Cum Fly With Me

Drew stood anxiously in the terminal, awaiting his first ever flight. He was 22, and just started his job as a junior IT consultant. Though his work was predominantly online, he was mandated to come to the company headquarters for a face to face meetup.

He had a late night shift and was visibly exhausted and sleep deprived.

He overcame his initial anxiety and completed the check-in process. Eventually he boarded the flight.

Dave was assigned a window seat in the last row. After getting comfortable, he looked at all the passengers finding their respective seats. There were a few pretty girls his age, but, to his disappointment, they sat in rows way ahead of his. The boarding seemed to have ended, but the two seats adjacent to him were empty.

Then at the very last moment, a woman entered. She strutted like a fashion model, attracting stares from the people seated ahead.

He observed her face more closely as she approached. She looked like she was in her mid-thirties and held a business magazine in her left hand. A handbag rested on her other shoulder.

She walked straight to Dave's row and placed her bag in the upper baggage cabin.

Dave couldn't stop staring at her cleavage through her white top, as she did this. She wore a black blazer and professional pants with white heels. After depositing her bag, she smiled at him before sitting adjacent to him in the middle seat, crossing her legs.

He realized for the first time that he had a thing for formally dressed women. Maybe it was because they seemed in complete control of their lives, unlike him.

The cleavage and the smile played wonders in his brain and his fantasies ran wild. He imagined her nude, in his bed, kissing him passionately, pulling him in, drowning his face in her large bosom. His dick twitched in his pants, and his face flushed.

As the 'fasten your seatbelt' sign lit up, he snapped out of his daydream.

Dave struggled and panicked a bit, not understanding the mechanics.

At this moment, the women asked with a sly smile, "First time?"

"Yes", he replied with a stutter.

She reached with her hands and fastened the belt, and her hand slightly brushed on his semi hard dick.

The flight took off but she still occupied his fantasies. After the plane stabilised, the signal came to take off the seat belts. He tucked and pulled at it for a while before looking at her. Her eyes were on him and she was almost laughing seeing his struggle. She reached out once again, though this time, she did it much more slowly, almost fondling his dick and grazing his thighs on her way back. He wondered whether he was imagining things.

He looked at her, but her eyes were already focused on him. Dave tried nervously to make small talk.

"Hi, I'm Dave."

"Cindy," she replied, almost disinterested.

She opened her magazine and started reading. Dave, now sure that he misinterpreted her actions, looked out through the window. The city disappeared slowly as the airplane cruised through the clouds. His fantasies disappeared as he pondered at the clouds over the reality of his existence, almost dozing off at a point. A quarter of an hour passed like this.

Suddenly Dave felt a small caress on his left thigh. Cindy was reading her magazine, but her hand rubbed his thighs, slowly making way to his inner thighs. By this time his heart was racing and his dick erect. Cindy smiled at the movement within his pants. She rubbed his hard dick on top of his pants, occasionally giving it a squeeze. Eventually she unbuttoned his pants and put her hands inside his boxers and pulled out his dick.

Dave was looking around frantically in panic. Here he was, with his dick out, being stroked by an older woman on his first ever flight. All of this seemed too surreal, yet the feelings were too pleasurable to tell Cindy to stop. He glanced around, checking if any passengers or cabin crew members were observing them.

She reached in, fondled his balls for a bit and stroked his dick. By this point his tip had a significant precum buildup. She rubbed her thumb on the tip and put it into her mouth and sucked on his precum. Amid the strokes, Cindy brought her face closer to Dave's. Her breath tingled his ears as the speed of her strokes increased.

"Close your eyes," she whispered. He complied.

She stroked faster, bringing him to the edge.

After realising he was close, she brought her mouth to his dick and sucked his tip. Then in one swooping motion, gobbled his entire length. The sensations were too much for him as he had the biggest release of his life, right into her mouth.

He opened his eyes in a daze. Cindy was still staring at her magazine, cross legged. As his panting decreased he looked at the stain developing in his pants. He couldn't believe it. It was too lucid and detailed to be a wet dream. From the corner of her eyes, she glanced at his wet stain and looked back at her magazine with a mischievous smile.