Jeff had everything a 32 year old man could ask for. He had a beautiful wife named Lori, two wonderful children, was a manager of a successful company and provided an above-average income for his family. Jeff was handsome and at 6 foot tall and 185 pounds, he turned quite a few female heads when he walked by. Jeff did, however, harbor a lurid secret: He was a closet cross-dresser.
Although heterosexual, Jeff had a fetish for cross-dressing. Two or three times a year, he would get into a "mood" and buy all sorts of female clothing and accessories. Jeff got turned on dressing up.
After a few erotic sessions with himself, Jeff would feel ashamed and dispose of the "fetish" items. Then Jeff would revert back into being the manly white male he felt he was supposed to be. Jeff had gone his whole life without anyone discovering this secret. He intended on keeping it that way………
Marcus, a single 53 year old black male, worked as the chief security officer at a large hotel chain. Marcus was a whiz with security and surveillance equipment. Marcus made good money and had a lot of females at his beckoning call. Marcus, however, also had a lurid fetish. He enjoyed transvestites. Not only did he fantasize about them, he would occasionally cruise the strip late at night looking for a tranny to take back to his crib.
Unbeknownst to hotel management, Marcus had even installed hidden cameras in some of the rooms in several of the hotels he would oversee as the chief security officer. While Marcus enjoyed many a viewing of all sorts of sexual trysts, what Marcus really desired was catching a closet cross-dresser on tape. That was his ultimate fantasy……..
Jeff loved it when the month of September rolled around. Jeff's company would send him five hours away from home to attend a week long convention in a big city. While Jeff had never taken the opportunity to cheat on his wife, Jeff loved having the chance to cross-dress in the seclusion of his hotel room.
Jeff always stayed in a hotel on the other side of town from the convention so he could have maximum privacy during the evenings. He would begin a few weeks before the convention; purchasing all the accessories he could to enhance his experience.
This particular September, Jeff took with him a low cut button down cream blouse, a black mini skirt, a matching black bra and panties set , black thigh high nylons with garter straps, a garter belt and a pair of black 4 inch stiletto heels. Jeff also had a full accompaniment of make-up, a blonde wig and deluxe silicone 36D breast forms. While he would be attending the convention during the day, Jeff was really looking forward to spending his evenings inside his room dressing up.
Jeff checked into his hotel room late Monday afternoon after attending the first day of the convention. Shortly after he got up to his room, he started getting himself all dolled up. After he was completely dressed as a woman, Jeff would check himself out in the mirror, strut around the room and get himself aroused. He could feel his pre-cum already oozing in his panties. He could not hold off masturbation much longer.
Right before Marcus' shift ended, he quickly scanned all the rooms he was taping just to see if anything interesting had developed. He really did not expect to find anything of interest on a Monday night, but you never know. Then, low and behold, Marcus caught a glimpse of the vision he had been dying to see. There, right in front of his eyes, was a good looking white boy all dressed up as a slut in heat.
Marcus could not take his eyes off the screen as the tranny pranced around the room all dressed up. Marcus could just hear those high heels clicking around the room as this guy was swaying his hips around in that mini skirt. Marcus quickly popped out the tape to that room and inserted a new one to record through the night. Marcus had been waiting for this moment for a long time; He had a lot of work to do to fulfill his fantasy……
Jeff thought the second day of the convention would never end. He was especially horny today as he wore the pair of black panties and black thigh high nylon hose with garters all day underneath his normal shirt/tie/slacks combination.
As he got back to his hotel room, he was alarmed to see a tape sticking out of the VCR in his room with a note ominously saying, "Play me." Jeff walked around the room, checked the bathroom and was relieved to find no one around. He chain-locked the hotel room door and sat down at the edge of the bed. He pushed the tape in and awaited its message. An older black man appeared on the screen.
"Hi Jeff, I'm Marcus and it's a pleasure to meet you."
Jeff stared on in shock as Marcus continued. "You are wondering right now what in the hell is going on, aren't you? I will quickly get to the point. I've got you on tape getting all dressed up, and you know what I mean. You're real pretty, by the way."
Marcus grinned real big. To Jeff, it appeared as a grin that the Big Bad Wolf would have when talking to Little Red Riding Hood. Jeff could not believe what he was hearing. How did this guy know who he was and that he "dressed up?" Jeff felt really flush in the face as he felt his proverbial closet opening wider by the second.
"I did some checking on you, Jeff," Marcus continued, "and I know about your wife Lori and that you have, is it, two kids? I am wondering if Lori and the kids know you like to dress up real pretty? Do your parents know? Your employers?"
Jeff had a feeling he knew where this was headed. This guy, Marcus, somehow discovered Jeff's secret and was going to try and extort money from him.
"I will tell you what I want tonight, in person," said Marcus. "I want you to meet me in the middle of the alley to the left of the hotel at 9:00pm sharp tonight. You will meet me dressed up like a girl just as you were last night. I want to see you in complete make-up, with all the undergarments, your breast forms, the wig, blouse, skirt and heels."
Jeff couldn't believe his ears. What was this guy Marcus trying to do? Jeff sat stone-faced as Marcus continued his series of demands.
"I also took the liberty to buy you a black purse to go with your outfit," said Marcus. "You will find it in a bag under the bed. You will also find some perfume that I want you wearin' when you meet me. You will bring the purse and put your make-up accessories in there."
Jeff reached under the bed and found the bag containing the purse and the perfume this Marcus character had purchased for him.
"A purse," thought Jeff. "This guy must really enjoy humiliating people."
The tape of Marcus' demands continued.
"You will not leave the room until you are dressed up and ready to meet me," said Marcus. "Also, you will not make any phone calls. Remember, I am watching you!"
Marcus was very clear on his final set of instructions. "If you are not in the alley by 9:00pm and you are not dressed as I have demanded, I will see to it that your family, bosses and many others will get to watch the following tape along with a letter to explain your dirty little secret. See you soon!"
With that Marcus cut out and the tape showed exerts of Jeff dressed up from the night before. It even showed Jeff lying face down on the bed humping a pillow that was between his legs while he was dressed up as a woman.
Jeff didn't know what to do. He looked at the clock and it was 6:30pm. He had only a couple of hours to decide how to handle this major dilemma.
Marcus was watching live as Jeff viewed the tape. Marcus had been a busy man since he had discovered Jeff last night. Marcus used his connections at the front desk to research Jeff's personal information as well as how long he was supposed to stay in town.
Marcus also used the help of a private investigator he knew to learn as much info on Jeff as quickly as possible. Marcus was banking on the hope that Jeff was still in the closet about his cross-dressing. If Jeff didn't really care about coming out, not only would Marcus' plan fail, Marcus would also probably lose his job and face criminal charges if Jeff pursued it. But Marcus was confident that he would be seeing Jeff at 9:00pm on Marcus' terms…….
Jeff waded through all of his options. Bottom line, Jeff did not want his family or anyone he knew finding out about his secret. Jeff's options were also limited because this guy obviously had some sort of hidden camera in his room watching his every move.
Jeff did not understand why this guy wanted him dressed up. If he simply wanted money from Jeff, why couldn't Jeff just meet him dressed as a man? Whatever the case, Jeff knew he couldn't risk this guy letting out his secret. He knew he had to start getting dressed up to meet Marcus.
It was very difficult for Jeff to get ready. For one thing, it was very unsettling knowing a hidden camera was watching him. Also, he was worried about what this guy wanted. Although successful, Jeff did not have a lot of money to spare. How much would it cost to make this guy go away?
Jeff went into the bathroom and started to get dressed. First he attached his deluxe silicon breast forms with surgical glue that gave him a firm 36 D bust.
Jeff put on his thigh high black nylons over his smooth legs that he had shaved last night. Then he slid on his garter belt with four black garter straps trimmed in black lace that attached to his nylons. Jeff slid into a pair of black panties and put on the matching black bra over his breast forms.
Jeff began applying a foundation of liquid make-up to his baby smooth face to give it a tanned complexion and used a soft powder to set it in place. He then applied an adequate amount of blush.
He trimmed up his eyebrows and applied thick black mascara and eyeliner. His brown eyes were set off with a soft gray eye shadow. He painted his nails red and put on a pair of hoop earrings. What was usually an erotic experience for Jeff was turning into sheer terror.
Jeff finished dressing up by putting on his low cut button down cream blouse and a short black mini-skirt. He affixed his blonde wig and put on his 4 inch stiletto heels. Finally he applied red lipstick and lip gloss over his lips making them appear very moist.
Jeff sprayed the perfume on his blouse, gathered up his make-up, put them in his new purse and was ready to go. It was 8:45pm. Jeff had only fifteen minutes before his date with destiny.
Jeff now had to worry about his first walk in public as a woman. Jeff had always fantasized about going in public dressed like a woman. Until now, however, he had never once actually considered doing it. Now he was being forced to do it.
He had to go down the hall, on the elevators and through the downstairs lobby before getting outside. Lord knows how many people would see him. Hopefully, it would be no one he knew. Jeff knew that at six feet tall, he would certainly draw attention. Even though he was dolled up real good, it wouldn't take too close of an inspection to realize he was a guy.
Jeff's heart was pumping a thousand beats a minute as he opened the door and entered the hallway. He was only about one hundred feet from the elevator so he moved quickly. He had never walked this fast in his heels before and he was afraid he would fall. He was relieved when he made it to the elevators without being seen.
Before the doors to the elevator opened, Jeff had already decided on his strategy for getting through the lobby. He would walk as quickly as possible and not make eye contact with anyone. Jeff felt that as long as he did not look at anyone, he would be invisible. If he didn't notice anyone's reaction to him, then it wouldn't bother Jeff.
As the doors opened, Jeff hurried off with his heels clicking loudly through the lobby. He knew there were people around, but Jeff focused on the front doors and the dreaded meeting that awaited him around the corner outside.
Marcus had stayed in his office monitoring Jeff until Jeff was fully dressed. After seeing Jeff all dressed up, Marcus was fully confident that Jeff would comply with all of his demands. And there would be many of them. When Jeff exited his room, Marcus quickly left his office and hopped on the service elevator. He then exited the hotel through a side door and hopped into his awaiting car that was parked in the alley where Jeff would meet him.
As soon as the cool evening air hit Jeff's face, he knew there would be no turning back. He turned left and quickly clicked his way towards the alley. As he turned the corner, he could see a car halfway down. Thankfully there were not a lot of people on the street to see him. As he made his way down the alley, Jeff was still holding out hope that Marcus was just playing him and would not really be there. That hope was squashed when the car flashed its lights at Jeff. He had a sinking feeling Marcus was there.
As Jeff approached the car, Marcus rolled down the driver's side window.
