Sasha's Adventures

Sasha was ready for a night out. School was boring, she wasn't dating anyone and it seemed like all she did was work. She went shopping on Friday afternoon, hoping to find something fun to wear out to the bars that night. She was going with her girlfriends Kim and Theresa, and the three girls always liked to dress up for their nights out.

Sasha was thin with a curvy ass, and decided in the warm May weather that a skirt was the way to go that night. As she shopped she found a clingy top that draped at the neckline, and was only held together by thin straps crisscrossing the back. Her breasts were small but firm and perky, so she knew she could get away without wearing a bra but she worried about the thin fabric and showing too much skin.

As she packed to get ready with the girls at Kim's apartment, she brought a few options just in case. The girls were adamant that she wear the new top with a slinky black skirt and heels. The skirt hugged her hips and went just to her knees, but had a slit along the side. Since she knew she would get hot from the night of drinking and dancing, she pulled her long blonde hair up into a twist. She glossed her full lips to draw attention to them, and they were ready to go.

Sasha attracted a lot of looks that night from her backless top, and Kim and Theresa were similarly showing off their assets and the drinks were flowing. The girls were in a bar district and tried a couple places before settling in at a busy nightclub. They danced and took shots, and Sasha felt her inhibitions loosen. She noticed a cute dark haired guy watching her dance with her friends. He was definitely checking her out but he did not seem like the type to approach her, so as she went to get another drink she grabbed him on her way back to the dance floor. He wrapped his arms around her, and she pressed her body against him ensuring that he could feel her breasts.

He seemed so sweet, and he was cute and she was drunk and horny. She wasn't concerned with making small talk, but she wanted him to touch her and feel her body. They continued to dance, and finally she found his hand on her leg as they moved. As he felt along the slit of her skirt, she felt his hand travel up her leg and around her thigh. The dance floor was so crowded and dark that no one could really see what was going on. He was watching her for a reaction as his hand traveled higher. She pulled her arms around his shoulders and began to kiss him passionately. He continued to move his hand between her legs, and she moved her legs apart to improve his access. His fingers deftly pushed the thin lace string underwear aside, and began to rub her pussy. As he continued kissing her and moving his fingers along her lips, she just kept getting wetter and wanting more. He pushed his fingers inside of her and she was not ready for it to end when the lights brightened.

Soon it was time for the bar to close, and in the drunken haze to catch a cab she lost track of him without exchanging numbers. She chalked it up to a fun night and hoped she would run into him again.

In August as she was beginning graduate school, a friend from class kept asking to set her up on a blind date with a friend of hers who went to the nearby medical school. Sasha finally agreed, thinking there was no harm to having a drink with a guy. Her friend hadn't told her much, but that he was nerdy-cute and nice, his name was Jake, and he would be at a table by the bar wearing a blue shirt.

Sasha nervously entered the sports bar, hoping it wouldn't be too busy for her to find this stranger. Having so little to go on, she dreaded approaching random tables. As she walked around the corner to where the tables were located, she made eye contact with her mystery guy from earlier that summer, sitting alone and wearing a blue shirt. Too surprised to see him again, Sasha looked around to see if anyone else fit the description of her date. But as he smiled at her, she quickly realized that he was there for her.

She ordered a drink and sat down with him, wondering if he remembered her. They exchanged greetings and introductions, and she decided to just see if he knew who she was.

"So, I think we met earlier this summer, at the bars downtown?"

"Yes we did," he answered with a smile, his eyes sparkling

Both were amused by the coincidence and Sasha got over her slight embarrassment. She might be sexually adventurous but it was not like her to let a stranger into her body like that. In brighter light she could better evaluate Jake. She liked his dark hair and eyes. He appeared to be in pretty good shape though not especially muscular, which was fine with her. He definitely had a little bit of a nerdy quality, but in an endearing way. She had come to realize that overly 'pretty' men were dull in bed. Guys who want to impress a woman they might perceive as out of their league put in some serious effort, and she enjoyed reaping the benefits of that. He had this sort of earnest quality about him, and they had similar backgrounds. He was obviously smart and they had good conversation.

She wasn't sure what to do with Jake at this point. She had already shown a promiscuous side to him so she couldn't exactly erase that. She was attracted to him so she didn't really want to cut him loose either. In her mind, she settled on making him her fuck buddy but had to figure out how to tactfully accomplish this without seeming like a complete whore.

So they kept chatting and had a few drinks, and she stayed reserved but genuinely enjoyed his company. Once they were about the only people left in the bar, they made the move to leave. He seemed so nice, surely she was going to get a kiss on the cheek and would probably never hear from him again. But as they walked to the parking lot he surprised her by asking if she wanted to keep talking and go to his apartment. Having no clue what his intent was at this point, she said yes out of sheer curiosity.

She followed him in her car to his nearby apartment. He lived alone in a small and tidy apartment with sparse furnishings. He surprised her when they walked into the place and he quickly turned around and made his move to kiss her. It was so passionate, and she was a little surprised and pleased that he was so forward.

When he pulled back he explained that he had wanted to do that all night and hoped she wasn't offended. She decided to honest with him at that point. She told him that she was attracted to him and enjoyed talking with him but with school and everything she didn't feel like she wanted a relationship. She flat out told him that she very much wanted to sleep with him, but she had no interest in a one night stand. Sex was her stress reliever, and if she was going to sleep with him she wanted it to be a regular occurrence.

Unsurprisingly, he was receptive to her offer. He told her that he had been thinking about her all summer, wondering if he would see her again and if he would have a chance with her again. With medical school he also didn't think he could manage a relationship, but really wanted a friends with benefits relationship. It was probably the most honest conversation she had ever had with a guy, which only made her want him more. So with everything between them settled, she laughed and asked if now he wanted to show her his bedroom.

Smiling, he grabbed her and pulled her in for a long kiss. He then led her down the hall to his bedroom. It was refreshing just to be able to get down to business and not wonder what was going to happen next, or what she even wanted to happen next. If this guy had any skill, she was going to keep him around as long as she could. They both began stripping down, and once she was in her bra and panties she laid down on his bed. He left his boxers on, and moved toward her. Leaning over her, he kissed her gently and then began working his mouth down her body. He kissed between her breasts and ran his hands over her. As he went lower he told her that she forgot something, and pulled off her panties. Then he settled in between her legs and began licking her pussy. He started out slowly exploring her, circling his tongue over her and following the curves and folds of her body. Soon he became more pointed in his tonguing, and he placed a pillow under her ass and pulled her legs up and apart with his hands. He was reaming her hole with his tongue, increasing his place and her wetness. He was logging some serious time between her thighs, and it just made her want to have him even more.

She told him that she couldn't wait anymore. He grabbed a condom and she look a peek at what was in store for her. He had a very nice cock. It was larger than average but not too big, smooth and perfect. She also appreciated his body. He was toned and not skinny at all. He was also not being too nice. He didn't ask her a bunch of questions, instead he just acted. He put her body where he wanted her, and was confident in his steps. After the oral he just gave her there was no need to hesitate with his entry, and he smoothly slid his cock inside of her. He took long, steady, satisfying stokes. As he settled in kneeling between her legs, he grabbed her ankles and pulled them up to his shoulders. He increased his pressure, and pushed her body back so he could reach deeper inside of her, and so his pelvis was creating friction against her clit. This position was enormously satisfying, and she knew he was going to make her come. She began moaning, and felt like it was getting louder with every thrust he made. She cried out " oh god oh god oh god" over and over, and finally felt a flood of wetness between her legs. Dizzy after her orgasm, she knew she still needed to make him come. She turned over and kneeled in front of him facing her ass toward him. He grabbed her hips and thrust inside of her. His cock seemed even harder, so she felt he had to be close. She finally heard gasp, and he stopped moving inside her. She could feel his pulsing cock, and once he finished he slowly pulled out of her.

They spent many more nights together. They would meet up at his apartment late at night, after they had been out with their own friends. They would fuck, talk about their lives, and both enjoyed the arrangement that was the best of both worlds. Their sex was never anything wild, but was intensely satisfying. One night after she had probably had too much to drink, they hooked up and he asked if she wanted to try something different. When she was drunk she was particularly up for anything, and she wasn't likely to deny him much anyway. She was naked on his bed, and he had her lying flat on her stomach. She felt liquid pour on her back, as he dripped oil over her and began rubbing her body. He worked over her back and down to her hips and ass. She moved her legs apart, hoping her pussy would be getting attention soon.

But he had other plans. He dripped more oil over her firm ass, and began spreading it around and pulling her cheeks apart. Soon a finger started circling over her anus. He continued rubbing in a circle, gently fingering the outside of her tightest hole. He did this for a long time, and she wanted to raise her hips and drive his finger inside of her. He separated her legs apart further, and his fingering became more direct as he began sinking the tip of his middle finger inside of her. He had relaxed her so much with the massage that her ass readily accepted him. He began sliding his finger in further, and pulling away a bit. He continued gently finger fucking her, never pulling all the way out. She tolerated this well, so he felt he could pursue the next step with her.

He pulled her onto her side and positioned himself right behind her. He had oiled his cock, and pushed her top leg further in front of her body. With ready access to her anus, he pulled his cock up to it and began rubbing his head around the outside of her slicked hole. She quietly moaned and leaned into him. He decided to go for, and holding his rock hard cock he began to slow feed it into her tight passage. He took his time to allow her to adjust, and slowly pressed into her until he was balls deep in her ass. He began slowly fucking her, just pulling out a few inches at a time and keeping their bodies close and intimate. Once she fully adjusted to him and all her muscles relaxed, she told him that she wanted him behind her. Keeping his cock inside her, she rolled onto her stomach. As she raised her ass up with her knees, he pulled out and positioned behind her. He added a little more oil, and slowly sunk into her ass again. He gave her a slow ride as she acclimated to this new position. He could feel her soaked pussy and knew that would need some attention too, but now he couldn't focus on anything but her ass.

She relaxed and began backing up to him. He followed her cue, and held her hips firmly and began thrusting deeper and harder. As she felt his balls slapping against her pussy with every stroke she felt like she was going to explode. Her tight ass constricting around his cock was also pressing his limits. Soon she started to get very loud, and put her face in a pillow so her cries wouldn't be heard through the thin walls. He grabbed the pillow away so he could hear her moans. This girl was going to come from an ass fucking and he wasn't going to miss it. Her moans and cries grew louder, and he saw her whole body tense up and shake for a moment.

She pulled away from him and collapsed in a heap on the bed, the orgasm's head rush leaving her dizzy. Jake gave her a moment to regroup, and then gave her pussy a lick to remind her that he hadn't finished yet. She told him she didn't know if she could get up again yet as her legs felt shaky. As she was on her back leaning against a couple pillows, he told her not to worry and just stay where she was. He traced his fingers over her dripping pussy. He grabbed another pillow that had fallen off the bed and slid it under her ass. He told her to relax, and pushed her legs up and back. He oiled his cock again and she felt him at the entrance of her anus again. She was nervous about this angle, and concerned whether she could handle any more. Anal sex was her favorite fantasy despite only trying it a few times, but she was definitely worried about reaching her limit. Once he had his head inside of her, he slid the rest of the way in. Her post-orgasm break had reinvigorated him, and he held her legs and watched her face as he fucked her fine ass. It was a tightness he had never experienced before, and as her muscles contracted around his cock he began to feel close. Sasha felt him tense up, and soon he shot his come into her ass. She loved the feel of his cock unrestricted by a condom. She was grateful for the new pleasure he had introduced to the late night visits, and looked forward to what else may be in store for her.