Mom’s friends

Finally summer holidays had arrived! Brad had just finished his sophomore year in high school. He had even managed to raise that ever struggling geography grade so his parents weren’t going to insist he worked on it during the holidays. This was actually a bit of a surprise, so for now the grand plan was to practice football and hang out with his friends and then relax as much as possible in between.

“My condolences .. yeah? .. oh? .. sounds nice! .. oh wow, that’s kind of short notice .. I’m pretty sure Ted has to work, but maybe I can bring Brad”. Brad had stepped through the door while his mom, Evelyn or Lyn to her friends, was on the phone. He promptly got her attention enough to show her the piece of paper that should spell total freedom for the duration of the summer. “Ooohh nice! I guess a bit of moms tutoring paid off? … Huh? oh that was for my son, he just handed me his grades. Would you believe a bit of studying with his mom earned him a respectable grade in Geography? What are your plans for the next couple of weeks honey?” Lyn had looked up at Brad and angled the phone down a bit. It wouldn’t sound much different for the person on the phone, but it was enough for Brad to register she was talking to him again. “Ohh, not much, just hanging with a couple of mates I guess”. “Sure we would love to help out. Me and Brad. For the full 2 weeks. I look forward to seeing you girls again too”. Lyn hung up and put the cell phone down on the kitchen table.

“Mom, who was that and what did you just volunteer me for?”. “Volunteer? That sounds work-ish! you call 14 days vacation in Florida work?” “I only heard your half of the conversation” he countered. “You said we were going to help out, that sounds awfully work-ish to me”. Brad should have expected it by now. That comment was bound to start the usual speech about how healthy it would be for him to start making his own money. Brad was doing well in school, but mostly by putting in the extra hours. Whenever he wasn’t studying he was running, lifting weights or hanging out with friends from the football team. He usually claimed the latter was extra training, but in reality they would usually spend an hour on a field or doing something training related and then a couple of hours hanging out. But training or not, he just couldn’t see how he was going to fit a spare time job into that schedule.

“Alright, alright. Maybe I can tutor some middle school kids, or help the coach out with something during the summer”. Brad figured one of those options could be called a summer job, without actually taking too much time away from hanging out with his friends. Besides with a little luck he could spend the time tutoring Sara. She lived just down the road, was one year his junior and always in need of help with math. To top it all off, Sara’s mom absolutely adored Brad, so he was sure all he had to do was ask her if Sara needed tutoring.

“You still didn’t tell me what that phone conversation was all about though!” Brad had to remind his mom. Lyn had pretty much been talking as if Brad had heard both ends of the phone conversation, somehow without revealing any more details than Florida and 2 weeks. “You remember my high school friend Amber?…”

Lyn had gotten pregnant in high school. Both Ted and Evelyns parents had been very supportive of the couple when they decided to keep the baby. Hence Brads father had managed to go on to college to finish his education and Lyns social life had recovered quite well after retaking just one year. By the time Lyn was through high-school she was tight with a new group of girls. A few of her friends went out of town for college as soon as they were through high school and wasn’t around much, but Amber went to a college nearby and had stayed close until Lyn and Ted had to move for Teds new job. Hence, Brad had faint memories of most of his moms high school friends, but since Amber had been around longer she was the one he remembered best.

Brad hadn’t seen Amber since he was 6, but to this day she was still his favorite babysitter. He remembered her as a very large woman, despite later learning she was much lower and thinner than Lyn. But then what grown woman isn’t very large when you’re 6? The memory that earned her the place of favorite sitter was one particularly hot day. They had gone to a secluded lake and Brad had wanted to go swimming, but they hadn’t brought any bathing suits. Brad, being just 6, had simply ditched his clothes and jumped in before Amber could protest, forcing her to go in after him. She had stripped to panties and a t-shirt, both white incidentally, and gone in with him. They had played around in the water for about an hour, then spent the next half an hour drying up in the sun.

Even at age 6 brad had found the image of Amber in completely transparent t-shirt and panties extremely interesting. To this day he could recall every detail of her silver dollar sized areolae, how her nipples had stuck straight into the air, how smooth her pussy lips had looked (although he didn’t give the lack of hair a second thought at the time) and how he had wished he was the piece of fabric in her panties clinging to the crack in the middle of her crotch. Even after finding porn on the internet, the memory of Amber was his favorite jack-off image.

Lyn finally started explaining the phone call. Amber had inherited a cottage in Florida from a deceased uncle. It was reportedly big enough for 5, but the uncle had been ill for a few years, so the cottage was most likely neglected. Amber had seized the opportunity to make an impromptu high school reunion for her closest friends. The way she figured it, they would spend a couple of days shining up the place so it could fetch a higher rent and then get in a weeks vacation of their own. Amber was recently divorced and the 2 other women that would be coming had never married for some reason, so she had asked Lyn to bring her husband in case they needed the muscle. Lyn had figured Brad would make a decent stand in for his dad with the way he kept in shape, maybe even better in some respect, being so young and fit as he was.

“Just how much will I be filling for dad, mom?” The words had flown out of Brads mouth on their own accord. He was almost shocked to hear his own, hidden suggestion. Despite his own shock Brad took the opportunity to check his mom out. He told himself it was just to emphasize the point. She was 5’9, had smooth light brown hair that reached the bottom of her shoulder blades. Her eyebrows were perfectly kept. Her nose was long and thin, pointing ever so slightly upward. Her eyes were a light greyish blue. She had nice D-cup breasts, a slim waist and full, round hips. She was wearing a v-neck shirt that showed just enough cleavage and a tight skirt that showed off her hips nicely.
Lyn didn’t flinch. She just reacted with a cheekish grin and started “Not THAT much, I have plenty in your dads..” Her face suddenly changed to a more serious look “oh!