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Being a prude and hooking up T 13/11/28(Thu)17:18 No. 98539

File 138565550363.png - (399.58KB , 422x660 , 4.png )

Hey guys I need some advice. Like the title suggests I'm a prude. I don't feel very comfortable with strangers so I'm very picky about having sex. That being said, as I write this I have just realized that it's been almost 4 years since my first and last sexual interaction with someone. Needless to say, I extremely horny.

Now I have 2 guys lined up to hook up with. One that I find really attractive, and who I found on a sexual themed site (let's call him hot guy), and then another that I've known for a long time who always dropped hints about us having sex (let's call him good guy). Both of these raise slightly different concerns. Get ready for a ton of text.

My first concert is the initiation. Now like I said with the good guy, he has dropped hints several times, but neither one of us has ever explicitly talked about hooking up. I was just thinking of "seducing" him. Getting into his pants is not really a worry of mine. However the hot guy is a stranger. He asked what I was into; for which I replied "sucking dick and getting fucked", which was to the point, but then after a few messages he asked when I was free to "hang out" which kind of threw me off. Reason I say that is because my first time started off with a lot (and I mean a lot) of innuendo, which made things really awkward when it came time to get it on. He wasn't very forward which made me think "oh shit what if actually just wanted to hang out?", which made me inhibited. Since I never truly hooked up my question is, should I be extremely clear with hot guys and ask if we're going to just do it, or if he wants to actually hang out first? Is that something guys do in planned hook ups, do they hang before fucking? I just don't want to spend however long it takes to get to his place to "watch a movie" and then end up actually just watching a movie. You know what I mean? Like I said I never done this so I'm kind of out of the loop on what to do and/or expect.

Second concern is with cleanliness. I'm going to be bottoming for both guys, and although I know how to get clean (use enema that they sell at drug stores, or buy a reusable at a sex shop, etc...) I'm not sure when to do it. Now me, if I was a top having someone come over , I understand that they may have a life and didn't come set and ready to get it on, so I would expect them to take their time in the bathroom if need be. My experience however has taught me that not everyone is as "understanding". Now if hot guys just wants to get it on, then this won't really be a concern since I'll just get ready right before leaving to meet up. But if he wants to hang out before then it may be a problem. Good guy also might not be a "from my house to his house" trip. I actually might be out and about before meeting up with him and going to his place. Since the enemas are pretty conspicuous, I'm sure I'll become inhibited if he notices, specially if he ends up not being up to having sex with me. Am I over thinking this? Should I be blunt and just go in the bathroom with my bag, and just be like "whatever, I do wanna have sex"? (I have a small hand bag I put my stuff into; I don't like driving with both my front and back pockets full of stuff. My flamboyance grows as I get older, or I just ran out of fucks to give about certain things) Or is there a less conspicuous bottle that I can buy somewhere? Can anyone give me some info or share some of experiences, being either a top or bottom , having them come over or going to meet them.

ps. it's me in the picture. I'm doable right? I shouldn't be self conscious right?

13/11/28(Thu)18:10 No. 98540

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You are really overthinking this. Want my advice?

Stop building a fucking court case and just have sex.

13/12/04(Wed)11:08 No. 98562

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You sound a lot like me, actually. But we differ in the fact that my inhibition to hooking up is much stronger (not that that's bad!!).

Anyway, from what I hear from guys that hook up, you can be blunt. For the bottoming thing, I think it's okay to tell them "btw let me get ready plz". The "hanging out" part, I think could go either way. But if you're sure he wants to have sex with you, I think you could just ask him. Especially if you know he's hooked up before.

Hope it goes well! You have a nice bod, so if you feel like taking pictures, feel free to share them here hehehe.

Pic unrelated.

Matchbox Prince 13/12/14(Sat)08:38 No. 98593

1. You're planning on bottoming and have absolutely zero experience on merely cleaning yourself out? This whole thing is very unlikely to go well. First of all, you don't need a freaking kit from a drugstore to wash your ass out, unless you're made of money and like to waste it. Go to a pet store and find a plastic syringe, the type used for force-feeding small animals. They have ones with an attachable rubber tip, and get one with a capacity around 20-30cc if you can. Use plain tap water, slightly warm, to rinse out yourself after a normal bowel movement. The best part is, the thing is small enough to fit in your pocket, and can be explained away if asked about. After you do so, depending on your normal frequency, you'll have several hours of being clean. I can do something like that at 9:00pm and be fine until 2:00am. If you haven't practiced with a dildo, get one and practice a lot before you even consider trying a real dick, unless you're a glutton for pain.

2. You have an awesome cock, so why not use it? Either top, or just frot and suck each other off or something. Whatever you find is fun to do. Sex doesn't always have to involve penetration.

I don't really care which guy you go with; my preference in your situation is moot. It's your life — do what you want. However, a bit of advice: If either one of them are "top only", they're 99.99% likely to be a capital-A, Asshole who will use you and not care about you. If someone's that selfish about the kind of sex they have, they're going to be selfish about everything else; trust me.

Getting fucked tomorrow, some tips firsttimer 14/06/30(Mon)06:40 No. 99045

I'm getting fucked tomorrow for the first time by an old bear dude i met in a chat. I'm pretty nervous and a part of me wants to back out but i've been wanting to get pounded since so long that i'll do it (hopefully)

Is it normal that i'm so nervous? what should i do to calm down? and before the pounding what should i do? help this newfag /fag/ :(

(pic semi-related as the oldman dick is almost the same size)

viscosity 14/07/10(Thu)02:33 No. 99081

As far as the "hanging out" thing is concerned, if the site that you found him on is really a sex specific site (and not something more tame like Grindr or OKCupid) then hanging out prooobably means hooking up with the slight chance of talking a bit before hand.
As far as >>98593 is concerned, it doesn't matter how big your dick is, if you want to bottom, do it. I can agree that a lot of total tops (especially the ones on sex sites) can be pretty selfish but some people are into that. Just keep a heads up. And in my experience, you don't always need to take cleaning yourself out as seriously as you think. If you have a bowel movement then take a shower that's normally good enough for me. But if you're concerned about this going right, which you clearly and understandably are, enema as close to the encounter as you can and as long as it's not a couple hours later you should be fine. Use your own judgement. Know your anus.

viscosity 14/07/10(Thu)02:40 No. 99082

First of all, it's totally okay to back out of something if you don't want to do it. You don't owe this guy anything really and if it really seems like a bad idea to you, then don't.
Other than that, calming yourself down is something you probably know more about than me, seeing as how I don't know you. But if you're still nervous when you meet the guy, just tell him. If he's been around the block (which he should have been considering his age), he'll be understanding. Everybody's been there, and he's probably been with other younger guys the same way or felt that way himself when he was just starting to hook up.
As far as physical preparation, try to poop and shower before you meet up with him. If you have a dildo, try using it. The anus is a muscle and stretching it before the hook up will make his dick go in easier. And also, just tell him it's been a while. Again, if he knows what he's doing, he'll know to go slow at first and ease you into it before actually pounding.

T 14/07/22(Tue)16:49 No. 99109

OP here. I actually forgot I made this post but then saw it the other day when I was going to ask a suggestion on something. Here's what happened,I figured like >>98540 said I was just over thinking too much (which seems like is a thing I do in general) so I went to meet the "good guy". I couldn't do it though. I just don't find him attractive enough. I drove all the way there and then we just watched a movie and I left. It was so dumb. I don't know I just can't do it. Every time I'm horny I think of calling him and trying again, but then I jerk off and I'm over it.
Like I got myself a dildo after that (which is a bit too big but that's another story)and I ride it and I'm hard when I do it, and it's great so I want to do that with someone. However it seems I much rather ride my dildo than someone I don't have a strong attraction/connection with.
People I know are having sex on their first dates, meanwhile I don't even feel comfortable making out till the second date. Part of me thinks I shouldn't care and just be me, but then the other part thinks the me I am now is messed up somehow.(shit that rhymed) *sigh* There I go ever thinking things again I guess.

overthinking garuda 14/08/08(Fri)02:41 No. 99166

>>99109 Sounds to me like there's a disconnect between the head and the heart. If I can be so bold, you seem as if you want to have sex with someone you think physically beautiful and internally beautiful. Hang out with the hot guy, be clear that you want to get to know him a little before sex, think of it as a friend with benefits.

15/11/20(Fri)03:19 No. 99952

With sex, just always do what you like. That's the most important thing. In life as well.

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