Sweet Catherine's First Experiences (Unprotected Book 1)

by Matt Coolomon

  Catherine just smiled more. This guy was really old, but there were some at the beach yesterday at least as ancient as him.

  “Can I have a look now?” The old man grinned cheekily. “No one’s watching.”

  Catherine looked around. There was no one in sight, and Robbie and Andy were way in the distance. “Are you really Andy’s friend?” she asked.

  “Yeah, sure! You can trust me.”

  Catherine bit down on her smile. “Do you promise not to touch?”

  The old guy had a look around that time. “Yeah, I promise,” he said, gulping.

  “Okay then,” Catherine uttered, and she lifted her top.

  Her little white tits popped out the bottom and jiggled as she caught her breath. She stretched her top up with one hand and leaned back on the other. The old man immediately groped her, feeling her left tit before she had a chance to wriggle away.

  “Hey, you said you wouldn’t,” she giggled.

  He was chuckling and smiling broadly. She pulled her top down and fixed it back into place.

  “Well, I never could be trusted,” he laughed. “But are you going to take your bottoms off today as well, or what?”

  “Yes. I think so. Are you coming with us?”

  “I wouldn’t mind – for an hour or so over my lunch break at least. It’s going to be worth my while, though?”

  “Maybe,” Catherine said, smiling coyly.

  The jet skis were coming quick.

  “You’re a hot little tease, aren’t you?” old George laughed, and she just kept smiling in response.

  Andy and Robbie stayed on their skis. George got on another and told Andy he’d be coming along for an hour.

  *

  “It would be safer if Catherine rides with me until you’ve got a bit more experience,” Andy said to Robbie, and he extended a hand to Catherine. She stepped onto the side of his ski, and he guided her to sit in front. “Here – you drive,” he told her, and he gave her a quick lesson as they made their way out beyond the surf.

  The water was glassy calm half a mile from shore. They cruised along with young Robbie still playing around doing doughnuts and speeding off ahead.

  Andy’s erection was against Catherine’s bottom. He was holding her waist, and she was pressing back against him. He waited for Robbie to zoom off again, and he reached up and felt her tits. She lifted her arms a little, offering him full access, and he massaged them and tweaked her hard little nipples. She was wearing a shoulder bag. He took that and put it on his own shoulder. He then undid her bikini top and pulled it from her, putting it into the bag.

  *

  Catherine held her breath as his hands closed over her breasts again. She could feel his erection pressing against her back, and her legs were tingling because of that. She looked across at the old maintenance man grinning and watching her being felt up. The hands covering her breasts then lowered back to her waist as Robbie swept around and slowed alongside again.

  Robbie looked across at her bare breasts. She met his eyes, and shrugged and smiled innocently. Andy then took over control of the jet ski and headed off toward a small boat that was not far away. Robbie followed, and they pulled up alongside.

  It was a fishing boat with half a dozen guys hanging over the rail looking at Catherine topless. She was giggling, and they were whooping it up. They stayed there for a long while with Catherine completely exposed to them, then they led off again, and Robbie was left behind for a minute.

  Andy placed Catherine’s hands back on the hand grips and spoke into her ear. “Keep going straight,” he said, and he started feeling her up again and playing with her nipples.

  “Did you like that?” he yelled into her ear. “Do you want to do it again?”

  “Okay,” she called back to him.

  There was another small boat up ahead with two old guys fishing quietly. Andy pulled alongside and said hello. They both smiled as their eyes levelled on Catherine’s boobs. She smiled back and sat with her arms down by her sides while they looked at her. Robbie pulled up, and she met his eyes again, following them down to her bare breasts then back up as she bit down on her smile.

  Andy was chatting with the men, and Catherine just sat there watching them stare. “Nice of you to give your daughter a ride like that,” one of them chuckled at one point, and that made her blush.

  Andy laughed. “Well, she’s too big to ride on my knee these days, so this is the next best thing.”

  He touched Catherine’s waist and squeezed a little. George had pulled up, and he and the two fishermen watched Andy’s hands. Catherine went all goose-bumpy and held his wrists.

  “Cute little nipples, eh?” he said to the other men, and Catherine watched their faces and kind of pushed down as his hands lifted and felt her.

  She checked back over her shoulder to be sure Robbie wasn’t watching. He was right there, though, and she blushed back at him, but he zoomed off.

  She had pushed Andy’s hands lower, and he sat there fiddling with the edge of her bikini bottoms. He was just chatting and laughing with George and the two other old men. The three of them were staring at her hard nipples and looking down at her legs and her little pants. Andy had fiddled the edge of her pants down off her hips a bit. He was tugging at the elastic and making the front of them roll down and reveal the top of her little landing strip.

  Catherine’s legs were straddling the jet ski, so her thighs were apart, and he couldn’t actually pull her pants down any further. “We’re heading over to the cove,” he announced, and Catherine pressed right back against his body as he hooked his two index fingers in the front and stretched down past her landing strip.

  He held the front of her pants down and let the old men have a look at her pussy. “Fuck, yeah!” one of them groaned, but Andy just laughed then zoomed off to leave them with their mouths gaping.

  He cruised around the headland to an inlet where the water calmed completely and there was a small sandy beach surrounded by cliffs of rock. There were about a dozen people – a couple of women and the rest middle aged men. The women were nude, and a few of the men were too.

  Robbie ran after Catherine. “Hey, they’re nude!” he exclaimed nervously.

  “Yeah, this is the next level. Completely optional,” Andy explained. “Have a look! She’s all right, isn’t she?”

  The woman they were passing was probably only 30 or so. She looked firm and quite slim, with nice full boobs and a shaved pussy, although her legs were folded to the side modestly.

  Andy led to a spot where a few men were set up, and they all turned to watch. Catherine was still topless. She just smiled back at them as they looked her over. Andy stepped out of his swimmers. His cock swung free, and she tried not to squeal.

  He grinned. “Your turn.”

  Old George was sitting on the sand watching. Robbie seemed dumb struck.

  Catherine untied her skirt and let it go. She then took a breath and hooked her thumbs in her bikini bottoms and pulled them down.

  A few other men had turned to watch. There were about six all up, plus Andy and George.

  She stood there nude in front of them for a moment without moving. She had shaved the night before, so her slit was bald, and they were all staring at it. Her legs were tingling so much they were numb, but finally she was able to move again, and she got down on her knees and took her towel from her bag. She then laid her towel out and bent over to fix it properly.

  Andy had a view of her from behind, and George shifted and leaned around for a look as well. Catherine’s slit was perfectly smooth, bare and pink. Robbie was also just staring at it, and she looked back over her shoulder at the three of them. Then she looked beyond to the other men still watching.

  Andy stayed on his front concealing his erection. Robbie sat down without saying anything. He appeared to be shocked beyond arguing.

  Catherine was glowing. She sat down and started with the suntan lotion, rubbing it on her arms and shoulders. She smiled to herself when sh
e started on her belly and smoothed it up over her breasts, where she rubbed in a bit more than she needed to. She then did her legs, mindful of keeping them together. She suddenly loved being nude in front of strangers, especially older men. It was something she had never dreamed of before, but it was very exciting.

  Robbie was watching the other women walking around and Andy and George were looking too. Catherine met the eyes of a man lying facing her. He was up on his elbows looking directly at her legs.

  She parted them slightly, bending her knees up and allowing them to stray a bit. He didn’t look up, but his eyes widened and focused, which made her heart thump. She then swayed her knees together then allowed them to stray a little wider apart.

  That time she caught George looking, and she met his smile shyly. She wriggled her feet in the sand and kept her knees apart like that, letting him have a look too. She then met Robbie’s eyes, and he looked down at her pussy then back up. She just held his gaze steadily, feeling her cheeks redden and heat up with guilt-edged excitement.

  Catherine stayed resting back on her elbows with her knees apart so the men could enjoy looking at her pussy. She also enjoyed looking at them – at their cocks. Andy rolled over after a while, and she had a chance to sit there watching his rather thick looking penis swell and recede and sort of roll around like it had a mind of its own.

  Most of the men at the beach came by at one point or another – some more than once. And each time one would approach, Catherine would open her legs a little further to let him have a look while she would return the compliment and examine his penis and balls. Some had such huge balls, which she found fascinating – wondering if that meant they would have a lot of semen in them.

  George left after an hour or so. He had overstayed and was late back from lunch.

  “I’m going for another ride,” Robbie said after George had gone, and he took his jet ski out but not too far. Andy then shifted closer to Catherine. The guys close by had moved on, and no one was watching.

  He grinned, looking down between her thighs. “Now that definitely looks tempting!”

  “Really?” Catherine said, parting her knees a little more.

  “Fuck, yeah!” Andy groaned, glancing out to check where Robbie was then leaning in to kiss her.

  He felt her up again – squeezing a breast while kissing her some more. Catherine saw a man looking over. “Someone’s watching,” she uttered, and the guy craned his neck, so she opened her legs wider for him. Andy then rubbed up her inner thigh, and she spread her legs even wider, but his fingers only glanced over her pussy and he didn’t try to finger her.

  “Robbie’s coming back now,” she whispered.

  Andy got up off her and sat back on his towel. There were three men standing there watching. He smiled up at them. “Hey, guys, what’s up?”

  They all grinned. One answered. “Thought there was going to be a show.”

  “No – sorry to disappoint, but that’s it for now.” He followed their gaze down to Catherine’s legs, which were still spread fairly wide. “She does look good, though, doesn’t she?”

  The three of them were staring at her little slit. There was a dribble of lubricant glistening between the smooth pink lips. Robbie walked past them and sat down.

  “We have to head back and return the skis soon,” Andy said. “How about we have another little ride around on the way back?”

  He pulled on his swimmers. The three men moved on. Catherine put her bikini bottoms on and found her top in the bag.

  “Do you want to put that on later?” Andy asked her. “We can stop just before we get back and fix it up then.”

  “Okay,” Catherine said. “Are we going to meet some more fishermen?”

  “Probably will,” Andy laughed.

  He took her bag and slung it on his shoulder. They approached the jet skis. “You lead the way, Robbie. Just follow the inlet there…. I’d better ride with Catherine again.”

  Catherine held Robbie’s gaze as she got settled on the seat with the older man straddling behind her. The guy had to adjust the position of his penis, which quickly firmed against her back. It seemed he had released it from his pants.

  Robbie’s eyes rolled and he took off. Andy followed along a fair way behind. He then allowed Catherine to take over, and he started playing with her tits, just pinching her nipples and pulling on them.

  “Do you want to come up to my room tonight?” he shouted over the sound of the ski.

  “Okay,” Catherine called back. “I’ll try to sneak out after dinner.”

  “If you do I’m going to fuck you.” Andy reached down and rubbed her through her bikini pants. “I’m going to fuck you hard!”

  “If you want to,” Catherine said to him.

  20

  The inlet became a small river that wound between the houses and farms of a local village and past another few hotels before it led into the back of the resort. Catherine was still topless when they entered the maintenance building and pulled up at the small indoor boat ramp. George was there with a young worker about Robbie’s age who was having a good look while she searched in her bag for her bikini top.

  Catherine stood facing the men while she put her top on, and she smiled at them before finally covering her breasts. She was already trying to think of how she could ditch Robbie after dinner and sneak off to Andy’s room.

  As soon as they left the boat house Robbie was at her.

  “I can’t believe you wanted to strip for those old guys. You showed them everything!”

  “Well, it was exciting! Don’t you want this vacation to be exciting?” Catherine asked as she cuddled close.

  Robbie kept his arm around her as they walked. “Yes, I want it to be exciting, but I didn’t know we were going to some nudist beach.”

  “But I feel like I’m learning about sex finally. Don’t you?”

  “Learning about it? What do you mean?”

  Catherine cuddled up in the elevator. “Well, so far it’s just been kid’s stuff, and this is a chance to see what adults do. I think if we hang out with a guy like Andy it’s going to be more exciting for us together. I think I might want to go further than we have before.”

  “Further?” Robbie echoed. “You mean?”

  “I mean, I think so,” Catherine said with a kiss. “So far I’ve been saying no because I wasn’t sure we would know what to do, but these older men have a way of looking at me that feels different. I think we should do more of what they say and see what happens.”

  “See what happens between us?” Robbie asked, stopping Catherine in the hallway at her door. He kissed her and she responded. “So you’re saying the more we hang around with these old dudes the more chance we might go further?”

  “Yeah, I think so,” Catherine uttered. “Let’s make this vacation like a time out from the boring stuff at home, okay?”

  The parents were in Catherine’s room drinking and planning to have a dinner party there on the balcony. Robbie and Catherine were to at least stay until they had eaten. Their parents had hardly seen them in the few days since arriving, and they insisted on a few hours of family time. Both mothers were half drunk and laughing at everything, and both fathers were obviously half cut as well – at least half cut.

  Catherine felt Mr Dale’s eyes following her everywhere. He always did that but was doing it a lot more than usual. She sat on a deck chair directly across from where he was leaning against the balcony rail, and she bent her knees up a bit while allowing them to part slightly.

  He looked at her bikini pants, and she smiled to herself and parted her knees a bit more. As she sat there with everyone chatting and laughing, she wondered how she could flash him properly. Whenever he leered down at her legs, she opened them for him, but it was only in a bikini.

  When he went to the toilet she decided it was time to get changed. Her room was next to the bathroom, and she waited by her open door, but her dad came along before Mr Dale came out. He was waiting for the toilet, and C
atherine had to close her door and miss the opportunity completely.

  She changed anyway, picking out lacy, white panties and a short denim skirt. She also decided to go braless beneath a half-length t-shirt her girlfriend had given her as a joke one time. It was very thin white fabric that was virtually see-through, and it only just covered her boobs while being open underneath and loose fitting enough to flash them easily. If she put her hands on her head, her nipples would pop out the bottom.

  Her mother’s eyebrows raised when she walked out in it, but she just shook her head and didn’t say anything. Her dad had a look, and Catherine kept her eyes averted while his gaze lowered to her breasts and settled there for a while. He didn’t say anything either, and she noticed he kept glancing over quite frequently, which was a little thrill in itself at how naughty she was being.

  Mr Dale was in the same spot leaning against the rail. Her dad was next to him but not directly in front of Catherine’s deck chair. The mums were sitting back closer to the open balcony doors. Robbie was inside on his computer.

  Catherine sat down in her chair and rested back with her knees bent up again. She felt much sexier with the lace panties she had chosen, and her skirt was straight enough that they were exposed to Mr Dale’s view whenever he looked down. She wasn’t sure if her dad could see them too, but that just made it even more exciting.

  Mr Dale’s eyes lowered, so Catherine looked away. She checked and saw that he noticed, and she also saw her dad glance. Her dad then looked up at Mr Dale’s face, but then his eyes returned to Catherine’s panties, and that made her face go hot, but she looked away again and pretended not to notice.

  She sat there like that for a long while before her mother and Robbie’s mother went to answer the door and start getting the food from room service ready for dinner. Her dad and Mr Dale were kind of chatting together and looking out to the ocean, but they were both looking down at her quite regularly. Every time Mr Dale would have a look at her panties, her dad would glance down as well then sort of watch Mr Dale’s face.

  Catherine stretched her arms back above her head and yawned as she settled like that. Mr Dale and her dad both looked, and she felt the breeze on the underside of her breasts. She did another big exaggerated stretch and felt the fabric of her t-shirt lift above her nipples. She felt them both staring, so she yawned and stretched even longer, then she relaxed and her shirt slipped lower to cover her, but her nipples were hard and poking at it. And she sat up with her legs crossed and her little straight skirt stretched taut and hiked up to reveal her panties while she brushed her hair.