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This was a weird one, my fiancé Kaylee had been sleeping with other guys for a few years at this point. She was on the apps, and when she felt she wanted to try something/someone new she would swipe.
She had matched with a guy named Joel & they had started talking. Right away she knew he was weird. Right away asking about future relationship possibilities, but also divulging a lot of information about his own shortcomings.
He had mentioned that he’d only slept with one girl before, that he had tried to pay online girls to sleep with him and it hasn’t worked, and that he was willing to pay for nude photos.
My fiancé was laughing about it while telling me about him. My fiancé ended up giving him her venmo and he sent her $50. She received the money while sitting beside me on the couch, she accepted the money and went to the bathroom to take some photos. She sent him pictures in her bra, pictures of her ass in a thong, and some completely nude with full breast & ass on display.
It wasn’t much of a turn on for me, but she found it kind of endearing. Eventually after sending her some more money, he started begging her to come over to his place. My fiancé wasn’t thrilled because he had average looks, average body and an average dick. She told him she would think about coming over on the weekend.
She had talked to me about it and I told her to do whatever she wanted. She ended up telling him she would.
Kaylee(my fiancé) told me she felt bad for him and wanted to try something new. Eventually the weekend came and she went over to his place. She arrived in a skimpy tank top and Lululemon leggings.
He took her immediately to his bedroom, which she said was dark. He wanted to cuddle and talk which annoyed Kaylee. But she just started playing with his dick anyways.
While laying in bed he tried talking to Kaylee about starting a relationship, but obviously she wasn’t interested. To speed things up, she got on top of him and took his pants off. Starting giving him a sloppy blowjob.
She then took her tank top and bra off giving him his first look at her big tits. She said she laid down after giving him a blowjob and he sucked on her tits and licked her stomach for a long time.
She told him to put a condom on and fuck her. So he did, in missionary. They started to have sex and then stopped. He came within 15 seconds. Kaylee couldn’t believe it.
He apologized and Kaylee got dressed and told him that she needed to get home as it was getting late.
Standing beside his bed as she grabbed her things, he told her to wait. He reached inside his bedside table, grabbed a wad of cash and shoved it down her shirt.
Kaylee wasn’t expecting that, so in a confused state said thank you, gave him a kiss and drove back to our place.
Once home she realized he had gave her $300 and she thought it was hilarious. She said he was one her worst fucks she’s ever had and only gave him a blowjob for less that 5 minutes but her boobs were sore because of how hard he sucked on them.