Jess Part One: Our First Times free porn video

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My name is Will and I'm an average guy, not much to me. Slightly built at the age of 16 with black hair and a 7" dick. One day after returning from school with my sister Jess, we discovered a note saying that mom was staying with her sick sister to help out with her son and daughter. She'd left some money for pizza on the fridge in case we were hungry.

Now at this point I should probably tell you something about my sister. She's 16 like me with blonde hair and fairly muscled from her netball. She's has huge DD breasts and a killer ass. I'd first noticed Jess when we were both twelve. She'd been walking to her room wearing nothing but a towel, she tripped and fell giving me a perfect view of her pussy and when she stood the towel came away, presenting her B cup breasts as well. Ever since I'd wanted to fuck her.

"I'm off to take a shower" announced Jess. This was part of her after school routine. She'd shower then eat, and after that she'd do her homework. I decided to have a bite to eat and do some homework while she washed her gorgeous body.

As I walked down the hall way to my room I noticed a small crack in my sisters door at eye level. I closed the door and discovered that I could see nearly the whole room through it. The bed was in the center of the room, giving me a perfect view. We'd only just moved in a few weeks ago so I hadn't noticed it.

I moved off to my room and sat down to do a bit of english. After about twenty minutes I heard the bathroom door open and my sister walk to her room. I couldn't help myself and as soon as her door shut I snuck to the crack.

What I saw shocked me. Jess's towel was on the floor she was lying naked on her bed slipping the end of her hair brush between the glistening lips of her shaved pussy. I got an instant boner. She started moving it in and out with increasing speed, moaning softly as she sped up and her tits bouncing around. I watched through the door while she pounded her wonderful pussy continuously as she got close to orgasm and her moans became more intense. Her other hand was running over her breasts, massaging them and playing with her nipples. Then the door bell rang.

When I answered it I found Jess's friend Caitlyn standing there in a uniform. "Hey Caitlyn what's up?" I asked her. "Hey Will, I'm just here to drop off a package for Jess, I work with the post office now. Is she around?" she replied. "She's in the shower at the moment" I lied, "but I can sign for her if you want" I said. "That'd be great" she replied, handing me a clipboard and a pen. I signed the form and as I was handing it back, noticed her erect nipples sticking out from her D cup breasts. I glanced up and saw her looking a my crotch, noticing the erection I still sprouted. She took the clipboard, blushing furiously and handed me the package. She mumbled a thanks and practically ran back to her car. I looked at the package. It was about a foot long and three inches wide.

I put the box on the kitchen bench and snuck back along the hallway to my sisters door to peek through the hole. Sadly Jess had finished up and was getting dressed. She already had on her panties so I was deprived of the sight of her beautiful cunt. As she was putting on her bra she gave her pink nipples a tweak, moaning with pleasure. She lifted one of her nipples to her mouth and gave it a lick. I thought she'd go for round two but she stopped and put on her bra. Her underwear was jet black and impossibly made her look even more sexy.

I quietly snuck back to the kitchen as she finished putting the rest of her clothes on and picked up the package, acting as though I'd just gotten it from Caitlyn. I heard her door open and she came out wearing a tight black tank top and mini skirt. She doesn't normally wear clothes this skimpy and I couldn't help staring at her massive cleavage as she entered. "What you doing Will?" she asked me. "Nothing really this package just came for you" I replied. "Oh what is it?", I looked more carefully at the box but it had no label that I could see. " Not sure, doesn't say", I handed the package to her.

"You're acting a little strange, is something up?" she asked. At this point I couldn't look at her without thinking of her dripping pussy. "No nothing's wrong" I mumbled, still not looking at her directly. "You sure?, you look a little flushed." she said, sounding concerned. "Just feel a little ill is all, think I'll go lie down for a bit. "Ok then you probably should" she told me. I left the kitchen and lay down on my bed while Jess had something to eat.

I still had a hard on and it just wouldn't go away. It needed to be taken care of. I unzipped my pants and reached for my cock, lightly jacking it as I thought of what I'd seen. I knew I'd have a lot of fun times with the crack.

"Will, I think you should probably shut the door when your doing that", I looked up and saw Jess standing there leaning against the door frame. I'd forgotten to close the door. She padded over to me and sat on the edge of my bed. Staring at my dick she was mesmerized. I could see the lust and desire in her blue eyes. I tried to say something, anything, but nothing would come out. She was unsure of something for a moment but then seemed to come to a decision.

She reached down and lightly began to stroke my dick, making me shudder. I went along with it, not once thinking it was wrong to be doing this with my sister. My hands found their way under her shirt began to massage her breasts through her bra. She moaned with pleasure and took her hand away. She pulled off my pants and stripped to her underwear. "I'll give you the pleasure of taking off the rest" she murmured silkily as she reached for my shirt and took it off. She rolled onto me and straddled my crotch, rubbing her panty covered pussy against my cock, the feeling was amazing. I reached around her back and I unclasped her bra, letting her breasts fall into my arms. I threw the bra away and went to work on her tits, massaging them and tweaking her nipples while I sucked and licked them all over.

Her moans becoming louder as she moved faster, sending pleasure arcing through her luscious body. I ceased massaging her breasts and gently lifted her up. She moaned with disappointment as the stimulation stopped. I rolled over and rested on top of her, reaching to slip my hand down her panties and slip a finger into her sopping wet cunt. I slowly fingered her and rubbed her clit while working her panties down with my other hand. She lifted her ass to help me and grabbed my head, pulling me into an passionate kiss.

Finally her panties were off and I rolled us over again. Jess sat up and gently impaled herself on my rod. "I've wanted this for so long" she whispered as the pleasure washed over her. "So have I" I replied, and gently lifted her back up only to drop her down again. "Aaaahhhhh!" she cried as she dropped back onto my cock and I did it again, driving even deeper into her. I began to thrust upwards while she began to lift and drop herself in time, meeting my every thrust.

I groaned with pleasure and lust as we found a rhythm and built each other to orgasm. We moved in unison, fucking each other like there was no tomorrow, not knowing when we'd have another chance. "Aaahhhhhhhhhhh!" she moaned as her pussy was impaled over and over again. "This is so awesome, I've wanted to fuck you for ages" I gasped out as the pleasure rose within me, almost tipping me over the edge. "Fuck me Will, faster" she moaned out in response, lost in the sensations of our coupling. I complied and sped up, hammering into her soaked cunt.

"I'M CUMMING!" she screamed as she came hard around my dick, her pussy muscles contracting around my cock as I came as well, grunting and emptying my cum into her tight pussy. Stream after stream I pumped into her until it seeped out of her pussy around my cock.

We lay there in the aftermath of our fucking with Jess on top and both of us panting like dogs. "That was amazing" gasped Jess, "Yeah it was, but I hope your on the pill" I gasped back. "Don't worry, I am" she murmured. "Your an amazing fucker Will." "Thanks, I've fantasized about banging you ever since that time I saw your pussy when we were twelve." I murmured, beginning to get my breath back. " Really? That was the first time I saw you get a boner. You ran off to your room after having yourself a good stare at my pussy". "Yeah I went and jacked off straight away" I replied. "And I went and and fingered myself like hell" she told me.

By now both of us had our breath back, sticky from sweat and our mixed juices. I led Jess to the shower and turned on the water. We stepped in and I grabbed the body wash from the rack. I got a nice sized dollop and made a lather with my hands. I started out massaging her neck from behind, enticing moans from her as her muscles relaxed. I slowly work my way lower and moved onto her enormous breasts. I kneaded in the soap starting at the top and working my way over her tits, circling her nipples and catching them between my fingers. I gave them a pull causing Jess to cry out in pleasure and continued down underneath them. I lifted them, letting them fall so they would bounce while pulling on her nipples, causing My sister to moan louder.

Moving on from her beautiful globes I traveled down her stomach to her navel running my soaped up hands over her stomach, making her sigh with pleasure. I moved down even further to he engorged pussy, running my fingers along her slit and flicking her clit, making her almost collapse. I worked her cunt with my hands, slipping my fingers inside her and massaging around her lips. In no time at all my hands were covered in more of her juices then they were in soap, her moaning the entire time I washed her body.

I turned her and knelt down so her shinning honeypot was at eye level. I snaked out my tongue to taste the wonders of her glistening pussy. Her hips bucked as I made contact and licked along her slit, up to her clit. My tongue moved down once again and licked along the length of her sweet smelling pussy. I repeated the action a few more times before finally penetrating her with my tongue, pushing as far in as I can, my nose against here clit and my mouth pressed to her slit. I licked her inside and out, clearing her pussy of her juices. I savored the delicious flavor of the nectar coming from her crevice. My tongue plunged in and out, flicking her clit on each exit, causing my sister to go frantic with lust. Her pussy exploded and her juices covered my face as she rode through orgasm after orgasm, pleasure lancing through her and her hips bucking into my face as I continued to eat he out.

When she came down for her high I stood up and kissed her deeply, letting her taste herself as our tongues danced together in our mouths. We broke the kiss and just stood underneath the jets of water.

"That was amazing Will" Jess whispered in my ear, nibbling at my earlobe and lightly grasping my cock. She knelt down to my cock and took the head in her mouth. The feeling was exquisite as she took more of my dick in, sucking all the while. She bobbed her head backwards and forwards, going deeper still until the head touched the back off her throat and she gagged on the flesh. Her fingers fondled my balls as she sucked my dick, bringing me closer to cumming. My rod was covered in her saliva as I cam inside her mouth, spewing it down her throat. She tried to swallow all my cum but couldn't keep up and it overflowed.

My dick popped from her mouth as she finished licking the last of my cum from her lips and then cleaning me off as well. She stood up and kissed me deeply, a light salty flavor on her lips and tongue. "How was that bro?" she murmured as we stopped kissing. "It was awesome sis" I murmured back.

And I slammed my still hard cock deep into my sister.

End of part one

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Jess and Aarons New Neighbor OWWH 4Chapter 59

The next night, Emma and Brent knocked on our door at 6 pm. Bruiser stayed next door at Emma’s, sleeping on her couch. Jess had decided that we pull no punches. We were both completely naked as we answered the door. Jess was wearing the nipples clamps (that she had originally bought for me.) They dangled from the erect nubs sticking out from her chest; I had played with her tits for several minutes before installing the clamps to ensure that they were rock hard. I, myself, wore nothing...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 76

“Whatever you like, Mistress,” Jess said obediently. Emma pushed herself up to a sitting position; she then twisted her body to dig back in the pile of toys. Retrieving one, she turned back to Jess. “I want to fuck you,” Emma said simply, holding up a strap-on dildo which dangled in front of Jess’ face. “As you wish, Mistress. I’ll need a bit of help getting back up, though,” she said. She floundered a bit on the floor to show her lack of mobility. Emma leaned over and helped pull Jess back...

4 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 33

Once outside, she realized that he had driven and she had no way home. She took her phone back out of the clutch purse she had brought and discovered that her hands were still shaking in anger. Emma closed her eyes and counted backward from ten to calm herself. Reaching zero, she reopened her eyes and dialed Jess on her phone. “Hello?” Jess said on the other end of the receiver. “H-Hi, Jess. It’s Emma.” Emma’s voice was quivering while she hovered on the line in between ‘blind fury’ and...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 75

Jess was still in a haze from the orgasm so Emma’s “No” didn’t really register for a moment or two. But then, her eyes widened in horror as Emma pushed the bullet harder against her clit rather than removing it. “Em, you, you have to, take it off,” Jess stammered. “If you want me to take it off, just use your safeword, princess,” Emma said cheerily. ‘Shit no’ automatically ran through Jess’ mind, but she said nothing. She just took a deep breath to prepare herself for what was to...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 57

Once she was alone, Emma headed over to our apartment. Jess opened the door and before Emma could greet her, Jess grabbed Emma’s arm and pulled her into the apartment. “Tell me EVERYTHING!” Jess said excitedly. She led Emma over to the couch where they both sat down. Emma was about to speak when she caught the sight of me on the floor. She blinked and was silent for a moment as she took in the scene. I was on the floor on the other side of the room. I was nude. That wasn’t the surprising...

4 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 16

The rest of the shift seemed to drag by. She was both elated that she had gotten Mike to ask her out and simultaneously pissed that he only wanted to fuck her. She told herself that he was a guy and she shouldn’t have expected any different. Jess clearly hadn’t. And she didn’t WANT to be mad at him. He really was a decent person; well, at least before today she had thought so. So, she made a tremendous effort to be civil and friendly the rest of the shift. She would get over it, she...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 41

After dinner, Jess suggested we watch a movie. I don’t know what it was. The Notebook maybe, or some other chick flick. I didn’t really care; chick flicks are much better for getting the girls’ juices flowing than, say, Die Hard 2. Young guys, who may be reading this, take note. ‘Priorities’ and ‘Pussy’ both start with a ‘P’. Coincidence? I think not. We were all sitting on the couch with me in the middle. Both girls had hands on my thighs as they watched the movie, engrossed by whatever was...

1 year ago
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Jess and Aarons New Neighbor OWWH 4Chapter 114

Back on dry land, the group found that I had laid out four towels on the sand over near the fire pit. I was aware of the schedule of events and was doing my assigned tasks. Jess and Amelia both dropped down onto towels. Andre and Paul sat down on either side of Amelia; Jess had to pull the other two boys down next to her by their hands. All of the guys had shrunken as a result of the cold water (no sympathy here), so Amelia wrapped her hands around the guys’ cocks and started pumping. Andre...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 8

Emma knocked on our door that night at around 9 pm. She had just gotten out of work. She was smiling, but Jess could tell something was off as soon as she opened the door. “Hi, what’s up, Em?” she asked. I was sitting on the couch reading a magazine. Fully clothed for a change. I know that doesn’t happen much in these stories, but I actually do wear clothes every once in a while in real life. “Hey guys, it’s not too late to stop by, is it?” she asked. I could see her eyes looked a bit...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 9

I am not used to getting tears, either sad or happy, after pleasing women and I was a bit flummoxed as for what to do; I decided to sit there on my heels looking stupidly at her nude body. Jess handled it much better by pulling Emma tightly against her chest. Jess coddled her head and shushed her softly as Emma cried hard against her. The tears made huge dark spots on Jess’ red blouse. “It’s ok, it’s ok...” Jess repeated in whispers. I gave Jess a questioning look and she waved at me to be...

3 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 29

I had to waddle my way back to the car through the mall thanks to the toy wedged in my bottom. As is typical for mall shoppers though, no one even gave me a second glance. I’m not sure they would have had I been naked from the waist down with the toy sticking out from me. “How much do I owe you for everything, Jess?” Emma asked. “Nothing, it’s our treat,” Jess said. “Really, I want to pa-” Emma started to say but Jess cut her off. “It’s not up for discussion. They are all gifts. I know...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 48

Emma saw my erection hanging below me and noticed it was leaking pre-cum. “Jess, he hasn’t orgasmed yet...” It sounded more like a question than a statement. “No, he usually won’t from just anal. Even though he enjoys it, he still needs stimulation down there to push him over the edge,” Jess commented. “Should I stroke him or something?” Emma asked. “Yes, please!” I said eagerly before realizing my mistake. “No.” Jess said it very firmly. “For speaking without permission, he can stay...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 52

A few minutes later, Jess returned to her own apartment. Emma was still seated on the couch, but she was clearly much calmer. “How you doing in here, kiddo?” Jess asked. Emma sniffled and nodded. “Better, I think, thank you. Was he...” “He’s still there,” Jess reassured her. “And I explained a little of what happened; I didn’t give him specifics. You can do that later if you choose. But he is very understanding. And very HOT by the way, good job!” Emma forced a giggle. “Thanks.” “Anyway,...

3 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 69

Before Emma could ask what she meant, Jess’ hands moved down to Emma’s crotch. Emma shivered at Jess’ touch as her fingertips tickled her sides on the way. Jess’ experienced digits had no trouble finding Emma’s clit, swollen from the excitement of screwing me. Emma settled back down onto me as Jess worked her magic. Emma’s eyes closed and she rested her head against the crook of my neck. I could feel her breath there as she sighed heavily. Emma rocked her hips back and forth against my lap...

1 year ago
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Jess and Aarons New Neighbor OWWH 4Chapter 116

The girls returned and stood above me as I moaned, eyes closed, lying on the ground beneath them... “Guess he liked it,” Jess commented, looking down on me with her hands on her hips. “Seems so,” Amelia agreed. She bent over and helped me up off the sand. She brushed off my back and I returned the favor for her. “K, children,” Jess said. “I think it’s time to call it a night.” The guys all helped carry the cooler and other gear back to the limo. Phil saw the mostly naked and covered in...

2 years ago
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Jess is a girl

Jess is a girl Jess is my name They try to tell me I'm a boy all the time But today something changed it aint hard to define Now they know Jess is a girl, and was all the time I was watching girls with my eyes I was envying their bodies, couldn't hold it I was praying to God every single night But now they know Jess is a girl they know Jess is a girl finally came out as a woman - like that Got tired of the charade finally knew it was time to change used to...

3 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 117

Emma’s bachelorette party followed a few weeks later. Jess and Emma had planned it together the day after the bachelor party. Jess had hoped to arrange it sooner but she wanted it to be after Emma’s twenty-first birthday. “K, so we need to put together a guest list,” Jess said, notepad and pen resting on her leg. Emma shrugged. “Um, you? And I guess Liz?” It was more of a question than a statement. Jess scribbled on the pad. “Sure. Anyone else?” Jess asked. Emma was quiet for a moment...

3 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 11

Jess took me by the hand and turned to Emma. She crooked her finger at her in a “Come here” gesture and led us both back to the living room. Without saying anything, Jess began unbuttoning my pants. Emma’s eyes went wide. “I, I ... don’t think I am ready for-” Jess interrupted her. “Calm down. You’re not doing anything. You are just going to watch. Have a seat,” she said, pointing to the floor. My pants were down on the floor and my underwear stuck out in front of me. Emma had already...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 26

Back out on the floor of the store, Jess headed over to the ‘intimate apparel’ section. ‘Intimate’ in this case basically just meant bras and panties. I felt uncomfortable hanging around the area, like people would think that I was some sort of pervert (which I was. Am. Nevermind.) Jess picked up a few pairs of panties. The first was pure white and very lacy, completely unlike the boy-shorts that Emma was currently wearing. The second pair was a thong. “Jess!” Emma hissed. “I can’t wear...

3 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 40

Emma made it to PetHub with only seconds to spare; she had to hurry to make it to the time clock on time. Not that her boss was a bastard about that sort of thing; she simply took great pride in her work ethic and tried very hard to be punctual. Nothing exciting happened until she checked her phone while on break. “Holy fuck,” she said aloud in the empty break-room. Jess had forwarded a link to Todd’s page. Jess had added a note: “Hmm, guess he pissed SOMEONE off.” When she followed the...

2 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 65

“Ok, Slave Jess, Slave Aaron,” Emma said, saving Brent from having to respond, “I think this has been enough fun for one night. Brent and I should probably leave you two alone.” “As you wish, Mistress,” Jess said. I repeated the phrase a beat later. Jess knelt down in front of Brent. “Thank you, Master Brent, for playing with this slave’s ass, mouth, and pussy tonight. I hope you will do so again in the future,” she said to him. She wasn’t going to let him off the hook and she got Brent to...

3 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 64

I breathed a massive sigh of relief that I wasn’t to be the center of attention. “Yes, Mistress! Right away!” I said, running straight to the bathroom to get our gear. It took me a few minutes to fill the enema bag with the necessary warm water and gather up everything that would be needed. When I returned, I saw that Jess was kneeling on the towel, her face to the floor. I pulled a rubber glove onto my hand. I squirted some lube onto the enema nozzle and worked my gloved hand over...

2 years ago
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Jess Ch 2b Melanies Break

Melanie woke in Jess' bed, as she had every day of fall break. She was naked, of course, and hugging Jess' pillow. Stretching her arms out, she bumped into a toy. It was her roommate's, a nice rabbit vibrator. She smelled her pussy juices on it, dried since last night. It reminded her of Jess, which made her nipples hard.Mel put the toy in her already wet cunt and turned it on. The vibrations took her thoughts back to the last time she and Jess had played with toys together. Well, Melanie...

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