject. Chances are he or she is as embarrassed as you are.
Now, if the Peeping Tom or Thomasina entered your home or bedroom without permission, you shouldn't be the one apologizing. Have a discussion with your children about respecting privacy, and tell roommates and friends not to come a-knockin' when the futon is a-rockin'. In the case of your parents, seeing their kid in flagrante was probably punishment enough.
Your mate has erectile dysfunction.