My Conundrum

[effjaybee2023]

I have had a crush on a certain divorced grandmother (call her Pauline) for a number years now and I don't know how to approach her about spending a night in bed. When I see her I cannot help but undress her in my mind. She is voluptuously full figured and is 60 years young, my kind of woman. I am a pretty direct gentlemen so in most circumstances I would simply ask her and wait for her response to my proposal. The conundrum is....both of us have a mutual friend, call her Mrs. C. Pauline and Mrs C have known each other for about 30 years, they confide a lot in each other. I met Pauline through Mrs C. As Mrs C puts it, she knows more about Pauline's sex life than she wants to know, she tells her almost everything about the men in her life, and I learned because once in a while Mrs C will share something in confidence with me about her friend. Should I ask Pauline to sleep with me, I am certain she will share that with Mrs C, and Mrs C and I have shared her bed on several occasions. I do not know how much, if anything, Mrs C has ever confided with Pauline about the two of us. Perhaps Pauline has connected some dots since Mrs C and I have traveled together and have shared the same hotel room? Perhaps Pauline knows a lot and just does not say anything to me? I do not want to come between Pauline and Mrs C, nor do I want Mrs C upset with me for wanting to sleep with her long time confidante. I have thought about a threesome with them. Just not sure how to proceed, suggestions???

 

[Lady2020]

IDK. Maybe condensing what you're trying to say may help?

 

[effjaybee2023]

Simply said....I want to go to bed with my friend's long time confidante and I am not sure how my friend would react to that situation.

 

[IrisAlthea]

I have had a crush on a certain divorced grandmother (call her Pauline) for a number years now and I don't know how to approach her about spending a night in bed. When I see her I cannot help but undress her in my mind. She is voluptuously full figured and is 60 years young, my kind of woman. I am a pretty direct gentlemen so in most circumstances I would simply ask her and wait for her response to my proposal. The conundrum is....both of us have a mutual friend, call her Mrs. C. Pauline and Mrs C have known each other for about 30 years, they confide a lot in each other. I met Pauline through Mrs C. As Mrs C puts it, she knows more about Pauline's sex life than she wants to know, she tells her almost everything about the men in her life, and I learned because once in a while Mrs C will share something in confidence with me about her friend. Should I ask Pauline to sleep with me, I am certain she will share that with Mrs C, and Mrs C and I have shared her bed on several occasions. I do not know how much, if anything, Mrs C has ever confided with Pauline about the two of us. Perhaps Pauline has connected some dots since Mrs C and I have traveled together and have shared the same hotel room? Perhaps Pauline knows a lot and just does not say anything to me? I do not want to come between Pauline and Mrs C, nor do I want Mrs C upset with me for wanting to sleep with her long time confidante. I have thought about a threesome with them. Just not sure how to proceed, suggestions???

There is no fool proof way of having your cake and eating it.
If you find one, please report back.

 

[effjaybee2023]

I will let you know; it is way more than cake that I want to eat!!!

 

[HumpDayHoratio]

My opinion and mine only.

Don’t go there. A bird in the hand. You’ve got a friend, with benefits, and a confidante. That my friend is worth its weight in gold. Don’t fuck that up, just to try and satisfy a fantasy.

Maybe suggest a trip with all three and have the ladies stay in separate rooms. Something organic may happen?

 

[Dapperguy]

Listen, and listen well. You need to take the hard line. Tell Mrs C. to away and raffle her doughnut. Tell she’s in the way of you getting Pauline on her back. Be direct. Be resolute. After, tell Pauline you’ve had to have words with Mrs C. She’ll appreciate your candour. She will look upon you as a leader to lead her. Show fortitude and you will win her.

 

[RoperTrace]

Gee, I don't know, what could go wrong? Do you even know Pauline as a casual friend? If not it seems like a leap to ask her for sex right out of the chute, so to speak.
If Mrs. C. is the chatty type, she's probably already clued Pauine in on your infatuation. If you value what you have with Mrs. C, you may want to reconsider. If all three of you are friendly already, maybe HumpDayHoratio's idea of a group trip and seeing if anything develops organically makes some sense. Pls keep us posted.

 

[LadyElsbeth]

My opinion and mine only.

Don’t go there. A bird in the hand. You’ve got a friend, with benefits, and a confidante. That my friend is worth its weight in gold. Don’t fuck that up, just to try and satisfy a fantasy.

Maybe suggest a trip with all three and have the ladies stay in separate rooms. Something organic may happen?

This seems like the best advice. ☝

Women can be jealous of one another. If you have a good thing going with Mrs. C, then you may truly screw that up by trying to sleep with Pauline as well. Also, from what you say about their friendship, it sounds like she would know you are already sleeping with Mrs. C and most women will not tread on their friend's territory. Not if they truly respect that friendship and person.

So you have to ask yourself if you are willing to lose Mrs C when Pauline may say no? Also, you have not indicated if you want a long term relationship with Pauline or just a "one-night only fantasy come true" kind of scenario. If it's one night, definitely don't do it. Try the trip idea that Horatio said earlier in the thread. It may work out for you and a three-way would definitely not interfere with anyone's relationship.

 

[effjaybee2023]

An update; I found out through Mrs C that Pauline has an important family matter this is occupying almost all her time right now so I feel it best that I do nothing until that matter resolves itself. As for the idea of a road trip, the three of us, that has been casually brought up. I would welcome that. I have never been with Pauline alone; I see her only when I am with Mrs C. I would like more than a one night stand if possible. Again, I have no idea how much Pauline knows, if she knows anything or if she has connected the dots by herself. Women do that; they can be very intuitive.

 

[jehoram]

The only way to see if Mrs. C might be perturbed by your sleeping with Pauline, or if Pauline would be willing to sleep with you, or if it would actually work out amicably, is to talk with them and say what's on your mind. It's a given that, if you start a sexual relationship with Pauline, Mrs. C is going to know about it. So would that be a bad thing?

Be clear in your dialog that you don't want to hurt anybody, and let them know that it won't happen unless you're clear that both women are okay with that. I can see Mrs. C being unhappy about sharing you, given that you might bring home a disease that she doesn't want to deal with, so you have to take that into account as well.

As for everyone else's advice, I'm not going to say "ignore it." But you are really the only person in a position to evaluate the situation, since you know yourself and you know the two women personally.

 

[effjaybee2023]

Because of where I am employed part time, I am able to get nice discounts on items of interest to Mrs C who has asked me to get some items for Pauline; I have never refused doing that because of the relationship between the two women, and I would go out of my way for Pauline should she ask.

Last November Mrs C and I went out of town together for 8 days; Pauline volunteered to take us to the airport and pick us up when we returned. Whenever I travel with Mrs C we share the same bed at night. Whatever Pauline thinks of that practice I do not know and never asked her directly, nor do I know if Mrs C and Pauline have talked about that either. I have stayed with Mrs C at her daughter's place and even there I slept in the same bed with Mrs C.

The old saying "Never judge a book by its cover" certainly applies. To see Mrs C you might get one impression; yet, when the mood is right she is the most affectionate and passionate women I have ever met, bar none; and when the mood was right she would be the fire starter and I really loved that. When the love making was over we would spend the rest of our time in bed in the nude and as close to each other as was physically possible. There have been nights in the nude in bed that we did not get passionate; she taught me to enjoy the emotional and spiritual warmth of being that close all night long. No one has known better how to push my buttons and light my fire than her, and we never talked talked candidly about physical pleasure. I can say that I have never had a purely physical experience in bed with Mrs C; all the experiences were very sensuous and most affectionate. She had a saying "You can always find someone to have sex with" meaning...you can always get physical with someone; it's the emotional and spiritual that makes the experience magical and memorable.

While Pauline shares almost too much with Mrs C about her escapades, I do not know how much Mrs C ever tells Pauline in return.

I am not concerned about catching something from Pauline; she is a retired nurse and I am pretty sure she has had only one bed partner in the past ten or more years. I get it about being careful in bed because I love giving a woman oral pleasure and would never do that unless I was comfortable she was super clean.

Perhaps it is just a fantasy of mine to sleep with Pauline? I can say this, as close as Mrs C and Pauline are, they are different in some ways as well. Then there is the old saying "Friends can become lovers, but lovers cannot become friends." Mrs C and I never connected to have sex; I would connect with Pauline to get physical with her.

 

[Diosax]

Seems to me that you should have an honest conv w mrs. C first unless you want to jeopardize your friendship and relationship with mrs c.

 

[Britva415]

I do not know how much, if anything, Mrs C has ever confided with Pauline about the two of us.

What do you think about finding out, by asking Mrs. C next time she talks about Pauline's sex life again, whether Mrs. C has reciprocated the over-sharing?

What do you think about the general idea of expressing fantasies of yours to Mrs. C, with or without hopes or expectations that she'd want to satisfy any of them? Just sharing for the sake of conversation? Is this something you already do with her? Is this something you'd consider beginning, in order to establish a precedent or even a habit of doing so?

Then, when Mrs. C brings up Pauline's sex life again, whenever that will be, since at that point you'll already be in a conversation with Mrs. C about the sex life of the two of you and with Pauline as a tangential subject at the same time, raise the stakes of your habit of sharing your fantasy life with Mrs. C by revealing the interest in Pauline?

 

[bestkeptsecret678]

I’ll go contrarian here, just to balance out all the advice.

Be bold, shoot for the moon. Let them both know that you’re physically interested in them both, and that you also value their friendship. Let them decide if they think you should have both cakes and eat both too.

But, you have to be willing to live with the consequences, which could be both, one or neither.

 

[bestkeptsecret678]

Oh… I forgot to add; that both will likely be much more complicated than you think.

 

[effjaybee2023]

All this conundrum would go away if and only if Colleen would reply to my emails. Mrs C and Pauline live about three hundred miles from Colleen; they know nothing about Colleen; she knows nothing about them. Unlike Mrs C and Pauline, Colleen always kept the lights on and made sure I had a lot to look at especially full frontal nudity. She was the first lady I was with whose pussy fur was the same color as the hair on her head, a lovely silver gray which I found very very sexy. The more I suckled Colleen's nipples, the more she spread her legs apart. On Super Bowl Sunday several years back Colleen and I had planned to spend the entire day and night together until I had to head to work late Monday morning. We were out for a short drive prior to our brunch reservation at a very popular state park. I was driving and pulled into a trailhead parking lot because I had a bag of goodies for Colleen from Bed, Bath and Beyond. As I reached behind the seat to get her goodies, she smiled and told me she had something for me too; she opened up her coat; the dress she was wearing certainly emphasized her 38Ds marvelously. She invited me to slip my hand down the front of her dress; there was no support, no bra, her nipples were bullet hard! OH MY, YES!!! I did all I could to keep myself from making a mess in my boxers. Thinking about it years later, I wonder how she would have reacted had I slid my other hand under the hem of her dress and between her thighs while I massaged her twins? All during brunch she kept squeezing my thigh. When we got to our suite, she was down to panties only in no time. Did I mention Collen was ten months older than me, was 65 years young at the time, and had not been to bed with a guy for over twenty years prior to our connecting? Colleen is the reason I have a real affection for sexy grandmothers in their 60s! I only wish I had given Colleen oral pleasure because when she did climax, it was amazing and memorable, nothing fake about her getting off!!! And the first thing she did for me was put a nice lip lock on me, take her time nibbling, then swallowed everything. I thoroughly enjoyed how she gave oral pleasure, she was in no hurry, the way I prefer it, just like I love taking my time giving a lady a nice long licking session.

 

[effjaybee2023]

https://www.***********/s/5qcsyv9sv14tu9d/PXL_20230402_002804952.TS.mp4?dl=0

This is what I imagined how it would be in bed with Colleen and/or Pauline, or whomever I would meet who loved being suckled and given a good LONG licking. YUMMMMMM