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A Mysterious Date

"A separated mother's new hobby leads her to a life-changing night."

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Christine was a thirty-eight-year-old mother going through a rough patch in her life. Over the past few months, she had separated from her husband and seen her son leave out of state for college. She was alone and didn’t know what was next for her. One side of her missed the life she used to have and the other side was excited at the possibilities of a fresh start.

Her life as a married mother had distanced her from all the social circles, but she wasn’t one to go out much anyways. Her work life was minimal since she owned a few properties and a small business that practically handled themselves. The only current hobby she had was exercising at home, dumbbell workouts and running on the treadmill to be specific. With so much time and freedom, she could undertake any venture she fancied.

The first thing she tried was opening a blog, but she quickly scrapped it, as it had no clear direction or purpose. She joined online forums and new social media sites only to find that she didn’t fit in and was better off deleting the accounts. Everything seemed dull until she decided to rekindle her love for writing.

Writing was something that challenged her emotionally, technically, and creatively. She just had to decide what to write about and where to publish it.

I could write a book about psychology or get into freelancing articles, she thought.

Those thoughts stayed with her for a couple of weeks, but nothing materialized until she was up late one night browsing the internet on her desktop and stumbled upon an erotica site full of sex stories. She looked through the site and was surprised by some of the listed categories.

Cheating, Taboo and even a Sci-Fi category, she read.

She settled for the MILF category and scrolled through all the recent stories posted. She selected one she could relate to, a story about a recently separated mother.

Halfway through the story, her hand found its way between her legs to rub herself through the thin fabric of her panties.

This is pretty fucking hot, she thought. I could really publish stories on here.

She eagerly read through the rest of the story, picking up the pace of her rubbing with every paragraph. By the time she created an account to give the story a five-star rating, her panties were soaked in her climax and clinging to her swollen lips.

She used her middle name as her username and only filled out her profile with basic information, careful to remain as anonymous as possible.

Should I set a stock profile picture or take one of myself? she asked herself.

If she had been thinking with a cool head, she wouldn’t even have considered uploading a picture but the hotness between her thighs pushed her to be more daring. She went to the bathroom, removed her nightie but left her cheeky panties on. She opened the camera app on her phone and set a five second timer so that she had time to pose. She fixed the lace waistband of her panties then placed her hands on the wall to lightly stick out her booty for the camera.

Perfect, she thought, pleased by how her panties accentuated her round bottom.

She hurried back to her room in just her panties and transferred the picture from her phone to the desktop. She uploaded the picture to her private gallery and set it as her profile avatar.

For the rest of the night, she sat nearly naked on her desk typing her first story, which had an emphasis on BDSM. The process of constructing the story was arousing to her mentally and physically. The more twists and turns she came up with for the story, the more vigorously she masturbated and the harder she orgasmed.

By the time she submitted the story for verification, the sun was shining through her blinds and her body was deliciously exhausted.

God, that was so fun, she thought as she headed to bed.

When she woke up, the first thing she did was check the website for the status of her story. To her surprise, it was already verified and posted for the users to read.

Looks like people are liking the story, she thought, reading through the comments and seeing the overall rating of the story.

She then checked her inbox and saw she had received a lot of messages from people welcoming her to the site and raving about her story.

One of the messages read, I don’t know what I like more, your story or your booty.

She gained a confidence boost by how many users complimented her physique and promptly replied with appreciation to all those who reached out via private message.

One message in particular caught her attention, it was from a man introducing himself in a detailed yet mysterious way. She clicked on his profile and didn’t gain any additional information about him other than the fact he was into BDSM like herself.

Leaving the text cursor blinking on her screen, she thought about her response before typing, you are quite intriguing.

A couple of minutes passed, and she received a reply from this mysterious user that read, I’ll be in Chicago next Friday if you’d like to see how intriguing I can be.

Playing along, she replied, what makes you think that I’d meet with you?

When he didn’t reply in a few minutes, she took the time to hop in the shower. Under the warm water, she couldn’t help but fantasize about the possibilities of meeting one of her newly found fans.

He’d be a total stranger but that would make it even hotter, she thought, removing the showerhead and bringing it between her legs to massage her clitoris.

After her warm, yet refreshing shower, she returned to her room with just a towel wrapped around her body.

She checked her inbox and saw that he had replied, something tells me you’d be down for an adventurous night of BDSM. Check back here tomorrow.

She decided not to reply and instead go downstairs to the living room to cool off from the rush that had been joining a sex stories site. She occupied herself for the rest of the day but in the back of her mind she couldn’t stop thinking about the mysterious user.

The following day, she logged in to the website and went straight to her inbox to check her messages. She scrolled through them, looking for that one particular message that would ignite a fire between her thighs.

Sure enough, she found the intriguing follow-up with a link to a map and a message that read, Be at this hotel next Friday at 9pm. Room #387.

Feeling daring, she replied, I’ll be there.

For the next few days, she went back and forth in her head about going on the date. She had never done something like this, which scared and excited her at the same time.

Wanting to keep her options open, she kept a perfect diet and worked out extra hard to prepare for the potential hot date. She spent a considerable amount of time choosing her outfit before finally deciding on a floral blouse, black leggings and a red bra and panty set that she had never worn for her husband.

She didn’t give herself a straight answer until the morning of the date when she woke up with her panties drenched in her juices.

You’re doing this, Christine. Don’t pass up the opportunity to fulfill your biggest fantasy, she mentalized herself.

She spent the morning giving herself a full spa treatment, including getting her nails and hair done. She was so excited that she had no appetite and couldn’t focus on whatever was happening on her TV. All she could do was repeatedly check the time on her phone and fill the house with her favorite music.

With an hour left to go, she went up to her room to change into her selected outfit. The red push-up bra cupped her medium sized breasts while the matching lace-trim cheeky panty snugly wedged between her cheeks and hugged her lady bits. The floral blouse was cool and comfortable but not so thin that her bra was visible through it. The leggings were light and fit like a second skin, accentuating her thick thighs and shapely derriere.

When she arrived at the hotel, she parked discreetly at the back and took a deep breath before getting out of her vehicle. She walked through the parking lot and into the lobby, looking around hoping that she didn’t recognize anyone. She opted for the stairs to avoid any possible interaction with people on the elevator.

Third floor, room number 387, she told herself, not realizing a hotel staff member was behind her.

The man climbed the stairs behind her, entranced by the sway of her hips and the sight of her leggings digging into her cheeks.

She exited the staircase on the third floor, with the man getting one final glance of her booty as he continued his way up. She looked at the room numbers on either side of her as she approached the designated room for the night.

Here it is, 387, she thought, nervously knocking before reaching for the door handle.

To her surprise, the door was unlocked, so she entered the room cautiously. She found it spotless with no sign anyone had been there, except for a bottle of wine on the desk and a small black box on the front of the bed. She walked towards the bed and picked up the box, noticing her username from the website was detailed on top of the box.

She opened it to find a black luxury set of BDSM accessories – blindfold, mouth ball gag, and a pair of handcuffs – and a note that read, put them on if you’re feeling adventurous.

I’m already here so might as well make the most of it, she reassured herself.

She placed her purse on the nightstand and stripped down to her matching red underwear. She began by securing the pair of handcuffs to one of the vertical wooden bars of the headboard. Next, she put on the ball gag, which was breathable and comfortable to wear. Then she put on the soft blindfold over her eyes and finished by moving her hands over her head to lock the handcuffs on her wrists.

This is so fucking hot, she thought, rubbing her thighs together as she waited for him to arrive.

Checking the time on his watch, he calculated he had given her plenty of time to make the decision to stay or go. He entered the room and found her laying on the bed in full submission.

She lightly squirmed in anticipation of his touch, hearing his footsteps get louder as he approached the bed. He wanted nothing more than to ravage her in that instant, but he knew an experienced Dom had to show patience, so he slowly removed one item at a time until he was completely naked.

By the time she felt his weight on the bed, her pussy was more worked up than it had ever been. The first contact was his lips planting a kiss on her neck and working their way down to her breasts and abdomen. He then dug his fingers under the waistband of her panties and pulled them down, watching closely as the gusset peeled off her wetness.

“Mmnngg,” she moaned through the gag.

He placed his hands on the back of her thighs, holding her legs open with her knees bent over his shoulders. His flat tongue pressed over her opening and licked all the way up her creamy slit until it reached her engorged clitoris.

She squirmed and rattled the handcuffs at the feeling of his wet and warm tongue lapping over her pleasure button. She didn’t know what to expect, if he was just going to tease her or give her a cunnilingus session. She was used to her husband making those sessions extremely rare, short, and disappointing.

However, this mysterious date had no plan to stop his assault on her clitoris. He kept working his mouth on her by enthusiastically licking, nibbling, and kissing her nub until her chest was heaving.

The accessories restrained her from moving, touching, talking, and seeing. Her submissive state enhanced her sensitivity and surrendered her body to his will. She was experiencing the beauty of BDSM for the first time.

“Ohnngg,” she cried, feeling herself close to the edge.

Suddenly, he removed his mouth from her wetness to prevent her from orgasming and the next thing she felt was his bulbous head running the length of her slit. He continued parting her legs as he tapped his head on her clitoris.

“Mmnngg,” she whimpered in anticipation.

He aimed his oozing head at her entrance and pressed it lightly to spread her swollen lips. He watched closely as bit by bit of his length penetrated her, stretching her pussy as it accommodated to his thickness. He adjusted himself closer to her, placing his hands on the back of her thighs to push her legs back, allowing him to bottom out inside of her.

“Ggnnn,” she responded, feeling him reach previously unexplored depths.

He let them both savor the moment before pulling out until only his head remained inside of her. He then pushed himself back into her, crashing his body against her thighs, and continuing with deep strokes. Her pussy squelched with every thrust as juices ran down to her puckering rear entrance and onto the bed to form a noticeable wet spot.

He relentlessly pounded her flesh like a madman as he watched her breasts bounce in her push-up bra. His hands hungrily moved up to pull down her bra, revealing her erect nipples. He pinched her pink nubs, rolling them between his fingers then squeezing her breasts. Her pussy tightened in response to his hands, which only encouraged him to fuck her vigorously. She had never been ravaged like this by a man with such lust for her body.

This stranger is giving me the fuck of my life, she thought, feeling her vaginal structure preparing to release a shattering orgasm.

He felt her walls contract and stopped the pummeling, once again controlling her orgasm by pulling himself out and tapping his bulb on her clitoris. She bit down on the gag, enjoying the delicious denial near the edge of her orgasm.

He helped her turn around, positioning her in the doggy style position with her round ass mere inches from him. He grabbed handfuls of her soft cheeks and parted them, leaning forward to bury his face between them. His tongue licked circles around her rear entrance before swirling directly on it.

I love how kinky he is, she thought as she experienced the sensation of anilingus for the first time.

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He kissed her puckering hole then straightened up to tease her by tapping his cock on her ass cheeks. He took a moment to admire the sight of her curves, especially her waist-to-hip ratio, as she teased him back by wiggling her ass. He spanked her hard, leaving his imprint on her cheek and letting her know that he would not be teased by his fuckdoll.

“Ohhmm,” she moaned, enjoying the sting of his hand.

He confidently pushed himself into her, knowing that this position allowed for comfortable deep penetration. His hands firmly held on to her ass cheeks as he buried his entire length into her, reintroducing his oozing tip to her cervix. He spanked her again and slowly pulled out three-fourths of his length, noticing his shaft was painted in her white pussy cream. He then began moving his hips in a rhythm for deep and long strokes.

While her cervix started going numb, her phone rang and she knew it was her husband by the custom ringtone. She was sure he was drunk on this Friday night and ready to beg her once again to return with him.

Fuck off, I’m not hearing it tonight, she thought, with the loud clapping of her cheeks drowning out her husband’s call.

Almost as if punishing her for receiving a call, he forcefully spanked her cheeks bright red. Every time his hand struck the softness of her ass, her pussy tightened a bit more in preparation of her climax. Knowing that she was close and that he couldn’t keep up such pace for much longer, he reached to grab a handful of her long dark brown hair for the grand finale. He pulled on it, raising her head and arching her back at his mercy while her rosy cheeks rippled at the contact with his thighs.

He clenched his teeth, mustering the will to delay his orgasm until she was satisfied. With the thumb on his free hand, he ran circles around her wet sphincter before pressing it inside of her. This intrusion to her unexplored cavity was enough to send her over the edge.

“Uhhnngg” she cried, feeling her rectum and pussy convulse.

Her pussy formed a vice grip around his cock and erupted sex juices uncontrollably. If it wasn’t for him pulling on her hair, she would’ve collapsed from the pleasure of her first squirting orgasm. The feeling of her juices soaking his cock overwhelmed him and he began spurting shot after shot of his warm load into her contracting walls.

After enjoying the post-climax sensation for a few moments, he removed his thumb from inside of her and spanked her one last time before letting go of her hair. She collapsed on the bed, with half her body resting on huge wet spot they had left behind. In her nearly comatose state, she could barely sense his weight near her as he removed the handcuffs from the headboard and released one of her wrists.

By the time she regained her strength and removed the accessories, he was gone with seemingly no trace left behind, except for the copious amount of fertile seed leaking out of her gaped pussy.

Looking down at her clothes on the floor, she smiled, did he really take my panties?

She turned to the nightstand to order dinner and spotted a small note that he placed there. She grabbed the note, expecting to see something about a second date, but she turned ghost white when...

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Written by Issabela
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