Two Faces of Jess - Overnight Train (M/F) (CD)

[Brez510]

Introduction - Five months ago I chronicled a story about a guy named Jess, which was based on a totally true story about an 18 year old who crossdressed at a youth convention for a contest and later a video that was produced during the event.

I though the story, since it was based on real events, was a one off.

Surprise! I received messages here and on other sites that asked for more of Jess in a fictional version.

So, here it is several months later. Please read the original Two Faces of Jess to fully understand the character. https://tugstories.com/viewtopic.php?f= ... 59#p169459

This new story takes place nine years later.

Tina Gordon at twenty seven, just a few years after receiving her criminal justice masters degree, was the big rising star at Worldwide Recovery, a criminal investigation security firm.

The company deals with the investigation of high value crimes.

Tina’s supervisor Don Leonard called her into his office for a meeting. He started to tell Tina about Worldwide Recovery’s newest client Albert Palmer. Tina asked if that was the same Albert Palmer who owns APC Security Alarm. Don shook his head yes.

It seems Palmer had a major theft in his own home. A silver aluminum security briefcase was stolen from his safe when he was out with his wife for a long weekend vacation. The case housed his loose diamond collection valued at over two million dollars! Palmer didn’t go to the police. The thought of the public finding out the case was stolen from his own home, a house that featured his company’s best, most high tech and expensive alarm system would be personally humiliating and devastating to his business. His safe division motto was “The security of a bank vault in the privacy of your own home.”

It was assumed that the thieves knew this fact as well and probably imagined that they would never be traced or apprehended since Palmer would not want to go to the police.

Fortunately the gate security camera at Palmer’s home continued to work even though the rest of the system was disabled. He retained Worldwide Recovery to review the video and try to recover the case.

Don said he was able to identify the two thieves and the car they were driving. Don had the company’s forensic lab trace the license plate and scan the faces of the occupants of the car to identify the two thieves who were Larry Davis and Tommy Lender, two safe crackers, and security system disrupters with long records.

Through paid informers it was learned that Davis and Lender were going to take the City of New Orleans overnight train from Chicago to New Orleans to sell the diamonds in three days. They were taking the train to avoid flying and having to bring the case though TSA security. Driving might also be dangerous if they were stopped by the police for any reason.

Don told Tina she was the rising star at Worldwide and asked for suggestion on how to recover the diamonds on the train. The room was silent for quite some time. Tina then told Don that they should place an agent on the train to tail Davis and Lender. Since the file showed Lender was slower mentally then his partner Davis perhaps the agent could gain the confidence of him when his partner wasn’t around and trick him to get a lead on where they were keeping the jewels on the train. A 24 hour train ride allowed plenty of time to get the information needed to re-acquire the gems.

Don said that was a good start but that if that agent was able to snag the briefcase during the trip, and Davis and Lender suspected it was him they would tear the train apart trying to find the agent and the diamonds.

Tina’s eyes brightened up. Jess and Tina have been going out since they were 17 and recently got engaged. She thought she just might have hatched a full proof plan.

Tina told Don that at a youth convention, when they were 18, there was a role reversal contest. She dressed as a man and Jess as a women. The male “women” in the contest were pretty ugly, overacting caricatures of ladies! A totally sorry lot of would be impersonators, but Jess was a different story. Jess came out on stage wearing a tight black shiny latex mini dress that came up to just below his neck with sheer pantyhose and black patent leather stiletto heels. He wore perfectly crafted artificial boobs. His light blond hair which was shaggy had a style that fit either a male or female equally. Jess was wearing makeup with red lipstick. His legs with the enhancement of the heels made them as sexy as any female movie star. Jess swayed like the sexiest woman alive and spoke in a smokey, whispering, sexy voice.

Tina told Don that the girls in the room screamed, applauded and laughed with amazement while most of the guys at first just stared in disbelief. Jess’s uncanny resemblance to a beautiful hot woman was all the more convincing due to his lack of body hair. He was smooth skinned and hot looking. After the initial shock wore off guys started whistling at the female version of Jess. They won the contest hands down. Tina told Don she later convinced Jess to act as his female alter ego in a youth video filmed at the convention. It was a Charlie’s Angels spoof where Jess played a damsel in distress.

Tina told Don that if she could convince Jess to do a female encore, perhaps he could board the train as the male Jess and have the female version eventually grab the briefcase and fade into oblivion. Davis and Lender would end up trying to tear up the train to find someone who really didn’t exist.

Don only knew Jess from company events that he attended with Tina. He was a normal regular guy. In Don’s mind the plan sounded good but he couldn’t possibly, in his wildest imagination, picture Jess as a woman and get away with it!

Tina was getting in deep because she didn’t know how Jess would react to the plan if it was approved. Before she went to Jess she told Don that the next day she would bring the video that was shown at the convention and let him decide.Tina was also in the video and saved a copy.

The next morning Don met with Tina and four other executives to look at the Charlie’s Angels spoof video. When the 15 minute video ended Don and the other executives sat in total silence. They couldn’t believe their eyes. Jess was, transitioned, a beautiful women.

Tina knew in advance what their reaction would be. She studied each face carefully. She could see Mr. Stern and Mr. Nance were totally hot and bothered by the sexy female Jess. Don and Mr. Cummings just looked amazed and Mr. Waterman payed particularly riveted attention to the tightly bound and gagged Jess in the video when he was kidnapped in the storyline and held as the damsel in distress.

After a few minutes all agreed Jess as both the male and female cross dress version could actually pull the plan off! Now all they had to do was to have Tina convince Jess to take the job.

Tina spoke to Jess. At first he said no! He cross dressed for the youth convention nine years ago because he thought it would be fun. It was one time, only time.

Tina then told Jess Worldwide Recovery was willing to pay him $20,000 if he completed the job successfully. Jess then said to Tina he thinks he remembers where his heels were stored!

Jess spent the next several days working at Worldwide Recovery learning how to execute the plan. All possible contingencies were carefully planned out and discussed.

Don asked Albert Palmer if he could duplicate the brief case and fill it with fake stones that looked the part. Perhaps Jess would potentially need to switch the brief cases if he saw the opportunity. Albert Palmer called his jeweler to put together the duplicate case.

Don gave Jess an unlimited allowance to buy cloths and makeup for his transition. For the youth convention Tina helped Jess with his makeup. Here she had to teach him to do it himself. Jess also bought clothes, stockings and new heels that he had to practice with.

Tina told Jess he could dress casually and not need heels revealing tops or skirts for the train trip, but he insisted that he wanted to be as sexy as possible if he was going to try to seduce the slightly dim witted Tommy Lender to give up some information on the robbery and the diamonds.

Tina was starting to suspect that even though it has been eight years since he last cross dressed, Jess was getting sexually stimulated by the thought of playing the sexy female role.

After a few days Jess was ready to execute the assignment. The train was scheduled to leave Chicago for New Orleans the next day.

Jess was busy at Worldwide arranging and packing the two bags he would bring on the train. They included the folders and thumb drives that contained the plan to recover the diamonds. Both the male and female clothing he would be wearing, the duplicate case containing the fake diamonds, various electronic surveillance devices and his computer

Don was holding a long closed door meeting with Tina to make sure everything was in place.

Mr. Stern, Mr. Nance and Mr. Waterman invited Jess into one of the conference rooms. Jess didn’t know what the meeting was about but understood that the three of them, even though they worked at the company, were also major investors, who always got their way. They were accountable to no one. Not even Don.

Tina had suspected that Stern and Nance found the convention video with Jess to be very sexually hot, while Waterman seemed to be getting off on viewing him tied up and gagged by kidnappers as he played a damsel in distress. She told Jess her impressions.

Mr Stern had Jess sit at the conference table. All three looked at him. Jess is a very handsome guy. He’s stands at 5’6’ and slight in build. He has short shaggy light blond hair with slightly androgynous features that make him look both somewhat female and male. He is straight and looking forward to getting married to Tina.

Mr. Stern spoke. He said that the three senior staff members needed to totally make sure Jess was prepared. They wanted him to do a dry run for them dressed as the female Jess. Then Mr. Waterman chimed in and said he wanted to spend some time teaching Jess some evasive tactics in case he was captured. He claimed he was an ex Marine commando. Neville Waterman might have been in the Marines as a cook, but would have been one sorry commando.

Jess knew right away that this meeting was not in Don’s plans. Don was the head of the agency and never said anything about dry runs or evasive tactics. He knew this was a setup by three older men, sexually interested in seeing a young man transition into a beautiful woman.

Jess was by no means submissive, but he was smart and knew these three wanted to get off on seeing him cross dressed and possibly helpless. Jess turned on a submissive persona to get them going and told the three he would do whatever they wanted. Anything to please them as powerful men at Worldwide. He said it would take around 30 minutes to get ready.

Jess went to his suitcases in the office they gave him to use during his training. He took off his polo shirt, khaki pants, socks and loafers and began the transformation. He in a way was pleased because he needed to practice his makeup and lipstick skills one more time before the train departed in the morning. Jess applied the make up, added a silicone B cup breast plate to his chest, brushed his shaggy light blond hair, slipped his legs into shear pantyhose, pulled to his waste a very short tight black leather miniskirt, buttoned on a revealing white blouse then stepped into 4” patent leather stiletto heals. He looked at himself in the mirror and admired the transformation.

He did feel sexy dressed as a women and enjoyed getting guys off. When he made that damsel in distress video at the youth convention he imagined some of the 18 years old watching coming hard from the visuals, especially when he was tied up and gagged. He found that very sexually stimulating. The idea, even though he was straight, that some guys became rock hard when they saw him made him hot.

Jess walked down the hall from the office to the conference room. Intentionally he meekly knocked on the door. Stern opened the door and let Jess in. They had moved a chair away from the conference table so Jess could sit and they would have an unobstructed view.

Jess in the sexist way possible tightly crossed his legs. In the same smokey, whispery, sensual voice he used at the conference many years ago he asked the three men what he could do for them. He reminded them his job was to please them since they were his powerful bosses. He could see he had them ready to explode. Jess go up and took an alluring stride around the room stopping at each chair to ask if he could do anything.

The three big shots were totally flustered, sheepish and didn’t utter a word. Stern and Nance asked if they could take pictures of Jess both seated and standing. He obliged.

Perhaps Stern and Nance had other lurid ideas but at this point were too timid to ask. It was Jess who held all the power and he knew it, and it made him even hotter.

Stern and Nance said they would leave so Mr. Waterman could teach Jess some evasive moves. Alone with Waterman Jess asked in his sexy voice what moves he needed to know to avoid capture. He told Waterman he didn't want to be kidnapped or placed in peril. Waterman seemed to get hit and bothered after hearing that, but like Stern and Nance was reduced to mush.

They all thought they held the upper hand but they didn’t.

Jess asked Waterman sarcastically if he meant something like an evasive move if someone big and manly like him came up from behind and place their hand around his mouth? Waterman nodded.

He told him to do it and he would try an evasive move on Neville to escape. Waterman slowly walked up behind Jess and place his hand around his mouth. Jess let out a sexy long mmmmmmmmmph.

A sweating Waterman released his hand. He envisioned for days since he saw the video that he would be having Jess as his submissive gurl toy but that wasn’t happening.

He was intimidated by Jess’s sexy voice and hot persona.

Jess told Waterman to try again but this time to make his handgrip tighter. He told Waterman to also use his other hand to wrap tightly around his waist. Jess instructed him to use his hand gag hand to pull his head back. Waterman tried to follow Jess’s instructions. When he grabbed Jess’s waist and pulled him back towards him he could feel that Waterman was hard as a rock as their bodies touched. Jess moaned into the hand gag and then without warning took his right stiletto heel and stepped hard on Waterman’s casual shoe. Now it was Waterman who let out a moan as he quickly released Jesse. Jess didn’t know if Waterman was hard from hand gagging him or like that because he was giving Neville instructions to follow.

Jess then said to Waterman that they should cut to the chase.

He told Waterman that he knew his ulterior motive was to see the female Jess tied up and gagged. He told Waterman to do it. Waterman just looked at Jess. He said to tie his hands behind his back and make it tight. Very tight.

Waterman produced a bag of rope from under the conference room desk. He pulled out a length went behind Jess and tied his wrists together. Jess then told Waterman to push him hard into the seat that Stern earlier offered to him.

Jess sat down and crossed his legs. He asked Mr. Waterman if he found his legs with the stiletto heels on to be hot. Waterman nodded. Jess said then tie them up. I’ll cross them at my ankles. Waterman in his mind though this would be a macho intimidating tie up session with the submissive cross dressing Jess doing his bidding. It was now he kneeling and worshiping before Jesse’s crossed ankles fumbling to tie them together. Make it tight, very tight Jesse told him.

Jess then instructed Waterman to tie his legs above the knees.

Waterman obliged and asked Jesse if it was tight enough. Jess said it was adequate. Waterman was devastated that he only found his rope work adequate.

Jess asked Waterman if he brought a gag. Waterman whispered yes and produced a cloth. Jess instructed him to put a big knot in it thrust it between his lips and tie it tightly behind his neck. Jess first asked Waterman if he wanted him to pose in different ways so he could take pictures of him after he was fully tied up and gagged.

Waterman whispered yes please. Jess told him, that he would do a number of hot and sexy damsel in distress poses and that he should fantasize and jerk off every time he looked at the images and pretend in his imagination that he was actually the dominant man he though he was when he first had Jess seated in the conference room, and not the sniveling little man he actually was showing himself to be.

He asked Waterman if that was his motive to take the picture and then jerk off?

Waterman feebly shook his head yes. He then told Waterman to gag him, as tight as he could, take his pictures, untie him and leave the room. Waterman obliged.

Jess turned three manly men wannabes who wanted to turn their little private closed door meeting into some degrading, abuse the cross dresser party, virtually crawl into the corner and roll themselves into a ball.

Jess now knew he had the tools needed to confront the diamond thieves and retrieve the gems on the train.

Stay tunes for Part 2 as Jess boards the train for his mission to retrieve the diamonds.