Dating advice

[Robyntboy]

Hi.
Ive just arranged my first 'proper' gay date. I know the guy wants to do a lot of things, im kinda nervous, hes older than me because I like that and hes more experienced ( im a newbie ) and I like that he knows what hes doing and what he wants. What advice can anyone give for a first date that im pretty sure will end up in bed? How should I prepare? Im a bottom boy btw.

 

[Theeym]

Start simple.
Do you want it to end up in the bed?
Is the date just for a hookup and are you okay with that?

If yes then, stay away from greasy food, clean yourself out well (douche),
Think about what your limits are and what you want from this. If he suggests something you are not sure about, don't let him pressure you into it. Do stuff YOU want to do with him.

Also, as a top, what I always recommend is a good shower, and edge yourself a little before the hookup. If you feel ready for the fun then you are usually less nervous!

 

[Robyntboy]

Thanks, that makes a lot of sense.
I would like more than a hookup, he says that if we get along we can go to his hotel room so I think itll be more than a drink.
Should I tell him any limits before? Or find out what he would like first?
I do want to be a bottom boy and I know he is a top man but im scared to bring up sex on a first meet in case he thinks im a bit of a slut!!

 

[Theeym]

So he has mentioned that this could lead to a fuck in his hotel room.
That's a good indication of where he wants it to lead too.
I wouldn't bring up your limits and what's off the table right away. See where this leads first, If he wants to get to know you before all that then that's great.
Of course, if he begins talking about sex, mention what "you" enjoy or want to try. If he brings up something that makes you uncomfortable then state that plainly. You're here for fun too after all.

Just asking but is this your first time bottoming? Might be good to mention that in case it does lead to sex and he ploughs you like a field.

 

[Robyntboy]

Yes itll be my first time. I have had toys in me before.
He has asid he will have lube and condoms with him but he said 'we havent got to use them' which I dont know could mean no sex or could mean sex without lube or condom!
Hes a very sexy man and he says if we get on then we could meet regularly so I do want to do things to make him happy. Hes even asked if id be willing to stay the night. I want to say yes. But im not sure if that means he would feel pressure to have sex with me.

 

[Theeym]

Well, hopefully it won't hurt you

That sounds like he may be up for blow jobs/hand jobs. Or body appreciation then so that's a good sign something can still happen.
But if you are not up for it then it won't be the end of the night.

If he is offering you to stay the night and you're happy for the company at least, there won't be any pressure to have sex with him.

In my opinion, this probably will lead to sex so hope your not waiting too long for the date

 

[Robyntboy]

only got to wait until next week. Im trying to think what I should wear.
he says he is quite dominant and wants to touch me while we are eating so maybe i should wear shorts?

 

[Theeym]

Ahh plenty of time to prepare the the date!

A nice tight top and lose fitting shorts would work but it depends on where your having your date!
If its a luxury place, I would go for skinny jeans if you have them to show off your assets and a nice shirt

 

[Robyntboy]

It isnt a luxury place, its just a sort of pub restaurant, then he wants to go for a walk after.
So I will wear shorts with a tight top and nice underwear too!
Hes asked me if id be willing to do kink things, im not sure what to say, I dont mind some things, but theres other things i dont want to do, il probably ask him what things he wants. He keeps saying my picture makes him horny so it looks like he definitely wants more than just a chat! Im horny about not being a virgin any more!

 

[Theeym]

That's a great idea!
Fuck you really lucky hehe
Well, he is lucky to have a chance at a fine piece of arse like you

When it comes to kinks, it really depends on what he wants. Hopefully its something tame like a little bdsm or such

 

[Robyntboy]

bdsm always sounds fun!
if it doesnt happen for any reason, il let you know since you say hes lucky. lol
its nice to be called a fine peice of arse!
Il ask him about what sort of kinks he likes, maybe he wants to spank me!

That's a great idea!
Fuck you really lucky hehe
Well, he is lucky to have a chance at a fine piece of arse like you

When it comes to kinks, it really depends on what he wants. Hopefully its something tame like a little bdsm or such

 

[Theeym]

It might be because I'm super fucking horny but, your arse deserves a good spank at the least, and a little hole play also!

Yeah, he is lucky and please let us know! I want all the sexy details XD
You most definitely have an arse that craves a good fucking

 

[Robyntboy]

Ive wanted a good fucking for a long time, but this is the first man thats ever really shown an interest. other guys always just talked about it.
I would love to get a spank and some playing with and him taking charge. I cant wait to feel a real cock up inside me.

 

[Theeym]

Ahh fuck, it's a shame you haven't had anyone follow through and give you the attention you crave.
If I had the opportunity I don't think I could pass it up

Hopefully, its everything you dream of

The first thing I remember noticing when getting fucked for the first time was the warmth of the dick touching my thighs and arsehole. Then a little bit of pain and then the feeling of something stiff and warm going deeper inside. Then the feel of the person's pelvis touching my arse and pressing down on it.
Then as a top, I wanted to feel that the other way around with the warm feeling of my dick inside a tight arsehole haha

 

[Robyntboy]

is it good to be tight or should I loosen up with toys first?
i love the feeling of toys inside me and I just know a real cock will be even better.
I hope he would like to do it regularly. or if not him, maybe I can find someone to do it a lot.
specially if theyre kinky!

 

[Theeym]

No, go in tight, he can loosen you up with fingerplay and by eating you out.
Yeah, toys never replace the real thing. Mind you saying that I'm balls deep into a Fleshlight

If he doesn't then I'm sure you will find someone to explore your kinks!
Thats how I discovered a lot of mine.

 

[Robyntboy]

what is the best way to discover kinks?
should i just let him choose which ones to do?
I really do want to try thigns like that I know its important to keep a man happy.

 

[Theeym]

First, think about your kinks. What do you enjoy and/or what have you always wanted to do?
Think about what you feel comfortable doing and see where you could go further with it.

Don't just give in to him if you're not ready for it.
Pleasing a guy is easy, getting them to come back for more is the real challenge

 

[Robyntboy]

Ive always wanted a man to take charge
spanks and tying up and some roleplay things have always got me excited.
I dont really know much about other kinks though. I dont want to say no to something without understanding it.
I wish there was a guidebook. lol

 

[Theeym]

Okay, so your main kink is dominance, that is a common one and can still leave you with room to say no.
But, once you into the moment I feel you will say yes to anything he wants from you.
The next step for that is the desire to be a cumdumpster.

Look at the type of porn you enjoy to figure out your kinks, you into anal and dominance but also look at what you fantasise regarding role play