The following is a sexy short story that was partially inspired by some real-life anecdotes about men coping with loss with the help of sex workers. A good portion of those stories came from men who had served in the military and in the spirit of Memorial Day, I wanted to capture the beauty of those experiences.
Whether you’re a veteran or just someone who has had to find ways to cope with loss, I hope you can appreciate this. Enjoy!
“The first Thursday of the month,” Reyna Stanly said to herself, “the best day of any month in my otherwise fucked up life.”
The young woman carried herself with more energy than usual and for good reason. It was a welcome day of contentment, especially for a professional escort. As someone who lived a life of ever-evolving risks and obstacles, she understood the value of those days better than most. After the week she’d endured, she needed one.
Having arrived at the mid-level hotel a half-hour ago, Reyna made her way up to the eighth-floor suite, as she’d done many times before. She wore the same low-cut black dress that she’d worn for the past several encounters with the special client that awaited her at the end of the hall. It wasn’t too sexy. Most people who saw it wouldn’t associate it with an escort or sex worker. Walking through the lobby, she looked like someone on her way to a dinner party at an overpriced restaurant.
Compared to what most clients asked her to wear, it was a welcome touch style. It made her feel like she was playing a role rather than providing a service. For the client that awaited her – a very special, very important client that she’d come to cherish – she took great pride in playing that role. It meant almost as much as her as it did to him.
“If only everyone in my life appreciated my dedication as much as you, Willie,” Reyna sighed as she approached the door.
As she prepared for the not-so-typical job before her, she lamented that the most decent male role model in her life was someone she’d met while escorting. It would’ve been hilarious if it weren’t true, but from where she came from, role models were hard to come by.
Her father had walked out on her mother and sister when she was six. After that, her mother went onto date a string of loser guys, eventually marrying one who could help pay off her gambling debts. It hadn’t been out of the goodness of his heart, though. That man, who she still refused to call her father, only kept her out of debt so she wouldn’t give him any crap out about cheating on her.
Her older sister followed a similar path, attracting all the wrong men before marrying the one who got her pregnant in high school, albeit after some heated coaxing. Theirs was not a stable marriage, to say the least. They fought more than they loved, cheated on each other so often that Reyna could practically set her watch to it. She escaped that environment the first chance she got.
However, her judgement hadn’t been that much better than her mother or sister. In high school, she’d played the part of the class slut, hooking up with multiple men and having a long string of empty relationships. Most of that was her way of staying away from home, but it came at the price of attracting men who cared more about easy sex than genuine intimacy. Whether by bad luck or family tradition, Reyna and her family never seemed to cross paths with the kind of men who were worth loving.
“Guess that’s more my fault than yours,” she said under her breath, lingering at the door as she checked her phone. “You were just looking to mend a broken heart. I was looking for easy money. Now, here I am…needing you as much as you need me.”
It was tragic, but oddly fitting. She’d gone most of her life knowing few good men. Then, she left home, got into a local college, and started making her own money as an escort with the goal of never having to rely on a man. Willie Mavin didn’t necessarily derail that goal, but he certainly complicated it and for all the right reasons.
As she knocked on the door, Reyna felt like needed to affirm those reasons. Having had so many poor influences on her, she had to cling to the few good ones she still had.
“Come in,” said the familiar voice from inside the room.
Smiling for the first time all week, Reyna entered the room and into her role. At that moment, she was no longer Reyna Stanly, the trashy young woman who made her living as a whore for men with no time for a mistress. She became Mandi, the affectionate young woman who reminded a lonely man of better times.
“Mandi,” said a tall, lanky, middle-aged figure sitting on the bed, “you’re as stunning as ever.”
“You’re too kind, Willie…way too kind,” she replied in a voice that blurred the lines between fantasy and reality.
Upon closing the door behind her, making sure to lock it and place the “do not disturb” tag on the handle, she set aside her purse and made her way to king size bed where her favorite client awaited her.
“I’ve missed you,” she told him, mixing the traditional script of an escort with honest sentiment. “You make the first Thursday of every month something I look forward to.”
“So do you,” said Willie as he gazed at her with that loving admiration.
“This past month has been especially tough. I need this as much as you do.”
“I believe you.”
She’d heard that from men before, pretending they could empathize with her plight. She rarely believed it, especially from clients. However, Reyna made an exception for Willie.
She also made an exception when it came to embracing a client. She didn’t just stand in front of him, posing like a model in hopes of tempting him into paying for another hour. She immediately joined him on the bed, slipping into his arms and sitting on his lap. She barely even noticed the empty envelope containing her payment on the nightstand. Willie never short-changed her or abused her trust. Very few men in her life could make such a claim.
“You seem tense, Mandi,” he said as he slipped an arm around her waist and caressed her face. “Is everything alright?”
“It is now,” Reyna replied with a reassuring smile. “Try not to worry about me. I’m here for you, remember?”
“You make that difficult to forget,” Willie said as he smiled back.
“Then, I must be doing my part exceptionally well.”
“You do more than that, Mandi…much more.”
He embraced her closer, holding her as he would a cherished lover. He was so affectionate and tender, kissing her neck and taking in her scent, which she’d augmented with her best perfume. It was enough to get her heart racing as she returned his affection, wrapping her arms around his neck and drawing him deeper into her intimate warmth.
Reyna knew how it must have looked from an outside perspective. Anyone observing them at that moment wouldn’t have seen anything other than a tall, slender man in his late 40s with graying hair holding a young female escort in her early 20s. It had all the qualities of a typical encounter between a sex worker and an older man. She wouldn’t have blamed anyone for seeing it as anything other than some guy wanting to get frisky with a cute young woman.
However, there was much more at work than a man willing to pay for sex and a woman willing to accept money for it. Some of it showed in the clothes he wore. Like her, Willie wore the attire that evoked his fondest memories. That included a neatly-pressed dress shirt with military emblems, a clip-on tie, and navy-blue slacks that had just been dry cleaned the other day. It gave him the presence of a man who knew how to take care of himself and valued how he presented himself to others.
He’d learned that skill in the military and still carried himself like an honorable, disciplined soldier. That kind of ability and self-respect did plenty to set Willie apart, but those were just the most obvious qualities she admired. The rest ran much deeper.
“This week has been especially lonely,” Willie said after he finished kissing er. “It would’ve been our wedding anniversary on Monday. My son tried to visit so we could spend some time together, but his flight got cancelled.”
“I’m sorry to hear that,” Reyna said. “I hope he makes it up to you.”
“He will. He’s a good young man, just like his brother. I’m not worried about him. I’m just focused on you…on us.”
“And I intend to do nothing less.”
True to her word, a trait any competent escort valued, Reyna dove deeper into her role. Caressing his unshaven face with both hands, she kissed him with a soft, but sensual passion on the lips.
It was not the kind of kiss she shared with other clients. It was genuine and loving, akin to something a dear lover would give to someone who they’d missed. Almost immediately, it had an impact. She sensed his tension settle. The rugged, manly musk of her breath helped her settle too.
“My darling, Mandi,” Willie gasped with an intensity few men dared to show, even with an escort.
Her heart skipped a beat. She still wasn’t used to that, especially with a client. Reyna wasn’t sure she wanted to get used to it. The way Willie held her and the way he kissed her triggered something in her that she didn’t think she could feel for a man, even before she became an escort.
As the kiss deepened, those feelings intensified. Before long, a kiss was no longer sufficient.
“Willie…sweetheart,” Reyna said, now deep into her Mandi persona.
“Yes, Mandi?” he replied, already breathless.
With a coy grin and the taste of his lips still lingering, she broke the embrace and turned around so that he could see the back of her dress.
“Would you please unzip me?” she asked him. “This dress feels so…burdensome.”
“Of course, my dear,” Willie replied without hesitation.
Like a gentleman, he did as she requested, unzipping her dress with the utmost care. He wasn’t like some horny guy eager to get a girl naked. He was so careful, highlighting every inch of newly exposed flesh.
Once he reached the bottom of the dress, she stood up and let it fall off her body. In doing so, Reyna revealed she hadn’t been wearing a bra. Upon stepping out of her dress, kicking off her heels in the process, the only article of clothing she had left was a pair of black lace panties. When she turned around, giving him a perfect view of her feminine features, the awe in his eyes was profound.
“Wow,” said Willie in a daze. “You’re as beautiful as I remember…a sight I never get tired of.”
Reyna just smiled curtly as he gazed upon her, leaning back on his arms and taking in every feature. He’d seen her naked many times before, but she knew Willie wasn’t just referring to her natural beauty when he saw her voluptuous form. In his eyes, he wasn’t looking at Mandi, the escort he paid for a night of intimate company. He was looking at Mandi, his deceased wife.
“I miss you…so much,” he said with a hint of sorrow in his tone.
“Oh Willie,” she said, “I’m here now, aren’t I?”
That was only half-true. She knew she wasn’t Amanda, the woman he’d married right out of high school and loved with all his heart until she succumbed to cancer. He had to know that too, but it didn’t matter at that moment. As far as they were both concerned, the harsh reality of their respective lives didn’t apply within the walls of the hotel suite. For just a brief moment, they could enjoy a quiet moment of intimacy.
“You’re here,” Willie said, tears already forming in his eyes. “God, I want you.”
“I want you too, Willie,” she told him.
Her role made room for her skills as an escort. With a seductive poise that she’d refined from her promiscuous past, she slipped back onto his lap, straddling his waist and grinding her groin up against his pelvis. That got the blood flowing to the lower half of his body. It also prompted a flood of amorous affection.
“My sweet, Mandi,” he gasped. “My sweet, beautiful Mandi.”
It was tough to maintain that seductive mood when he was so loving with his gestures. Willie was always more tender than most of her clients, but there was something different about the way he touched her exposed upper body. He playfully fondled her breasts, buried his face in her neck, and traced his fingers down her waist and hips, as if to paint an image in his mind.
“Mandi…I see you,” Willie gasped as he kissed her.
“So do I,” she whispered into his ear.
The foreplay quickly intensified. As Willie felt around her exposed upper body, she began loosening his clothes, removing his tie and unbuttoning his dress shirt. It played out like so many other encounters she’d experienced with clients, but there was deeper story unfolding between them.
Reyna had come to know the details of that story well. Since he became a regular, she’d learned a great deal about the role she played. Amanda Mavin, the woman Willie saw whenever they were together, was a very different woman than the one she’d become. She wasn’t just a loving mother and supportive wife. She’d been a gifted artist, a college professor, and an adventurous traveler.
Willie claimed she saw the world as a work of art worth admiring and exploring. She’d taken him to so many wonderful places, sharing so many passions along the way. After serving in the army, spending time in war zones and seeing so many awful things, he needed that. She helped him see and experience beauty in the world again.
When Willie first told her about Amanda, she laughed at the notion that she had anything in common with her. She doubted they even looked alike. Then, he showed her some old pictures and the resemblance was undeniable. When he told her about the kind of spirit she had and how she’d overcome a less-than-ideal upbringing, Reyna saw more and more similarities. It made the intimate experiences they shared more meaningful.
For Willie, it was a way to reconnect with the memory of a woman he loved and missed dearly. For Reyna, it started as her providing comfort and sex to a lonely widower. It soon became as therapeutic for her as it was for him. After the week she’d endured, she needed that therapy more than usual.
“Willie,” Reyna said in the midst of all the affectionate touching, “lie down on your back.”
“Of course, my darling,” he said in that deep, loving tone of his.
Having rekindled old memories and the passions connected to them, she pursued the escalating desire. After guiding him towards the center of the bed, he laid down and kicked off his dress shoes, allowing her to go to work.
She channeled more of Mandi’s spirit, removing his dress shirt, undoing his belt, and taking off his slacks. She took her time, kissing down his chest and pawing his arms. He once told her that Mandi treated lovemaking like a work of art, requiring exquisite detail and impassioned vision. Reyna never saw sex in such a colorful way, but she quickly came to appreciate that approach. Upon removing the widowers underwear, she saw how much Willie appreciated it as well
“Wow! You did miss me, Willie,” Reyna said coyly while eying his semi-erect manhood.
“What can I say? Certain parts of the human body say more than words ever well,” Willie said with a playful grin.
She smiled back at him before channeling more of that sexy spirit. She briefly hovered over him, allowing him to admire her body even more. She even dangled her breasts in his face, something he once said Amanda loved to do during intimate moments. He also once mentioned she loved it even more when she gave his penis a quick lick to prepare for their sex. With most men, Reyna would’ve assumed that was just a creative way to get oral sex. With Willie, she trusted his word.
Like a sexy angel, she lovingly kissed his lips before sensually working her way down his body. Willie kept in great shape for a man his age. All the work and travel he did with his late wife really paid off. That extended to his penis, which was already throbbing by the time she reached it.
With skilled hands and talented lips, she gave the widower a quick round of oral teasing. She was more careful than usual, sucking and stroking his member while looking up at him with affectionate eyes. It evoked a familiar, yet rewarding reaction.
“Oh Mandi…my love,” Willie moaned.
She replied with more sucking, bobbing her head up and down, making full use of her oral sex skills. Seeing the older man so happy and impassioned was a nice personal bonus and one she didn’t get with most clients. It motivated her to share in the feeling, as well. As she sucked him off, she reached into her panties and fingered herself, building up her own arousal.
As soon as she got him fully hard, she rose up from the bed and removed her panties. She also retrieved a condom that she’d stashed inside, a trick that only the savvy, most cunning escorts could pull off. After opening it and applying it to his rigid manhood, they were ready to complete the moment that they’d both come to appreciate.
“I’m ready for you, Willie,” Reyna said to him as she got back on top of him.
“Please, Mandi…I need you,” Willie said, reaching up and caressing her face.
It almost was sad, hearing the longing in his voice. She saw in his eyes how much he wanted to cling to the memory of his late wife. Even if she wasn’t that woman, he yearned to turn those joyous memories into an experience…one she could share with him.
Eager to share something so loving and intimate, Reyna positioned herself over him, straddling his waist and holding onto his torso. She locked her eyes on his, doing her best to mimic the loving gaze his wife must have given him for so many years. Then, as he slipped deeper into his memories, she lowered her hips and guided his manly flesh into her.
“Ooh Willie!” Reyna moaned out.
She was more vocal than usual, but for all the right reasons. The way he filled her depths, her womanly folds embracing his rigid manhood to the utmost, filled her with more than just the familiar sensations of sex. It turned an act of basic sexual intercourse into a truly intimate act.
“Mandi…my sweet, sweet Mandi,” Willie said joyously.
“I feel you, Willie…so deep inside me,” she gasped.
Now lost with him in the feeling and the fantasy, Reyna began moving her body in a succession of slow, sensual motions. They didn’t rock the bed or strain their bodies with their sex. There was none of that crude, mindless humping that she’d experienced so common with other clients. She put real, genuine passion into their sex.
“I need this…you need this…we need this,” Reyna found herself saying in the midst of their movements.
Having established a steady rhythm, she leaned in and kissed him lovingly, allowing their naked bodies to fully mesh. The widower returned the favor, throwing his arms around her and grabbing hold of her butt, something she’d always loved during sex. It allowed him to supplement her sensual movements with his strength, evoking more blissful sensations and deepening the intimacy.
That was a big part of what made Willie her favorite client. He made their sex – the same sex that she once treated as a simple means to an end – a truly intimate act. She thought she knew intimacy from her previous boyfriends. In serving Willie, she realized those experiences were just lust, hormones, and the pursuit of meaningless pleasure. There was nothing meaningless about what she did with Willie. It might have been the most meaningful part of her otherwise hectic life.
“That’s it, Willie…make love to me,” she whispered to him. “Make sweet, beautiful love to me.”
“I will, Mandi! I…I will!” he said eagerly.
He kissed her more passionately as she rode him with focused intent, working his rigid manhood within the moist depths of her inner domain. As he squeezed her butt, she reached down and fondled her swollen clit, wanting to share the pleasure with him. It further intensified the intimacy that they both so cherished.
As they embraced the feeling, Reyna also shared in the sensual efforts. She got a bit more playful at times, leaning back and swaying her body in a sexy dance, of sorts, that earned her a beaming smile from Willie. He did his part as well, gliding his hands over her naked flesh, making sure to give her nipples some extra attention, knowing how much she loved it.
Each movement and gesture had a purpose.
Each intimate act took them closer to their goal.
Slowly, but surely, they ascended towards their respective climax.
As it drew near, Reyna shifted their bodies so that Willie was on top, working his hips with hers with energy not topical of a man his age. She held onto his shoulders, spread her legs extra wide, and locked her eyes with his once more, urging him to finish the experience.
“Oohhh I’m close, Willie! I’m so…so close!” she told him.
“Me too, Mandi! Me…too!” Willie said with labored grunts.
“Just…just a little longer. I want us…I need us…to share this.”
For a brief moment, Reyna broke character. It might have been the first time she’d ever blurred the line between the woman she was and the woman she pretended to be while escorting. It was something she’d been taught to avoid, entangling such sentimental feelings with sex work. It might have been risky, but in that moment, it felt so right.
“Mandi…my love,” the older man gasped as he neared the threshold.
“Willie,” was all she got out before following him into that world of ecstasy.
A few more shared bodily motions was all it took. When the feeling washed over them, time seemed to stop as the line between memories and roles vanished.
It wasn’t a simultaneous climax, but it was pretty damn close. Willie got his first, letting out a sharp gasp as his grip on her hips tightened in accord with his release. Feeling that hard, throbbing flesh inside her along with the heightened intimacy helped send her over the edge as well. While Reyna had gotten fairly adept at achieving orgasm with clients, she usually had to make a concerted effort. She didn’t need much when she was with Willie.
With him, the release came to her. His heartfelt sentiment took her to that special place where ecstasy took a tangible form, each sensation reverberating through her like a wave of heat. It caused her back to arch and her toes to curl, ruffling he bedsheets every step of the way. As always, she savored every minute sensation. Unlike every other orgasm she’d experienced as an escort, the one she shared with Willie left her feeling uniquely fulfilled.
“Willie…thank you,” Reyna said in the heat of the moment.
“Mandi…I miss you,” Willie said in his orgasmic daze.
She lingered in that daze with him, if only to escape a much harsher reality with him. She kissed him and embraced him again, even after he withdrew from her and laid down beside her. Their naked bodies remained entwined as the afterglow set in. Reyna already sensed the time he’d paid for running out, but she didn’t care. She didn’t even check the clock. Escort or not, she needed that special, intimate moment with him.
“Thank you,” the older man said, still catching his breath as he held her in his arms. “I know I make things awkward…mixing memories of my wife with what we do.”
“Don’t you dare apologize,” Reyna told him, daring to cuddle closer with her favorite client. “You loved her. You miss her. And based on all the times we’ve done this…I can tell you two were pretty passionate.”
“We were. It’s one of the many things I miss about her,” he said with a sigh, “but those intense, intimate moments we shared over the years…I miss those the most.”
“That’s how you know your love was real. Not everyone gets to experience that kind of love, let alone appreciate it. You wanting to relieve it, even its with an escort who just happens to look like her, isn’t the least bit awkward. It’s sweet.”
“I’m glad you appreciate it.”
“Believe me, Willie…I appreciate it more than you’ll ever know.”