Dave , Jennifer, New Roommates Ch. 01

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This is my first story submission. I’ve been a long time reader and have always had ideas to write my own stories. This story is inspired by a certain person that I hold dear and enjoy every moment we get together. It’s a long drawn out story so if you need a quick patch to the sex, this story is not one you’ll like. I encourage & welcome your constructive feedback and comments. Please enjoy.


The night had become late. Jessica and her husband had just returned from the local bar and inquired of the babysitter about the behaviour of the kids that evening.

“The kids were good, overall” said the Jennifer. “There were a couple of moments where tantrums occurred but in general they were very well behaved.” added Jennifer.

Jessica smiled and said “that’s good. I know they enjoy you as their babysitter.” All the while Jessica was speaking, she noticed her husband seemed to be staring a little too intently at the babysitter and had that expressionless smile plastered on his face. Jessica took mental note, for the time being, of the extended stare that her husband offered towards the younger girl. Jessica was a girl that they had grown to trust and appreciate as a caring and reliable sitter for their kids so she thought the better of making a scene right then. It was such a long search to find someone that they trusted enough to leave their kids with so that they could enjoy nights out together.

Nights out were something that just didn’t happen that much after the kids were born. Even more scarce were the nights of passion filled sex together, nights when they could escape the cares of the world and just give themselves completely to the other. This recognition that her husband was ogling the babysitter in his mind didn’t necessarily surprise Jessica since she knew that he had a definite attraction to brown haired thin girls (especially those with big tits). Jennifer was definetly an attractive girl with larger D-Cup breasts with cleavage that seemed to always be on display, and her charisma just made it easy to be drawn to her.

After about 30 really long seconds of Jessica’s husband simply staring at Jennifer in a dream like state, he snapped out of his trance realizing that he might have been staring a little bit too long. He looked at Jessica and then back to Jennifer and then said, “Let’s get you back home, shall we?”. “That would be great. I have to get up early tomorrow morning.” replied Jennifer.

Jessica thanked Jennifer for being so great with the kids and went to her purse to give her the money for watching the kids. After accepting the money from Jessica, Jennifer and Jessica’s husband got into the vehicle and started off down the road. Jessica was only slightly concerned about Jennifer and her husband being alone in the vehicle after she noticed his obvious lust for the young woman. She trusted her husband not to act on his desires. He had the same trust of her.

Tim and Jennifer were quietly riding together in the vehicle.

Tim broke the silence by asking Jennifer, “So. What do you have to get up early for tomorrow?”.

Jennifer answered, “I have a appointment with an apartment complex tomorrow morning. I need to get a new place since my current roommate is not happy with my boyfriend staying over from time to time.”

“I didn’t know you had a boyfriend” Tim blurted out. “How long have you two been going out?”

About 2 months now” said Jennifer. “He lives in California and is trying to find work here in Arizona so he comes and stays with me from time to time.”

“That’s nice. I’m glad to hear that someone as attractive as you has someone” Tim said.

“Well, Thank you Tim. It’s nice to hear someone say they think I’m attractive.” as she blushed and formed a slight smile on her face hearing his remarks.

“Seriously? Your boyfriend doesn’t tell you that you’re attractive?” Tim asked, surprised that she was exhibiting such low self esteem for such a gorgeous girl (with such nice tits).

“Yeah, he does sometimes, but I always notice him looking at other women that aren’t…um…shall we say…as “blessed” as I am. I think maybe he has a thing for women with smaller breasts or something. I don’t know.”

Immediately after saying that, she regretted it thinking that she was divulging too much information to a man that she admired and respected.

Her inner thoughts, lately, had become very sexual towards Tim. However, due to her relationship with him and his family as a babysitter whom they trusted, she was afraid that her admission of such facts may have been a bit Freudian. Was it a sub-conscience effort maybe to bring up the topic of her body to see what Tim might say?

Tim was definitely surprised by her admitting such personal information. At first, he thought that maybe he should just let the conversation die there, but felt obligated to fill the awkward silence.

Tim then added, “Every man has a unique thing that they really enjoy and fantasize about, but that beylikdüzü ucuz escort doesn’t necessarily mean that they will ever act on them. I, myself, have a bit of thing for big boobs and even though I have that infatuation, I don’t ever do more than just look.” As he was saying that he wondered in his mind what her tits would like like naked. He also had a bit of a foot fetish as well but kept that secret.

“I’m sure you’re right.” Jennifer replied as she stared out the side window pondering his words. She realized at that moment that Tim must have loved having her as their babysitter and wondered how often he looked at her big boobs.

A few minutes later they arrived at Jennifer’s Apartment and Tim pulled next to the curb in front of her apartment to let her out.

“Thank you again for giving me a ride home Tim.” Jennifer said as she opened the door and turned to step out of the vehicle.

This always gave Tim a opportunity to admire Jennifer’s curvy and tight butt that she seemed to always tease him with each time he dropped her off at her home. As she was exiting she turned to close the door and as always leaned down and looked into the vehicle at Tim to say Goodbye.

“Goodbye Mr. Smith”.

“Goodbye Jennifer” Tim answered, as he tried his hardest not to stare into the extreme cleavage that Jennifer presented him each time before closing the car door.


A few months passed and Jessica and Tim had called on Jennifer’s services now and then. The last time Jennifer babysat for them, she indicated to Tim on the way home that her boyfriend had found employment here and was moving out here to be with her the upcoming weekend.

Tim offered to help them move into the new apartment that they had found but since her boyfriend didn’t have much that he was bringing, she politely declined and thank’d him for the offer. She said something that Tim found strange. He picked up on the fact that She said the place they were getting was only temporary until they found a more permanent home. One they could afford. This caused Tim to wonder, What was the job was that her boyfriend got that meant they had to live so close to broke? He decided not to pry and just let the information stew in his head for a while. After dropping her off and admiring her assets again as she walked away, he returned back to his home and got into bed for the evening.

“I think Jennifer and her boyfriend might be having some financial difficulty.” Tim said to Jessica.

“What gives you that impression?” asked Jessica.

“She divulged to me on the way home tonight that the place they are moving into is only temporary and that they would need to find another place sometime soon. One that they can afford. My guess is that what they can afford, is not very much.”

“That doesn’t necessarily mean that that they are having financial difficulty.”

Jessica commented. “I’ve seen many couples do a temporary thing prior to settling into a place they can call home. Maybe they are waiting for the income from her boyfriends job to roll in before they settle down somewhere?”

“I guess.” Tim said, not sure why he was feeling afraid for Jennifer being left homeless at some point in the near future. Maybe it was the comment that she made about her boyfriend scoping other girls. Maybe it was just something that she said that suggested they were unsure of their future together. Tim let it go and went to sleep.


A week had passed and Jessica & Tim planned another night on the town. Tim went and picked Jennifer up at her new apartment and after giving her the usual information: Where they would be, how late she should expect them to be, emergency numbers, etc… They eventually left her and the kids to enjoy their evening out.

Despite the extra time they had been spending out together, Jessica and Tim had not had sex with each other for quite some time. Tim knew that Jessica was feeling the frustration of that fact and even noticed a certain website that she often visited. It implied that she might be seeking some “outside-the-marriage” activity. Jessica was always a very sexual person that didn’t have much reservation about her sexuality and was always a very willing and giving partner. Tim just seemed distracted lately. He thought it was because he was not as attracted to her as much as he had in the past but dismissed that idea. He eventually reasoned that with 2 kids taking up all your time, it left very little energy and time for playful fun with her.

As they drove, Jessica moved her left hand onto Tim’s right leg and lightly carressed it. He looked over at her and smiled with an appreciation for her sentiment, all the while noticing that his cock was responding to her touch.

They arrived at the restaurant and sat down, ordering their meals and drinks and talked casually during the dinner. Afterwards, they both went to the movie theater to watch a new movie that had some really beylikdüzü üniversiteli escort strong sexual undertones. In the movie, a man and woman discovers that bringing in a third person into their bedroom rejuvinates their sex life and allows them to explore their individual fantasies with the new partners. But of course, in the end it just made a bigger mess of their situation. It didn’t stop Tim from trying to take advantage of the situation in the theater. He had strategically moved his arm around the back of her neck and allowed his fingers to rest on her right tit. Jessica didn’t resist so he used the erotic moments of the movie to facilitate his groping her tit and nipple. Jessica loved to have her nipples played with and the more he manipulated them, the more aroused she became. She allowed herself to get into the playing around as well by tracing her fingers over his stiff cock that was snaking it’s way down his right leg. They didn’t do much more than just fondle each other and before they knew it, the movie was over. They waited through the credits and went back to the vehicle.

The movie acted as a catalyst for a conversation by both Tim and Jessica. On the ride home, they discussed the movie and it’s plot.

Jessica curiously asked Tim “Would you ever be able to do what they did in that movie?”.

“I’m not sure.” Tim replied. “I haven’t really given it much thought. Have you?”.

“No, not much. I sometimes hear about people that have done that and wonder how they handle it without getting jealous and hurt.” Unbeknownst to Tim, her question was her way of finding out if Tim would ever consider doing such an erotic thing. She always knew him to be a bit conservative and careful and not an adventure seeker. She was excited by the concept and wondered if she could convince Tim to participate in such a risque thing.

Tim said, “I think you would have to “completely” trust your partner. I think it’s something that is just meant to break up the pattern of ordinary sexual behavior. Why do you ask? Do you see that as something we could handle in our marriage?”. He of course immediately had Jennifer in mind as someone that he would love to have participate in such a experience with and was afraid that his asking the question might expose his thoughts to Jessica.

“Are you actually suggesting that we need to consider such things??” snapped Jessica in an attempt to disguise her desire. “Is our marriage so bad that you want to bring in other people?”

“No No. I’m not suggesting it. I only asked out of curiosity. Relax!” Tim said defensively.

“Ok, Well, since you are just curious, allow me to satisfy your curiosity. I think the situation and the people would have to be special in order for us to ever consider such a thing. I can’t see us becoming swingers or anything like that, but I think if we had a trusted couple of friends that we knew, and would respect our marriage and our limitations, I think it would possible.”

Tim was completely shocked by Jessica’s answer! He totally expected her to take the road of resentment, anger, disgust, and simply shoot him down further for even bringing it up. Despite her sexual appetite, he never thought she would be interested in participating in extracurricular activities such as swinging or swapping.

“I don’t know anyone that we know that would even remotely be a consideration for such a thing, so I guess it’s not something that we’ll be exploring anyways.” Tim added.

Tim took that opportunity to change the subject and they completed their ride back home.

As usual, Jessica paid Jennifer for watching the kids and Tim and her got into the car so he could bring her back home. As they were driving, Tim noticed that Jennifer seemed distant and distracted.

“Is everything ok Jennifer?” he asked.

“Oh, yeah. Sorry, I was just daydreaming” Jennifer said.

“About What?”

“Oh, it’s nothing.”

“Are you sure? You know you can talk to me Jennifer” Tim assured her.

“Well…it’s just…never mind. It’s a private thing.” Jennifer wanted to talk to Tim about her thoughts but was afraid to since she felt that she would be putting him in an usual position.

“Well, just so you know, you can trust me to keep any conversation we have completely private. I would gladly be a listening ear if you needed one.”

“Thank you Mr. Smith. I appreciate the offer.”

Tim noticed that a while back, she had called him by his first name but ever since that time she always referred to him as Mr. Smith. He felt uneasy being referred to as “Mr. Smith” by someone that he deemed a close and trusted part of his family circle.

“You can call me Tim if you want Jennifer. No need to be so formal :)” he offered.

She smiled at him and said “Ok, Tim”.

“How are you and your boyfriend?” Tim asked wondering if he was prying to close to her personal life.

“We’re good.” she answered. “We are getting beyoğlu escort along and still looking for a place where we can stay that we can afford yet.”

“If you don’t mind me asking, what price range do you need to stay in?” Tim was a financial advisor and thought that perhaps he may be able to offer some expertise in this area for Jennifer and her boyfriend.

“Lower than almost every apartment complex wants around here.” she said with a resolute sadness.

Tim was not able to get any figures from Jennifer but feeling guilty and concerned for her he blurted out “You know? You could always stay with Jessica and I if you absolutely needed to.”

He instantly regretted saying that, knowing that Jessica would likely be upset with him for making such an offer without first discussing it with her. It’s not that she wouldn’t want to help out, but rather that he had made the offer without consorting with her.

“Thank you Mr. Sm.., errr… I mean, Tim” she corrected as she giggled. “I appreciate that offer. I’ll be sure to keep that in mind.”

Her giggle was intoxicating to Tim’s ears and instantly he was reminded of her youthfulness and his desire for her. They arrived at her apartment, and once again she exited the vehicle as she always would. He admired her ass once again and anticipated the great view of her cleavage as she turned and leaned inward to say goodbye.

Tonight was especially exciting since she had decided to wear a very loose fitting crop neck shirt. Her shirt completely sagged away from her body and exposed her very large breasts to his gaze. Her bra was a demi-style and exposed a lot of the tops of her breasts to Tim’s lusting eyes. Tim was unable to divert his eyes from her tits. He was locked into a solid stare at the massive jugs. Jennifer noticed his gaze as she was shutting the door and smiled a bit inside knowing that he was admiring her tits.

Her boyfriend was not as fond as them as she would like him to be. He often commented on how much smaller boobs looked nice to him. Having Tim stare at her tits, in the way he did, gave her the satisfaction that her tits were indeed attractive to men. She shut the door and put a little more wiggle into her walk as she walked toward the apartment. She was certain that Tim was watching her since he hadn’t pulled away yet like he usually did after she shut the car door.

Once she turned the corner to her apartment, Tim pulled away.

Jennifer walked up the stairs to her apartment and locked the door behind her. Her boyfriend was not in the lit up living room, as he usually was, so she put her stuff down on the Coffee table and walked into the bedroom to see if he was there instead. As she walked into the doorway, she noticed him sitting in front of the computer with just the light from the screen illuminating the room. She didn’t say anything or make any noise.

It was then that she noticed that on the screen was a video playing of a petite woman with tiny tits and pencil eraser-like nipples giving head to a guy. She then noticed that her boyfriend didn’t have any pants on and that his hand was slowly working itself up and down on his cock as he intently stared at the screen. She wanted to blurt out “WFT!!??” but instead found herself just standing there watching her boyfriend pleasure himself to porn. She didn’t know what to say and didn’t know if it would be worth making a big scene over since she herself had just intentionally flirted with Tim as she left his vehicle.

She suddenly realized that he was not yet aware that she had arrived back home, so she slowly backed out of the doorway and went back to the living room. She thought it would be best to not let him know that she’d caught him. She unlocked the apartment door, opened it back up carefully, and then shut the door loudly to indicate that she had just entered the apartment. After shutting the door and locking it again, she called out “I’m HOME!” to warn him of her presence. She could her her boyfriend suddenlty rustling in the bedroom and then after a few minutes she heard him reply, “just a minute!”. ‘As if THAT wasn’t suspicious’, she thought to herself.

Jennifer loved her boyfriend and knew that he was a good person inside and was always willing to do whatever she asked of him. This fact prevented her from using the scene she had just witnessed against him and decided to just file it away as ‘good information’ in case she needed it some day.

The time for them to move out of their 3 month lease came very quickly. Jennifer’s boyfriend Dave had his job, but it was the only real source of income other than the small amount of money Jennifer got from babysitting Tim and Jessica’s kids. Jennifer didn’t want to ask for more work since it seemed a bit unprofessional to do so as a babysitter. All she could do was remind them that she was always available if they ever needed her.

One day, she received a call from Jessica asking if she was available during the entire day tomorrow to help her with the kids. Jessica had a new job that she could do from home and it was pulling her attention away from the kids so she really needed the help watching the kids while she worked. Jennifer gladly accepted and said that she would be there as soon as the bus could get her there. Jessica thanked her and offered a increase in the usual pay for her troubles.

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