How To Start A Threesome.

I'm a shy creature when it comes to starting anything sexually. Once I'm comfortable, I feel like a Goddess incarnate, but until then it's red cheeks and averted eyes.

So here's the problem:
My room mate (also my ex partner, manny, best friend, occasional sex partner, etc.) and I took a backpacker in last week - a friend of mine recommended us as a good, safe, groovy place to couch surf while this fellow is checking out the island, and we said of course!
Now, this guy is beautiful, inside and out. Tall, lean, shaggy blonde hair, blue eyes, and a wicked great smile. German, so even an accent! First time I saw him was when I came home from work and he's just arrived, perched on our wall with the sun in his hair reading a book. I melted because, C'mon.. He READS! That's sexy.
He left a couple of days ago, hitch hiking this beautiful little island, but we've kept in touch.. We've been getting flirty.
One night when my roomie and I had smoked one, we were talking about a threesome.. He's interested in experiencing one, and I'm interested in trying it with two men.
The traveling fellow is younger than us both (he's 20, I'm 22. Room mate is 25), and inexperienced.. And shy. I SUGGESTED (without actually stating flat out what would follow) all of us having a bottle of wine when he drops by again on his way back.. He said "I'm game.". Now, I HINTED that the three of us would ALL be involved, and he seemed alright with that.
But he's young, and shy, and I don't know how he'd feel about the 2nd fellow there.

This leaves me stuck.

How do you initiate a threesome casually?
Do I kiss him first? Do my room mate and I start making out, then room mate places my hand on traveling fellow's leg?

Help! I can already feel my cheeks burning!

 

Sit between the two men and just put your hands on their lap at the same time and start playing around . . . go easy and let him get comfortable

 

You say that like the butterflies in my stomach would let me do that without my hands shaking

And what if he changes his mind? How do you play it off? I'd respect him, absolutely! But the embarrassment..

 

It kinda depends on how long you want to keep the other guy around. Drinks and a one night stand will probably be a one time deal I'm guessing. If you draw him in over time, I bet you can keep him around for a while. Sounds like a fun fantasy!

I'm curious; do you want to try double penetration, or just tag team? Also- what do you use for birth control in situations like this?

 

he's on vacation, it doesn't really matter how he takes it because he'll be back in germany soon enough.

are the schools really so bad up there that being able to read is that big a deal?

 

Walking into the room naked will get the idea across.

 

Please let us now how was it.

 

It's not the education, obviously every north american who went to grade school knows how to read presumably, it's the culture. Reading is not "cool". "Cool" is being a clubber and watching Jersey Shore and listening to hip hop, or some shit. People who read are automatically advertizing their own "uncoolness", "nerdiness", etc. The mentality is that you must be reading because you're not cool enough to do anything else, like get laid at a club by a guy/girl you just met who you're too cool to care about whether he/she knows your name or not.

it's a wonderful world people have built for themselves :sunny:

 

^^^^^^^^^^LOL^^^^^^^^^^

Agreed kind of ironic how we are destroying it too.................

 

Here's a plan that I once used.

Find out when the two men will both be in the room at the same time. Then, go take a shower, pretending you didn't know that them two are there together. Come out with the towel around your body and pretend to be shocked that they are in. Then, i don't know, do stuff that makes you have to bend over and stuff. Or, you can pretend to trip and fall on one of them, then look them in the eyes. Or, if you want, you can fake the towel falling off in front of them and... BOOM. Next thing you know, two holes of yours will be stuffed.

 

just get naked and tell them both to mount you. done.

 

Shaking hands are not a bad thing .... you're human after all

The embarrassment depends only on you. You can't have an answer without asking the question .... so it seems that you'll need to ask. But a negative answer is not exactly a slap in the face or an insult, so there is no real need to be embarrassed.
As long as you ask nicely, that is

 

unless they slap you in the face while saying "no, fatass!"

 

Oh gosh, so much to write!

Just need to get to a proper computer..

 

When I was going to CNA school the very first class had a comprehensive reading test as part of the class. The funny thing about this was I didn't sign up or pay my tuition till AFTER Class 1 was finished.

Here's the REALLY FUNNY part. One of the textbooks for this school was written at a FOURTH GRADE LEVEL!!!

I sure am glad I learned how to read. But then when I was a kid going to school if you didn't learn everything you were supposed to you were held back a year. Corporal Punishment was still in full force right up until Junior High back in the good 'ole days.

 

Seems pretty clear cut to me, if your roommate is down then focus on the other guy. Wear a short skirt, sit between them and when the wine is flowing make your move on him, touch him get and him in the mood. Bend over and give him head and leave it to your roommate to join in from behind you. Guys tend to be a lot more agreeable when their dick is in your mouth. If he would ever be willing then you will have him on the hook, if not, cut your losses and fuck him one on one. You just have to go for it.

 

Do tell!

 

It sounds to me like you've already laid the grown work here. I think you may be kidding yourself if you think this 20 year old backpacker is inexperienced. My suggestion is to be very straight forward with him. When the opportunity arises, or you sense that the timing is right - just tell him exactly what you have in mind. The worst thing he could do would be to say no, but I doubt he will. I mean it's the only sensible way to find out if he's really up for it. You wouldn't want him to just go through with it, if you started, just because he was too afraid to say no - right (and don't poo poo that notion - it happens.)

 

You're going to have to be sure the two guys are ok with each other.

 

Any updates?