Part I

Jesse was as nervous as a cat on a hot tin roof.

She had only recently decided on her switch from James to Jesse and she was constantly looking in the mirror to determine if she looked like a real woman or just a guy pretending to be something he actually was not.

She knew in her favor was her petite size and her boobs that didn’t need any enhancement because they were naturally perky with lovely nipples that looked quite feminine. On the other hand she had an oversized package of male genitals that would be a dead giveaway the first time guy put an inquiring hand under her panties. She knew the operation was a long time off because of the many requirements she had to pass in order to qualify for a sex change. The ass and the boobs were easy, it was the lack of a vagina that was the stumbling block and she didn’t know how she would find a guy to overlook that fact during the time that it would take to complete the process. At the latest count it would take about two and a half years to finish the whole thing and she would still never be a mother but would have anatomical correctness in a visual sense.

Jesse was only around since last Christmas when she finally gave up the ghost of being a male once and for all in front of her entire family. She could still remember the looks on their faces and the disbelief cut deeply into her very core.

So here she was an unemployed schoolteacher in the midst of getting her license changed and her name change completed so she would resume teaching across the river in another state as a she and not a he minus the embarrassment that came along with meeting people that knew you in another world.

She knew she had hidden her guilt all the way back when she was in the boy scouts and she had to sleep in a two man tent with Bobby Brown and his dirty stories about screwing girls in the ass just to show the who was the boss.

He had laughingly given her a demonstration that had sealed forever her inclination to be a catcher and not a pitcher in the game of sex. His thick cock was poking her bottom with a persistent pressure until she felt something give and he was inside her stretching her virgin ass with rough enthusiasm. She did her best to open up for her best friend but also concentrated on pretending to be a boy and not wanting him to do anything at all. James only had one thought on his mind and it was the risk of someone discovering his hidden desire for Bobby to do it again on the next hike and she would continue to pretend to be totally reluctant to give up her ass to his crude attempts at love-making in the dark.

That summer James had become better friends with the Junior Assistant Scoutmaster Andre from Canada who had introduced him to the art of oral fun and games on his knees in front of the older boy. When the French-speaking Scoutmaster returned the favor to James, he was convinced it was a lot better being a girl than a boy because it was so exciting.

Then, he did that hitch in the navy on board a large ship with lots of men that had no females to fill the void of a long voyage without benefit of a bedmate that did nocturnal favors under the blankets. James had made a number of friends in the navy that he knew would never invite him to their wedding or even out on a date because it would be far too suspicious.

He almost got married to Stella with her short hair and her boyish good looks and muscular legs that she used to hold him down while she played with his cock and sucked him off with familiar ways just like one of the guys he had close relations with in the navy or even in the boy scouts. She was well aware of his anal fixation and used a strap-on to punish him when he didn’t do exactly what she wanted as quickly as she wanted it done.

Eventually that engagement fell through and Stella settled for an overweight confused female with a submissive nature that allowed the more aggressive Stella to use her anyway she wanted in the midnight hours and she just pretended Stella was really a boy and the strap-on was almost as good as a real live cock. Besides, Stella would bring in guys to screw her new wife right in front of her and she could look into her face as she took it all the way up with grunting pleasure. All in all, it was a satisfactory relationship and James was lucky he missed the boat because he thought it a complete farce and far too humiliating for him.

Jesse had cross-dressed often the past three years after breaking up with Stella and she was used to putting on the make-up and getting her wig on just right so it looked as real as possible. She had mastered the balancing act with the high heels and used them to go wherever she went because they made her ass cheeks look all perky and uplifted and ready to meet the world on her own terms.

In the last three years she had not been on very many official dates but she had gone to parties where she had met guys that were not fussy about not doing it in her soon to be installed pussy and were quite happy to use her mouth or her ass to get the release they needed and were satisfied with a happy ending. She knew that for the most part, those guys were not interested in permanent relationship and were just looking to get a piece of ass or a quickie blow job to get their rocks off.

There was one guy that called her back for another date but she turned him down because she didn’t want him to get too curious about why she wasn’t asking him to eat her pussy or something like that just like most of the other girls that were dishing out anal and oral sex without any favor in return.