The Tart Pt. 01

Note: This story was inspired by an anecdotal account of a famous author's days at college. I will not name this person to avoid any controversy. He didn't participate in those events, but reported that there was a custom where some of the most feminine boys were kept as "the tart" of some of the upperclassmen. In that instance it was probably done in a more traditional gay male relationship, but really there are few details of it so we don't know. I have modified it to suit what I find interesting to write about so this is not at all an account of those real life events or people. Those only served as inspiration for this, and this is quite different.

Also, this is set in a fictionalized version of England. It is in no way meant to be a realistic portrayal of the country or its people. Any factual errors are my own fault. It just made more sense to set it there because of the history of private academies and certain cultural aspects. In many ways I see this as having much more in common with an anime, and in fact there is an anime called "Princess, Princess" that was a big influence on the scenario of this story. Check that anime out. It's really good for anyone interested in transsexual/cross-dressing activities. When I was writing it I tried to visualize it as such.

PS: I have no hate towards gingers. Also, because this takes place in "England" references to football are not to American football but soccer. I really don't know the game well, but it made sense to include it for a school with characters this age. Everyone is of course over the age of eighteen.

Hope you enjoy.

*****

Ashley's mouth still tasted of the sweet cherry-juiced drinks she'd been given. She didn't much care for the harsh alcohol that some of the lads brewed secretly in their dorms. She had to have it mixed and disguised. They didn't think less of her for it though. She was their "girl", and the lads were willing to make allowances. That was all very nice for her. Her old life had been spent feeling inadequate.

Someone was helping her walk. She thought that it was James. He was known for being a "quiet one", but was very protective of her. James was only a little taller than she was, and not much more is mass. They could've made a great couple. He was a ginger though—some Irish or Scottish blood from back in the day. At this kind of academy so far in the south that made him stand out, but Ashley was hardly one to judge. She liked his bright red hair. Her own was a dull brown, and not quite long for a "girl". Sometimes that somber detail made her whole persona slip slip when she practiced it in front of the mirror.

"Where are we, James?"

"I think we're in the southern hall by the gardens."

"That's not where my room is," she said. The world seemed to tilt a bit for a moment, and if James hadn't held her she would have fallen.

"I've got you," he said. "I won't let go."

She smiled. "Is that a promise?"

Ashley hiccupped, but not before she saw the ginger blush. What a load of color that was!

"You're very special," James admitted. "I really didn't think I'd get this close to you considering some of the other upperclassmen around you."

"My seniors," she said, almost breaking out into laughter.

"It's not that bad anymore, right? Now that you are..."

"—the tart, I know. It's okay, James. Some things are just meant to be. You didn't do anything."

"Do you like this? Being this way, I mean."

She really had to think about that. Her life had changed so much in the last few months, and technically she still might go back to her old self...to Ashton. That all seemed so far away.

"I like being treated nice," she said. "Are you going to treat me nice?"

"Of course I am. I lo-"

"—don't say that. This is school, James. Being away at school is like being in a different world. There is something to go back to."

"You don't like it then?"

He seemed to have deflated, and she really worried that he would drop her.

Ashley kissed him on the neck. James tried to play that he was beyond that, but she knew he liked it. They had taught her how to get at the young men.

"Why did you make sure to grab me, James?"

"I saw that you had drunk too much is all."

She cleared her throat. "I likely wouldn't have been mistreated by our mates. They all know the rules, and what happens if they don't follow them. Do you want me, James?"

He didn't answer her, but held her still.

"I'll be yours, James. For tonight, as the rules go. If you want me then you have to say it or please take me back to my room."

"I do," he said finally. "Even before you were like this, I think that I found you to be somehow beautiful."

That made comment made Ashley feel very good, and it may not have just been the alcohol. To think that even Ashton, as scared as he was, could be desired. It made giving into James' desire all that easier.

"Do you have some place for us to go? The Regulators really shouldn't catch us out here."

"My roommate is gone this week."

"Take us there then."

It took nearly half an hour to get to James' dorm. A few of the other classmen saw them, but said nothing. Everyone knew that it was just the way it was. That was why a "tart" was such a special thing. Beyond her graces, well the lads may as well have been wanking off in a sock. There were instances of lads doing lads. The administration tolerated behind closed-doors, but it was considered unseemly.

When they got to his room, James helped her over to the bed. He then went to get the bathroom to get her a glass of water, which she imbibed vigorously.

"I think that truly helps," she said. "I really don't want another hangover, though I won't get in trouble for it, will I? Some bangers and mash certainly helps with the hangover though. You ever use that remedy?"

"No."

James' room was much like so many of the other dorms at the academy. He had the usual football posters and even a jersey on the wall. What drew her attention was a small poster of "Faery Song" by William Butler Yeats. She loved that poem. It spoke of such isolation, but comfort away from the judgmental world. She could have laughed. It was a poem about two lovers asleep in their bridal bed. She did like his bed. It was one of the older, larger ones.

James brought her some more water. He was not the kind to take advantage of a drunken tart.

"Keep this up and I'll have to piss," she said.

"The bathroom is over there."

She looked at him then. He was thinner than many of the others. Very nice though. A good guy had to get the girl some time, even if she was not quite a "girl".

She asked him how it would be. "Are you going to make love to me or fuck me?"

It seemed that the question was a little off-putting to him. At last he said: "I want to make love to you."

Ashley was glad for that. Glad to be with someone who cared.

"Get undressed," she said.

James did so while she took off her shoes, and in no time she beheld his slim physique. Running and kicking around a football had done him well over the years. He had the slightest tuft of chest hair, and down below a trimmed pubis of dark red hair. His cock was actually a good size, but not a monster. That was nice.

"Very nice," she said.

Ashley worked at her dress-shirt for a time, and then had it off. She tossed it across his room for fun. Then she unhooked her bra revealing her silicone falsies that she glued in placed and blended in with make-up every day. They were quite life-like even down to their perky nipples. Her real nipples were sore beneath them. The hormone treatments had been slowly causing natural breasts to grow. She wasn't sure how she felt about that.

Ashley leaned back on the bed, so she could slide her trousers off, but left the panties on. She called James over. They kissed, and she felt at his chest and shoulders, and he just embraced her. She admired the fact that he was bigger than her and firm. A little pale maybe, but that was a ginger.

After a time, Ashley lied back on the bed, and was actually quite cozy.

"You're not disappointed so far?" she asked. "Not everyone goes for one of us tarts."

"I do."

He was being so good to her that his whole thing seemed to be a crime. She sat back up and kissed him then. James was different from the others. He may have been as nervous as she sometimes was. She could feel his cock growing against her. He did want this.

James finally felt comfortable enough to fondle her breasts. They weren't quite like the real things, but she couldn't help that. The hormones they gave her were having some effect, but she wasn't sure that she wanted to go that far.

Her hand felt at his hardness, and she decided to help him out. She untangled herself from him, and let him lie down on the bed. Ashley put her hands on his thighs, and brought her head to his crotch. His cock was near throbbing with desire now. She brought her mouth down atop its length, and nearly swallowed it. This brought an immediate moan from James. She moved her tongue around it inside of her mouth, and his reactions told her that she had him.

"Oh my God," he uttered. "That is so good."

Ashley loved it when she had them that way. It confirmed that she really did have the power than some people said she did. They wanted her to be their girl, and so she would be.

Ashley kept at it. She brought him to the back of her throat, and then pulled away with a hard suck like she might give to a hard candy. She cradled his balls, and felt them up with her left hand. She squeezed them a bit. They were big, and would give a good load.

"Ashley," James said. "Oh, Ashley...I'm gonna..."

She stopped, and pulled her mouth away with one last lick at the slit of his cock. That nearly drove him over the edge. Ashley knew that it could be better though. She had learned what the guys at this school really wanted.

"Do you want to be inside of me?" she asked.

James could only manage a nod.

Ashley retrieved her pants, and from the pocket took out one of the slim packets of petroleum jelly from the nurse's office. They'd given her and others several of these.

She and James switched positions so that Ashley was on her back and James looming over her. She was heavily turned on herself, and felt her own hardness straining against her underwear. She was leaking with desire. James moved his hands to her hips, and took hold of her white cotton panties, and slowly pulled them down.

It made her very nervous, even though anyone lying with one of the tarts knew what to expect. Her own cock was rigid. She had recently shaved herself again, which only seemed to show off more.

She caught James looking at it for a moment, and she worried that this would be the end of their whole time together, but instead he touched her. He stroked her gently, and her breath caught in her throat. James gave her this little treat for awhile, but she knew that his needs were more important than hers. Ashley lifted up her legs and bent her middle to angle her bottom up. She ripped open the jelly and squeezed its contents onto the fingers of her right hand. She then worked those gently into her ass. She'd been practicing this for a while, and little by little had developed the necessary ability to relax the right muscles. Her fingers wormed their way in to further loosen and lubricate it. After a while, she pulled them out and looked to him.

"You'll have to tease me a bit," she told James. "It takes a while for it to get ready."

James found the packet of jelly, and put some on his own fingers. Slowly he worked one into her ass and moved it around. She relished the idea of someone being inside of her. It wasn't always that way, but over time her idea of pleasure had changed. This wasn't any easy place to get to, but after months of practice she believed that she had arrived. After a few minutes of his probing Ashley believed that she was ready.

She reached over and felt at his cock. He was ready. She pulled on it, and James quickly got the idea.

James gripped her by the back of her thighs. She guided him with her hand into her ass—or her "tart pussy" as some called it.

She cried out a little as he entered her. It was always that way. Ashley had been told that there would often be some pain, but that was just part of the role that she played.

James noticed her reaction to it, and hesitated.

"Am I hurting you?"

"It's alright. I want you inside of me, James. Fuck me, please."

James pushed himself into her more. The pressure of his body on hers made Ashley exhale. The feeling of his cock inside of her made Ashley grip the sheets with her hands. He began thrusting slowly. With every thrust there was pressure on her prostate that made waves of pleasure to her cock. She felt she might burst at any time. James' balls were hitting the lowest part of her butt and her own were mashed against the top of his pubis.

Despite all of that he was gentle—her silent ginger.

Ashley reached up to put her hands on his chest. James wasn't exactly strongly built like some of the others, but she admired the hardness of him. He was still more impressive than she had once been. That was all in the past though.

James fucked her harder. He'd found his rhythm, and was like a man possessed. She told him how good it felt, and how big he was. It was true that such was all a part of her role and training. Yet it was true in its own nature. She had to be careful about playing favorites too much though. Her purpose was to relieve their sexual frustration and give them a girl to woo and compete for. They didn't want her to create potentially disruptive conflicts.

James and Ashley continued for several minutes. The more that James fucked her ass the harder her own cock got. Ashley began stroking it as James got closer. They hadn't brought one of the condoms with them, but there was really no chance of her getting pregnant anyway. This was one more of the many reasons that the tradition of "the tart" was tolerated and even supported.

"I'm...I'm almost there," said James. "Should I?"

"Your choice, love. You can leave it in."

There was such a profound look of gratitude on his face. This was the kind of intimacy that young men secluded at an academy didn't normally get.

James tensed, and then for a moment seemed to stop. He pumped her full of his cum, coating her insides. Her own climax arrived, and she covered both of their stomachs with her own spunk.

They both took a moment to catch up on their breathing. James slowly eased himself out of her. The withdrawal usually ached some. She would have to take the next day easy if she could and do the exercises they taught her. It might even be longer until she was with someone again. She wasn't required to always have sex with them. The possibility just had to exist. She was a tart but not a whore.

James leaned down and kissed her softly. It wasn't the kiss of someone who had just fucked her, but someone who had made love and that really meant something to her. James rolled off of her, and then lied down next to her on the bed.

"Are you okay?" he asked.

Ashley nodded. By this point she was getting used to it, and actually finding it highly enjoyable.

How had she really gotten to that point? She was really thinking like a girl most of the time now. Did Ashton even exist anymore?

She leaned over to kiss James' neck, and told him that he was amazing. It was Friday night so she could sleep over till morning. She didn't feel like sneaking back to her room anyway.

James put his arm under her head, and they cuddled. It was a small but nice thing. That was how this all had started: a small thing, a change to the normal schedule of a student at the academy. She remembered the day she had arrived as "Ashton".

To be continued...

*****

Post Script: I hope you enjoyed this one. I've been kicking it around for a while, though that's how it normally is with my stuff. Some parts of this story might be "slower" compared to other ones. While I do appreciate a good quickie, I do prefer to get to know the characters that I write about. "Ashley" was a special idea that I had, and I want to explore her. I also like the setting, so I hope you give it a chance. As always: I would very much appreciate your votes and comments. Those are what help me know that I'm on the right track. I might not completely change gears, but am always willing to reconsider my grip on the wheel.