Jess had never allowed any guy near her asshole. It was strictly a no-fly zone. Anal sex was dirty and wrong, and that was the extent of it. A couple guys in college tried to press, and they were quickly shut down. Kyle joked about it when they were dating, and Jess told him to dream on. She still considered if off limits. There was no way Winston was sticking his cock back there, but she had to admit, the teasing felt really good. She even wiggled her butt for him.
~~~
Winston stared down at her perfectly straight blonde hair flowing over his hand and could not believe Jessica was down there licking and sucking around his balls and taint. Just as surprising was when she didn’t smack his hand away from her asshole. She was just full of surprises. Winston wondered just how dirty Jessica could get.
Jessica relaxed, and he took it as a sign to press further. He rubbed her puckered anus harder, enough to press the tip of his thumb into that tight ring. Jessica gasped and tensed up again, but he just left his thumb in place and gave her time to relax. She was squirming all over the place from his fingers in her cunt, so she naturally did the work of teasing her asshole with his thumb. Soon, Jessica was moaning and gasping more than she was licking and sucking. She kept a tight grasp on his prick, but she was having trouble keeping up with her mouth.
“Mmm…god…” she gasped.
“Don’t stop, baby, suck it,” he encouraged. Jessica had a nice, tight mouth, and he enjoyed it.
Jessica made strangled noises as she tried to take him deeper, moaning around her mouthful. Winston gently guided her head, using light pressure to keep her bobbing on him. It didn’t matter how much she took. It still felt great. She gagged, and he allowed her to back off, but only a little. He was going to train Jessica how to properly suck his dick.
“That’s it, Jessie. Relax and suck it. I know you can take it. It feels so fucking good, baby,” he encouraged.
Her eager moans were his reply.
Winston felt incredible power. His pretty blonde neighbor, the unattainable Jessica, was now in his bed, eagerly sucking his cock and fucking his hand. He held his hand completely still, and she did all the work, thrusting up and down on his fingers, working his thumb against her asshole. This was beyond his wildest dreams. He might even be able to fuck that tight little ass.
Winston knew this was the moment Kyle had pictured. He knew what guys like Kyle wanted. He let go of her head and stretched out his arm to reach his phone on the nightstand. He brought up the camera feature. The bedroom was well-lit—perfect for photos.
Jessica forced her head back, and he allowed it. She coughed and gasped for air. He had a perfect view, and it almost made him come too. But he held back, and snapped photos of his dick on Jessica’s face. Her eyes were shut tight. After a couple photos, he switched over to video. His boy Kyle was going to love this.
“Yes!” she shouted. “Mmm! Yes! Yesyesyesyes! Mmm…”
“That’s it, Jessie, come on my hand. Come for me, girl,” he growled.
“Oh god! Oh god!”
Jessica spasmed and her head hung forward, rubbing his wet cock all over her face. It was obvious she was coming, and coming hard. Her breath was ragged, and she gasped his name as she tried to regain control, but his fingers were still in her pussy, his thumb on her anus. She couldn’t control herself.
“Oh god! Ohh…”
“That’s it, Jessie, you’re coming again, aren’t you?” he taunted.
“Yes! Oh fuck yes!” she screamed.
Jessica was not a woman who just said fuck like that, which pleased Winston even more. He was so caught up watching her orgasms that he didn’t notice her eyes had opened.
“God! What are you doing?” she cried. “Stop that!”
“Chill out, Jessie. I’m doing it for Kyle.” Winston put the phone down. He didn’t want to ruin the mood.
“But…did he…did he ask you…”
“He didn’t need to. I know what guys like him like. He doesn’t want to see you fuck?”
“I…we…I don’t know…”
Winston chuckled. She was still riding his fingers, and could barely form words. Jessica was at his mercy. He slipped his fingers out of her. She looked disappointed. Jessica rested her head on his meaty thigh.
“Oh god,” she sighed.
“You might want some memories of this too, Jessie. Let’s just go with it, and worry about what to do with the pictures later.”
Jessica nodded.
Winston easily handled her lithe body, lifting her and sliding her on top. It was time to see her ride his cock. He wanted to see what she would do when she was on top of him. And it would make for some great pictures. Kyle may have been unsure of what he wanted, but Winston understood it better than he did. Winston knew the man would be kicking himself if he missed out on this.
“Come on and take that cock, baby,” he encouraged.
Jessica straddled him, sitting on top of his waist and rubbing his smooth, muscular chest. She looked down at him like she couldn’t really believe she was there. He could hardly believe it himself. She did as she was told and gripped his thick shaft. She had to raise her hips as she scooted backward, seeking him. His hands on her hips guided her back. Her slick, velvety lips engulfed him, and Jessica closed her eyes and bit her lip against the moan that slipped from her mouth. She paused, but he urged her on with gentle pressure on her hips. She put her hands on his chest as she bent forward and took him.
“Ohmygod,” she murmured.
“You like that, don’t you, Jessie?”
She nodded hard, her silky hair tossing.
“That’s it, baby. Ease on back.”
“Mmm…”
He was mostly inside her when Jessica stopped and began rocking back and forth on him. Winston moaned her name and gripped her hips tighter. He fought the urge to slam her up and down on him. She had to move at her own pace, but she felt so damned good he just wanted to go at her full bore. Winston was shocked she had not demanded a condom, but he wasn’t going to question his good fortune. He’d fill her pussy with his seed all night if that’s what she wanted. He just hoped she was on some kind of birth control. Jessica’s family was not ready for a half-black baby.
Her face was a mask of intense concentration. As she worked herself on his shaft, she took him deeper and moved faster, but she never let more than half of him out of her, like she couldn’t bear to part with his cock.
His hands slid to her ass, kneading her firm cheeks and helping her keep up her rhythm. He pulled her cheeks apart and his thumb touched her anus again. Her eyes popped open and her stare was a plea. The question was, what was Jessica pleading for? Winston did as before, just massaging her rosebud with the tip of his thumb. She didn’t miss a beat sliding back and forth on his cock. Jessica was more relaxed this time, and when she slid back his thumb pushed right into her anus.
“Winston…” she gasped.
“It’s okay, Jessie. Just go with it.”
Her butt flexed as he fucked her, working the tip of his thumb in and out of her anus. Jessica started fucking him harder. He was sure that the blonde beauty had never taken it in the ass before, but she obviously liked being played with back there. Winston didn’t know if he would have Jessica long enough to get his cock in her ass, but in the meantime he could have fun pushing her boundaries.
“Mmm…yesss…oh god…” she cried.
“Does that feel good, baby? You like that thumb in your ass?”
Jessica didn’t answer, but moaned his name, looking dazed.
“Yeah you do, I can see it in your eyes.”
“Oh god,” she groaned. It sounded like resignation.
The harder she pushed back onto his cock, the deeper it pushed his thumb into her ass, and now he was past the knuckle. Her rosebud tightly hugged his thick thumb, and when he flexed it inside her, Jessica wailed. Once she started wailing, she didn’t stop. She came hard, both her cunt and her anus locking down on him. It felt like she was trying to milk the cum righ
t out of him, and Winston had to fight to keep from coming with her. She hung her head, down, but he put a hand on her shoulder and pushed her back. He wanted to watch her as she climaxed. Her face was all twisted with passion, and then it looked like she couldn’t believe what she was feeling. Her eyes were a little bit unfocused. It seemed that Jessica was ready to collapse, but with Winston’s hands on her, she had no choice but to keep fucking him.
Jessica was like a rag doll when he pushed her upward. She sat up on his cock and her eyes flew open wide as she felt him push deeper than he had before. Winston knew she’d never felt anything that deep inside her. She stopped moving and just worked her hips, grinding onto his cock. Her pink lips looked obscene stretched around him.
“Oh god,” she groaned, staring into space. “It it’s so big.”
“Is it too big, baby?”
She shook her head quickly.
“You wanna ride that thing, don’t you Jessie?”
She nodded, biting her lips, her eyes burning into him. Winston loved it when women gave him that look.
“You wanna ride my big, black dick?”
Another nod. Her lips parted, but she didn’t speak.
Winston took her slender waist and lifted her a couple inches before dropping her back onto his shaft.
“Ohhh!”
He did it again, prompting another loud proclamation.
“Tell me, Jessie. Tell me what you want.”
“I…I…want it. I want your dick, baby,” she said, a tremble in her voice.
“My black cock,” he corrected. It was time to push her.
“Black cock,” she repeated, although it sounded more like a question.
“Right, Jessie. My big, fucking black cock.”
Jessica nodded, doing that sexy thing biting her lower lip, then gasped when he lifted her off his cock.
“Please. Please give me your cock,” she whimpered. “I want your black cock.”
“Yeah, Jessie. Now do it, fuck me, baby,” he grunted.
Watching Jessica lose control made him want to come. He wanted to come and then have her suck him until he was ready to fuck her again. That was how Winston would have treated most other women. But Jessica was not most women. He wanted to hear her beg, he wanted her to need him, but he couldn’t just use her. It was not love, but Winston had real feelings for her, and that made him want to protect Jessica, even as she fulfilled his fantasies. If it ever came to it, he would even protect her from herself.
His hands stayed on her hips to guide her, but Jessica had taken over, showing off her flexibility by working one foot underneath her. It allowed her to ride him up and down, sliding on the length of his cock. Winston reached for his phone once again.
“Let’s show Kyle what he wants, Jessie,” he urged.
“Yes! Ohh yes!” she vocalized, somewhere between a moan and a whimper.
Jessica stared right into the camera on his phone, transfixed. Winston knew she was only thinking of her husband now, and he fought down a spike of jealousy. Her moans grew louder and went up in pitch. She held onto her tits and teased her nipples. This was not the proper woman he knew. Jessica had transformed into a porn star for her husband. Only Winston knew it wasn’t all an act. Her ecstasy was real. He would prove it for Kyle.
“Come on, fuck me, Jessie!”
“Yes! Yes, baby! It’s so good.”
“What is? Tell me!”
“Fucking you…your dick…”
“Tell me what you want. Fucking say it,” he growled.
“Your cock! Your big dick!”
“Say it!”
“Oh god, please, don’t make me,” she begged.
“Say it! Tell me what you fucking want! Show Kyle!”
“Oh god…fuck…OH FUCK! I want it, baby. I want your big-fucking-black-cock. It’s so fucking big! Oh god, I fucking want it!” she cried.
Winston smiled. “That’s it, girl. Fuck that big black cock. Fuck me real good. Make me fucking come.”
“Yes, baby! I want you to come with me!”
It was the perfect moment, and when Kyle saw this video he was going to come in two seconds. Winston had no doubts. He snapped off stills while he recorded the video, but she felt so good riding him that he had trouble holding the phone steady. This wasn’t going to be a long video, because Winston was about to bust his nut.
“Yes! Yes! Fuck yes!” she cried.
Winston put his thumb on her clit and after just a few seconds of rubbing, she was coming again, bouncing vigorously on his shaft. He dropped the phone, but left the recording running. Kyle could hear the ending.
It was too easy to flip Jessica onto her back and keep his shaft buried in her. He lifted one of her legs and put it over his shoulder. Now he could keep stroking nice and deep into her. Winston took over, fucking her with powerful thrusts. It was like he poured all those months of frustration into her.
“Oh god! Oh fuck!” she cried. “Don’t stop! Don’t stop!” she begged. The camera was no longer on her. This was not a performance. This was all for him.
“Yeah…yeah…fuck, baby…fucking need you…gonna bust my fucking nut…”
“Mmm…yes…Winston…”
Jessica held onto his shoulders, she stroked his smooth head, she put her hand on his chest, the entire time keeping her eyes locked on his. The moment hung between them, pregnant with meaning and emotion. Just for that instant, they needed each other. It was only them. The rest of the world dropped away.
“Fuck, Jessie, I’m gonna do it…”
“Yes…yes…please, please come for me, Winston. Please come for me, my beautiful, beautiful man…”
Winston’s cock throbbed as deep as he could plant it inside her. He fell onto Jessica and crushed her to him. She trembled in his arms, and he had no idea if she was coming with him or not, but he planted his seed deep inside her cunt and clung to her like she was his anchor to the world.
twenty-three
Jess woke up beside Winston before the sun rose and tried to disentangle herself from his body without waking him. They were locked together so tightly. She didn’t want to leave his arms, but she couldn’t stay. He briefly stirred, but stayed in bed when she slipped away. Jess hugged herself, freezing. She looked around the dark bedroom for her clothes before she remembered they hadn’t made it upstairs with her.
The walk of shame was new to her. She had never had to scramble for her clothes in the dark so she could sneak out of someone’s place. It gave her an illicit thrill. Her dress was on the living room floor where she’d left it, and she stepped into it, only buttoning it far enough to keep it from falling off. Her keys were on the coffee table where she’d left them, but her phone was missing.
“It’s on the dining room table,” Winston said, his voice booming in the dark from the stairs.
Jess jumped and clutched her chest. “Jesus! You scared me.”
“Sorry. I came down and took your phone last night and put the pictures and videos on it.”
“Did you erase them from your phone?” she asked.
He paused, then smiled. “I will if I have to, but I’d like something to remember you by.”
Jess wondered when he did it. The last thing she remembered was a final slow, sensuous encounter, where they kissed and caressed each other until they both climaxed. She was asleep in his arms almost immediately afterward. She had been overwhelmed.
Winston came down from the steps, naked as the day he was born. That thick hose hung between his legs, and Jess couldn’t help staring at it. She only stopped herself by going to fetch her phone. Seeing his perfect, nude body stirred her lust all over again.
“I’ll never forget last night,” she said.
“Oh, I won’t either, but it’s nice to have the reminder.”
Jess turned to face him. She shivered, but it wasn’t the cold. It was the way he looked at her. She acted without thinking, pulling the straps of her dress from her shoulders and letting it drop to the floor. Her heart poun
ded.
“Is this a good reminder?”
“Damn, you’re fucking beautiful,” he murmured, coming to her.
They came together and kissed, but she did the impossible and pushed him away. It was nice to know she could still be rational when she had to.
“I really have to go,” she said.
“Tease.” He was smiling.
“You’re worried you won’t see me again—not like this.”
“Will I?”
“Kyle doesn’t come home until tomorrow.” She touched his chest, tracing his pecks with her fingers.
“Haven’t had enough?”
Jess pulled his lips down and kissed him. The kiss made her tingle all the way to her toes. She feared she might never get enough of him. Winston started touching her. She pushed him away as suddenly as she grabbed him.
“I really can’t stay.”
Winston visibly reined himself in and stepped away from her. “You’d better put that dress back on, then. If you don’t, I’m throwing you down on that couch.”
Oh god, she thought. Jess retrieved her dress from the floor—once again—and wiggled into it.
“Maybe I’ll see you tonight?” she asked.
“I hope so, if Kyle is coming home tomorrow—unless he does want to come over and watch.”
“I’ll see you later.”
Jess fled his house before her last ounce of willpower gave way and she begged Winston to throw her onto that couch. It was shockingly hot and humid when she stepped out into the predawn morning. It felt good after the icebox condition of Winston’s house, but she did not want to linger outside. Jess didn’t know any of the other neighbors well, but she still didn’t want them to see her skulking home in the early morning. Behaving like the walk-of-shame rookie she was, her eyes darted around as she crossed the street and scurried into her house.
Once safely inside, Jess immediately stripped and took a steaming shower. She felt that she must reek of sex after all of the fucking she did with Winston. Part of her wanted to leave his smell on her, but washing him away felt like an appropriate, important ritual. She was back in the home she shared with her husband. It wasn’t right that she brought Winston back with her.
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