When he switched off the car, Mary was giving him a look that he could have enjoyed for a lot longer. ‘I had a really nice time today,’ she said. Keith took her hand. ‘I did, too, Mary.’ The smile spread across her face and she leaned in to kiss him. ‘Can I walk you up?’ he asked. Mary glanced at the driveway and the clock and only said, ‘okay.’ Keith tried to get the car door for her, but she wasn’t in the habit, so he met her on the sidewalk and offered his elbow instead. A motion sensor light switched on in her yard at their approach. ‘So, is this the neighborhood you grew up in?’ ‘We moved here when I was in third grade, so pretty much,’ she said, ‘It’s where we do Thanksgiving and Christmas most years.’ Keith peeked through the curtains that hung on the front window. One lamp on a nightstand showed a couch and what might have been a fireplace. Mary brushed his cheek and gave him another kiss. ‘Can I call you tomorrow?’ she asked. ‘Yeah,’ he said, ‘I’ll be home by seven or so.. Conversation sparked from that and Ben used it as an opportunity to flirt with his MILF. Finally, Ben decided to take another step and express that he had a crush on Tammy to her. The likely not sexually active mother of two was flattered. But a few days later, Ben decided to make things more obvious. When he first left his cum in her large underwear, it was uncertain whether or not she knew it was him. While over her house for a party a night later, he left a massive load in her underwear and returned them to her drawer. Two weeks later, they were texting about their word game when Tammy said she was going to sleep. "Wait," Ben wrote, "Do you have a second?" Tammy replied that she did and Ben boldly apologized for the semen leaving. With the adrenaline rushing through his veins, he anxiously waited for her reply. She accepted the apology and added "I was a bit freaked out about the overstepping of boundaries on your part, but it was very flattering which trumps all else." Ben was.
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