Missed Opportunities
 

About this time last year my wife and I were on vacation at an all inclusive adults only resort. On the beach everyday there was a young guy in his mid-20's who was there alone. He had a great body (my wife and I are in our mid-30's and are both fit but he was an obvious regular at the gym) and I caught her checking him out multiple times but didn't let on that I saw her.

We fucked every day on that 10 day trip and sometimes more. I couldn't help but notice that she was freer and more animalistic than she was usually at home. I often wondered if she was fantasizing about the young hot guy while she was riding my cock. I hope she was!

In my head I had a plan that went as follows: remark to my wife that he couldn't get lotion on his back and maybe she should go over and help him. Invite him to join us on the beach. Invite him out for (more) drinks that night at the various clubs on the resort. Give my wife the okay to dance with him. When alone ask him if he'd be interested in coming back to our room for a little fun. Make it clear that we would be focused on my wife and that nothing would happen between us. If he accepted tell my wife that we were moving the party back to our room where is wasn't so noisy. Keep a constant supply of drinks in her hand and encourage her to keep in physical contact with him; dancing, sitting next to him, etc. Give him a thumbs up to make a move and reassure my wife if she balked at the idea.

When I suggested the lotion in real life she said she couldn't and try as I might she wouldn't go over. However, that night while she was sucking my cock with her ass in the air behind her she remarked that she figured that I would love to have this view from behind her. I played stupid and asked her what she meant. She said "I bet you'd like to be behind me, fucking me, while you watch me giving you head". She has known about my wanting to share her in a MMF situation for over a year now and I have been able to get her to open up to it as a fantasy in the bedroom. So, laughing, I replied "I could go try to find the young hot guy from the beach and ask him to join us"!

She slowly slid my cock from her mouth and raised her green eyes to mine, smiled and said "yeah, right" and went back to giving me an expect blowjob. She climbed on top of me and rode my cock hard with her eyes closed. I like to think she was fantasizing about the prospect of being shared with that hard bodied 20-something while she fucked me.

Anyone else have anything that ended up being a missed opportunity? Or any advice on how I could turn her mind around on the idea of being shared?

Great story. Seems like your wife is finding the idea hot, at least enough to tease you with it. You need to book another trip to a similar resort for early next year, and from now until then, when the timing is right, elaborate on the fantasy.

Thanks! Great suggestion too! And we are actually planning another trip for late April of next year. Until then I definitely plan on using the idea of a MMF threesome in the bedroom more and more. She absolutely loves the extra thickness that my extension sleeves provide and is learning (slowly) to take the large suction cup dildo that I bought.

After I take off the sleeves we always talk about how stretched out she feels and how its like she's just been with another guy. The suction cup toy is, as I said, slower going but I know that once she gets into the habit of it and what it does to her pussy she'll love using it and it will give her the experience of having two holes filled at the same time :) Another not so subtle hint at what I'm aiming for with the real thing!

great story
 

but its not really a missed oportunity

she is not ready yet

but shes getting there

That's true. But it feels like her agreeing to play to the fantasy in the safety of our bed is so far removed from actually committing to letting another man pleasure her. I hope you're right, that she is almost ready to make that leap... :)

its a process for some
 

also, she needs to be sure you will never hold it against her

Pretty much how we started out swinging...

Thanks, yeah, I think, if it happens, it'll be after a lot of encouragement and support. I want to see her get as much pleasure as possible and I know that if she opened up to it that she would absolutely love being utterly worshipped by two men.

Gives me hope! :)

Unless she ends up liking the other bloke more and fucks you off, I have seen it happen.