Annas Weekend Friday Night

Author's Note: This is my first crack at writing anything, let alone erotic fiction. Helpful comments and suggestions are welcome but keep in mind that I'm brand new at this.

This will be a multi-chapter story and it features themes of mind control, reluctance, and outright trickery. The story and everyone in it is fictional.

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Anna sighed as she looked at herself in the mirror. Her boyfriend had broken up with her two weeks ago and now she was sitting in her apartment on Friday evening with nothing to do. She had a few friends in the city, girls from work mostly, but they were all either working or out with their own boyfriends.

As she took a sip of wine she thought, and not for the first time, how frustrated she was at being so perfectly average; average height, average chest, average hips, and tonight even her average length dirty blond hair annoyed her to no end. She didn't even have any freckles to break up the monotony of her perfectly average face!

She was tempted to blame her lack of dating success on her average-ness but she knew the problem wasn't her looks or her body, it was her personality or rather lack thereof. As Steve had so bluntly put it when he broke up with her "Anna, you are an okay girl but you really need to find some hobbies and liven up a bit." He wasn't trying to be mean, it was a polite break up, but she'd heard that same thing from nearly every boyfriend since High School and she was about tired of it.

She was looking at the bottle of wine and contemplating a night alone wearing sweat pants and watching re-reruns when her phone rang. It clattered on the table for a moment while she considered ignoring the thing but eventually she gave in and glanced at the screen to see who it was.

The number seemed familiar but wasn't in her contacts. "Fuck it" she thought with a certain amount of irritation while she picked it up and pushed the button to answer. "Even if it is just a damn telemarketer it's got to be better than sitting here in front of the TV doing nothing."

"Hello? Anna?" said a man's voice on the end. It was familiar but she couldn't quite place it.

"Yeah, this is Anna. Who is this?" she replied. She was a shade testy but she really was hoping that maybe this would be something to do, some reason to get out of her apartment for a while.

"I'm glad it's you, I wasn't sure if I had the number right. Hey this is Baxter, we met a couple of months ago when I gave you a ride home?"

"Ahhh, that explains it." Anna thought to herself. She remembered Baxter, he was one of Steve's friends and had given them a ride home from a party after Steve got too drunk to drive. Steve had managed to slur out Baxter's number for Anna to call and beg a ride.

Anna remembered being impressed when he showed up. Baxter was definitely not average; he was tall, darkly handsome, nicely built and drove a very nice car. He was also completely sober, opened the door for her and then basically poured Steve into the back seat. He was polite and seemed nice as he dropped Anna off before taking Steve back to his place.

"Oh yeah, I thought I recognized this number! Thanks again for the ride that night but it's sorta weird hearing from you. Steve and I broke up two weeks ago you know."

Anna could hear Baxter chuckle on the other end as he said "Oh I know, Steve told me about it at work the next day. I've got nothing going on tonight so I was wondering if you'd like to go out for a bit? I can't remember where your place is but if you text me your address I'll swing by and pick you up in say 45 minutes?"

Anna didn't even need to consider it before replying "I didn't have any plans tonight either so why not, I'll be ready when you get here just honk and I'll come right down." "Sounds like a plan, I'll see you in a few." Baxter said before hanging up the phone.

Anna would like to say that as a rule she didn't rebound date friends of an ex but honestly it had never come up before; once a guy had broken up with her she'd never had any of his friends reach out. She wanted to chalk it up to Guy Code but she knew it was because of her personality. Apparently a lack of hobbies or interests aside from pop culture and TV shows coupled with an indifferent attitude towards sex left her without much to keep a guy interested or attract new ones.

As she changed out of her sweats and into a pair of jeans she thought about going bra-less but then decided she didn't want to give any false impressions and put it on. She shrugged into a comfy oversized t-shirt with a Rolling Stones emblem on it, brushed her hair, dabbed on some department store perfume and completed her outfit with a pair of comfy strap sandals.

She was sitting on the couch working through a second glass of wine and contemplating herself when she heard a couple of hopeful honks from out front. A quick swallow emptied the wine glass and she headed out the door with her cell phone tucked into a back pocket and tiny string purse over her shoulder.

On her way down the stairs she promised herself that she'd do her best to have a nice night out and try to go along with whatever Baxter had planned. "As long as it's not too out there or ridiculous!" She thought to herself.

As expected Baxter was waiting out front and he popped out of the drivers seat as she approached. "It's great to see you Anna! Thanks for saying yes to going tonight, I wasn't sure you would since you were dating Steve." he said as he opened the passenger door so I could get in.

"Oh you know, Steve was nice enough but I guess he thought we weren't a good fit and decided to move on." I replied. He smiled at me as I buckled my seatbelt and we continued to make small talk as he pulled away from the curb. She didn't asked where they were going or what they were doing because she really didn't care, she was just happy to be getting out.

Some hours later Anna was again looking in a mirror but this time she thought to herself "This date has gone really well!". She was in the ladies room at the Karaoke place they'd gone too after dinner. Baxter had taken her to a casual family restaurant and they'd somewhat hit it off discussing what they did for work. She didn't do Karaoke but when he'd proposed going to a place nearby she remembered her promise to herself and agreed to go.

She still wasn't sure about the whole Karaoke thing, just like she wasn't sure how much wine she'd had, but Baxter had cajoled her into going on the little stage and singing "Hakuna Matata". He'd grabbed some pictures and video of her singing and she'd made him promise to forward them to her. She'd grabbed a couple pictures of the two of them while she was sitting on his lap and then forwarded them over.

It was getting on towards midnight and the crowd was thinning out when Anna figured she'd swing through the restroom before having Baxter take her home. Somewhere between the conversation, the wine, the new experience of singing, and him being pretty darn attractive she realized that she was a bit...revved up.

To her surprise when she came out of the restroom Baxter was standing at the bar clearing their tab. He was talking to the Bartender as she walked up but he turned and smiled saying "Hope your not upset, it's been a fun night but I figured you'd be about ready to go so I paid the bill." She nodded her agreement and slurred just a bit as she replied "Oh no, I'm not upset but you read my mind. I'm ready to go when you are." Baxter put a hand, a large hand she noticed with a delicious shiver, on the small of her back and gently guided as they went out the door.

While they walked to the car, his hand now resting on her butt, Anna was struck again by how tall he was and how well put together he looked. As they chit-chatted on the drive back to her place he casually put his hand on her knee and that started a slow burn in her core that made her decide she wasn't done with the evening. The growing heat she felt between her legs as his hand stayed on her knee made her glad that it wouldn't take much longer to get there! As the car rolled up outside her apartment building she looked at Baxter and smiled while she said "I don't normally do this but do wanna come upstairs for a while?"

Baxter turned the car off and said "You're inviting us up? I'd love to! Maybe we can look at that magazine collection you were talking about!" while throwing her a thousand watt smile. Grinning Anna hopped out and walked up to the building door, punched in the security code and then held the door open while Baxter got out of the car to follow her upstairs.

They'd just gotten in the door to her apartment when Baxter snapped his fingers and said "I forgot something in the car! What's the code for the door down there so I can get back in?" Anna smiled inwardly as as she gave him the code and thought to herself "He's probably headed back down for condoms."

"No need to rush" she told him, "I'm just going to grab a glass of wine and get comfortable.". As he went out the door she headed to the bedroom took off her sandals, checked the state of her hair, and was walking back out to the living room when she heard him at the door. "Anna! Anna let me in. Your door closed and the other code doesn't work on this one!".

Laughing she made a small production out of pretending not to hear him to until he knocked and said it again, then she drug it out by telling him the code one number at a time. When he finally managed to get through the door and back into the apartment Anna could tell he was a little flustered and after he frowned at the door and then spent a minute explaining what happened she decided she'd led him on long enough. The fact that she was rapidly getting more turned on pushed her to be bolder, to do something that she normally wouldn't.

As he was sputtering about the door she stepped right next to him and looked up expectantly. After a few seconds he got the hint and lowered his mouth to hers for what turned out to be a fantastic kiss, one that had storms of little lightening bolts shooting down her belly. After a short bit he bent his knees, wrapped her in a bear hug, and lifted her up, his lips never leaving hers except to comment, a bit loudly she thought, "I'm so glad you invited us up!"

Anna wondered why he kept saying "Us". She'd heard him say it down in the car but hadn't really payed attention. With her curiosity temporarily overcoming the ache between her legs she replied "You keep saying us...". His wolfish look and reply cut her off "You, me, and you know...the boys." Anna was confused for a second until she realized that Baxter was doing that annoying guy thing where they talked about their junk in the 3rd party. Deciding it wasn't worth fussing over she looked him right in the eyes with a slow wink and loudly proclaimed "You're doing fine so far but I haven't met The Boys yet. I hope they have something special for me!"

Baxter winked back and with a tightening of his arms gave her a near crushing squeeze. It was at this point that Anna realized three things all at once; he smelled delicious, had very muscular arms, and that something firm and hot was pressed up against her! With heat roaring between her legs she whispered throatily in his ear "Forget the magazines for now, the bedroom is that way!"

Without letting her out of the bear hug, something that was making Anna wet, Baxter carried her to the bedroom while they continued to make out and she kept rubbing his crotch with her leg. "Mmmmm," she giggled to herself "I hope he lasts long enough for me to get off too!" Quickly followed by "I'm not normally slutty like this but for some reason this is really doing it for me!"

As they reached the bed Baxter put her down and turned her around so she was facing away from him, grabbed the bottom of her t-shirt and with one swift motion lifted it off her body. Of course Anna helped by raising her arms but still, it's not like she wanted to stop him or, she suddenly realized, could have made him if she'd wanted too.

He'd been nibbling her ears, kissing her neck, and gently rubbing his hands up and down her body when Anna realized that her bra was gone! She didn't remember taking it off but Baxter had started cupping her breasts and tweaking her nipples. Anna's breasts weren't normally very sensitive but tonight the girls were enjoying the attention they were getting and she let out a soft moan of appreciation.

After a few more minutes of rubbing and nibbling Anna realized she was rocking her hips and grinding her butt into his crotch. "Oh, that's a new one for me!" she thought to herself, in fact she was turned on enough that she didn't notice Baxter had stopped playing with her breasts and undone her jeans. She felt them being pushed down though and tried to twist back around but Baxter suddenly gripped her shoulder and held her in place while growling "No, stay put.". With that he let go and firmly pushed her pants down to her ankles, told her to step out of them and then he tossed them in the corner when she did.

Anna was definitely hot, and achingly empty, but she was also bit conflicted as no one had ever man handled her like this before and she wasn't sure how to feel about it. When she felt a finger teasing her pubic hair she looked down and found that Baxter had taken her panties along with her jeans and she was now standing at the foot of her bed completely naked. When Baxter told her to get on all fours on the bed she offered no resistance, especially since he had one hand on her back and another on her butt pushing her forward.

When she was settled into position she discovered that she was wet enough for Baxter to easily slide first one, then two fingers up inside her from behind. "Ahhh, that feels nice! For once I was wet enough to make that easy." she thought to herself. As his fingers pumped in and out of her his other hand reached around to her clit and that's when the fireworks went off! Her orgasm, the first in quite some time, hit hard and fast and she realized she was nearly yelling with pleasure. "It's a good thing the neighbors moved out" she airily thought to herself while he continued to tease her "otherwise they'd be over here banging on the door! Hopefully while I get banged on the floor!" She giggled a bit at the silly rhyme and then caught her breath and bit her lip because Bax wasn't stopping!

Normally Anna was a one and done kind of girl, she just couldn't handle more stimulation on her clit after an orgasm, at least not for a while, but as she squirmed and yelled through the first orgasm Baxter kept rubbing her on the inside and stroking her on the outside. It was driving her crazy and she wanted to tell him to stop but she couldn't pull her thoughts together long enough to do it! She felt ridiculously wet and her chest was heaving hard when Baxter finally pulled his fingers out. She wiggled her hips at the sudden loss but the continued clit massage was driving her crazy. She tried to struggle away but a big hand on her back along with a firm "No" held her in place.

After another minute or so Anna really thought she was going to explode, like literally just fly into a million pieces. Her stomach was flexing as she gasped, stuck between his fingers on her clit and his big hand on her lower back. She had never ever felt like this and was caught trapped in the near agony of over stimulation when he suddenly stopped. After a moment of enjoying the relief she started wriggling her ass but again heard "No" so she held still and listened to the sounds of a belt, and then a zipper, and then the rustling of fabric as Baxter let his pants drop to the floor. With her head drooped down and looking backwards through her legs she watched with disbelief as she dripped on the bedspread. She shuddered and closed her eyes at the sight saying "Baxter if you don't hurry up and fuck me I may just float away."

When Baxter stepped forward a pressure began at her opening and she wanted to cry with relief but instead she whispered hoarsely "Hurry up and fuck me!" which actually made her cringe. "When did I get dirty mouth during sex?" she wondered to herself. She wasn't thinking about that for long though because Baxter started slowly pushing his way inside her. It only took seconds before Anna realized that Baxter had everything she'd felt through his pants! His was easily the largest dick she'd ever tried to deal with "No wonder he calls them the boys" flitted through her head. Nerves she didn't know she had ignited with sensation he continued to stretch her insides, quickly reaching the point that she let out an audible groan while wondering if she *could* deal with it.

When he heard the groan Baxter started pulling back out and said "Good girl Anna! You got the first 2/3rds and I'm sure you can manage it all!" Suddenly encouraged she was quickly panting again as that monster reversed course and started going back in. This time it didn't stop until she felt Baxter's pelvis meet hers which happened shortly after his tip bumped into her cervix and put pressure in place she'd never felt it before. "Why does that feel good?" Anna thought to herself. "Isn't that supposed to hurt?" That thought was quickly replaced with "Jeeesus Christ do I feel full!" Then her thoughts scattered as Baxter started stroking in and out of her.

She'd just been fucked through orgasm number two when she felt a strange new sensation and started trying, with some difficulty, to work out what it was. After another few moments of being railed from behind she figured out that it was pressure on her asshole! "As if that oversized cock of his wasn't enough, " She thought, "Baxter is trying to push his thumb up my ass!"

This was something she had never been interested in and was about to try and stop it when he drew up short and said "This is happening Anna so relax and roll with it.". To Anna's surprised something strange happened; her ass relaxed and with a slight pop and slide the pressure on the outside was gone and replaced by pressure on the inside! Along with it came a sense of fullness that she'd never had before. It wasn't entirely comfortable, she was already being stretched by a big cock after all, but through her haze of lust and confusion she heard Bax say "There you go Anna baby! I knew you could do it and I know you are enjoying it."

Baxter started stroking away again and she quickly decided that she liked the combined sensation, suddenly pushing back against his thrusts and twirling her hips just a little bit, not only to change the angle of the pole she was filled with but also so she could feel a bit more tug and pull on her ass. Baxter figured out what was happening and after working in a second thumb started pushing them both in and out which drove Anna absolutely wild. Baxter just hand to stand there moving his thumbs and stretching her cinnamon ring while she worked herself frantically back and forth on his cock. Anna was so lost to her lust that she didn't even care about the otherwise embarrassingly liquid sounds her pussy and ass were making while she mewled and continued to double penetrate herself on him.

It was somewhere after orgasm number three that Anna started to flag. She'd never had sex for this long and she'd certainly never had sex this intense. She was tired and starting to feel like jelly but even though she was slowing down she couldn't stop chasing the sensations coming from her filled holes. In between strokes she fleetingly thought "It would be nice if we could change up positions before I ride myself to death." When she shuddered and screamed through orgasm number four but still didn't quit Baxter removed his thumbs from her ring and placed both hands on her hips, literally forcing her to stop as pulled out of her now well used cunt.

After he took his hands away Anna collapsed on the bed heaving like she'd just finished a marathon, she couldn't see him but she knew that Baxter was standing there looking at her "Probably smirking that he managed to get away with the thumbs thing." she thought to herself. Once her breathing slowed down a bit Anna heard him say "Okay you, roll off and get on your knees". Anna really didn't know what to say to this, she was exhausted and had no desire to suck on a dick that moments ago had been slamming her cervix while stretching her to bursting but as if by magic she found herself rolling over and sliding off the end of the bed to her knees.