Sweet Catherine's First Experiences (Unprotected Book 1)

by Matt Coolomon

  She maintained the pretence of sleep for a while, but then he started feeling for the top of her pants and found his way underneath the waistband. He felt his way down to the top of her panties and slipped his bony fingers underneath.

  At that point Catherine couldn't help squirming a bit. She turned her body slightly, allowing him better access to her. His fingers then reached her clit, where he began rubbing. He was opening her pussy lips and pressing in right on her little button, so she parted her legs further for him.

  He then reached underneath and pushed a long, bony finger up inside of her, and as he did that he took her hand and placed it on his penis, which was also long and bony, although it was actually hard and soft at the same time, and really hot.

  He was alternating between rubbing her clit and fucking her with the length of his finger, and he was humping while she held his dick, moving her hand back and forth – like she knew boys liked.

  She was hoping she was doing it right, and that was distracting her from what he was doing – which felt nice and all, but before she reached one of her orgasms, she felt his dick swell and begin to throb.

  He had arched his body up, and she could feel the pulses of hot fluid slurping onto her belly. He was holding still with his finger all the way inside of her, and she suddenly felt young and inexperienced, and she didn't know why, but she decided to pretend to have an orgasm.

  It was as if she had failed if she didn't have one – as if she was too young and not woman enough to get off like that.

  In any event, she moaned a little and squirmed down on his hand like it was really happening the way it did when she was alone in her bedroom. She could feel his semen running between her breasts and dripping from her neck and side. The train was stopping, though, and her lover quickly gathered his laptop and bag and departed the train, leaving her lying in his cum and feeling completely confused.

  The train only stopped for a moment then jolted into motion again. Catherine was wiping at her chest as best she could with her hand. She was thinking of going to the bathroom and cleaning up, but suddenly the man from the seat behind sat down beside her and immediately groped her breasts. He was rough and forceful, and she was petrified as he took her hand and shoved it inside the fly of his pants. He lifted her top and leaned right over to suck on her breast, but suddenly he was gone and there was a huge thumping sound.

  Behind him was another man who punched him again and sent him flying backwards into the aisle. When he got up and turned to run, the guy booted him and sent him sprawling face first that time, telling him to fuck off.

  "Are you all right, miss?" he asked Catherine.

  "Uh huh," she swooned. He was a huge, powerful man, and she was tingling all over – just about having that orgasm after all.

  A woman appeared beside him. "Are you sure you're okay?" she asked. "Do you want to come to the bathroom and clean up?"

  It seemed they were husband and wife, and Catherine was just dumbstruck. The wimpy scumbag who had just groped her was forgotten about, and the other guy wasn't much better, she decided.

  "Come on let's get some tissues and see if we can clean some of that off you," the woman said, taking Catherine by the hand.

  The man led off toward the bathroom in case scumbag was still hanging around. Catherine followed along with his wife, and with that impish, mischievous little grin lighting up her face and with her pretty green eyes completely star struck!

  9

  After cleaning up, Catherine slept for the rest of the journey with her hero and his wife taking the two seats across the aisle and both of them smiling over every time she stirred to see where the train had stopped.

  In the morning when the train finally reached her destination, she thanked them and bade them goodbye. There she was greeted by her girlfriend Anne who led her to a rusty old car where her uncle was waiting. They got in the back seat together and left him alone up front.

  "This is Uncle Lester," Anne said, almost apologetically.

  Lester grinned back at Catherine and quickly looked her over. He was fat and sweaty with thick glasses and a bald head except for a frizzy grey patch over each ear.

  "Hi," Catherine said, offering a smile.

  "You can put your eyes back in their sockets now, Uncle," Anne said.

  "See – I told you," she giggled at Catherine. On the walk to the car she had warned that her uncle would like the fact that Catherine was braless under her top.

  Catherine had thought about putting a bikini top on after the lady on the train had helped her clean up, but she decided she liked the reaction from the two scumbags – or at least she liked the way they looked at her, and the way the first one had touched her. Though, mostly she just liked the way they had gone crazy over her, and she was enjoying the reaction of Uncle Lester too.

  She was sitting across on the passenger side, and he was constantly glancing back at her as he was driving, which was keeping her nipples hard and distracting her from what Anne was raving on about.

  Apparently there was a party to go to, and her brother Adrian was going to be there. He had been asking about Catherine and trying to find out if she had a boyfriend.

  "What did you say?" Catherine asked – her interest sparking at the mention of Adrian.

  Anne shrugged. "I told him to ask you himself if he wanted to know."

  "Well, I haven't," Catherine pointed out.

  "What about that guy from work – Des?"

  "He's not my boyfriend. He's just –" Uncle Lester was looking around, and Catherine met his grin with a little blush. "He's just a friend," she said to Anne.

  "Well, if you're going to hook up with my brother you can spare me the details. Yuk!"

  Catherine wanted to ask if Anne thought he wanted to hook up, but not with Uncle Lester listening.

  He smiled back at them and chuckled. "You can give me the details if you like. I won't mind.”

  "Eww. Don't be an old sleaze!" Anne complained, but Catherine met his smile with another little blush.

  "I need to get changed if it's going to be a whole hour before we get there," she said to Anne. "It's too hot in these pants."

  "I won't look if you want to get changed back there," Lester offered quickly.

  "Yeah – you wish!" Anne shot back at him. "Can we stop at a gas station soon?"

  "We'd have to get off the expressway. That'd be another half hour round trip to get back on it."

  "I can do it without anyone seeing," Catherine said to Anne. "I can put my skirt on over the top and then take these off underneath."

  "There – you see," Lester declared. "Nothing to it."

  "Well, go on then!" Anne said, as if she had to give her permission or something.

  Catherine's bag was on the front seat. She reached over and got a skirt out of it, making sure Uncle Lester didn't see her bra or any other intimates. Then she pulled the skirt on and undid her track pants underneath. She tugged them down with Uncle Lester watching back over his shoulder, and she had to lift her bum to do it. She wriggled the pants down past her knees and pulled them off her feet, all the while keeping her skirt in place and her knees together.

  10

  Lester had gotten a glimpse of her little white panties at one point, but he was more pleased with the view of her tits. He had been checking them out the whole time and enjoying the way they were pressing against the thin fabric of her tank top. Then as she had reached over to put her pants in her bag, he saw a nice firm little nipple through her arm hole. Her top was being stretched and distorted against the seat she was leaning over, and the arm hole was gaping and exposing her young titty completely.

  Then when she sat back down chatting with his niece she had her legs swayed towards him, and he actually had a nice view up her skirt. He had to look quite distinctly to take advantage, but he noticed she didn't seem to mind. She just had a cute little blush that deepened a bit each time he looked down at her legs.

  This was going to be an interesting weekend, Lest
er decided over the course of the hour drive back to his villa. He was ten years divorced and not getting much action. He liked living near the beach because of the hot bikini girls, but this was the first time his unfortunately unattractive niece had actually brought one home to stay.

  "Come on, I'll show you our room." Anne took Catherine's hand and led her inside. "It's just you and me. My brother's renting a house with his friends right on the beach. We can go next door and use the pool anytime we want, though."

  It was a small villa – just the two bedrooms and a basic layout for kitchen, bathroom and living area. It was tucked away behind a huge waterfront mansion where the pool was that they could use. That was owned by a very friendly novelist who was there cleaning the pool when Catherine was dragged over to the back fence.

  He was a man of about 35 named Michael. He was married but his wife was overseas. He had broad shoulders, a firm body and a nice smile, Catherine noticed. She was smiling back at him as he and Anne chatted.

  Another yummy man, she was thinking to herself. My god they're everywhere!

  Or perhaps she was just noticing them everywhere at the moment.

  *

  There was something in that – some sort of a glow young Catherine was giving off that Michael was picking up on as he tried to concentrate on what Anne was talking about.

  Michael had just gotten off the phone with his wife. She had been overseas for a month and wouldn't be back for another three. He had been married for only five years and usually maintained an appropriate, if a little forced, disinterest in the girls who used his pool. This one would be a challenge, he decided – just by the playfully sexy look in her eyes and a smile that was dangerously enticing.

  11

  The party that afternoon was at the house Anne's brother was staying in. It was right on the beach and open to anyone walking by as long as they brought their own drinks and food. Anne was all over her boyfriend, and Catherine ended up meeting lots of new friends and dancing and chatting all day. She also had a few drinks and had a constant buzz without actually getting drunk.

  Adrian had been around a fair bit, chatting with her and getting more and more familiar as the day went on. He had progressed from the occasional touch of her back or arm when he spoke to her, to holding onto her with his hand resting upon her hip and his arm sort of around her. He was definitely signalling to the other guys that Catherine was his. It seemed the hook-up was on.

  Catherine went with it willingly – excitedly in fact. He was the hottest guy there by far, and she liked how polite and courteous he was. When one of the other guys were involved he would carry on like a usual boy, but when no one was around he became more mature.

  The first time he kissed Catherine she was squashed on the end of the lounge with about four other people sitting on it as well. She was against the arm rest, and Adrian was sitting next to her. Then there was another girl and boy cuddling and Adrian's friend Brett was sitting on the end. He was watching, and Catherine actually maintained eye contact with him while Adrian was kissing her. He looked like the fat geeky boy who never got a girl, and she felt sorry for him.

  "I've got to go soon," Adrian said, coming up for a breath. "We've got monster truck rally tickets, and it starts in about half an hour."

  "That sounds like fun," Catherine said as he kissed her again.

  "I'd ask you to come but it's sold out."

  "Oh, no, that's okay. I'm really tired anyway."

  Catherine was tired, but she would have liked to go with him. Instead, she ended up leaving Anne there and going back to Uncle Lester's villa alone. Which was fine because she kind of liked Uncle Lester.

  Sure he was a pervert, but he wasn't sleazy about it. He was actually totally up front and made it fun.

  "So – any details for me about getting it on with young Adrian?" he asked, grinning, as soon as Catherine walked in the front door. He was kicked back on his couch with his feet up, watching television. His googly eyes looked so funny through his thick round glasses, and his smile was disarming. He was only joking but was probably hoping for some details just the same.

  "Well, he kissed me but he wouldn't take me to the truck rally," Catherine explained.

  "He wouldn't!?What's the matter with him?"

  "I don't know. I would have gone!"

  "Hmm. Maybe he's gay after all. I always suspected, being such a pretty boy."

  "No, I don't think he's gay," Catherine laughed.

  "Well, he's stupid, then! And anyway – come sit down and we'll see if there's something to watch."

  "Oh – thank you, but I'm really sleepy and I might just have a bath and go to bed if that's okay?"

  "Sure, love. There's clean towels in the linen cupboard in the bathroom. I'll keep the volume down."

  Catherine soaked in the bath for an hour with the effect of the alcohol wearing off. She had brought a satin chemise to wear to bed, and she put that on but didn't worry about the robe she had brought. Instead, she went out to say goodnight to Uncle Lester feeling naughty and with her nipples firming against the satin as she walked.

  *

  Lester noticed them as soon as she appeared in the doorway – little points in the shiny fabric. She was standing there wringing her hands in front, seemingly in thought over what to do or say. He looked down at her long slender legs and wondered whether she had on panties under her sleepwear. He contemplated that for a moment then lifted his gaze to her little titties again and finally to meet her eyes and embarrassed little smile.

  She approached and bent to kiss his cheek, and as she did he got a quick flash down her front and saw her young tits and all the way down to her pink and blue panties – they were soft cotton ones, nice and comfy for sleeping, he imagined.

  "Goodnight," she said sweetly, turning and walking from the room with a glance back over her shoulder and a cute little blush.

  *

  Catherine hopped into bed squirming and pressing her hand down between her thighs. She knew she had just flashed Uncle Lester, and she was tingling all over.

  She ended up rubbing herself to a warm little orgasm as she thought of that and remembered the guy on the train. Then she drifted off and didn't wake until late the next morning.

  Anne was at breakfast in the kitchen, and after eating they took towels and suntan lotion to the beach. They spent the morning there and didn't see any of the guys until after lunch, when the party was at the big mansion next to the villa.

  There were quite a few people from the beach party the day before, and Michael, the owner of the house, was sort of in the background chatting every now and then, but he never got undressed and went for a swim.

  Catherine ended up with another buzz from a few drinks, and she was being kissed in the corner of a room with a pool table where there were four other boys who had stopped playing to watch. Adrian was a bit drunk too, and he was getting carried away. He was biting her neck, and he started feeling her boobs. She maintained eye contact with the fat geeky boy again, and the other three started cheering Adrian on. She was only wearing a skirt and bikini, and he was rubbing her breasts so much that he stretched her bikini top up over them.

  She was then on display, but she didn't say anything yet. Her mind flashed back to the time she saw the woman from across the street being taken in front of her husband, and she let Adrian keep kissing and feeling her while the other boys watched.

  He rubbed his hand down over her belly and groped up under her skirt. "Yeah, go for it," one of them said, and Catherine felt herself blushing, but her head was woozy from the drinks and she just held onto Adrian's shoulder while he forced his finger up inside of her.

  She just watched their faces as Adrian fingered her. He was banging her hard and fast with his hand slapping against her, and a warm tingly feeling was building inside. What he was doing felt nice, but it was even more exciting with the other boys watching. They wouldn't have been able to see under her skirt, but they could certainly hear his hand slapping against her,
and her top was still stretched up over her boobs.

  Catherine found herself making eye contact with Brett again. He would look down at her breasts for a bit then look up again. And staring into his eyes made her orgasm build and build. It was almost there when suddenly Adrian lifted her up and kicked open another door. It was an office with a small couch, and he dumped her there and pulled down his shorts as he pushed the door closed.

  Catherine's orgasm was ebbing away unrealised. The guy knelt over her and forced his penis into her mouth. She didn't know what to do, but she knew enough to roll her lips over her teeth, and fortunately he started thrusting and it was just a matter of holding him away enough that he didn't force it into her throat – and to try and breathe when his belly wasn't squashing her nose.

  "Oh, fuck yes," he groaned and he started thrusting faster.

  His penis was getting bigger and harder, and Catherine had to close her hand all the way around it so it wouldn't go too far into her mouth. She also started licking it a bit and sucking on the big, spongy dome. Which just made him go even more crazy, thrusting and jiggling, then he was suddenly still and his penis got even bigger and harder. Then Catherine's eyes widened as the first pulse of his semen hit the roof of her mouth and squirted down into her throat. That made her gag a bit but he held her in place, and his penis continued to throb as more and more of his warm, gooey fluid flooded into her mouth.

  Catherine let it happen. She pulled back a bit and waited until he had finished. Then she closed her eyes and swallowed more deliberately, and she sort of sucked him a bit more and felt his balls – not really knowing what she was doing, but he seemed to be liking it.

  It was a really strange taste – kind of salty and yucky, but distinctly male, and in that way it was interesting. It was nice to finally taste a boy's cum. And even though her own orgasm had fizzed out completely, it was nice to see him standing there pulling his pants back up with a stupid grin on his face – obviously satisfied.

  "Fuck, I'm thirsty," he said, and he opened the door and walked out, leaving Catherine to quickly cover her breasts back up.