Fucking Valentine's Day. She hated Valentine's Day. Yeah, yeah, it was the day of romance, to show the one you're with how special they are with chocolate, jewelry and a night of hot sex. For her, like many others, it was a slap in the face, a laugh at the single people out there that weren't good enough to snag someone to spend Valentine's Day with.
Jessie knew that going out to the local bar tonight would only make things worse. She would be surrounded by couples spending the night out for dinner and drinks, boxes of candy, jewelry and flowers seated at their table as they snuggled in and tried to be romantic. She cringed at the thought of having to stare at them while nursing a drink at a bar, alone.
She laughed at herself, knowing she was playing the irony card. Just last year she was one of those people, sitting at a restaurant and sharing a dinner with the love of her life while flowers decorated their table and she wore a diamond bracelet he purchased for her. Only now he was gone, leaving her because she was too frigid, a bitch that wouldn't give it up when he wanted it or how he wanted it. Jessie was shy, introverted and naive and just plain vanilla. He wanted a rough, tie me up and spank me, please put it in my ass and fuck me hard, type of girl. So he dumped her, two months ago, just before Christmas.
She stared at herself in the mirror, trying to smile. She had been thinking of this night for quite a while now. Not having anything in her closet to wear, she had to run to a friend and borrow something from her. Standing straight, her arms down at her sides, the skirt still wasn't reaching her finger tips. She bent her arms and tugged at the hem in hopes of covering her entire ass. She felt the cool breeze from her air conditioner and knew that she would end up flashing the entire bar. Her nipples were hard and pressed against the thin material. She chose not to wear a bra, her large triple d's resting heavily on her body. Thankfully the dress was so tight that it mashed them together and sorta held them up, showing off an ample amount of cleavage.
She had been to the spa earlier and got a fresh waxing. The lady taunted her, unaware that she was riding solo on the wonderful holiday night. The woman wanted to bejewel her twat, add a little rhinestone heart just above her bare lips to add that extra sparkle for her man. Jessie laughed, no way in hell was she putting a heart above her fuck hole! She had another thought though and had to laugh when the woman nearly choked on her coffee as Jessie told her what she wanted.
The night he left, Jessie turned on her computer. It was their computer, shared, but she needed it for work so he left it. She clicked on the search history and gasped as she saw line after line of nothing but porn. There were women getting gang banged and having huge cocks shoved down their throats. Women taking it in the ass or getting spanked over some sort of bench. Their hands getting tied behind them while they were fucked hard and fast. She was not like them, had never been tied up, spanked or gang banged. She had given head but apparently that was boring as well.
She watched video after video, her own pussy betraying her and growing wetter and wetter. By the 12th video, she was rubbing her clit furiously, her legs shaking as she came while watching a girl getting pissed on by a group of guys, their cum dripping all over her face. So this was the kind of slut he wanted, huh? She watched these women get defiled, treated like sluts and yet beg for more. How could this please them? How could they be satisfied with being used? She decided to focus on them, to time her orgasms with theirs and see if it was worth it. By the 15th orgasm, her body a weak and sweaty mess in the desk chair, she knew what she was going to do.
January came and she had finally worked up the nerve to go into the sex shop. Sure it was one clear across town where she wasn't worried about running into anyone but it was still a sex shop. The place was huge and she was in awe as she surveyed shelf after shelf of various sex objects. She had no idea there was this much to add to sex! Jessie kept her head down, avoiding eye contact with anyone as the embarrassment flushed her face and turned her cheeks pink.
She made her way up and down each aisle without being approached. Relaxing a little, she stopped in the anal section, her mouth hanging open at the wide variety of toys one could use to put in their ass. She found a starter kit, three butt plugs that graduated in size and came with a large bottle of lube. She shuddered as she imagined what it would feel like to shove the biggest one into her ass. Probably wouldn't happen but she figured she would try the smaller two and see how things went.
She also grabbed nipple clamps and a large rubber cock that seemed to be about the same size as Joshua's cock. She needed to get fucked even though she was vanilla and didn't do wild and crazy in bed. Her pussy had needs.
Jessie walked to the counter and kept her head down. The sales clerk was a young man of about 20 or 21. He gave a low chuckle and she felt her insides stir. Something about a deep voice always made her wet.
"A beginners kit, huh? Ever use a plug before?" He asked in his deep grovel.
"No Sir... I mean no. " She couldn't force herself to look at him but did notice how attractive he was when she first came in. Any why in the hell did she just call him Sir?!
He felt his cock twitch. He ran up her items, ran her credit card and then bagged the items, leaving the plug kit out. She looked around horrified, surely he wasn't going to make her walk out without putting that in a bag? Instead, he grabbed the kit, walked away from the counter and to the door where she watched him turn the lock and flip the sign to closed. He walked up to her, standing over her as he grabbed her arm and pulled her into the back room.
It appeared to be the break room or lounge, a large old couch was seated against one wall, lockers adorned the other wall and then a counter with a microwave and mini fridge and sink on another wall. There was a tv sitting on a small stand in the corner. She wasn't sure what he was planning to do but she was nervous as hell. Her palms were sweating and she kept rubbing them down her jeans. She had her long black hair tied up on top of her head and a simple white sweater clung to her chest.
Jessie was average, if not a little on the chunky side. She had an hourglass figure though, small waist with a large chest and curvy hips. She knew she could afford to lose a few pounds but honestly didn't care. If a man couldn't love her curves then he didn't need to be with her.
The guy walked up to her, tossing the plug kit onto the table in front of the couch. He reached up and grabbed the tie around her hair, yanking it out so that her long locks cascaded over her shoulders.
"Ouch! What the hell?!" Jessie asked, bringing a hand up to massage her scalp.
"Shut up and get on your knees." He was holding her chin, squeezing her jaw as he forced her to look at him.
She didn't know why she was doing it but she quickly fell to her knees. She was nervous but felt excitement course through her. She was on her knees in front of a stranger in a sex toy shop and she was about to do something dirty, something slutty. Something she has never done before. She smiled slightly, reaching up to undo his jeans. He didn't stop her, instead placing his hand on her head and petting her as if she were a dog.
She reached into his pants and fished around, wrapping her fingers around his growing cock. He was big but wasn't fully hard yet. She pulled it out, the head glistening with a pearl of pre-cum. She licked her lips and then stuck her tongue out, gingerly touching the tip. She had only given two men head, one of them being her ex. She knew she wasn't good at it but thought that maybe this stranger would teach her.
He was tired of her hesitating. He grabbed her head and pushed his cock against her lips. She opened up and hoped he would take it easy on her. He did, sliding into her throat until her heard her gag. He pulled back out and she coughed, trying to get her breath back. He laughed, grabbing her head again and this time slamming his cock down her throat. Tears filled her eyes, threatening to spill down her cheeks. She fought it, desperately trying to relax her throat to please him.
His cock pulsed on her tongue, her throat tightening around his swollen head as she swallowed. He fucked her face hard and fast, smiling at the pretty little slut on her knees so willing to take a stranger's cock into her mouth. He was horny and didn't last long, holding her head still as his pubic hair tickled her nose and she choked on his length. He exploded in her mouth, shooting ropes of thick cum into her. She swallowed frantically but there was too much and it oozed from her lips, dripping down her chin and landing on her white sweater. She wasn't thinking of anything but swallowing his cum and she never swallowed anyone's, not even her exes seed. He hated that about her, couldn't understand why she would lick and suck his cock but refused to let him cum in her mouth. The one time he tried her, she ran to the bathroom and spit it in the toilet, cursing him for 15 minutes after.
The stranger finally pulled away and she kept her face down, looking at the spots of his cum that splattered her sweater. She hoped they didn't stain but was thankful she wore white. He put his cock away and grabbed her hair, yanking her up. He then began undoing her jeans, roughly pulling the button and zipper and then yanking them down around her thick legs. She was standing in front of him wearing a pair of lace boy shorts. He spun her around and pushed her head down, her ass glaring at him as her panties slid between her cheeks.
He caressed her bottom, his fingers rubbing over her pussy. He felt her soaked panties and knew she wanted to be fucked. He was an animal but not a rapist. He pulled her panties down and ran his fingers over her swollen pussy. Her juices coated him and he began pressing a single digit against her puckered asshole. She moaned, shaking her ass at him in hopes of getting fucked. He then pulled away and she heard him opening the package of plugs, taking one out and throwing it back onto the table.
He squirted lube over the smallest plug, pushing the tip against her ass. He told her to relax and to breathe slowly, his other hand rubbing her clit. He listened to her moans and as they grew louder, he pushed more and more of the plug into her ass. When her orgasm ripped through her, he gave the final push and had the entire plug fit snugly into her ass.
She had never felt anything like it. Pain coursed through her but it wasn't as bad as she expected. When she came down from her orgasmic bliss, she shuddered, a feeling of fullness completing her. He helped her stand and then bent down to pull her panties and jeans back up. She fastened them and then turned to face the stranger, her eyes still cast down.
He explained the procedure for changing the plugs and told her to come back if she wanted help. He gave her his number, walked her back out front and threw her package into a bag before walking her to the door. She was relieved when they got to the door and no one was waiting for him to open back up. She would have died of embarrassment if someone was there and knew she was in the back being a dirty whore with a complete stranger.
Several weeks later she had mastered the changing of the plugs, having actually worked the largest plug into her tight asshole. She knew she would be able to take a cock with no problem and shuddered as she could only imagine the orgasms it would bring.
She turned around, still looking into the full length mirror, and bent slightly. She was checking to see if the pink gem would sparkle. She wasn't going with the intent to flash anyone but if they saw, well then they saw. She was going with the intent to tease. The dress rode up slightly and if she bent down further then the gem was visible. It would have to work, she had nothing sluttier to change into. Jessie grabbed her phone and her keys and ran out of the house, jumping into the car and driving to the bar to join the Valentine's Day crowd.
She sent Joshua a text earlier, Our bar tonight at 9. Please be there. Her heart was racing as she pulled into the parking lot. She scanned the cars and didn't see his but then again she was early. She walked around the side of the building, well hobbled along the side, her four inch heels were a killer to walk in. She also didn't want to walk through the restaurant. Going around the side would bring her in through the bar area and as soon as she turned the corner, all eyes were on her.
