Four for the Ride Pt. 01

Jessie was a 29 year old journalist from the east coast. Just starting out in her journey to conquer the world of mass media and the chance to reach millions with the written word. Although at the present she was still working for a small town paper in the mid-west. Content and satisfying a job, but not where her dreams and ambitions drive her to go. One thing that her sleepy Midwestern town did not know about Jessie was her insatiable appetite for sex, especially of the group variety. Jessie had her stable of boys, Leo and Jason. They pleasure her in many ways, but she wanted more. Always on the prowl to push her limits she floated the idea of adding a 4th to the mix one night while getting DP'd by Jason and Leo. Both guys sort of shrugged it off as merely pillow talk in the throes of passion, but Jessie was serious. She already had a 3rd gentleman in mind.

Billy, a 34 year old Computer Executive she met last fall at a Conference for work in Vegas. Sharp dresser in his tailored suits and silver Rolex Submariner watch. He was a down to earth gentleman, a self made man. That appealed to Jessie. Billy wasn't another pompous rich white guy in his Cadillac but a mid-western roll his shirt sleeves up and get the job done type of guy. She knew there was more to him when they chatted about mass media and ad sales. There was more to him and she wanted to know what that was.

They kept in touch professionally the past few months on LinkedIn and Facebook. Imagine her surprise when he messaged her to let her know that he would be in town to visit her small-town newspaper to demo some media editing software that her boss was interested in purchasing. This was her opportunity to see if she could workout a way to get Billy into the fold with her boys. What a night it would be, but how to approach that subject with him. She just decided to ask him and let the pieces fall where they land. Besides no one would believe him anyways. Jessie had a pristine image at work and personally with her close friends, they never knew her sexual secrets.

It was a sunny day in May, a Monday when Billy showed up at Jessie's office on that big day. Professional and courteous, Billy made his sales pitch and demo'd the software to Jessie's supervisors. All the while Jessie sat back in her chair wondering how she was going to approach Billy about her plans. She also noticed that he had either a pair of rolled up socks in his pants or he was packing some serious heat. Either way, the motion in which he moved in his slim cut pants curved and accentuated his torso, calling attention to his crotch.

"I wonder if anyone else sees this?" she thought to herself. Jessie then noticed how wet she was getting under her summer dress. Probably should have worn panties today she thought to herself. After the meeting Jessie stayed in the conference room wth Billy and helped he clean up and put way the A/V equipment.

"Its now or never," she thought to herself. Cautiously she walked over to Billy, her pussy still glistening from the thought of his cock that now she determined she had to have. Her 4 inch heels made a clicking noise as she walked toward her prey.

"Those are some very sexy heels you have on there Jessie," Billy said to Jessie. "Jimmy Choo's?" he asked.

"Why, Yes they are," replied Jessie. She was flattered that a gentleman such as Billy would notice such a thing. "Well they look amazing on you, perfect legs if could add."

"Hope I'm not being too forward," asked Billy. Jessie was a little taken aback by his comments, but she did where her 4 inch 'fuck me pumps' to the office today just for him. She decided she would push the issue a bit but Billy beat her to the punch.

"How about dinner tonight?" he asked. Jessie agreed and the foundation for her 4 some was put into motion.

Billy drove out to her house at 7pm and picked her up in his rent a car, nothing flashy, just a typical 4 door rental.

"What do you have a taste for?" Billy ask.

Jessie already had a quaint little French bistro picked out for the evening. Perfect place to be alone, but still busy enough not to be a secluded romantic spot. The evenings dinner went quickly, both discussing their jobs, likes and dislikes. Jessie was amazed by how at ease Billy made her feel, like she had known him for years. After the second bottle of wine and the conversation drawing down, Billy made a statement that completely surprised Jessie.

"You know how incredibly attractive and amazingly beautiful I find you?" Billy said.

Jessie blushed, she knew at that moment that he wanted her, only would he go for what she was planning? Maybe it was the wine, the company or the bistro, but Jessie just laid it all out there for Billy to process.

"I want to take you back to my place and have you fuck me with 2 other guys..." Billy stopped for a second, smiled and sat back in his chair.

"Are you serious Jessie?" asked Billy.

"As a heart attack," replied Jessie. Billy sat there in amazement. He wanted Jessie, but under these circumstances? She looks so amazing in her dress and heels. She smelled like woman, she carried herself like a woman, but she must have the sex drive of an animal. That was all that Billy needed to convince him.

"I'm game!" stated Billy, and the two of them finished their wine and drove off to Jessie's place where Leo and Jason waited...

Jessie and Billy arrived at her place after 10 and all was quiet on her street, no one knew the kinky festivities that were about to take place. After a brief round of awkward introductions between Leo, Billy and Jason. Jesse surrendered herself to her room to prepare for the fucking that she was about to receive at the hands of 3 cocks. The boys tried to have normal conversation in the living room while ESPN was on the TV. Trying to break the ice Billy suggested a round or 2 of drinks. Jason walked over to the cabinet in the dining room and brought out some bottles of bourbon and vodka. Perfect Billy thought.

Meanwhile in her bedroom Jessie got ready. She took off her dress and sandals, removed her bra and panties. She wanted this night to be special. She finds her short black tank top dress, it was probably meant to be worn as a shirt and with tights because it was ridiculously short, it barely made an attempt to cover her sexy legs and round perfectly shaped ass. Perfect she thought. Now to the heels. She knew that Billy and the Boys liked when she wore her heels, this is a special night, it calls for a special heel. She scanned her closet for that brown Louboutin box that she kept her 5 inch Louboutin So Kates in. Just the right shoe for the perfect occasion. Jessie slid on her heels and looked at herself in the full length mirror at the end of the room. Doesn't get much sexier than that she thought, but she was still missing something.

Accessories she reasoned. There was a green jeweled stainless steel butt plug that Jason had gottern her but she never had the nerve to try it out. Too large she always thought, but not tonight. Squatting down in front of the mirror Jessie took a tube of KY jelly and moistened her fingers and the tip of the plug. So heavy she thought, how will I keep this in? she wondered. Slowly she worked the tip and the large plug into her tight but waiting ass her hole closing around the shaft of the plug. She then put a gold chain around her ankle and another on both wrists. Dressed to kill she said to herself as she check herself in the mirror. My boys won't know what hit them as she whispered to herself as she opened the door. Slowly and sultry she waded out into the living room to give herself to her men.

To be continued...