You're asking a few new questions that are not within my realm of expertise. I can't draw on PERSONAL experience to provide a response, but I can certainly give you general information based on what I've learned from other men.
It would be cool if some guys here would give you THEIR take on a few things, too. I provided a "lengthy post disclaimer" so as to avoid boring those who are uninterested, but that doesn't mean this is a private conversation!
So, OK... the butt plug... You don't need to reach in very far to touch the prostate. A finger-length ought to do it. Though I didn't pay attention to the dimensions of the butt plug, all but the smallest ones I have ever seen would be able to give the old prostate a good tap.
It's interesting to me because for years I avoided allowing anyone to touch my ass or give pleasure through prostate manipulation. I kind of think that for a while, when I was younger especially, this portion of sex was reserved ONLY for "bottom" guys. Also, it had always been MY job to play with someone else's prostate. Then I met a dude who just sort of did it to me, but he did it with the fore-knowledge that it was new to me, so he was gentle. I discovered a NEW sexual stimulation. And it dawned on me that there was NO good reason NOT to enjoy this if I so choose. I've always loved having OTHER parts of my body sexually stimulated (I like being touched anywhere), so why not this, too? It didn't feel shameful at all, it just felt good.
So I think it's cool that you are receptive to this and interested in it; yet I think you might want to browse the web for a few online diagrams of internal male anatomy so you are more familiar with the location of things!
Anyway... it's pretty unlikely that you are going to be able to stretch your sphincter by repeated at-home play with a butt plug or other toy. Your sphincter muscles are EXTREMELY resilient: they aren't going to get loose and easy to penetrate from toys. In fact, lots of anal sex isn't going to stretch you out that much, either. Granted, there ARE some bottom guys who can take a telephone pole up their ass like a champ after years of play -- but even then, the sphincter muscles still close tightly and usually don't ever get damaged.
What you CAN accomplish, however, is becoming used to the sensations involved. You'll learn how to relax your ass more, you'll have a good idea of at least what to expect, though I'm rather certain a real life dick is going to feel different from a smallish butt plug! You know... you're cooking up a stew and you taste a little gravy on the spoon. It seems good, but when you sit down to eat a plate of it you find it needs a little more salt than you thought.
As for how to communicate the fact that you need a man to go slow and easy with you... well, you just have to COMMUNICATE this! There's no secret code or finger salute or clubhouse door knock that will tell a guy this -- YOU have to do it. Bring it up in conversation prior to the fact. I'm going to imagine it would not only be unpleasant for you if an experienced top rams the hell out of you, but probably it won't be so great for the top if he finds that you aren't enjoying it or that your ass is clamping down involuntarily in an effort to stop him if it hurts.
What does a bottom guy want when it comes to YOUR dick in HIS ass? Again... you'd have to ask him. Individual tastes vary. There are dudes who want to be made love to slowly and passionately. There are dudes who want to be forced and aggressively fucked. And everything in between. You'll need a learning curve and a period of time to decide what YOU like best -- and then you'll need to find men who are receptive to that (or be willing yourself to try something new and see what you think of it).
Your safe sex questions are incredibly complex. I can't possibly type in an entire safe sex lecture again right now. There is a vast wealth of information here on the CFS boards, and a great archive post about oral sex safety. Learning about safer sex isn't necessarily something you do overnight. While it is certainly possible to say, read a book about it, study, and take a test the next day, this is information that you need to more or less just carry with you at all times. It's not like remembering the dates required for a history exam -- you can forget those after the test is over, at least until finals roll around.
Different sexual activities carry different levels of risk and the potential to infect you with different STDs. An extreme example of how hard it is to pinpoint EVERY possibility would go something like this:
Kissing is extremely LOW RISK for HIV. Almost, in fact, to the point of being NEARLY impossible. But it is NOT completely impossible. In VERY, VERY rare circumstances -- EXTREMELY rare circumstances, HIV can be passed via kissing IF AND ONLY IF MULTIPLE VARIABLE CONDITIONS EXIST. And then, IF AND ONLY IF all these conditions come together in just the wrong way to let it happen. In the real world, this is virtually a theoretical impossibility. Consequently, we tend to say that kissing is "safe." And it is. If HIV were spread through kissing and easily spread through oral activities... there'd be a LOT more of it around (not that there isn't enough already, but you get the idea).
Conversely, anal sex without a condom is EXTREMELY HIGH risk for HIV infection. Lots of variables still must come into play, but the physical act of unprotected anal sex makes these variables MORE likely to occur. Yet at the same time, not every act of unprotected anal sex with an infected partner results in infection of the other partner.
If you are standing in the middle of the highway on the Chicago Loop, it is highly likely that you'll get run over before rush hour is through. But if you are standing in the middle of the highway in Tonopah, Nevada, you might be able to lay down and take a short nap long before the next vehicle comes through.
The same basic situation exists, but the variables have changed. One situation is more dangerous than the other.
I have personally stopped in rural Nevada to urinate and did not see another vehicle for a good half hour after the fact. I've also been on the Chicago Loop and fought my way through a maze of traffic at midnight and also witnessed a vehicle on fire in the breakdown lane.
Something completely outrageous and unforeseen may have happened to me in Nevada while peeing by the side of the road. Maybe I stood too close to the nearest cholla cactus and a rattlesnake bit my balls. A variable I had not planned on. Practically impossible, for many reasons: rattlesnakes don't just attack, they aren't very active in the heat of the day in the middle of the desert, I would know enough to NOT stand near a conspicuous spot, it's almost impossible for a rattlesnake to reach my balls, etc.
We are placed into dangerous and potentially life threatening situations EVERY single day of our lives. We've used this analogy many times in safe sex discussions. A drunk driver might kill you in your car when you are going to the store to buy some ice cream. But probably not. Yet if YOU are driving drunk yourself, you might get killed without the intervention of anyone else: smashing into a concrete barrier will accomplish this very quickly. But you KNOW it isn't smart to drink and drive, so you don't do it. You've taken a step to protect yourself by doing the right thing. You still cannot discount ALL the variables and avoid OTHER drunk drivers, but you do your best. And for most of us, doing our best is enough to protect ourselves.
You need to adopt your own level of risk for sexual activities which makes you comfortable. We've used this statement many times here, too.
I can't write a list of everything you can get from every possible sexual act: that list is far too long and contains too many "ifs" to be of much practical use (more or less). You can get herpes from kissing, and that lasts for the rest of your life. But variables come into play: it won't happen every single time you kiss someone else who already has it. You can get the clap from sucking dick, but the dick you are sucking has to be infected with it first. You can get crabs (not a disease, but a parasitic annoyance) from doing practically nothing at all. You can get HIV from fucking, but even MORE variables come into play when it comes to HIV. Top or bottom, condom or no condom, rough or easy, viral load level of an infected partner, OTHER diseases an infected partner may have that makes him able to transmit HIV from blood more easily, OTHER STDs YOU may have which make it easier for you to accept a new virus, if a condom breaks or not, if you use the wrong lube which makes a condom more likely to break, the requirement that one partner IS, in fact, infected to begin with (obviously). On and on and on...
This is why I reject all purported "odds" for each individual sex act, as we recently discussed in another thread.
HOWEVER... this does NOT mean that we can't at least get an IDEA of what is more risky and what is less risky. In fact, such lists of sexual risk have existed for a long time and can be useful on an INDIVIDUAL BASIS so that we may come up with our own acceptable level of risk.
Science is an attempt to explain the world around us in a way in which we can understand more easily. Science often uses equations and formulas and a set of RULES which govern existence in order to do this. If we discover something which breaks a certain rule or law, we realize we need to modify that law, or re-examine another law, or re-evaluate our data. Sometimes science is cut and dry: this particular rule or law ALWAYS works -- we have NEVER seen it violated in the known Universe. Other times, rules and laws are more ambiguous, having multiple parameters which can be bent when necessary in order to accommodate that which baffles us still.
What you need to know from all of this babble is that calculations are subject to change. The best we can do is absorb as much information as possible and structure our actions along the path that allows for the safest journey.
You said you want to be set on the right path -- this you must choose for yourself, but always with the knowledge that what YOU do can affect others as well. So... let your sexual activities be pleasurable for you, as this is a wonderful part of being a human, but at the same time try to keep some altruistic advantage in the back of your mind, too.
Your fantasies: there's nothing wrong with them, of course. You seem to have a handle on all that. Like you said -- be willing to try more common things, but there is no reason why you should ever have to give up your fantasies. You just may enjoy them someday.
Finding a guy in general -- well, that's also up to you. This is something you learn by DOING. What works for me may not work for you. Places I go may not be comfortable to you. The more you do something, the easier it becomes most of the time. WHERE you go will also depend on the area you have to work with, as we discussed.
Picking up the signals -- that's another learned skill. Many guys will do more than just give a signal: they'll make SURE you know they are interested. But yes, some guys are shy. THEY want to be approached. They'll give a look or a gesture or play a little body language game and hope YOU are the one to respond. It can be very different each and every time, or it can be the same old thing over and over. WATCH what goes on around you. The more you OBSERVE, the more you'll learn. A bar environment is different from a bathhouse, but in both places men can use similar cruising techniques, too. In a bar, there's more likely to be discussion over drinks. In a bathhouse, it's pretty much sex after a fleeting glance. Yet neither is exclusive to the other.
Perhaps it is true that maybe there is a SLIGHT degree of higher risk that comes from anonymous bathhouse sex, but I've argued this before. Men who go to bars also sometimes go to the baths and vice versa. Men with STDs go to bars, men with STDs go to baths. YES, "whores" may frequent the tubs more often, PERHAPS. I guess it just depends. In a bar, you can more easily ASK a guy if he has an STD, but he can lie about it. Or he may not even KNOW he has something. Or he may genuinely believe he does NOT have anything, but he caught something two weeks ago since his last testing and has no clue. He tries to be honest, IS honest to the best of his knowledge, but... Oops. You can ask a guy in the baths, too -- but talking is often more restricted. Does it matter, given the possibilities discussed above? Probably not.
This is why it is up to YOU and you alone to protect YOURSELF no matter WHAT cruising venue you happen to be exploring. And this is also why you need to adopt your own acceptable level of risk and do your best to stick with it.
As for the whole "not being special" thing -- that shouldn't be taken too literally. What I meant was that I am not the pluperfect example of a gay god stereotype such as you might see in movies or images downloaded from UseNet. For men who are into a specific type, I may not be suitable for these guys. But I most certainly believe I AM quite special indeed.
Even my moniker here is a bit misleading. I'm not a "true" cub in a stereotypical sense, but it's probably the closest euphemism to describe me by APPEARANCE ONLY. I AM, however, usually scruffy most of the time!
It would be a lie to say that we do not first pick our potential sexual partners based on looks -- we do. But sometimes, if we develop a relationship, looks may be less important the more we get to know someone.
As I mentioned, sometimes we "allow" a guy to have some sort of sex with us but we aren't completely INTO him -- and probably more often than not, one partner is into another more than the other is into him. It happens.
I've met a few guys that at first I felt only "halfway" attracted to. But as I got to know them more, even if it was only for casual, no-strings sex, I began to LIKE them and respect them more than I thought I might. So maybe there's a dude that at first I didn't want to kiss... but then I realized that I'm seeing his INNER self come through a lot more than I did at first -- and the notion of kissing him becomes more appealing. So I do!
There will plenty of guys who are into "biker bear" types. Or whatever you want to consider yourself to be. And there will be a few who might want to give you a shot even if they wouldn't pick you as a "first choice." It's up to you to decide if you don't mind being a second choice -- provided you even KNOW you are a second choice! That guy who gives something new a try just might discover that he likes it and likes it A LOT.
Your piercings we have already discussed. These are a personal thing -- it's your choice to keep them, ditch them, or keep some and ditch others. You also have the choice of removing the more conspicuous ones for a night out on the town and replacing them later. Your call.
Sexual forums like CFS and many others have survived for so long because it is a subject that intrigues everyone. I've been doing this shit for years, man. The same questions come up over and over again, but there are always new ones, too. That's why I like it so much, and why I enjoy spending my time pounding the hell out of the keyboard. I LOVE SEX. I love talking about it, I love reading about it, I love finding out what OTHER guys feel about it.
Your questions and curiosity are MORE than healthy. You just need to keep in mind that sex is an extremely subjective topic. That's a rather obvious statement, you would think, but in all the years I've been doing this stuff, I've run into a lot of folks who think that there is always a definitive answer to their particular question. This is not true. FACTS are facts, of course, but sex is NOT static: it is highly fluid and changes each and every time. Everyone likes different things, but we also often find that there are majorities which exist, too. It doesn't matter if you are into something that most everyone likes or if you want something very, very different.
What matters is that you enjoy your sexuality. Sex shouldn't be cause for stress. Even when I bitch and whine about assholes I have met... I don't let it bother me for long. Sex is supposed to feel GOOD. It's supposed to be a way for two people to communicate on another level of intimacy that surpasses others.
Have fun with it. Enjoy the new experiences that await you. New things are only new ONCE. Don't let moments slip away if you can help it. Appreciate that which is good, let go of that which is not.
Play safely and have fun.
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