This story is a sequel to "Flattering" Best Friend's Mom. All characters are over the age of 18. The story is based off of real events.
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Ben and Matt are going to college next year and, with that, comes extremely difficult decisions. Ben and Matt had just been admitted into the same university, but neither of them had visited yet. A road trip was in store and, with two working fathers, the mothers, Carey (Ben's mother) and Tammy (Matt's mother), would be driving.
Ben and Tammy had not spoken about their sexual endeavor. Ben wondered if the trip with Tammy would spark any awkwardness amongst the duo. Carey would be driving her smaller, electric car so they wouldn't have to pay for gas the entire 5-hour car ride. The size of the car created slight issues on who would be sitting where. Carey suggested that due to Tammy's size she should sit in the back row so she can extend her legs horizontally. Ben pleaded for the back row, telling his mother that he really needed to sleep during the ride. Matt gave in and offered to help Carey navigate on the journey.
Now before things begin to heat up, let me give you an image of what everyone looks like.
Ben Wilks was an 18 year old, gifted student offered a full ride at the college. He was tall, tan skinned, muscular, and handsome. He was a charmer, a popular guy known to hook up with some of the best looking girls in the schools.
Matt Bomes was of the same age, not as social or attractive, but had a good sense of humor once he was in a comfortable situation.
Carey Wilks was nearing 50, but she didn't she look anything over 35. She had a nice pair of boobs that stood tall below her straight, brown hair. She was a great package; successful and pretty.
Tammy Bomes, her best friend, was a few years younger. Tammy was a bit larger, but had a very pretty face. She worked as an accountant, but worked few enough hours to be able to enjoy the perks of being a housewife.
The four of them loaded up the car in the morning and Tammy and Ben hopped in the back, while Tammy's son, Ben, joined Carey in the front. So early in the morning, Tammy and Ben wanted to take a snooze for at least the early portion of the ride. As Ben closed his eyes, he got a text from the sprawled-out Tammy.
"Massage my feet," she wrote.
Tammy kicked off her flats and out came her freshly painted toes. Under his blanket, Ben reached for them and began rubbing his thumb along her sole. While Tammy emitted soft moans, Ben caught her gliding her hands along the inside of her thigh. A hard-on emerged underneath Ben's sweatpants. Hoping to get her attention as she leaned comfortably against the car window, Ben texted her, "How am I doing?"
"Amazing :P," his favorite MILF replied.
While still caressing his best friend's mother's ankles and feet, Ben dozed off into a light sleep.
Meanwhile, in the front row, Matt was attempting to make his fantasies come true. Matt had once said to Ben that he had masturbated to Carey once, but that was so far from the truth. As a horny teenager with no sex life, Matt's jerking off was everything to him and Carey was a favorite of his. He made small talk with Carey throughout the ride, but Ben happened to catch his best friend call his mom "the most beautiful woman in town." Ben smirked, but didn't mention anything to Matt.
Carey wasn't shy in flirting back. After she peaked to check that Ben and Tammy were asleep, she said to Matt that he had developed in a handsome young man that will surely make a young lady very happy. As Matt blushed, Carey stopped the car, smiled at Matt, and then woke the back row.
"We're here!," shouted Carey.
Getting out of the car, Ben caught Matt's blush and happened to drop his phone. As he reached down to pick it up, he noticed his best friend's hard-on and grew curious as to what was going on in the front row.
It was touring time. As the walking tour went town, Ben would sneak glances at Tammy and always try to bump into her chubby butt as they strolled through campus. A few times his fingers slid across, enough to get him hard. Tammy knew what he was doing and felt the moistness between her legs as she continued to fantasize about the young man.
Time flew that day and, after a short dinner, they checked into the hotel. Carey had booked two rooms, one for the mothers and one for their sons. The front desk asked them if they would mind connecting rooms.
"No, of course not!," Tammy said as she tried to wink at Ben.
They settled into the rooms and immediately cracked open the connecting door so unpacking could be made easier.
"Carey, I brought a bottle of wine for us and the Rummikub set for us all. Guys, want to play after you put away your clothes?," Tammy said.
Ben and Matt accepted their offer in unison. A few minutes later, they met in the moms room and began playing on one of the beds. A few games went by and Carey and Tammy had each had a glass or two of wine when Matt expressed his boredom with the game.
"Lets play something fun. What about truth or dare?," Matt asked the group.
All about confused, but secretly turned on by the idea, they asked him what kind of topics would this game entail.
"I don't know. We'll see where it goes. I'll go first. Someone give me a truth." Matt said with a smile.
"Ok, is it true that you flirt with your marketing teacher?," asked Ben.
"Yes! I don't care that she's older!," Matt exclaimed.
