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My (M45) Cheating Story - Ch. 24 ... Big Janice!
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longstoryshort-79 is a male
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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. As far as new meetups; Big Janice, Old Country Buffet, Shy Diane, Cake Eater and Darla (I can hardly remember her, no wonder she didn't even get a fun moniker!).

Big Janice started 2015 off with a bang! She answered my ad titled "Perfectly Bad", turns out her and her husband were pretty reserved and her New Years Resolution was that she wanted to try something new. We chatted for a few weeks before we decided to meet. To break the ice, we made a bet on who would win the Super Bowl. I won. She got the room, I got the condoms and beer.

We set up the date for after work, we emailed throughout the day. I thought for sure she was going to chicken out last minute, but lo and behold she emailed saying she got the room. Yes! ... but ... she wanted to meet at the bar across the street for a drink first. Oh!

The drink went fine. Our banter was the same as it had been over email. No problem there ... the only problem is SHE WAS BIG! At least six feet tall ... not fat at all ... just big. I thought back to the Tall Runner and remembered how fun she was ... and thought WTF ... why not ... after our drink she told me the room number, asked me to give her a ten minute head start.

With the head start, I was imagining that she was going to get into something sexy, have the atmosphere heated up with some low lighting and music ... instead, the door was open when I arrived and she was (fully clothed - jacket still on) sitting on the edge of the bad. Shit!

She asked me to sit down and said I was a nice guy, even better looking in person, but she just didn't have any attraction to me. Awkward! I'd basically just thought the same thing about her. But had convinced myself to give her a try and now I was horny! Really horny! One last try!

"Look ... you already paid for the room and your goal for the new year was to try something new and exciting. It would be a shame if we didn't at least kiss once. If it's a no-go after that, I'll put my coat back on and leave right away."

She agreed! And we kissed. And kissed. And kissed. I finally got her jacket off and laid her on the bed and we kissed some more. She was a really good kisser and seemed to enjoy my technique as well. I eventually kissed my was down her neck, worked my hands under her shirt and felt her tits. HUGE. Super firm. Small hard nipples. I had to suck on them. This drove her CRAZY! We eventually got out of our clothes, she had a really nice body, I could tell that she was an athlete prior to kids.

I kissed my way down and down and brought her two orgasms with my fingers and tongue. Her pussy was delicious with a nice landing strip and no hair whatsoever around her lips. She was really tight, I could barely get two fingers into her. When I tried playing with her asshole she asked me to stop. So much for her trying something new in 2015!

She didn't show much interest in playing with me, so the rubber went on and we started in the missionary position and that's where we ended. She showed no interest in trying any other positions and finally asked me if I was getting close, because she was getting sore. It turns out her husband was hung like a horse, but not as girthy. And he never was able to fuck for more than a few minutes.

I finished. Got up to clean up, use the bathroom and dispose of the condom. When I got back she was dressed. Jacket on. She hugged me, said she had to go that she felt vulnerable naked and had to get dressed! Told me to take my time and lock up when I was done. She asked me not to vandalize the room or anything like that. Awkward ending to Awkward start!

And that kids, was the last time I heard from Big Janice.

My (M45) Cheating Story - Ch. 25 ... Old Country Buffet! Stay Tuned!

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Profile updated: 1 week ago

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1 week ago