Candid Conversations
 

I'd love to read about situations where you found yourself part of an intimate group conversation and how it progressed to that point. Was it a one-and-done conversation, or did it lead to more candid/intimate talk at a later time?

I recently had a fairly long conversation with my fiancée and two of her girlfriends (all in their 20s) that was hot while it was happening, and even more so as I keep thinking about it... especially since I spend a lot of time with them.

We were lounging around after dinner, and everyone had a couple of glasses of wine at this point, which probably helped things take off. I don't recall exactly what triggered it, but the topic of tattoos came up. One of the friends wants one, and it led to a bunch of talk about why or why not she should get one, and if she did, where she should get it. It prompted a bunch of questions, which jump-started the three of them asking about what "guys" like.

The first really interesting topic to me was breast size. I was a little surprised that each of them had at least thought about going to a bigger size. The biggest turn-off for all of them was the scars and fake look of some enhancements. And NO, I didn't get to see a line-up... unfortunately... even though I tried ;). Maybe it was just them, but they couldn't talk about their breasts without sticking their chests out, pulling their shirts tight, or touching them. It was almost subconscious for them.

I joked that I've never been around a group of guys discussing the size of their dicks and what women wanted... and like I wasn't sitting there, they started talking about what size was too big and what size was too small. I thought it was interesting that none of them could really say an inch number. It was all length and girth based on hand gestures. Things like "this big", holding up their hands. We didn't have a tape measure, but each of them way overestimated how many inches something was. My fiancée (L) has an iPhone pro max 12, and from online measurements, it is almost 6 and a half inches long. They were all kind of surprised by that, lol. I asked what size the biggest real or fake dick they have had is and never got a real answer from the girlfriends, but it was funny watching them think about iPhones :D.

Pubic hair also came up, and you would have thought it was a market research focus group. They all like being completely shaved (sorry, bush lovers), and they all get tired of shaving. I was asked what I like, and I told them bare, which led to "Why?".

It got a little late, but I wondered how much further the talk would go. I obviously want it to start up again, but who knows if it will. At the time, the talk just flowed, and it didn't seem forced.

I'd love to hear your stories, so please share any interesting group discussions you've been part of.

Oh, yes, great topic! I have several examples.

1) Way back in college, I was hanging out with five girls in a dorm room, and one of them started talking about her bra size being a D cup with a tiny band that didn't exist, so it was hard to find bras. Some of the other girls were freaking out because I was there listening, so the topic changed to if it was okay that I was there to hear it all. Eventually, they all talked about their bra sizes, and they actually started to argue about who was wearing the right size. I was hoping that they would show each other, but that didn't happen.

2) Probably ten years ago or so, my wife's best friend and husband were at our house. Somehow I was able to joke about skinny dipping, and the husband talked about a time he went skinny dipping and how wonderful it was to see some of the women naked that he had hoped to see for years. The reaction of my wife's best friend was priceless. She didn't know about the skinny dipping and wasn't too happy that her husband had been hoping to see the women naked for such a long time. That led to her confessing to a time she went swimming in a bra and panties just before they had met. It was exciting watching them go back and forth for a half hour, mainly because my wife and I just sat there listening, and these were people who you would never, ever expect to do those things.

3) We aren't religious people, but one of our closest friends for years was a very young female pastor just starting her career. She was trying to get pregnant while my wife was already pregnant. One afternoon just after church service (we would go just to support her sometimes), she was asking my wife who she was going to let into the delivery room because our friend's mom and farther in law wanted to be in there. My wife said it was going to be just us, but our pastor friend said that she wasn't sure because she said, and I quote, "I mean he [her father in law] is going to see my vag, and I guess I don't care who sees my vag these days. It's a bit of a mess, but so are all of the other vag I have seen." This was well in earshot of a lot of other people--the pastor talking like this after church! (She was a very loud person.) Her thoughts didn't matter anyway because she had both of her kids in the car en route to the hospital each time.

4) I have a female friend who is married to a man but still very, very into women. She frequently tells me about all of her female crushes, and a lot of details about their bodies if she sees them in lockerrooms, etc. Her husband told her that she can play with any woman she wants to, but my friend tells me that she would fall in love and leave her husband and five kids behind if she were to actually get involved with a woman. On the one hand, I am flattered that I am her only friend she can trust to tell when it comes up, but on the other hand it turns me on so much when I get to know what her friend's (and some are my acquaintances) look like naked!

When we were newlyweds my wife hosted a sleepover bachelorette party her BFF who was about to get married, 3 other of their friends. I stayed as bartender and cook, I would have preferred not to be there. I was keeping them happy with margaritas, snacks and and wine, They were all getting pretty tipsy when my wife insisted I roll a joint for them, I pretty much stayed out of the room until then, but hung out for a few hits.

The bride was going on about she was looking forward to living together so they could have sex everyday, I guess I had donned the cloak of invisibility, because they were not paying attention to the fact that I was there. Two were single but had BF's, so they were talking about how often they wanted sex, what positions they liked, their orgasms. I was glad my wife was very vague.

I was getting pretty buzzed myself and I wish I remembered more.

I shared and office with 2 women once, and i think they often forgot I was there. I heard about dates, past bfs 1 night stands and strange encounters. I hear about facials, swallowing, a mfm, butt sex, ass licking, toe fucking lol.

One of the ladies was pretty much open for anything, the other (the hotter one) was actually very vanilla. But open about the things she WOULDNT do which was still hot to hear.

Did you ever hook up with any of the college dorm room women? I know it was a long time ago, but I wonder what some of the "is it ok to talk about this" dialog was. My thought is that women are either lightly flirting when they do this, or don't consider you a threat/legitimate hook-up.

Any sense where the women in #1 or woman in #4 fall (teasing or not)?

Did you and your wife ever talk about it afterward? Maybe your (and others) experience is different, but I can't remember EVER sitting around with a group of guys and going through really detailed conversations like groups of women do. I've written a little about them, but I can't imagine sitting around with a group of guy friends going through the details. It is a little exciting thinking about how much detail the women in our lives remember and share.

My fiancee is pretty open with her two girlfriends (obviously), and it makes me wonder what more she shares when I'm not around.

Did you get the sense they were really ignoring that you were there or that they liked talking in front of you? It sounds like you kept your head down and listened, but were you ever part of the conversation?

#1 They all just saw me as a "guy friend" and not a threat, plus they knew I was too scared to do anything, so they were fine talking about their bras. Three of them turned out to be lesbians within that year, the fourth transferred after the first semester, and I don't know whatever happened to the fifth. I just remember them talking about the band sizes and the bands riding up in back, how much coverage for the bra, etc. This was back when women wore bras that actually fit and weren't stiffly padded, so no talk about bra cup gaps or anything since that didn't exist back then.

#4 Is not teasing me at all. Not on purpose anyway. If she knew how much our conversations turned me on, she would probably never talk to me again. She sees me as a very, very close friend, and I don't want to break that, but I wish I could tell her how much I love hearing her stories!!

one of those low-key, off-the-wall topics... and I love it! great idea for a thread Indym!

I too was hanging poolside with 2 hot married female friends of mine late one night.. we were all buzzed and enjoying just hanging while the other spouses had called it a night and had gone to sleep... at some point the women began discussing how they trimmed their bush, which instantly perked my interest, but I maintained a low-key profile and sat and observed, not wanting to ruin a good thing... turns out these 2 ran the gamut... the hotter of the 2 wives said she keeps it shaven bare bare bare... while the other cute older mom said she feels more like a true woman and proud by keeping her bush, 'bushie' (not a jungle mind you, but trimmed around the edges and bushie)... then they started going over the merits of each one (clean, easy, sexy smooth, vs. its natural to have it be natural) while I listened... we were all buzzed enough that I thought, if I come up with the right approach and right way to phrase it, perhaps they'd be comfortable (and eager enough) to pull their bikini bottoms down for me and show me.. and I'd get to be an impartial judge... sadly I fumbled in my mind with what to say without it coming off creepy and came up with nothing... at the very least I could have said "well, let's see.. why dont you show me, and I can give you an impartial guy's honest opinion".... worst that would have happened is they would have laughed it off with a 'ya right'.. or an 'in your dreams'... but I do have it in my mind to get the hotter one who has flashed me her boobs before to show me her shaven bush someday... 'hey remember that time you told me about how you shave your bush? do you still? not sure I really believe you.. why don't you show me'

Good luck! It sounds like the one wife might be open to more... just have to find the right time and way to bring it up. Do you hang out with these couples often?

The friends I mentioned in my post are definitely teasing me, but it still feels like walking a tightrope.

Never had the luck to be involved in such a fun conversation. However, my wife has had some interesting conversations with her sister. She never tells me about what, except 1 time. That was shortly after the 1st time we all saw eachother naked at the sauna. Apparently my SIL thinks I have a rather big and nice looking dick 😁. Always fun tot hear such a thing, specially coming from SIL!

Book club
 

Years ago, my gf (now wife) and three of her friends were reading the "Shades of Grey" series as they came out and would have get togethers at our house and discuss each chapter as they finished it. I interjected here and there as I caught snippets of the conversation, but it got really interesting when they finished the first book and went on to the second.
By then, I was interested enough to pick up my wife's copy of volumn one of the series and start reading it. The women were genuinely interested in a man's view of the books and I became part of the group through the end of the series.

Many interesting conversations were had about the characters and incidents that were had in the books and included how I would have handled certain situations portrayed there. Many times the conversations got personal between the five of us, including cock size (both real and preferances), our bedroom antics and our fantasies, what kind of private grooming we liked. That's where I first heard of "manscaping", (believe it or not!) and that my future wife liked it. By the time the group broke up, everyone knew that I had gone from natural to nothing, lol. My gf had shared photos of me with the other ladies in the group, but I didn't know it at the time. Unfortunately, nothing more ever happened between the five of us, but I know the ladies enjoyed our talks as much as I did.

Outcomes
 

If a Member of the Opposite Sex informs you, without prompting, of some of their Past Sexual Adventures, what should your reaction be ? Should you regard this as a sort of "Confession", to be treated with utmost Confidence ? What should the reaction be if you decide to "gently proposition" them ? And should this reaction recognise that you are in possession of Highly Toxic Information ?

It sounds like it never got awkward. It hasn't for me, but I'd love for that conversation to start back up. I thought it might after we all went out to a couple of bars, and they were pretty relaxed after we got home, but it didn't.

Were any of the women bolder or more reserved than the others talking about details?

I suppose my relationship with the person would guide my reaction.

I'm not sure I'm following what you are asking, though.

All were pretty free with the info, but my wife-to-be and her best friend Diane were definitely the ring leaders. Between the two of them, they would open the discussions, ask the questions and goad the other two on when needed. The other two, (Sorry, I'm drawing a blank on their names right now, dammit.) would often surprise us with an observation or a story occasionally as well.
All four of them were active in asking me questions or asking for my opinions and they knew I'd be truthful because my gf would have (and did, occasionally) call me out if she thought I were less than truthful. :rolleyes:

Nothing overt but...
 

Mrs Ferg, 2 sisters (both long-time married) and me chatting over vino after dinner.

Her 2 sisters would never have a really open conversation of a sexual nature although their attitudes are far more liberal today than 40 years ago.
This was a fairly low-key conversation but believe me the tone, eye contact and body language spoke volumes.

They were generally talking about how they met their respective partners, and both SIL’s said that their respective husbands were their first ever boyfriends.
They asked me if I had previous girlfriends and I said yes.
My Mrs didn’t have to say anything but one SIL asked if it bothered me that she had boyfriends before me. I said, no, I knew she had lots (emphasised) of boyfriends before she met me but if a pretty girl like her hadn’t I would probably think there was something wrong with her.
They seemed Ok with that but I detected whiff of envy on their part.

So, roughly translated
SIL1 “I’ve only fucked one guy in my life”
SIL2 “Me too”
SIL1 Ferg have you fucked other girls before our sister
Me “Yep”
SIL1 “Ferg, does it bother you that our sister has fucked loads of other guys before you?”
Me “No, that’s cool, I would have been surprised if she hadn’t”
SIL’s thinks “Damn”