Jess, Ch 2: The Surprise Next Door free porn video

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Jess waved goodbye to her parents as they drove off for traditional weekend dinner and movie date. They had almost skipped it to spend more time with her since she was only home for a few days, but she insisted on them having a good time. As they drove out of sight, Jess smiled; she was about to have a good time too.

Jess unbuttoned her jeans as she walked to her room. They slid off her gently curving hips as she shut the door. She was so horny, but it seemed the universe was conspiring against her having a good orgasm since her break from school had started. Her room was next to her parents, and she couldn't risk them hearing her, which limited her to rubbing her clit with her face pressed against the pillows to silence her moans. That usually left her more frustrated; she needed something inside her. She had planned on taking a toy in the shower, but her parents were remodeling, so the only available shower was in the master bathroom. But now her parents were gone, and Jess would have the house to herself.

She shuddered as she touched her pussy through her panties, which were already damp. They were plain, girly pink briefs. She couldn't risk her parents seeing her racier underwear, they might suspect her new college lifestyle and insist she switch to a local school. She pulled off her shirt to reveal a boring white bra that covered her full breasts well. She couldn't wait to get back to school and put on her lacy thongs and sheer demi bras that barely held her 34D's and their large pale nipples. Jess opened her suitcase and fished out her laptop and the small bag carefully hidden in the bottom. As she waited for the computer to start, she shut the blinds before she removed bra. After all, she couldn't have the neighbors see her.

She worked very hard to get her innocent angel reputation in her hometown. Years of being sweet, with her long wavy strawberry blond hair looking perfect, her naive-looking green eyes, and always wearing tops that hid her ample breasts and unflattering swimsuits had made it so that her parents trusted her at a party school across the country. Jess unlocked her computer and opened her folder of homemade movies. She knew which one she wanted to watch first.

It was a movie of the last time she had sex, the night before break started. She hit play and took off her panties as the video showed her tying her roommate Melanie spread eagled on the bed. Her hand moved down her thin patch of hair to touch her clit as she watched herself kissing her roommate and teasing her with a vibrator. In the video Jess slipped the vibrator into Melanie's pussy, and watching it slipped a finger in her own and moaned, happy there was no one to hear her. "Stop teasing me Jess, please," Melanie had pleaded. The vibrator was too low for her to cum

Watching the video, Jess pulled her finger out of her pussy and reached for the small bag. It was torture, what she did. Jess thought about that night, leaving Melanie tied up with the vibrator on low and bringing a fuck buddy to have sex on top of her while she was forced to watch.

Tom had pounded her doggy style with her tits bouncing in Melanie's face, just out of reach of her lips. Melanie whimpered with envy as Jess had three powerful orgasms and Tom sprayed his cum all over Melanie's tits before she was untied and had a massive orgasm of own. Melanie swore revenge, but for now Jess was going to enjoy the movie.

When Jess opened the bag however, her eyes widened. The bag was empty, her rabbit vibrator was gone! But the bag wasn't completely empty, Jess found a picture. It was her vibrator, pushed into Melanie's bald pussy! The message written on the picture was "Payback's a bitch!" Jess could have screamed. She needed her favorite toy in her, she needed a mind-blowing orgasm!

The sound of a car outside took her away from her misery. Jess peeked through the blinds to make sure her parents weren't back for something forgotten. It wasn't them, but her neighbors, heading out. She was about to leave the window when a dim light came on next door, in the neighbors' son Jim's room. Then Jim shut his blinds. Seemed like he wanted some privacy too.

She thought about Jim, he'd hit a growth spurt since she went to college, but he was still a few years younger than she. He was completely average physically, yet she knew that he was socially awkward and had no friends. A wicked smile appeared on Jess's lips. No friends, no one to believe him. Desperate times called for desperate measures, and she was beyond desperate!

Reaching into her suitcase Jess pulled out the only sexy underwear she had packed. The blue bra wasn't sheer, but it was lacy and cut low enough to expose the top of her areolas. And the matching panties let her ass cheeks hang out. She tossed her shirt and jeans back on and hurried over next door. Sneaking in through the back door Jess made her way to Jim's room. Her nipples grew hard as she heard moans from the room.

Jim's door was cracked open, and he was sitting at his desk with his back turned to her. He was naked, except for a towel on his lap. He was watching porn, and it looked like his hand was under the towel. Jess slipped into the room unnoticed. Jim was too busy watching a girl strip out of a cheap schoolgirl outfit. She looked to be almost 30, and way too old for school, but Jess massaged her breasts as she watched the girl suck a cock. Jess wanted a cock in her mouth too. As the girl started riding the cock, Jess made her move.

"That's terrible!" she cried out. Jim spun his chair around, pulling the towel around him to try to cover his body. He was a little more muscular than she expected, so that was good. Jim tried to speak, but Jess cut him off. "Those tits are just too fake! Just look at them flopping around! I think real tits are so much better. Don't you agree?" And with that she pulled off her shirt.

Jim just stared at her, slack-jawed. She knew he was trapped by the sight of her perfect breasts and her nipples pushing against the thin fabric. She unbuttoned her pants, showing off the front of her panties as she walked towards him.

"What do you think of them?" she asked. Jim was still speechless, but his grip on the towel had loosened. She brushed her hand on this towel, knocking it to the floor. Then it was her turn for her jaw to drop.

Jim's dick was a little longer than average, but Jess had fucked longer. What made her eyes bulge was its girth. It was the thickest cock she'd ever seen! It was almost as big around as a beer bottle! Jess had never put anything that big around inside her, but her pussy was practically dripping with the thought of it.

"Oh My God! Let's make a deal. You promise to keep your mouth shut, and I'll let you put that fat cock in me. This is a one time deal, and it's just sex! No strings attached. And if you tell anyone, I'll tell them that you're a liar and a pervert. Do you agree?" With that she let her pants fall to the floor and started running her fingertip around Jim's fat cock.

"Uh-huh," was all he could reply. He looked like he was going to cum at any moment, virgins always came quickly. She wanted to stuff her pussy, but she also wanted to see how much of him she could fit in her mouth. She knelt down and wrapped her lips around Jim's huge cock, but she could only get the head in comfortably. It seemed to be enough though, because as she ran her tongue under the base of his head, Jim started spasming, and fired a large stream of cum into the back of her throat.

Jess swallowed readily, but was caught off guard by the second stream, as big as the first. As the third stream hit her she gagged, and cum started pouring out of her mouth and onto her tits. But Jim wasn't done. Jess lost count of how many times his dick twitched and sent more thick hot cum falling out of her mouth.

When he was done, Jess swallowed what as left in her mouth, but from her neck to her panties she was covered in a porn star amount of thick jizz. Jim tried stammering an apology, but Jess smiled as she took off her soiled bra.

"That was amazing! And you're still rock hard, good." She pulled out her phone from her jeans and handed it to Jim as she wedged his cock between her large, messy breasts. "Take a picture, I want a souvenir."

He did as he was told, then asked quietly, "Do I get a souvenir too?"

Jess handed him her bra. "Of course! And if you fuck me like a good sex toy you'll get the matching panties too." And with that she pulled off her panties and wrapped them around his sticky cock. She pulled him up by his hard-on and moved him onto his bed. Climbing on top of him Jess took his hand and started rubbing it into her pussy. 

She moaned and said, "Feel how wet I am. God, you're so big, we'll have to take it slow." She rubbed her wet lips against Jim's dick, then slowly eased them around the fat head. She gasped loudly, her pussy was on fire! Jess rocked back and forth slowly, her moans becoming louder as she slowly slid down his shaft.

Jim looked like he was in heaven. "Can I touch your boobs?" he asked shyly.

"Uhh, yes," Jess managed to get out between moans. "What--ever...you...want--uuuhhhhh--just don't...leave any...marks..." So Jim reached up and started kneading her breasts. Jess was almost halfway down his thick pole when he started rubbing her hard nipples between his fingers. This pushed Jess over the edge, and she screamed out and convulsed with a violent orgasm that made her light headed.

When the stars in her vision cleared, she realized that she had slid the rest of the way down his cock. It felt amazing! Jess starting sliding up and down. Jim was so captivated by her bouncing breasts that he didn't seem to notice the drops of cum that fell off her and onto him. She leaned forward to put his face between his chest, and he greedily began licking and sucking on her nipples.

After only seconds of that Jim started bucking his hips against her, and she felt his cock twitching as he dumped loads of jizz inside her. She looked down and saw that it had been another huge load, with cum oozing out of her stuffed hole. And the boy was still hard as a rock!

"You think you can handle being on top, big boy?" He certainly could. He pounded her drenched pussy while she lay on her back. She moaned and wailed as he brought her to two small orgasms before pulling out and shooting a small load on her stomach. He seemed to be running out of seed. But his messy cock still looked ready to go. She started to lick her juices and his cum off his head, and she felt some of his jizz leaking from her pussy.

"Oh my God, are you ever limp?" Jim told her that he probably could only go one more time. "Well as your reward for that last orgasm, I'll let you pick the position."

That's how Jess ended up on her hands and knees, with Jim positioning himself behind her. Cum was still dripping out of her pussy onto the bed. Jim stopped it by easing his cock into her dripping snatch. Jess dug her nails into the pillow as Jim thrust the rest of the way in. Her whole body was rocking in rhythm with his pumping, cum dripping off her body.

Jim slowed down, and just as Jess was about to beg him to fuck her, she felt a finger circling her asshole. "Can I-" Jim started to ask, but Jess cut him off.

"Put your finger in there now, big boy." He did as he was told, and the sensation was amazing. Jess hugged the pillow to her chest, not caring that it was now covered in sticky semen. Jim kept pumping into her pussy, and with the finger in her ass it finally became too much. Jess started convulsing with her biggest orgasm yet. She screamed with the ecstasy of it all. She collapsed on the bed as Jim started cumming, and she could feel more of his hot seed on her back.

"No more," she gasped, "I can't take any more..." She looked over at Jim, and saw that his cock was finally starting to soften up. "That was amazing, big boy!" Jim started looking a little love-struck, and he asked if she could see him again before she left.

"No, this was only a one time thing, remember? Anyways, I'll need a day or two to recover from this. But since you were such a good boy, I'll give you one last reward. Get me the e-mails of the biggest slut, the biggest gossip, and the girl you want to fuck most at school, and they'll all receive an anonymous e-mail bragging about you. You'll never have to jerk off again." Jess put her shirt and jeans on top of her filthy body, then kissed Jim good night and went home to shower.

***

Melanie was in her dorm room, laying on Jess' bed. She had just used Jess' vibrator to bring herself to another orgasm, when her phone beeped. Picking it up, she saw it was a picture. Her eyes widened when she saw Jess' perfect breasts, covered in cum, with the fattest cock she had ever seen sandwiched between them. The message with it said, "I had to find another sex toy, this one definitely did the trick!"

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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...

3 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...

3 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,...

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...

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 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...

3 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...

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