Drake had dropped out of college before, but at 27, he wanted to give it another and he knew now would be perfect as he could room with his younger sister, Tiffinay, in her second year and had her own place.  His friends did think it was weird, rooming with his sister.

John, asked him one night. “It’s weird. What if you catch her with another guy or naked by accident?”

Drake hadn’t considered that but didn’t think it would be a problem, as he didn’t think Tiffiany was sexually active and the whole catching you in the shower only happened in pornos. He thought to himself. A thought he’d soon come to realise was wrong.

Two days into his stay, he first heard it. Faint moaning coming from the other side of his wall. At first, he thought it was just something Tiffany was watching way too loud, and ignored it. Only he began to hear the same moans every night until it all clicked into place when he bumped into her latest conquest coming out of their shared bathroom.  For the past two weeks, he’d been hearing his sister moan as she climaxed to a handful of guys.  

He didn’t know if she knew the walls were that thin, and he wasn’t sure how to bring it up, so he didn’t. Instead, he just listened and, after realizing it was moans of pleasure, began to find himself turned on. Before long, he found himself with a semi that brought him back to reality.

“Am I really getting turned on hearing my sister getting fucked?” He thought to himself.

He left the room and the house in that moment, fearing what he’d do if he continued listening. He decided he needed to take his mind off his sister and onto someone it wasn’t weird to fantasise about.  That’s when he thought back to what John had asked him before he left for college and cursed him.  He couldn’t believe he was right, even though Drake knew he’d never tell him that.  He headed to the local bar and hoped he could drink enough to forget why he was drinking.

#

In the bar, he started off with the strong stuff; whiskey, no ic,e and told the barman to keep them coming. As he downed the glasses, getting drunk and forgetting why he needed to drink, he loosened up, taking notice of the blonde sitting across from him, who he knew had been staring at him for the past ten minutes.

Filled with liquid confidence, he staggered over to the empty chair beside her.

“This seat taken?” He asked.

“I was wondering when you’d come over. I’m Pheobe," she said, gesturing for him to sit.

The two of them flirted for the next few hours, exchanging stories of their very different college experiences until she leaned over and whispered in his ear.

“I’m not wearing any underwear, you wanna feel?”

She took his left hand and guided it under the table and over her leggings, where he could feel her lips separated from him by a thin piece of fabric. He’d never rubbed a woman’s pussy in public with the danger of getting caught adding to the excitement. He continued to play with her until her face couldn’t hide her pleasure anymore.

She grabbed his arm to stop him and whispered, “Let’s finish this in my room, and I can repay the favor.” Her eyes glanced down at the bulge in my pants. 

He followed her out when a thought danced around in his head. He was about to finger a beautiful blonde with ample breasts, partly due to his sister.

#

The thought stuck with him as he got back to her place. She wasted no time as he slipped off her leggings revealing her perfectly pear-shaped arse. As she bent down to remove the leggings, he reached over and squeezed, curious to know if it was as soft as it looked. It was and as he squeezed his fingers slide over to her pussy as he started to rub her clitoris. As he stimulated her getting her wet, he tried to focus on her, but images of his sister would flash before him as he imagined it was her he was fingering.

He stopped for a moment, confused as he tried to process the way his mind was working. He had only heard Tiffany orgasm. That wasn’t enough to think about her sexually, he thought to himself. Here was a beautiful woman, he should be focused on, one who didn’t mind his stop-start nature, equating it to foreplay.

“Don’t stop, I’m so wet, I need your fingers in me,” she teased.

Drake obliged as he played with her clitoris with his thumb, rubbing it in circular motions, as with his right hand, inserted two fingers, slowly penetrating her. She let out an audible gasp as he continued getting faster, as he could feel his fingers getting sticky as she arched her back and her walls contracted around them, gripping them tight. He knew she was close to orgasming, so he fingered her fast and hard until she screamed in ecstasy and squirted all over his hand.

She trembled in pleasure as he licked his fingers, tasting her for the first time that night.  He knew she was ready for his cock he’d had felt how lubricated she was on his hand, only he wasn’t ready for her.

He couldn’t understand it—he was fingering a beauty, and normally it would be so hard it hurt pressing against his pants. Only he was standing at half-mass as though there was an invisible barrier preventing him from getting hard. He didn’t want her to notice, so he got on his knees and buried his tongue in her lubricated snatch.

As his tongue licks her clitoris, stimulating her again, his mind drifted to his problem between his pants. He couldn’t understand it as he had gotten hard recently and over less, and that’s when she appeared in his mind – Tiffinay.

The thought of her changed his night around as he could feel the front of his pants getting tight to the point, he had to unbutton them as his tongue was still deep in her pussy. That’s when he knew he couldn’t escape the feelings he’d developed for his sister. He used that motivation to keep himself hard as he put his cock to work slowly penetrating her pussy before he took full control of the situation pounding her pussy until she was a quivering wreck of orgasms and all he thought about was what if this was Tiffany. 

#

After he showered, he left her place and headed home more confused than ever. He’s just had some of the best sex of his life, yet the only way to do that was the think of his sister, whom he hadn’t even seen naked. He had no idea what he was going to do, as who could he tell about this. He was alone with a problem destined to be kept a secret, as even if he did tell someone, he just knew it would get back to Tiffany and make things 100 times more awkward.  

He kept thinking of solutions as he walked home, getting caught up that he entered his house in a daze, transfixed on a thought, forgetting his surroundings. That was until he walked past his sister’s room, and a sound broke his train of thought.

“OOH AAH” Tiffany moaned.

Drake turned to the direction of the moan to see that her door was slightly open with a gap big enough for him to see inside. As he peeked, he saw Tiffinay naked on her bed with a dildo as she fucked herself with a passion he hadn’t seen before.

To Be Continued