Essentially Lisa - Cover

Essentially Lisa

Copyright© 2001 by The Midnight Lurker

Chapter 5: Quite A Unique Car Ride

Erotica Sex Story: Chapter 5: Quite A Unique Car Ride - Read along as one woman goes through a series of blistering sexual encounters with a variety of different people, from her older boss to her bi-sexual girlfriend, to her group of boyfriends and a few strangers as well.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Consensual   BiSexual   DomSub   MaleDom   Spanking   Light Bond   Gang Bang   Group Sex   Orgy   Interracial   Black Male   White Female   Oral Sex   Anal Sex   Masturbation   Sex Toys   Exhibitionism   Voyeurism  

It had been almost a week since Lisa and her boss, the 54-year-old Mr. Collins, had their first (and thus far, only) sexual encounter with one another. Because she was just a part-time employee, Lisa mostly only worked on the weekends. She had not seen, or even heard from, Mr. Collins since that fateful evening last Sunday.

Lisa did find it interesting, however, that Mr. Collins had put her on the work schedule for 10:00am to 6:00pm this Saturday - which was today. The art gallery always closed at 5:00pm sharp on weekend afternoons. Lisa was well aware what her boss would want her to do during the final hour of her shift. And none of it, she knew, was work-related.

Lisa remembered the instructions that Mr. Collins gave her, too. She was to come to work from now on with a "playful and naughty" look about her. Translated, Lisa knew, she was supposed to dress like a slut. She wondered how long it would take before her old boss put his hands on her again today. Could he possibly out hold until 5:00pm? More likely, she thought, they would be heating each other up much earlier in the afternoon.

Lisa's wardrobe for work on this particular day fit her boss' demand. The tall, statuesque blonde had decked herself out in a black denim miniskirt which displayed her long, luscious legs in a very enticing manner. Her legs were accentuated even more by a pair of spiked high-heels which made her a couple inches taller than her natural 5-foot-9. Just about everyone agreed that Lisa had sleek, sexy legs.

In addition, the nymphomaniac was wearing a sleeveless top made of cotton. Not only was it very thin, but the top was also an extremely tight fit. That was a good thing, of course, because Lisa had big, firm breasts. The V-neck design of her blouse also allowed for a mouth-watering view of her vast, deepened cleavage.

Lastly, it was rather obvious just from one glance that the buxom blonde was not wearing a bra underneath her little top, either. Her nipples jutted outward against the fabric, giving the impression that they begged to be sucked upon. Soon, she hoped, that exact thing would happen to them.


Upon arriving at work in her outfit, Lisa immediately began to receive looks and stares from the customers who visited the gallery. Lisa always received her fair share of eyes, simply because she was a beautiful woman. But it was more so on this day, because of the outfit she wore. Several men openly flirted with her, and some almost went as far to ask her out on a date. Unfortunately, none did.

Before her encounter with Mr. Collins last Sunday, Lisa had always went to work with a very professional and classy appearance. The beautiful blonde always tried to separate her professional life from her personal life - until now. She truly enjoyed dressing like a trashy slut a whole lot more. Lisa liked her boss' request that she come to work from now with a "flirty and naughty" look.

As the first few hours of her shift went by, Lisa did not see her boss. The only other co-worker she saw in the gallery was Tiffany, who was also a salesperson. Tiffany, who was quite beautiful herself, seemed to look at Lisa on more than one occasion with a curious expression upon her face. Lisa figured that Tiffany was kind of curious as to why she was dressed like a slut on this day, but didn't have the raw courage to step forward and ask.

Lisa, having not seen Mr. Collins all day, wondered to herself if he was even here today. If he wasn't, it would be a definite let-down for her. She expected to come to work today, and get fucked. Nothing less would satisfy her.

However, Lisa's fears would diminish soon thereafter. When a little lull in business came, Tiffany decided to take her 15 minute break, leaving Lisa alone in the showroom. Not for long, though - as she soon felt a strong hand squeeze and pinch her ass from behind. Lisa spun around and giggled like a schoolgirl upon seeing her boss, Mr. Collins.

The 54-year-old man explained that he had been in an important meeting with an art dealer earlier this morning. After the dealer left, Mr. Collins said, he simply stayed in his office and kept his eye on Lisa with the help of the video surveillance system. Mr. Collins also admitted to whacking off as he watched the little vixen prance around the gallery in her little miniskirt and ultra-tight blouse.

The man said that Tiffany's shift ended at 4:00pm and after she left, he hoped to close the gallery a bit early. This would give he and Lisa some extra time together, most likely in his office. Mr. Collins had an evil look upon his face when he claimed he fully intended on fucking her over the desktop again. Lisa, of course, could barely wait...

Their conversation ended abruptly, however, when a customer strolled into the gallery. Lisa went to attend to the lady while Collins scampered back to his office. He planned to do some more masturbating with his video system.


As late afternoon came, Lisa was becoming more and more anxious. As was Mr. Collins, obviously, who appeared from his office and offered to let Tiffany leave a half-hour early, at 3:30pm. Tiffany said that she needed the money, as most college students did, that extra half-hour would bring her. She rather stay for the entire duration of her shift.

Eager to sink his cock into Lisa, Mr. Collins told Tiffany that she could go home early, yet he would still pay her for a full eight hours. That offer simply could not be refused.

Once Tiffany got into her car and drove off, Collins locked the door to the gallery and instructed Lisa to go straight to his office. She obeyed, of course, and then had to strip down to nothing and offer her lecherous boss a very long and thorough blowjob. After the man came all over her face and hair, coating her with his sperm, Lisa was propped up on the desk and received some oral worship on her pussy. Collins made the nymphomaniac scream and shudder with pleasure, just before he brought her to a fierce, heart-pounding orgasm.

After a lull in the activities, the lust-couple heated up again as Collins fucked Lisa's pussy from behind, as she was leaning across the desk. It ended when both individuals experienced mutual orgasms, each screaming out their desire.

After both of them recovered, Collins asked Lisa to give him some specifics about her lifestyle. He said he was very interested in hearing about the gang-bangs she had taken part in. Lisa went on to tell her boss all about her three boyfriends, and the many acquaintances and strangers she had sex with over the past year. Her favorite encounters, she told him, was those gang-bangs where there were a lot of men waiting to stick their cocks into her various orifices.

Collins' interest level seemed to reach its zenith when Lisa told him about her live-in lover, Jenn. Never in his wildest dreams did the man believe that Lisa was bi-sexual. But the mere idea sent erotic shivers throughout his body.

Collins then went onto tell Lisa that he and his wife were "swingers". He also told her that his wife, Kim, was bi-sexual too. Collins suggested that Lisa should get together with he and his wife for some fun.

The buxom blonde was a bit skeptical at first. She liked the idea of being with older men, but never really thought about being with an older woman. Collins assured her that his wife, Kim, was very attractive. She was 46, he said, but "looked to be at least 10 years younger". Collins also said that Kim was very much in shape, and really knew how to treat a woman well. After some more coaxing, Lisa finally agreed to meet Collins and his wife for some fun.

As could be expected, the old boss nearly went out of his mind with lust. The possibilities were limitless. He told Lisa to go home now, and get ready. He and his wife would pick her up, at her apartment, later tonight at 7:30pm. They would take her back to their place, and the trio would spend the evening together.

After Lisa put her clothes back on, she gave Collins a long kiss and then promised to be ready for him later tonight. Afterwards, the blonde left and went home. Collins knew that his horny wife would be excited at the prospect of getting her clutches into a beautiful, young woman like Lisa.

Then again... who wouldn't?


After arriving home, Lisa took a shower and washed up, but decided the outfit for her upcoming "date" would be the same one she had earlier worn to work. That, of course, consisted of the ultra-tight white top, along with the black, micro-miniskirt and the spiked high-heels. As was the case earlier, Lisa was not wearing a bra underneath her top. In addition, she had foregone the use of panties. She figured neither would be necessary.


It was 7:26pm when Lisa heard a vehicle pull up outside. She went over to the picture window and peeked through the blinds, then saw Mr. Collins' luxury car in the parking lot. A grin came to her face when she saw a sleek pair of woman's legs appear from the passenger side. So far, Lisa thought, so good. Mr. Collins' wife may have been 46, but hopefully she was as attractive as the man claimed she was. The darkness outside, however, prevented Lisa from catching a good glimpse of the woman's face.

Lisa rushed over to the front door and waited until there was a knock. After several seconds, it came and then the bombshell blonde opened the door with a big smile upon her lovely face. Lisa thought that Kim was everything that Collins said she would be... and more.

The boss' wife did appear to be younger than her age, as promised. She looked like a 35-year-old, with light blonde hair which went down to her shoulders. Kim also had a very pretty face, Lisa thought, and a trim body. Her style of dress - a blue knee-length skirt and matching business style jacket, gave her a classy appearance.

While Lisa was grinning as she checked out Kim, the older woman had already fallen in a mixture of love and lust.

"Jack," Kim said, "you told me that Lisa was beautiful. BUT WOW, I never thought she would be THIS beautiful!"

Lisa smiled at the woman. "Thank you, ma'am."

"Ma'am?" Kim said, grinning. "You also said that she was very respectful, Jack. I definitely like what I see."

"I knew you would, honey," Collins said.

Kim continued to look at the young blonde with lust in her eyes. "So tell me, dear... Have you enjoyed fucking my husband?" She giggled. "He's talked about you a lot over the past week or so."

"Yes ma'am, I have," Lisa replied, with a subtle grin. "What has he said about me?"

Kim laughed and replied, "That you're a hot little slut who loves getting fucked." She paused, looking at her. Wow, she thought... Lisa was gorgeous. "Is that true, dear?"

"Yes ma'am," Lisa returned, her gaze lowered. This was the submissive in Lisa coming out. She always seemed to melt when people spoke to her with any hint of authority.

Kim took a hold of the 20-year-old's hand. "Come on, dear. Let's get to the car. The sooner we get to our house, the sooner you and I can fuck."

Lisa smiled at the older woman again. "Yes, ma'am." She let Kim guide her toward the luxury car in the parking lot.

"Don't forget about me!" Jack, Kim's husband, said. He quickly followed behind the two ladies, and was gentleman enough to open the passenger side door for them.

When Lisa made a motion to get into the backseat, Kim stopped her.

"No dear," the older woman said, shaking her head. "I don't want you sitting in the backseat. You can sit between Jack and I, in the front seat. There's plenty of room."

Lisa offered yet another smile before she climbed into the big front seat. She settled down in the middle, then Kim got inside and squished her body hard against the blonde's. Kim used her right hand to reach out and grasp one of Lisa's big, firm breasts. The duo giggled and smiled at one another as Jack scurried around to the driver side and got in.

"Do you make it a practice not to wear a bra, dear?" Kim asked, tracing a fingertip around Lisa's protruding nipple.

"Sometimes, ma'am," the nymphomaniac replied. "To tell you the truth, I've never really liked wearing underwear."

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