Jess And I free porn video

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Jess and I By Sarah M. I can't believe we lost again! A 2-7 team just pasted us, 45-0. Our school is officially the worst school for sports in history. None of our teams ever win anything. It's pretty sad when the only trophies in the case are for cheerleading. The cheerleaders are always good in competition, usually ending up in the top 5 in state. At least they are predicted to be the best squad in state. I am a trainer for the football and basketball teams, being too small to actually play. I had hoped that getting a jersey of my own would help me get chicks, what a laugh. No girl would actually go out with me. I'm a runt. I also thought that my twin sister being popular would help me get women too; again no luck. I'm just a loser at love. Anyway, just wanted to fill you in on my life up to this point. Three days after the last game, I was just cleaning up the locker room after practice when the head trainer for the team came in and told me to get to the med office. When I got there, I saw my sister, a cheerleader, being helped up on to the table. "What's going on Jess!" I yelled. "Jess has a broken leg, we think. We've called for an ambulance," the head trainer told me. "We were up in a pyramid and Jess tried to back summersault off, and Trish and Jen were to catch her. Their grip slipped and Jess landed hard on the ground," Denise, the head cheerleader, told me. "Tell them it was an accident! It's not their fault!" Jess said through tears of pain. Just then the ambulance pulled up and took Jess to the hospital, as I followed them there after I called our parents. About a week later, I walked into Jess' room to see if she needed anything. She was laying on her bed with her leg in a cast. Trish and Denise were over to visit her. Everyone was depressed. "Can I get you anything, Jess?" "Another leg?" Jess answered in a sarcastic voice. "OK, I'm outta here." "Wait Sam, I'm sorry. I didn't mean to bite your head off." "That's alright. I know you didn't mean anything by it." "Well, I wish I had a healthy leg. We are going to have to withdraw from state now." "Why?" I asked. "Don't you have a replacement? I know it sucks for you Jen, but the squad can still get by can't it?" "Well, we don't have a replacement," Denise said. "Janet would have been ours but she moved 2 months ago. According to the rules, it has to be an officially registered person to be a replacement, or a school could bring in a ringer. We're stuck." "I'm sorry to hear that. You girls are the only thing this school has going for it. Wow, this sucks. If there is anything I can do..." I just let that trail off. It was on Saturday after another loss that my life changed. I was in my room when I got a knock on the door. The door opened and my Mom, Jess (on crutches), and Denise walked in. "Yeah" I said, thinking it strange that these three would be in my room. "We need to talk," Jess said. "OK." "We think we may have come up with a plan to stay in the competition." Denise said. "That's great," I said. "What's this got to do with me? You wouldn't be in here telling me this unless I had to be involved." They all three looked at each other nervously, no one saying anything. After a couple of seconds, my Mom spoke. "We will just come right out and ask. If you don't want to do it, we will understand." "Understand what?" "We need you to take Jess' place on the squad." I started laughing. When no one else laughed, I realized that they were serious. "NO!" I said, hoping that would put an end to that. "Just hear us out," Jess said. "Nothing to hear," I answered. "Do you even know what you're asking? You want me to take my sister's place! Hello, I'm a guy! I thought you couldn't have alternates anyhow?" "Sam, you wouldn't be an alternate. You would be ME!" Jess answered. That statement took me aback, unable to say anything when my mother joined in. "Sam, sweetie, you have to admit, you look just like your sister." I was floored. I don't look like her, I think? "Sam," Denise said, "you really do look like her. If you just had your hair done up and some makeup, you would really be identical twins." "Wait just a minute," I said. "Just for the sake of argument I do look like Jess. I'm not her! I don't know the cheers; I wouldn't know how to be Jess. This is ridiculous that we are even having this conversation. The answer is no." "Sam," my mother said, "you haven't heard what I have to offer. You do this and I will buy you a car." "What?" "I'll buy you a car. I have money in savings and I will buy you a used car; only if you do this for your sister and the squad." "Sam," Jess said, "I don't like the idea of you pretending to be me anymore than you do, but I might lose out on a cheerleading scholarship I need for school. I'm begging you to do this." "I can't believe you are all serious about this," I said. "How can I pull this off?" "We'll all be here to help," Denise said. "We'll get you trained on the routines. We'll work around the clock if we have too." "We?" I asked. "All the cheerleaders have agreed on the plan." "What?!?" I screamed. "Everyone's going to know?" "Of course, Sam," Jess said. "What did you think?" "I don't know. This is all so f-ing crazy. I'm going to be the laughing stock of the whole school. I'll probably get beat up by the bigger guys and everyone will think I'm gay! I can't do this." "No one is going to lay a hand on you," Denise said. "Not if any guy wants to be with any of the girls. You will not be treated badly by anyone. I guarantee it." My mind was going crazy thinking about all of this. I needed to think. I told them I would think about it to get them out of my room. After they left, I got myself a glass of whiskey from my stash and tried to put that whole thing out of my mind. Like I would do that! A car would be nice, but not at that price. What were they thinking? Like I could even learn the routines in time anyhow. I was still trying to reason things out when I got a knock on the door. I didn't even realize that two hours has passed since that meeting. It was Jess by herself. "Sam, before you say no, hear me out. I really need that scholarship. I want to go to Albect University and the only way I can afford to go is with the scholarship. I really need you to do this." "Jess, how do you expect me to pull it off?" "I think you can do it. We have 3 months until State and all the girls are more than willing to help you learn everything." "It's not just the routines, Jess. I don't care what everyone says. Throwing some makeup on me and putting me in a uniform won't make me look like you. And that's not the end of it. Girls walk and talk differently than guys. I don't know how to act like you. I don't know how to be a girl. I don't think 3 months of training will get me there." "I'll train you on how to act like me! By the end of three months, no one will be able to tell the difference. I promise. By the way, I hate to do this to you, but I'm willing to go so far as blackmail you into this." "What are you talking about?" "Lets just say that I know a certain cheerleader that likes you." "Who?" I said excitedly. "Trish." Wow, I thought. I've had a serious crush on Trish forever. She is the most beautiful girl in the school, at least in my eyes. This must be some kind of joke or something. "What do you mean blackmail me? I'll just ask her out." "If you don't do this, Trish will never forgive you and certainly will not ever go out with you. Bank on that. She wouldn't do anything to hurt me or any of the other girls. Just you remember that. So come on, at least give it a try. If it doesn't work out, I won't stand in your way with Trish; and mom will still buy you that car." All I could think about was Trish. She really likes me? Jesus, Jess really does have me in a pickle. I guess I could act like I'm trying; fail and no one will be the wiser. Then I'll have Trish and a car. "All right, Jess. You win. I'll try." Jess started crying and gave me a hug. "Thank you so much, Sam. I'll never forget this." Jess then called for mom to come in and told her the news. "Sam, thank you. Don't worry about a thing. We'll all have you ready by the time of the competition. Well, Jess, we better get started. I'll run to the stores to get a few things." After my mom left the room, I asked Jess, "What's she talking about getting started." "Well, everyone decided that if you said yes, we would start on making you into me right away. Mom went to get you a few things to help with the transformation." "Why the hurry? State isn't for a while." "We all decided that you are going to be me starting right now. We feel that the best way for you to learn is to live it. Now, I'm going to start a bath for you. I'll call you when it's ready." What the heck did I get myself into? To be continued.

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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,...

4 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...

2 years 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...

4 years ago
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Jess and I Part 2

Jess and I (Pt. 2) By Sarah M. I followed Jess into the bathroom. "What the hell do you mean I have to start right now? I have my own life to live, remember? How can I just disappear?" "Sam, everything has been arranged. The principal has agreed to let you go to school as a girl, and as far as being a trainer for the football team; they already said they could get along fine without you. Don't worry about people making fun of you. Denise has already let the word out that...

3 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...

3 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...

4 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...

3 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 Part One Our First Times

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...

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...

BDSM
4 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 109

Kenny grabbed his crotch to shift the uncomfortable bulge that had formed there. All of the guys were in a similar predicament and it did not escape Amelia’s notice. “Don’t worry, boys, we will address your situation in a moment,” she said. Then she turned to me. “Aaron, go clean yourself up, then get your cleaning supplies ready.” I departed to wash the hand that had been in my wife’s ass a few minutes before. Amelia walked over to Andre and Jess over to Paul. Both girls knelt down on the...

4 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 110

Clean again (relatively speaking), Jess turned toward Phil. Phil looked panic stricken as Jess gazed down at him; “Deer in the headlights” was the phrase that ran through my mind. Jess sat down, cross legged, on the side of him, her back to the wall just as he was. Gently took his plate from his lap, she set it off to the side. She went to unbutton his pants but he put his hands on hers to stop her. “Jess-Ma’am, I don’t think it would be right,” he said. His tone was not upset, but...

3 years ago
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Jess and Aarons New Neighbor OWWH 4Chapter 6

Jess made a comically loud “Hurmph!” followed by “What a fucking jerk!” “I know, right? That was the last time we went out. Actually, that was the last time we even talked. He didn’t call me after that and I made no effort to talk to him at school,” she said sadly. “That’s a pretty depressing sexual history,” I said. In my defense, I did regret saying it immediately, pretty much at the exact moment that Jess shot me her look of death. I’m pretty sure the words she mouthed were “Fucking...

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