I have a stupid question so forgive me for asking it but.... There is this guy I work with that I just collided with the other day. Details in [ http://emptyclosets.com/forum/lgbt-later-life/148885-who-knew-he-gay.html ] I have not had sex with him. When that happens, he will be my first guy to have sex with. I will not be his first. It looks likely we will have sex this week. What are the things I should be aware of and know about ahead of time?
There really is one thing that is paramount in sex: communication. Quite often, you hear people saying things like "I wasn't sure if my partner liked this or that", or even "how was I to know what he wanted?". Well, the guy is right there, and sex is fun enough without adding a guessing game on top of it. So your best move is going to be talking about it. Before, during, after. Before you discuss what you want to do (and maybe even more importantly: what not!). During, you give pointers and clues as for what's working (and what isn't). Afterwards, you can continue what was awesome and what could make it more awesome in the future. And when I say talking, I obviously mean listening in equal measure. Secondly, there's timing. One of my teachers once told me this about speaking in public: "When you think you're speaking too slow... you're probably still speaking just a bit too fast". And that applies to sex too, really. Don't rush into things like you're trying to get to the end of a checklist. you're not on a clock to get off. If something works well, you can keep doing it for a while, and only move to another position or act when you both sent and received clues that it's what you both want. Finally: sex isn't about proving anything. It's not about "who was best at it". It's about having fun. And I feel quite qualified to tell you that hilarious fumbling can be a lot of fun. Way more than trying to impress each other with sexual athletics is. So don't feel like you have to do this or that or that it needs to be perfect. Focus on having a good time. Others might have other advice. But the above is really the best and most universal advice that springs to mind.
Filip hit all the main points. He'll also tell you how I end most of my sex guidance posts: "have fun, damnit". Don't forget that you're having sex because it's fun. Lex
Like I said, just don't let your superior at your job find out. Most employers deal severe punishments for their employees engaging in any kind of romantic or sexual relationship, even heterosexuals are not exempt from this. This is something I really think you should keep discrete. Like I said, I was fired from Staples for wearing one of those old "cause" bracelets which was rainbow and said "LGBT" on it and my boss said "We just don't need people like you around here." I shudder to think what would happen if I ever got close to any of my fellow employees, even a platonic (friendship, not romantic or sexual, or is that non-platonic?) relationship at any job is dangerous, so my advice would to just be to keep it on the down low or you could both be risking your jobs.
Wait - why are platonic relationships at any job dangerous? Lots of people befriend their fellow co-workers. Lex
Hmm, well you're from America, too-- you know how it is. I mean, every past job I've had where I've tried to befriend a coworker has ended with a serious warning or at the very least a slap on the wrist with a stern talking to. None of the bosses want to see the coworkers interacting in anything other than a fashion which they believe serves the customers. Heck, I'd get yelled at just for talking to another employee about anything (like what they're going to get for lunch-- little stuff) it was always just, 'block and face and speak not to one another lest ye forget thy duties.' Even if, heck, especially if business was slow or nonexistent. Seriously, that's how it is at every job.
This may be an issue of the industry you're working in. I work in corporate America and no one has ever cared if I've talked or socialized with my co-workers except when I was a call center rep on the phones. And then only if it meant calls weren't getting handled in a timely manner. Otherwise they didn't care. In my current job, and the last several before, I and my co-workers, including the boss routinely ger lunch or ice cream together and sometimes do dinner with our spouses/significant others. At my last job, we had parties at each others houses (and not the 'mandatory fun' corporate stuff, but actual fun with drinks and people playing instruments and having a great time. Even when I worked in retail (about the least fun job I've ever had), management wasn't so hardcore that they wouldn't permit talking as long as work got done. I don't think they cared what people did after work. Todd
Hopefully this is the kind of advice you are after. As you said he is experienced he should already know this but for your benefit: Make sure that whomever is bottoming is well prepared and has his passage clean. Use fingers or a small sex toy to begin to stretch the sphincter prior to intercourse. Work slowly and only introduce a new finger or larger toy when comfortable. Lube is your best friend, but a word of warning. If you are bottoming it will hurt at first. Stretching the sphincter will help reduce the pain but it won't eliminate it. As he's trying to enter push out as though you're taking a crap. This will help to further open the sphincter. Take it nice and slow and allow the bottom to dictate how far to go and when. It will start to feel good as you begin to relax so don't be disheartened if it takes a bit of time.
Okay, thanks to those who actually gave advice. I had sex with a guy for the first time yesterday. It was awesome beyond expectations. He is experience so he helped me discover what I needed to know. I am sure there is more for me to know, but given we will have sex again, he'll keep teaching me. But thanks for the advice given.