Sasha's Adventures

At nineteen Sasha was keeping a busy schedule but a dull social life. She was a full-time student at a private college and worked two jobs during most of the year. She did very well academically, and was also blessed with good looks. She was thin, and her breasts were small but firm. She had a curvy ass and long blond hair. Those assets served her well at her bartending job. She was putting in late nights pouring drinks at a sports bar. The uniform shirt was boring, but she always paired it with snug pants or short shorts to accentuate her ass. There weren't often customers she was interested in flirting with, but she was very friendly to ensure good tips.

Sasha preferred working her night shifts with a particular manager, Brian. He was quiet but funny, and always fair with the staff. She liked him as a person and had to admit to finding him attractive as well. He had played football for a Big Ten school in his younger days and still looked the part. He wasn't overweight at all, but he was solidly built with a thick torso and broad chest. He was clean cut with warm brown eyes and sandy blond hair, and he always looked professional. As cute as he was, Sasha didn't really foresee anything happening with him as he was in his late thirties and seemed kind of reserved.

Since she was always the last person to finish closing duties, some nights it was just Sasha and Brian walking out together. After one particularly busy shift, when Brian was done with closing paperwork he came out to the bar to see how close Sasha was to finishing. They decided to have a drink and sit down after such a long night. They talked and finished counting her register drawer, and Sasha got up to get ready to go. As she turned around to walk out from behind the bar, she hadn't realized Brian had walked behind her and she walked right into him. He grabbed on to her so she didn't lose her balance, and when she looked up at him and they made eye contact they both moved in to kiss. He had firm lips and she found him to be an excellent kisser. They separated and walked out from behind the bar, neither saying a word. She worried that he was going to be regretful, as he didn't really seem the type to hookup with an employee.

But when she looked at him again, all he said was "Want to get out of here?"

She simply said sure, and he directed her to follow him. He lived in a house out in the country, and she followed him along wondering where the night would lead. It was a cold midwestern night, and upon arrival she quickly followed him into the house. He offered her another drink and she accepted and looked around. It was a very typical bachelor house, and while she knew he had a roommate there was no sign of anyone else there that night.

He had changed out of his work clothes and got beers for them both. He asked if she wanted to get in the hot tub, and pointed toward the deck. She thought he was a little crazy because it was so cold out, but figured what the hell and they walked outside. They both quickly stripped down to their underwear and climbed into the hot water. She turned away and threw off her bra before entering the water not wanting to get it wet. Outside of the city, the sky was lit up with stars and the deck overlooked the hilly countryside. With the snow on the ground it was a beautiful view, and they sat together and drank and talked.

Sasha decided to make her move, and she climbed onto his lap facing him. They began kissing again, and she raised her hips so she could work her pussy over his cock. Still in his shorts, he was already hard when she climbed on top of him. She continued to grind her hips and put pressure against his cock. He had grabbed onto her ass, left uncovered by her lacy thong, and pulled her against him. As she worked her body over his, he pulled his mouth away from hers and began focusing on her breasts. Rock hard from being cold and wet, his warm mouth swirling and sucking her nipples felt heavenly. She pulled her head back and moaned, as his mouth teased her nipples and his cock teased her opening. Separated by two thin pieces of fabric, he rubbed his cock against the entrance of her pussy and she could begin to feel that he was very thick.

He moved his hands around and pulled the strip of underwear away from her pussy, and gradually began fingering her. His hands were large, so he started slowly and gently, running his fingers across her pussy and teasing around her tight hole. He continued mouthing her nipples, and she moved her hips down to drive his fingers deeper inside of her.

They decided to move things inside, and grabbed towels and ran inside as fast as they could. Both stripped of their remaining wet clothes, and Sasha followed him into his bedroom. It was dark, with just a crack of light creeping in from an open door. He stood in the middle of the room drying off, and then reached out for her shivering body. He wrapped his arms around her and pulled a towel around her shoulders until she warmed up. He gently pulled her back a couple steps until she was at the edge of the bed, standing before him as he sat down. He continued rubbing his hands down her body and over her ass. She turned around to face him, kissed him hard and dropped to her knees as he sat on the very edge of the bed.

His cock was huge. The length didn't even register with her at first as she was so shocked by his girth. Sasha loved a challenge and was determined to satisfy her boss. She began working her lips and tongue around the head, building up so she could begin to take him deeper down her throat. He was so big around it was almost hard to breathe at times, but she was undeterred by this huge but beautiful cock. She continued as long as she could, alternately swirling her tongue around his head and pulling his length down her throat. Finally, she could wait no more.

"I want you inside me."

He leaned over to a bedside drawer, and she lie down on her back. She knew it would take some effort to get him fully inside of her and this was the best way to start. He kneeled between her legs putting on the condom, and then pushed her knees back. She felt him at her entrance, circling around her tight hole. He leaned his body over hers, putting his weight on one arm while he kept his other hand on his cock. He pressed against her, and slowly she felt him enter her body. She was so wet that it wasn't painful, but she definitely had never taken anyone inside of her like him before. He continued to gradually feed his cock inside her, making an effort to let her body adjust to him. Once he was fully inside of her, he increased his speed and leaned his body upright. He pushed her knees back toward her chest so he could strike deeper, and continued fucking her hard and steadily.

He abruptly pulled out of her and tapped her hip. "Turn over."

She flipped over and pulled up on her hands and knees in front of him. Now he really started pounding her, holding her hips and thrusting his cock deep inside of her. She did not get orgasms easily, but she was getting closer with every thrust. Finally she cried out, and as she could feel her pussy tense up as she came, she felt him inside of her throbbing. Once she could feel he was done coming, she slowly pulled away from him and he withdrew from her. She rolled onto her back and tried to catch her breath. He lay next to her and she could hear him breathing hard and see his chest rising.

They stayed in bed in silence for a while, so long she thought he had fallen asleep. She debated whether to quietly dress and go home, or just pass out naked in his bed. She moved toward the edge of the bed and stood up. "Going somewhere?" he asked. She explained she thought she might go home, and joked that since he was old she thought he was probably done for the night.

"Oh, is that what you think?" he asked with a smile as he stood up. "I am not even close to done yet."

He pulled her naked body against his from behind. She could feel his cock twitching as it again grew. He pushed her hair aside and began kissing her neck and trailing his mouth down her back. He turned her body to face a chair in the room, and he slowly pushed her back down so she was bent over in front of him leaning her hands on the chair. He began teasing his cock outside of her, pushing the head in and out. He reached his hand under her, and began lightly rubbing her clit. She soon felt herself getting wet as he rubbed over her pussy with his cock and fingers. She arched her back and pushed into him, pressing his cock inside of her.

He stayed behind her, thrusting between her spread legs. She leaned down further pushing her as higher to him so she could feel his body against her swollen clit. His hands gripped her hips, and he pulled her into him harder to match his deep thrusts. Her pussy was sore from the last encounter, so she could only imagine how she was going to feel after this. As his thrusts deepened he suddenly stopped and pulled her body up into his arms. He moved her back on to the bed, kneeled between her legs and threw her legs up to his shoulders. Quickly moving a pillow underneath her ass, he began powerfully thrusting again. His strokes were hard but steady and confident. She loved how he was quietly in control and skillful in his moves.

Finally he came, and she felt his pulsing cock inside her become less rigid. They stayed in bed for the night after this, and she was satisfied from the events. As expected she was sore from the performance of his monster cock, but she couldn't wait to experience it again. He was ready to go again in the morning, but she had to beg off and take a break. Fortunately she didn't have to wait long to experience him again.

The following weekend they found themselves alone again on Sunday night. It was a slow night so Brian let everyone else off early, and Sasha didn't have any morning classes on Mondays so she was happy to take her time. Once the doors were locked, she rushed to clean up hoping to have another evening with Brian. After he finished his work in the office and came out, she asked if he would be up for a drink figuring if he said yes it was going to be a good night. He agreed and suggested they get out of there and grab a beer at his house, and Sasha was thrilled.

Once again they went back to his empty house. Sasha had a gym bag in her car with comfortable clothes, and asked if he minded if she took a shower so she didn't smell like a bar anymore. He agreed that was a good idea for both of them. The shower was definitely not ideal for an intimate moment as it was a little small, but they soaped up each other's bodies and kissed and rubbed each other all over. Once they got out, they went to the bedroom and Brian asked her to get comfortable on the bed. He put extra pillows behind her so her upper body was raised, and turned on a dim lamp. He soon crawled between her legs, and just because of his sheer size she had to spread her legs relatively far apart to accommodate him. He began kissing her inner thighs, slowly moving up. He used his large hands to press her legs further apart and exposed her as much as he could. Soon he was lightly running his tongue up and down her pussy lips, and then began making more assertive movements with his tongue. As she averted her eyes and threw her head back in pleasure, he directed her to look at him and he continued to maintain eye contact as he worked his tongue over her. He used his fingers to pull her lips apart, and began sharply tonguing and sucking her clit. He was skillful with his tongue and he rarely broke his gaze with her, preferring to watch her reaction as he probed her most intimate region.

This was powerful oral sex, and soon she felt the urge to come. It was like no other orgasm she had experienced. She felt a rush of warmth flood her pussy and was utterly exhausted when he finished. She fully intended to return the favor, but this "old guy" was definitely tiring her out. He lay on the bed next to her and teased her about her lack of stamina. She had no idea if this man knew how skilled he was, but she knew she was lucky to be in his bed.

Once she had caught her breath and felt her heart slow down, she knew it was his turn. She moved over his body as he lied on his back. She kissed him hard and intensely, pulling the taste of her pussy off his lips. She used her hands and mouth and she worked her way down his body until she settled between his legs. She began working her tongue over his cock, licking up and down his shaft. She began taking him deeper until she was able to go down on him with deep thrusts down her throat. She would occasionally look up at him, and he was always watching her. He loved the sight of her full lips wrapped around his cock. She kept going, licking and sucking him, tonguing the tip of his head and deep throating him. Finally she felt his cock start to throb, and his sweet cum filled her mouth.

She moved over to lie next to him, and he told her that he wanted more. If he was turned on, he would get hard again. She began stroking his cock and kissing his strong body. He leaned in and began flicking his tongue over her nipples. He pulled away and asked her to show him how she liked to be touched. Sasha didn't typically lack confidence around men, and maybe it was his age or position of authority but she felt a little self conscious in front of him. He had a quiet authority about him, a way of asking her to do things in way that was polite but made it clear it wasn't up for debate. She responded well to that, and leaned back spreading her legs. She ran one hand over her breasts, rolling her nipples in her fingers and the other hand gently explored her pussy. She couldn't look at him while she touched herself, but knowing he was watching made her wet very quickly. She finally looked up and saw that he was fully hard. She sat up and pushed him down. She was ready to ride him.

She straddled over his broad form. He was so much bigger than her that positioning alone was a bit of a challenge, but ultimately it was an advantage. She settled herself over him and guided his hard cock into her waiting pussy. She pushed herself down on him, and began to ride him just as he had to her. Not fast, but steady and hard. He closed his eyes and she could see the sheer pleasure on his face. After a bit, she decided it was time to turn around. She turned her ass toward his face, and leaned over to take his cock from the other direction. His body gave her the perfect support to maximize her thrusts, and she pulled away as far as she could with him still inside of her and went back down. She was careful to maintain her balance, and soon he couldn't take her deep thrusts over his cock anymore and he came.

Brian did the scheduling at work, and coincidentally he and Sasha closed many nights together. They managed to be discreet and no one was the wiser, but considering all the places around the bar and office they began fucking, it was somewhat miraculous that no one ever caught them. Sasha hoped Brian would not be her last older man, as her sexual experiences with him were fulfilling and he could give her orgasms that she didn't even know were possible.