Short Stories

My Sister the Escort

Jason jumped back on the bed, turned the TV on and called for room service on his phone. His gaze was pulled from his phone when he noticed his sister's naked silhouette behind the frosted door. "Wow" he said to himself, she had always been beautiful but she had grown even more so now she was older. He composes himself and orders drinks, lots of drinks. If they are going to forget about tonight they'll need the alcohol.

Tiffany steps out of the bathroom wearing his oversized shirt that makes it appear as though she is not wearing the shorts. She slumps down on the bed as the drinks arrive.

After 15 minutes of silence Jason turns to Tiffany "by the way. I'm sorry if Emily and I were ever too loud when we lived at home. She could be a screamer sometimes" Jason chuckled to himself. Tiffany took a big sip before she answered "can I tell you something? promise not to be mad or upset?", Jason looks at her concerned "of course" he answers. Tiffany takes a breath "I, kinda, used to masturbate when you guys fucked..." there's a silence "s-sorry what?" Jason says. Tiffany goes red, "yeah..." "why?" "Well it's hard to explain, but you're a very good looking guy, all my friends had a crush on you and would talk about your 'bulge' and well you kinda wore a lot of tight, grey track suit pants so I mean I saw the bulge every day. And porn was okay until it lost it's novelty and then I would hear you and Emily and it turned me on and... yeah" She looks at Jason who has a blank expression on his face, "J-Jason?" she asks.

Jason is starring into space, his whole world has been shattered. "You did what?" he asked, Tiffany went a shade of grey, fumbling over her words "p-please don't be mad, I'm sorry just forget it I shouldn't have said anything. Please Jason just forget it" she turned away and began breathing heavily as Jason stared off into space. "You used to.." Jason was cut off "I said drop it please" Tiffany spun around facing her brother who was starring at her.

There eye's locked as something seemed to take over Tiffany. She lunged forward wrapping her arms around Jason's neck kissing him passionately. His eyes widened with shock but he didn't pull away. Tiffany's lips were soft and supple. He closed his eyes and leaned into the kiss.

Jason leans closer as Tiffany's back lands slowly on the bed, she moves her hands up Jason's shirt removing it. Jason does the same to Tiffany revealing no bra and a fantastic set of breasts.

Jason's heart was pounding in his chest as he looked into Tiffany's eyes. He had always found his sister attractive, but never in a million years would he have thought that she would make a move on him. However, as she kissed him, he couldn't help but be turned on.

As they continued to kiss, Tiffany's hands started to wander. She reached up and grabbed Jason's hair, pulling his head closer to hers. Her other hand found its way to his waist, rubbing his stomach and moving lower. Jason's hands were also moving, exploring his sister's body. He couldn't believe what was happening, but he couldn't deny the desire that was building inside him.

Tiffany broke the kiss and looked into Jason's eyes again. "I've wanted to do this for a long time," she whispered. Jason swallowed hard, not sure how to respond. "I'm sorry," he said, his voice barely a whisper. Tiffany shook her head. "Don't be," she said, leaning in to kiss him again.

This time, their kiss was more urgent. Tiffany's hands moved faster, undoing Jason's belt and unzipping his pants. She reached inside and grabbed his erection, stroking it through his boxers. Jason moaned softly, his hands now exploring his sister's body even more aggressively.

Tiffany broke the kiss again, looking into Jason's eyes. "I want you inside me," she whispered. Jason's heart was racing, but he knew he couldn't resist his sister's desire. He pulled her shirt off, revealing her perfect breasts. He leaned down and took one in his mouth, sucking on her nipple as she moaned in pleasure.

Tiffany grabbed Jason's boxers and pulled them down, freeing his erection. She wrapped her hand around it, stroking it as she looked into his eyes. "I want you to fuck me, Jason," she whispered. He couldn't believe what he was hearing, but he couldn't deny the desire that was building inside him.

He positioned himself between Tiffany's legs, his erection poised at her entrance. He looked into her eyes, seeing the desire and need there. With a single thrust, he entered her, feeling her warmth surround him.

Tiffany moaned loudly as Jason began to fuck her. He moved inside her, his hips pumping harder and faster. She wrapped her legs around him, pulling him closer as she moaned his name.

Jason's heart was pounding as he fucked his sister. He couldn't believe what was happening, but he couldn't deny the pleasure that was building inside him. He knew it was wrong, but he couldn't help himself.

As they continued to fuck, Tiffany's moans grew louder and more desperate. She was close, and Jason could feel it. He thrust harder, wanting to make her cum.

Tiffany's moans reached a crescendo, and she cried out as she came. Jason felt her muscles clench around him, and he knew he was close as well. He thrust one last time, and he came inside her, filling her with his cum.

They lay there, panting heavily, as the reality of what they had just done settled in. Tiffany looked into Jason's eyes, her face a mix of shame and desire. "I'm sorry," she whispered.

Jason looked into her eyes, knowing that there was no turning back. "It's okay," he whispered. "We both needed this." They lay there, their bodies still connected, as they tried to process what had just happened.

Jason couldn't help but think about how things had changed between them. He had always seen Tiffany as his little sister, but now he saw her in a whole new light. He knew that what they had just done would change their relationship forever, but he couldn't deny the desire that was still burning inside him.

As they lay there, Jason reached over and grabbed Tiffany's hand, intertwining their fingers. He knew that what they had just done was wrong, but he also knew that he couldn't resist the desire that was still burning inside him. And as he looked into Tiffany's eyes, he knew that he would do it again.