I'm a straight, bi-curious girl who is having issues opening up enough to even begin a sexual encounter with anyone, of either gender. Even though I enjoy masturbation, porn, etc., and feel pretty open about sex, I can't seem to get comfortable enough to even approach someone or recognize when I'm being approached. Most of the encounters I've had happened while I was drunk, mainly because I can loosen up enough. And yet, I can never let go enough to actually have sex, and am thus still a virgin. It feels like I may never be able to experiment the way I'd like to or even get myself into a relationship because I'm too self-conscious to try. I recently lost a lot of weight, and being hit on was a totally new experience for me. However, when I'm sober, it doesn't usually even occur to me that anyone would be interested in me. What can I do? This doesn't feel normal at all, and I'd really like to be able to experiment sexually, if only I knew where to start.
I think the key here is the statement that you recently lost a lot of weight, and found being hit on a new and (I am guessing) unsettling experience. You were used to being able to move through the world being sexually invisible. That is a kind of protection, even if it's also a hurtful form of devaluation and rejection. Us overweight people often dream of being thinner, imagining that will solve a lot of our problems. Unfortunately, our social skills don't get a chance to catch up with what's in the mirror if we do shed some pounds. I don't know of any weight-losing regimen that addresses the issue of sexuality. That's a pretty serious gap, because if you can't figure out how to fill that gap, over-eating begins to seem attractive once more. I would guess that this is a significant cause of relapse and weight gain.
Let's look at what your bottleneck seems to be. Where does the process of having a sexual experience get blocked? You say you have problems connecting sexually with others or figuring out when you are getting cruised. The few sexual experiences you have had took place after you got pretty drunk, and you didn't feel comfortable "going all the way" (as if any of us ever reaches that sort of point of sexual finality).
Gay men are the experts when it comes to cruising. If you have a gay male friend, make him go out with you one night and point out when people seem attracted to you. You'll probably be surprised by how many men are scoping you out. You've got that on your side—the testosterone-based nature of men's physical experience leads them to be, well, dogs. But how do you move from identifying the interested to a closer experience? It's often a matter of making eye contact. If someone is looking at you, and you're curious, look back and smile. Try to create some empty space around yourself. If he's brave, he'll walk up and ask if that empty seat is taken. Or he'll buy you a drink. If he's a little more shy, he'll blush and stare at his shoes. In which case, you need to go over there and ask him a question. Any question, no matter how inane, will do.
With women—well, you pretty much have to pick out one you think is pretty and throw her up against a wall. If she's single! I'm not sure I'm kidding. The single biggest problem in lesbian sex is the lack of initiation. Women who want each other like crazy can go for years having inane conversations about politics while their poor pussies scream at them, For Godess's sake! Make a move! If you aren't ready to get that physical, just ask a sexy question. Say, "What would you do if I told you I wanted to kiss you?" or "Can I put my arms around you?" These come-ons allow her to say something low-key like "I'm not ready for that yet" if she's not interested. But they also allow her to close her eyes and get swept up in the moment if she is!
Most people who go out are looking for somebody to meet, either for sex or love or both. And people are always interested in talking about themselves. Exploit those core facts of human nature for your own nefarious purposes.
Now, let's talk about the drinking. Figure out—ahead of time—how many drinks it takes for you to relax enough to enjoy yourself, but not so many that you no longer trust your own judgment. There's nothing wrong with getting yourself in a good mood. But do make and keep a promise to yourself that you won't exceed that quota. This will really maximize your chances of connecting with somebody who you actually like, instead of the most aggressive person in the room.
Put a little bottle of lube and some condoms in your bag before you go out. Never assume that somebody else will have these vital items. Once you've struck up a conversation, if you feel that there's some chemistry, let the other person know you are available. Then make sure you go from public to private. An invitation to go out for coffee or just someplace more quiet usually means the other person wants to have sex with you but needs to get their courage up. You can always say, "I think a cup of coffee would taste a lot better in your apartment" if you'd like to skip that phase.
Keep your sense of humor. Don't let rejection stop you. A person who turns you down knows themselves better than you do and is probably saving you from years of ugly fighting and ultimate heartbreak. Say, "Thanks for telling me you're an asshole," and move on.
I think this would be easier if you weren't a virgin. (Duh, Mr. Advice Man!) So let's pay some attention to that as well. There are a couple of different approaches to moving from that life phase to another. One approach says, "How you lose it doesn't matter—just get rid of the damn thing! After that, sex will be easy." The problem with this approach is that it isn't true. It often takes more than one attempt to figure out how to get off with a partner, even if you have a great attitude about bodies and pleasure. However, it does take the performance pressure off. That can be quite tempting when you look at the second approach, which says, "Losing your virginity is an experience that you'll always remember. It will shape your sexuality forever. Make sure it is the most memorable and excruciatingly fantastic time ever." Whew. Who can come home with that shopping list? A wedding couldn't be that good!
What if we set some minimum and maximum standards? You will not lower yourself to letting anybody with sex organs explore your body and come between the same sheets that you are in. If it's going to be a one-night stand, the person has to be somebody you like and respect—someone you won't cringe to recall. And they have to be willing to take safer-sex precautions. This is really important for your own self-esteem. If you tell yourself you aren't going to have sex with people who are disgusting or dangerous, you'll feel safer and relax and become more of a flirt. At the maximum end of the scale, you'd be going to bed with somebody you could love, somebody you want more than a million dollars.
There's a lot of room in between those two posts. Someone is waiting for you to make their night a memorable one. I hope it happens soon, and rocks your world with orgasms and tons of validation.