I dared my shy friend to flash me
Posted: Fri Oct 18, 2024 2:31 am
Hi everyone! I'm new here, and I've loved lurking and reading your wonderful stories. I thought I'd share one from my own life. It's very long and quite tame, but I hope you'll like it!
(If you want to skip the buildup, skip to the section called "THE PARK")
-
PRELUDE
I'm 18 years old. I'm shy, but learning to be more confident. I have a group of friends - much more confident than me. With one exception.
Millie is nerdy and quiet. She rarely speaks in a group setting, unless you ask her about her favourite fantasy novels - then she really opens up. I've developed a crush on Millie. Maybe her shyness makes her seem less intimidating, more approachable. In practice, though, I couldn't dream of approaching her romantically.
I'm the kind of guy who finds any girl attractive when I get to know her. As the months go by, Millie just seems so hot to me. Her plaited brown hair, her hippy-ish style of dress, her cute glasses. An adorable gap in her teeth, and these incredibly dark brown eyes. She always looks like she's having a lovely time, and her smile is so gorgeous that it causes me to feel pain in my heart.
Thing is, me and Millie are two members of a friend group - but we never hang out just the two of us. So I never miss a house party or group activity.
And then.
One of the gang - Chris - wants to go to a pub quiz. We all agree, but on the day, most people cancel. When we get there, it's just me, Chris ... and Millie.
Chris has never been the most organised guy, and we end up at the pub two hours before the quiz even starts. So we drink and talk, and it's the most I've been able to talk to Millie one-on-one.
I wonder if Chris sensed that I liked Millie. He lets us talk, rarely interrupting. He keeps volunteering to go to the bar. Even when it's my turn to buy drinks, Chris takes my card to the bar himself.
Has Millie noticed? I don't think so, to be honest. We're talking about her best pub quiz categories, and she's talking breathlessly about literature, movies, music - sharing cool facts and obscure trivia.
The quiz comes and goes. We come second-to-last - two hours of pre-drinking didn't help our chances. So we drink more to drown our sorrows.
Then Chris checks his phone.
"Oh," he says. "Sorry. Elinor's locked herself out of the flat."
Elinor is Chris's girlfriend, so he shoots off.
I see Millie check her watch, and I panic. Millie always leaves early - but Millie CAN'T leave early. I need to say something to keep her here.
I'm not a clever person. I'm not quick, I'm not creative. But in that moment, my brain gives me the perfect thing to say.
"Let me give you a Doctor Who quiz."
Millie's head jerks up to look at me. "Okay!"
Millie's a huge fan of Doctor Who, and I know enough to come up with some questions. I ask her about Daleks, Tom Baker, the sonic screwdriver, until I ran out of facts.
I can't tell you how amazing it feels to hold Millie's entire attention. Her beautiful smile, her sparkling eyes, responding excitedly to my questions.
"Okay," I say. "You ask ME some questions!"
"About Doctor Who?" she asks.
"Sure!" I say.
Her questions are tough, and I get most of them wrong. We laugh, and I say, "Do I have to drink every time I get one wrong?"
"Of course!" says Millie.
She asks me what year the show started. Who knows that?! She asks me who created the Daleks - and I know that one! I make her drink when I get one right.
Eventually, the pub shuts. We're both hammered and giggly.
"I have an idea!" I say. "I've thought of somewhere I want to go!"
"Where?" she asks.
"It's a surprise!" I say.
But that's a lie. The truth is, I don't know where I want to go. I just know I want Millie to stay out with me a little longer.
So I lead the way, and we wander around, until I find somewhere interesting to hang out.
-
THE PARK
The park isn't very big. It's got a children's play area, a single basketball court, a single path from one end to the other - and a wooden bench.
I lead Millie to the bench, and we sit.
I expect her to be confused or annoyed. Why are we in a park? But she doesn't say anything. She just looks at me expectantly.
So I know I have to say something. This is what my brain gives me:
"Okay, Millie. Truth or dare?"
I have never played truth or dare in my life. I was never invited to those kinds of parties. But for some reason, it seems like the perfect thing to say.
Again, I'm half-expecting Millie to look at me like I'm an idiot. Why on earth would she play truth or dare in a small park in the middle of the night?
Instead, she says:
"Ooooh! Okay. Truth."
"Okay. What is the name of the first person you fancied?"
Millie blushes! I've never seen her look embarrassed before.
"Mike," she says. Not my name, but I didn't think it would be.
"Your turn," I say.
"Oh!" she says. "Truth or dare?"
"Truth." Let's match her picks for now.
She asks me the same question, and I answer, "Beth". It's the truth.
Next, she asks for a dare. I think, let's not go too crazy too soon. I dare her to do five star jumps, which she does. I choose a dare, and she gives me five press-ups in return.
And for a while, this continues. We choose truths and dares, and both are mild. But it's hard to keep thinking of dares.
"Dare," she says.
"Okay," I say. And - trying to sound as casual as possible - I say, "Okay! I dare you to flash me."
I see a super quick expression of shock on her face, but she quickly controls herself.
"Alright, I'll flash you," she says.
She says the words so quickly, like she's been flooded with adrenaline. I can almost hear her heartbeat increase. And I cannot BELIEVE what she's just said. She WILL flash me?! I've never seen anyone naked before, and my crush has told me she's willing to flash me. My own body floods with adrenaline.
"But," she says. "When you say 'flash', do you mean with bra or without? I'll do it either way. I'm just checking."
Whenever I think back on this night, this is the moment that excites me the most. This beautiful girl, giving me the power to decide whether or not I want to see her bare tits. For a shy virgin, what could be more miraculous?
I savour the moment. I pretend I'm thinking it over.
"Let's go with no bra," I say. My heart is in my throat.
"Okay!"
Millie looks around the park. It's well-lit by harsh floodlights, and there's no-one around. There are houses in the distance, but probably far enough away that no-one would see anything. Probably.
So Millie pulls her top up to her neck, revealing her plain white bra. Then she hooks her fingers under the bra, and lifts it.
Nothing in my life will ever compare to this moment. Her small, pale breasts, illuminated by the stark lighting of the park. Her eyes are scrunched closed, like she can't look at me seeing her boobs like this. Her nipples are small, pink, and textured. They're longer than I expected. It feels so surreal to see them! My friend Millie's actual boobs. My friend letting me see them in crystal clarity, simply because I dared her.
I've seen breasts in porn, but there is NOTHING like seeing the real-life tits of your friend, shown to YOU because she trusts you.
She pulls her top back down, and cackles with laughter. Her breathing is shallow, like she's just finished a sprint. The laughter's contagious, and I join in. "That was amazing!" I say.
"Okay, okay, okay," she says, controlling her breathing. "Truth or dare."
Oh, yeah. Gulp.
"Dare."
"Okay," she says. "I dare you to flash me."
I'm so nervous.
"Are you sure?" I say.
"Only if you want to," she says.
"I chose dare!" I say, and stand up. I brace myself, and reach for the button on my trousers.
Suddenly, Millie changes her mind.
"Okay, actually - I dare you to moon me," she says.
So I turn around, take a deep breath - and pull down my trousers and pants.
I'm glad she can't see me blushing. Even though it's just my bum, I feel so vulnerable. My friend seeing my bum, and me not being able to see her face. After a few seconds, I pull my trousers back up.
"Truth or dare?"
This time, Millie picks truth. I ask her when she had her first kiss. She was 17. Last year! Before we'd met. I pick truth as well, and then Millie chooses dare again.
I don't want to scare her, so I give her a milder dare, but eventually I'm brave enough to dare her to moon me back.
Looking a little braver now, Millie stands. Turns around. And pulls her pants down.
Her bum is slim, with a shorter crack than I'd seen before. Millie's trousers are low enough for me to see the shape of her entire bum - the base of her cheeks. With her back to me, she can't see how greedily I'm staring, enjoying every last detail. The dimples above her cheeks, the surface covered in goose bumps because of the cold air. I'm fascinated by the tiny, almost-invisible hairs across the skin.
Millie pulls her trousers back up, spins around, and sits down - with incredible speed. She seems manic all of a sudden.
"Oh my God!" she says. "I can't believe I did that!"
It's so interesting to me that mooning made her freak out more than flashing her chest. She's still laughing, but she keeps reiterating the point.
"I can't believe I showed you my bum!"
"A dare's a dare," I say.
"And I showed you my boobs!"
"Are you okay?" I ask. I'm worried I've pushed her beyond her comfort zone.
"I'm fine," she says. "I just can't believe I did this. I've never flashed anyone before."
"I've never mooned anyone either," I say.
"You've seen my boobs!"
Millie giggles again. Maybe the drinking finally caught up with her. Maybe it was the craziness of the game. Either way, I decided to walk her home, and bring an end to the night.
(If you want to skip the buildup, skip to the section called "THE PARK")
-
PRELUDE
I'm 18 years old. I'm shy, but learning to be more confident. I have a group of friends - much more confident than me. With one exception.
Millie is nerdy and quiet. She rarely speaks in a group setting, unless you ask her about her favourite fantasy novels - then she really opens up. I've developed a crush on Millie. Maybe her shyness makes her seem less intimidating, more approachable. In practice, though, I couldn't dream of approaching her romantically.
I'm the kind of guy who finds any girl attractive when I get to know her. As the months go by, Millie just seems so hot to me. Her plaited brown hair, her hippy-ish style of dress, her cute glasses. An adorable gap in her teeth, and these incredibly dark brown eyes. She always looks like she's having a lovely time, and her smile is so gorgeous that it causes me to feel pain in my heart.
Thing is, me and Millie are two members of a friend group - but we never hang out just the two of us. So I never miss a house party or group activity.
And then.
One of the gang - Chris - wants to go to a pub quiz. We all agree, but on the day, most people cancel. When we get there, it's just me, Chris ... and Millie.
Chris has never been the most organised guy, and we end up at the pub two hours before the quiz even starts. So we drink and talk, and it's the most I've been able to talk to Millie one-on-one.
I wonder if Chris sensed that I liked Millie. He lets us talk, rarely interrupting. He keeps volunteering to go to the bar. Even when it's my turn to buy drinks, Chris takes my card to the bar himself.
Has Millie noticed? I don't think so, to be honest. We're talking about her best pub quiz categories, and she's talking breathlessly about literature, movies, music - sharing cool facts and obscure trivia.
The quiz comes and goes. We come second-to-last - two hours of pre-drinking didn't help our chances. So we drink more to drown our sorrows.
Then Chris checks his phone.
"Oh," he says. "Sorry. Elinor's locked herself out of the flat."
Elinor is Chris's girlfriend, so he shoots off.
I see Millie check her watch, and I panic. Millie always leaves early - but Millie CAN'T leave early. I need to say something to keep her here.
I'm not a clever person. I'm not quick, I'm not creative. But in that moment, my brain gives me the perfect thing to say.
"Let me give you a Doctor Who quiz."
Millie's head jerks up to look at me. "Okay!"
Millie's a huge fan of Doctor Who, and I know enough to come up with some questions. I ask her about Daleks, Tom Baker, the sonic screwdriver, until I ran out of facts.
I can't tell you how amazing it feels to hold Millie's entire attention. Her beautiful smile, her sparkling eyes, responding excitedly to my questions.
"Okay," I say. "You ask ME some questions!"
"About Doctor Who?" she asks.
"Sure!" I say.
Her questions are tough, and I get most of them wrong. We laugh, and I say, "Do I have to drink every time I get one wrong?"
"Of course!" says Millie.
She asks me what year the show started. Who knows that?! She asks me who created the Daleks - and I know that one! I make her drink when I get one right.
Eventually, the pub shuts. We're both hammered and giggly.
"I have an idea!" I say. "I've thought of somewhere I want to go!"
"Where?" she asks.
"It's a surprise!" I say.
But that's a lie. The truth is, I don't know where I want to go. I just know I want Millie to stay out with me a little longer.
So I lead the way, and we wander around, until I find somewhere interesting to hang out.
-
THE PARK
The park isn't very big. It's got a children's play area, a single basketball court, a single path from one end to the other - and a wooden bench.
I lead Millie to the bench, and we sit.
I expect her to be confused or annoyed. Why are we in a park? But she doesn't say anything. She just looks at me expectantly.
So I know I have to say something. This is what my brain gives me:
"Okay, Millie. Truth or dare?"
I have never played truth or dare in my life. I was never invited to those kinds of parties. But for some reason, it seems like the perfect thing to say.
Again, I'm half-expecting Millie to look at me like I'm an idiot. Why on earth would she play truth or dare in a small park in the middle of the night?
Instead, she says:
"Ooooh! Okay. Truth."
"Okay. What is the name of the first person you fancied?"
Millie blushes! I've never seen her look embarrassed before.
"Mike," she says. Not my name, but I didn't think it would be.
"Your turn," I say.
"Oh!" she says. "Truth or dare?"
"Truth." Let's match her picks for now.
She asks me the same question, and I answer, "Beth". It's the truth.
Next, she asks for a dare. I think, let's not go too crazy too soon. I dare her to do five star jumps, which she does. I choose a dare, and she gives me five press-ups in return.
And for a while, this continues. We choose truths and dares, and both are mild. But it's hard to keep thinking of dares.
"Dare," she says.
"Okay," I say. And - trying to sound as casual as possible - I say, "Okay! I dare you to flash me."
I see a super quick expression of shock on her face, but she quickly controls herself.
"Alright, I'll flash you," she says.
She says the words so quickly, like she's been flooded with adrenaline. I can almost hear her heartbeat increase. And I cannot BELIEVE what she's just said. She WILL flash me?! I've never seen anyone naked before, and my crush has told me she's willing to flash me. My own body floods with adrenaline.
"But," she says. "When you say 'flash', do you mean with bra or without? I'll do it either way. I'm just checking."
Whenever I think back on this night, this is the moment that excites me the most. This beautiful girl, giving me the power to decide whether or not I want to see her bare tits. For a shy virgin, what could be more miraculous?
I savour the moment. I pretend I'm thinking it over.
"Let's go with no bra," I say. My heart is in my throat.
"Okay!"
Millie looks around the park. It's well-lit by harsh floodlights, and there's no-one around. There are houses in the distance, but probably far enough away that no-one would see anything. Probably.
So Millie pulls her top up to her neck, revealing her plain white bra. Then she hooks her fingers under the bra, and lifts it.
Nothing in my life will ever compare to this moment. Her small, pale breasts, illuminated by the stark lighting of the park. Her eyes are scrunched closed, like she can't look at me seeing her boobs like this. Her nipples are small, pink, and textured. They're longer than I expected. It feels so surreal to see them! My friend Millie's actual boobs. My friend letting me see them in crystal clarity, simply because I dared her.
I've seen breasts in porn, but there is NOTHING like seeing the real-life tits of your friend, shown to YOU because she trusts you.
She pulls her top back down, and cackles with laughter. Her breathing is shallow, like she's just finished a sprint. The laughter's contagious, and I join in. "That was amazing!" I say.
"Okay, okay, okay," she says, controlling her breathing. "Truth or dare."
Oh, yeah. Gulp.
"Dare."
"Okay," she says. "I dare you to flash me."
I'm so nervous.
"Are you sure?" I say.
"Only if you want to," she says.
"I chose dare!" I say, and stand up. I brace myself, and reach for the button on my trousers.
Suddenly, Millie changes her mind.
"Okay, actually - I dare you to moon me," she says.
So I turn around, take a deep breath - and pull down my trousers and pants.
I'm glad she can't see me blushing. Even though it's just my bum, I feel so vulnerable. My friend seeing my bum, and me not being able to see her face. After a few seconds, I pull my trousers back up.
"Truth or dare?"
This time, Millie picks truth. I ask her when she had her first kiss. She was 17. Last year! Before we'd met. I pick truth as well, and then Millie chooses dare again.
I don't want to scare her, so I give her a milder dare, but eventually I'm brave enough to dare her to moon me back.
Looking a little braver now, Millie stands. Turns around. And pulls her pants down.
Her bum is slim, with a shorter crack than I'd seen before. Millie's trousers are low enough for me to see the shape of her entire bum - the base of her cheeks. With her back to me, she can't see how greedily I'm staring, enjoying every last detail. The dimples above her cheeks, the surface covered in goose bumps because of the cold air. I'm fascinated by the tiny, almost-invisible hairs across the skin.
Millie pulls her trousers back up, spins around, and sits down - with incredible speed. She seems manic all of a sudden.
"Oh my God!" she says. "I can't believe I did that!"
It's so interesting to me that mooning made her freak out more than flashing her chest. She's still laughing, but she keeps reiterating the point.
"I can't believe I showed you my bum!"
"A dare's a dare," I say.
"And I showed you my boobs!"
"Are you okay?" I ask. I'm worried I've pushed her beyond her comfort zone.
"I'm fine," she says. "I just can't believe I did this. I've never flashed anyone before."
"I've never mooned anyone either," I say.
"You've seen my boobs!"
Millie giggles again. Maybe the drinking finally caught up with her. Maybe it was the craziness of the game. Either way, I decided to walk her home, and bring an end to the night.
