Debbie Explores

Debbie and Tamika are introduced in: Shanice and the Questionnaire. They are in the story: Harmony: Blessed But Not Perfect, and both are in this story: Debbie Explores. Debbie is the main character of this story: Debbie Explores.

Harmony and Shawn are introduced and are the main characters in the story: Harmony: Blessed But Not Perfect. Harmony is in this story: Debbie Explores.

Shanice and Ryan are introduced and are the main characters in the story: Shanice and the Questionnaire. Shanice is in the story: Harmony: Blessed But Not Perfect, and is mentioned in this story Debbie Explores.

Note: it isn't necessary to read these stories to understand this one.

If the paragraphs seemed messed up its because of the RULES OF THIS SITE

**Introduction**

Debbie posted her first classified ad when she was a thirty-one year's old. Debbie was a light skinned mixed raced woman. At the time she was: five foot eight, her hair was dyed black, she had a long oblong shaped face, a long nose and a high forehead. The bridge of her nose was skinny while the bottom was wide and hooked. It was difficult to miss her intense dark eyes and dark eyebrows.

When she smiled her high cheekbones became visible. She had a skinny upper lip with a luscious lower lip. Her C-Cupped breasts were on the outside of her chest. She was frustrated her hips and backside were growing despite working out and eating well. She had strong legs and small girl muscles on her arms.

Her dark eyes never lied. When she was angry they could bring the toughest of men into submission. When she was frustrated they showed how irritated she was. When she cared about someone they shined the feelings she felt toward the person. No matter what she was feeling her eyes showed wisdom and life experience.

She was an adaptable person. This being stated she would never sell out. What she said is what she meant. She abhorred: lying, nonsense, immaturity, and arrogance. She admired: confidence, truthfulness, wisdom, and patience. She disliked: clutter, believed in being organized, and hated to be caught off guard. She was able to stand up for herself while maintaining a feminine quality.

**Heartbreak**

She was twenty-six years old when she helped Harmony move in with her husband Shawn. Four months later Isiah stepped into the store she managed. She immediately focused on this tall handsome black man. He was twenty-nine, six foot four, muscular, and was a gentleman. She made sure she was the one who fitted him for his police uniform. They hit it off immediately. He found himself telling her his life story.

He moved from Chicago believing it would be better for his two daughters to live in this Northern Midwestern Metropolitan City. He purchased a duplex. He moved his Mother into the bottom floor. Isiah and his two daughters lived on the top floor. Debbie was the first woman he asked out since his divorce and being awarded custody of his two girls. He was the first customer she ever accepted a date from.

Nine months later they were married. For two and a half years she was a wife and step mother. It was obvious to everyone Isiah and Debbie were destined to be together forever. She loved her Step-Daughters as if they were her own and they responded in kind.

Her heart was torn apart when Isiah's supervisor and police partner stepped into the store. They informed Debbie that her Husband had been killed in the line of duty.

A year later she was crushed when she lost custody of her two Step-Daughters. The memory of them clinging to her for dear life was forever etched in her mind. Debbie tried to be brave and encourage them. This ended when the mother grabbed them, called Debbie spiteful names, and dragged these two girls out of court.

Debbie yelled at the judge and was almost arrested. Tamika, Harmony, Debbie's Mother, and Debbie's Mother-in-law managed to lead Debbie out of the courtroom.

Once in the hallway Debbie fell into a bench and wept bitterly. It was Harmony and her Mother-in-law who spoke the words Debbie needed to stand up. Isiah's Mother-in-law and herself hugged for a long time. This gave Debbie the strength to walk out of the courthouse.

Two weeks later Isiah's family and Debbie helped Debbie's Mother-in-law pack her things. She was moving back to Chicago. Just before Isiah's Mother-in-law was to leave they hugged and wept for a long time. Isiah's family invited her to Chicago. They had a place for her stay. Debbie politely refused. Debbie hugged each family member and said her goodbye.

Three months later a similar scene took place. The jury ruled in favor of the criminal who shot Isiah. The trial was a political rally. Debbie despised the media and the people cheering for the criminal. Isiah's police partner and a woman police officer led: Debbie, her Mother-in-law, and those people who supported them out of a back entrance of the courthouse. Once in the parking garage Isiah's Mother-in-law and herself hugged for a long time. Debbie hugged her Brother-in-Law and Sister-in-law.

This was the day she decided she would move back to the small Wisconsin community she grew up in.

What kept Debbie going was: her friend Harmony (who was the owner of the store Debbie managed), her Sister Tamika, her Aunt Shanice, her Uncle Ryan, their two children, her Mother, phone conversations with her Mother-in-law, and her friends at church.

Her job gave her purpose.

She was determined to give the best customer service to every officer and fire person who stepped into the store. Both a blessing and a curse was serving everyone who knew what happened to her deceased husband. This was the motivation she needed to open her own uniform store once she moved back to Wisconsin.

After the murder trial she found sexual exploration something to look forward too. The least thing she wanted was for anyone she knew, or anyone associated with the store, to know she was exploring sexually.

**Sex Before Isiah, Sex with Isiah, and Her Desires After**

Before she married Isiah she had three long term boyfriends. She made love to two of them. This love making lacked foreplay and neither guy performed oral. She never missed receiving oral because she embraced the full feeling she received from their large cocks.

She felt conflicted about oral sex. The one time she performed oral it was a horrible experience. She wondered if this was because of his large cock or her lack of experience. Either way; she was reluctant to ever try it again. The idea of receiving oral sex made her feel hypocritical. She understood why a guy would refuse to give women oral. In general; she wondered why anyone would want to give anyone oral sex.

Based upon her past experience she felt Isiah was a wonderful partner. She adored Isiah's large cock and his willingness to try a variety of positions. She felt it was fulfilling because they performed enough foreplay to get them ready for penetration. Only twice did they manually give one another orgasms. She was grateful Isiah never requested oral sex.

After Isiah's death her sexual drive increased. Fantasies and desires she never contemplated were now on the forefront of her mind. She never considered finding a partner because she wanted to be a great Step-Mother. She would only date a man who would accept all three of them and would be a good father to them. After they were taken from her she continued to restrain herself because she was determined to wait until she was in love with a man before having sex again.

The day after Isiah's murder trial she drove around the city resisting the temptation to step into a club or bar and have a guy pick her up. Everyday for a month she fought off this temptation. What stopped her was how many people she knew from church and from her job.

Late night TV commercials presented an alternative to bars and clubs. The first commercial was for a dating phone line and the other was for a "meetup" website. Three months after the court case and a month before Christmas she posted multiple ads seeking "friends". She waited to use these services until: she went on birth control, researched every dating sight, and sampled the phone line.

She avoided any app where you slid left because she didn't want anyone she knew to know she was looking for "friends." Her phone ad was straight forward but had class. She posted ads on two different mainstream dating websites without a picture. These ads walked the tight rope of erotic intent while letting the world know she was being selective.

Her most risque ad was posted on a classified hookup sight. In this classified ad she felt free to mention a few of her pent up desires and posted four pictures of herself. She managed to avoid showing her face in any of these ads. In the first two pictures she was showcasing a three set lingerie outfit with garters and nylons. This outfit was far more risque than the lingerie outfits she wore for Isiah.

The third picture was a full frontal nude from the neck down to her feet. The fourth was a cropped picture of her C-Cup breasts. She felt a mix of emotions about these photo's. The first was embarrassment, the other was fear, and the third was arousal.

She masturbated after posting the ad. She started the masturbation session with a fantasy of riding a big cocked attractive man with stamina. Her session ended with a memory of her deceased husband. After; she curled up on her bed and cried.

**Three Phases**

The first phase was handling the overwhelming responses to her ads. She would first skim the messages and remove what she felt were horrible responses. The responses she liked would be copied (phone messages would be transcribed) and placed into folders in her laptop.

These folders were titled: Unsure, Somewhat Like, Really Like, and Women. After three months: she stopped using the phone line, she blocked her ads from being viewed, but kept her memberships. She no longer wanted anyone to respond to her ads but she wanted the ability to respond to the men and women who sent her responses.

The second phase was the weeding out process. Her steps to this process were as follows: having an email conversation, conversations over the phone, exchange of pictures, and meeting someone at a public place. Meeting someone in a public setting didn't mean she was committed to having sex with the person. There were seven people (five men and two women) who never made it to the bedroom because they assumed meeting at a public place meant they were having sex.

The speed of these phases depended on the person she was communicating with. She never intended to have a one night stand, she would never lead anyone on, and to the best of her ability she avoided anyone who was married or in a committed relationship.

Debbie ended communication with anyone who: was married, engaged, participated in drunkenness, enjoyed recreational drug use, the guy wanted unprotected sex, or the person was disrespectful. This phase stopped her from meeting: three dozen customers, a friend of Isiah, a few friends of relatives, a female second cousin (Debbie never outed her), two dozen married men, and a half dozen married woman.

She dealt with two difficult situations. The first situation involved a man who was married to a friend of hers from church. Her friend was a very faithful wife who believed her husband was being faithful. Debbie exposed this husbands cheating without letting anyone know she was involved. The second situation was with a woman named Terra who was a part time seamstress at the store she managed.

Debbie would have never guessed this dark skinned feminine woman was a lesbian. While exchanging emails Debbie found out Terra had been in a relationship with a woman for five years, recently broke up, and wanted to fulfill the fantasy of "teaching" an inexperienced woman. Debbie was grateful she figured out who Terra was before Debbie sent a picture of herself. Because of mutual respect neither one asked the other about the ad or emails. Terra came out at the yearly Christmas party by introducing everyone to her new girlfriend.

The final phase was having sex. She had to feel: a personnel connection, she needed to believe the other person would be discreet, she needed to trust the person, and she needed to feel safe.

**Her First Friend Terrance**

Two weeks after New Years she met up with a forty-one year old professional black man named Terrance. He sent her a picture of himself in a suit and bow tie. What impressed her was his five paragraph reply. The first thing he mentioned was how attractive she was in nylons and how much he liked her outfit. He wanted her to wear a sexy outfit every time they met. He offered to pay for these outfits if she was willing to wear them everything they met one another.

His lingerie fetish gave her pause.

She reminded herself she posted these ads to experiment. She was willing to deal with the consequences of what a "friend" thought of her willingness to experiment. What she didn't want to deal with was the possible negativity from a long term partner. Other consequences she was trying to avoid were: pregnancy, being hurt emotionally, a sexually transmitted disease, and someone she cared about finding out she was experimenting with multiple partners.

She felt living in a metropolitan area gave her the best opportunity to experiment without loosing her reputation. The anger and hurt she felt overruled her: guilt, morals, and sense of responsibility. After suppressing certain emotions and embracing others; she continued to read Terrance's response.

Debbie admired his maturity. She felt the majority of the responses she received were childish, rude, or it was obvious the person didn't read her ad. She felt it was childish to send a one sentence response or a dick picture. She liked some of the pictures, even masturbated to a few, but she would never respond to someone who sent a dick picture in their first response.

The reason Terrance wanted a friend was because of his career. As a Vice President he didn't have time for a relationship but wanted his sexual needs fulfilled. His favorite place to travel was Australia, his favorite color was blue, and he enjoyed a wide range of music; she was impressed with the long list of artists he enjoyed.

They exchanged numerous emails and had numerous conversations over the phone. She agreed to wear sexy outfits if he would give her head. He claimed to be an expert at giving oral and volunteered to purchase the outfits she was to wear. His plan was to purchase two to five outfits and she'd pick the one she liked. She felt this was to expensive. He insisted it was easier if she just kept every outfit instead of returning any. She wouldn't argue the point.

She was disappointed he didn't want a friendship outside of the bedroom. His logic was, if he had the time for a friendship outside of the bedroom, he would have time for a relationship. She agreed to work with his schedule and agreed to a maximum of four hours. From this time on she called their times together; "visits".

They met at a restaurant attached to a thriving mall. He was right on time. He was six-one, slender, wore a very expensive pin stripped suit, a bow tie, and wore a pair of glasses. He was very polite when he introduced himself. He was business like during the meal and refused to talk about sex while in public. He insisted on paying and was polite to the restaurant staff. He handed Debbie a business card and wrote down three days and times when they could meet. He promised he'd meet anywhere she felt comfortable.

They talked for a short while before he left exactly at the time he said he would. Later in the day she suggested a hotel not to far from where they ate. He picked out the day and promised to pay for the hotel. She agreed to both the hotel and the day.

She arrived at the four star hotel early. This hotel was in a southern suburb near a strip mall and bowling alley. She was able to drive to the hotel because the roads were salted and the plows were out. It wasn't the easiest of drives but it was nothing she wasn't used too. This trip was a reminder on why she was planning on buying a four wheel drive truck.

She parked as close to the entrance as possible. She: buttoned and tied her black fashionable trench coat, checked her makeup with the rear view mirror, with the same mirror adjusted her gray winter brimmed hat, pulled out the key fob from the ignition, set it into her purse, slipped on a pair of black leather gloves, grabbed a black and white checkered tote handbag, grabbed her purse, took a breath, stepped outside, shut the drivers side door, lifted the windshield wipers off of the windows of her 2018 red Ford Fusion, turned, and carefully approached the hotel.

She was wearing black fashionable women's hiking style boots with fur on the inside. The boots matched her white and black checkered high waisted pants. Under her coat was a black long sleeved satin shirt (If she was spending any time outside she would have picked warmth over fashion). She added a pair of black rope style hoop earrings and a black layered choker necklace set with a black retro coin pendant.

As soon as she entered the hotel the memory of Isaiah and herself entering this lobby hit her. They participated in a bowling tournament across the street with her Uncle Ryan and her Aunt Shanice. Tamika (her sister) was watching the two girls for the day and night.

Remembering the joy of this day made her step to the side of the lobby and sob. Her impulse was to cancel her visit with Terrance. She pictured herself spending the rest of the day trying to convince herself to unpack the boxes in her second bedroom. Wanting to open them and never doing so only added to her feelings. She blocked out all of her emotions and gained her composure. She brushed her tears away and stepped up to the counter.

She was surprised to learn he'd paid for a suite; she would've been content with a regular room. She stepped onto the elevator. As it went up the eight floors it stopped five times. Each time it stopped she worried she'd meet someone she knew. She was grateful when the elevator stopped on the floor of the suite. She quickly headed to this suite. She used the key and stepped into the room.

It: was spacious, had nice furniture, a large TV, and it appeared very clean. She inspected the suit for bedbugs. Once she was sure there wasn't any she removed her trench coat and hat. She hung these items in a small closet. She stepped into the bathroom carrying her purse and tote bag. She touched up her makeup and fixed her hair. She turned on the TV and laid on the bed.

This was the first time she was having sex without being in love. This caused her to be nervous. She suppressed the guilt she was feeling.

She asked herself out loud to no one, "What did it matter?"

He stepped into the hotel room exactly at the time he said. He was wearing: a very expensive button trench coat, an expensive hat, based upon the pants he was wearing she believed he was wearing an expensive suit. He was carrying a laptop case and a plastic bag.

When he set down his laptop case and bag she spotted the advertising on the side of the plastic bag. The boutique advertised on this bag catered to women and couples. Debbie purchased many of her sex toys from this store.

He simply said, "Hello."

In her Wisconsin accent answered, "Hi."

As he took off his coat he stated, "Would you mind standing up."

She did.

He hung his coat on a hanger. He was wearing a very expensive dark blue suit with a vest, a white shirt, and a white and blue striped tie.

He stated, "You look gorgeous."

"Thank-you."

He hung the coat on the opposite side of where Debbie hung her clothes.

He reached down and picked up the plastic bag, "Would you mind changing into one of these outfits?"