Hanging with Jake

Lily was sporting her new white skirt and a tight black crop top she had bought to go along with it. Her and Jake had planned to go on a bike ride along a nature trail just outside of their hometown before stopping somewhere downtown for some food. Jake was so far loving Lily’s new style choice. It fit her fun loving, happy go lucky attitude well, and the amount of skin was a nice bonus.

Jake rode behind her as they made their way up the hill. He glanced at her and noticed that the breeze was catching her skirt in such a way that it exposed her behind and the panties she was wearing underneath. A black cheeky lace number that he was quite familiar with at this point. He wondered if she knew, she didn’t wear clothes like this often so it could be a hazard she’s unaware of. Even still, he didn’t feel like telling her. At least not yet. He attempted to channel the rush of blood to his lower body into his legs so that he could climb the hill easier, but it was to no avail. He could feel his cock swelling ever so slightly, causing him to shift on his bicycle seat.

As the couple got to flat ground they passed dog walkers, hikers, other cyclists. Jake noticed how seemingly every single one crooked their head to watch as Lily rode by them. It excited him that they were seeing her like that but he wasn’t sure why. Still, he felt the need to tell her. He rode up next to her and motioned to pull to the side and stop. They passed a water bottle back and forth.

“You know babe,” Jake started, his two heads engaged in a bitter conflict “your skirt is kinda riding up. Doing a good Marilyn Monroe impression.”

Lily smiled and her face went red. “Oops” She laughed “are you enjoy the show at least?”

“Definitely,” He sighed in approval. Before he could continue and tell her that everyone else on the trail was enjoying the show too, she sped off.

“I’ll lead the way then!” She giggled, unaware.

He wanted to stop her again and tell her, but as he watched her skirt fly up and her ass sway as she pedaled he decided not to. He was only a man after all.

He wondered why he was enjoying seeing strangers sneak glances at her. He felt a bizarre sense of pride and amusement. As if to say “Yeah, she’s hot. And you know what? She’s all mine.” His thoughts went back to their time at the river, and the heat of their pleasure under watchful eyes. He had thought about it often during his sessions of solo fun. He wondered if she had too. He was overcome with a desire to show her off. He fantasized about fucking her in front of their friends, or picking skimpy outfits for her to wear. Sometimes, on the precipice of his release, when the thoughts have a tendency to become especially obscene and taboo, he would even picture his friends or strangers joining in. Assisting him in using and pleasuring his sweet and loving girlfriend. Those fantasies always seemed to disgust or scare him after he would blow his load. But they always seemed to draw the most intense orgasms, the biggest loads. And even with his post nut clarity, he would sometimes find his mind wandering back to them during the day. Much like right now. He had been envisioning a hiker catching up to them on one of their water breaks, flirting with Lily. Lily flirting back. Suddenly Lily’s skirt would be lifted as the stranger snapped his hips into her. Lily moaning around Jake’s own cock as she took him down her throat.

Jake slipped back to reality, looking down and noticing his hard on straining against his shorts. It was uncomfortable to ride like this but he couldn’t quiet it as Lily was still exposed in front of him. He simply had to power through.

It was made so much worse when they rode into town. It was early evening on a Saturday and downtown was quite lively. It was interesting how a midsized town could suddenly feel like a bustling metropolis on a weekend night. Jake was hyper aware of every look that Lily drew. She just pedaled happily, totally oblivious. Jake imagined that she would actually enjoy knowing that all these strangers were enjoying her, especially after their escapade at the river. But perhaps that was wishful thinking.

They arrived to their dinner spot. Jake had chosen a somewhat fancier seafood place as he wanted to treat Lily with how little time they had left together. Eventually his erection softened and he was able to enjoy Lily’s company.