Jolene's Trip to Vegas

Jolene, clad only in black lace stockings, grabbed her phone and walked past their unexpected guest on her way to the hotel bathroom. Semen dripped down her inner thigh as she observed her reflection and texted her boyfriend.

Matt's cock jumped as he read the long-awaited message. It had been an hour since her last call.

"How was it?" he asked via text.

Jolene replied with a freshly fucked, mirror selfie. Her hair was messed, her makeup smeared, and the petite brunette's body still glistened with perspiration from the night's activities.

"Where did he cum?" her boyfriend inquired.

"Where you wanted," she texted back.

Matt's hand gripped his throbbing erection as his free hand fumbled with his phone.

"You're such a whore," he managed to type.

"His friend just got back to the room," she informed Matt. The image of Jolene with two men was too much for him, and streams of cum spurted from his tortured cock and across his belly.

"Should I get dressed and leave?" she asked teasingly. Matt's hands trembled as he typed.

"Does he want to fuck you too?"

Jolene knew the answer as she looked at her smiling reflection in the mirror. While she had just turned fifty, her gym-toned body belied her age. Her perky but fake 36D breasts were perfect for her 5'2" petite body, and her straight dark hair hung just past her silky white shoulders. Her flat tummy showed no indication of motherhood, and her neatly-trimmed pubic hair matched her sexy, black laced stockings.

"What do you think?" she asked rhetorically.

Matt cum-covered belly burned as he pondered the possibilities.

"You should stay," he managed to reply.

"If that's what you want," she texted, knowing full well that a threesome would be the perfect ending to this evening for her, and the opportunity was waiting just outside the bathroom door.

"I'll text you when I can."

With that, she exited the bathroom and was greeted by the two smiling men who were now chopping up lines of cocaine on the hotel dresser...

Sarah, Jolene's best friend, had planned a weeklong getaway to celebrate her fiftieth birthday. Jolene's divorce had only been finalized six months before this landmark. She had been exploring bars and dating sites and had found several men with whom to explore her new-found freedom. A week in Las Vegas with four girls was a perfect opportunity to enjoy some debauchery. Cindy and Jane were married but weren't shy about expressing their desire for a discrete encounter during the two-hour car ride. Sarah was the only single girl on the trip, but Jolene had complete and enthusiastic permission from Matt to engage in whatever activities she desired.

"You're gonna get fucked down there, aren't you?" Matt asked as she was waiting to be picked up. They had been casually dating for a few months after meeting at a local bar. A few drinks, some conversation, and an evening of dancing led to a trip back to his apartment. She loved how he aggressively took control of her delightful little body; pulling her hair, smacking her ass, and reminding her what a slut she was before ramming his big cock up her virgin ass. Twenty-five years of married sex hadn't prepared her for a lover like this, and she was enamored. Jolene was also pleased to discover that he had no expectation of faithfulness. Quite the contrary, Matt encouraged her to take other lovers. On a few occasions, she would leave a man's house and drive directly over to Matt's and allow him to add his load to the one already in her pussy.

"I'll see what I can do," she teased. Both knew the answer to that question. They had spent the previous day shopping for sexy outfits and undergarments for her trip to sin city. Some lucky man or men were sure to enjoy stripping them off her. There were only a couple of rules. She had to get fucked in her ass, and there were to be no condoms.

The first nights went quite well for Jolene's companions. Sarah and her date had monopolized the room the first night while Jolene, Cindy, and Jane occupied themselves at the casino. The next night, all three had found another room in which to stay, leaving Jolene alone and masturbating to ordered porn. It wasn't terrible though. She had Matt on speaker phone while she watched ten black men ram their gigantic cocks into a tiny, blond European girl who couldn't have been more than twenty years old. The camera zoomed in on the cocks driving into her pussy and ass before moving around to her face. The young starlet's expressions and moans looked more like agony than pleasure as the group relentlessly used her body. Matt listened to Jolene as she came several times while describing the action as if she was the girl.

On the third night, the girls were readying themselves to attend an event at the attached nightclub while recounting the previous night's activities.

"His friend was in the other bed pretending to be asleep, but I know he was watching us," remarked Cindy.

"You should've asked him to join," Jane laughed. "My guy told his friends to keep gambling until he was done. I wish they would've walked in."

"What would your husband say?" Cindy teased.

They all laughed and agreed on the cliché about what happens in Vegas stays in Vegas.

"He wanted to fuck me without a condom!" Sarah revealed. "Can you believe that? Who would fuck a stranger in Vegas without protection?" Jolene nodded in agreement while knowing that as per her and Matt's agreement, any man she fucked would be required to unload in her.

Her heart fluttered at the thought as she slipped into her evening's attire. She had chosen a tight-fitting, one-piece black dress that ended well above her knees. The lace tops to her black stockings were visible whenever she bent over even slightly. Her four inch heals disregarded comfort in favor of looks, and a lucky man was going to be greeted with a sexy set of lacy black panties and bra once the dress was removed. Her friends teasingly commented on her ensemble.

"You might get kicked out because they'll think you're a hooker," laughed Sarah.

"Every guy there will know you're looking to get fucked," predicted Cindy.

"You look awesome," complimented Jane.

Jolene blushed at their attention as the girls continued to get ready. As they were about to leave, she stepped into the bathroom. Once inside she took a picture of her reflection and sent it to Matt with the message; "tonight's the night." They had both been disappointed in her lack of success so far.

Matt gasped at the image of his sexy girlfriend before replying, asking if she remembered the rules. Jolene smiled as she texted back.

"I'm gonna get fucked in the ass and he's gonna cum in me."

"Hurry the hell up," she heard from outside the door. She quickly texted Matt that she was leaving and joined the group of horny females before exiting the room and heading to the elevator.

The club was loud and crowded as some well-known DJ was providing the music. Once they navigated to the bar, as expected, their drink order was paid for by a male patron. After some conversation with him and his friends, the girls decided it was too early to partner up and headed to the dance floor to explore more options.

Over the next few hours, they danced and enjoyed many free cocktails purchased by the hopeful men in attendance. Jolene had been felt up by several of her dance partners, but none had really excited her. Her friends were doing much better as Sarah had already found a man and taken him back to their room. Cindy and Jane were grinding and making out with their respective choices and were sure to be leaving with them soon. Jolene surveyed the floor before heading to the ladies' room. After waiting on a long line, she finally got to sit down and relieve herself. She took out her phone to see several messages from Matt, inquiring about her prospects.

"I'm not having much luck. Nobody I like," she replied.

"Don't worry. Somethings gonna happen tonight's the night, remember?" he alluded to their previous conversation.

"I remember," she texted, before leaving the stall to fix her makeup. After observing how hot she looked, she left the bathroom determined to find a handsome stranger to spend the night with.

As she walked past a group of tables, fate intervened, and she bumped into a younger man heading towards the bathrooms. After the customary apologies, he asked her her name.

"Jolene," she answered. He was much taller than her. His dark hair and blue eyes complimented each other, and his manner of dress was quite stylish. He looked to be in good shape, and was certainly handsome, but a bit too young, she thought.

"I'm Steve," he offered, attempting to start a conversation. It worked, and they were soon discussing the circumstances surrounding their reasons for being in Vegas. His good friend Mark was getting married, so they and several others were having a bachelor getaway.

"His fiancé must be very trusting," she remarked.

"She shouldn't be," he joked.

After more pleasant conversation, Steve suggested that she join him and his friends. Jolene rebuffed his offer.

"People will think I'm your mother. You're adorable, but I'm going to have to decline."

"What else are you going to do?" he asked, and then reminded her that her room was occupied, and her friends were busy. Jolene realized she may have offered too much information in their short conversation. After a little more convincing, she agreed, and allowed herself to be led to his table and group of friends.

"Hey everyone. Jolene, this is Andy, Rob, the bachelor, Mark..." Jolene forgot the names after that. They all happily greeted the sexy milf before them, and Jolene observed them staring hungrily at her body and provocative dress. She took the seat that they offered, and Steve hurried back to the bathroom, having forgotten his original reason for leaving the table. The remaining three jockeyed for her attention and replaced her drink.

Steve eventually returned and took his seat next to her. Over the next hour Jolene relished in the attention this young group was paying to her. They had travelled from southern California and ranged in age from late 20s to early 30s. They had all attended the same high school and remained friends. Mark, a dark Italian, was getting married in two weeks. Rob was the shortest and funniest, while Andy, a muscular blonde, would be her second choice after Steve. Steve was reading her subtle signs as she played with her hair and repeatedly touched his strong arm.

Jolene jumped a little when he placed his hand on her thigh. He was so young! He was hers if she chose him, and those twenty plus years concerned her less as she continued to consume the drinks he bought her. His friends were oblivious as he inched his hand higher, sliding under her dress and reaching the lacy top of her stocking. She debated pushing his hand away, but instead brushed her hand over his cock which was straining against his pants. With that sign of approval, he inched higher until he felt the wetness of her panties.

"Shall we dance?" he asked. Jolene readily accepted and he took her hand and led her to the crowded dance floor. She looked around, attempting to find her remaining friends, but they were probably already naked in some stranger's room getting fucked. She pondered her own possibilities as Steve became increasingly bold as they danced. He groped her ass and pulled her against him, making sure she felt his erection. Jolene returned his kiss and their tongues intertwined. His hands slid up the back of her thighs, and a few onlookers caught a glimpse of her naked ass and g string.

"I have the suite to myself for a little while," he whispered into her ear. Jolene was ready and nodded in affirmation.

"Give me your room number and I'll meet you up there in fifteen minutes," she replied. After obtaining this information, she excused herself and headed to the bathroom.

"I'm headed to his room," she texted her boyfriend. Matt had been waiting for this message for three days, and he immediately undid his pants and started jerking his rock-hard dick.

"Text me when you're naked," he managed to respond with his left hand. Jolene smiled and put her phone away. She primped herself in front of the mirror, sprayed some perfume, and headed to the elevator. Her heart was beating as she ascended to Steve's floor. The bell rang, the sliding door opened, and she stumbled out, realizing that she had had a little too much to drink.

"It's better this way," she thought as she wandered the hallways looking for his room. Once in front of it, she paused, took a deep breath, and knocked.

"Hey, sexy. I'm glad you could make it. Come on in." He ushered her in with a hand on her backside and directed her to the couch. Jolene accepted the drink he offered her, clinked glasses, and drank to the fun ahead. Moments after he took his place beside her, they were all over each other. They lustfully tasted each other's mouths, gasping as they pawed at the other's body. Jolene pulled at the buttons of his shirt, desperate to remove it.

Once shirtless, Steve stood up and pulled her to her feet. Reaching for the hem of her dress, he pulled it upward, first revealing her delightful panties and then her matching black lace bra. Jolene raised her hands, allowing him to pull her dress over her outstretched arms. Her younger suitor paused briefly to admire his conquest for the evening. Her bra and panties combined with stockings and heels made her look more like a prostitute than a vacationing tourist. Steve found the remote and switched the TV to the hip hop music channel.

"Dance for me, bitch," he ordered, to which Jolene obeyed. The fifty-year-old woman proceeded to gyrate to the music of a younger generation, unclasping her bra and dancing topless. Steve marveled at her tight body and augmented tits. The woman, old enough to be his mother, faced away from him before bending over and sliding her lace thong slowly down her toned thighs, past her calves and to the floor. She kicked her panties aside and turned to face him. The petite brunette, clad only in black stockings and high heels, stood before him, ready to be taken.

Steve approached her, wrapped his arms around her waist, and drove his tongue into her mouth. Jolene accepted his advances before dropping to her knees and fumbling with his pants. Once buckles, buttons, and zippers were undone, she pushed his pants and boxers down, releasing his cock. Jolene paused momentarily to admire its impressive length and girth before leaning in to take the bulbous head into her mouth. Steve kicked off his pants and shoes as he looked down, making eye contact with the sultry milf below him.

Jolene licked and sucked while her tiny hands struggled to grip and jerk his sizable member. Salty precum, which started as small droplets, became more substantial, and she knew he was getting close. Abruptly, she stopped, stood up and excused herself to the bathroom. On her way, she fumbled through her purse to procure her phone.

"Who are you calling," Steve asked, as he stood naked, precum oozing down his shaft. Joleen imagined several possible recipients before admitting her arrangement with Matt.

"I'm texting my boyfriend that I'm about to get fucked," she replied. Steve pondered her answer while analyzing her situation.

"He doesn't mind you cheating?" he asked.

"It's not cheating if he knows," she laughed. "But we have one rule. You have to cum in me," she declared before walking naked to the bathroom, deciding against mentioning anal just yet.

Once in the bathroom, she took a picture of herself in the full-length mirror on the door and texted her boyfriend:

"How do I look? His cock is huge!! Gonna go get fucked now."

Matt jumped as his phone alerted, and his cock jumped as well as he read the message and saw the picture of his girlfriend, naked except for her stockings and heels.

"You're a whore," he managed to reply, before dropping his phone and clutching his dick. Joleen smile as she exited the bathroom.

"So, your man knows your getting fucked?" asked Steve.

"I'm sure he's jerking off right now," she replied. Steve pondered this arrangement very briefly before refocusing on the cheating whore before him. He lunged forward and unceremoniously picked her up and carried her towards his bed. Upon tossing her down, he crawled between her legs and placed the head of his cock against her moist slit. With one thrust, he buried his full length inside of her.

Joleen cried out at this aggressive intrusion into her body. Steve withdrew all but the head, placed her legs on his shoulders, and plowed into her again. Her screams echoed through the hallways as he battered her cervix with his oversized phallus. Again, and again, he slammed into her as she helplessly accepted him. Joleen's pleas for mercy were met with increasing intensity as he drove deeper with each thrust. Her hands pushed against his hips in a futile attempt to alleviate the assault on her body, but the tiny woman was powerless against the much larger man.

Her tight pussy struggled to accommodate his girth and aggression. It was her choice to accompany him to his suite. She had danced for him and stripped for him. Now she was his to use. Joleen's body gradually relented and pain gave way to pleasure. Her mind drifted as she imagined Matt jerking off, knowing she was getting fucked.

"Your boyfriend is good with this?" he asked, as if reading her mind.

"Yes," she gasped, as he bottomed out in her pussy.

"Call him," he ordered before rolling off her. Joleen hopped off the bed to retrieve her phone, delighted that Steve was willing to participate in her and Matt's filthy little game. Her masturbating boyfriend jumped at the sound of an incoming call. Reaching for his phone, he was confused as to why he was hearing from her so soon.

"Hey, baby. What's up?" he answered.

"What do YOU think?" she responded before putting her phone on speaker. "I'm naked in Steve's room."

"Hey, bro," Steve unceremoniously introduced himself. "I'm fucking the shit out of your girl." After divulging this information, Steve directed Joleen to the edge of the bed and bent her over. Her dripping slit offered no resistance as he took his place behind her, grabbed her hips, and drove inside her. As she screamed, Matt gently caressed his cock, not wanting to cum too soon. He continued to listen to his girlfriend's moans and slapping of flesh as he teased his throbbing member.

"He's fucking me so good!" exclaimed Joleen. "His cock is huge!" Matt's grip on his cock tightened as he broke his silence.

"Tell him to cum in you," he ordered.

"She'll call you later," said a male voice before the call suddenly ended. Matt's disappointment was exceeded by his arousal. Jets of semen soaked his strategically placed tissue. Back at the room, his girlfriend's orgasm soon followed. Joleen's fake tits bounced in rhythm as Steve's fingers dug into her hips while he pounded away with increasing ferocity. Sweat trickled down her back, and the satisfied woman looked over her glistening shoulder.

"You gonna fill me up, baby?" she asked, smiling seductively, and licking her lips. This exorcised the last remnant of Steve's control, and Jolene felt his cock swell. Then the younger man emitted an agonized groan, buried himself completely inside her, and flooded her pussy with his gooey seed.

Jolene rested the side of her head on the bed, enjoying the sensation of the diminishing throbbing in her pussy. Her lover's grip on her hips loosened, and his breathing slowed. His wilting erection slipped out of her, followed by a stream of cum down her inner thighs. Steve playfully smacked her ass before offering to refresh their drinks. Jolene concurred, grabbed her phone, and excused herself to the bathroom.

Suddenly, the door opened, and Andy stumbled in. Jolene found herself completely exposed in stockings and heels, standing face-to-face with another member of the young wedding party. With Vegas confidence, she greeted him with a hug and kiss on the cheek before continuing her path to the bathroom. After cleaning up and texting the details and a mirror selfie to Matt, she hesitated after placing her hand on the doorknob.