I received a text from a childhood friend the other day asking for my thoughts/advice/opinion on a potentially delicate matter. You see, my friend could write her very own sex story compilation, as she is a single woman in her early forties, and a total cougar. I applaud her.
The question was, have I ever had a threesome with two men? My answer was…well, it’s not important. Moving on…she also wanted to know what I thought about it. Allow me to elaborate.
True Sex Stories – (in)Decent Proposal
A little background just to get you up to speed. After a very unhappy marriage, my friend (a self-proclaimed hopeless romantic) took to online dating. She hasn’t found any longstanding love connections, but plenty of sexual connections – and she’s enjoying every single one of them. (Bravo!) Even though she hasn’t found fairytale love just yet, she did connect with someone with whom she has become good friends. She definitely would like something more, but he isn’t looking for a relationship. So they have evolved into a “friends with benefits” arrangement.
In his early fifties, this silver fox had a sex story of his own making in mind for my friend. You see, she confessed to her lover (let’s call him Mr. Fox) that very few men actually take her pleasure into consideration. Although she does try to educate, as any good cougar should, it can be a bit frustrating. This too she expressed to Mr. Fox. His solution for her, a sex story trifecta, a threesome.
The Details

My friend appears to be living the life of a sexually prolific, confident woman. But despite her catalogue of delicious sex stories, she says that she is far from confident. Especially when faced with this decision. She said that if she was even to consider this fantasy sex story she had two requirements:
- It couldn’t be another woman – she didn’t want to compete, she wanted to be the focus (again, Bravo!).
- The man couldn’t be married or dating. Single only.
Time to Decide
She and Mr. Fox agreed on her terms and now all that was left was for her to decide. Did she want to? Was this going too far? There were so many questions. Whether she realizes it or not, all of her considerations center around her beliefs on sex, which stem from her upbringing. No matter how liberated she has been lately, pushing these boundaries and having to make a bold decision understandably exposed some cognitive dissonance.

Mr. Fox, of course thought his proposal would be liberating for her, and I certainly don’t disagree. (Just look how I write Ms. Elizabeth Bennet in “The Poor Darcy” series.) My only thought to help her determine whether or not it was the right scene for her was one simple question. Would she be participating in his sex story or would he be participating in hers? There’s a lot of mental prep that goes into true sexual liberation, and part of that prep is how we view regret. It’s imperative that she know exactly how, and for who, this sex story will be written, because it will be with her for the rest of her life.
She must also realize that she likes this man a lot, even though he has been explicit about his lack of desire for commitment. She trusts him, which is a huge consideration. But is this what she truly wants?
Bottom Line
Bottom line, is this for his pleasure or hers? He can say it will liberate her, but he doesn’t truly know that. Honestly, if he knows she’s not very confident he could be using this persuasion technique to his advantage. She must know if this is an experience she wants. Is this a fantasy she’s been curious about? Is this experience in line with her beliefs around sex and sexual expression? If so, then he would be a safe person to explore it, if not then she must ask herself the dreaded question – “Would I be doing this so I don’t lose him?”
Sex Ed – The Moral of the Story

When making decisions people often seek to relieve their decision making dissonance by making their choice more attractive. Let’s just call it “justification,” particularly when our behaviors don’t match our beliefs. Often times people will justify their way to a “yes” just to please or keep someone. There are many men and women who deep down, hope that one day a lover will commit. Until then, they don’t want to lose them because of a “no.” Let this be a sex ed lesson – When we are writing the chapters in our sex stories, we must consider the true source of our motives, as well as the motives of others.
When faced with pushing the boundaries and expanding sexual horizons you must resolve your own morality and make sure you won’t regret it later. You don’t answer to society, your friends, not even your parents – you only answer to yourself when the silence seeps in. If you have any doubts, then press pause.
WWYD?
In my opinion, I don’t think Mr. Fox’s proposal was indecent. If sexual exploration which leads to liberation is what my friend wants, then by all means – Carpe Diem. I want people to do what they want to do (safely, of course) and experience their best life…and if a threesome is it, then hop to it! But I want this to be for her, not for him…he can worry about himself. She’s a smart cookie and I love that she’s having fun…and I want her to live it up…on her terms!
So, what would you do if you were my friend? Consider all the variables we’ve covered and let me know in the comments.
Speaking of Sex Stories…
The newest short story in “The Poor Darcy” series is available on Amazon Kindle. I actually had a reader reach out and tell me that he, yes ladies and gents, a man, really wants to ahem…you know…with Elizabeth Bennet. Have a look at “Mr. Darcy – An Exchange of Power” and see Mr. Darcy as never before…not even as he was in “The Pemberley Estate Series.”

Mr. Darcy – An Exchange of Power reacquaints the wealthy Elizabeth Bennet with the object of her fantasy, the humble Fitzwilliam Darcy. When last they parted, Ms. Bennet had established that men were at her leisure, not the other way around. But since their last farewell, her fantasies have been haunted by the humble Mr. Darcy. Upon his return from town she is forced to reckon with the strength of her resolve, and determine if he is her lover, or if she is becoming his.