An Unfortunate Love Ch. 01

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Dorothy sat on the kitchen counter, eating bran cereal and kicking her heels against the cabinets below. It was early morning on a Saturday and she was usually the only one in the family up so early, but not today.

“Really, Dot, you are the craziest teenager I know,” Garret, her big brother, said entering the kitchen. “You’re up before the hens, on Saturday no less. You perch on the cabinetry instead of using perfectly good chairs. And you eat, and enjoy, old-people cereal.” He shook his head as he examined the enigma of his younger sister in all her morning glory.

“Yeah, well what are you doing up so early?” Dorothy asked. Her brother, despite being in college, where supposedly responsible people go, was the least responsible person she knew. He lived at home because he didn’t have a job, and had no interest in getting one for that matter. Their parents did everything for him, including his laundry, cleaning his room, and feeding him. Dorothy was eighteen and in her last year of high school.

Garret said that he didn’t have time to worry about the hassles of day-to-day life, because he was an artist, and he had to create art when the mood struck him. Therefore he could not have even a part time job, which would just interfere with his real calling. And his parents went along with it because he had won several awards for his paintings and photographs. Some were even in a gallery, and selling albeit for minimal prices, which is how he got his spending money.

“I’m going to meet with an art dealer, who is interested in some of my work, and wants to talk about making a series,” he said in answer to her question. He picked up a bagel and popped it into the toaster.

“Oh, cool.” Dorothy went back to eating her cereal. She wasn’t really interested in his art career. She knew he was good, because other people said he was, but she just wasn’t the biggest art fan.

“Mmm, hmm,” he said getting the cream cheese out of the fridge and setting it next to the toaster, “And guess what paintings she really likes,” he leaned one hand on the counter and stared down at her.

“Which ones?” she asked. Dorothy was finished with her cereal, and set the bowl with the left over milk on the counter. “Smoky,” she called to her cat.

“The ones I did of you.” He tapped her nose with his finger as he said it.

“Me? Really?” she said surprised. Garret pulled his bagel out of the toaster and spread the cream cheese evenly onto both halves.

“Don’t sound so proud of yourself,” Garret said, rolling his eyes, “They are my paintings don’t forget.”

“Yes, but it is my alluring beauty that draws people to them. Thank god you have me, or your art career would be in the trash,” she said jokingly.

“Yes, my little muse,” he said smiling fondly at her. She hopped off the counter, and left him alone to eat breakfast with Smoky.


That evening, Garret, Dorothy, and both their parents sat eating dinner around the kitchen table. It was rare in their house to have family dinners, because their parents were either traveling or working late, or one or the other of the kids was out, but tonight they had all gathered to feast on spaghetti and meatballs.

“So you know how I met that art dealer today? Well, after talking, she said that she loved my paintings of Dottie so much; she wanted me to make it a series. She would even give me a cash advance for any supplies I needed.”

“That’s wonderful sweetie,” their mother said beaming.

“Yeah, but the best part is, they’re going to show in a gallery opening in Paris in four months.”

“Ahh ha, I knew you could do it son,” their father said clapping his hands. “Didn’t I say he would be a famous artist some day?” he addressed their mother, then turned to Garret, “Even when you were a toddler, I knew, I just knew you would grow up to be an artist.”

“Honey, four months? How many painting do you need?” their mother asked worriedly. Both parents had always been very supportive of Garret’s career, but his mother had always been the more practical one.

“Well, at least six more,” Garret told her, “But it shouldn’t be a problem, I just have to work really hard, and I need Dottie’s help as much as possible.” Garret turned to Dorothy to get her agreement on the subject.

“Of course your sister will help you, this is a huge opportunity,” their father said, and continued to eat his spaghetti.

“Yeah, I’ll model for you,” Dorothy agreed, although somewhat reluctantly. She didn’t mind helping Garret, but modeling could be boring and tedious.

“Thanks,” he said looking at her seriously. She nodded and continued to eat, barely catching a glimmer emotion in his eyes that she didn’t have time to put a name to, but when she lifted her head again a second later, he was already back to eating, not even facing her. She dismissed it, and returned to her dinner.


Dorothy sat in the tree in the back yard, resting her head against her arm, which was resting against the trunk. The tree was a big oak, but amsterdam shemale it had a branch low enough for Garret to pick her up and set her down on, telling her to stay.

He now painted her furiously. Dorothy didn’t understand why she even had to be there. His paintings were realistic enough where one could tell it was a painting of her, but they were not portraits by any means. He could probably do it from his mind, she secretly thought, or a picture of her. When she told him that though, he rejected it, saying he needed inspiration, a live model, not a two-dimensional photograph.

Dorothy wasn’t sure how long she sat in the tree, but long enough for the position to be incredibly uncomfortable. Garret, somehow sensing her distress, finally put down the paintbrush and walked over to her, lifting her out of the tree.

“Come on, little bird,” he said as he did it, then setting her to her feet. “That’s enough for today. Why don’t we go inside and watch a movie, order a pizza?” he asked.

Dorothy shook her head, “No, I have a date tonight.” Garret looked at her fiercely.

“Oh yeah, with who?” Dorothy was used to him playing the protective big brother act.

“His name’s Josh, he’s really nice. We’re just going to see a movie,” she said smiling.

Garret looked at her suspiciously. “Okay, and you better be home by ten. With mom and dad out of town, I’m responsible for you.”

“My curfew’s not till midnight, come on, I’m not a little girl. I’ll be leaving for college next year.” Dorothy told him as they walked inside.

“Don’t argue with me, be home by ten,” Garret said in his most authoritative voice, which was very authoritative, despite the fact that he was usually so laid back.

“God Garret, you’re such a bully. Why can’t you just let me slide, be my friend?” Dorothy was mad; she would lie to mom and dad for him.

“We are friends,” Garret told her.

“You are not my friend, friend’s have each other’s backs,” she said and slammed off to her room. Garret knew why she was mad, she wasn’t a baby and didn’t deserve to be treated like one, but if it were up to him, she wouldn’t go out at all. She would stay home with him, forever.

Dorothy didn’t come out of her room, until eight. She didn’t even call to say she was leaving, only slammed the door closed. Garret ran to the front window just in time to see her hop into a beat up old car. If he had seen the short skirt and tube top she was wearing before she left, he would have made her change.

Garret sat in the comfortable living room chair, flipped on the T.V. and prepared for a long night. He desperately hoped she would be home by ten, and couldn’t stop thinking about what she was doing. Was that punk trying to touch her, or god forbid, kiss her?


Dorothy stumbled up the drive, barely making it to the front door before collapsing on the rough concrete, her clothes and hair in complete disarray. She rested her weary head on the hard door, when it suddenly opened, causing her to tumble forward.

“Jesus, Dottie,” she heard her brother say, but all she could do was grumble and lay there. She felt herself being lifted up into strong arms and carried inside the house. She knew she could count on her brother to take care of her, as he placed her in bed and tucked her in. He was always there when she needed him most, and she fell asleep instantly.

Garret wasn’t so calm, staring down at his little sister. Not only had she not come home by ten, she had not even come home by midnight. Instead, she had drunkenly stumbled up the front steps at two in the morning. She could barely walk, or speak. He wasn’t so mad that she had gotten drunk, he had been there before, he was mad thinking that she had no one to take care of her. Anything could have happened, and with the condition she was in, she would have been powerless to stop it.

Had something happened? Garret couldn’t help but wonder. He knew his little sister was a virgin, he had made sure to scare off anyone who would even think of taking advantage of her. He just hoped now that he hadn’t failed at keeping every man, except for himself, away from his Dorothy.


Dorothy stayed in bed the next day till way past noon, living off of ginger ale and Tylenol. She had only seen Garret once when he brought her supplies, and asked her if she was okay, if anything happened. She told him she was fine and he had left without another word. But by three o’clock, she felt good enough to venture out of her room and face Garret.

“Hi,” she hesitantly said to him. She braced herself for the yelling she knew would come, but was surprised when it didn’t.

“Hey,” he turned his attention back to the T.V. Why wasn’t he yelling at her? She wondered.

“Um, I’m really sorry for last night.” Was he really not mad? She couldn’t let herself believe it.

“Tell it to mom and dad.” Ah, there it is, she thought. He wasn’t going to yell at her, he was just going to threaten to tell mom and dad.

“Come on, Garret, rotterdam shemale you know you’re not going to tell them,” she said coaxingly as she slid over the back of the couch to sit next to him.

“Dorothy, you don’t know just how angry I am. You just wait and see what I’m going to do.”

Dorothy instinctively leaned away from him at the anger in his voice. He had turned to look at her, and she could see the temper burning in his eyes.

“Garret, come on. I’ll do anything.”

This is what Garret had been waiting for. He knew that she would try to bribe him out of telling their parents, and he had spent the night thinking of what the wanted her to do.

“Okay,” he said compliantly, “I won’t tell mom and dad, if you let me take pictures of you.”

Dorothy didn’t get it; she let him take pictures of her all the time. She noticed that the look in his eye had changed from one of anger to one of guilefulness. But she didn’t really have a choice but to go along with him, their parents would kill her for coming home drunk.

“Okay, fine.”

“Good, come up stairs.”

She followed him up to his room, where he shut the door and got his camera ready.

“Okay, take off your shirt,” he directed her.

“What!” she shouted.

“Yeah, the photos are going to be nude.”

Dorothy stared at him in disbelief; he wanted to take pictures of her naked?

“Absolutely not,” she said in anger, walking for the door.

“Fine, but then I’ll have to tell mom and dad.”

Dorothy seethed. Garret was being the biggest jerk. She ripped her shirt off and threw it at him, crossing her arms over her chest. She stood there glaring at him, and he snapped a picture.

“Try not to look so angry,” he told her, taking another picture, “loosen up, move a little.” Dottie swung her arms around her, and moved her torso a bit, for the most part acting like a wet noodle.

“Sit on the bed,” he commanded, “Get in the center, on your knees.” Dorothy scooted to the center of the bed like he asked.

“Now take off your bra,” Dorothy knew it was coming, but couldn’t stop the rage that consumed her. How dare he do this to her? “Dorothy, you’re just making this hard on yourself by not listening to me. The faster you do this, the faster it will be over.” Dorothy reached up behind her and unclipped her bra, letting it slide down her arms, before throwing it on the floor, too, next to her shirt.

Garret was standing behind her, so he couldn’t see her breasts, not yet anyway. He took a picture of the length of her back, the bones of her shoulders, the gentle curve of it, ending abruptly at the top of her shorts. “Turn your head and look at me,” was his next order. He was surprised at the fires of pure hatred boiling in her eyes.

He continued to take pictures, as he told her to lie down on her back. She reluctantly did as he asked, keeping her arms stiffly at her sides. He took pictures of her lying there, with bare breasts, and jean shorts on.

As soon as her breast became open to his gaze, her expression had changed slightly. There was still anger there, but there was now also pleading. She was incredibly embarrassed, he knew, but couldn’t stop. Her breasts were beautiful, he thought, and he had been waiting to see them for so long, and the rest of her for that matter, that he couldn’t stop now.

“Take off your shorts,” was his next command. She did so, lifting up her butt so she could remove them still lying down. “Stand up,” he told her, and when she did he said, “Now jump on the bed.” Dorothy jumped, and was incredibly mortified at the way her breasts bounced, knowing he could see it. Garret, however, loved the way they jiggled, and told her to continue jumping. Dorothy wondered if he was just trying to embarrass her by making her do this, but continued to jump anyway. She felt like she might cry as he continued to take pictures of her, his finger snapping away.

“Okay, lie back down,” he finally told her, and she was thankful that the jumping was over. He walked about the bed taking pictures of her at different angles, then telling her to turn over and lay on her stomach. She did, and more pictures were taken.

“I’m going to touch you, but trust me, okay?” Garret told her. He set his camera on the bed, and gently grabbed the top of her panties. He ever so slowly, started to pull it off her, her firm butt being revealed centimeter by tantalizing centimeter.

He stopped at her knees, leaving the panties there, taking some more pictures, before pulling them all the way off her. For some reason, Dorothy felt less embarrassed and exposed fully naked than she did just half naked.

“Now spread your legs a little wider apart.” She did, knowing all too well that her pussy was now open to his gaze. She could feel him taking pictures of her newly exposed flesh.

“Turn over,” he told her. She did and laid stiffly on the bed, as he took pictures. He told her to sit in various positions, to cover herself, uncover herself, stand up, lay down, blog shemale roll over. Finally he told her to lay down spread eagle for him.

When she did, and he was taking pictures of her pussy, her breasts, her body, She realized the full extent of what was happening at that moment. He was taking pictures of her completely naked, all her parts revealed to his eyes and to his camera. What was he going to do with these pictures? She knew he had to want them for something. Other people were going to see her body, her humiliation. She couldn’t stop a tear from rolling down her cheek at the thought.

Garret saw her tear and his hear cracked, he set his camera down, and walked over to her. He gently wiped the drop of moisture away with his thumb.

“You did really good, Dotty,” he told her gently.

“Are we done?” she asked hopefully. It had felt like hours.

“Yeah, sweetheart, we’re done.”

“Garret?” she asked hesitantly, too drained to move.

“Yeah baby?”

“What are you going to do with the pictures?”

She looked up at him with big, teary eyes, so frightened he wanted to expose her nakedness to the world.

He put his hands under her arms and pulled her onto his lap. “No one but me is going to see them, don’t worry,” he comforted her. She felt so good wrapped in his embrace, her naked body pressed intimately to his. He had never dared to dream that something like this would ever happen.

Garret was bracing her up with one arm, and he stroked her hair, shoulder, and arm with the other. He was surprised that she wasn’t protesting, she just lay there, pliant. He knew there was no way she could not feel his painful erection, but she didn’t say anything about it.

Dorothy liked being in his arms. She knew in the back of her mind that she should push him away and get dressed, but it just felt too good to have him hold her like that. He was her brother, her protector, she had never thought of him in a sexual way, but when he put his hand on her breast, that all changed.

She trusted him completely, and the way he was touching her felt good. She snuggled her face into his neck and pressed a soft kiss there.

Garret couldn’t believe that not only was she not struggling, she had just kissed him. He wanted to taste her sweet lips, so he put his hand behind her neck and positioned it so he could reach her mouth with his.

The kiss they shared was sweet and tender, then he deepened it. He probed her mouth with his, and she hesitantly matched his movements. He let his tongue slide between her lips, and she stroked it with her own.

Neither of them spoke, afraid to break the spell they were under. He moved her so she was lying back on the bed. He let his hands slide down her naked body, wanting to touch every wonderful part of her.

He cupped her breasts, and his heart swelled. Every tender inch of her was so dear to him. She was his. He then let his hand cradle her pussy, and she felt instant shivers at just having him touch her down there. He probed her tender folds with his fingers, feeling her soft, wetness.

Garret hopped off the bed and undressed as quickly as possible. He looked at Dorothy, and the desire he saw in her eyes was impossible to resist. He climbed on top of her, placing his hard cock at her entrance. Neither of them thought of the consequences, or that there was no turning back after this. They just felt their desire for each other, and Garret pushed into her.

He felt the resistance that was her maidenhead, and felt a sense of elation as he broke it. He was the first one to have her, and he would be the only one to have her, if he had anything to say about it.

Dorothy felt some mild discomfort as her virginity was taken, but the pain passed quickly. And she felt nothing but ecstasy at having Garret between her legs. They rose rapidly and fell rapidly from their climaxes, but were both extremely happy and satiated. Dorothy drifted off to sleep in Garret’s arms, but Garret stayed awake, luxuriating in the feel of his sister’s soft, supple body lying against him.

Though he loved her dearly, and he still felt like a bit of a heel for taking advantage of his younger sister in this way. Despite his feelings of guilt however, he couldn’t bring himself to regret what they had just done. He felt like his entire life had culminated to this very moment, this single instant in time. And he was elated.


Dorothy came slowly awake, feeling disoriented and strange. It took her a moment to realize that she was pressed against another body, a strong masculine body. She looked up and saw her brother’s sleeping face. He looked so adorable when he was sleeping, and she felt a complete peace like she had never felt before wash over her.

She pressed her body more intimately to his, and relaxed. Last night had been perfect, so loving, like a dream. But as Dorothy lay there, now in the harsh light of morning, she couldn’t stop her mind from thinking like she had last night.

This was her brother, and now he was her lover. She felt a nausea flow through her. Though what had happened last night felt right, she knew it was wrong. He was her brother, how could she have let this happen? What it someone found out? What if their parents found out?

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