Conservative Approach to Initiating Sex?

[SayWhat]

I'm not usually the person to initiate anything sexual. I'll flirt, but I won't throw the first punch if you catch my drift. I'm also HORRIBLE at taking hints.

So here's my question:

What's a fairly conservative way to initiate sexual activities? I don't want to go straight for the package or do something that's extremely invasive just in case I'm misreading the signals. But at the same time, I don't want to treat it like a business meeting by sitting down and talking about it. That's kind of a buzzkill.

I'm not a prude by any means. I'm just not used to taking the lead. I guess you could say I'm a little shy in that regard.

Thanks for your input!!

 

[HunterM]

Meet him at a bar that plays loud music. Because of the loud music, you're forced to lean in much closer to speak in his ear. When he is talking, you purposely lean in closer to his face to listen to him...to establish a comfort zone. Meanwhile, make "more physical contact (touching his hand, thigh, shoulder)" as suggested by Loki81. I would touch more on the knee/thigh area...and move up.

 

[hylas]

i usually make a move that can be easily accepted or rejected. take his hand and hold it, put your hand on his hip, or his knee... if hes not interested, he will withdraw his hand/push off your hand. if not, kiss!

 

[SayWhat]

We've already stayed at each other's places several times. When it happened, we always slept in the same bed. We touch each other constantly and sometimes it gets a little intense. But it's usually with a playful tone, so I'm having a hard time jumping from playful touching to "Bow chicka wah wah!" Haha.

 

[hylas]

so let me get this straight... you frequently share the bed with this guy, playfully and intensely fondling each-other, but youre scared you might be "misreading the signals"?

you are hopeless. you will die a virgin, surrounded by cats.

 

[HunterM]

you are hopeless. you will die a virgin, surrounded by cats.

I had to That's a good one.

Here's the "conservative" approach the next time you guys are in bed:
1. Move in close to him.
2. Place your hand on his stomach, rub his furry trail.
3. Then slide your hand lower...to massage his cock.
4. Don't forget to grab his balls either.

Here's the non-conservative approach when you guys are in bed:
1. Position your mouth and wrap his cock in it.
2. Don't forget to suck either.

Let us know how it goes. I'll be around for the next 6 months...waiting for your update

 

[SayWhat]

so let me get this straight... you frequently share the bed with this guy, playfully and intensely fondling each-other, but youre scared you might be "misreading the signals"?

you are hopeless. you will die a virgin, surrounded by cats.

Ehh there's a complicated aspect of this that I failed to mention at risk of sounding too cliché. He identifies as straight. I'm kinda done looking for signals as to whether he's curious or not, because he clearly is. Straight guys just do NOT touch me the way he does!

But when I've asked previously, most people say things like "The next time he touches you like this, grab his cock!!!!" and I think to myself "Before I became comfortable with the idea, I would have punched the shit out of a guy if he randomly grabbed my cock!"

So I was trying to find a neutral approach. Not a "OMG! How do you tell if he's secretly gay?" thread, but a "How do you take it to the next step without making someone (gay or straight) feel like they just got sexually violated?"

Hope that makes sense!


As for the hardon thing, I've noticed after we wrestle around (especially if he's just in his boxers) he walks away with a bulge. Not full-on, ready to rock and roll, but definitely bigger than before. He always randomly jumps up, speed walks out the door, and hides in the bathroom for like 10 minutes. It's just another reason I don't think he's comfortable with the idea yet.

 

[SayWhat]

^ that's a horse of a different color.

have you ever kissed him? if you really think he's gay or bi, that's probably the best place to start, long before you attempt to initiate sex.

Maybe I'm just weird, but I think a kiss on the lips is way more intimate than most sexual activities. I'll get off with more people than I'd kiss on the mouth.

The thing is, I've tried to be VERY cautious of his personal space because I don't want to make it uncomfortable. He has done the complete opposite, though. Lately it's like he has to find some way to touch me all the freakin' time! Whether it's laying on top of me, pinching my nipples, tickling me, playing with my hair, slapping my ass, etc. It's practically non-stop.

BUT it's like it builds momentum to a certain point and then his "gay alarm" goes off and he abandons ship! I don't initiate any of this activity. I just kind of let it happen and enjoy it. It seems like he's waiting for me to take the final leap, though.

 

[HunterM]

It seems like he's waiting for me to take the final leap, though.

Yeah...waiting for you to grab his cock

He's definitely into you. Straight men may lay on top of each other like wrestling. Straight men may slap asses in the locker room. Straight men ...may...pinch nipples other than their own. Straight men don't tickle others. And straight men definitely DO NOT play with other men's hair.

So here's what you do. The next time he's playing with your hair, play with his hair and say, "I love playing with your hair." 3 months later while in bed, rub his hairy trail and say, "I love playing with your hair." 6 months later, then rub his cock and report back to us.

 

[KaraBulut]

Communication is what clears up confusion- whether it's with your confused friends with their mixed messages or whether it's in advice forums where details are important to know the best advice to give you.

This whole thing is really more complicated because you probably haven't told him that you have an interest in guys.

You're not wanting to talk with him about it. You're also not giving the whole story from beginning to end in this thread either.

It's not easy to give you the best advice unless you tell us about your friend, how you know him, does he have a girlfriend, how did this wrestling and sleep-over thing get started and what exactly happens when you sleep in the same bed? And exactly what do you want from the whole thing?

 

[kguy3387]

maybe next time you're in bed together, you could try cuddling with him!

 

[SayWhat]

This whole thing is really more complicated because you probably haven't told him that you have an interest in guys.

Actually, he's known I like guys since the day we met about a year ago through some mutual friends.

You're not wanting to talk with him about it. You're also not giving the whole story from beginning to end in this thread either.

I wasn't wanting to talk to him about it, but I did anyway because our friendship was suffering over it. I was having a hard time because he was doing all of the above, and then when he'd spring a semi he'd make a comment like "I gotta call up this girl to get me off tonight!" and I was thinking "Well feel free to swing by any time you need some foreplay to get you in the mood, asshole!" Haha.

BUT I did talk to him. I told him that we needed to set up some boundaries here so there weren't any miscommunications. I said that I enjoyed our wrestling and touching, but it also sent some confusing signals and made it seem like he was sexually interested. He stopped for a week or two and then started up again, taking it even further now.

When we talk, he says things like "I'm straight!" and "I'd never mess around with a guy!" And I'm not trying to disrespect his wishes, but his actions are speaking louder than his words. Especially since I know I said those same exact words five years ago, and now look where I am.

It's not easy to give you the best advice unless you tell us about your friend, how you know him, does he have a girlfriend, how did this wrestling and sleep-over thing get started and what exactly happens when you sleep in the same bed? And exactly what do you want from the whole thing?

I explained above I met him through some mutual friends. He does not have a girlfriend, but there are a couple girls he calls up when he's horny.

The sleep over thing started when we were renting movies. He'd put the movie on in his room and we'd lay on his bed and watch it. The first time I slept in his bed was because I fell asleep in the middle of a movie we rented.

When we're in the same bed, nothing exciting really happens (unless you count the fact that he sleeps in his silky boxers! Haha.) He lays unusually close to me, but it's usually on his back. It's not like we're spooning or anything. He usually wakes up before me, so he'll caress my ear lobe or gently pinch my chest to wake me up in the morning, but that's pretty much the extent of the bedtime touching.



Sorry I didn't include all the graphic details in the original post. It was meant to address the idea from a generic standpoint to give me some ideas.

 

[KaraBulut]

Actually, he's known I like guys since the day we met about a year ago through some mutual friends.

That's a very important piece of the puzzle.

A lot of guys do have a need to be around other guys. And if it's considered "safe", then there can be physical contact because they don't perceive it as sexual.

If he knows you're gay, then it's clear that sex is a possibility.

I told him that we needed to set up some boundaries here so there weren't any miscommunications. I said that I enjoyed our wrestling and touching, but it also sent some confusing signals and made it seem like he was sexually interested. He stopped for a week or two and then started up again, taking it even further now.

When we talk, he says things like "I'm straight!" and "I'd never mess around with a guy!" And I'm not trying to disrespect his wishes, but his actions are speaking louder than his words.

There's no argument that this guy is confused and he is sending out mixed signals.

You did the right thing by setting boundaries. If you were straight and this were a girl getting into bed with you, putting her hands all over you and talking about horny she was then getting out of your bed to let some other guy bang her, you'd set the boundaries and say, "Look- if you're interested, speak up and stop leading me on here. Otherwise, stop playing games, get out of my bed and stop teasing me."

Sorry I didn't include all the graphic details in the original post. It was meant to address the idea from a generic standpoint to give me some ideas.

Important details.

Here's the bottom line: you're interested and this confused little boy is being a big tease. If you're both single and you're sure that a little sucky-fucky isn't going to ruin the friendship, then it's all fair game.

But it seems like this boy wants to stay on the shallow side of the pool instead of going to the deep end where all the grownups are. He's just not ready and while he wants to tease the gay guy and enjoy the attention, he doesn't want to consider that he might- just a little bit- want some dick-play.

Honestly, maybe it's time for you to swim back to the deep end and find a real man who isn't afraid of a little backstroke and is willing to dive in with you.