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Jill Kassidy

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Like 425
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Videos with Jill Kassidy

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Car Wash Special
Date added: 2019-05-05 Rating:
Like 138
Dislike 6
Comments: 20
Description : Chloe Cherry and Jill Kassidy, two friends that work together at a local car wash, are devastated to learn that the company has closed down. Now they're both without jobs! They have a senior trip coming up soon and won't have the money to go! Fortunately, it doesn't take them long to realize that they're old enough to start their OWN car wash business.

The girls excitedly start their business by going door-to-door, giving out flyers and offering to clean cars for 50% off their regular asking price. Things don't go quite as smoothly as they expected, though, as they get turned down by one car owner after the next, leaving them feeling discouraged.

Finally, they find a car owner that allows them to wash his fancy red car. They do so with glee, basking in the sunshine as they rub the car all over, every movement sensual. Each time they lean over the car or stoop down to get more water, their sexy forms are shown off. There are many classic 'wet t-shirt' moments as the girls soak each other with the hose, enjoying every moment of their new job. When they're done, they're rewarded with enough funds to go on their senior trip!

Exhilarated from their success, they return to one of their homes to get dried off. They're so giddy and filled with such energy that they hardly know what to do with themselves, congratulating each other on a job well done. Of course, the tension and excitement leads to an enthusiastic kiss between the friends, which then leads to even more fun. They eagerly play with each other's perky breasts, eat out each other's sweet pussies, and trib to their heart's content. Maybe they'll just have to stay in business with each other if this is one of the perks!

Story inspired by an original submission by Girlsway member, BlackDow!
Maid For Each Other: My M.A.I.D.D.
Date added: 2019-04-25 Rating:
Like 203
Dislike 9
Comments: 27
Description : When Angela White meets her new robot maid, Jill Kassidy, for the first time, she's unsettled. Jill's so human-like and it gives Angela the creeps. Yet, she has a busy life and everyone keeps saying how great these M.A.I.D.D.s are, so she figured she'd finally give it a chance.

Although things are initially awkward between them, Jill's constant presence and innocence endears her to Angela. It's been so long since Angela let anyone close, having been burned in the past when wearing her heart on her sleeve. Yet, her wall slowly comes down and she finds herself looking forward to seeing Jill every day after work -- she's more to Angela than just the housemaid. Yet, she's afraid of confronting what she really feels for the droid... until Jill one day asks her about love.

As Jill curiously listens, Angela stumbles, trying to explain what love is the best she can, even if she doesn't really feel she's the best person for the job. Even if she WERE able to adequately explain it, would a robot be capable of truly understanding it? So instead of explaining what love is, Angela shows Jill instead.

Angela leads the way, giving Jill her first sexual experience while exploring her own complicated feelings. They're slow and sensual as they kiss and touch each other, learning how to show their affection. Jill relishes the new sensations as Angela sucks on her breasts and eats out her pussy. As Jill eagerly returns the favor, giving it her all to show her love, Angela finally embraces what they've had all along.
Nerds Rule!: Fansexual
Date added: 2019-02-18 Rating:
Like 208
Dislike 14
Comments: 27
Description : Two girls, Lilly Ford and Jill Kassidy, who have been friends for a long time, are each a huge fan of comics and sci-fi, and especially each a die-hard fan for rivalling series - Fantasy Factory: Wastelands and Future Darkly.

They're about to sit down and watch an episode of Wastelands, which has Lilly more than excited, though Jill looks almost bored. If Lilly likes sci-fi so much, they should watch Future Darkly, Jill drawls. Lilly is insulted as Jill switches to Future Darkly with a grin, saying she wants to watch Michael Vegas. 'You just want to watch him for his sexy body and sexy hair... Meanwhile, there's Kenna, April, and Abigail with THEIR sexy bodies...' Lilly dreamily retorts.

Lilly gushes over the stunning women, not only about how sexy they are but how empowered they are, too, which makes Jill roll her eyes. Jill doesn't care so much about the empowerment -- she just wants to watch Michael sexily control girls. Lilly is exasperated, saying that's all they see these days, which is why Wastelands is SO GOOD. She continues to gush about how strong Kenna's character was in that series -- strong enough to punch a robot through a wall! -- and then Jill slowly grins. 'Are you a lesbian?' she suddenly asks.

Lilly is flustered, insisting that she just REALLY likes Wastelands... 'Come on, you have to admit that Abigail being controlling is hot as hell!' Lilly remarks in defense. After a moment's contemplation, Jill agrees, even if she still thinks Michael is hotter.

Jill continues on to say that she really liked that tight black outfit Abigail wore, though... As she says this, she slowly touches along her body. Lilly eyes widen and she excitedly calls her friend out on it, pressing her for more intimate details. Jill admits that MAYBE she thought about Abigail while touching herself once... This confession sends Lilly over the moon, since now she knows she's not the only one who did the same! Jill playfully says that they're 18, so they can do stuff like that now. Lilly teases Jill further, slyly saying that she obviously put a lot of thought into this... Was Jill thinking about stuff THEY could do together, too? Jill locks eyes with her friend -- sure, there are things they can do together.

Jill finally confesses that she's always wanted to kiss a girl. Lilly is endlessly amused, playfully stating that Jill might be a lesbian herself, but just doesn't know it yet. Jill shrugs -- she's down to experiment...

This sparks something new between the two friends. As they draw closer together, the heat between them building, they exchange nerdy references to help break the tension. The passion between them intensifies as they sensually make out, then undress each other, eager to explore further. They're excited as they suck breasts, lick pussies, and trib each other to pure orgasmic bliss. Maybe they can't agree on which show is best, but they CAN agree that they'll have hot lesbian sex again!

Story inspired by an original submission by Girlsway member, Sam27!
Bad Behavior
Date added: 2018-12-28 Rating:
Like 185
Dislike 8
Comments: 17
Description : Paige Owens stands at the door of her bedroom, knocking on it and trying to get her mother to let them out. They're hungry! Also, they need to go to the bathroom! The mother points out that Paige has her OWN bathroom, and refuses to let them out since she and her friends are grounded.

Frustrated, Paige returns to her bedroom, where her two friends, Adria Rae and Jill Kassidy are waiting. They're not pleased that Paige's mother has grounded them ALL -- can she even do that? Although Adria and Jill continue to complain, Paige tries to save face and appease her friends. They can watch movies or do makeovers...

Adria and Jill don't care for the options given to them. They both continue to complain about missing time with their boyfriends. Paige says that they JUST saw their boyfriends -- are they really THAT horny? Adria and Jill teases her, feeling each other up in a playful way. Does their insatiable hunger for sex make Paige uncomfortable? Paige admits that, yeah, it does a bit, actually. Adria insists that she and Jill can at least have fun together... They don't hesitate to kiss each other, starting to makeout on the bed while Paige averts her eyes and exclaims that SHE's not having fun.

Paige makes a run for it, slipping away into the bathroom and closing the door behind her. She's completely grossed out by her friends making out in HER bed! Maybe it's not so much that she's actually grossed out by them, though -- maybe seeing them making out is making HER horny as well!

While Paige is gone, Adria and Jill stop making out. They look towards the closed bathroom door and wonders aloud if they're actually making Paige mad? It's all fun and games, but they don't want to push their friend TOO far. However, as soon as Paige cracks open the bathroom door, they launch back into the makeout session, all tongue and teeth as they embrace.

Despite her initial reaction, now Paige seems intrigued by what her friends are doing. She slowly joins, saying that she's still weirded out by what they're doing on her bed. Yet, as soon as Adria and Jill crawl towards her, running their hands over her body and cooing into her ear, she's putty.

Adria and Jill make their reluctant friend melt beneath their sensual touches. Paige is blissed out as they fondle her perky breasts and lick her sweet pussy. While she's happy to let them have their way with her, she's soon bold enough to make her friends writhe in pleasure as well. She'll never think that getting it on with another girl is gross again!
Can I Kiss You?
Date added: 2018-11-24 Rating:
Like 189
Dislike 19
Comments: 23
Description : London River is resting on her bed, lost in a book, when her step-daughter, Jill Kassidy, shyly lets herself into the room. She joins her step-mother on the bed and asks if London remembers that she said Jill could talk to her about anything? This gets London's full attention as she sits close to Jill, concern on her face. Of course she remembers! What's bothering her?

London's not prepared when Jill starts off by saying she had a first date with a girl. However, she recovers quickly as Jill admits that she pushed her date away when it came time for a goodnight kiss. She's never kissed anyone before, so she got scared. In fact, that's why she's there talking with London -- she needs help learning how to kiss!

At first, London is weirded out, but she can't resist Jill's puppy dog eyes. Although she's never thought about kissing her daughter before, who better to teach her the way of the world than her own mother? She'd hate to see Jill get her heart broken again.

London steels her nerves and lightly kisses Jill while giving her instructions on what she should do in turn. The first kiss is soft and exploratory, with London demonstrating how girls like soft touches to the face and neck. Despite trying to keep things simple, it doesn't take long for the lesson to get hot and heavy as primal urges take over. Their hands start to wander and even London can't help but to grip Jill's hips and pull her close.

After an intense kissing session, with lots of tongue, Jill seems satisfied with the lesson. As she gets up to leave, London's not ready to see her go since she was really getting into the lesson! She insists that there's more she can teach Jill...

London continues to teach Jill how to please a woman by showing her how to fondle and suck on breasts. This leads to learning about eating pussy next, and Jill is a quick learner. London is prepared to go above and beyond now to help Jill master the goodnight kiss and more!
Closer to Home
Date added: 2018-11-13 Rating:
Like 171
Dislike 12
Comments: 19
Description : Jill Kassidy comes bouncing down her driveway. Opening her mailbox, she's delighted to see that she's finally received a piece of mail she's been waiting for. She goes back inside and sits on her couch, but she's too nervous to open the letter. Taking a deep breath, she gathers her courage and tears open the envelope. Just then, her stepmom, Kendra James walks in and sits down beside on the couch as Jill reads the letter. Looking up at her mom with a massive grin, Jill excitedly tells her that she's been accepted to Alaskan University! But Kendra doesn't share Jill's excitement. She tells Jill that Alaska is too far. Didn't they talk about Jill staying closer to home? If she goes to a community college in the area instead, she can ease her way into the college experience by still not being too far away from her stepmom, Kendra adds. Jill doesn't agree, saying that she wants to get a good job, and Alaskan University has a really good program for the kind of field she wants to go into. Kendra keeps trying to convince her, even sweetening the deal by offering to buy her a new car, but Jill is insistent.

'But wouldn't you miss...us?' Kendra asks with a sultry bat of her beautiful eyelashes, caressing Jill's arm softly. 'Wouldn't you miss our time together?' Kendra asks as she hikes up her skirt, pulling aside her panties to enticingly reveal her shaved pussy. Jill gasps at the sight of it, biting her lip. 'Wouldn't you miss your stepmother's love?' Kendra asks. Of course Jill would, and she immediately shows Kendra how much she would miss it, bending down and tonguing her stepmother's clit eagerly. Kendra moans, her pussy already dripping. Jill slides two fingers inside Kendra's tight box, finger-fucking her until Kendra squeals in ecstasy. Pretty soon it's Jill's turn to be taken care of, and Kendra slips off her daughter's clothes, lowering her face to Jill's juicy little slit. Kendra knows just what her daughter likes, and she'll do ANYTHING to make sure that Jill stays closer to home.
Too Hot for Teacher: Birthday Surprise
Date added: 2018-10-14 Rating:
Like 204
Dislike 8
Comments: 16
Description : Aidra Fox, a sexy teacher, is busy grading papers at home when there's a knock on the door. Happy for the interruption, she answers the door with a smile. Jill Kassidy, wearing a big bow in her hair and holding a cupcake, greets Aidra with a big smile of her own. Aidra is pleased but curious what Jill is doing on her doorstep. Jill presents her with the cupcake, announcing that she just wanted to bring a birthday cupcake to her favorite teacher!

Aidra is touched that a student remembered her birthday... although she doesn't remember ever telling her students when her birthday is! Jill admits that she MAY HAVE checked out Aidra's social media sites and found out her birthday that way... Aidra's face drops a little. Sure, some of her social media posts are pretty innocent and boring, but others... Jill grins at Aidra's expression, admitting that, yes, she knows about THOSE posts, too!

Aidra doesn't get a chance to respond, interrupted by a phone call. She's thankful as she hurries back to her desk and answers the phone, taking the call from her boss. He's just calling to check in about the curriculum she has outlined for the next semester. Aidra sits down and goes over it with him, although Jill takes this opportunity to dive between her teacher's legs and tease her pussy.

Aidra is surprised but doesn't resist too much when Jill massages her pussy before enthusiastically eating her out. This has never happened before but Aidra wants more! As Jill works her tight pussy with her tongue and fingers, Aidra tries her best to have a normal phone conversation with her boss, but is unable to bite back her moans and whimpers of pleasure. Afraid of getting caught, she tells the principal she has to go, but Jill's not done with giving her her birthday gift yet!
Babysitting Lesbians: Caught on the Couch
Date added: 2018-06-14 Rating:
Like 168
Dislike 9
Comments: 26
Description : Abigail Mac and Whitney Wright have hired Jill Kassidy to babysit but for some reason, Whitney doesn't fully trust her. When she starts grilling her with questions, Abigail tries to smooth things over asking Whitney to play nice. Abigail tells her that they planned this outing for quite some time and that she's clearly overreacting. Abigail convinces Whitney to let this go so they can have a good time together and leave the house. Jill now has the house all to herself and is going to take full advantage. She pulls out the computer and puts on some porn and starts playing with herself. As she loses track of time, Abigail and Whitney get home a little sooner than expected. When Whitney is about to walk into the house, she sees Jill playing with her pussy through the window, she tells Abigail to look but Abigail tells her she's probably just watching a movie. They enter the house to find Jill on the living room couch masturbating and watching porn. Whitney can't believe she would be doing this in their home, but Abigail tries to smooth things over saying that all teenagers act like that. Jill apologizes saying that she's really sorry and would like to make it up to them. When Whitney asks her how she could possibly make it up to them, Jill proposes they have a threesome! Whitney can't believe she would have the nerve to suggest that after being caught red handed but Abigail thinks it's a great idea. Once Jill and Abigail decide to seduce Whitney, her horniness gets the best of her and the three girls end up having the time of their life!
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Pictures with Jill Kassidy

Show details
Hide details
Car Wash Special
Date added: 2019-05-05 Rating:
Like 20
Dislike 0
Comments: 0
Maid For Each Other: My M.A.I.D.D.
Date added: 2019-04-25 Rating:
Like 20
Dislike 0
Comments: 0
Fansexual
Date added: 2019-02-18 Rating:
Like 26
Dislike 0
Comments: 0
Bad Behavior
Date added: 2018-12-28 Rating:
Like 19
Dislike 0
Comments: 0
Can I Kiss You?
Date added: 2018-11-24 Rating:
Like 17
Dislike 0
Comments: 0
Closer to Home
Date added: 2018-11-13 Rating:
Like 21
Dislike 0
Comments: 0
Too Hot for Teacher: Birthday Surprise
Date added: 2018-10-14 Rating:
Like 26
Dislike 0
Comments: 1
Babysitting Lesbians: Caught on the Couch
Date added: 2018-06-14 Rating:
Like 24
Dislike 0
Comments: 0
The Lost Phone
Date added: 2018-02-02 Rating:
Like 19
Dislike 0
Comments: 1
Teach Me To Be A Lesbian
Date added: 2017-11-11 Rating:
Like 19
Dislike 0
Comments: 1
Call Me My Sister's Name
Date added: 2017-07-23 Rating:
Like 23
Dislike 0
Comments: 1
Glamour - Jill Kassidy
Date added: 2017-07-23 Rating:
Like 13
Dislike 0
Comments: 0
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Comments
7 comments

Undo
BenLewisAus
Jill is just amazing keep her updates coming :>
2019-02-22 09:13
Like 0
Dislike 0
Ken Sky W
Yeah Ben Gotta keep Jill updates going strong
2019-05-19 15:19
Like 0
Dislike 0
XERACX_Girls
I Love The Sweet & Sexy Jill Kassidy Please More Thanks
2018-10-13 22:35
Like 0
Dislike 0
user_23231475
Could I request a scene with girls in Cecilia de Rafael or Wolford seamless pantyhose? A true pantyhose foot fetish movie where girls worship each other’s pantyhose feet and keep pantyhose on the entire movie? A seduction of one girl by an aggressive other in pantyhose from Girlsway would be a dream cum true! :-)
2018-02-03 21:15
Like 1
Dislike 0
the nightmare of freddy krueger 83
i love you sweet jill
2017-10-28 07:49
Like 2
Dislike 0
user_23540413
I love you!!
2019-02-17 12:51
Like 0
Dislike 0
Uncle Teddy
Great first GW scene from Jill. Very sexy, cute girl. More Jill Kassidy please.
2017-07-30 09:40
Like 3
Dislike 0
YulkaFan
Fingers crossed for beautiful Jill to become a Girlsway regular after her fantastic debut with Elsa.
2017-07-23 20:55
Like 4
Dislike 0
user_21871155
I hope we will see more movies + pics from this attractiv girl!
2017-02-17 14:02
Like 4
Dislike 0
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