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Not Sure If Hes Ready

I've been with my SO for five years and I love having him try new things. I do love women but haven't dated or done anything with a woman since getting together with him. I've had two casual ********** before getting with him and only one worked. One was with a married couple, the husband was a coworker. It was fun, no strings attached kind of thing. The other ********* was with a woman I was dating who also happened to have a boyfriend. I had fun but then she started the "My boyfriend likes you better than I" type of jealousy, not unusal aftermath of a person who wasn't ready for a *********. Lest to say, my relationship with her ended after that as well as a great friendship. Now I know I'm perfectly capable of casual no strings attached fun to be had with inviting a women I deem suitable for bringing into the bedroom but I'm not sure about my SO. He grew up very sheltered and I have been the one to journey him through many first. Any other males like this that could give input on what would be best? Better to have him know the other person slowly ( this also factors a chance at developing feelings though) or find someone (that I know has been tested ect.) and surprise him?
fortysixandtwo fortysixandtwo 22-25, F 6 Responses Feb 15, 2012

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I noticed your story and couldn't help notice the similarities...with a couple of exceptions. One, I am a male. Two, I am straight.....what is similar is that before I married my wife, I experienced quite a few 3-somes (mfm), and enjoyed one couple (they wern't married either) for over a year.
Since I have been happily married, I have had super strong feelings about having my wife enjoying the excileration and feelings of a *********. I have a feeling that she fantasizes about it 'cause she knows of my past, but I also find it depressing that she says she'll not go there. Gads! It would be great just to see her jack a guy off while I watched. It would be a dream *** true if she actually sucked him off....or more!
My only hope is that if I keep telling her about my fantasies and my past experiences, she just may want to go there. It upset me one time when she said she didn't want to talk about my experiences. I don't think she knows how important it is for me to share them with her, but i'm trying to understand and not bring it up. She likes bringing up her old friend, and that get's me excited.....and I have encouraged her pursue it again. Share your thoughts? If something works out.....i"ll share the secret.

Like Firegod74 said have a good drunk night like his birthday for example new job or whatever. Arrange it with someone you prefrably know to run into you inviter her back. Have her flirt with both of you during the nite then get him alone a say you think you can make it happen if he's into it.
If he shows any interest in it even reluctantly. Go for it.
Hell go for it! Lol

Did you pick a way yet? :)

don't over-think it......most of us don't!!

I like the drunken debauchery method. It looks more accidental. And if he isn't into it then it just goes away.

practice,coaching, patience and theirs always that risk like your friend i've noticed that when men are the ones to introduce women to things they seem more confident and vice versa, but when a more experienced woman come to the table with more men tend to feel intimidated, specially the sheltered ones and again same for women they freak out and tell the men you f** perve.. but good luck in your adventures but be careful the jar you open curiosity didn't kill it just made him/her roam further and further making us or some insatiable for the knowledge of happiness and fulfillment in the wrong areas for some and good for others...