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My (M45) Cheating Story - Ch. 26 ... Shy Diane!  
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longstoryshort-79 is a male
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As I mentioned ... 2015 was off to a great start ... the Crazy Hot Young Chick was still bouncing on and off my cock, I was still seeing Sad Face (before she left me for Fifty Shades of Gray) and Gusher would stop ignoring me and request a get-together every few weeks. And now Old Country Buffet was on the menu (last food pun - I swear!).

Sometime in March, Shy Diane had answered my ad about “Hiding in plain sight”. How fitting.

It turns out that she wasn't married, she just loved fucking married guys! She said that no one knew about her escapades and none of her friends would ever guess her preferences.

She was very shy and guarded (hence the moniker), but she told me that she knew immediately that she wanted to fuck me after reading my ad. We exchanged a few more emails, met up three days later. I wasn't totally crazy about how she looked in her photos, she also reminded me of an ex from college. Plus, there was no connection. I didn't know anything about her and she hardly had anything other than one word answers to say about anything. But I decided to go for it anyway.

We met up before work, I actually had to get the room the night before to make it all work out. It turned to be an awesome meetup! It turns out that she was actually WAY better looking in person! Short, petite with HUGE fake tits! My first experience with fake breasts!

I didn't expect much conversation and Shy Diane didn't disappoint. We basically got to it right away. She showed up in her work dress, so she asked if we could get undressed right away because she didn't want to take a chance of it getting wrinkled or stained!

Sure! We both undressed ourselves and met back in the middle of the bed. She was a great kisser, quiet, shy little moans as I kissed down her body. Her pussy was extremely wet and very tight ... freshly waxed! Although she was shy, she spoke up to tell me that she didn't want to cum from oral. So I moved up and we started to fuck. She came a bunch, was able to pop my cock out of her when she orgasmed! We only fucked once, in multiple positions. When she finally had enough, she asked me what position I'd like to finish in. I choose doggie, but I kept going too deep for her, so we slid down and into lazy doggie (prone bone). My new favorite! It didn't take me long to finish ... she requested that I pull out and cum on her back. I hadn't noticed it before I came, but she had some lovely butterflies sauntering around a quiet field tattooed on her lower back that made the perfect target.

She kissed me, thanked me for a good time, got up and rinsed off in the shower and put her dress back on and left. She had to be to work by nine.

Great experience with Shy Diane, but unfortunately it was a one time thing. She just stopped answering my emails. I didn't put much effort into another meetup because around that time is when I met The Pearl Necklace!

My (M45) Cheating Story - Ch. 27 ... The Pearl Necklace! Stay Tuned!

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1 month ago