Lips Lickin' Lolli's For Money • Joshler One-Shot Stories

D.I.L.F (PART ONE)

Hi. I am okay. I'm publishing my drafts that have collected dust. They arent the best but, meh...

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Tyler always knew that he was away from the norm. His body was shaped to be attractive to the young boys  whose eyes lingered far too long. The slap of the ass in the hallways have become from him being surprised to shooting a wink at them.

He lost his virginity when he was sixteen, it was nothing like he thought it was. It was, weird honestly. As he laid back and allowed his boyfriend to press into him repeatedly. It wasn't that sparkle moment that was supposed to happen the night of prom.

After he broke up with him, claiming that it just didn't feel right, he moved on to try something different. He didn't know what this different was, but he knew that the little high school relationship was not for him. But he never ignored the ex whenever he came back begging on his knees. But after being with his ex and a few other boys in school, Tyler found some type of pleasure.

No, he never came, he took care of himself, knowing what he liked and disliked. Instead he found pleasure in pleasuring them. He found pleasure being used and watching as the boys above him or below him would groan and stiffen as they came. Their hot seed filling him and their face scrunched in pleasure.

As they toppled over onto the bed, off the couch, to the floor, etc. he would smile, watch their vulnerable face as they came from their high and remember it. He'd clean himself, go home and take care of his problem. So sadly no, he never came during sex, he wanted to know what it felt like, but bound to the day, as he touch himself, murmuring please, daddy, help me, he will never know of the unspoken pleasure.

Then he met, Anna, aka Annabelle. It was never Tyler's intention to sleep with Anna, not because she didn't have a dick, but more because of how closed in she was, plus she was a beacon to the eye no matter how hard she tried to stay invisible. Tyler's watched her from afar, her brunette hair streaked with different colors every three months, her glasses fitting her round face and bangs that swayed to the side.

The way her body was shaped and how she dressed herself made Tyler wish he had a body like hers, then he would be irresistible.

So, for his senior year, after watching the girl gain and lose friends, he went to talk to her, flapping his flannel and sticking up his chest.

It wasn't hard to befriend her, she was sweet, a fucking nerd that Tyler always beamed when she would rant about her favorite things, especially aliens. She had some weird fascinations, but it made her more likeable.

After a couple weeks, Anna heard some things and decided to come clean to Tyler.

"You're not trying to sleep with me, right?" Her soft spoken voice still hurt Tyler's feelings. Yes, he was known to be a bit of a whore, and slept with almost every guy in their school. Tyler thought she saw him differently, it was refreshing. Instead of being offended, he hugged her and told her how amazing she was and how happy their friendship had blossomed in such a short time.

Anna told him the same, giving him a sweet kiss on his cheek. No they never done anything together, instead, Tyler took her out in the fields where he found himself a lot. She would then talk about things people fears the most, apocalypse, invasions, life after death. But there was never a negative in those, it was something different, it was like positive acceptance that it will happen but everything is a loop.

She always talked about how our times always repeat itself, maybe because the only thing evolving is not human, instead the technology around us giving different ways of executions, deaths and genocide. She was the real that Tyler needed.