Sweet Catherine's First Experiences (Unprotected Book 1)

by Matt Coolomon

  Alex greeted his guests while Milton sat down and continued examining Catherine’s crotch. He could just make out the texture of a thin strip of hair through the white lace. She remained standing beside her father. He was busy chatting with Alex. She lifted her arms and reached back to her hair, the skirt of her dress rising further and exposing the front of her panties more fully. It lifted almost to the waist band and remained hiked up like that while she fiddled with her pony tail.

  Milton glanced and caught her eyes as they flashed away. She was blushing and biting a grin. He looked back down at her barely concealed little pussy, noting the shape of the puffy lips and furrowed slit.

  “What do you think, Milton?” Bruce asked.

  Milton quickly looked up from what he was doing. He’d missed what was being spoken about completely. Bruce’s eyes narrowed. He knew….

  “What do you think if we all chip in and hire a trailer next weekend – to get rid of this rubbish?”

  “We could team up and help each other tidy up,” Alex added.

  “Yeah – good – I’m in,” Milton agreed. He couldn’t help averting his gaze to watch young Catherine walk over to where the boys were cleaning the pool. He just shrugged helplessly when he turned back to meet Bruce’s glare.

  Milton kept one eye on Catherine and was caught out by Bruce a few more times over the next hour while they ate. He noticed she was braless. He managed to get a seat on the same side of the table with only Jared between. There was a good side view of her little boob, which Jared was noticing too. Milton’s son, Robbie, and another boy, Foley, were getting an eyeful from the other end of the table. Bruce was watching them but could do nothing about it. Alex was directly across from Catherine, so she was actually surrounded by all the males present, and the boys had her giggling and playing up to the attention.

  After the meal, Milton stripped off and claimed a floating chair in the pool. He was pleased that Bruce and Alex went inside to play pool. The women were talking together and drinking wine. It was just the three boys and Catherine to join him for a swim.

  “But I need to get changed first,” Catherine announced.

  Jared was inside getting his swimmers. Foley and Robbie had dived in. Milton floated to the edge near the dressing room and rested his arms back. Catherine held his gaze as she approached. He looked at her legs and up her dress at her little panties again as she walked by. The two boys were duck diving, distracted. “That’s a pretty dress, love,” Milton said.

  “Is it?” Catherine stopped and brushed the skirt down.

  Milton tilted his head to look directly up it. She waited. He could see between her legs – the thin strip of soft white cotton covering her slit, her tiny landing strip through the lace front. She stretched the front of her dress down, and he saw the underside of her tits.

  “I’d better get changed,” she said through her sweet little blush.

  When she returned, she quickly got in the water and was claimed by the boys. They had her squealing and giggling as they played with her, having a game of volley with a beach ball while Milton held the leaf scoop across as a net and enjoyed the show.

  The boys had turns partnering young Catherine – lifting her to jump for the ball – touching her. The cool water was good for Milton’s constantly threatening erection.

  Bruce came to take the girl home and left Milton and the three boys floating there in the pool watching her leave, wrapped in a towel and giving a little wave and smile over her shoulder. Young Foley and Robbie went inside to play darts. Jared drifted over beside Milton. He was a bit older than the other boys.

  Milton shook his head. “Fuck she’s hot, Jared. That’s one scorching hot little piece of arse.”

  “I’m trying not to notice,” Jared replied. “She’s always been like a little sister to me.”

  Milton chuckled. “Good luck with that, son….”

  5

  The next afternoon Catherine collected her bag, intending to breeze out the door with a hug and kiss for her dad to stop him from arguing about giving her a lift to Anne's house himself – since he was home and had nothing else to do.

  He was actually very nice, and Catherine loved him to bits in spite of having to trick him sometimes. She ended up letting him drive her to work and gave him an extra big hug.

  Throughout her shift, the guys were looking over at her and laughing amongst themselves. She knew they were talking about her and probably comparing notes on how far each of them had gotten. And that affected her, causing her to feel herself blushing with embarrassment every time one of them would walk past her checkout.

  It made no difference at the end of her shift when Des cornered her in the staff room, though. He had closed the door and had her backed against it. He started kissing her, and her legs went all tingly. He forced his tongue in her mouth, and she melted into him. Then he started feeling her boobs, and she couldn't move. She just let him do it while he teased her about Raymond having a look at them the night before and how he and Reece should be allowed to have a look as well.

  She just stood there while he pulled at the front of her uniform and had a look down it. He stretched her bra out as well and could see her nipples, which were hard.

  "Yeah – nice," he grinned, and she just blushed – and he kissed her again. That time he smoothed his hand down over her belly and grabbed her between the legs, and Catherine moaned into his mouth and relaxed, allowing her thighs to part.

  She clung to his shoulders because she couldn't stand up without holding onto him, and she opened her legs more, allowing him to do what he wanted.

  They were blocking the door and couldn't be seen through the window. If he wanted to finger her she was going to let him, but suddenly his name was called out over the loud speaker to assist in the car park.

  "Fuck!" he said, and Catherine just smiled at him, biting her lip submissively.

  He then worked around the edge of her panties and forced his middle finger up into her. But the manager announced his name again, and Catherine just closed her eyes and relaxed her legs a bit wider. He had his finger all the way in, and he was jiggling it around with the palm of his hand inadvertently rubbing against her clit.

  "Fuck – I have to go!" he groaned, and he jiggled a bit more then pulled his finger out and wiped it on her inner thigh. Then he shifted her aside and pulled the door open to hurry out to the car park and collect trolleys.

  6

  Catherine was in a bit of a trance as she picked up her bag and walked out the back to wait for her ride. It was only a few minutes until Anne's brother turned up in his old Dodge pickup, and she was squashed in between him and his best buddy. She could still feel her wetness on her thigh, and she hadn't thought to fix her uniform from it having hiked up a bit when she slid into the middle of the seat.

  Her panties weren't quite on display, but they nearly were, and her leg was being touched every time Anne's brother changed gears. She had her legs together on one side of the gear stick, but it was one of those big long ones that stem up from the floor, and she didn't have much room between it and the other guy's big, hairy thigh.

  The other guy was Brett, and Anne's brother was Adrian. Brett was fat but Adrian was built. His huge bicep was stretching the sleeve of his t-shirt. He worked at a lumber yard – probably chopping down trees and lugging them around on his shoulder, Catherine imagined as she sat there dreamily taking in the scent of them both.

  "How about we make Nev ride in back and you come on down with us instead of catching the train?" Adrian suggested at one point. Nev was Anne's boyfriend. He was yet to be picked up.

  "No, thanks. I'm looking forward to my train adventure," Catherine answered sweetly. "It will be nice to see you down there, though."

  That half hour ride had passed in a daze for Catherine. They were already at the train station, and the guys left her there with her bag and sped off whistling back at her and whooping it up.

  Still in a bit of a daze, she boarded the train that wa
s there waiting and got her seat beside an old woman who must have been 50. The carriage was pretty full. There were two seats either side of the narrow aisle, all facing forward. By the time the train departed half an hour later, it was getting dark.

  7

  Catherine slept for a few hours then woke to find some of the passengers had gone. There had been several stops, and not everyone was going all the way down the coast.

  She decided to get changed out of her work uniform and wandered off in search of a bathroom.

  The next carriage along was sleeping berths. They were small rooms with the aisle along one side lined with big windows that were all open, and men were sitting on the ledges smoking.

  She edged her way along the aisle being thrown side to side as the old carriage lurched and swayed. It was a very old train with the full range of clanks, clunks and unexpected jolts. At the end of the sleeping car was a bathroom that was big enough to get changed in, and it even had a mirror.

  Catherine had brought a pair of track pants and a light sweater. That morning she had chosen a frumpy old bra her mother had once picked out for her. It was ugly and huge but it was really comfortable to sleep in. She suddenly blushed at the thought of Des looking down her front earlier – the fact he would have seen it!

  After getting changed into her travel clothes, she explored further and found the dining car where she used her ID to buy a can of rum and coke. But just one! To add to the adventure and all. She also bought a meal and sat there in the dining car to eat.

  The walk back to her seat was even more fun with the rather strong rum drink having gone directly to her brain and adding considerably to the swaying and lurching of the train. She had her work uniform in a plastic bag with the soap and deodorant she had used, and she was carrying a can of soda in her other hand and kind of bumping her way from side to side along the narrow aisles. Then when she got to the sleeper car with a few men smoking, she had to apologise for bumping into each one of them – or rather, giggle and apologise.

  Two of the men were cheerful and polite about it. The last one was smiling too but he caught her and held onto her with his hands upon her waist and his fingers pressing firmly enough to tickle a little bit. And that made Catherine jump and spill her soda on the guy's shirt – which led to her having to apologise again, and to him keeping hold of her for even longer.

  She was being thrust about by the lurching of the train and being forced against him. His hands were moving upon her body. His thumb was pressing right up under her right boob, and his other hand was squeezing her hip, with his long bony fingers kneading her bottom a little bit.

  "You okay?" he asked, grinning down at her.

  "I'm fine, thanks," Catherine uttered in reply. "I'm so sorry about your shirt, though."

  "So, you're travelling alone, yeah?"

  "Uh huh. It's fun so far."

  "Yeah, good…. Do you smoke?"

  "Um – no thanks," Catherine returned politely as he offered her a cigarette.

  He had also released her, so she moved along, but as she did his hand lowered and he gave her a little pat on the rump. She glanced back and smiled out of confusion, and he grinned again and winked.

  Falling back over the legs of the woman into her window seat, Catherine giggled to herself. She just had her bum squeezed by a man who must have been at least 35. He looked like a business man too. He wasn't some scumbag lowlife. He was dressed in a suit, and she could see him back in his seat with his phone and laptop, obviously doing something important.

  She suddenly saw herself as the wife of a man like that. Not just a supermarket checkout chick, but a serious, attractive woman throwing dinner parties and stuff. It was a fantasy Catherine indulged for a little while as the train clanked along and the guy kept looking back at her. He was two rows ahead with an aisle seat. The one beside him was vacant, as were many of the seats in the carriage after about a third of the journey.

  Catherine kept blushing and smiling every time the guy caught her looking. Then after a while longer he went for a walk again and she assumed he was smoking, but he was gone for longer than that.

  Eventually curiosity got the better of her and she decided she needed some chips and another soda. She edged her way to the end of the carriage and looked around into the next one, and there he was sitting on the same window ledge with a hot dog and a beer.

  She steeled herself to walk by casually, but the train was still lurching, and she was being tossed from side to side. Then when she tried to squeeze past him he swayed against her and touched her sweater with his ketchup dripping hotdog.

  "Oops!" he said with a grin.

  The mark was on her breast, and he pulled out a handkerchief like he had it planned. "Sorry about that," he said, and he started dabbing at the ketchup.

  Catherine stood still and watched his hand move. Her nipple had firmed and was even prominent through her big bra. He was holding her sweater with one hand and wiping with the other. The stationary hand was sort of cupping her breast, and his bony fingers were pressing in, feeling her a little bit.

  "Do you have another sweater? You might have to take this one off and rinse it."

  "I have another top in my bag," Catherine answered, as if she would do as she was told.

  The train then lurched severely, and she was pinned against the wall with the guy's hand covering her breast, and he massaged it and pinched her nipple quite deliberately.

  "Don't!" she said, wriggling away from him but meeting his grin. "You can't just do that,” she challenged playfully.

  "Sorry," he said, though he was obviously not sorry at all. "Why don't you go and change, and I'll give you some money to buy a new sweater to replace that ruined one."

  "But I ruined your shirt – so we're even, aren't we?" Catherine’s confidence was up. She was feeling very flattered to have captured the interest of a mature man. "I'll go and get another top," she said, and she went back to her seat.

  The lights had been turned down for people to sleep, so she had to go by feel. She pulled a top from the bundle of clothes in her bag. There were only a few tank tops to choose from anyway, as that's all she had packed. She took it back and squeezed past the guy quickly before he could grab and tickle her. There was one other man there smoking who was from the seat behind Catherine's. She met his look and blushed as she sneaked past and into the bathroom.

  The train stopped while she was in there, making it easier to get changed. She pulled off her sweater and rinsed the stain, which would be fine. She then slipped on the tank top and looked in the mirror, horrified. It was a top she usually wore with a bikini, and the cut under her arms revealed the big thick bra strap as well as the side of the cup. There was no way she could go out there dressed like that.

  She checked her sweater, but it was half wet and the stain was still prominent. She then looked in the mirror again and turned this way and that, trying to convince herself it wasn't that bad.

  "Oh, God no," she whined under her breath as the train jolted into motion again.

  She then took a breath and pulled off the top and bra. Then she put the top back on braless and checked in the mirror to find that apart from being quite revealing, it didn't look too bad at all. From the side her breast was visible – the full side of it and very obviously, but her nipple was covered.

  She wrapped her bra in the sweater and took another breath. Then she opened the door and stepped out to find the guy from the seat behind still there smoking. He looked straight down at her chest, and she froze for a second and just blushed. He met her eyes again then looked back down, and she kind of waited while he had a good look. Then she squeezed past and approached the other man.

  He smiled as he looked up from her breasts. She smiled back at him and tried to quickly duck past, but he caught her around the waist.

  "What's the password?" he said to her, his long, bony fingers pressing into her side and making her squirm and giggle.

  "There's no password," Catherine laughed, b
ut he held her there.

  Then his hand lifted and closed over her breast, so she clutched at his arm, but she didn't say anything. A warm rush of excitement coursed through her. His big, strong hand covered her little boob.

  "Sure there's a password. There's always a password when you need to get by," he teased, and he wrapped his other arm around her from behind and closed that hand over her other breast.

  He was feeling them both and playing with her nipples. Mostly it was just through her top, but his fingers were reaching beneath her arms, and he was feeling her in through there as well.

  Catherine was holding his arms, sort of pulling at them but not really trying. She was watching the other man who was standing there staring, and when his eyes lifted and met hers she couldn't look away. All she could do was blush deeper at the fact that one complete stranger was watching another stranger feel her up.

  Suddenly she snapped out of it and wriggled to get away. "Stop it!" she said to the guy, and she squirmed from his bear hug and pushed him to arm’s length. His expression had changed from playful to quite serious, and he still had hold of her wrists.

  "Don't," she implored of him that time. "Let me go, please?"

  He nodded and gave another of those little winks as he released one of her arms, with his eyes lowering to her breasts again and his smile returning before releasing the other.

  8

  Catherine returned to her seat to find the woman gone and only four other people still there seated toward the back of the carriage. She tucked her legs up and closed her eyes to sleep. Then some time later she woke to the feel of a hand on her breast again.

  She didn't move or turn to see who it was. She could tell by how bony the hand was. She remained facing the window and pretended to be sleeping while he felt up under her top and softly massaged her bare breasts that time. He was feeling both and playing with her nipples – making her belly tingle and her heart thump.