A Bachelorette Dilemma

My phone buzzed. It was a message from Chloe, Sarah's maid of honor and one of her oldest friends. My heart gave a little flutter, I didn't normally receive messages from Chloe..

"Hey Will!" It began, followed by a string of emojis that seemed a little too enthusiastic for something simple...

Instead, it read: "The time has come for me to ask for a big favour from you for Sarah's bachelorette party, which btw goes without saying needs to be kept a surprise. We're planning a 'pin the willy on Will' game, and we are requesting a tasteful nude of you that we can print! It can have as much or as little nudity as you're comfortable with. Just anything would be great as we know Sarah will love the surprise!" 

I blinked. Then reread the message. And then reread it again. My dick twitched. A nude photo of me? For a game?  In front of all of Sarah's friends?

I chuckled, picturing Chloe's mischievous grin. This was exactly the kind of playful, slightly outrageous thing Sarah's friends would come up with.

I typed a reply, then deleted it. "Are you serious?" seemed too dull. "You want what?!" felt too dramatic and prudish.

I paced around the house, a playful internal debate unfolding. I knew Sarah's friends well; they were fun-loving, trustworthy and wouldn't intentionally make me uncomfortable. But the line was blurry. I thought about the various levels of "as much or as little nudity" I could send. A photo from the waist up? A strategically placed object obscuring my dick? Or was it that being nude was the baseline and how much nudity I was comfortable with actually meant a sliding scale of flacid to a full on raging hard on?  

I decided I needed to test the waters on her 'as little or as much nudity' comment and hope she made it clearer for me:  

"Hey Chloe! ahah what a request, but of course I'll help you in making Sarah's bachelorette as much fun as possible. So I have a photo in mind that would be good for your game, but I'm not sure whether you really want the full nude version!"

Balls now in your court Chloe - she messaged back quickly:  

"I mean it's entirely up to you, but i'm sure Sarah would have no issues with that at all haha"

She then followed up with another message:

"I can always make you a modesty leaf"

The "modesty leaf" comment made my dick twitch again. But the core request remained. Did she genuinely want a fully nude photo, trusting my judgment on "as much or as little nudity," or was this a test of my loyalty to Sarah, with the expectation that I'd play it safe? Or did the fact she say "modesty leaf" imply that she truly was expecting me to send her a photo of me with my dick on show.

Her comment about Sarah having no issues was true and I knew Sarah would find it funny cock on show or not. Back when we were dating I knew she enjoyed tipsily showing Chloe and a few others naked photos of me even with a full on erection. I still found it a turn on knowing that her friends had seen my cock and I wonder if that was why Chloe seemed so casual about me sending one now.  

But it was different now right? I was about to get married and those times were a few years ago. I was torn between the genuine turn on of sending Chloe a nude photo of me and the thought of all her friends seeing it too.

But the other side was If I might actually just embarrass myself if her friends thought it was too much especially as some of Sarah's other friends attending the bachelorette perhaps didn't have the same relationship I had with Chloe and Sarah's core group. Some of the group were girlfriends of my best mates and I thought that could be awkward if on the bachelorette they were all playing a game of stick the willy on a photo of my actual hard cock.

The fact I was sending it to Chloe helped though, I trusted her a lot, and she also had been single for a while so I felt it wouldn't be awkward in front of a potential boyfriend of hers if he found out I'd been sending nudes to her.  

I wanted to be a good sport and the thought of doing it made my dick as rock hard as the photo I wanted to send, but I also wanted to maintain a certain decorum.

Would it be too much if I sent a nude with my erect cock on display to all Sarah's friends? Or would it be too boring if I sent Chloe the nude but with a modesty leaf already fashioned?

I decided to test Chloe again before making my decision by responding to her comment about the modesty leaf:

"Yeh perhaps I'll make you a modesty leaf to save exposing you to that!" I replied leaving it open for her.

"Haha yeah I'm not sure what some of the other girls are on the bachelorette are like"

Chloe's reply seemed to indicate what I thought - that she would find it funny with a photo of me fully naked - but the big question was: If I sent her one with a full raging erection whether that was what she was hoping and expected? Or would I completely miss the mark and just be reeling in the embarrassment of having sent Sarah's maid of honour such an erotic photo months before my wedding day?  

Part 2 coming soon.. Let me know what you would do?