It was Saturday night and Annie took a deep breath as she looked herself up and down in the mirror. She’d been careful with her profile pictures up till this point, making sure her tits had hidden her belly, but there were no camera tricks that she could use on a first date.
Her tits were definitely out, showing off all the cleavage she could on her beautiful Es without showing her nipples. She loved this dress since right below her breast was a sash and then the rest of the dress finished at her knees. It made her tits look beautiful and downplayed her tummy as much as she could. Her brown hair was cascading down her shoulders and she double checked her makeup.
She hadn’t gotten a second date in a while and the last one she had gotten was to come over to the guy’s apartment and get fucked. Annie wasn’t proud of it but at least she felt good in the moment. She sighed heavily and walked downstairs.
Her dad was watching TV with a beer in his hand and her mom was chatting on the phone, working her way through a bottle of wine. Neither of them looked up as she left. When she’d first moved back in with them it’d been all family dinners and reconnecting but at this point she wasn’t sure they noticed her at all.
The restaurant wasn’t too far away, but Annie immediately regretted her heels. She was too poor to call a car for every date but maybe the guy could have offered to pick her up.
Annie got to the place a couple minutes late and a little disheveled. John was waiting and beamed when he saw her. Annie wasn’t sure how to take this, most guys tried to look happy as they juggled how different she looked online and that they might just get lucky. John looked genuinely excited to see her.
He was more or less like his pictures, skinny and tall to the point of looking awkward, not attractive but not unattractive. If he was a couple inches shorter she was sure she’d never notice him in a crowd.
They sat down and Annie was immediately bored. John’s monotone was putting Annie to sleep as they walked through the normal first date conversation. Annie was surprised as John took her hands in his and looked deeply into her eyes as he continued speaking.
With a slight start Annie realized she was in the passenger seat of a car, her stomach was sore like she’d been twisting for too long, and an oddly familiar taste in her mouth. She swallowed and was sure of what she’d just done. Annie smiled as she looked at John, “I had fun tonight, and we should do it again some time.”
John nodded his head and Annie left the car. She walked past her dad and went straight to her room. Annie wracked her brain as she cleaned off her makeup and slipped out of her dress. She could remember everything about the date up until they sat down and then things got foggy.
She pulled on a pair of short shorts and a sports bra. Annie felt like she’d had a good time and clearly she sucked his cock so maybe it wasn’t so bad. She took out her phone and was looking at yoga videos for beginners before she stopped suddenly.
Annie never did yoga. She never exercised. Normally after a date like that she’d watch reality TV and maybe masturbate. She couldn’t explain her urge to do two hours of yoga but without thinking too hard she let her body continue. It’d be good for her after all, she always had meant to do this shit.
Two hours later Annie felt like death. Her bra and shorts were sweated through and she could barely lift her legs or arms. She shuffled to the bathroom and turned on the shower.
She stripped down and looked at herself in the mirror. She already felt bad about how difficult stretching was, now that she saw how beat she looked she felt even worse.
The warm water felt amazing though. As her sweat washed away, so did some of her disappointment in herself. In just a couple minutes she was feeling good enough to start tracing her thick little lips through her thick pubic hair.
She vaguely remembered that she had an appointment for tomorrow at a salon to give her a full wax, something she absolutely hated but it seemed necessary when she booked it at dinner. Annie pushed that thought away and focused on the feeling of warm water rushing past her clit as she squeezed it delicately.
She ran her other hand down her ass and began reaching around to her pussy, but stopped suddenly. She didn’t know why but she wasn’t supposed to put anything, not even her fingers into her hole. Reluctantly she pulled her hand back before realizing that she could penetrate her asshole. She hadn’t done this before.
She pressed her middle finger against her asshole feeling how tight it was. Annie tried to relax as she pushed harder and harder against her hole. She began rubbing her finger in a circle trying to inch her way in. After a minute she finally gave in a little and she got the tip of her finger into her ass.
Annie pressed the tip of her finger as deep as it’d go, which wasn’t far at all. She barely had her first knuckle in before she stopped. It hurt more than it aroused her. She poked her head out of the shower and grabbed a bottle of lotion.
She squatted down in the back of the shower and applied the lotion to her finger. Rubbing the lotion in around her hole she pushed in again. It was still tight but between squatting and the lotion she got all the way to her second knuckle.
She pulled her finger out and reapplied the lotion. Approaching from the front, Annie pushed her finger in. She was able to get it all the way in and noticed that there was a spot that actually felt quite good.
Standing back up, she kept her finger in her ass, gently rubbing, as she began squeezing her clit with her other hand. Her orgasm began building. She noticed that pulling against the side of her hole, painfully stretching it, gave her great stimulation. It only took moments before she started shaking.
Annie knelt back down and finished herself off on the floor of the shower. She pulled her finger free and washed her hands in the running water. Panting she got up and finished her shower. As Annie returned to her room she collapsed on her bed and fell right asleep.
Annie couldn’t say why, but she kept her new habit going all week. Every night she’d do two hours of yoga, masturbate in the shower, and go to bed. She hadn’t even thought about dating until Thursday morning she got a text from John, “Hey, let’s hang out tonight. I’ll pick you up at 7.”
Annie was happy that he’d messaged her although she’d more or less forgotten about him. She was confused though as she noticed what she’d texted him during their last date. She could vaguely remember it now, but she thought it was a good idea to go to the bathroom and send John pictures of her tits and hairy pussy.
Annie shook her head but quickly forgot about the texts. Right at 7 John was at her house. She got in and made small talk on their way to the restaurant. Annie was way over dressed for the dive John took her into. She was surprised that it was in a seedy strip mall that also housed a sex toy shop.
They got burgers and sat down. Annie couldn’t remember what she thought was interesting about John. She was sure they had had a good first date but not why and didn’t see how she could have had a good date with such a boring guy.
He reached over and took her hands and her mind entered a daze. Annie swallowed as she realized she was in John’s car outside her house. She shifted in her seat as she felt something under her. Not just under her, but inside her. She smiled at John who was saying goodbye to her.
She stepped out of the car and wondered what was in the shopping bag she was carrying. She walked into the house and saw her dad on the couch with a beer in his hand, her mother was nowhere to be seen.
Annie entered her room and put the bag on the bed. She took a breath and opened it up. On top of the contents were the pair of underwater she’d been wearing that night. She lifted up her skirt and sure enough she could see her bald little cunt. More than that, she could see something sticking out of her ass. She reached down and pulled out a small inch and a half wide butt plug.
Without a second thought she reinserted the plug and returned to the bag. The contents were pretty simple. Two more butt plugs, one about three inches wide and one five inches wide, a wand vibrator, and a large bottle of lube.
Annie had never had any sort of sex toy before, so the idea that she’d gone to a sex shop on a date confused her. Before she thought too hard on it though she remembered her yoga. Instead of what she’d been doing the previous weeks, this time she looked for kegal centric practices. She changed into a sports bra and spandex shorts, leaving the butt plug inside her she started her yoga.
Two hours later Annie was sweaty and ready for a shower. She didn’t head to the shower, but instead walked downstairs. Her dad was still on the couch, but he looked like he was asleep. Annie ignored the TV that was still playing and settled down in front of her dad.
Annie gave him a shake, and after he didn’t move she slowly pulled down his sweat pants. Annie hadn’t thought about her dad’s cock before but now that it was in front of her she realized he had a nice member. It was so nice in fact that she had to taste it.
Her dad’s cock tasted salty but Annie didn’t register it being foul. In no time she was bobbing her head up and down on his rock hard shaft. She almost stopped when she felt a hand grip the back of her head, but the grip tightened and began driving her face harder and harder into his crotch.
In a couple minutes of him abusing the back of her throat he released. Annie sucked hard as she removed her mouth, not spilling a drop of his cum. She got up, swallowed, smiled, and went to the shower. She came hard, fucking her asshole with her new toy.
The next day, once Annie had finished her yoga she went down to her dad. He was awake this time and looked pissed. Annie got down on her knees in front of him and looked up, “Is everything okay daddy?”
Without saying a word he pulled his pants down with one hand and pulled her face down with the other. Annie relaxed and let her dad pound away. It took a little longer this time but once he was done, Annie got up, swallowed, said goodnight, and went to her shower.
This continued for a couple of days when one day before Annie could start her yoga, she got a knock on the door. She had been changing and was only in her spandex and butt plug. She opened the door to her dad, “Hey Daddy, what’s up?”
He pushed her inside. “I’m going to fuck you, you little slut.”
Annie couldn’t imagine her dad saying this, but stepped back and pulled down her spandex, trying to hide the butt plug as she removed it with the shorts, “okay Daddy, just not in my pussy.”
He looked her up and down. This is what his little girl had become? She was once so small but now in her twenties she was chubbier than most guys would fuck, and clearly a whore. Damn though, she had the most gorgeous tits he’d ever seen.
He grabbed her arm and twisted it, forcing her face down on the bed, “Okay whore, relax that ass of yours.”
Annie had never had anal sex and she was sure her dad’s cock was significantly larger than the plug but she was lubed up and just relaxed as he pushed the head of his cock into her.
He entered with relative ease but was still stretching her in a way she hadn’t thought possible. He released her arm and grabbed some of her fat hips. It only took moments before he was pounding away.
He was hitting her in the right way to get her going but not quite enough to get her to orgasm. She reached out and grabbed her vibrator. As she pulled it close and started to bring the vibrator to her clit her dad grabbed her hair. He pulled till she arched back lifting her chest off the bed.
He was grinding his cock into her ass as he wrapped an arm under her arm and below her breast. Annie applied the vibrator to her clit as her dad released her hair and took hold of one of her nipples.
She held in cries and he pulled hard on her nipple and continued fucking her ass. She began to shudder and released a heavy sigh just in time for him to drop her back to the bed and finish in her ass. He left without a word. Annie got out the three inch butt plug, lubed it up, inserted it, and got back to her yoga.
A variation of this continued for the next week and a half. Annie had moved from the three inch plug to the five inch, and was getting more limber and her pussy was getting tighter. Annie had almost forgotten about John when she received a text Friday morning, “Let’s meet up, I’ll be by at 7”
Annie was waiting at the sidewalk when John pulled up. He didn’t say much as they drove to an apartment building. Annie followed him up to a room and he opened the door. The room was decorated like a woman lived there, and sure enough there was a little blonde girl sitting on the couch.
Annie was confused what was going on when John interjected, “Annie, this is Alex, she lives here. I figured we all could have some fun.” Before Annie could respond John was standing in front of her holding her hands.
Next Annie knew, she was in the bathroom with Alex and they were both undressing. Annie wanted to break the silence but didn’t know what to say to this girl. At first Annie had thought she was hot but now that she could really see her, she was too lanky, flat chested, and had a permanent scowl on her face. Maybe her teeth were too big too. But there was something oddly familiar about her.
Annie shook her head and took hold of the enema. She didn’t fully remember why but she filled the enema at the sink and Alex stood over the toilet facing the wall. Alex bent forward and stuck out her skinny little ass. Annie chuckled at the contrast between Alex’s tight asshole and her clearly loose pussy. Alex’s bald lips hung like flaps and as she bent forward her hole gaped slightly.
Annie smiled as she pressed the tip of the enema against the tight asshole. She couldn’t get it to give so she bent forward and gave her a couple of good licks before licking the tip and trying again. She was able to ease the tip in and fill Alex up. The third full enema came put clean and the fourth was just for good measure.
Annie knew it was her turn and she took Alex’s place over the toilet. Alex had a much easier time filling Annie’s ass. They wiped each other down in the shower making sure their legs and cunts were clean. The moment they were dry the two girls walked back into the living room.
John looked impatient but a sick smiled curled up his face as he looked Alex up and down. It clicked for Annie as she saw the two lanky bodies close together. John cleared his throat, “I told you that you were a slut. You kept saying you weren’t but now look at that wide fucking pussy.”
Annie watched as John knelt down in front of Alex and pulled her pussy lips apart. He let out a laugh as he stood back. “Mom and Dad always put you on a fucking pedestal but I knew how simple and slutty you were.”
John led Alex to the couch and had her sit down. He reached down and grabbed the nipple of one of her flat breast. He twisted hard as he looked into her blank face. “It took me months to find a girl as dumb and easy to influence as you. When I finally did it was a fat pig.”
Annie didn’t like the way he looked at her as he walked back to where she was standing. He slowly walked behind her. A slap on her ass rang through the room as Annie held back a whimper. “Damn look at her fucking jiggle. I kept looking after I found this pig, but you two are truly just the two easiest to influence girls in town. Alex, I had this girl fuck her own dad multiple times. He’s probably at home now wondering why his dick isn’t in her.”
Annie could have cried but although she could hear and register everything John was saying, nothing seemed to stick. She didn’t understand how she fit into all this. John returned to his sister and stripped down. He looked over at Annie, “Come over and pleasure my sister’s saggy cunt you ugly pig. Fist this little slut.”
Finally Annie knew what she was doing here. She moved quickly to the floor in front of Alex and noticed the bottle of lube already there. John worked Alex’s legs behind her head and brought the tip of his pens to his sister’s lips.
Without waiting to be told what to do again, Annie lubricated her hands and began working one into Alex. The first four fingers went in with ease. Annie was mesmerized by how warm and soft Alex’s pussy was. She slowly rotated her hand until she was comfortable fitting her thumb in as well. Alex let out some gurgling noises as her brother pounded into her face.
Annie focused on her own hand as she balled it into a slippery fist and pushed it deep into Alex’s cunt. Annie figured John was right, Alex must be a huge slut if Annie’s fist fit so easily into her. It never occurred to her what somebody would say about her own loose asshole.
It dawned on Annie that she was supposed to be pleasuring Alex, not just pounding her loose cunt with her fist. Annie lowered her face to Alex’s clit and began licking. Alex immediately reacted to the new stimulation. The noises from her throat changed from just trying to breath around John’s cock to those plus slight moans of pleasure.
Annie was pushing her fist in and out of Alex, pushing it at least nine inches into the small blonde. Annie felt Alex start to tense up and soon it became difficult to maintain her cadence, but by putting her weight into it she kept pumping her fist as she sucked harder and harder on Alex’s clit.
Annie barely noticed a sound from Alex but when her body went limp, Annie knew she had cum. John dismounted the blonde and Annie pulled her fist from her pussy. They both watched as her gaping hole slowly closed, but stopped while still two inches open.
John shook his head and pulled his sister’s legs down. He led her to the coffee table. “Okay slut, saddle up on the table with your ass and cunt hanging off.” Annie watched as Alex worked her legs down either side of the low wooden table and bent forward. Alex’s goods were on full display and John clearly had easy access.
He smiled as he turned back to Annie. “Get your hand back into this slut with your palm facing up.” Annie obeyed and had her hand back inside Alex’s warm hole in no time. She sat there on the floor waiting for her next instruction.
John smiled and stepped over the fat girl to line his cock up with his sister’s asshole. He wiped the lube that had dripped onto her ass away. Annie could feel as John’s cock pressed against Alex’s tight hole. She remembered back to how much trouble she’d had the first time and winced inside knowing what Alex was about to experience.
Annie had a great view as John kept pushing against his sister’s hole. He tried pulling her ass apart with his free hand and Annie decided to help. With her free hand she griped one of Alex’s boney cheeks and pulled it away. John grunted as his cock began sliding in. With a little more effort and some whimpers from Alex, John got his cock all the way into his sister. Annie enjoyed how she could feel his pulse in his cock through Alex’s pussy walls. It was an odd sensation to have her hand enveloped in warm moist velvet as a cock brushed her palm.
John leaned forward and rested some of his weight on Alex. He grabbed a handful of her hair and jerked her head back, “what I really wanted to do was tear your ass apart and leave you bleeding, but I figured this would be more fun and keep you out of the emergency room.”
John looked back at Annie, “Jerk me off piggy.” Annie hesitated but understood. She adjusted her hand so she cupped John’s cock in her palm and began working it back and forth. Annie could feel the head of his shaft distinctly through the thin membrane separating her pussy from her ass. John groaned as Annie began rubbing harder and faster.
Annie felt John cock twitch and he slowly pulled out of Alex’s ass. Annie didn’t need to be told to as she pulled her hand out of Alex, spread the girl’s ass cheeks and sucked up John’s cum. Annie sucked and swallowed it all. John sat back on the couch, looking at the two girls.
John sat there a couple minutes more before sitting back up, “Slut, get off the table. Piggy, lay on you back on the table and work your legs behind your head.” Annie was honestly excited to obey. She’d gotten to the point where she could get her legs behind her head a couple days ago and had wanted to share it with somebody. She hadn’t shown her dad because she knew he’d try to fuck her pussy.
“Okay slut, suck my cock and clean it up from your ass while you fist this piggy’s shitter.” Alex dropped to her knees and lubed up her hands. She had to twist as her brother face fucked her and she worked her hands into Annie.
Annie knew Alex had small hands but she was embarrassed at how quickly the girl was up to her wrist in her ass. Soon Alex was deeper than the butt plugs or Annie’s dad’s cock. This allowed her to feel a completely new stimulation. Unlike the pleasure she normally felt, this was more like being stuffed way beyond her normal limits.
Annie breathed into the stretching, relaxing more with each exhale. She was disappointed when Alex removed her little hand. Before she knew it though, she felt both of Alex’s hand begin stretching the entrance to her loose asshole. Annie’s heart quickened as she realized Alex was going to fuck her with both arms.
She got distracted from the sensations as John pulled his hard cock out of his sister’s mouth and positioned it in front of Annie’s cunt. “See sister, even a fuck pig like this one can have a cute tight little slit. Her pussy is worth more than all your holes.”
Alex just continued fucking Annie’s ass, working her arms in past her wrists. Annie watched as John worked his cock into her pussy. The month of no penetration and kegels had tightened her up and now even John’s average cock felt like it was pushing her limits. The combination of the fisting and fucking brought Annie to her brink.
She spaced out as John pounded away at her pussy but she was brought back to the moment as he leaned forward and gripped both her nipples. She would have cried out normally but she just gasp as he pulled and twisted, twisting her entire breast. John held both nipples in one hand and then the other so he could keep twisting.
Annie saw stars as her breast completed a second full rotation and her body began shaking. Through her gasps she didn’t notice John release her nipples and pull out of her. She laid on the table for a couple minutes before she noticed Alex had licked her cunt clean and was back to sucking off her brother on the couch.
John pulled Alex off his cock and looked at Annie. “You’re free to go piggy. Just remember your cunt is mine and to do your stretches.” Annie released her legs and got dressed. As she left Alex was lowering her ass down onto John’s cock as he gripped her by her cunt.
Annie sighed as she got to the lobby and realized John had driven her here and it was too far to walk. There was a guy just coming in. He was fairly unattractive and fatter than even Annie, but Annie saw her opportunity. “Excuse, could you give me a ride? I don’t have enough for a car home.” She gave him her cutest look and she saw the gears turning in his head.
Before he had a chance to reconsider she stepped up against him and gripped his cock through his shorts. Pressing her fat tits against him she whispered, “I’ll make it worth your while.”
Annie wished he’d have showered more recently but as her head bobbed up and down on his cock she was happy to be on her way home. It was almost time for yoga.