This is my first attempt at a story so I'll appreciate any pointers to make the sequels better. Hope you like it. Disclaimer: there's a lot of Non-consent situations. Every character is over 18y/o.
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My name is Ty Thomas. I'm tall, blonde and toned; I have a visible six-pack and great biceps for my slim frame. I had a pretty great life until something changed everything on my senior year of high school.
It all started with a simple prank, and that got me tangled in a whole new life I didn't ask for and had me continuously asking myself 'How did I get here?'.
First of all, I am straight and have always been and had a pretty normal life, my family struggled a little with money at the time but other than that, I had good friends, I was popular, I played football and had good luck with girls. One day I was hanging at my friend Cory's place. He lived really close to school so sometimes we ditch classes to go play videogames at his house or chill and smoke weed before football practice. That's what we were doing this day, in fact.
His house was empty so in our high we decided it would be funny to go through his sister's stuff. We were goofing around with her clothes and acting like her. Anyways, we started going through her panties drawer and we found a buttplug.
"Hey Cory, look at this, your sister is kinky!" I said while holding the black buttplug in my hand.
He started giggling like crazy, mainly because of the weed. We were goofing around with it when he decided to dare me:
"I dare you to wear it throughout the practice." He said very defiantly.
"No way dude, are you nuts?" I responded pretty quickly.
"I'll give you 50 bucks." He said. Corey was pretty loaded so he always threw around money like it was no big deal.
Now, remember I said my family was struggling with money? I was lacking a little bit of it to go out with the guys or take girls out on dates; so when he offered I couldn't refuse.
So I agreed when he showed me the $50 bill right in front of me. I was so high it didn't sounded like such a bad idea.
"Alright, drop your shorts!" He said with a big grin. He thought it was the funniest thing ever.
We were both straight so it was no big deal, he had seen my ass countless times in the showers after practice. I drop my shorts exposing my white jockstrap I had on for practice and turned around a little. Now, I'd never had anything up my ass before so the experience of putting it in was very uncomfortable to say the least.
After a little bit of struggle and discomfort when he tried to put it in me, I asked him to stop. I looked through the drawer again and found a little bottle of lube and applied a few drops on the black toy. With that, Cory managed to place the buttplug inside me and just a black circle was out.
It felt really weird to have it in me, and I had to learn how to keep it in since my first impulse was to push it out.
So I put my shorts back on and we went to get our things to go to practice. I was already regreting my desicion but decided to go through with it since I didn't wanted the whole experience of putting it in to be for free.
"The whole practice, remember." Cory said before opening the door to get out of his house.
We went to practice and I could barely do the exercises since everything made the buttplug move and caused me discomfort. Plus I was really worried someone might notice the circle popping out through my shorts.
The coach definetly noticed I wasn't doing much and scolded me through the field, finally approaching me to ask me if anything was wrong. The coach was a 50 year-old, fat pervert to be honest. He had a lot of gray hairs, which he tried to cover with a cap; a mustache only pedophiles pull off, a big gut popping out the front of his body and was always spanking us in the ass during practice, which made all of us really uncomfortable.
