Step Sister with Benefits


Ben was sitting on the sofa with his step-sister Claire. Even though their parents were out of town for almost two weeks, they both ended up dateless on that first Friday night and were watching a movie together. Ben was home from his first year at college and Claire was back from her second year at college for the summer. She was sitting there dressed in an old, white V-neck t-shirt and a blue lace thong. Ben was only wearing his boxer briefs. He couldn’t help but notice her long bare legs and the outline of her breasts and nipples showing through her top. Ben knew he shouldn’t be looking at his step-sister that way but he was a nineteen-year-old guy who was constantly horny. Besides, Claire was almost twenty-one. She is cute and tall and was a decent volleyball player with an athletic build. Ben remembers checking her out in her tight volleyball shorts and how firm her ass is.

Their parents have been married for five years. Ben’s mom had substance abuse issues and was cheating on his dad to help pay for the drugs. His dad, Ben Sr., couldn’t take it anymore and finally filed for a divorce. Ben was traumatized by the divorce, from watching his mom go through her problems, and was happy to be living with his dad living a normal life again.

Claire’s mom, Sherry, caught her dad cheating with his secretary multiple times even after marriage counseling. She threw him out of the house when she caught him cheating again even after he promised his affair was over. Claire missed her dad but understood why her mother had to divorce him.

It was difficult for both Ben and Claire to see their parents dating other people and it was even more difficult when they started getting serious with each other. It didn’t come as a surprise to Ben when his father got engaged. He knew his dad was happier with Sherry and seemed to, and, gave, adjust to the thought of having a step-mom. Ben was getting older and didn’t want his dad to be lonely when he left for college in a few years.

It was a different story for Claire. She was always a daddy’s girl and hoped her parents would eventually get back together. She made life miserable for everyone after the marriage when they all started living together. Claire didn’t like anyone, including Ben. She was also a normal teenage girl with her hormones raging and mood swings. The family situation didn’t make it any easier.

Eventually, Claire and Ben started to adjust and they became not only friends but best friends. Ben was good in math and science so he helped Claire in those subjects while she was good in literature and history so she tutored her step-brother. They looked out for each other and developed a very close relationship. They were so close that some people thought they were blood siblings because he had blonde hair and blue eyes just like Claire.

When Claire went off to college, Ben missed her but also enjoyed being the only child until she came back that first summer. Things seemed to change for Ben and Claire that first summer when she came back home. Ben had just turned eighteen and his body filled out. He was a late bloomer and was happy he now had more muscles and was a couple of inches taller. He was also more popular with the girls at school.

Claire noticed the change in Ben immediately when she walked in the door. She couldn’t believe how much he’d changed. Her step-brother was over six feet tall with a muscular body. He wasn’t an athlete in high school but began working out with buddies when they were getting picked on in school last year.

Ben also looked at Claire differently. He wasn’t sure if it was because he was older or the fact they hadn’t seen each other since winter break but his eyes scanned his step-sister’s body from her long blonde hair to her beautiful face and blue eyes to her full 36c breasts. She was wearing booty shorts that showed off her long, athletic legs and firm ass. He had to stop himself from thinking impure thoughts.

After all the hugs from their parents and Ben greeting Claire, he took her suitcases upstairs to her bedroom. As they were climbing the stairs, Claire’s ass was practically in Ben’s face. He couldn’t help but stare at how her ass twitched from side to side as she went up each step. Ben scolded himself for staring at her ass but the devilish side of him marveled at its perfection. Her ass was firm but still round enough to fill out a pair of shorts, her cheeks peeking out from the bottoms. He had to fight his desire to reach out and squeeze her ass but they finally reached the second floor and he placed her luggage on the bed.

They started talking as Claire unpacked her clothes and put them in her dresser. Ben watched his step-sister closely as they talked about his senior year, prom, upcoming graduation, and college plans. Ben was able to get a glimpse down Claire’s shirt at her hanging breasts when she leaned forward to get clothes out of her suitcases and checked out her ass again when she bent over to put them away.

Throughout that summer, samsun escort Ben and Claire didn’t see a lot of each other between working and their social lives but they did have some days and evenings when it was just the two of them. Their parents took advantage of having older children and began to do things on their own like vacationing by themselves or simply socializing with their friends.

Claire always thought of Ben as her little brother and was casual about the way she dressed in front of him. It was common for her to walk around the house in the mornings or late at night in a sleep shirt or oversized t-shirt. Sometimes Ben would be able to see through the material and get a glimpse of his step-sister’s panties when the light was behind her. He always noticed the way her breasts bounced when not constrained by a bra and it was even better when he could see the outline of her nipples or the way they poked through the shirt when they were hard. Ben tried to make sure he was in the kitchen when Claire came down for breakfast because he would sometimes get a peek at her ass while she bent over in the refrigerator or when her shirt would lift when she reached for something on the top shelf of the cupboard.

After a few weeks, Claire began to realize her brother might be looking at her differently and she began to tease him on purpose. One morning after their parents had left for work, Ben let Claire shower first before they each went to work. He patiently waited in his room for her to finish. When Claire was done, she came into his room with a towel wrapped around herself to let him know he could now use the bathroom. Ben couldn’t help but think of Claire’s naked body under the towel. It barely covered her ass and pussy. He tried not to stare at her long legs and bare feet. He covered his crotch with his hands to hide his growing erection. It seemed like Claire was waiting for him to get up before she left but he didn’t want her to think he was a pervert for getting hard seeing her in just a towel. Claire just kept talking to him and even sat down on the foot of the bed. He kept trying to get a glimpse of her pussy but she had her hand covering herself.

Even though he wanted his step-sister to stay, he had to get to work too. Ben didn’t want to ask her to leave. Finally, she stood up to leave and when she rose, her towel accidentally came apart and fell to the floor. Ben’s eyes widened and he stared at her gorgeous tall, lean, athletic body. Her tits were magnificent, firm, and round. Her nipples were dark and hard. Claire had a fair amount of neatly trimmed hair around her pussy but her lips were visible. He got a great view of her ass when she bent over at the waist to pick up the towel. Ben’s face got red from the excitement of seeing his older sister stark naked, the embarrassment of what he was thinking, and how he was staring at her.

Claire picked up her towel and walked out of the room without wrapping it around her again and said, “Well, we’re siblings so I guess it doesn’t matter that you saw me naked.”

Ben hurried to the bathroom to jump in the shower and he jerked off while in there dreaming about his sister’s naked body. From that day forward, he looked at Claire much differently than before. While he had seen glimpses of her body parts previously, that was the first time he saw her completely naked and he would never forget it.

Things changed for Claire too. She noticed Ben hiding an erection and felt a little bad for arranging to drop her towel in front of him, making things harder for him in more ways than one. Claire liked the idea of teasing Ben and it turned her on thinking he would probably jerk off from seeing her naked. She felt bad for torturing him like that but not bad enough to stop her from doing it again. Whenever she had the chance, Claire would let Ben see her in her underwear, or give him peeks up her skirts or down her shirts. She even began to leave her bedroom door open just a little in the mornings when she was getting dressed. More than once she would look into her mirror and see Ben standing outside her door trying not to get caught peeping in on her.

When Claire knew Ben was watching, she would brush her hair in the mirror, giving him a view of her from the front and back. She would also apply body lotion to her long legs and torso making sure she had her legs open facing the door and taking time to play with her nipples. When Ben wasn’t fucking one of his girlfriends fantasizing it was Claire, he’d be jerking off at the thought of being with his step-sister and all the things he wanted to do to her naked body.

Claire was also having impure thoughts about Ben. She would masturbate to the thought of him watching her and knowing he wanted to do sexual things with her. Ben was growing up from a boy to an attractive man and she noticed he was now a hunk. When she was getting fucked by some of her boyfriends, Claire’s thoughts would sometimes drift into wondering what escort samsun it would be like to fuck Ben. She would then feel guilty and try to get those thoughts out of her head but they kept reappearing out of her control.

Towards the end of the summer, things were silently heating up between Ben and Claire. He began to wear swim briefs around their pool instead of the type that looked like shorts. That’s when Claire noticed his muscular body more, especially his six-pack abs, full chest, and biceps. She couldn’t take her eyes off the obvious lump in his tight briefs. Her step-brother was pretty well hung. They would apply suntan lotion on each other’s backs, doing it slowly to make sure every inch was covered. A couple of times Ben got close to Claire’s breasts along her sides. Part of her wanted to raise her torso and give him access to her tits but she thought better of it. He secretly wished he could get his hands on her luscious tits too.

Eventually, the summer of teasing came to an end and Claire returned to college and Ben began his freshman year at another school. When Ben was doing a load of laundry before leaving for his first year at college, he found a pair of Claire’s panties mixed in with his clothes. He wondered how they got in his laundry hamper. He couldn’t help but wonder if Claire left him a going-away present. Ben kept her panties to use when he jerked off. Sometimes he would feel them as he stroked himself thinking of her ass and pussy in them. Other times he would rub himself off with them. He liked the feel of the satin material against his dick.

Over the course of his first semester, Ben had his fair share of sex with different girls but his thoughts still drifted back to Claire. They would video chat with each other and sometimes she’d be in her bra and panties or a t-shirt with no bra which would fuel Ben to jerk off when they were done. Ben would be shirtless and show off his muscular chest and broad shoulders. He didn’t realize that Claire would sometimes use her vibrator pretending it was her step-brother.

When they were both home for winter break, their mutual teasing continued. This time it was Ben that walked into Claire’s room with a towel wrapped around his lower body after taking a morning shower to tell her the bathroom was now free. Claire was sitting cross-legged on the bed, her panties in full view and her sleep shirt hanging down revealing most of her tits.

She looked up at Ben and said, “You must still be working out. You look like you have even more muscles than this summer. You must be pretty popular with the ladies.”

“Yeah, I found a couple of gym rats I became friends with. They’ve helped me with my routine. The ladies seem to like the results too if you know what I mean.”

“I know exactly what you mean, Ben,” Claire replied while her eyes scanned her step-brother’s body.

Ben then said, “Anyway, the bathroom is all yours,” then his towel accidentally fell to the floor.

Claire sat there and stared at Ben’s seven-inch, cut, half-hard cock. He then bent over to pick it up from the floor while his step-sister stared at his firm, tan-lined ass.

As he was leaving, Ben said, “Well, we’re siblings so I guess it doesn’t matter that you saw me naked,” in a clear reference to what she said when she dropped her towel in front of him.

Claire played with her nipples and pussy while in the shower while thinking devilish thoughts about Ben. Before leaving for work, Claire grabbed her vibrator from her nightstand when she got back to her room and used it to bring herself to an orgasm. For the first time, Claire was on the receiving end of Ben teasing her.

Things weren’t always sexual between Ben and Claire, they would go out to dinner, catch a movie or watch TV together when they weren’t out on dates. They enjoyed each other’s company and their parents were happy that they had a close relationship. It was nice to have someone from the opposite sex to turn to when they needed relationship advice on the people they were each dating. Sometimes, Ben or Claire would make fun of their sibling’s choices for romance, and more often than not, they were correct in their assessments. Ben even offered to pre-screen Claire’s choices of men because she was going through a string of bad dates when they returned to their colleges for the spring semester.

Ben and Claire would video chat several times per week and they looked forward to talking with each other. They were there to offer emotional support to each other, and to share their college experiences with their best friend. They even discussed the possibility of Ben transferring to the same college as Claire so they could share expenses and cut down on some living costs.

When they both got home in mid-May, they were thrilled to see each other in person again and greeted each other with a long, sincere hug bypassing their parents who became second and third in line for an embrace. Instead of dining with their samsun escort bayan parents, Claire and Ben made plans to go out on their own to catch up even though they had been video chatting regularly. Their parents were disappointed not to be invited but they were happy that their children were getting along so well.

As they were talking over dinner, Ben couldn’t help but notice how beautiful his step-sister was. He knew this before but there seemed to be something different about her. Maybe it was that she was older now, almost twenty-one and looking more like a young woman than a pretty girl. His eyes kept darting down to her cleavage and he was recalling seeing her naked and hoping it would happen again someday. He could only wish.

Claire was complaining to Ben about all of the jerks she seemed to attract when dating. She had only been in one semi-serious relationship and was frustrated that she hadn’t found a decent guy yet.

Claire noticed Ben staring at her and asked, “Why do you keep looking at me like that?”

“I’m sorry Claire, you’re such a beautiful woman and a loving, caring person. The right guy will come along eventually. It will probably happen when you least expect it.”

“Ahhhh, you’re so sweet. Any woman would be lucky to have you, Ben. That’s what I love about you, you’re always so supportive.”

Claire also noticed how mature Ben had gotten during his freshman year in college. Being away from home probably helped but he continued to fill out physically also. He was wearing a tight t-shirt that showed off his muscular chest, broad shoulders, and biceps. Claire even teased him about the women in the restaurant checking him out.

Ben smiled and said, “Some women like me for my body, I get that. Don’t get me wrong, it’s helped my sex life but I’m still looking for that special person too.”

“Until that happens, I guess we’re stuck with each other, Ben.”

He laughed and replied, “There are worse people to be stuck with I guess.”

“Gee, thanks a lot,” Claire jokingly replied.

“You know what I mean.”

Claire responded, “I know what you meant but that doesn’t mean I can’t have some fun with you.”

That is what Ben and Claire loved about each other. They could playfully make fun of one another, share their deepest secrets, give advice to each other and share their fears and disappointments. They were best friends in addition to being step-siblings.

As they were leaving the restaurant, Claire asked, “Why can’t I find a guy like you? Any woman would be lucky to have you.”

Ben laughed and replied, “There’s only one of me so you’ll have to settle for second best, I guess.”

Claire shook her head and laughed too. She should have expected that response but she meant what she said, Ben was an awesome guy; too bad they were related. Claire’s statement made Ben think too. He was hoping to find a girl as pretty and down to earth as his step-sister; someone he could talk to about anything, laugh with and enjoy being around without the drama or game playing.

Things were almost back to normal with both siblings back at home for the summer. They each socialized with their friends, got together with family, and dated. When each of them had a date the other couldn’t wait for their sibling to get home so they could hear all about what happened. Most times, they wouldn’t talk until the morning after their parents went to work. Neither Ben nor Claire were shy about telling the other if they had sex with their dates and if they were any good. More often than not, the sex was okay but nothing spectacular. The one thing that did change that summer is both Ben and Claire started to get a bit jealous when the other was going on a date and especially if they had sex.

Before one of Claire’s dates, Ben half-jokingly asked, “So which loser are you going out with tonight? Please tell me it isn’t Jerry. He’s a loser if there ever was one.”

“What’s wrong with Jerry? He’s a nice guy.”

“He’s a jerk.”

Claire was a little angry at Ben for putting down her date like that but when she got home early she had to admit that Ben was right, Jerry was boring and a jerk. Ben took pride in being right and wasn’t shy about letting his sister know that she should have taken his advice.

When Ben was going on a date with Lynn, Claire wasn’t shy about letting him know that she thought Lynn wasn’t very smart and couldn’t hold a decent conversation with anyone.

When Claire said Lynn just liked to sleep around Ben replied, “Why do you think I’m going out with her? A man has needs too.”

“Oh, you’re such a man whore Ben.”

The next morning Ben admitted to Claire that Lynn wasn’t very bright but was good in bed. It got to the point when either one of them was going out on a date, the other would be critical of the other person. They didn’t think anyone was good enough for their sibling. They even introduced people to each other as part of a game. Both Ben and Claire thought they would be better at picking a date for the other person. Claire and Ben weren’t having any romantic connections anyway so they figured it couldn’t hurt. However, it also didn’t help. Neither one of them liked the person their sibling picked for them so they continued to casually date on their own.

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