When Matt's parents first mentioned this year's family vacation to kick off the summer, he was less than thrilled. It wasn't that he didn't get along with them, he just thought it was, well, lame. His mother wanted the whole family to get together before he went back to college (his sister would also be starting her freshman year), and wanted them to be alone. Some colleague of his dad's owned his own island in the Caribbean, and offered to let them use it. That part was cool, and he knew the house would be awesome, but vacationing at the beach was supposed to be in a college party town with pussy running around everywhere, not stuck on a secluded island in the middle of nowhere with no one around but family. His only solace would be the scenery.
Sure, staying in a tropical paradise would offer a scenic panorama equaled no where else on earth, but that wasn't what he had in mind. No, Matt had a dirty little secret. At just under a year younger than him, Matt's sister Nicole had blossomed into an all natural boner-fide hottie. And, from Matt's point of view, his mother was definitely the reason why. He had always felt guilty about ogling and having impure thoughts about the only two women in the world he couldn't have and wasn't supposed to look at, but not guilty enough to stop. Not to mention, he had become a pro at looking without being caught. He considered himself a master.
********
"How many swimsuits are you taking, Mom," asked Nicole. They were in Nicole's room, Donna helping her daughter pack.
"I don't have as many as you, dear," she replied. "I'm not a hot little coed."
"You may not be in college, but you're definitely hot, Mom," said Nicole. "How bout I take all mine and we can share?"
"I couldn't wear these, I'm a mom," she replied, holding up a particularly skimpy thong. "Besides, if we both dressed like this, it would kill your brother."
"I know, right?" she giggled. "He thinks he's so subtle. The other day I caught him trying to sneak peeks up my skirt."
"And you, no doubt gave him a show, didn't you?" It was supposed to be a reprimand, but she couldn't be mad. After watching Nicole strut her stuff, she, herself had shown off a little. Both women were flattered and enjoyed being an object of desire, no matter how wrong it was. Besides, Matt was a hunk. As long as it went no further, it was no harm, no foul.
"Maybe a little," Nicole laughed again.
"Be nice!"
"C'mon, Mom, he's a perv," she replied. "I was being nice."
********
Matt was already having the time of his life. By the time they left for the airport, he had completely changed his mind about vacation. Nicole and his mother had gone shopping and bought up every revealing article of clothing in town, it seemed. His dad had even noticed, although he hadn't said anything. But Matt knew. Sneaking peeks for years, he knew what to look for, and caught his dad checking Nicole out. This vacation would definitely create masturbation fodder for years to come. Apparently for both Matt and his Dad.
In the airport, while he and his father took on the familiar job of carrying all the luggage, Donna and Nicole paraded through the airport like royalty, loaded with only their carry-ons. Meanwhile, Matt took in the first exciting view of the vacation. Mom was dressed demurely in khaki shorts and a loose fitting top, but her clothes had always looked good on her. Her semitransparent white blouse revealed the outline of her bra, while accentuating the tan, toned skin around it. Noticing that her short, tight shorts were more risque than he thought at first glance, he relished the tempting sway and teasing cheek-peek of her youthfully round ass as she walked. And Nicole. Gawd damn! Were they boy shorts? Booty shorts? Whatever they were called, the spandex-like material hugged every curve, and crawled just slightly into the cleft of her delectable ass, the hem ending just below her firm cheeks. The titty shirt she was wearing wasn't much different than the ones she usually wore, except that the spaghetti straps on this one made wearing a bra impossible, barely restraining the delicious jiggle of her C-cup breasts, the soft material rubbing her nipples just enough to keep them on point. In addition, her low riding shorts coupled with her short, tight shirt clearly showed the dimples in the small of her back. The waistband of her panties rode slightly above the waistline, giving a professional ogler like Matt the perfect opportunity to follow it all the way to the sexy thong arrow nestled at the top of her crack.
"What are you looking at, boy?" asked Jack, leaning over, talking quietly.
"Dad! I'm... nothing," answered a flustered Matt.
"It's ok," he chuckled. "We have two of the hottest blondes in the world, showing off for all to see. You can look, but, remember, you can't touch. We damn sure don't need any two-headed babies with tails running around."
"Damn, Dad!" Matt laughed.
"You don't say anything about me looking and liking and I won't say anything about you," he said. "Deal?"
"Sure, dad," said Matt, thoroughly confused. He had spent years thinking he was the biggest pervert in the world for looking at his own mother and sister like that, and now his dad was openly admitting to doing the same thing with his own daughter. Not to mention the don't ask, don't tell conspiracy to look freely upon them. Weird!
Nicole and Donna waited in the background while Matt and Jack checked the luggage. As soon as they finished, the ladies immediately unloaded their carry-ons on Matt and his father. Giggling, they rushed off, leaving the two men carrying everything once again. Resigned to their fate, they followed close behind through security and to the boarding gate.
After only ten minutes, it was time to board the plane, when Matt got his first surprise. He figured his parents would sit together, but Donna held him back at the line, grabbing her carry-on from him, claiming she couldn't find her boarding pass. He tried not to stare as she bent over to look for it inside the bag, but the sight of her deep cleavage as her shirt drooped open was too tempting. With two buttons undone, he could see the top of both tits all the way down to the cups of her bra, where her nipples made the slightest dark spots in the thin material. The enticing jiggle as she dug through the bag caused an all too familiar stirring in his loin. He tried unsuccessfully to hide his growing bulge.
"Oh here it is," she said, grabbing it out of one of the outer pockets. "Silly me..." There was a distinct pause as she looked forward, eye level with the sizable bulge in his shorts.
"C'mon Mom," he stammered. "They probably won't wait on us."
"Of course," she said, recovering from her shock. Walking through the tunnel on the way to the plane, she thought about the bulge she had just discovered. Over the years, she had become pretty adept at creating hard ons, and had always liked checking for the telltale signs, but the size of Matt's took her completely by surprise. Was that thing for real? she wondered.
Matt couldn't believe his luck. First, he had seen those tits he had always dreamed of. Sure, they were covered with a bra, and her bikinis over the years had covered less, but he could clearly see where her nipples were. That was a first. Now it looked like he would be sitting by her on their long flight, giving him more opportunities to see more of her. He had been looking forward to sitting with Nicole, but this was even better. This was the jackpot! On the plane, he saw his mother reaching up to put her bag in the overhead. He was about to comment on being so many rows behind his father and Nicole, who seemed to be ignoring each other, when he was struck dumb. As Donna stretched, her amazing body was put on full display. He ran his eyes up her legs and across the swell of her gorgeous ass. With her arms over her head, her tits jutted up and out, pulling her loose blouse taut against them. Nice.
"Want me to put yours up here, too, sweetie?" she asked.
"No, it's ok," he replied. "You wanted to sit by the window anyway, didn't you?" He should have let her do it. His hard on was worse after her little stretch show, and the only open spot in the overhead was right at the seat. If she even glanced in his direction, she'd see it. Shit!
She did. Donna was mesmerized once again by her son's obvious erection. She gazed freely at the lump in his shorts, unaware that Matt had seen her. As she followed the length of her son's boner, she marveled at its sheer length and girth. Wow, she thought, that might just be the biggest cock I've ever seen! Although she'd never had any complaints about her husbands package, Matt was clearly much bigger than his dad. With a slight smile, she decided that before this trip was finished, she would see his bare cock, somehow. She would just have to be careful not to go too far. She wondered if Nicole knew, deciding not to tell her.
Matt was embarrassed. Taking as long as he could in putting his bag up, he wondered how bad she would chew him out. She had to know that looking at her had caused his raging hard on, and then he saw her looking at it. He could only imagine how pissed off she was. She must have been beyond pissed because she just kept staring. Sitting down beside her, he cringed inwardly, waiting for her wrath. Or, worse yet, her rejection. He stared straight ahead, trying to make the damn thing go away.
"You have to put your seatbelt on," said Donna, raising the armrest between them and grabbing the belt on either side of him. "We're about to take off, you know."
"Sorry, Mom," he said, reaching for the belt, trying to ignore his mother's firm breast pressed against his arm. Talk about making it worse! She shook his hands off and latched the belt, the back of her hand lightly grazing the head of his cock, making it throb uncontrollably.
"There," she said, patting his thigh. She wrapped her arms around his arm and leaned on his shoulder, her left hand on his knee. As she pushed his arm back down, his hand rested on her thigh, just below the hemline of her shorts. He left it there. "I'm not ready for an empty nest, Matty. That's why this vacation means so much to me. It's my chance to be alone with you and Nicole before you leave me."
"It's just college, Mom," he laughed. Donna was the only person in the world who could call him 'Matty' and get by with it. "It's not like we're never coming back."
Despite his lighthearted demeanor, Matt was on pins and needles. With his arm nestled between her soft, warm breasts, his hand on her bare thigh, and the womanly smell of her perfume so close to his face (the same perfume that had provoked so many spank sessions), there was no way his woody was going down now. Not to mention, she had touched his cock! He knew it was accidental, but wow!
"No, it's different now," she said. "After college you and Nicole will go out an make your own lives, while I'll be left alone. I know that's how it's supposed to be, but I don't have to like it."
"It won't be like that, Mom," he replied. There was something he didn't like about what she'd just said, but he couldn't put his finger on it.
"Are you sure you don't mind spending two weeks with just us," she asked. "There won't be any pretty girls for you to look at this time, you know."
"I'll survive," he replied.
"Are you going to tell me you don't mind not having anything pretty to look at," she teased.
"Who said I wouldn't? You'll be there, won't you?" He knew she was fishing for compliments, a game they played quite a bit.
