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#1
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Hi all. I tried to revive the Would You Rather thread but I’ll be damned if the original didn’t cover nearly everything I can think of. If someone would like to take that over or start a new one, feel free.
However, while trying to come up with new prompts, I kept thinking of more open ended questions. Some questions that may not be suited for an entire thread of their own. So I’d like to use those here. I’ll post one every few days depending on engagement. We’ll start with some basics to get the ball rolling. Question #1 Who is the one person in your life you would most like to see naked? Obviously someone you have not already seen naked. What do they look like? How do you know them? For me it’s simple. My wife and I are best friends with a couple named Sam and Liz. I’ve posted of our experiences with them before, especially in the Low Key Events thread. She is slender and fit. Brunette with decent sized tits. Thick thighs and a nice bubble butt. I’ve seen her in bikinis loads of times but I’d love to see her fully naked. There are dozens of women’s in my life that I’d be thrilled to see in the buff, but Liz is definitely my number one. |
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#2
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The new girl in our office. Early 20s. And blonde. She works out so her body is tight. Strong legs and an arse you can bounce coins off. And she wears tight dresses and leggings to work. Very distracting.
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#3
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Jen goes to our church and is friends with my wife, and me to a lesser extent. She is a bit crazy and is decidedly challenging to get along with. Also seems to be permanently single after being married a few times. I suspect she takes a lover every now and again but nothing steady.
I've always admired her ass - she was horse rider in the past but is still an avid walker. I just recently realized that she's hiding what looks like an epic set of tits under her baggy shirts. Would love to see her sans clothing to confirm both the ass and tits. But I surely do not want to poke the crazy! ![]() Last edited by SlyBry2010; 06-23-2025 at 02:31 AM. |
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#4
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Co-worker; Indian woman but looks like Salma Hayek. Mid-fifties but body looks 30. About 5 feet, and probably around 110 lbs.
I've seen her at the gym wearing shorts and a tank top. I had a hard time looking away, and I think she noticed it. We have a "casual flirty" relationship. I'd like to think that we'd both agree that if we weren't both married, we'd be smashing. |
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#5
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My wife’s longtime bff. Which maybe is cheating because technically my wife has a few photos in a box where the two of them took topless pics of each other when they were 19 at a private pool. Thing is it’s a hard copy and while I’m grateful for it it’s not the clearest photo. Besides, while she has lovely b cup tits, what really drives me crazy is her ass and wide hips. She wears yoga pants early every day but even in jeans she’s got a top shelf ass. I’d love to see what she’s working with in the rear end department and learn if she shaves her pussy or not.
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#6
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Also an easy answer for me. My sister in law I’ve mentioned in a few posts before. She is a couple years older than my wife. They look a lot alike but my wife is 5’7 and the sister is maybe 5’2. And where my wife is a C cup, the sister is D or maybe DD. I’ve seen her in bikinis and bra and panties once and numerous down blouses and a few up skirt situations.
Just a side note, Lisa has 2 other older sisters as well and it’s been funny listening to the 4 of them talk about their boobs. My mother in law also had large boobs but only the one sister inherited them from her. |
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#7
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Only 1?
That would not do just to all the others I would love to see naked. But from all the ones I would love to see naked, there is only a handfull I would actually like to play with. And having seen my sister in law naked many times at the sauna, I can tell you it is fun comparing body shapes and size of siblings ![]() So good luck to the ones who have SIL on their list.
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Private messages are always welcome 🙂 |
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#8
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It’s very hot that many of the guys have SIL on the list. I do too.
I’ve seen the one SIL, my wife’s sister. I agree with the above poster who says comparing siblings is incredible. Seeing breasts, pubic hair, asses, and labia. Better than you can imagine. N The SIL, I want to see is my wife’s brother’s wife. She’s slender, with smaller tits (B I’d judge) and a tight little ass that looks so good in jeans and shorts. I dream about seeing her bare tits and her pussy. I can imagine the color of her pubic hair, if she keeps it. I’d love to see if she does. |
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#9
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She does not work for me directly but we do interact regularly In The office both work related and just friendly banter.
She is about 30, married, very much “girl next door” type. Shoulder length blonde hair - great Perky B cup tits still pointing forward. Killer smile and personality. She changes up her look daily from the summer fun ponytailed sundress to a tight pair of jeans with button up dress shirt, glasses, hair down and make up. Dress slacks and satin blouse hair pulled up on top and all business like. Not near enough short skirts yet but summer has only just arrived… She is a sweetheart half my age and married so my days of a quicky that no one ever knows about are long gone for me- but had I been myself at 30-40 I am pretty sure it would have ended up there…. Now I’d be uncle Pervie if I even tried… Have seen her lovely pail nipples once or twice as she leans over a box of files we are discussing or at my desk. |
#10
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Question #2
Similarly, who is the one woman you DID get to see naked in real life that you are most happy to have seen? Was it in person? Pictures? What was the circumstance? There’s been quite a few in real life instances of skinny dipping, drinking games that led to nudity, etc. all fond memories. But with pictures, you can revisit them. Analyze them. I worked at a restaurant with a girl who did pinup modeling and car shows. She wasn’t the prettiest gal but she had a lovely figure. Perfect for pinup. Even under her apron you could sense the sway of her massive tits. She’d wear these plaid pants to work that hugged her ass tightly and her butt was a perfect heart shape. I always found myself checking her out. I recall one conversation she had where she said that having a pinup persona makes posing naked easier because it’s not you doing it it’s your persona. I eventually ended up on her instagram modeling page. There were some bikini photos and I saw one that tagged the photographer. I went to their website and clicked on “client photos”. That led me to a search bar to enter your name if you were a client. I recall all this vividly because this is how I access these photos to this day. I entered my coworkers last name and there were several galleries. This was for clients to click on and order hard copies. About a half dozen have no preview picture. So when I saw these a lump formed in my throat. Are these the NSFW ones? I clicked and was prompted with “enter password HINT: last name”. Well luckily I knew her last name. And immediately got access. There were two sets of real interest. One in a leather bra and thong combo. Lots of posing with her big round ass on display and huge tits spilling out of her bra. The other is the best. She’s got a see through slip top and see through panties. There are dozens of photos that show her big bare tits in detail, just slightly obscured by the sheer top. But you see their shape, their hang, her nipples and areola. Like I said I’ve seen many women naked but these I can go back to so they win out. |
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