My wife's best friend is a cute blonde that I have had a thing for since we’ve met. Heather and I have flirted back and forth for years (well, more so me flirting to her more than her back, but she flirts back just enough to keep me going.)

In the past we have chatted online about when she and my wife lived together. She would hint they have played naked a little bit but would never admit it. Jenny, my wife, would tease me with those thoughts once in a while too. I’m sure they never did because both are very conservative especially when it comes to sexual things. I have begged and asked for pictures for years but never got anywhere. I did learn that Heather wore a 34D bra and she didn’t shave her bikini area.

One day I was home alone, Jenny was working and Heather sent me an IM:

“Hey there.”

“Hi, how’s it going?”

“Great and you?”

“I’m well. What are you up to?”

“I just took some pictures.”

“Cool, of what?”

“Well, they are for Jim.”

“Oh really, and why are you telling me?”

“Don’t you want to see one?”

“Of course I do.”

She sent me a picture of her in her bedroom wearing only a black bra and cream colored panties.

“Wow, you look great!”

I took of my shirt off and took a picture and sent it off, I hoped she would notice my bulging jeans.

“Nice!”

She took another picture. This time she was closer to the camera.

“What do I need to do to get you out of your bra?”

“Let’s see what you have to offer.”

My heart raced. I felt a little cold sweat developing and my cock was rock hard. I striped down to my boxers, my cock was making them bulge out. I set up the camera and timer, five seconds later it flashed. I dropped my boxers, five more seconds it flashed again.

I loaded the pictures to the computer and I sent the boxer picture.

“Nice bulge. What has you so excited?”

“Umm, you do. I have been waiting a long time to see you like this.”

“Oh really? And how are you expecting to see me?”

With that response she sent me another picture.

She had a big smile on her face (the last couple she was expressionless) and no bra. I could see her nipples were erect.

“Wow, Heather you look amazing! Thank you for sharing this with me. I've got another for you.”

“Send it Kevin, I want to see what you have be hiding!”

I sent my nude picture. I know I had a big smile too. I waited and waited for a response. Then I saw a file to accept. It was of her standing there with a smirk on her face and fully naked. Her breasts are so full and her blonde pussy was wet.

“Kevin, that is so much bigger than I expected! That’s huge! How big is it? Jim has nothing on you.”

"It’s not huge, maybe a little bigger than average. It’s 8”. And fully hard now that I see you naked. I have waited so long for this day. You look amazing”

“Thanks. You can’t tell Jim about this.”

“No need to worry about that, Jenny doesn’t need to know either”

“Are you touching that monster?”

“Yes, are you touching yourself?”

“I have my finger inside, I’m really wet.”

“You should use at least two fingers, I’m thicker than that.”

“Yes, you are. You would hurt me.”

“No, I would go really slow and make sure you are very wet. I’d love to slide my tongue inside you.”

“You know we can never do anything about this. Mmmm, this feels so good.”

“I know but it is fun to think about. We would have lot of fun. No need to tell anyone. Keep playing I want you to have an orgasm.”

“Oh, I will don’t you worry.”

“This feels so good. How bad do you want me to have an orgasm?”

“If I was there with you, it would be my first priority.”

“Mmmmmm, yesssss... ooooh... mmmm.”

“Did you just do it?”

“Yes and I should get going. Thanks for sharing with me Kevin. I hope you had as much fun as I did. Naked hug.”

 The load I blew when she left was huge.

I have sent her a few more pictures since but she hasn’t sent me any. We never talk about it at parties or anything but I still have the hope that something will happen in the future.