All people mentioned in this story have their names changed and locations altered but otherwise the plot is true to my personal experiences. Everyone mentioned after the intro is a legal adult over the age of 18 nothing NSFW happens before that.
My story more or less begins my Junior year of high school. I wasn't a super attractive kid but definitely not ugly. I played two seasons of sports each year and had a decent body and muscle mass ratio, our overall class size was small so dating was drama filled and everyone knew everyone's business. I guess in hindsight it was a blessing I didn't really date in high school. Though college wouldn't be much better to come to find out.
Dad normally worked nights and my step mom spent more time smoking cigarettes than taking care of my step siblings. So while she was outside smoking, I'd occasionally sneak into their room and steal what I thought at the time was her panties and bras. Later, when we'd go to bed, I would try them on and occasionally jerk off while wearing them. It wasn't until a couple years later I found out they weren't my stepmoms.
As I mentioned before, in terms of dating, college wasn't much better. I had one FWB thing going with this black girl who lived off campus but she didn't want anything super serious which was fine for a while. Eventually we broke it off after finals had us occupied and we didn't have many chances to meet up.
Tinder was a waste of time, even if I swiped right on every single profile the only matches I'd get were the scammer bots. Eventually I turned my attention to the dreaded app MeetMe. Let me tell you, I thought Tinder was bad with its bots. But believe it or not, I did get a conversation going on MeetMe.
She was hispanic, living with family so she could only meet late at night. I let my dick do the thinking and agreed to see her.
I should have left when she texted me, telling me to come into her room through her window. All the lights were off except the TV, the room smells heavily of makeup products. She was already in some sexy lingerie, her hair was down and she kept her face turned away from me. She didn't want to kiss or make out, she wanted to get right to it. She bent over her bed and I stuck my cock in her, grabbing her waist. Once I got a rhythm going I reached to grab her breasts to squeeze and massage them.
After her repeatedly moaning "oh papi", I decided to reach under and rub her clit while I was fucking her. When I slid my hand under her lingerie to start rubbing I felt it. I felt her hard cock pressed tightly against her from the panties.
I should of froze or pulled out or something, but I kept fucking her. How did I not realize it? Well one, it's because I had very little sexual experience at the time and two, I later learned it was because she had so much lube and had stretched herself out with a dildo before I got there so I would just slip in and not think anything of it.
Either way, I eventually filled "her" ass with my cum and promptly left, more embarrassed than anything.
A couple thought filled days went by. Questioning my own sexuality and whether I actually enjoyed that encounter. When my dorm-mates asked why I was out so late that night I just told them I was out at billiards hall with some upperclassmen I met.
After about two weeks of fighting with myself I came to the only logical conclusion I could manifest. I had to hook up with another guy and determine if I actually was gay or not. But I wanted to do so discreetly. So I made a new profile on MeetMe, changed my name and picture and started talking to guys.
Most of them were actually pretty respectful, acknowledging it was my first time, and that I was questioning my sexuality. I got to talking to this latino guy, Joseph, who lived on his own, and he offered to start slow and give me a blowjob and if I felt comfortable I could reciprocate. I did tell him this would be a one time thing up front since I didn't know what I wanted and could easily ghost him if I got embarrassed. Which he understood completely.
We set a time to meet at his place. I probably sat in my car for a good five to ten minutes contemplating leaving.
"I have to do this." I told myself.
I steeled my nerves and went to knock on his door. He wasn't much older than me and his place was minimally furnished but that didn't bother me any. He showed me to his bed, and offered for me to lay down and relax. He stepped out of the room which made me feel a little bit calmer.
After a few minutes, he poked his head in and asked, "Are you ready?"
I shimmied my jeans and boxers off and nodded to him. I laid with my hips at the edge of the bed so he could kneel down and wrap his mouth around my cock. And he did so gingerly, I couldn't help but gasp initially.
"Why did it feel so good? Why was he better than the other girl I was fwb with?" I kept asking myself.
I instinctively grabbed the back of his head, lightly gasping and moaning. He was gaining speed, sucking harder and faster until I eventually came in his mouth. After he sucked every drop out of me he stood up and spit in a nearby trash bin.
"How was that?" he asked.
My mind was racing, almost missing the question. Don't get me wrong it was great, but my mind flooded calling myself a f*g amongst other things.
"It was great." I replied and gave a quick smile before putting my pants on.
"Do you want to give it a try?" He asked.
