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Normally, I wouldn’t be caught dead in something like this, but last year, there was a bachelorette party that I attended with Angela, and she forced the outfit upon me.

I don ruby-red lipstick and fuck-me eyeliner, then pose for a couple of sexy pictures in front of my full-length mirror.

Girls do this all the time,I reason with myself.

Yeah, teenage girls.

I’ve never craved attention, which makes this awkward. Sure, I like to look nice, and I enjoy it when men admire me, but I don’t want to look like I’m screaming, “Look at me!”

But that’s the point. You want Weston to look at you.

I enter my text box, insert the pictures, and type:

Jenna:Decided to go on that date with Barry. How do I look?

Weston:Like you’re going to give him a heart attack.

Jenna:Rosie Jetson would never do that…or at least she’d have a built-in defibrillator.

Weston:Seriously, what’s up? Did you wanna have Stage Two tonight? Because I can make that happen.

Jenna:No. I’ve just decided that I needed help in other areas.

Weston:Like dressing for dates? Is that seriously an outfit you would consider?

Jenna:OMG—no! I just realized that I’ve never sent a sexy pic before.

Weston:never?

Jenna:I’ve never been comfortable enough to. I usually only make it 3 - 5 dates before I’m dumped.

Weston:On behalf of the male gender, I apologize for just how stupid we are. (but secretly, I’m doing a happy dance)

Jenna:You wanna know what else I haven’t done before…

Weston:Honestly, I don’t know if I can handle it. Looking at that pic you sent me…wow! I mean—WOW! You could moonlight as a stripper with a body like that.

Jenna:thanks…I think…

Weston:so, what is it you’ve never done?

Deep breath. Deep breath. He’s here to help. You got this.

Jenna:sexted

Weston

It’s been years since I’ve had a schoolboy crush. Actually, I don’t think I’ve ever really had one. I was always bogged down with real-world worries in my youth, and when I finally made it and didn’t have to keep looking over my shoulder to make sure the rent was paid, I was already a man grown. I bypassed that stage of development.

But damn if Jenna doesn’t make me feel like I have one. And holy hell—I like it.

It can’t be real. Not with how long we’ve known each other. This is probably all just a fun learning experience for her. I know she enjoyed herself the other day, and there’s not a doubt in my mind that she’s looking forward to tomorrow night. Who knows, maybe this could be some kind of friends with benefits thing if it all goes well.

Weston:The conversation usually starts with the man asking, “What are you wearing?”, but you’ve covered that.

Jenna:Well, then…what are you wearing?

I’d hate to disappoint her by saying jeans and a tee-shirt, so I quickly shed my shirt and jeans, situate myself on my couch, and take a shot of my torso, extending to include half my boxers, the bulge of my cock clearly visible in the bottom half of the photo.