A Change of Scenery Pt. 02

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The struggle continues, but it works out in the end.
9.6k words
4.66
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35

Part 2 of the 2 part series

Updated 06/08/2023
Created 01/08/2017
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Chapter 7

Lazily Jimmy got out of bed at 10 in the morning on Saturday. He got ready for the day, trying to look better than usual. He wanted to impress Natalie; he kind of had a thing for her.

Jim played some video games in the morning until lunch time and had a meal with his mother and father. Worried he might be late; he rushed through lunch before heading out the door.

Being rather fortunate, Jimmy owned a car, it wasn't anything special, but it made him immensely popular with his small crowd. He stopped by Natalie's first, of course! He wanted to talk to her, if he had the guts, before the others ruined it all.

He was at Natalie's soon enough, and trying to seem casual and not too anxious, he sat in his car and honked the horn.

BEEP! BEEP!

A minute or so passed before the front door flew open and the girl of his recent dreams skipped out. Her brunette hair bounced with each of her skips, as did her boobs. Being a gawky teen, Jimmy couldn't help himself. Natalie wasn't the most bosomed girl, but to him she was perfect. Her perky B-cups jiggled as she slowed to a walk and she smiled to him. He smiled and waved, remembering to be casual.

"Hey!"

"Hey!" he replied, "ready to go?"

"Yup!" she said.

The two chatted very briefly, it was rather forced. Jimmy felt horrible about how things were going so far. They'd talk for a bit until they ran out of things to talk about and the conversation would end. Jimmy would try another approach but that died quickly as well.

Thankfully, they arrived at Sammy's. Jimmy sighed in relief as at least another person may liven up the conversation. Sammy was another brunette, quite pretty, but not as pretty as Natalie. She had bigger boobs, easily a C-cup and wider hips. Unlike Natalie, Sammy was short at 5 feet 3 inches. Natalie wasn't tall by any means, standing at 5 feet 6 inches. Jimmy had to sneak a peek at Natalie as Sammy entered. He managed to catch a glimpse of side-boob from her dress. Unfortunately Natalie caught on to Jimmy and was none too pleased by his spying. He blushed and turned away before heading to Tony's.

The ride to Tony's was much livelier, though more so between the girls than it was between the girls and Jimmy. He didn't care, the fact that he was even hanging out with girls was an accomplishment at that.

In 10 minutes they were at Tony's and he piled in the back next to Sammy. Tony was a loud kind of guy and almost always needed attention, something Sammy fought over.

It was at least another half hour before they got to the mall. Natalie, Sammy, and Tony talked amongst themselves while Jimmy chimed in every so often just to make sure they knew he was there. The gang arrived at the mall and went straight to the food court. They were all hungry despite already having eaten lunch. But most of them, like Jimmy, ate a quick one before getting ready for their get-together.

Much like the car ride over the four chatted, this time Jimmy was more vocal. He tried talking with Natalie and had better success, maybe the extra moral support was what he needed. They talked and talked and eventually decided on a little bit of shopping, for the girls. The guys had no problem as they'd be able to talk with each other, though Jimmy wanted to use the time to talk with Natalie as well.

After second lunch the gang walked about, the guys following the girls around. Again, Jimmy had more success with Natalie. She wasn't the most bubbly girl, like Sammy, but she was relatively easy enough to get along with. She didn't have much of an attitude, though she knew she was pretty. Sometimes her ego did get to her head which turned Jimmy off, but those were few and far between.

After their fourth store Jim really got to know Natalie outside of school. He asked a lot of questions and she happily answered, though he was surprised she didn't ask too many about him.

A few more stores and the girls felt they dragged the guys around enough and the four settled on a movie after dropping their things off at Jimmy's car. The guys wanted an action movie and the girls wanted a romcom. The girls won so the guys escorted their respective girls to the theater. Jimmy sat in between Natalie and Sammy, leaving Tony on the end with Sammy.

The movie really couldn't have gone better for Jimmy, Natalie had kept a hand on his thigh almost the entire length of the film. He was too nervous himself to do anything, but was glad when the movie was over. The four were out, with Natalie giving Jimmy a smile and wink.

By now it was around dinner time and the whole gang agreed to stay at the mall and eat there again. They chatted some more. Natalie really seemed to open up to Jimmy now, she was asking questions about him and he was answering happily. He felt really good about himself afterward, feeling a real connection between him and her.

The night finally came to a close as did the mall. The gang was sad that it all had to end, but they agreed to hang out the next day as well. Jimmy took them back to their homes, dropping off Tony first then Sammy. She lingered a little, chatting with Natalie and Jimmy, before she pranced away. Jim was glad he was alone again with Natalie, she seemed glad too. She kept smiling at him and blushing. They arrived at her place and she gave him a light kiss on the cheek, "Have a good night!" blushed Jimmy.

"Thanks, you too!" said Natalie. She got out and seductively swayed her hips as she walked away. Before entering her house, she waved again and left Jimmy to himself.

Jim drove himself home, thinking about Natalie the whole way there. She really was a pretty girl. She had a natural olive skin tone, probably Greek or Italian he thought. Her brunette hair was kept shinny and soft, he imagined. He tried to sniff her hair when he got the chance in the theater, trying to be as subtle as possible. She smelled like peaches. He did regret never touching her soft skin, he was partly glad too. He didn't want to seem too anxious, that'd be bad, he thought.

He got home and ready for bed. He did his nightly routine, though this time thinking of Natalie. Before making it to the finish line he screamed her name into the pillow before spilling his seed into some tissues. He drifted off to sleep with his cooling semen sticking to him.

Chapter 8

The next day Jim woke up with a little spring in his step. He showered, ate breakfast, and got ready for the day. Like the previous day, Jimmy left after lunch and went to pick up the others. He again stopped by Natalie's first, they chatted on their way to Sammy's and then to Tony's. It was a nice day and the four decided on the park for their afternoon.

After finding a parking spot the gang got out and walked around the area. They talked amongst themselves, not just between their respective interests. By the end of the afternoon Jimmy learned a lot about Sammy in addition to Natalie. He already knew a lot about Tony because they had hung out before and on quite a few occasions.

Not once during the weekend did Jimmy think about Bridget and his problem with her. He was just too focused on Natalie. Sammy and Tony fought, between the two of them, for the most amount of talk time. Sammy won, making sure she was in almost every conversation or having some quip about something. Jim thought she was a little nosy at times but that was just her bubbly self, he still liked her as a friend nonetheless.

Seeing as the four were having school the next day they ended up cutting their day short. Jim drove his friends back home, once again dropping Natalie off last. She kissed his cheek again before turning and skipping back home. Jimmy drove himself back home, thinking about Natalie again.

That night Jimmy fantasized about Natalie and her possibly being his girlfriend in the near future. With another sticky pair of tissues, Jimmy fell fast asleep thinking about her.

********

Nearly a month passed before Jimmy finally brought up the courage to ask Natalie out. Every day he met Bridget to do whatever she needed in the mornings, lunch, and after school. She'd done quite a number on his ass and was finally used to the punishment. Jim and Molly got to be friends, in a weird sort of way. They were sex buddies, but not in the way most people thought about sex buddies. It was pretty customary for the two of them to be with Bridget, servicing her every need. Molly and Jimmy were actually good friends now and talked often whenever they might see each other.

Jimmy finally had a good group of friends in high school for the first time in his life. He was partially glad he moved here and partial not, for obvious reasons. Natalie, Sammy, and Tony were easily his best friends and he got along with them all very well. Today was the big day, he'd ask out Natalie.

Jim had it all planned out. After school he'd do whatever Bridget needed and then meet up with Natalie, he'd already texted her to see if she was available and she was. She agreed to meet him at her place at 5:00 pm.

His morning was not unusual. Bridget, Jim, and Molly were all in a closet. Bridget had Molly bent over a bench and she was ramming her cock deep inside Molly's asshole. Molly hated it when she was taken like this and in the butt, but she was powerless. Molly screamed and screamed, as she was being raped. As was usual with Jimmy, he tried to hide his erection but found it difficult.

"Come on baby!" Bridget moaned. A few more hard, quick thrusts and she was unloading her semen deep inside Molly's bowels. Molly cried on the bench as she felt Bridget's seed spill into her. She'd never given herself without protection before and here Bridget was deflowering her most private area and ruining it by leaving her white creamy load.

Bridget dismounted from Molly and stepped back, admiring her work. She looked over at Jimmy and could see his erection through is jeans. He tried hiding it but Bridget knew better. She'd caught him numerous times with an erection from whatever act she was performing on Molly. She smirked to herself, I'm basically providing him live porn!

Bridget had a great and evil idea pop into her head just then.

"Get up," she commanded.

Jimmy did so. His erection strained against the inside of his trousers. It was painfully obvious he was horny and Bridget used this to her advantage. She beckoned him to come close and he obeyed, just stopping in front of her. Bridget unzipped his pants and let them fall to the floor. She pulled on his shorts and they fell as well. "Step out," Jimmy did so and stood half naked below the waist. This was odd of her; usually she made him keep his pants on when she fucked him.

There was a pause.

Jimmy looked to Bridget for directions. A huge grin, an evil looking grin, appeared on Bridget's face. He knew something was up, but what?

"Fuck her," was all she said.

Jimmy stood there blankly...

"Fuck her ass!" Bridget commanded more forcefully.

Jim looked to Molly. She was still bent over and still crying. White goo was spilling out of her asshole. She too looked to Jimmy, having heard what Bridget wanted. Jim and Molly made eye contact, and without even saying a word Molly understood, Jimmy was sorry for what he was about to do.

Bridget was about to open her mouth and yell out at Jim, but his movement towards Molly shut her up. She grinned again, not really believing that she had this much control over both her slaves.

Jimmy was right behind Molly now. He really didn't want to and turned to Bridget. Her expression said it all; he wasn't going anywhere unless he did what he was told. He really wished he carried condoms with him, but knew Bridget wouldn't have even let him use it if he had.

Jimmy's eight inches rested along Molly's wet slit. He could feel her warmth as could she. "I'm so sorry," he whispered.

"COME ON!" roared Bridget.

This startled the two, but not for long. Jimmy grabbed his pulsing cock and wet it with his hand. After what Jim thought, was enough 'lube' he pressed his cock against Molly's slightly open hole. Molly grimaced, having seen his cock before she knew it would be more painful than Bridget's. His wider girth and longer cock pressed at her opening. Jim slipped into Molly quite easily but still elicited a grunt from her. Having never had sex before, Jimmy was shocked to how good it felt. Molly's asshole clung to his cock like an extremely tight, hot fist.

Molly tried squirming away once she felt Jim's cock press against her inner sphincter. Bridget had a little trouble getting in but Jim was almost too big for her, she screamed as he broke through her inner hole and finally bottomed out. Bent over and in pain, Molly lied there quietly crying to herself.

"FUCK HER NOW!!" screamed Bridget.

Damn, thought Jimmy, she has no patience whatsoever... "I'm so sorry..." he apologized again. He pulled out and gently pushed back in.

"Harder than that..." Bridget coldly suggested. Jim felt her eyes on him and Molly and knew he had to perform for her. He regretted what he was about to do, having lost his virginity and was impaling his friend. Jim pulled back out and rammed his hips into Molly. She screamed at the sudden thrust and began sobbing again.

It felt just too good for Jimmy and he began pummeling Molly's little asshole. Out of the corner of his mind he could hear a light whimpering. At first he thought it was Molly. But, from what he could hear, Molly didn't seem to be enjoying what was happening to her, understandably. On closer inspection by Jimmy he could hear the faint and unmistakable sound of a squelching sound. He was too caught up in the moment to really process this as his orgasm rapidly approached. Molly's asshole was just too good for him and he knew he wouldn't last much longer at this clip.

"Oh yeah..." came a groan from behind Jimmy. He had to see what was going on. He didn't have to turn far to see Bridget standing just behind him, which startled him, stroking away at her cock. She edged closer to him, standing side-by-side now. While still pounding Molly's ass Jimmy looked to Bridget's flailing hand. Her cock glistened with lube and the squelching sound now made sense to Jimmy.

"Fuck..." grunted Bridget. Rising on her toes Bridget leaned forward and unloaded her semen all over Molly's naked, jiggling butt. She stroked herself until the final droplets of her seed oozed out her mushroom, "fuck... that was sssooooo good..." she groaned again. This distraction was enough for Jimmy to regain his stamina.

But for whatever reason watching Bridget cum on Molly's butt was a huge turn-on for Jimmy and he regained his intense pistoning. Jim slammed his hips as fast and as hard as he could. Molly's screaming came back, but now it almost sounded like she was enjoying it.

Soon, Molly was squirming on the bench, her legs shaking. Jim could hear her breathing loudly. I can't hold out much longer... he groaned to himself. He didn't have to, Molly screamed, trying to cover her mouth with her hands, "MMMMMMMMMM!!" her whole body spasmed on the bench and Jimmy felt his trouser legs get damp.

"Wow! Look at that!" Bridget jeered, "You made her cum, and gush!" Jimmy couldn't believe it, in his first act of sex he made a girl cum. He was immensely proud of himself, but that was short lived. His balls tingled and he groaned as he coated the insides of Molly's asshole with his creamy cum.

Jim planted himself deep inside Molly and held there until his spasming cock stopped. He grunted and sighed, not believing he'd just done that. To this point in his life this was the single most rewarding thing sexually. Molly's asshole held Jim inside, seemingly not wanting him to leave the clutches of her soft warm cavity.

"That was great! See you all later!" Bridget was out the door and off to class. That just left Jim and Molly, who was still bent over and impaled by Jimmy's now softening cock. "I'm so sorry," he apologized again.

"Don't be..." she whispered. Jim pulled out and let his soft cock rest.

"Wait what?" he asked.

"After what Bridget did and then what you did... it felt nice..." Molly blushed, not really believing she was admitting she liked it. "You made me feel good..."

"Uh..." Jimmy thought for a moment, "but I practically raped you..."

"At first, yes, but it wasn't your fault."

"I still did it though..."

"Yeah, but the way you did it, you didn't want to hurt me..."

"Of course not, we're friends, I wouldn't want to hurt you," explained Jim.

RING, RING, RING!

The two heard the warning bell for classes and quickly finished their conversation. Molly forgave, and actually thanked Jimmy for opening her mind. Jim felt really weird about it all, despite her forgiveness. He tried to push it out of his mind as he thought about the rest of the day, and especially Natalie.

******

Lunch came and went. Bridget needed some much needed attention and Jimmy gave her a satisfying blowjob before leaving for the last set of classes.

Jimmy had been texting Tony and Sammy about what he was about to do. They encouraged him and wished him well. It gave him some more confidence as he was leaving for Bridget's. Hoping to get this over with as soon as possible Jim followed Bridget up to her bedroom.

Bridget had already rushed up to her bedroom while Jimmy lagged behind. He opened the door and turned around to close it. When he turned around again he was greeted by Bridget's naked body. She was already hard, her cock standing straight out, all seven inches of it. "Get over here and suck me off!" she said firmly but not too loudly.

Jim meandered his way and knelt right in front of Bridget. With no hesitation from his part Jimmy took her entire length. He had little problem now, having done this for a few months or so. "Oh that's a good boy..." Bridget moaned above him. Jim almost always kept his eyes closed, so he could never really admit to himself of what he was doing. But for some reason, he wanted to look at Bridget. He slowly opened his eyes and looked up. Jimmy was pleasantly surprised by the view he had. Above him Bridget was kneading her breasts together; it looked oddly feminine the way she was doing it. He watched, getting aroused himself, as Bridget fondled herself. She flicked her nipples and played with them, much as he imagined Natalie would do to herself.

Jimmy froze as their eyes locked. "I see you seem to be enjoying yourself down there!" she grinned. "Well maybe I should help you out. But be sure to make me nice and slick!"

Jimmy knew what was coming, so he made sure he did just as she asked. Without using his hands, as he didn't want them in the way, he slurped and made as much saliva as possible. "Greedy little boy, aren't we?" Jim slurped and slurped, making sure to over emphasize the gurgling sounds as well, he knew she liked it a lot.

"Okay, that's enough! I don't want to pop just yet!" Bridget pushed Jim away and smiled to him, "Take your clothes off... please..."

That was odd, thought Jimmy, she's never added a 'please' before. In a jiffy, Jim's clothes were off. He turned around to see Bridget turn around at the same time. She had a smile and patted the bed in front of her, "right here!" she sounded more cheery than ever. He crawled up her bed to the area she signaled. As if to ask 'here?' he looked to her. She smiled and nodded. She turned him just a little to the right and then winked, "perfect! Now I want to try something new!"

Bridget's cheerfulness was starting to disturb Jim, why is she so happy? Was it because I'm finally doing what she wants? He was right, up until about a week ago he'd resist to some extent, though less and less as the weeks wore on. I guess that could be it, whatever...

Bridget positioned him so he was kneeling, like in doggy-style but sitting upright. Bridget nestled in right behind him. He could feel her erection along his back and shivered in anticipation.