The Challenge 5: Lisa’s Family - Sex Stories

The Challenge 5: Lisa’s Family

... flight itinerary. Lisa wired several thousand dollars to his bank account and reminded him to save all receipts – should they spend any money. She did not tell him it would be him and Angela alone on this surprise and sudden vacation. ***** “Hi Lenny!” Angela ran to him in the airport in Miami. She threw her arm around him, taking him by surprise, causing him to blush. He always did when she hugged him. “Are you looking forward to this?” Angela beamed. “Yeah, it’ll be cool.” “I’ll say! It’ll be just you and me,” Angela told him. “Uh, what? Just us?” Lenny asked. “That’s right!” Angela took his arm, leading him to baggage check in. “No way,” Lenny thought, attempting to conceal a grin. Angela led him to check his luggage. When he was done they got their boarding passes and made their way to the long security line. “Did you already check your luggage?” Lenny asked Angela, whose arm was still wrapped around his. “Nope, I have everything I need in my carry-on bag,” Angela replied. All she packed was some makeup, various toiletries, two small dresses, two bikinis, and nothing else – no underwear or other clothing. Angela assumed they would be naked most of the time anyway, earning every cent of Bob’s challenge. She talked on and on and on, the entire plane ride. She asked Lenny about college, his goals and plans, assuring him it were ok if he didn’t know yet. Angela flirted too, complimenting him on how cute he was, tousling his hair, asking about his love life. She was ...

... legitimately saddened to learn he didn’t have a girlfriend, genuinely telling him that she thought for sure he would, again complimenting his appearance, his smile, his height. He reminded her of a male version of Alice. Once they arrived, they grabbed Lenny’s luggage and got a cab; the driver made small talk with the Americans. When he asked if they were married, Angela said they were not yet married, causing Lenny to blush. Angela jabbed his side, resting her hand on his thigh. Since Angela wasn’t wearing a bra, the cool air-conditioned taxi made her nipples hard. She saw the cab driver glance back at her through the rear view mirror. Knowing why she was there with Lenny, coupled with the sneaky driver and the fact she wasn’t wearing a bra or underwear, made her even hornier than she already was. At a stop light, Lenny was looking off to his left at the surroundings. Angela’s eyes were locked on the driver’s. She smiled, pulling down her tank top, revealing an erect nipple to him. He smiled and nodded back, the light turning green, and drove closer to the resort. “Free ride, no charge,” the taxi driver said, arriving at the resort. Lenny was behind the vehicle getting their bags. “Thank you, sir,” Angela smiled, bending down, offering the driver a better view of her tits. “That boyfriend of yours going to have a good vacation isn’t he?” The driver asked. Angela grinned, reaching down to grab and squeeze the driver’s erection. “He sure will. Lots of sex. But he’s not my boyfriend, ...