Mia Tutors Her Virgin Brother Ch. 01

Mia didn't know that when she sat on the sofa with her feet propped up on the coffee table even though she kept her knees together, the bottom of her gown dropped down, exposing her bare pussy. Oliver noticed when he got up to get something to drink making his jaw drop open. Mia asked if there was something wrong and he just walked away. However, he kept making excuses to get up from the sofa so he could get another peek at Mia's exposed pussy. Of course, he jerked off later that night over his good fortune to see all of Mia's naked body again.

What made that evening so erotic was the fact that Oliver was getting quick glimpses of Mia's body and only when the light was behind her or when he would pass by her while she had her feet up on the coffee table. They were short bursts of voyeurism that teased him and left him wanting more.

Things remained as they were for a couple of weeks with Oliver fawning over Mia and getting quick peeks at various parts of her body. He also had a more vivid fantasy when she was fully clothed but would undress her with his eyes. Oliver's twentieth birthday was also creeping closer and that meant the clock was ticking on Mia's goal to get him laid while he was still in his teen years.

Mia approached Jenny for help. Mia knew Oliver had a big crush on her best friend so she seemed like a natural ally. She confided in her that her brother was a virgin and needed some help finding a willing partner. Even if it were only for a date so Oliver could gain some experience being alone with a female for an evening, it would be a major help. Jenny said she'd think about it.

One evening, Mia met Jenny out for dinner and that's when Mia pressed her friend further for help with Oliver. Jenny was extremely hesitant. She knew for years that Oliver had a big crush on her but Jenny didn't like the idea of leading him on to think that a relationship was possible. Mia explained that she would make it crystal clear this was only a practice date to help him get over his shyness with women. Jenny was still reluctant but Mia kept pleading with her until she finally gave in.

"I suppose asking you to fuck him is out of the question."

"Oh come on Mia, do you expect me to fuck your little brother?"

"It would be nice. He's got to get laid sometime."

"Yeah, but why me?"

Mia then jokingly replied, "Come on Jenn, he wouldn't be the worst guy you've slept with."

That was a joke only best friends could tell but Mia was half-serious too.

"I'll think about it but don't count on it. You should be happy I'm going on a date with Oliver."

"Oh, I'm thrilled but you know, if things go well...."

"You owe me big time, just to date him."

"Alright, alright but think about it."

"Okay, I'll think about it," Jenny said just to end the conversation.

When Mia told Oliver she had arranged a practice date between him and Jenny, he began to panic so badly that he almost hyperventilated. A date with his dream girl was almost too much for him to deal with but Mia successfully calmed him down to the point that he even realized that it would help him with his shyness around girls. Mia explained that he knew Jenny and it was only for a few hours.

During the days before his big date, Mia coached Oliver on how to act and gave him suggestions to keep the conversation going. Most importantly, when he picked her up, he had to tell her how beautiful she looked, open the doors for her, and talk about her interests. She told him to try and stay away from too many details about computers and software and to avoid his passion for Sci-Fi movies. Mia was trying to make him appear less geeky while understanding how difficult that would be.

Oliver was naturally nervous the night of his date with Jenny even though it was more like two friends going out. He did all the right things by picking her up on time, telling her how lovely she looked, and holding doors open for her. Jenny dressed in a tight sweater that did little to hide her large breasts and jeans so she didn't send Oliver any signals that this was more than a one-time date. However, nothing was going to change the fact that she was Oliver's crush.

They went to dinner and a movie which seemed to accomplish the goal of having Oliver feel more comfortable being alone with a female. He started extremely nervous but Jenny helped keep the conversation going during lulls. Even though the date was going better than expected, Jenny found it difficult to consider sleeping with him. She still saw him as Mia's awkward little brother. She considered giving him a pity fuck but at the end of the night, she just couldn't bring herself to do it.

At the end of the date, Oliver walked Jenny to her door and experienced that uncomfortable feeling of not knowing if he should try and kiss her. He just assumed that a kiss was out of the question. Jenny sensed his uncertainty and figured she'd at least kiss him as a reward for his effort. Besides, Oliver was a true gentleman throughout the night which is more than she can say for some of the guys she's dated in the past. He was surprised when Jenny leaned in to give him a full kiss on the lips. While it wasn't as good an ending as getting laid, it served its mission to boost his confidence. It was a step in the right direction.

Jenny sent Mia a text message as soon as she closed the door, telling her friend all about her date. Mia didn't mention her disappointment that her friend didn't take her brother's virginity but she knew that was asking a lot. She was hoping for an easy answer but that wasn't going to happen. It left her with the dilemma of how she was going to get him laid though.

When Oliver got home, he was relieved that the experience was over but admitted that he appreciated his sister's and Jenny's effort to help him. It gave him some level of comfort but he still needed to find a real date. The next day, he asked out a girl from work but she rejected his overture which almost ruined the confidence he gained with Jenny. Mia told him he had to keep trying but he didn't have too many viable options.

In the meantime, Oliver kept checking out his sister in various states of dress and undress. She seemed to make a regular habit of coming home from work and watching TV to unwind before changing out of her work clothes. That allowed Oliver to steal glances at her hose-covered legs and feet and try to sneak peeks up her skirt. He cherished those moments when she was sunning herself by the pool or watching TV with him late at night while she was dressed in various nightwear that he could see through depending upon the lighting situation.

One evening, he went into the laundry room to wash his clothes and found a pair of Mia's pink satin bikini panties between the washer and dryer. He looked around to make sure no one was around and then picked up the panties and stuffed them into his pocket. When he got into the privacy of his room, he pulled them out and brought them up to his nose for a quick sniff. It was the first time he smelled the aroma of a woman's pussy. He felt the softness of the satin and wondered what it would feel like if Mia was wearing them.

The thought of rubbing his cock and balls with Mia's underwear that had been hugging her pussy and ass excited Oliver and he decided to jerk off using them as a prop. He stripped off his clothes, laid on the bed, and began to rub the satin panties over his balls and erection. It felt better than he imagined and closed his eyes thinking of being able to touch his sister's panties but with her in them. He wondered what it would feel like to rub his cock against her ass while she was wearing them or to touch her crotch with the satin fabric the only thing between his hand and her pussy.

Just as he was getting into his fantasy, Mia burst into his room saying, "You locked me out of the bathroom again. I gotta pee real bad."

She took a couple of steps into his room before she noticed her brother was jerking off. A few moments later she noticed that not only was he masturbating but he had a pair of her panties in his hand. Mia was speechless, stopped dead in her tracks, and stared at her brother, not knowing what to say.

Oliver yelled at Mia, "Get out. Darn it, why didn't you knock?"

Mia managed to say, "I'm sorry and quickly left."

Mia was too surprised to ask her brother if those were, indeed, a pair of her panties. The other thing she noticed was that her brother was fairly well-hung. He wasn't enormous but was well-endowed.

When Mia saw Oliver later that night when they were watching TV, she said, "I'm sorry for not knocking before. Please don't be embarrassed, everybody does it, including me."

"Yeah, but how many people get caught?"

Mia tried to make a joke and replied, "Well, at least one that I know of."

That made Oliver smile until she asked, "Were those a pair of my panties you had?"

Oliver turned a deep shade of red and was too embarrassed to say anything which led Mia to say, "That's what I thought."

Mia didn't know what to say or do so she decided not to say anything. She didn't know whether to be creeped out by what her brother was doing with her panties or feel sorry for him. It made her realize that she had to step up her efforts to get Oliver laid but didn't know what to do. Part of her was thinking she should do it herself but quickly dismissed that idea. She kept racking her brain thinking of her limited options.

His twentieth birthday was fast approaching and she felt pressure to do something. Mia thought about hiring a professional escort but she wasn't making that much money that she could pay for their services. The only friend she trusted was Jenny and that didn't work out. The likelihood of her brother asking a girl on a date, her agreeing, and him having sex with her within the next ten days was slim at best.

Oliver's birthday was on a Sunday and their parents were going out of town for the weekend but would be back that afternoon to celebrate with him. Mia ran out of ideas except for the one she hoped would never happen, the idea of helping her brother herself. It could be a one-time thing never ever to happen again. She thought it over, almost obsessively until the day before his birthday. Mia would go back and forth on what to do. She thought about walking in on him and seeing a decent-sized dick. She wasn't dating anyone and was getting hornier by the day. She was probably masturbating as often as her brother. On the other hand, it was an extreme measure to satisfy both of their desires.

Mia made plans with Oliver to go to dinner that Saturday night, the eve of his birthday. She said it would be her treat and they could come home and watch a movie afterward. It's not like Oliver had any other plans so he was fine with his sister's proposal.

On Saturday, Mia still didn't know if she had the courage to go through with her idea. One thing she did know is that she'd need plenty of alcohol if she were to do it. She decided to wear her sexiest little black dress with a halter tie and low-cut V-neck. It hugged her trim body, showing off every curve of her hourglass figure and a touch of cleavage. She wore sheer black pantyhose and black high heels. When she sat down, the dress would ride up her legs to reveal her sexy thighs.

When Oliver saw her, he told his sister, "You look great tonight."

"Thank you, Oliver, you look very handsome yourself."

They decided to take Oliver's car and he opened the door for his sister. As Mia climbed into the passenger side, her dress climbed up her legs and it was impossible to keep her brother from seeing up her dress. He noticed her slender legs and thighs. He was expecting to see the cotton gusset but realized Mia was wearing seamless hose which allowed him to see her pussy lips and trimmed pubic hair. He got the same view opening the door for her when they got to the restaurant.

They had a nice conversation over an Italian dinner. Oliver admired his sister's beauty and lovely body. He could only hope he could find someone as pretty and nice as she. He was disappointed at the end of the dinner seeing they were having such a nice time but Mia said she had a cake for him back at home.

Oliver kept glancing over at Mia's legs as they were driving home. They looked so lovely through her dark pantyhose and he secretly desired to touch them and feel how soft her legs must be. He knew it was only a dream that would never come true. He was disappointed when they got home and Mia got out of the car without his assistance, unknowingly denying him another opportunity to see up her dress.

Once inside the house, Mia kicked off her heels and went into the kitchen to put the candles on her brother's birthday cake. She also bought some beer to help them continue to celebrate. They had all night so they decided to start drinking first and have the cake later. Mia filled a couple of mugs with beer and brought them out to the living room. As she set them down on the coffee table, the top of her dress gaped open allowing Oliver to get a momentary glimpse of her hanging bare breasts. His eyes followed his sister as she sat on the other end of the sofa and turned her torso towards him with her right knee bent on the cushion and her left leg on the floor.

Mia placed her hand on her lap to prevent Oliver from seeing up her dress but she had to remove it to grab her beer mug or place it back onto the coffee table. That is when he would steal glances at her hosed-encased legs and pussy. Mia had no clue that her little brother was checking out her lovely body as they talked. She seemed oblivious to the unintentional flashing of her legs, pussy, and breasts. Mia was more casual around Oliver because she was at home and had no clue how much he lusted for her. Yes, he jerked off with a pair of her panties but she didn't realize it was his dream to fuck her.

As they started their third beer, Mia brought out Oliver's cake and sang Happy Birthday to him. He made a wish and blew out the candles. Mia cut them both a big piece of cake and continued their celebration.

Mia casually asked Oliver, "So what did you wish for?"

"Oh nothing special, besides, if I told you, it wouldn't come true. It's probably not going to come true anyway."

"So why don't you tell me then?"

"No, it's too personal."

Mia kept pleading with Oliver to tell her his wish. He still wouldn't tell her. However, after they were both feeling a little buzzed and they started their fourth beer, Mia asked again.

"Do you promise not to laugh?" He pleaded.

"I promise."

"I wished that I could meet a girl and lose my virginity. I'm not sure that's ever going to happen."

"What would you say if I told you that you can make your wish come true."

"I'd say you're crazy."

"Actually, I do have a crazy idea. What, uh, if I, you know, help you out?"

Oliver looked at Mia with a confused look on his face and asked, "How? Do you know someone?"

"Well, as your birthday present, I was thinking that maybe you and I could, you know."

"No, I don't know. What are you talking about, Mia?"

Mia rolled her eyes out of frustration, so she had to bluntly tell Oliver, "I figured, I'd have sex with you. I think once you do it, you'll have more confidence and nature will take its course."

Oliver looked even more confused, mostly because he couldn't believe what he was hearing, and asked, "You'd really do that for me? This isn't a joke, is it? Because if it is, it isn't funny."

"I'm dead serious, Oliver. It would be a one-time thing. Think of it like a lesson. You could never, ever tell anyone,"

"Who would I tell? Besides, who would ever believe me?'

"Just as long as you understand."

"Shit, it's a deal. When do you, uh, want to give me my lesson?"

"Right now, birthday boy."

Oliver's face lit up as Mia told him to get a couple more beers before they went to his room. Oliver was shaking nervously as he climbed the stairs with Mia. He knew he would eventually lose his virginity but never imagined a scenario like this. Part of him thought he was dreaming and wishing he wouldn't wake up until after he had sex with his sister. Mia's heart was racing too but for different reasons. The adventure she was about to embark upon was certainly wrong by most community standards but she felt a duty to help out a socially struggling sibling. It was an extreme action but these were also extreme circumstances. Her not having sex for several months helped lower her inhibitions but if that was the only thing she needed, there were plenty of other friends who would be more than willing to help her out.

When they got to Oliver's room, he had no idea what to do next. He was even more nervous than before and his hands were trembling as he set down their beers on the nightstand. He also knew it was wrong to have sex with his sister but he also wasn't going to lose this opportunity to finally lose his virginity either. Both of the siblings could hardly believe this was happening and hoped they didn't regret their actions in the morning.

Mia told Oliver, "Try to relax. You have nothing to worry about. I'll help you with everything. Now come here."

Oliver slowly approached Mia and she took his hands and placed them on her back and said, "Normally, you'd start by kissing and making out with a girl but I'm not going to do that. Most guys put their hands on my lower back first and slowly slide their hands down towards my ass. If I don't resist they keep going. Go ahead try it."

Oliver slid his hands down to Mia's lower back. When she didn't resist, he lowered his hands to grab her ass. He began to gently fondle his sister's butt. He had seen her ass in her bikinis and thongs before and wondered how it would feel. He was now cherishing the feel of holding her buttocks in his hands even if it was through her dress.

"Good. Now if she lets you do that, you can let your hand move up to touch her breasts. Go ahead and do it. If she tells you 'no,' you have to respect her and stop."

He then moved his hand up her torso and cupped one breast. He then moved his other hand over Mia's other breasts. Oliver was gripping her tightly so Mia told him to be more gentle. Her pussy was getting damp feeling a male's hands on her chest for the first time in months. Mia has sensitive breasts and enjoyed the feeling of someone playing with them. Oliver found it difficult to believe he was touching Mia's breasts. They felt so soft and full. He couldn't remember if or when his dick had been this hard.

"If a date lets you play with her breasts through her clothes, it's time to see if she will let you take off her top. In this case, you would slowly reach for the tie behind my neck and undo it."

Oliver swallowed hard as he untied the back of Mia's halter dress and slowly peeled it down. It was like he was unwrapping the best birthday present he will ever have as her perky breasts came into view. He didn't have to be told that he could touch them. Mia let out a muffled moan as her brother fondled her breasts and took a nipple into his mouth. He sucked on one for several moments before moving on to the other.

"Most women wished men would spend more time playing with their breasts so don't rush it. The more attention you give them, the hotter the woman will get."

Mia then instructed Oliver to remove the rest of her dress leaving her in only her pantyhose.

"I love seeing you in just your pantyhose. I think it's so sexy."

"Well, go ahead and touch me then. If you find it sexy, so will a woman. We like when a guy gets excited seeing our bodies."

Oliver knelt on one knee and began to run his hands up and down Mia's legs, relishing the feeling of her legs under the nylon pantyhose. He fondled her ass and moved his hands all over her legs but not touching her pussy. He didn't realize he was teasing Mia in the process but she'd explain that later. Mia was getting hotter from a combination of the alcohol, the taboo sexual experience, and being horny, to begin with.