I, Spy Ch. 02

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Jess gets what she wants. James spies on mom.
23.4k words
4.81
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Part 2 of the 4 part series

Updated 06/08/2023
Created 01/24/2018
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ladidai
ladidai
177 Followers

The end of Jessica Sullivan's second semester at college hadn't turned out the way she planned. Sure, there were classes, new people, and parties but after going home for spring break there was something else always at the back of her mind. And at those parties, it always found itself front and center, drawn out by the watery beer and plastic handles of liquor.

She had never been one for one night stands and she still wasn't but she found herself drawn to the guys who felt big as they ground their crotches against her ass. She would have rolled her eyes at them normally but something had changed inside of her. A couple of times when they weren't the usual college jackasses, she even let herself be pulled into an empty room but she was always disappointed that they never measured up to what she truly wanted. The few guys were almost as disappointed as she left them holding their own cocks.

The thought of the biggest, thickest cock she ever saw invaded her mind even as the largest cock she had found at school filled her sight as sighed in disappointment again. She didn't dwell on why she never did anything else but look but her mind always flashed to her brother's face as though it hoped he had snuck out from home and to her school. While the mental intrusion was bad enough in her drunkenness, it started to consume her idle mind the rest of the time. Looking for something to occupy her mind, she studied harder than she had ever before. Her professors were surprised and encouraged her to keep up the good work.

If only they knew why.

Still, classwork could only take up so much of her time so she looked for new activities on campus. Most of the ones she could join were the ones where you sat around talking about whatever subject the club was organized around. She didn't want that. She got her fill of sitting around, talking, and thinking with her renewed focus on class. Her mind had its distraction, now her body needed one. When a spot opened up in the intramural ultimate Frisbee league, she jumped at it.

Since quitting cheerleading, she had gotten pretty lazy about exercise and the first few sessions with her new team had her bent over, gasping for breath. That made her realized she needed to get back in shape. Helpfully, the campus gym was in the same quad as her dorm building. Her hand-eye coordination had never left her, and in a couple of weeks she was the best player on her team, dragging them to a respectable finish in the league. Seeing the final results made her happy but the league finished three weeks before the semester did, leaving her with her thoughts again.

It got worse when on a drunken night two weeks before finals her friends again pleaded with her to show them her party trick again. She had refused their multiple earlier calls, thinking that separating action and thought would help her control her mind but she must have had one too many drinks that night. Her friends whooped and hollered as she pushed the thick, rubber cock into her mouth then throat. They begged her to do it again then again then again, all while they howled with laughter and cheered her on. At first, their loud enthusiasm annoyed her but when the rubber balls hit her lips for the fifth or sixth time she let out a soft moan and rubbed her thighs together, now glad their excitement masked her own. She forced herself to stop much to their disappointment then threw the spit covered cock at them.

If she was honest with herself, it felt fantastic for her throat to feel so full, so fantastic that she bought herself a duplicate 10 inch dildo. Unlike the ebony one her friend had, she took way too long in picking the color that came closest to what she saw in her mind's eye. At first it quieted the urges but soon the thoughts quickly came back even worse. The dildo filled her throat and pussy and teased her ass but the cold feeling when it was inside her was worse than the emptiness when it wasn't. Besides, she could never get enough leverage on its length to fuck herself as she wanted, as she imagined the strength the person could fuck with.

The night after her last final, she walked out of a party before she could find herself in an unfamiliar room again. Nothing there would have satisfied her. Only what was back home would, and as she breathed in the summer night air, she decided she would be satisfied.

XXX

James Sullivan couldn't help but be disappointed when his sister came back from college. He felt a little guilty for feeling that way but now that she was home mom had made it clear that they couldn't do anything unless they were absolutely sure where she was going and how long she was going to be gone. They had come so close to being caught the last time Jess was home. If it weren't for the motion-sensing lights in the back yard, his sister might have found them lying naked wrapped in each other's arms in mom's bed on the verge of sleeping. After that close call mom put her foot down.

After almost two months of complete freedom, Jess was unknowingly torturing him by just being around. He could feel the resentment build inside him which he had to hide from her, and mom, but in the past two months he had grown used to waking up with his cock in mom's throat and falling asleep with it in her pussy. Going from having sex multiple times a day to only jerking off once during his morning shower and in his room at night was driving him insane. It didn't help that Jess had taken to wearing shorts and camisoles around the house. Or maybe she always had and he never noticed because she was his sister.

Maybe fucking mom had made him see just how hot his sister was?

It kinda made sense after he thought about it. Seeing one family member as a sexual creature made him see another family member in the same light. Soon, it wasn't just mom he fantasized about during his daily shower sessions but also his sister's full lips, bigger tits, and thicker ass. His fantasies about Jess took on a different light though. With mom, he knew what she liked, what she felt like, how she tasted, how she sounded. With Jess, his imagination ran wild which was a problem when it happened while he was in class and an even bigger problem when it happened at home.

In reality it was a combination of the two. Jess had always worn shorts and camisoles around the house. Her camisoles had grown shorter, exposing her midriff when she reached up to grab things. Her shorts tighter, wrapping her firm ass in a second skin. All in hopes to draw her brother's eye. She had also stayed home more often this break with the excuse of missing them both in the hopes of hampering their activities. The teasing seemed to be working. She had caught James staring at her a couple of times. He always quickly looked away like he was some shy high school kid, which he was when she thought about it.

For all her planned deterrence and teasing, she did the worst thing to her brother and mom without knowing it. Mom had gotten a room in a hotel an hour away the day after James's graduation. The plan was for him to join her later that day, giving them an entire afternoon and night to fuck each other's brains out. Jess spoiled it all when she claimed the other car, saying she needed it to go out with her friends and as the older sibling it was hers. She couldn't understand why her brother had gotten so mad, even after she offered to drop him off at his friend's house before she did her own thing.

James essentially stopped talking to her after that day, and it hurt her far more than she thought it would. Mom told her that he was being a silly boy and that he'd get over whatever was upsetting him. Mom also told him that but he didn't care. The thought of what they would do in that hotel room for a week since mom had told him about his graduation present filled, among other things, his mind. He couldn't believe Jess had screwed them over again. He especially couldn't believe mom could be so nonchalant about it.

Once her brother had graduated, he spent a lot of the day lounging around the house when he wasn't hanging out with his friends. Jess had hoped them being alone in the house would change his behavior but he didn't speak to her the entire day. The second day after his summer break started and he still didn't talk to her, not even thanking her for making their late breakfast. Jess decided to do something about it.

The next morning Jess cooked his favorite breakfast: pancakes with bacon and soft-scrambled eggs. More important than the menu was what she wore. She didn't know when her brother would be up but she waited until around the time he had come down the two previous days. Most of the pancakes were done with the bacon in the oven and she was moving the eggs around in the pan to make sure they would cook slowly when she heard a crash behind her.

James couldn't believe what his sister was wearing. Gone was the camisole. In its place was a tube top, and while she still wore shorts, they were so short the bottom curve of her ass cheeks peeked out of them. He had seen more of her skin when they were at the beach but this was the first time he had seen so much since he started thinking about her in a way a brother shouldn't have been thinking about his sister. The view distracted him so much he walked straight into one of the chairs surrounding the kitchen island.

"Fuck," he said as the pain from a stubbed toe registered.

Jess turned her head and smiled at him. "Just in time. Breakfast is almost ready." She hadn't turned all the way round, just twisting her hips to look at him so her waist and ass flexed in a delicious way. He looked back up at her eyes and she smiled even bigger. "Set the table?"

Forgetting to be angry at her, he said, "Okay."

"Mind if we eat at the island?"

He shook his head. While he set up two places at the island, he kept stealing glances at his sister, watching her body twist and flex as she cooked. Before long, his dick started to stiffen and he had to quickly finish so he could take a seat and hide his tenting shorts.

The reason why Jess wanted to eat the island was because it meant she could sit closer to him than she could at the dining room table. After she finished cooking, she took off her apron and had to hide a smile as her brother snuck looks at her breasts. She made it even harder for him to look away as she leaned over her plate to eat, exposing even more of her cleavage to her brother.

"So," she said, "hanging out with your friends again today?"

He nodded because he couldn't speak. He couldn't speak because his sister had finished her last bite of pancake and was now slowly licking maple syrup from her fork. Twisting the fork all around, she made sure to get every drop of the sweet liquid from the long tines and even pressed her tongue between the thin spaces between the tines in her search. He couldn't help but imagine her tongue doing the same things to his cock, which was the exact thing Jess wanted him to be thinking about.

"I'll do the dishes," he said. This was the standard division of labor at home but James had been eating slowly so Jess could finish before him and leave him alone to calm down. "You don't have to sit here while I finish eating."

The smirk and giggle she gave him made it seem like she knew exactly why he said that but that couldn't be possible because she would never think about him like that. His mind tangled into knots trying to reconcile his sister's actions and his absolute belief that she wouldn't think about him that way. His cock lurched in his shorts when she ran a hand along his back leaving the kitchen, and that meant he spent another ten minutes pushing his pancakes around the plate.

When he finally finished the dishes, he headed back to his room to jerk off to visions of his sister but as soon as he closed his door her door opened and she yelled for him to come downstairs. He let out a sigh and almost told her no, remembering that he was still angry at her for cockblocking him. Now she wouldn't even let him jerk off. But he knew she'd keep yelling at him and if he ignored her she'd barge into his room so he headed downstairs.

James's eyes almost bugged out of his head when he saw his sister standing in the kitchen wearing a string bikini. She had bought it from an Australian company that specialized in risqué clothing, mostly swimwear. The tri top bow peep bikini if she remembered correctly. Two small triangles made up the purple top, covering the front of her tits but leaving the rest of it exposed. The bottoms were the real scandal where a small triangle covered her pussy held by thin straps of fabric that wrapped around her hips then down between her ass cheeks. Her entire ass was left exposed, and if she bent over he'd be able to see the edges of her asshole.

"Hey, baby bro. I'm gonna work on my tan today. I know you don't want to talk to me but do you mind putting sunscreen on my back?"

All he could do was nod, and that earned him a grateful smile.

They went out to the back yard and she laid out a towel on the lawn then dropped down to her hands and knees, pretending to adjust the towel and giving him an extended look at her ass, before lying down on the towel. James thanked God that his sister was lying with her face turned away from him because his cock had started to tent his shorts as she messed with her towel, shaking her ass in his face.

"Did you hear what I said?"

"What?" He shook his head. "No."

"I said, 'I'm ready.'" He had done this plenty of times during family trips to the beach. There was no reason to be nervous as he dropped to his knees next to her left side. Aside from the fact that their mom would have killed her if she saw this bikini. "Make sure you cover me."

He started with her shoulders and back of her neck, hoping she wouldn't notice his trembling hands on her soft skin. As he moved down her back, she asked him to undo the string holding her top up. No tan lines of course. He squeezed out a few lines of sunscreen across her back and rubbed it into her skin, making sure to cover her with the white stuff like she asked.

Why the hell did she have to phrase it like that? It only made him think about covering her with something else besides sunscreen.

When he started on her left side, he swore she rolled over to her right a little as his hands moved up closer and closer to the side of her tit. It was like she wanted to expose herself to him but he had to have been imagining things. He wasn't imagining things. She knew exactly what she was doing as her untied top only hung loosely from her neck and more and more of her tit filled his eyes, hoping he would see it for the invitation it was.

His fingers stopped short and she almost let out a frustrated moan. She almost let out another one as his fingers trailed across her back to reach her other side. He had been planning on moving over to the other side of her body when he needed to do her right side but the idea that his sister wanted him to see her tits, along with the desire to touch her skin again, fogged over his mind. The reason he didn't want to lean over tented his shorts, and as he leaned over, grazed her back.

Even though his dick was encased in a pair of shorts, a bolt of pleasure shot through him when it touched his sister's back. It had been so long since something other than his own hand had touched him, and though he knew it was wrong, he couldn't help but graze it against her a few more times. Jess was enjoying the feeling of her brother's hands on her skin so much she didn't notice the pressure against the small of her back for the first few seconds. When she did notice, and realized what it was, she let out a gasp. The sound made James realize his sister could feel what he was doing and he jolted away from her, falling back onto his heels.

Jess looked over and her eyes locked onto the obscene tent in his shorts as her brother said, "Oh, shit. Sorry, I—"

"It's ok," She said as she rolled over and sat up.

No longer tied, the triangles of her bikini fell in between her breasts. James had never laid eyes on a pair so perfect, except for mom's but they were perfect in different ways. Being bigger than mom's, they hung ever so slightly as if they were begging for him to lift and squeeze them. Her nickel sized nipples were a couple of shades darker than her honey colored skin, and they looked pretty hard. But maybe they always looked like that. What really gave her away, though, were the goosebumps on her areolas and the rest of her tits. There was no mistaking what that meant because mom's tits looked the same way when she got turned on.

James was too panicked and stunned to process the details his eyes saw. He had to dragged his eyes away from his sister's tits, hoping he hadn't looked too long when in reality it had been just a few seconds, and found her staring at his shorts, her mouth open and tongue resting on her bottom lip. He had to stop himself from thinking that she was in the perfect position for a cock to be shoved into her mouth.

"Jess, this is wrong."

"Says the guy who got hard putting sunscreen on his big sister."

"This is just...a natural reaction."

Jess finally looked at him. "A natural reaction like fucking mom?"

"That's not—" James shot up to his feet. "I don't know what you're talking about."

She rolled her eyes. "I can always tell when you're lying, baby bro. Besides, I saw you two fucking when I was back home for spring break. And holy shit, were you fucking." As she talked, her brother stumbled backwards and she stood up to follow him. "At first, I freaked out when I saw mom sucking your cock, thought it was the most disgusting thing ever. But I couldn't stop watching. Then, after I saw you fuck mom, I couldn't stop thinking about your long, hard cock.

"I tried so hard to not think about it. Frisbee, drinking, studying. Do you know how much better my grades got because I tried to not think about your cock?" A ridiculous rhetorical question, but he shook his head anyway. "None of it helped. I couldn't stop seeing your cock in mom's throat. Do you want to see your cock in my throat? Because I want to feel it."

She ran a hand down the side of her throat as she asked her last question. Her brother's eyes widened. She grinned.

"I couldn't stop thinking about you pounding mom from behind. I couldn't stop imagining you pounding me from behind. Do you want do pound me from behind? Or me riding you until you pump me full of cum? How about on top of me with my legs wrapped around you? Or bent over until my knees touch my shoulders? I'm really flexible. I was a cheerleader, remember?"

His eyes slammed shut and he tried to stop himself from imagining her sister's words, as if he hadn't imagined all these things and more during the past few weeks. Throughout her teasing speech, he had been stumbling backwards out of shock and fear. With one more step, he bumped into the back of the house and almost fell down until his sister slipped an arm under his armpit.

"Were you thinking about filling your big sister with your hot, hot cum until it spilled out of her cunt? Is that why you tripped?" she asked softly, her lips grazing his ear. He groaned. She grinned, knowing the prize would soon be hers. "Were you thinking about how good it would feel to have your cock in my throat? In my pussy?"

James, in fact, wasn't thinking about filling his sister with his cum. His mind was having a hard time processing the facts that his sister knew about him and mom and that she wanted fuck him. Her words, exciting as they were, only created fuzzy visions in his mind because he never thought this was possible. At least until her lips grazed his ear. Lightning shot through his mind and body. His cock, already past half hard, throbbed as it filled out further. His mind, unbelieving of his sister's words until now, snapped into focus.

ladidai
ladidai
177 Followers