A Crush, A Milf, and a Small Cock

He was a twenty-two year old college student working at his Uncle's company. This business was the second largest employer in the community and took up seventy-five percent of a business strip mall. During the summer he worked full time but while attending college he worked part time. He hated to work on a Saturday but he needed the money and wanted to help out his Uncle. He appreciated the fact his Uncle paid him more than his peers.

Two things made this job difficult. One was the higher standard his Uncle demanded because he was a relative. The second was the consistent teasing he endured. This was because he was known as "Tiny." In the small town he grew up in everyone knew everybody. This nickname was embarrassing and effected his confidence. This lack of confidence caused him to avoid dating. He didn't have his first sexual experience until after graduating high school. This was a disaster. Of course the whole town heard about it and it only added to his torment. He was planning on leaving town once he graduated college. He assumed his only change at having a girlfriend was moving.

Since this incident he was determined to become an excellent lover. The first step was accepting the fact his penis was only four and half inches long when erect. Wishing it was bigger would never help him become a good partner. He focused on the things he could change. He put in the effort to study everything he could about female anatomy and foreplay. In his alone time he worked on his stamina.

A few few days prior to this Saturday morning he found the courage to stand up to some of the guys in the warehouse. Part of his courage came from the fact he was moving away. A bigger factor, he was simply tired of being harassed for being a virgin and having a small cock.

The reason this argument never came to blows was due to the thirty-four year old woman who worked in the shipping and receiving office. She was the best friend of the nephew's older sister (this sister was the second oldest of his three older sisters) and his cousin (his uncle's only daughter and his cousin). She started working at the company right after high school. She was the middle sister of five brothers. She was a combination of tough and feminine; she knew how to take care of herself. The guys on the dock were surprised when she stepped out of the shipping office and told everyone to grow up and get back to work. Out of shock and respect they did so. A huge reason they backed down; they all knew her brothers.

This thirty-four year old woman was a single mother of two boys. She was easily granted a divorce after ten long years. She felt there were five positives about this marriage: her two boys, the house, the mistress who was stupid enough to marry her Ex, and the large settlement she received every month. Everyone who knew what she endured believed she earned every penny. What kept her from dating were: her two boys, living in a small town, and the fear of living through another horrible marriage.

Every summer for the past six years she listened to the guys ridicule him for having a small cock and for being a virgin. Four years prior they added his mishap to this hazing. When she was younger she encouraged this teasing. She wished her younger self would have known better. After the belittling she took while being married she no longer enjoyed anyone being teased; she certainly would never ridicule a guy for the size of his cock. She admired the Nephew's candor and courage to stand up to these guys. She stepped out because they were a lot stronger than he was.

She was managing to keep an ongoing FWB partner a secret. This friend was an older gentleman who lived in the nearest city; this was about a forty-five minute drive from this small town. He was the only man she was sleeping with and only slept with him when her sons were with their Father. Their agreement was, she could sleep with anyone else or end the friendship whenever she wanted. He promised to tell her if he ever wanted a different FWB partner. She correctly believed he would never look for one and only slept with her.

Lately she was indulging in the fantasy of teaching a younger male. She would have never entertained this fantasy without her positive experience with her Older Gentleman. This was the reason she: found an excuse to work on Saturday, canceled her get together with her friend, and dressed the way she did.

This was the first time she was testing the agreement with her Friend. When she called to cancel she used a lame excuse. The friend became angry and asked a list of questions. Because of how guilty she felt she ended up telling him of her plans. She was shocked when this gentleman encouraged her and gave her suggestions. She was unsure of how this made her feel. Even so, she would follow through on her plan.

The Nephew was surprised to see her working on Saturday. He felt she looked attractive in her: gladiator styled black sandals, light colored pair of tight blue jeans, a tight white top, over this she was wearing a pink long sleeved sweater; that ended just below her round medium sized breasts. For the first time at work and for the first time in years she was exposing her belly button. Normally she dressed very conservatively.

When he masturbated he often imagined her wearing the jeans she wore at work or the one piece swimsuit she wore at the company picnic; it was held at a nearby community park with a lake. Like everyone else in town he was happy when she received the divorce. Because she was: a mother, was twelve years older, was a friend of his sister, and worked for his Uncle he felt it would have been tacky to hit on her. Plus, before getting married she participated in the ridicule he received for having a small cock. The other contributing factor was just about every single guy over thirty wanted to date her.

She knew she needed to seduce him. He was to respectful of a guy to just bluntly hit on her. If he ever hit on her, there was no way she would have wanted to seduce him; it would have felt way out of place. Knowing him her whole life she was prepared for him to politely reject her seduction. She chose to seduce him because: she wanted to seduce a younger man, she was tired of him being teased, she understood his history, and as of late was finding him to be cute.

She knew he was a virgin because of his mishap and the talk about his small penis. The way her Ex used his seven and half inch cock turned her off from bigger men. It was a revelation to experience foreplay and a partner who took his time. She expressed to her Best Friend (the older sister) how she preferred foreplay over a large cock. Using this as an opportunity, the sister mentioned how her youngest brother was known to have a small one. The hint was made. Neither would ever discuss this hint any further.

She surprised the Nephew by meeting him in front of the business strip mall. During the conversation he missed many of her hints. He discounted the hints he did pick up; he doubted highly she would ever want to have sex with him.

She finally used a very direct approach and asked, "Is it true you have a small cock?"

If she would have asked him this six months prior he would have blushed and scurried to his car.

It took a lot of bravery on his part to admit, "When erect. It's just just about four and a half inches long."

The way he said it made her giggle.

He turned red and headed toward his car.

She felt horrible.

She quickly stepped in front of him and said, "I asked because I like small cocks."

His look of doubt was immense. He turned and was about to step into his car. How she convinced him was by: grabbing him, turning him around, and flashing her round medium sized breasts. She then grabbed him and led him to her car.

During the car ride he kept waiting for this cruel joke to end. He was sure the guys at the warehouse put her up to this. It was difficult for him to believe this: in shape, attractive, five foot five, long haired blond woman wanted to have sex with him. If she was intending to have sex with him, for whatever miracle this was, he believed she was being nice to him when she said she liked small cocks. The reason he was in the car: was because of the crush he had on her, how she treated him over the last four years or so, and he hoped there was a woman out there who liked smaller cocks. He believed most women were only being nice when they said size didn't matter.

She drove them to a nice country hotel she often passed on her way to the city. She assumed it was far enough away to avoid talk. If there was talk; she hoped he would no longer be teased for being a virgin. She wanted to believe he would keep this one time event to himself.

He was surprised when she pulled into the motel. He was still expecting this to be some cruel joke. He became nervous when she: parked in back of the hotel, led him to a side door, pulled a hotel key out of her purse, stepped through the door, led him to a room she rented, opened the room with the key, told him he should step inside, she shut the door behind them, and set the purse on a long dresser. He allowed himself to believe this was happening when he realized they were the only ones in the room. He focused on everything he studied since his unfortunate mishap and promised himself he would have stamina this time.

She stepped in front of him. In a nice tone she commanded, "I want to see it."

He was shocked by this.

Slightly more demanding but still in a nice tone she said, "Remove your clothes. I want to see your small cock."

It surprised her on what a turn on it was to command him to take off his clothes. This was a tip from her Gentleman friend. The Gentleman believed this would help the inexperienced lover to have more confidence.

She watched him sheepishly remove his clothes.

His penis was at attention.

Her Gentleman Friend advised her this was likely to happen. It always took some time to get her Ex ready and her Gentleman Friend had control over his cock. Because of her Ex she felt she was no longer attractive. This feeling was leaving as she met with her Gentleman Friend. To see this young man at attention even before they did anything was deeply flattering. It had been a long time since she felt this way and it gave her confidence to proceed.

Based upon her Gentleman's advice, she commanded her Inexperienced Lover to stand in front of the mirror. She stood behind him. She reached around and teased it; while teasing it she told him how cute it looked and how she liked how it felt in her hand. He surprised her by telling him he named it, "Tiny Tim." They chuckled at this. What surprised her was how this made her feel more comfortable. Because of this she aggressively yanked it. He quickly shot his cum over her hand and onto the floor. She could tell her Virgin Friend was upset by this. She: stepped around him, grabbed a tissue, gave one to him, commanded him to clean himself off, she watched as she removed the cum from her hand, she commanded him to clean up the floor, and to sit on the bed. She was again surprised on how much it turned her on to command her Virgin Friend. She reassured him by reminding him he was now with a real woman.

Based upon her Gentleman's instruction, she would give her inexperienced lover some time to recover by stepping into the bathroom. This is when she took a shower and changed into lingerie.

She found it interesting when he stood next to the door and talked to her through the door.

She stepped out in a full lingerie outfit; he immediately sprung to life. She set her phone to a playlist she used with her Gentleman Friend. Once the music started she seductively danced out of her lingerie. On his request she allowed him to touch and kiss her body. He was better than she expected. He asked to give her oral. It was pleasurable, but she needed to guide him to her first orgasm of the day. She believed one day he would have an excellent tongue.

After: she turned off the playlist and set out a small meal she brought to the hotel when she rented the room. She found it interesting when he requested her to put her nylons back on. She did so in a teasing manner.

He was delighted she would slip the nylons back on. What boosted his confidence was the fact she never asked him to put on his clothes and she felt comfortable remaining nude while they enjoyed a meal.

Soon after the meal she removed some oils and a plastic sheet from one of the dresser drawers and gave him a full massage with a happy ending. After another round of touching and kissing she showed him three positions for a small cock. He lasted longer than what she expected, but still finished first. She was impressed when he tried to give her an orgasm with his fingers. Her Ex would have just rolled over and fell asleep. To cross the finish line she grabbed his hand and showed him how she liked her button twirled.

The drive back to his car was filled with small talk, memories, and laughter. She encouraged him and hugged him before sending him back to his car. She experienced much better sessions with her Gentleman Friend. She understood her Virgin lover's lack of experience was a factor. What she liked was his willingness to learn and his eagerness to please her; even if she needed to show him how to do so. And yet, this was one of her favorite sexual experiences.

He would never forget the woman he lost his virginity too. She reaffirmed his research. There was more to sex than just intercourse and a guys dick. It was eye opening to know there were women out there who liked small cocks or preferred foreplay over a large one. If a woman gave him a chance he now believed he could make up for his size by using his: tongue, fingers, trying different positions, and by paying attention to her needs. He would never forget the lessons she taught him. An added thrill was loosing his virginity to his first crush.

When she arrived home she: showered, changed, and called her Gentleman Friend. To her surprise he asked how everything went. They ended up talking about the encounter and about general life things. Before they turned off their cell phones they planned on another get together. Her plan was to purchase a new lingerie outfit and give him an awesome blowjob.