tagAnalAlyson's First Anal Experience

Alyson's First Anal Experience

bydarktigerroar©

"Well isn't that lovely! I'm never getting married!"

Alyson stepped on the tile at the entrance of her home and kicked off her cherry red heels.

She had returned from her third date in a row that ended in disaster. Having turned thirty the week before, she heard the clock ticking and the walls of time closing on her. Everyone in her circle was hitched or engaged and wore sparkling rocks on their fingers. Some had younglings running around. None of them were Alyson and it was as obvious as the purse she launched across the room in rage.

Alyson's latest date was nice enough. He gave her a rose and pulled her chair out for her. He ordered wine and they spoke about each other's lives and what they wanted for the future. A second date may have been in their futures if he walked her to her car and gave her soft, sweet kiss but no. He dropped to a knee and popped the question. The diamond he offered sparkled beautifully enough but she barely knew his name. Crash and fucking burn.

He's more desperate than I am!

Life was doing standup. She did ask for a husband. Maybe she should have been more specific.

Alyson had the house. Had her dream profession as a personal trainer. There was one piece missing from the puzzle. It seemed more likely she'd be struck by lightning than fill the void. Not that she was ready to play the odds. None of her clothes were insulated.

Alyson marched over her brown plush carpet. It massaged her feet on her way to the tile on the kitchen floor. The refrigerator was her target. She didn't stop until she flung it open, snatched an amber bottle, and turned it up. She was swirling her tongue upon her lips to slurp any beer that dared escape her mouth. The cool beverage slithering down her system brought with it a relaxation and the beginnings of a buzz that began to absorb the pain of the latest dumpster fire called a date.

Alyson leaned against the island centered in the kitchen and set the bottle on the marble top. She used the back of her hand as a napkin to wipe the remains of the alcoholic liquid from her lips.

"Why can't I attract the right guy? I must be cursed. Instead of a guy maybe I need someone to lift this hex off me!"

She griped and took another swig. Before lowering the bottle, she realized she needed a double.

After sucking the last drop from the bottle, she swiped another from the refrigerator and dumped half down her throat in a single gulp. A buzz was hitting hard and her night out was fading into a memory.

Alyson's laptop on the dining room table was captured in her random scan of the room. A look at Facebook might redirect her thoughts in another direction.

She lifted the lid while lowering into the chair. She almost couldn't wait to see what juicy drama her friends were getting into.

After logging into her account, her friend, Shelli, and her husband were going out for movie night.

Oh, and Keisha and her fiancé were staying in watching Netflix with a bowl of butter popcorn.

Emilia and Cameron were taking dance lessons together.

Okay, perhaps checking her Facebook was a small error in judgment.

"Oh, my God! Life, do you have to keep reminding me that I'm alone? Ugh!"

Alyson tossed her hands into the air and slammed her back against the wood of her chair. A crippling discomfort contracted her arms, legs, tummy, and heart. Her eyes moistened and a tear trickled over her cheeks.

Alyson propped her elbow on the table and rested her chin in her hand. She typed "se" into the browser's search bar. "Settling for the wrong guy" was what she intended to find. She was looking for articles, message boards, or blogs where women expressed their feelings on whether they'd settled for the wrong guy and how their lives turned out. Settling was believed to be Alyson's path to happiness. If there was another way, she hadn't conceived it.

When she input "se", sex was one of the autocomplete options. Dirtiness clogged the area between her ears and the distraction she sought revealed itself. She hadn't laid with a man (or woman) in a few months and a woman had needs. More feelings of hopelessness crept forth when she found herself resorting to porn.

Alyson searched for romance porn and nibbled on her pinkie nail like she was the one being seduced in the first vid she opened. Her likeness didn't quite match the long, brunette tresses of the tall adult film star nor did her hourglass frame or perfectly round breasts and ass resemble hers but she could play make-believe.

The hunk, mysteriously bare from the waist up after coming home from work, displayed his mountain of pecs, carved arms, and six pack as he greeted his beloved with a kiss.

Alyson wasn't certain if she was more aroused or disgusted by the time they were rustling in the sheets like wild teenagers.

Whatever the mix of emotions that were flooding her body, Alyson scooted away from the table. She lifted her ass from the chair, hiked her red dress to her waist, and slipped off her black panties.

Her fingers sneaked between her legs. She was giving off a scent of arousal that would have been intoxicating if anyone besides herself was in nose length.

She slowly spun a pair of digits over her swollen clit and a jolt shot through her. Alyson shook in delight and her heart sped a notch. She leaned against the glass and gave herself some swifter strokes. Her legs tightened and she went faster still to the rhythm of the man onscreen driving his cock into the open legs of his female counterpart.

Alyson parted her own legs and started teasing her pussy's lips with her digits but she could wait no longer and plunged them inside. She twisted them around, moved them in and out as hard as she could before going fast until her legs were quivering.

She sealed her eyes to absorb the sensations. She peeked at the screen and the woman was on all fours. She was pulling her cheeks apart and he was angling his swelled head at her asshole. Alyson pinned her attention to the anal intrusion. Her dirty chute swallowed half of his manhood and a spark flared within Alyson and a pool of wetness drenched her pussy.

The man squeezed her cheeks and began steady rocking motions inside her forbidden hole before pounding screams out of her.

Alyson once dreamt of a man taking her like that if he was skillful enough to do it with more pleasure than pain. At least with a healthy mix. The thought fled from her when she realized that might require actually meeting a decent man.

Alyson's phone blared from her purse. She would have preferred the interruption came after hitting an orgasm but she sighed and ran to the couch to fish out her cell.

"Emilia Calling."

That summoned a conflict of joy and envy. It was her best friend who posted she was out with her boyfriend at a dance studio. Alyson wondered why she wasn't with a guy at a dance studio.

Alyson and Emilia were linked together since freshman year at college a dozen years prior. There was nothing one didn't know about the other and they became so close, they tried to be more "serious" at one point. Their romantic relationship survived through junior year until Emilia got an eye for the opposite sex again and they split from their relationship but not their friendship.

"Hey Emilia..." Alyson answered like the world was at its end.

"Aly? Where's Aly? That doesn't sound like you. Are you okay?" Emilia asked. Nothing concerned her more than Alyson's wellbeing, almost to the point of being smothering, but Alyson cherished her like a priceless gem.

"I'm fine. In fact, I'm having a party!" Alyson said with faux excitement.

A trickle of matching joy found its way into Emilia's voice. "Really? So things went well with you beaux?"

"It's not that kind of party. It was more of the...pity kind. Let's just say my date already proposed to me. I learned his name three days ago. I thought I was desperate but he had nothing on me. So, I'm drowning my sorrows at the bottom of a few bottles."

"Oh, Aly!" Emilia said mimicking her friend's true feelings. "I can't let you do that. I'm coming over!"

"No, no, really, I'm okay. Really!" Alyson was trying to convince herself more than Emilia but both efforts ended in futility.

"I said I'm on my way. You don't need to be alone right now. When my dates went sour, you were there for me in case you don't remember."

Alyson nodded to herself. "I know! I know!"

"Okay, I'll be over as soon as I get ready. Talk to you soon. Bye."

"Bye..." Alyson said. She dropped her phone on the coffee table and walked into her bedroom down the hall in front of the couch.

She flipped on the light and lifted the dress overhead. She slang it to the bed and pulled a pink cotton shirt from the drawer to don in its place. Before tossing it on, she checked herself out. Her breasts were a little larger than average and she gave them a feel and tug of her erect nipples. Her legs had a peach tone and were well-cut as a necessity in her field.

Alyson flipped the auburn hair that rested upon her shoulders and shook her head trying to figure why she was still in the midst of her single days. She concluded her looks weren't the reason for her missing other half. She was carded when she bought the beer she guzzled.

She threw on her shirt and beneath the shirt drawer came her plum pajama bottoms.

She stepped into them and covered her pussy and hairs, which were covered in her juices. The mood passed with Emilia on her way so she plopped on the sofa and stretched out. She tucked a pillow behind her head and snoozed until her friend made her arrival.

It wasn't long after she slipped into the dream world that a "dingdong" brought her from her slumber.

She laid there a few moments to shake the sleep out. She was relaxed and buzzed but in peace and refreshed. The doorbell rang again and she hopped to answer it.

Alyson flung the door open and there was Emilia. Alyson could look her in the eyes without shifting her head up or down. Emilia also shared her age but not Alyson's laidback demeanor. Emilia managed at a Fortune 500 investment firm. Alyson managed to help people train and eat their vegetables. Neither were elementary tasks but both fit the women's personas.

Emilia's blonde hair was in a ponytail with hair dangling that framed her pink facial cheeks and matching plump lips. She was in a black dress and matching heels. Her breasts were smaller than her friend's but she was gifted by an ass that pushed her dress outward and made Alyson wish they could trade backsides.

Sapphires dangled from her ears, gold surrounded her neck, and bling sparkled from most of her fingers. Emilia could have bought her house with everything she wearing.

"Hey, Aly," Emilia said. She grabbed Alyson and jerked her into an embrace. The warmth of another body to soothe Alyson was nothing short of what she needed.

Alyson slid her arms around her and squeezed tighter.

"Hi. I'm glad you could come," Alyson spoke into her ear. "I thought you were out dancing?"

Emilia leaned away but kept a hold on Alyson's back. "I was but you needed me so here I am."

Her words overtook her with a fuzzy feeling. "Aww, you didn't have to do that but thanks."

"Sure..." Emilia said while walking into the house.

Alyson closed the door behind them and grabbed a glimpse of her laptop being open. The porn!

Alyson made her way in the computer's direction. She didn't want that to become a topic of conversation. Besides, she didn't find it easy telling her friend she wanted some hot guy's beast in her ass.

Emilia was admiring the potted plants that rested on either side of the doorway before moving to the pink daisies along the window seal. "These are pretty. I need some of these in my house."

With Emilia's rear to her, Alyson slipped next to her laptop and pushed the lid closed. Relief washed through her. "Yes, they're lovely aren't they?"

Emilia flipped towards Alyson. "I know you're hurting. Is there anything I can do?"

Nary a word, Alyson popped open a cabinet, pulled out a pair of teabags, and prepared them on the stove. Tea was more a favorite of Emilia than Alyson but they both enjoyed bonding over it.

After taking a pair of teacups from above the sink, Alyson said, "You being here is plenty for me. Would you like to watch a movie?"

The rings of Emilia's phone spoke first and she looked as though she really didn't want to answer it but her job would follow her to the grave if she allowed it.

Emilia smiled but it seemed to cover her disdain for what she had to do. "I'm sorry, Aly. It's Gary from the firm."

Alyson nodded and continued to prepare the tea. It wasn't like this was unfamiliar. She was an important figure but Emilia was always anxious to make up to her the perceived lack of respect. Alyson understood but Emilia usually insisted. Last time, Emilia paid for pizza and the movie. The time before that, she gave her a gift card to the boutique. It's still at its home on the dresser and would become a gift for Emilia's birthday instead.

Several minutes later, Alyson tilted the teapot to fill the ceramic cups. Emilia was in the midst of yammering with Gary about work stuff Alyson couldn't comprehend.

When Alyson turned to take the cups to the coffee table, Emilia was approaching the dining room table. Alyson curled a brow because they never sat there.

Emilia pointed at the laptop and covered the phone's speaker. "Can I use this?"

Alyson separated her lips to answer but Emilia was already sitting in the chair and raising the lid. Every "can I or may I" question between them was always "yes" but this night, she wished she could have said "no."

Alyson's gut grinded but as long as she closed it completely, it would have locked and she'd have to enter her password to get back in. She watched for Emilia's reaction through the light shining against her face. The moans coming from the laptop and Emilia's jade irises gazing at Alyson told everything that needed to be said.

Alyson's face resembled the hue of the dress she wore that night. She clanked the teacups on the countertop and angled away from her friend.

Now, that had Emilia ending her conversation with promises of a callback to Gary. Alyson waited for the conversation to come her way.

The video would have displayed a black screen had it ended before Emilia laid eyes upon it but no such luck.

"Alyson?"

"Yeah?"

"Why are you standing over there? The tea is ready isn't it?"

"I should, um, bring it over," Alyson said with a curl of her finger around each of the cups' handles.

She turned and resumed her trek to the coffee table. She snared a glance at her laptop's screen. Emilia was going through her work e-mails but she didn't touch the volume nor was she searching for it. The porn stars were still going at it in the background.

"My e-mails weren't coming up on my phone. I had to use your laptop..." Emilia said to the clacks on the keyboard. "I'll be with you in one sec."

Alyson lowered to the couch and reached for a sip but the rattling in her fingers had her rethinking that idea. What was Emilia going to say about what she saw? Watching porn wasn't something either of them ever talked about. They spoke of it as more of a "guy thing" but at least one of their secrets were out.

A few minutes passed before Emilia slid from her seat and joined Alyson on the couch.

Emilia angled towards Alyson and took a sip. Their knees touching sent tiny rumbles through Alyson. It had been a long time since they were a couple but that didn't make Emilia any less attractive or alluring. Though that day may never come again, Alyson's pussy reacted by filling with heat and wetness as it always had in her presence.

"How was your day?" Alyson asked but Emilia spoke a fraction of a moment after her. She was used to getting in the first word, the last, and often most of the ones in between.

"Alyson," Emilia said as she took her friend's hand. Comfort poured from her hand into Alyson. "Those men weren't right for you. If you were with them, think about how much complaining you would be doing. Stop acting desperate and you'll attract a good one. I promise."

It's not that thirty years old was anywhere near the rocking chair but for Alyson, it might as well have been.

Alyson pushed an agreeing grin across her lips. "You always tell me what I need to hear."

"You heard me but did you really listen?"

"Of course. I don't need a lecture. I got it."

Emilia sometimes confused giving friendly advice with giving a college level speech.

Emilia said, "Sorry. I'm working on not bringing my work face home."

"It's fine."

"How long have you been watching anal porn?"

Alyson couldn't say she'd heard anyone ask that before let alone after a pep talk. That came from the blue but only someone who wasn't familiar with Emilia would be thrown off by her bluntness. Alyson's fetish was in the open and she felt a twisting in her stomach.

Alyson said, "Oh, that. I, um, didn't know that video had anal in it. The title said, 'romance.' I don't know what butt sex would have to do with that."

Emilia drank more of her tea with her friend firmly in her sights. "Why are you nervous? It's okay to like anal. It's actually pretty pleasurable if you do it right."

Alyson was extending her hand towards her teacup but déjà vu hit and she paused again. Emilia, the woman that exuded a presence that shook most men's knees and had other women submitting to her, liked to be taken in the ass. Alyson found that difficult to fathom especially since they never discussed things of that nature. Almost as a silent assumption between them it was a dirty, forbidden act. BFFs for years and this night they learned of their anal desires.

Alyson's discovery of Emilia's fetish made it easier to talk about her mutual fascination with ass. "I've been thinking about it for a while but I haven't done anything with my tush."

Emilia traced the length of Alyson's arm and her hairs leapt. All the while, Emilia was staring at her friend with a tilt of the head and a lingering, lustful look. Alyson's thighs tightened and her panties were dampening. She hadn't seen a look like that from Emilia since they dated. Her mind wanted to ask what it meant but she shushed the thoughts and went with what was happening.

Emilia's fingertips traveled from the back of Alyson's hand to her legs near her sweet spot.

Emilia asked, "So, what have you thought about doing?" A chuckle followed from Alyson formed from her nervousness about the taboo subject. Emilia sighed but it was one of frustration and a dash of annoyance. She swatted Alyson on the knee. "Come on, tell me. We always talk about everything. This doesn't have to be different. You never know what might happen if you let it out..."

Alyson's curiosity about those last words pushed her to grant her wish. "I just want to try, I don't know, having a guy take me and my ass." The mere thought of that sent a rush through her legs and pussy. She was pulsing with tingles. "I would have to trust him, though. Lately, I can't get to a second date let alone get to that point..."

Emilia burst off the couch as she was attempting to finish her rant and Alyson was startled along with her heart leaping into her throat. Alyson's eyes widened and her jaw fell.

Emilia asked, "Do you want a preview of the pleasures of anal? After that, you can decide what you want to do from there."

Alyson paused to process the churns in her mind. "Uh, what do you mean?"

Emilia tossed her hands on her hips and firmed her stance. "It's something better experienced than described. Get on your knees on the couch and grab the back of it." Alyson hesitated but if she couldn't trust Emilia, who else would be worthy of it? Emilia eased off her naturally intimidating posture and said, "If you don't like anything I do, you're free to tell me to stop."

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