Ned bit his lip hard as he came on his stomach for the third time that day, thinking about his sexy new friend. This family vacation his older sister had forced him to come on wasn't turning out to be as bad as he had anticipated. Ned, at 19, was the baby of the family. A surprise to his parents who were both 49, and having had just sent their youngest to college, thought they were done with kids until the inevitable grandchildren started to arrive. The vacation was a joint celebration for their mom's 70th and Ned's oldest sister turning 50. Among the thirty plus family members, the closest adult to Ned's age was his 38 year old sister Emma, he loved but couldn't confide in about why all of a sudden this vacation was the best thing he could have agreed to.
One thing Ned appreciated about his family was their ability to include everyone in the celebrations, even strangers. Like last night. The first proper night of the trip. They'd spent the day at the beach and come back to the resort in good spirits. A few people had joined the group but the one that caught Ned's eye was Nancy, a petite yet curvy redhead from England. She was about the same age as Emma, and they had spent the night chatting and mildly teasing Ned. Nancy was gorgeous, about 5"5, with shoulder length wavy red hair and bright blue eyes, but Ned couldn't take his eyes off her cleavage. Her green leaf print maxi dress was a low cut v at the front showing off her large chest, and was almost sheer so Ned could see her dark nipples and lacy underwear when she stood in a certain light.
Nancy was the perfect woman in Ned's opinion, especially after Nancy dragged Ned up to dance. Ned, a skinny nerd, who at almost 6'4" was the tallest member of his family, had a mop of dark auburn hair and glasses which he'd always been self conscious about, but he'd heard Nancy tell his sister that if she'd been at the same college at the same time she would've 100% gone after him. Nancy told Emma she thought Ned was gorgeous and when Emma pointed that Ned was behind her and heard, she shrugged her shoulders and told Ned he was her ideal man, it was just a shame she was old enough to be his mother. Ned thought to himself that nothing he wanted to do with Nancy was mother/son appropriate and he'd spent a lot of time, dick in hand, thinking exactly what he would like to do with Nancy.
A few days later, after various activities with the family and clumsy flirting with Nancy, Ned decided to spend the day by the pool. After breakfast the family went off to their various activities and Ned headed back to his room to grab his towel, his book and sunscreen. He opened the balcony door to retrieve his book and he heard music playing. As he walked to the edge of his balcony he saw Nancy come out of the room directly below his wearing a bright yellow bikini, her hair in low bunches. The top was 50s style halter neck and the bottoms were high waisted but high cut on the legs, making nancys legs look much longer. Ned felt a twinge in his dick and watched as Nancy got herself situated on a cabana, marvelling in the sight of her peachy ass as she bent over to straighten her towels. Just as Ned was about to go into his room to grab his own towel and sunscreen, Nancy whipped off her bikini top and squirted a healthy amount of sunscreen on her large boobs. She turned around as she rubbed in the lotion and spotted Ned. Before he could retreat, Nancy grinned at him and beckoned him down all the while rubbing in the sunscreen, paying attention to her large brown nipples. Ned gave a thumbs up and cursed himself for being so dorky. He stumbled into his room and realised there was no way he could go downstairs in his current state, he had a huge hard on, and Ned knew he was blessed in the dick department. When soft it was like Ned himself, long and thin, but hard it seemed to not only grow in length but also double in width. He realised he had two options, but he already felt pervy for accidentally spying on Nancy, he couldn't possibly jack off over her applying sunscreen. He took a deep breath and through about the book he'd just finished, his last algebra assignment and his brilliant, yet old and eccentric looking professor for a few minutes until his erection had subsided and he was able to grab his things and head down to the pool to join Nancy.
"Hey Ned!" said Nancy warmly as she stood up to give him a hug. Ned tried to turn his crotch to stop his inevitable erection hitting Nancy square in the ribs, given their height difference and was marginally successful. The feel of Nancy's warm and squishy breasts against his lower chest felt incredible and he could feel himself rising to attention again. Just as soon as the hug started it stopped, although Ned would've happily held this gorgeous woman all day long.
"How are you doing babe? You ok?" Nancy enquired. Ned nodded and they had a few minutes of small talk before Nancy stood up and told Ned to lay down, he was starting to burn and she needed to apply sunscreen. Ned laid back and Nancy knelt next to him, spraying him liberally with sunscreen and started to rub it into his shoulders, working down his arms and then back to his shoulders. She worked her way down, making sure every inch of his chest was completely covered in sunscreen. Just as Ned thought she was done and he could discreetly adjust his swim shorts, Nancy picked up the sunscreen and sprayed Ned's lower stomach, from his belly button down to the waistband of his shorts, which were resting just below his hip bones. Ned was blushing furiously, his dick was hard while watching this beautiful, half naked older woman rub sunscreen into his body with her tits exposed, inches from his face, from his fingers. Ned inhaled sharply as one of Nancy's hands pulled the waistband of his shorts down an inch, just enough to expose the top of his newly trimmed pubic hair so the other could rub in the sunscreen. Ned made eye contact and Nancy grinned "Don't want you burning babe! Now turn over!"
Ned couldn't believe what was happening, this gorgeous older woman spending time rubbing in sunscreen, but part of him was grateful, he knew his ginger genes inherited from his dad would cause him to burn if not properly protected. He rolled onto his stomach and tried to discreetly adjust his hard cock into a comfortable position as Nancy started to spray his back with sunscreen. Just as he thought he was ok, he felt Nancy straddle him so her crotch was directly over the base of his spine. Her could feel her warmth on his back and he held in a shudder as rubbed the sunscreen in, across his shoulders, down his arms and back to his shoulders. As she worked her way down his back Ned wondered how long it would be until he inevitably came in his shorts. Just then Nancy scooched herself down so her legs were either side of Ned's upper thighs, but the heat of her pussy was no longer on Neds back.
"All done!" Nancy jumped up, and Ned rolled over, momentarily forgetting the tent in his shorts "can you do my back please? Oh, never mind, I need some colour on my front, it can wait!" Nancy said with a sly look at Ned's crotch and a smile on her face. Ned was mortified but thankfully Nancy's personality glossed over his embarrassment easily and soon they were laid talking about their favourite movies:
