Gwen Meets Tall, Dark, and Handsome

Gwen sat at the bar in the hotel restaurant eating bar food. She was lucky, all flights in and out of Chicago were on hold due to the storm but at least she had a hotel room. Gwen did not want to go on this business trip in the first place, but a client wanted a programmer at the table. The hotel along with its restaurant was packed. She was also lucky that she had gotten a seat at the bar, or she would have had to eat standing up.

Tall, dark and handsome sat down next to her. He ordered a burger and a beer with a heavy accent. He turned to her and started a conversation, that started with complaints about the weather and the airlines and their horrible customer service. The conversation turned to how lucky they were, they were not sleeping at the airport and had a decent meal and a warm bed. Gwen finished her drink and she decided against a third. She called the bartender for her check.

Tall, dark and handsome, grabbed the check from the bartender and said., "please, allow me."

Gwen hesitated, and then the man said, "Your expense report or mine, it really doesn't matter, does it?"

Gwen shook his hand and said thank you.

Tall, dark and handsome said, "No, thank you Gwen. I was really lucky tonight to share a few moments with such a lovely and charming young lady."

As she headed to the elevator, Gwen was trying to remember when she had introduced herself to the man, how else would he have known her name. Her stomach began to rumble, and she felt dizzy as the elevator doors slid open. The walls were spinning as she opened the door to her room, and she felt lucky that she made it as she collapsed on the bed. The idea that the man had drugged her crossed her mind which was the last thought she had that night. Gwen awoke in the morning in that same position and the same clothes she had worn the day before. Glancing at the clock, she realized she had to hurry, or she would miss her flight. She almost threw up while showering but was able to keep her stomach down. The flight home was uneventful. A couple of times her stomach felt queasy, but the feeling passed.

Arriving back at her apartment was depressing. Gwen had split with her long-term boyfriend who had been cheating on her. As a programmer working from home, she did not have much left of a social life. Maybe I am not so lucky at all, but at least I can afford this place. Gwen showered, checked her email over a glass of wine and headed to bed.

Sleep came quickly and the dreams came right after. In her dream, Gwen was a stripper. She was in a back room with other girls and one of them was shaving Gwen's pussy. The girl said the men love a bare pussy, especially with that schoolgirl outfit you are wearing. Gwen looked in the mirror, she was wearing the same uniform that she wore when she attended a catholic elementary school. The plaid skirt was a little shorter than she remembered, maybe because she was a lot taller now. There was the same white blouse she had worn all those years and a white bra underneath. When the girl was finished shaving her, she slipped on a G-string and then the same white panties she had worn in elementary school, but these were her current size.

Someone shouted that she was up. Gwen walked on stage and began a sexy dance. Men were sitting around the stage, cheering her. The stage lights made it difficult to see their faces. She thought she saw tall, dark and handsome at one of the tables. The man stood out because he was very well dressed. The other men were clamoring to see under her skirt, to see her panties she thought. Gwen worked the edges of the stage. She would twirl knowing the skirt would ride up or bend over. As the song went on, she started pulling the skirt higher and higher, showing the men her panty covered pussy.

A second song started. Gwen continued to dance and began rubbing her breast before removing the jacket, tossing it on the floor. The buttons on her blouse were next. And when they were undone, she held the blouse close until she pulled it off adding it to the jacket. Never before had she been in front of more than one man in her bra, now there were dozens. She continued to rub her breast as she danced, eventually popping out her nipples. With her nipples exposed, she wet her fingers and began to rub them. Gwen's nipples were already hard, but the men seemed to love watching her play with them. The bra ended up with the blouse and jacket as the second song ended.

Gwen continued to dance into a third song and continued to play with her naked breast. She knew it was time for the skirt to join her other clothes. She was working the edge of the stage, unbuttoning the buttons along the side and then let the skirt drop to the floor. She continued to play with her nipples as she danced and allowing her other hand to drift inside her panties. She worked her way back to wear she thought she saw him. He would want to see this she thought. She turned her back to the audience, bent over at the waist, and slide her panties to the floor. Gwen spun around and squatted on the floor, pulled her legs apart. Only the thin material of the G-string was between the men and her pussy.

Gwen stood back up and started dancing around the edge of the stage. The men were all reaching up, dying to slip a dollar bill into her G-string. She knew they were not supposed to touch her, but they did. She wanted them too. As they slipped bills into the G-string, they would run their hands up the back of her thighs or feel her ass. She wanted tall, dark and handsome to feel her ass, to run his finger over her rosebud and slide it in. Instead, he sat at the back of the room, smiling at her.

Gwen awoke with two fingers deep in her pussy and a finger from her other hand buried in her ass. The tidal wave of her orgasm overcame her, and she fell back to sleep.

The dream came flashing back to her when she woke up. Gwen could not recall ever experiencing a more realistic dream. She was no stranger to masturbating but it was something she frequently did in the shower, not in the middle of the night. Gwen's ex would like to slide a finger or two into her ass, and she enjoyed that, but she would never do that to herself.

Mindlessly, Gwen headed to the shower. As she started to wash herself, she realized that her breasts were tender and there were some minor black and blue marks on her nipples, as if someone was pinching them. Scenes from her dream came back to her, where she was pinching and pulling on her nipples as she leaned over the audience. In the shower, Gwen came again.

Gwen stepped out if the shower and wrapped a towel around herself. She started to brush her hair as the fog on the mirror cleared. Gwen checked the damage she did to her breast again, letting the towel drop to the floor. She turned to head into her room to get dressed for work and noticed that her pussy was now bare. It reminded her of a little girl and thought that the men who liked bare pussies must be perverts. It did not bother Gwen that she had no recollection of actually shaving her pussy and she had no intention of doing so.

At various times in her life, Gwen had dressed provocatively, and she had more than one boyfriend who encouraged her to flash people, but never considered actually stripping. What if her mother found out. She never understood her mother's warnings that if she did not sit right, a boy could see her panties. So what, she would think, what were they going to do? Rape her because they saw her panties. She started to understand as she got older, and she noticed men checking her out. And as she did, her skirts got shorter, a form of rebellion against her mother. By the time she was 18, she loved to tease her boyfriends by walking around in front of them in her bra and panties. The bras went away for a while when she was in college.

Her fascination with exhibitionism started in her senior year of high school when she found the idea of giving strangers a peak excited her. It also excited her boyfriend at the time who was always trying to get her to flash someone. On one occasion at school, she was on stage after a play rehearsal and the old black janitor was sweeping the orchestra pit. Deliberately, she bent over to pick up her script, exposing her panty covered bottom to the janitor. She looked back at him while she was bent over, and he was smiling at her. They stared at each other for a moment and then Gwen realized he was rubbing his crotch. She smiled back and walked away thinking about the large bulge in his pants.

Many times, she masturbated to the idea that the old janitor would be jerking off, thinking about her panty covered ass. In her dreams, he would tell her to do other things like masturbate for him or expose herself to his friends.

They played that game several times the rest of the year. She started buying thongs so she could show him her bare ass. When they happened to be alone, he would rave a finger in the air, signaling that he wanted her to face the other way and bend over. Sometimes he would whisper "the front" and she would pull up the front of her dress so that he could see the front of her panties. Near the last week of school, she found a note in her locker that said she should leave her panties home. Gwen spent the week going naked under her skirt, but they never got to be alone again.

When she was cleaning out her locker at the end of the school year, Gwen found a note that read: "Someday I will have you and not in your dreams."

Her flashback to the janitor ended and she needed to get dressed for work which was quite easy for Gwen, a t-shirt and some panties. She would wear a bra under the t-shirt if she had a video conference. She logged onto her computer and began working on the changes the Chicago client had requested. The work was overly simplistic, but she realized she was lucky that she had a programming job at all.

The day after returning from her trip, Gwen received a registered letter in the afternoon from a law firm requesting she call them. The law firm put her on hold and then a man was on the line. The lawyer explained that her aunt had passed a week ago and left her a sizeable fortune, not enough to retire on but enough to change her lifestyle. The aunt had been sick for a while and had liquidated the rest of her belongings before she passed. Gwen had to go in and sign some paperwork. There was also a box of personal items her aunt wanted her to have. The lawyer said she was very lucky.

Gwen had not seen her aunt in ages, there was a falling-out between the aunt and the rest of the family before she was born. The details were not discussed but from what she heard, the aunt had married a man of color who had vast real-estate holdings in the south, including some former plantations. Gwen found the obituary online. It described her aunt as one of the wealthiest landowners in that part of the state. The aunt was predeceased by her husband and Gwen's mother. Gwen was listed as a survivor along with her aunt's three sons or her three cousins.

Gwen called in sick at work the next day so she could visit the law office. The money was wired to her personal account, and she left with a box from her aunt. Once she got home, she opened the box and found a note from her aunt. Most of the note was her aunt's regrets over the falling out she had with Gwen's mother. Gwen's mother had passed a year earlier but the two sisters never reconciled. The note also described a necklace the aunt was giving her, that always brought the aunt good luck. Gwen found an old-fashioned cameo in the box. The profile of the woman could easily have been her aunt or Gwen.

Gwen put on the necklace, and she swooned, easing herself onto the couch. Her eyes closed and she found herself in the jungle with her hands tied over her head. There were black men, dressed as natives who were gathered around her. One of the men came up to her and he began to cut off her clothes. Once she was naked, the men began to run their hands all over body, squeezing and pinching her breasts. They pulled her legs apart and began to poke and prod her pussy and ass. A group of women came up, pushed the men away and began to wash her. A white woman came up, she was well pregnant, held a nursing baby to her breast and a toddler held her hand. The woman looked like the same woman who shaved her pussy in her first dream. She also wore a similar cameo around her neck.

"You don't know how happy I am to see you," she said. "This tribe needs another breeder. I've been here for four years, and my fifth child is on the way. These women will cleanse you and then you'll be presented to the chief. After you have his child, you'll be passed onto someone else. You are very lucky because you will be treated like a goddess here."

A tall naked native came up alongside her. His cock was huge, hanging almost to his knees.

The pregnant woman grabbed the man's cock and began to stroke it.

She said, "I'm his until this baby is born. It isn't that bad once you get use to the perpetual morning sickness. It also takes some time to get use to a cock this size but that is well worth the effort."

The women of the tribe began rubbing some kind of oil on her. The made sure her breasts were well oiled, Gwen could feel her nipples becoming aroused. Other hands began working the oil into her pussy and ass. She could feel her lips and clit swelling.

The crowd around her parted and a man she assumed was the chief started walking towards her. His cock was dangling around his knees. As he came closer, she realized it was tall, dark, and handsome. Someone started rubbing her clit and she came. Her orgasm woke her up and she found herself laying on the couch naked, with her hairbrush deep inside her. She laid on her couch, licking her hairbrush and pushing it back in her pussy. She was thinking about the chief's cock inside her, fucking her cunt, stretching it out, how full she would feel, and she came again.

In the afternoon, Gwen logged onto her computer to check her email and try to plan her future. As she was going to shut down her computer, she decided to search on "strippers." Thousands of websites were in the search results. One contained a picture of a girl in a school uniform. Gwen clicked on the link. A woman with huge tits was dancing on a stage. The skirt was so short, her ass cheeks were visible. The woman was much more graphic than Gwen remembered being. The stripper was kneeling on the floor, pretending to be fucking and invisible man. There were no panties or G-string under the skirt when it hit the floor. The stripper sat on the edge of the stage and pulled her legs apart, and then she spread her pussy lips. One, then two and then three of her fingers began to be shoved inside her. The stripper would pull the fingers out and lick them clean before pushing them back in. The stripper appeared to have an orgasm and then a single person could be heard clapping as the screen went to black. Gwen thought about licking her fingers the next time she stripped. She had never been a fan of tasting her own pussy, thinking it was too close to being a lesbian, but she had enjoyed licking her juices off the hairbrush.

Gwen continued to experience stripping dreams over the next several nights. Her outfits were usually different, one time a cheerleader, another as a nurse. Sometimes she would remember more details than others. Always, she woke up finger fucking her ass and pussy. In one dream, she was kneeling at the edge of the stage in her G-string, and she was slapping her pussy. The cameo was glowing between her naked breasts. The men were counting every slap and throwing money at her. Tall, dark, and handsome was standing a few feet away from the stage, smiling at her. At slap 24, she orgasmed onstage to the cheers of the men, another wave of dollar bills fell onto the stage. Gwen's real orgasm woke her up, but she rolled over and went back to sleep.

Masturbation was not unusual for Gwen, maybe once a week. It also depended on how often she slept with someone. Her ex had been rather good at keeping her satisfied. She had been home from Chicago for five nights now and had masturbated every night and at least once during the day. Her self-induced orgasms were on par with those brought on by her ex, maybe even better. Never had she masturbated more than once a day. Now, she was masturbating three times every day, and sometimes more.

Gwen was meeting some friends for dinner that night. Looking through her closet for something to wear, Gwen found a schoolgirl outfit similar to the one she stripped out of in her dream. There was also a cheerleader's uniform.

The restaurant was crowded and loud. Twice Gwen thought she saw tall, dark, and handsome sitting at the bar. One time she even walked over but there was no one like him anywhere. Gwen thought how dark he appeared in her dreams, much darker than when she met him in Chicago. Her girlfriends were laughing and drinking too much, and that always led them to talk about sex. Some were getting it good; some were relying on their battery-operated boyfriends.

They turned to Gwen who said, "so where do I get one of these battery-operated boyfriends?"

Her friends started laughing and they all picked up their phones, sending her links to websites that sold sex toys.

Hungover did not quite describe Gwen's health the next morning. Her head swirled and she barely made it to the bathroom before emptying the contents of her stomach. She cursed the tequila shots they did, compliments of some male admirers. She realized it was the first time since Chicago that she did not have the stripping dream.

She made some coffee and picked up her phone. There were a bunch of messages from her friends, some were pictures of the group, and then she came across the links to the sex shops and toy stores. After some errands and lunch, Gwen found herself in front of her computer searching through the toy stores. She never realized how many different toys there were for woman. There were fake dicks, some incredibly large and usually black. There were battery operated ones, some vibrated and some twirled inside. Some even squirted warm water to simulate a man's orgasm. There were some for pushing up your ass. Gwen wondered what it would be like to have one up her ass and another one in her pussy.

While shopping for a toy, she came across a link for strippers. Most of these girls were young, stripping out of regular clothes while their boyfriends filmed them. They usually ended up on the floor or bed, fucking themselves with a toy. Gwen started fingering herself watching a girl with dildo that she had stuck to a wall mirror. First, she pretended to suck it, then she backed her pussy up to it and slid it inside her. Gwen watched as the starlette kept smashing her ass against the mirror. Gwen and the starlette orgasmed at the same time although Glen believed the starlette was probably more satisfied.

Gwen continued to sit at her desk, licking her pussy juice off her fingers, thinking back to the days she would have found that repulsive. She looked down at her bare pussy, she wondered why and when did she shave it and why did she continue to keep it smooth? Gwen though of tall, dark, and handsome. How did he know her name and why was she having the most erotic dreams since she met him? While lost in her thoughts, she ordered several toys.

She sucked down a bottle of wine that night and again did not dream.

She had a new dream on Sunday night. She was in a short black dress that barely covered her ass. The front of the dress barely covered her tits. They were in a VIP room at some bar drinking champagne. The woman she was with, the same woman who shaved her pussy at the strip joint was telling her she was a "party girl." The woman saw the confused look across Gwen's face. Most of these guys are big time sports players. We are here to keep them happy. That means if they get roaming hands, you smile and let them enjoy themselves. There were several other girls in similar dresses.