The following is a sexy short story about love, heartbreak, and finding just the right comfort when you need it. Yes, that comfort is of the sexy kind. Not all of us are lucky enough to find that comfort, but when we do, it’s a beautiful thing. Enjoy!
“It’s not fair. It’s just not fair.”
Cynthia Richardson had been constantly repeating those painful words for two weeks, three days, and five hours. That was exactly how long it had been since her former fiancé, Paul Teller, broke off their engagement. In an instant, a seven-year relationship that began in high school came crashing down. If that weren’t bad enough, the break-up meant having to move out of an apartment she could no longer afford and rebuild her life.
It didn’t happen suddenly. The complete collapse of her world had been building for a while, so much so that her friends and family weren’t too surprised when they heard they were breaking up. Some even asked why it hadn’t happened sooner. Cynthia had been asking that question herself. Unfortunately, she already knew part of the answer.
She’d been wrong.
She’d been stubborn.
She’d been foolish.
That shouldn’t have been possible for the same young woman everyone thought would succeed in spades. Cynthia had graduated high school as an honor student, doing all the right things and following all the rules. She’d put in all the work, taking all the right classes in college and going through all the necessary steps for her career.
She had it all planned out. She was going to become a top analyst an up-and-coming investment firm. She was going to marry Paul, the only man she’d ever dated. She was going to achieve the kind of success that everyone else would envy. Everything was in place. There was just one glaring problem.
“We were miserable,” Cynthia said into the darkened night. “We were so goddamn miserable.”
It might have been obvious now, but she and Paul had gone to great lengths to convince themselves that their love was true. They’d moved in together. They’d built their lives and careers around one another. She’d even defied the wishes of her religious parents and had sex with him. She did everything she thought would ensure their love, but it wasn’t enough.
By the time they’d broken up, she failed to get that promotion she’d hoped for and the company went bankrupt. On top of that, Paul had been seeing someone else behind her back. He claimed he never cheated on her. She even believed him. It just got to be too much. They had to end things and it couldn’t have gone much worse.
Broken hearted, out of a job, and more miserable than ever, she turned to her oldest friend, Lillian Saunders, and her friend, Richard Drayton. She and her husband happened to live in a townhouse less than five miles from her former apartment. Having nowhere else to go and her parents in another time zone, she went groveling to the same friend who had once lived in her shadow. To her credit, she welcomed her without hesitation.
“Of course you can stay!” she’d told her over the phone. “Rich and I are here for you.
Cynthia had smiled when she accepted that offer, but on the inside, she was fuming. Even though she’d known Lily all her life, she never expected to turn to her in her hour of desperation. If anything, she’d expected the reverse.
Lily was once a shy, reserved woman who avoided big crowds. Cynthia had known her since they were kids. She’d never shown herself to be as smart or as capable. From grades to relationships to looks, Lily always seemed to be a step behind. That didn’t stop Cynthia from helping her.
She’d helped Lily come out of her shell as she got older. As a teenager, she became more outgoing. It had been a struggle, so much so that some worried whether she could make it after high school. She ended up going very far, especially after meeting Rich. He was the one that turned her shyness into charisma.
That was quite a feat for someone her father once described as a wannabe hippie who dropped out of college after one year. Rich was tall, disheveled, and good looking. Everyone thought he was just a fling for Lily, but he ended up being the love of her life. They got married after only six months of dating. He also helped her get a job with a theater company that his brother founded, which somehow became successful despite everyone in her family saying it would fail.
Instead, she turned out to be the failure. She’d lost her job. She’d lost her fiancé. She was sleeping in the guest room of her best friend’s townhouse, not knowing what to do with herself. Cynthia had built a life that most would’ve envied. Now, she was the one consumed with envy.
“Don’t think about it,” Cynthia groaned to herself as she buried her face in her pillow. “Just go to sleep. Don’t think about your miserable life…or how happy your best friend is.”
Saying it out loud only made it worse. She could hear the envy in her own voice. She hated how it sounded. She hated herself even more for feeling that way.
Feeling restless and tense, Cynthia stopped trying to shut it out. She just stared up at the ceiling, contemplating what to do with herself.
It was official. Cynthia was at rock bottom. Her only support was an old friend who’d achieved more by doing everything differently. She had to find a job, mend her broken heart, and stop feeling so sorry for herself. It seemed so daunting. She didn’t know where to begin.
As her mind raced in the late hour, a strange noise echoed from down the hall. It was low, but powerful, like music with a heavy base. It was so heavy that it shook the walls of the guest room.
“The hell?” Cynthia wondered.
Restless, curious, and more than a little frustrated, she got out of bed and made her way into the hallway. As soon as she opened the door, the sound got more intense. She recognized it as music, but not the kind most people played at this hour. She also traced the source to Lily and Rich’s master bedroom at the end of the hall. They either forgot that they had someone in their guest room or just had weird tastes in music.
“This just keeps getting worse and worse,” Cynthia groaned.
Her frustration was at a tipping point. She wasn’t even sure she had the right to tell her friend to turn down her music. This was her house. She had let her stay in her time of need. Even so, Cynthia could only take so much.
She approached the door, which was only slightly ajar. There was also some light coming from the bottom. She and Rich were clearly awake. Cynthia was ready to barge in and demand they turn the music down.
Then, she got a brief glimpse into the room through the small crack. What she saw stopped her on the spot.
“Whoa,” she gasped, covering her mouth to hide her reaction.
Suddenly, that weird music gained a whole new context. Lily and Rich weren’t just listening to it for the base-heavy beats. They had incorporated it into something much more elaborate act.
That act involved Lily lying naked on her back, her legs spread wide in a perfect V-shape, while her husband gave her oral sex. Their old gymnastics teacher would’ve been both proud and aghast because she was also handcuffed to the rail of her bed while wearing a blindfold. She didn’t look the least bit uncomfortable, though. If her moans were any indication, she was really enjoying herself.
“Oohhh yeah! That’s it, Richy! Eat that pussy out!” Lily cooed.
“Mmm…so delicious,” Rich said, his voice muffled by her inner thighs.
Cynthia’s eyes widened, keeping her mouth covered to contain another gasp. Growing up with Lily, she’d known her to be many things. Kinky wasn’t one of them. She was the kind of girl who scolded someone for cursing in traffic. The idea of her being so vulgar, even during sex, was quite jarring. It was also a little exciting.
She found herself watching closer as Rich heeded her profane proclamations. The same man who was so soft-spoken at their wedding was indulging in his wife’s genitalia. He licked and fingered her folds with the utmost focus. Even from afar, she could see him flicking his tongue in and out of her slit, paying close attention to her clitoris.
The man knew what he was doing. Lily’s continuous squeals of delight were proof of that. It wasn’t fair. She was tied up and blindfolded, yet still getting more oral pleasure than her ex ever gave her. Cynthia could count all the times Paul went down on her on one hand and he never showed he knew the first thing about vaginas.
She should’ve been jealous. It was more proof that Lily had made the right choice. It wasn’t enough that she picked a better guy. She picked a guy who knew how to eat a woman out. Cynthia wanted to bitter. Instead, she found herself turned on by the sight.
“She’s enjoying it. He’s enjoying,” Cynthia said under her breath, “and I’m just here…watching.”
She couldn’t turn away. The more she saw, the more aroused she got. She felt a wet heat forming between her thighs. It didn’t help that she only had on a pair of white panties and a dirty T-shirt. She began rubbing her thighs together, which caused the heat to spread.
Instincts combined with years of sexual frustration. While watching Rich eat out the pussy of her oldest friend, she slipped her hand into her panties and started fingering herself.
“Watching…and longing,” Cynthia said in a daze.
Her heart pounded in her chest as the heat from her arousal spread. She still remained silent, peering through the crack in the door as best she could. Near as she could tell, they didn’t notice that she was watching. Rich just kept going at it, gorging on his wife’s pussy until her moans became too desperate.
“Mmm…you wet enough, my love?” Rich asked in his charmingly polite tone.
“Fuck yes! You hard enough?” Lily replied.
“My beautiful wife is naked, blindfolded, and tied up,” he said. “What do you think?”
“I think I’m up for some good, quickly fucking from my husband!”
“Then that’s what you’ll get.”
With the same intensity he’d demonstrated with giving oral sex, Rich rose up and positioned himself in the center of the bed. In doing so, Cynthia got a perfect view of his erect cock and toned buttocks. All those jokes Lily used to make about Rich’s manly endowments gained greater meaning. It was more than enough to make Cynthia’s face blush. She also fingered herself with greater intensity.
She clung harder to the wall, watching intently as Rich propped himself on his knees and grabbed hold of her thighs. Before he entered her, though, he removed Lily’s blindfold. It was as though he wanted her to see when he entered her. Cynthia could see the glowing look on her face. She watched her react the second Rich entered her with a firm thrust of the hips.
“Ooh Richy!” Lily cried out.
“Yeah!” he grunted. “So hot…so tight.”
Cynthia couldn’t help but marvel at the sex that unfolded before her. It even exceeded her usual envy. Lily was already awash in ecstasy, moaning and gasping as her husband made love to her. He wasn’t too gentle or too rough. He was just thorough, working his hips in a steady humping motion, pumping that nice male endowment of his inside Lily’s pussy.
The bed rocked.
Their naked bodies rocked.
The booming music rocked with them, as if to maintain the rhythm of their sex.
It was so hot, passionate, and intimate. The way they looked at one another, with beaming smiles to go along with their blissful moans, revealed the breadth of their love. There was a connection, one that went beyond the wedding vows and the sex. There was also an understanding. They knew each other intimately and not just in terms of basic human anatomy. They understood what they wanted, how to give it, and how to enjoy it.
It couldn’t have been more different from the sex she’d experienced with Paul. With him, it had been so rigid. She’d just lay on her back or bend over while Paul did most of the work. It wasn’t necessarily painful or uncomfortable, but it was rarely enjoyable. She couldn’t remember making the same noises as Lily.
“Yes! Oh yes! Ooh Richy! Ooh I fucking love it!” Lily exclaimed in a passionate mantra.
Cynthia, fixated on both her expression and the heated movements of naked bodies, let out light gasps of her own. She stopped covering her mouth, trusting the music to mask her reaction. She needed her other hand to reach up her shirt and fondle her breast. It had been a while since she’d pleasured herself, but she hadn’t forgotten how. She just never had such a stimulating spectacle.
“Lily…you’re so lucky,” Cynthia said under her breath. “That…or I’m really horny.”
As Rich and Lily made love, her legs grew too weak to support her. She steadily sank to the floor, keeping one hand between her legs and the other on her breast. She even pushed her panties down to her knees, giving her more room to work. She pumped two fingers into her folds, using her thumb to stimulate her clit. Warm shots of pleasure followed, but they were nothing compared to what Lily experienced.
She could tell her friend was close to climaxing. Lily once joked that she couldn’t fake an orgasm to save her life. She once tried at a bachelorette party to win a bet with her sister. She failed miserably. With Rich, she had no reason to fake it.
“I’m close, Richy!” Lily exclaimed. “I’m gonna come! I’m gonna come! Oohhh Richy!”
With the music still blaring, Lily arched her body, threw her head back, and let out a moan that left no room for ambiguity. That was a real orgasm. The look of glee on her face said it all. Rich even slowed the pace of their sex to admire it, kissing down her neck and whispering something into her ear. Cynthia couldn’t hear what he said. It must have been something because it made her squeal with even more delight.
“Is it supposed to be that good?” Cynthia wondered aloud.
She fingered and fondled herself more vigorously. Now sitting on the floor, still able to see the spectacle through the crack in the door, she intensified her efforts. In the spirit of fairness, she had to keep up with her friend.
She still felt behind the curve. Even as Lily writhed in orgasmic content, she and Rich shared a loving kiss. It further demonstrated the disparity between the lovemaking they enjoyed and the kind she had with her ex. At this point, however, the answers became painfully obvious.
“It should’ve been better. I…should’ve been smarter,” she said to herself.
In retrospect, it seemed obvious. Paul never treated sex with the same care or passion as Rich and Lily. She’d never been very playful with it, either. She thought she knew how sex was supposed to play out. She saw the kinks and quirks that Lily often described as a sign that something was wrong. Based on what she’d seen, there was no denying who was at fault now.
It was an upsetting realization, but that just got Cynthia more motivated to share in the pleasure. She kicked off her panties, pumped her fingers harder, and kept watching with more scrutiny as Lily and Rich’s lovemaking escalated. The music was still playing and the air was still hot. There was no way they were done.
“God, I love you,” Rich said to his wife.
“I love you too,” Lily said.
“If I uncuff you now, do you promise to ride my cock until I get mine?”
“Of course!” she said playfully. “What kind of loving wife would I be if I didn’t?”
Lily sounded so cheery and playful. She reminded Cynthia of the bubbly persona that had so defined her when they were kids. It was almost too fitting that it had impacted her sex life.
Being a woman of her word, Lily wasted no time in keeping her promise. As soon as Rich unlocked her handcuffs, she shot up from the bed and effectively tackled her husband in a naked heap. She heard them giggling and laughing as they made out in the center of the bed, the rhythm of the music intensifying with each passing second.
Eventually, they found their way into another position. Rich ended up on his back and Lily straddled his hips, facing away to give Cynthia a full-frontal of her friend’s naked body. She kept watching and masturbating as Lily aligned her pelvis with her husband’s rigid cock. Once ready, she lowered self onto him, their intimate flesh once again entwined. From there, she began riding his cock reverse cowgirl style.
It must have been one of Rich’s favorite positions because he became much more vocal. He also showed his appreciation for Lily’s shapely butt, grasping it and even smacking it a few times to encourage her.
“Yeah! Ohhh yeah!” Rich exclaimed. “Ride my dick! Ride it hard!”
“Yeah! You love it, don’t you? You love how I ride you!” Lily said.
Just as before, they moved their bodies to the fast-paced rhythm of the music. Lily proved just as focused as her husband, working her hips and rocking the bed to the movements of their sex. Cynthia might have had the best possible view, even through such a narrow slit.
Lily went at it with the same theatrics that made her so charismatic. She practically danced atop her lover, grooving and jiving to the music, her expression awash with joy and passion. She even played with her bouncing breasts, treating the sex like a one-woman performance. It was an amazing sight.
In that fateful moment, whatever envy Cynthia had turned to admiration. The frustration that originally got her out of bed was a distant memory. Instead, she found herself smiling for the first time since she’d arrived.
“Lily…my friend,” Cynthia said.
That realization proved both cathartic and effective. As a new host of feelings sank in, Cynthia felt the proverbial barriers crumble. The intensity and pace of her masturbation settled, her fondling now mirroring the rhythm of Lily and Rich. Whether by fate or fluke, it led her to the brink of orgasm. For the first time in what felt like a lifetime, she was going to enjoy this pleasure on her own terms.
“Mmm…you close yet, love?” Lily teased while riding her lover’s cock.
“Yeah…I’m close!” Rich gasped, sounding out of breath.
“Then hold on! Here…comes…the finale!” she told him.
For the final push, Lily rode him harder. She rode him harder than the rhythm of the music. It really sent Rich over the edge. His panting intensified and he grabbed hold of his wife’s butt in anticipation. When the feeling arrived, he let a deep, masculine grunt before their naked bodies contorted into one last spectacle. Cynthia even see them both shudder under the weight of the pleasure.
At almost the same exact moment, Cynthia climaxed as well. For once, she could share in the fun.
“Oohhh Lily!” Rich cried out.
“Mmm…yes!” Cynthia gasped.
She was louder than she’d expected. It was no use. The feeling was too intense and too overdue.
When it hit, all semblance of discretion went out the window. Cynthia felt her vaginal muscles contract around her fingers in accord with her release. She squeezed her breast, her toes curling and her legs bending back as a wave of pleasure shot up from her core. It was the kind of orgasm she hadn’t had in a long time. She’d almost forgotten how great it felt. It was almost sad that she’d denied herself for so long. It further affirmed how wrong things went between her and Paul.
Had she simply timed her moan in accord with the music, Cynthia might have tone unnoticed. However, under the onslaught of ecstasy, she’d thrown her head back and banked it against the door, causing it to open. Before she could catch herself, it was too late. What happened next would either be the most mortifying moment of her life or the most hilarious.
“Hey there, Cyn!” Lily said, still straddling her lover’s cock. “Enjoy the show?”
“Uhh…” she stammered, her face bright red as she tried to hide behind the door.
Had she not been in the midst of an orgasm, she would’ve gotten up and ran. There was no way her legs could support her. All she could do was look up from the floor, naked from the waist down with her right hand still buried between her thighs, and smile awkwardly at her friend.
“I hope she enjoyed it as much as us,” said Rich. “We tried to bring our A-game.”
“If her lack of panties are any indication, I’d say we did our part,” Lily laughed.
Cynthia was still at a loss. She opened her mouth, but no words came out. However, she was still smiling. Embarrassment aside, she didn’t feel nearly as awkward as she’d anticipated.
Neither Lily nor Rich seemed too upset. If anything, they looked amused. Already bathing in afterglow, Rich rose up from the bed and embraced his wife from behind. Lily rose off him as well, settling comfortably in his naked embrace. They didn’t attempt to cover their naked bodies. They just looked like a happy, content couple greeting a distressed friend.
“I…guess I have some explaining to do,” Cynthia said, trying not to look more foolish than she already did.
“What’s there to explain?” Lily shrugged. “You heard me and Richy having sex. You got curious, you liked what you saw, and you got horny. It’s as simple as that.”
“Granted, you never struck me as much of a voyeur,” said Rich, “but we sure don’t mind.”
“I’m not like that,” Cynthia said. “I…I don’t know what this is. I just…”
She tried to put it into words, but that proved impossible. After realizing how wrong she’d been, how could she even know what felt right? She tried to look away, but she already felt Lily’s sympathetic gaze.
She and Rich didn’t let her just linger on the floor like some pervert that fell out of a tree. They got up off the bed, knelt down next to her, and embraced her as only two wonderful friends could.
“It’s okay. You don’t need to say it,” Lily said. “It’s like I said when I invited you to stay with us. We’re here for you.”
“And we meant it,” Rich added. “We just didn’t think you’d need us to be here like this.”
“Sorry,” said Cynthia with a sheepish smile. “I guess I still have a lot of issues to work through.”
“That’s okay. Rich and I will help you every step of the way,” Lily said with a warm smile, “and if you want part of that to involve our sex life, then all you have to do is ask.”
They all shared a good laugh. Cynthia even had to hide a tear of joy as she embraced her friend and husband in a moment as satisfying as any sex act.
She had made her share of mistakes. She came to her best friend, broken and envious. After her breakup with Paul, she couldn’t have felt lower. Now, she had a better perspective. She had a lot to learn about love, sex, and managing herself. It was nice to know she had the support of her friend and her husband.
Plus, the idea of reimagining her sex life with such a playful couple had plenty of appeal.