Part 3
Jamie’s story
The few days before the date in Part 1...
The car pulled up at the curb and Jamie got out of the passenger side door. She was a bit wobbly on her three inch heels. The car sped away fast, as if the driver was feeling guilty about what he and Jamie had just done.
Jamie opened her purse and tucked away the fifty dollars she had stuck in her bra shortly after getting into the car. She also pulled out a cigarette and lit it, dragging deeply on the smoke. The flavour of the menthol cigarette helped to wipe away the residual taste of the cum in her mouth. A breath mint afterwards would help mask the flavour and odour as well, in case her next john wanted to kiss her.
While she smoked, she opened her compact and checked her makeup, she used a tissue to dab away a bit of cum from the corner of her mouth, and also a streak along one cheek. Fortunately she had managed to swallow most of the john’s load and there was not much damage to repair.
She also saw that her hair looked fine. She had taken her normal drab red hair and coloured it a bit more brightly and styled it more femininely for the evening. Before leaving the apartment she had changed from her more masculine day clothing to her preferred sissy clothing. And tonight, she had put on what she was starting to think of as her evening work outfit. In addition to her three inch heels, she was wearing dark stay up stockings, very skimpy black leather hot pants, a short short neon green tube top that left her pierced navel exposed.. oh and a very small pair of thong panties that barely contained her nice sized pricklet. She had a row of tiny fake emerald studs in her left ear, matching the large fake gem in her navel. The green looked very delicious with her red hair!
She was wearing small breast forms under her top. She had been getting hormone injections for over a year now, but was disappointed that her breasts had barely developed at all in that time. So little that they barely made any bulge in her top at all. On the other hand, she had been told that the hormones had been specially formulated that they did not cause any problems with her getting an erection. In fact, if anything, she was hard much more often than she used to be!
This meant that at this moment, anyone observant enough would notice the very slight tenting of her hot pants and would figure out that this particular street walker was not a girl. Which was not unusual for this section of the stroll in this particular area of the city.
But then despite thinking of herself as “she”, Jamie did not make any pretences of being a girl. She was a man, barely beyond being a boy, but in reality, she was a sissy! And she had all the cravings of a sissy. She wanted to look feminine. She wanted to dress feminine. She wanted to suck cocks and get fucked by cocks. But she definitely wanted to still be a boy and to have people know she was a boy - even if it was a limp-wristed cocksucking faggot of a boy!
Her life had changed dramatically over the past couple of years, ever since she realized she was a sissy. At the office, she was no longer a cub reporter, eagerly seeking out the latest crime stories and covering the exploits of her best pal, Superman. The hormones had affected her muscle mass and she was no longer fit enough for those adventures. Heck she was no longer even a reporter for the paper! As she had slowly developed more effeminate mannerisms and started swishing around the office, Perry had become more and more embarrassed at sending him/her out on assignments. Now when she heard the cry of “Olsen! Get in here!” it was not to be sent out on a story, but rather to be handed a bunch of papers to be filed away!
Lois and Clark had been sweet, but concerned. They had taken him aside, individually and together, to talk to him and express their concerns that he had perhaps been exposed to some exotic virus or toxin on one of his adventures to another planet, or perhaps one of the criminals he had exposed had done something to his mind! Jimmy, as he was still known at the office, despite repeatedly saying he wanted to be known now as Jamie.. Jimmy had just laughed at them and told them the truth... that after several assignments that required him to dress up as a girl, he found that he so much more enjoyed dressing more flamboyantly than his normal drab boy clothing.
And dressing more effeminately had drawn attention from men. Certain kinds of men. He quickly realized that he actually liked having men attracted to him. He wanted their attention. He began flirting with those men, nothing serious of course. After all, he was a man himself... wasn’t he? But the flirting got more daring and he found himself becoming more and more aroused by the attention.
All of this had escalated slowly to the point that even when dressed as masculine as he did for work - which he now thought of as “butching it up”, he was still wearing eyeliner and eye shadow, and his finger nails were always painted - and he was always wearing panties and stockings underneath! He was just dying to start wearing a bra to the office as well, but his titties had not developed enough to realistically need one!
When he was at home, well, then he could dress in all of the wonderful new outfits that his poor newspaper earnings could afford! Which was not a lot. Especially since he no longer drew a reporters wages. So he had had to look for other income.
As she strolled along the couple block stretch of this not very nice neighbourhood, she said hello to her competitors who were also trying to make a meagre living. They had resented her at first, but once they saw that she was not chosen much more than they, they just accepted Jamie as one of them. There were all sorts trying to earn a living here from the continual parade of cars. Some were just young men, selling their asses for drug money. Some were transitioning transsexuals, looking for more money to complete their surgery. A couple of others were like Jamie, mincing sissies, boys who would never be mistaken for girls, but were feminine enough to attract the men who did not think of themselves as gay, but who still wanted to find a dick when they lifted the skirt!
Jamie loved her BFF Robin. Robin was also a cockloving sissy, but she had it easy! Robin lived in a big mansion and had all the money she could possibly want. Robin was a few years younger than Jamie. The two had awakened to their sissy needs at about the same time and had given each other support. They had also given each other many many creamy cummies exploring each other’s bodies whenever they got together! Robin had managed to convince those around her to stop using her boy name, Dick. Robin seemed like just the right name for the sassy sissy!
Jamie missed Robin. They had not seen each other for almost two months. Sure they talked on the phone and texted constantly, but Jamie SO missed snuggling and cuddling their soft bodies together!
Another car slowly drove down the street, its window open so that the driver could inspect the various girls and boys who were calling out to him. The car stopped and the driver beckoned to Jamie. Jamie minced over to the car and asked the driver if he liked what he saw. Evidently he did because he told Jamie to get in. Jamie directed him to drive to an alley a couple blocks away. When they stopped they haggled over price briefly. Jamie was disappointed that the john was not willing to pay enough to fuck her ass - both because she had not yet had her ass fucked tonight and she REALLY needed a cock in her ass, but mostly because it meant she would not make as much money from the guy.
They got out of the car. Jamie took a flattened cardboard box and placed it beside the car. She knelt on is as she unbuckled the john’s belt and pulled down his pants. His dick was disappointingly small. Perhaps it was just as well that he did not want to fuck her. She would not have gotten any enjoyment from a cock that size - heck HERS was bigger! So it was just as well that she suck him off as quickly as possible and get back to the street.
