Jolene’s Triumph

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Please note: this happened to Jolene back nine years before the present, back in 2011.

Jolene got the final box out of her tiny Kia, then walked it up to the front door. The new house still looked empty and lonely from where she was standing. The cool night air was keeping her from getting too sweaty.

She pushed her way into the front door, then left the box in the hallway. She hoped that Phoenix was going to be different. She would be far enough away from Brent Mossing for now to allow herself to focus on her new goals. Her divorce from her husband was finalized, and she was relieved that he would be rotting in jail for now.

Jolene stepped up into the kitchen area. She hoped that she could get her hands on some decent furniture soon. At least the house came with appliances. She gave a small kick at one of the other cardboard boxes, trying to push it along the floor. She sat down and rested her head on the box.

Jolene had a lot to think about. Her new job started in two days, and she was nervous about doing commercial sales. The residential market seemed easier to her. Austin was a challenging market as it was.

She let her hand run down her leg. She felt so strange now, slimming down and tightening up. It felt good to have a goal to achieve for once. She got up, then tried to haul the cardboard box to the bedroom. She grunted and strained as she lifted the box. “Ugh! I need to get some muscle.”

She decided to push it along to get it into the bedroom. Sweaty from the moving, she pulled off her shirt and pants. She looked down and sighed. “Someday,” she muttered. She was still pleased with the weight loss.

Jolene got the sleeping back out of its satchel and unrolled it. She climbed in and propped her head up with her hands. She was feeling overwhelmed with the abrupt change in her life, and started to cry helplessly. “Brent,” she whined. “I will always love you, sweetie.” Jolene sniffed and whimpered for another fifteen minutes, then drifted off.

The next day, Jolene went exploring her community. She had only been to Phoenix twice just to close on the duplex. Given her financial troubles, she was glad she got such a great deal on the place. She got on her cutoff jean shorts and a pink t-shirt with her sneakers.

As she went out to her car, she noticed the neighbour next door coming out. It was a young blonde lady, holding a toddler on her hip. The woman looked as if she was struggling. Jolene dashed over and stood on the stoop.

The woman looked shocked, but Jolene smiled and did a cute little curtsy. “I’m so sorry!” She offered her hand but took it away quickly. “I’m Jolene Wyman. I just moved in next door.”

The young woman got a look of comprehension and nodded. “Yeah, I though I heard someone moving around last night. I’m Twyla.” She gave her toddler a hike up. “This here’s Brylee.”

Jolene squatted down and held her hands on her knees. “Hi, Brylee!” Brylee hid her face. “Let me take your bags, at least.” Jolene took the bags and helped Twyla out to her car. Jolene was surprised at the size of her SUV, although it did look like an older model.

As Twyla helped Brylee into her car seat, Jolene could not help but notice how busty Twyla was. She had a unpleasantly coloured tattoo right down along her right boob, which Jolene found to be a turn-off. She clearly had surgery, and her breasts looked tight and probably uncomfortable.

Twyla took the bags and threw them next to her daughter. “Thanks…uh, Jolene, right?”

“That’s right!” Jolene stepped away from the curb as Twyla got into her car. “Have a pleasant day!”

“Oh, Jo!” Twyla lowered the power window. “Come by sometime. You a drinker?”

“I can manage,” Jolene giggled. She waved as they pulled away. Jolene went to her own car and headed out.

She came across a gym not too far away from her house. She ventured in and bought a day pass, then went to have a look around. She walked into the main room and checked out some of the more advanced equipment.

Jolene fixated on a large, muscular blonde woman with a deep tan. She looked ridiculously ripped, almost looking like a man in her face. She tried to focus on something else as she stood there.

“Hey!” barked the muscular woman. “You, in the pink.”

Jolene froze and looked away. The muscly woman made her way over and stood within inches of Jolene.

“Hey,” the woman said. Her long blonde hair was tied up in a ponytail, and seemed to flip back and forth a lot. “Never saw you here before. You thinking of signing up?”

Jolene acted as if she did not notice the large woman up until now. “Oh, hello,” Jolene said to her. “Yes, I was interested. I’m trying to watch my weight.”

The woman licked her upper lip and smiled. “Yeah, I can see why. Listen, tell the front desk you know Carol, and I’ll get you your first three months off for a yearly membership.”

Jolene’s mouth went went. “Wow, really?”

“Yeah,” Carol replied. “Hey, who knows? Maybe you’ll look like me someday. Check it out.” Carol flexed a bicep right in Jolene’s teen porno face. “Go ahead.”

Jolene reached out slowly and stroked the veiny muscle. “Wow,” Jolene said admiringly. “I must admit, that is impressive.”

Carol smiled and put her hand on Jolene’s lower back. “Stick with me, girl,” she whispered into Jolene’s ear. She walked off and went to do her bench press, pushing off a smaller man as she racked up.

Jolene had a shudder as she pivoted and walked toward the front desk. She figured she would take Carol up on her generous offer and sign up. The attendant was able to help her out, and the discount was genuine. Jolene decided she would come by tomorrow and try out the facilities. Her muscles were still sore from lugging in all of the boxes.

Jolene realized that she had almost no dishes due to a bit of a clumsy spell on her part, so she went to the department store to get some new plates. She was in the housewares aisle, bending over to examine patterns, when she felt a presence nearby.

“Whoa,” said the figure in a low voice.

Jolene sprung up and looked to find a slender young man in a red smock holding a pricing gun. He looked terrified when Jolene locked eyes with him.

“Oh, hi!” Jolene gave a soft smile. “I’m glad you’re here. It says these are thirty percent off. Can you be a lamb and check that for me?”

The young man kept staring as he got his price gun and bent down to scan the barcode. “Uh…yeah, it’s just like you said.” He got up again, still staring at her.

Jolene rested her hands on her hips and slunk to one side. “Well, aren’t you helpful…” She examined his nametag. “…Craig.” She held out her arms. “I’ll just take those, then.”

Craig mechanically handed over the box of dishes. Jolene accepted them, then gave a smirk. “Why, Craig! If I didn’t know better, I would swear I was making you nervous.”

Craig stood frozen. Jolene looked him up and down. He was cute enough, with puffy brown hair and a bony face. “Sorry,” Craig finally managed. “I mean…I just think you’re, like, super-hot.” He grew red. “Oh man.”

Jolene’s mouth fell open. “That’s adorable!” She reached out and gave his bicep a quick squeeze. “You know what? That’s so refreshing when men get to the point. I think you’re very attractive, too.” She leaned in. “May I ask how old you are?”

“I’m twenty,” replied Craig.

Jolene laughed. “Well, as you can probably guess, I am not.” Jolene’s Texan drawl tended to come out when she got flirty. “Are you normally attracted to older women?”

“Um…sometimes, yeah,” managed Craig. Jolene could see he was getting aroused.

Jolene got a pen out of her purse. She took Craig’s hand and wrote her number on it. She folded up his hand and gave it a seductive rub. “You go ahead and call me.”

Craig backed up and left without a word. Jolene giggled as she watched him walk away. “Harmless,” she said to herself as she checked out the wine glasses.

Jolene spent most of the week getting settled in. Her new job was in a high rise in the downtown, and she got along perfectly with almost everyone there. Jolene shared the office with Brooke, and she was delighted to have someone who liked to chat in between calls.

Jolene also made her way into the gym most nights. She saw Carol on Tuesday, who wanted to talk with her for a long time.

On Thursday, Jolene got curious about some of the weightlifting and strength training equipment. She found a chin-up bar and jumped up, holding on and swinging back and forth. She strained and grunted, pulling herself nearly to her forehead before she dropped down. She panted and put her hands on her hips. She could hear laughing close by, and she figured they were going to make a joke at her expense anyway. It was no difference from when she was trying to lose all the weight in the first place.

“Hey, are you using that?” asked a timid voice.

Jolene turned and saw a short, chubby Asian girl standing about twenty feet away. She looked as if she regretted asking.

“Oh, I’m sorry, dear,” replied Jolene. “Would you like to try?”

The girl walked over and jumped up, grabbing onto the bar. She rocked back and forth just like Jolene did.

“Wait, let me steady you,” offered Jolene. She reached up and held onto the girl’s waist while she pulled herself up. Jolene was careful to exert only a little force to help herself lift up. The girl got four reps in before she got down. She exhaled and smiled.

“Thanks so much!” she said to Jolene. “I’m Katie. Katie Yang.”

“Jolene Wyman,” she replied, extending her hand. Katie shook it and looked over Jolene’s body. “God, you must be here all the time. I just started a little while ago.”

Jolene put her hand to her chest. “Oh, no! I just started here, too! I moved here from Texas.” She held out her hands and looked down. “This took a lot of work to get me here.”

Katie sighed. “I hope I get close to where you are. You’re really pretty.”

Jolene gasped. “You darling thing! Well, let’s work out together for a travesti pornp bit.”

Katie and Jolene trained hard that evening. Katie built up a bit of a sweat, mainly trying to exert herself to show Jolene her commitment. The two of them wrapped up and hit the locker room.

“I think I’ll shower at home,” commented Jolene as she went to her locker.

“Yeah, that sounds smart,” said Katie, her locker a few down from Jolene’s. “I mean, I feel self-conscious in there.”

“Katie, dear, you need to feel confident all of the time. It’s a trait that permeates every aspect of your life.” Jolene sat on the bench and threw her leg over to straddle it. “I was chubby for a long while. I know how it feels. Most of these fears are the result of your own outlook. Plus, there are trade-offs when it comes to weight loss.” She reached up and jiggled a boob. “See how small these are now?”

Katie laughed. “Yeah, but you’re still hot.”

Jolene crooked up a corner of her mouth. “Well, I do all right.” She got her cell phone out of her bag. “Please let me know your number. I’ll want to chat with you later, okay?”

Katie gave it to her and Jolene entered her in as a new contact. “I’m afraid I will be indisposed Friday, but we’ll get together soon,” Jolene promised.

Katie gave Jolene a huge hug.

On Friday, Jolene took Craig out to a Mexican restaurant. She assumed he would be more relaxed at something less formal. He seemed jealous of Jolene, who was able to enjoy a margarita.

The two of them went back to her place. The only furniture she had available was her old couch. “Come in! Sit down!” Jolene led Craig by the hand and got him relaxed. “I’m sorry, but I don’t even have a TV yet. All my other furniture came with the apartment.” She rubbed his leg. “The bed is ready, however.”

Craig stared at her with a scared look. Jolene patted his shoulder. “Darling, relax,” she said. “You have a look as if I was about to assault you.”

“Oh! No!” Craig straightened up. “I’m just nervous.”

“Well, as am I, Craig,” Jolene giggled. “There. Now we have much in common.” She rubbed his leg again as she felt her eyebrow twitch. Her legs were starting to sweat. “I haven’t done much of this, either. Not since my divorce, anyway.”

“Oh, I’m sorry,” said Craig. “How’d that happen?”

“He was a very mean man,” Jolene replied. “He liked to insult and hurt me. Look.” She leaned in and ran her finger along the side of her cheek. “You see how he scarred me?”

Craig squinted. “Oh, yeah, now that you mention it.”

“This is why it’s important that you never hurt me, Craig,” Jolene said with a stern tone. “I am very vulnerable right now. I need a great deal of comfort.” She leaned in and moved her hand all the way up his leg. “Can you provide that comfort, Craig?”

“Yes,” whispered Craig.

“Do you like older women?” asked Jolene. Craig nodded. “I am so delighted to hear that. See, I am a true believer that every man deserves at least one woman in his life that he can remember fondly, that was able to mentor him in the ways of love. Someone with experience, someone willing to try bold and exciting things.” She leaned in and kissed his cheek, then stroked his chest with the back of her hand. “Will you be my boytoy, Craig?”

Craig looked fit to explode. “I’ll do anything you ask.”

Jolene smiled. “This is incredible!” She took Craig by the back of the neck and kissed him. Craig was an anxious kisser, and his hands were all up and down Jolene’s body within seconds. Jolene felt up his chest as the two of them locked lips and panted.

Jolene pulled her head away. “Okay, darling. Now is the time where I bring you pleasure.” She slid off the couch, then reached in to unzip Craig’s pants. Craig was eager to get things started and helped with sliding his pants and underwear off.

Jolene took her time examining the penis. There was a little discoloration on it, but Jolene paid no mind. He was trimmed up, which she had noticed a lot of young men were doing these days. She took the head into her mouth, slurping and letting her tongue play along the top. She also enjoyed playing with the balls. She knew to be gentle and slow with them.

Jolene’s head pumped up and down while Craig leaned back and enjoyed the experience. He placed his hand on top of her head, but she gently pushed it away. “I can manage,” she breathed while she went back to sucking. Her head bobbed up and down while she held onto the shaft.

Jolene had a special technique of rubbing her thumb tip up and down along the underside of the cock. Craig was losing his mind, giving himself gentle slaps in the face in disbelief. “Oh my God, Jolene! I never felt like this before!”

Jolene reached down and rubbed at herself through her panties. Her skirt was hiked up enough so that Craig had a good look at her whale tail. He wanted so badly to grab a handful of that cute ass. Jolene took the cock with both hands and sped up the blowing, her nose exhaling with every pump.

After five minutes, Jolene pulled the tricky masseur cock out and held it to her face. “I am glad to see that you have a little endurance.” She stood up and unbuttoned her blouse, getting down to her bra. “Did you bring protection, dear?”

Craig winced and put his fists to his eyes. “No!”

Jolene tittered. “I have some, silly. Will you please escort me to the bedroom?”

Craig got up, and decided to just kick off his pants. He took her hand as the two of them walked down the hall. When they got to the bedroom, Craig yanked off his shirt and his socks. He stood there and held out his palms.

Jolene took her time examining him. “Why, you are such a handsome young man,” she purred. She undid her skirt and let it fall to the floor. She stood there in a black lace bra and matching panties while her hand ran up and down her torso. “Do you like me?”

Craig stumbled for words. “I like you so much, Jolene.”

“Oh, I’m relieved to hear that.” She walked toward him as she undid her bra and let it slide off of her. Craig gasped when he saw her breasts. Jolene took him by the shoulders and kissed him. Craig reached out and felt up Jolene’s tits. He was rougher than she was have liked, but she deferred to his curiosity.

She pulled away, their lips making a huge smack as she did so. “In the nightstand, dear,” she whispered.

Craig went over and opened the drawer, then got out a condom. He tore it open with his teeth, then struggled to get it on properly. As soon as he was ready he jumped onto the bed, his erect cock swinging back and forth with the pink condom on.

Jolene slid off her panties. Her pussy was trimmed up nicely but she preferred a little hair. She strolled over and laid down next to Craig and sucked his dick. She allowed her hands to roam up and down his smooth torso as she blew him. Craig sounded in bliss.

Once she was satisfied that he was full hard, she got up and positioned herself on top. She steadied herself while she let the cock find its way up to her labia, then pushed down to get it into her. After the initial pop, the cock pushed through into her vagina. She bit her lip and squealed as she felt that warm cock glide up into her.

She placed her hands on Craig’s chest as she pumped herself up and down. Jolene’s heavy breathing was all that could be heard in the house. “Are you enjoying the sex?” she asked.

Craig held onto Jolene’s thighs as she fucked him. “Uh huh. This is so awesome!”

Jolene bared her teeth as she grunted. “I’m glad you’re happy, dear. Oh, this feel so nice.” She stroked his face while she pumped up and down. “A woman needs to feel beautiful once in a while.”

“Man, I can’t believe you wanted to fuck me,” Craig said, smiling.

“Language, dear,” Jolene scolded. She got off and got on her back, lifting her legs up. “Please lick me.”

Craig got down and licked away. Jolene was not thrilled with Craig’s technique, but she laid back and tried her best to enjoy it. “Darling, slow down a bit.” Craig did so, and Jolene closed her eyes and smiled. “Much better.” She placed a tender hand on the back of his head.

After several minutes of his licking session, Craig got up on top of Jolene and pushed himself into her. Jolene held onto the boy’s shoulders as she felt the intense squeeze of his penis working his way into her. Once inside, he sloshed in and out of her. The two of them held each other and kissed as Jolene squealed and moaned into his open mouth.

“Oh my God!” Craig’s face was red and sweaty from the intense labour. “Why are you doing this for me?”

Jolene had her eyes squeezed shut. “No! It’s…for me! Unnnh! You’re going to…help me…with…” She lost her train of thought as her orgasm built up. Craig froze while he watched her writhe and twitch, still inside of her.

“Oh my!” panted Jolene. “Oh, let me finish you off, dear.” She pulled at the condom on Craig’s cock. Craig unrolled it, and Jolene sucked at it and stroked his balls. Craig tensed up after a minute as the hot load came out. Jolene had pulled the cock out of her mouth in time to feel it spray across her face. Craig toppled over as Jolene let the hot mess sit on her face and run down her neck.

Jolene rubbed at the slime with two fingers, then has a taste. “Mmm,” she remarked. She got up to go wash off while Craig laid there in bed. Jolene looked at herself in the mirror. She was glad that her black hair was cut so short. She got scrubbed off, using her special face cleanser. Once she was satisfied, she went back to the bed and sat down.

“Now there are some rules you must abide to, darling,” she mentioned. “First, you are not to call me for any reason. I will call you when you are required.”

Craig sat up, his dick resting to the side. “Uh, all right.”

“Second,” continued Jolene. “When you are here at my house, you are to do exactly as your are told. This is my private home, and I will not be made a fool of here. Is that clear?”

“Yes, ma’am,” said Craig timidly.

Jolene smiled, linking the response. She had picked well. “Third, I am neither your mother or your girlfriend. Under no circumstances am I required to buy you gifts, take you places, or meet any of your friends. I am in control of this arrangement. Is that perfectly clear?”

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