The Challenge 5: Lisa’s Family - Sex Stories

The Challenge 5: Lisa’s Family

... got a nice size down there.” “Oh you saw it?” “Mmhmm, by accident. It happens.” “Well then, I suppose I might actually enjoy this.” “I know I would,” Lisa muttered. ***** Lenny had been home alone for a couple weeks. To an 18-year-old horny teenager, this was a dream come true. The only time he saw any people was when he was at school. Upon arriving home, he stripped naked, masturbating until he fell asleep, resuming in the morning before class. The number one woman he jacked off to was one whose pictures he downloaded and saved to his computer. He looked at them every day. They were picture galleries for various photo shoots. He even managed to download a behind-the-scenes video of one of the shoots. Lenny was sad this day, because he knew his mother would be home by the time school let out. He hoped the house was clean enough so the short, sassy, little woman wouldn’t scold him. When she did, by sticking her finger up at him, he almost couldn’t help but laugh. Lisa would get angrier, demanding he stop laughing at her, sometimes even laughing at herself. The image of a 5’2”, busty, brunette scolding a tall, lanky 6’2” teen was admittedly comical – even to her. Since he was the only one living at home, he and his mother bonded, becoming closer, almost like friends. Lenny wondered if it was because she was dating a younger guy or if it was because she accidently walked in on him getting out of the shower. Lenny never forgot the look of shock mixed with admiration for that ...

... split second on his mother’s face. Lisa apologized profusely afterward. That morning when Lenny shot his load one last time before his mother got home, he wondered why he never thought of her. He’d always shake his head when thoughts of her large breasts popped into his head when he was jacking off. He told himself he wasn’t like that. No, he had another main girl in his fantasies. For some reason lusting after this particular woman didn’t feel as weird. When Lenny arrived home from school he was surprised by Alice. He didn’t know she was visiting. Lisa jumped up from the couch, giving him a huge hug, ushering Alice to join her. Alice gave him an awkward hug, trying to press her breasts again him, but not following through. Lisa told her to take it slow if she wanted it to be mutual. At dinner they talked about Alice staying for awhile. Taking her mother’s suggestion, she flirted with Lenny, asking if she could share his room with him, giving him a kiss on the cheek when she got up for seconds. It didn’t seem to have an effect on him. Later that night, they watched TV, Lenny sitting in between his mother and sister. Alice leaned against him, feeling awkward as she did. When Lenny got up to go to bed, Alice said she was too, followed by Lisa. Alice jokingly suggested Lenny sleep in his mother’s bedroom with her and Lisa. He politely declined. Alice and Lisa feigned disappointment, “What 18-year-old wouldn’t want to share a bed with two women?” Lisa asked. Lenny rolled his eyes and ...