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The Temptation of Bobby

Tobey and Jennifer had always had a good relationship with each other. They had been together for at least a year now and he could imagine spending the rest of his life with her. Since Tobey was single he started exploring the club scene of Cincinnati and that is where he had met her. He had seen her across the room and felt that it was love at first sight.

Now, a year later, they were still together, but things had taken a turn for the worst financially when Jennifer lost her job because of cut backs. They couldn't afford the apartment that they were living in downtown, so they needed a roommate. His younger brother Bobby was looking for a place to stay and Tobey decided what the hell, he should help a brother out, right?

Tobey was a bit nervous about his brother moving in with them because over the years his brother had always been interested in the same women that he was. Since his brother was younger and more charismatic and “charming” than Tobey, he always ended up with the girl no matter what Tobey did in the past. But he thought that his brother would be the better man and leave Jennifer alone.

The day that Bobby moved in, things were already tense between Jennifer and Tobey. She was frantically searching for another job and coming up empty-handed. Tobey tried to help by searching craigslist, want-ads in the paper, and any places online that he could think of. But after a while he gave up trying to help because Jennifer would always get mad at him and tell him she didn't need his help finding a job.

The knock on the door signaled Bobby's arrival and Tobey opened the door and hugged his brother tightly. Bobby and Tobey were about the same height, but being that they weren't twins, he was a bit cleaner cut than Tobey was. His stubble was neatly trimmed and his hair was spiked in the front short in the sides and back, whereas Tobey had a full beard and tended to keep his spiked in the front but longer on the back and sides.

Physically, the two of them were both pretty strong. Bobby worked out at the gym every day and Tobey hit the gym at least a few times a week when time permitted. Lately it was more because of the fact that he and Jennifer were barely talking.

“Hey, little bro, how as the trip from Washington?” Tobey asked, patting his brother on the shoulder. “Come on in and get settled. Jennifer is at an interview right now but she should be back any second.”

“The trip was great, man, but I'm tired as fuck. She getting a job finally?” Bobby asked, setting his large duffel bag down on the floor as he gave a look of approval at the apartment. It was a three bedroom and one room served as Tobey's office since he worked from home.

“Yeah, she works graphic design, it's just hard to find a job that pays as much as her old one. She worked there for five years. It was pretty cut throat when they laid her off.”

Bobby whistled, giving a nod of understanding. “Shit, man, that sucks. I'm going to hop in the shower, the plane ride was long as fuck and I need to unwind.”

“Cool, man, it's down the hall, second door on the right.” The first was a pantry that was stocked full of food.

“Thanks, bro. I appreciate you doing this for me, man. You're the best.” He took a glance at a framed photo of Jennifer and Tobey hanging up in the hall and whistled. “Damn, is that her? She is one fine piece of ass. You done good, bro.”

Tobey just laughed it off and turned on the TV after he heard the shower running. A few moments later the door opened and Jennifer walked in and Tobey looked at her from the couch, admiring her beautiful form. She was a few inches shorter than Tobey at 5'6″ with dark hair and beautiful chocolate colored eyes. Her breasts were full and ripe, her hips shapely, and her figure had all the right curves to it. Most people would say she was average looking but Tobey would beg to differ.

“Hey, babe. Bobby is in the shower, I think. How did the interview go?” He noticed she looked passive, so he wasn't sure.

“I got the job!” Jennifer exclaimed, after a moment of awkward silence.

“Oh, thank God!” Tobey laughed and hugged his girlfriend tightly.

“Congratulations, Jennifer!” Both of them broke away from each other as they heard Bobby's voice in the room.

Tobey heard Jennifer gasp as she took in Bobbie's muscular form dripping with water with just a towel around his waist. He scowled at his younger brother and folded his arms over his chest, shaking his head. Was he doing this shit on purpose? He couldn't believe it had barely been five minutes and he was already half-naked in the living room in front of his girl.

“Sorry. I forgot that my clothes are in there.” Bobby pointed at his duffel bag on the floor. He held out his hand for Jennifer to shake with a smile. “You must be Jennifer. Tobey has told me a lot about you. It's good to meet you. Sorry about the half-nakedness.”

Jennifer laughed and shook Bobby's hand and Tobey noticed that her eyes were traveling all over his form, taking in his biceps and the trimmed happy tail going down past his waist but thankfully hidden behind the towel. “It's nice to meet you, Bobby.” She said it a little breathlessly and Tobey had to resist the urge to roll his eyes. This was going to be a long night!

Bobby gathered his clothes out of his bag. “Oh! Let me show you to your room. Tobey, why don't you order Chinese for all of us?”

Tobey sighed and gave a nod. “Yeah, of course. We need to celebrate.” He eyed his brother in a way that told him if he fucked with his girl, there was going to be hell to pay.

Jennifer followed Bobby to his room which was the smaller bedroom at the end of the hall. She walked inside with him and her eyes traveled over his muscular back and she bit her lip, feeling an ache in the pit of her stomach at the sight of him. “So, Bobby, was your flight okay?” She tried to distract herself from what she was feeling by making small talk but her cheeks were flushed and she felt like it was way too hot in there.

Bobby had no modesty so he took his towel off and heard her gasp at the sight of his cock. It swung proud between his legs and even when it wasn't hard it was a good seven inches long and dangerously thick. Women always flipped out when they saw how large it was but he was used to the reactions he got when it was first seen by now.

“Yeah it was great.” He winked at Jennifer and opened up his duffel bag, pulling on a pair of jeans and a t-shirt. “We're all friends here, right? I know you are Tobey's girlfriend, but I have never been ashamed of showing off the goods.”

Jennifer just laughed it off, waving her hand. “It's okay.” Oh my God! Her cheeks were red and flushed. Never in her life had she seen a cock that big. He was the size of Tobey when he was hard, but Tobey wasn't nearly as thick either. She knew that Tobey was above average, but Bobby was just way beyond that, and she found herself thinking about how that thing would fit in her and what it would feel like to be fucked by such a wonderful cock.

She felt ashamed that she was so drawn to Bobby, and she had just met him five minutes ago. She had yet to meet their parents, and since they lived in Washington, it was hard for them right now financially to travel to meet them. The sight of him naked had been startling and surprisingly arousing. She loved Tobey and she loved his body but her brother was a temptation that she knew she was going to find hard to resist.

“Oh, so it's okay if I walk around naked more?” He asked, a teasing tone to his voice.

“I would have no objections to it.” Jennifer was horrified that she said it, but Bobby just seemed to laugh it off like he was used to having women saying things like this to him all the time.

“Don't let Tobey here you say that, darling.” Bobby winked and let his eyes travel up and down her form.

She blushed and found herself biting her bottom lip as Tobey's younger brother seemed to be undressing her with his eyes. Two could play at that game!

Jennifer took off her t-shirt so that she was in her black sports bra that she knew hugged her tits nice and snug. She stared into Bobby's eyes as she undid her skimpy shorts and wiggled out of them to show him her matching black panties. “I think a shower sounds really nice.”

She giggled as she noticed his mouth agape and she turned away from him and stepped backward so that she was behind her clothes and bent over. She didn't realize how close she was to Bobby when she did it and her ass pressed right into his bare crotch as she bent over.

She gasped as she felt his hands on her hips and his strong body pressing into her. She was helpless as she absently ground her ass into the monster that was his crotch, feeling that huge horse cock of his start to harden against her ass.

She knew she should move away but it was like her limbs were suddenly paralyzed. She felt those fingers digging into her hips as she rocked her ass up and down the hard length of his shaft, her panties starting to soak as she felt that hardness grinding between her ass cheeks.

She could hear her breathing getting harder as Bobby grew more bold and began gyrating his hips up and down, his thick cock slipping between the ass cheeks of her panties as they dry humped each other eagerly. She thought about how easily it would be for him to pull the crotch of her panties aside and fuck her right now, while Tobey was ordering Chinese in the kitchen. The thought had her so soaked that she knew she would have to change her panties.

She gasped as suddenly Bobby placed his cock so that it was between her legs, pressed against the damp crotch of her panties. Every time he moved she would feel that bare cock press against her clit through the junction of her underwear and the feeling was sending bolts of pleasure through every inch of her body. Before she was able to help it, she was rocking faster and faster against him, sliding her labia up and down the length of his thick meat as she felt herself approaching an orgasm fast from the clitoral stimulation.

She pulled the crotch of her panties aside so that she could feel that thick monster pressing direclty on her sensitive nub. Bobby groaned with desire and started gyrating his hips with urgency, every inch of him slipping up and down the outer limits of her slick pussy. Her juices coating his delicious dick allowed the whole length of him to slide up and down her crotch with ease and he began to pull her hips in his direction with each hard thrust of their thighs to increase the pleasurable friction that was driving them both toward release.

She threw her one hand over her mouth as suddenly her world exploded in ecstasy. Her juices splashed out of her cunt to coat the cock that was pounding against her clit and she soon felt Bobby shift behind her and stroke his cock furiously as he aimed the tip at her clit and began to cum all over her pussy. The feeling of his hot sperm coating every inch of her outer labia had her cumming again in what seemed like a series of mini-orgasms, her whole body shaking and trembling as more of that hot seed plastered the outside of her soaked vagina.

“Chinese is ordered!” Tobey called from the kitchen, clearly unaware of anything that was going on in Bobby's bedroom.

His voice, however, seemed to snap them both out of their trance. Jennifer didn't even bother looking back at Bobby as she quickly snatched up her clothes and fled from the room, embarrassed and ashamed of herself for the way she acted. She was going to have to set the record straight that something like that could never, repeat, never, happen again. Or did she want it to? She was so confused!

She had never been so sexually attracted to a man since she first met Tobey and she was lost and bewildered about her feelings. She couldn't believe that she had acted like such a total fucking slut, pulling her panties aside like that! He could have fucked her right then and there while her boyfriend was in the other room and she wouldn't have had a care in the world about it! In fact, the thought of it was enough to turn her on like no other. But she felt bad enough that she had let him cum all over her pussy and she could feel that her panties were soaked with their mixed juices right now.

She moved quickly into the bathroom and locked the door and stepped into the shower. As soon as the hot water hit her body she couldn't help but rub her clit to stroke that sperm all around her pussy, feeling some of that sticky cum coat her fingers. She brought it to her lips and groaned at the taste of their mingled extract. It tasted heavily.

As she thought of Tobey's brother's hung dick she couldn't help but also think of all the forbidden things he could do to her with it. The orgasm she had in the shower left her weak in the knees as she imagined what would have happened if Bobby had actually shoved that hard meat into her tight cunt instead of just rubbing the length against her outer pussy. Would it even fit? God, she wished she could find out! But she couldn't do that to Tobey! He would never forgive her if something happened between her and his brother.

+ + + + +

The next few days were pretty uneventful. Jennifer hadn't said a word to Tobey about what happened and Bobby wasn't in the apartment very much when she came home from work at night. Tobey told her that he was out at clubs.

After she had fucked herself in the shower thinking of Bobby, they had had a pleasant dinner and all three of them just talked and hung out and it surprisingly hadn't been that awkward. She had practically jumped on Tobey's dick that night, and after sucking his cock to a mind-blowing orgasm, she had donned a condom on his still-hard shaft and rode him until she exhausted herself from her release and she had felt him cum into the condom.

Tobey had asked her what had come over her but she had just told him it was all him. She feared they were too loud and Bobby had heard their excited moans and frantic rutting from a mile away, but she really didn't care. If he was going to be staying there in the room next to them, he was going to have to get used to her having sex with her boyfriend.

About a week later, Bobby came home late one night when Tobey and Jennifer were snuggled on the couch with a hot little number that looked like a model. She had light blue eyes and thick blonde hair and Jennifer was very jealous of the perfect curves she had on her.

Bobby introduced her as Kimberly and made some small talk before they disappeared into his room.

A half hour later, Jennifer could have sworn she heard moaning coming from Bobby's room. “I'm tired, Tobey, I think I am just going to crash.” She kissed him before he could protest and headed to their bedroom next to Bobby's.

She wasn't sure if it was intentional or not but the door to Bobby's room was cracked open and she could hear sounds of grunting and moaning coming from inside. She couldn't help but peek in the door and she placed her hand over her mouth to stifle a gasp at what she saw.

Bobby was standing naked and Kimberly was on her knees, her mouth wrapped around that large shaft as she gagged and choked struggling to take even half of it into her mouth. Jennifer went weak in the knees as she saw how massive that Bobby was fully erect. She had no idea how a woman could even begin to take it into her mouth, let alone her pussy! But Kimberly seemed to be doing an okay job and now had half of it in.

Bobby suddenly grabbed Kimberly by the back of her head and began thrusting his hips so that she would take more of him down her throat. Kimberly was gagging and choking but taking it like a pro as Bobby began to aggressively fuck her mouth.

Jennifer was growing wet between the legs and she knew that Tobey was likely asleep on the couch because she had heard him snoring before she nudged him awake and told him she was going to bed. Without a second thought, her hand was going into her shorts and she spread her legs as she began to rub her pussy.

Bobby fucked Kimberly's mouth for what seemed like hours but was probably around five minutes. He managed to get over half of his huge member into her mouth before he decided the time had come to fuck her. At that point, Jennifer had two fingers inside of her and was frigging herself at a slow pace as she watched in anticipation of what was to come next.

Bobby moved Kimberly onto the bed so she was on all fours and he got behind her. Jennifer stifled a gasp as she got a full view of that hung horse dick again. It looked like it was heavy in Bobby's hand as he unwrapped a condom and hurriedly wrapped it around that thick length.

He slowly worked it inside Kimberly and she was so tight that Jennifer could see her pussy lips gliding up and down the shaft every time Bobby thrust into her. Soon enough, Kimberly was moaning and shaking uncontrollably and Jennifer saw the signs of having an orgasm and couldn't believe that she was having one after just a few thrusts of that delicious cock in her pussy, and with a condom no less.

As Bobby began to fuck her harder and faster from behind, Kimberly seemed to be in a state of natural bliss. She was pushing back into those deep thrusts and shaking and moaning and shivering. She seemed to be having an orgasm every couple minutes, in a constant state of ecstasy.

Jennifer found her g-spot with her fingers and began to frantically fuck herself as the moans and groans from the bed became more excited and Bobby's thrusts more urgent. She had been standing in the doorway about twenty minutes now and she couldn't believe the stamina that Bobby had. He had been fucking Kimberly for over fifteen minutes without any signs of slowing down or blowing his load. He was like a machine!

It wasn't until a few minutes later that Jennifer could tell that Bobby was going to cum. He was thrusting harder and faster than ever and his ass suddenly flexed and Kimberly's eyes shot wide as that dick got impossibly huge inside of her and Bobby came into the condom. Just the feeling of that was enough to have her collapse on the bed in a heap and Jennifer could tell she was exhausted.

Jennifer came hard on her fingers and nearly fell to the floor the orgasm was so strong. She collapsed on their bed and thought of what she just witnessed, her pussy still tingling as she couldn't help but picture herself on the bed being pounded by that wonderful cock that belonged to Tobey's brother. She knew it was wrong but as time was going on, she was growing more and more curious about what would it would feel like to get drilled hard by that fantastic dick. She fell into a restless sleep and had dreams of Bobby ravishing her body that made her hunger for him even more.

+ + + + +

Tobey didn't seem to suspect at all what was going on. The weeks went by and once or twice a week Bobby would bring a random woman home at night and leave his door open as if beckoning Jennifer to be a voyeur. And every time she watched him fuck his date on his bed or against the desk or even on the floor or against a wall, all while masturbating herself to intense orgasms.

She still had sex with Tobey on a regular basis. Sometimes she would find him after watching his brother fucking and she would climb on Tobey's condom-covered cock and ride it like it was her last night on Earth, all the while thinking of Bobby. She couldn't get him and his magnificent cock out of her head.

The time came when they were alone in the apartment together and it almost scared Jennifer to be alone with Tobey's brother, because she didn't trust herself around him. But Tobey was going out with friends that he hadn't seen in a few weeks and she had to work early in the morning the next day so she knew he was going to be out late and had no intentions of holding him back from that.

She watched Tobey go and sat down on the couch to watch TV. Bobby was in his room doing God knows what and she hoped that he stayed there all night. After an hour she felt thirsty so she got up and walked to the fridge to get some water. She didn't think about her state of dress but since she was unwinding for the night she was just in a tank top and short shorts that barely covered her crotch. They were her favorite thing to wear around the house, mostly because she knew it drove both boys crazy.

Updated: December 17, 2016 — 12:36 pm
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