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Strategy to sexual intimacy with my straight friend - I have one chance!

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Hi friends,

I write seeking some help. Here's the objective: "Play" (have some sexual intimacy) with my straight friend. Blowjob and things like this.

About me and him:
I'm a 25 year-old guy from Italy, good shape and good-looking, 1,85 meters tall. I have a girlfriend for 2 years now and I love her. I'm not the one who likes to put "labels" to one as bi, homo or hetero, although most people do. I am just curious about male to male contact. I never had any "gay" contact. But I'm attracted to good-looking guys. Luckly, I've never felt guilty about my feelings.

He is a 28 year-old guy, very good shape, a doctor, 1.80 m tall. Some friends tease he is gay. However he is straight, so far as I know. He has some kind of "problems" when it comes to "gay pranks", because he gets angry easily. He was kind of my best friend in college.

We live in different cities right now. There's an event from our college friends running next week and I managed an hotel room for only us both, with his consent :D. It will be only one night, so I have only one chance.

We will arrive in the hotel at night, probably drunk. My preliminar thought is to take off my clothes, except my underwear, as soon as we arrive hehe

What I ask you is, what do you think is a good strategy to reach my objective?

Thanks!
 
I think your best bet is to use him as masturbation material in your fantasies, and find someone who is more willing to have sex with you to explore with in person.

Just because you want him doesn't mean he's in the least bit interested in you, and it could end very badly.
 
I think he has a hidden desire too. Once in his house he was shirtless and asked me to dance with him with hands together and bodies close. It was me that refused because I was afraid...
 
I think your best bet is to use him as masturbation material in your fantasies, and find someone who is more willing to have sex with you to explore with in person.

Just because you want him doesn't mean he's in the least bit interested in you, and it could end very badly.

First, welcome to JUB! :wave:

Second, I agree with borg. Any quick conquest you feel will not be worth damaging the relationship. If you decide to go ahead, let him make the first move, very clearly.
 
So, what's you goal? To have some sort of sexual contact once just to do it? I don't think it's worth it especially if all the seduction is up to you.
 
Yes, my goal is to have sexual intimacy with my best friend. For years I've been curious about sexual intercourse, that could be only a blowjob, with a cute friend, so that we can keep it secret and maybe do it again another occasions.

For what I have read and talked through internet, this is not uncommon among guys, but a few would admit that publicly.
 
If it's only about sex, why not go to a gay bar or dance club and find a one-night stand? Rent a hotel room, take him back, work some magic and you got your sex. If you're uncomfortable with proximity, just go further away from home. Less chance of being 'caught' by someone that knows you or your girlfriend.

Don't trash a friendship over sex; it isn't worth it.
 
What nobody has yet said, but everybody is circling around, is that your thread makes you sound like a predator. Do you consider yourself to be one? If not, you should ask yourself what creates that impression.
 
What nobody has yet said, but everybody is circling around, is that your thread makes you sound like a predator. Do you consider yourself to be one? If not, you should ask yourself what creates that impression.

Hi Rolyo, I didn't understand what you mean by predator, could you explain it?
 
Maybe you got a wrong impression of my intentions.

Let me explain clearer. I would not force anything. I imagine everything to be spontaneous. I must be a will of both of us. Nothing like big moves, but small steps.

I just imagined it could start with innocent invites such as "Hey, bro, come here, sleep with me" or "Hey, bro, let's take a shower together" or even "Do you want me to teach you how to dance?".
 
if a straight girl wanted to seduce you, what advise would you give her?

just follow that same advice yourself.
 
What nobody has yet said, but everybody is circling around, is that your thread makes you sound like a predator. Do you consider yourself to be one? If not, you should ask yourself what creates that impression.

^This.

Change the gender of your friend to female:

"She's" your best friend from school. You've set it up so that you and "she" are sharing a hotel room. You're going to get "her" drunk and have sex with "her" because you're curious about what it would be like.

People would call you a predator and a rapist for doing that. You're a fine line away from "She wants it. She's asking for it."

And on top of it all, it's a really shitty thing to do to a friend.


scopelli said:
I just imagined it could start with innocent invites such as "Hey, bro, come here, sleep with me" or "Hey, bro, let's take a shower together" or even "Do you want me to teach you how to dance?".

This is not what you want to hear but life is not a porn film. People have feelings. Actions have consequences. Your problems are much bigger if you can't empathize and understand that friends don't take advantage of and use other friends to act out fantasies.
 
Instead of trying to seduce him, why not try being honest with him? Tell him you are attracted to him and interested in him sexually. Let him decide for himself. You risk losing his friendship by your tricks.

Also, you might want to consider your girlfriend. Remember her??
 
Hi Rolyo, I didn't understand what you mean by predator, could you explain it?

You are trying to plan a situation where you can have sex with your friend, who has never expressed any direct interest in you OR guys, and is actually homophobic. You are here asking for advice on the best way to create that situation (NOTHING spontaneous about that), and you don't stop to consider how unlikely it is that your friend actually WANTS it to happen. That makes you seem like a predator.

And yes, girlfriend. A lot of people with - let's be political - "bi" tendencies kinda assume that "it doesn't count" if it's with another gender. It does. It's cheating, and it's a scummy thing to do to someone you are in a relationship with.
 
Ok guys, thanks for your answers. You made me think of matters I never thought about. I'll reconsider my goals.
 
^ I'm glad you've changed your mind. To have ulterior motives to advance sexually onto your friend is predatory in nature. You already know he is sensitive towards having his sexuality challenged with pranks, so why cause him that emotional stress and harm by keeping him captive in a hotel room that he'd be unable to escape from? That's a terrible position to force onto your friend. Respect his privacy and pursue your sexual exploits with someone who is confident in their male-on-male sexuality.

Not to mention I find it disrespectful to your girlfriend of 2 years that you'd be so willing to cheat on her with your friend. Just because it's another guy, it doesn't mean your commitment and relationship to her holds any less value.
 
I agree, it sounds exciting and as harsh as it sounds, you're the type of guy that I stay away from when I date/go out with guys. I need sexually mature guys - those that either have been there and done that or aren't interested. What you're doing is cheating on your girlfriend.

If you don't see it as cheating, don't see it as long term then I suggest breaking up with her and explore your sexuality. Once you've had fun and are ready to settle down in a serious relationship then so be it.

As someone has pointed out being honest about it with your friend might be the better way around it too.
 
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