My female best friend (Rebecca) and I have been close friends since middle school, we’re both 21 and are still close friends. I know her family very well and her younger brother (Alex) is always there when I try to hang out with his sister. Both of them know I’m bisexual and don’t care much about but Alex has been texting me about my sexuality lately. Alex is 14 years old, short for a boy (4’9, but I can’t say much cause I’m also short for a guy), and he’s also athletic and play soccer for his school. This story actually takes place very recently and I’ve been getting to see Alex’s true self.
So on August 29th, Rebecca, her friends, Alex and I went to a concert. Rebecca and her friends were somewhere else and Alex and I were together since we had floor tickets. At the concert, Alex asked me how it feels dating a guy which felt awkward at first. I told him, “That’s a weird question to ask but it feels normal dating a guy. Why?” “Well I’ve been getting framed as a gay boy at school lately because the boys at school say that short boys are always gay,” Alex told me. I proceeded to tell him to just ignore them because they’re jerks and he gots my number to text me whenever.
While the concert was happening a specific love song was being performed and both of us were vibing to it. “I have been thinking if I’m gay or not for a while now,” Alex shouted. I ignored him as I was trying to vibe to the song. After the concert was over and dropping everyone off at their designated places I decided to text Alex. “Hey Alex are you still awake? I want to talk with you,” I texted him.
“I’m still up hi,” he replied instantly.
“You told me that you’ve been thinking about being gay or not,” I asked.
“Well not really but ever since school started again I always feel like I might be gay because of the things classmates and students tell me,” Alex replied.
“Like what exactly do they say to you because I didn’t realize I was bisexual until my senior year of high school and you still have a lot left before you finish school,” I said.
“One specific kid always tells me that I should go after boys since I don’t have a masculine body,” he replied. Alex does in fact don’t have a very masculine body. I personally see him as a femboy since he has a slim body but has a bit of muscle because he plays sports.
“Well that not always the case. Look at me, I look masculine but I’m bisexual and I like a couple of guys,” I told him.
“And how does it feel liking another guy though? Does it feel weird being in public with a guy knowing you’re dating him,” he asked.
“To me it doesn’t feel weird because I’m very open about my sexuality and I tend to let every new person I meet know right away about my sexuality. But you’re still young and still haven’t figured it out yet to really know if you’re gay or not,” I said. After that he was just telling me how my close people felt about me coming out as a bisexual man. I told him that the only respect I’ve lost was from my dad but he shouldn’t compare himself to me because not everyone has the same feelings towards gay/bi people. He then proceeds to bring up sex.
“Does it hurt getting fucked 🙃😅” he texted me.
“You want to find out 😈,” I jokingly replied.
“Idk I’m scared to try it,” he responded.
“Oh I was just kidding about that,” I replied. He then left me on read for the rest of the night.
The next day, the day was going by fast and good. As I’m getting off work Rebecca calls me and asks if I can get Alex from school since everyone from her family is still working. I told her that I can and started heading to Alex’s school which luckily isn’t that far from where I work. When I got the school and picked up Alex, he pointed out the student that’s always telling him that he’s gay. At first glance I don’t know why he’s picking on Alex if he looks more feminine than Alex. I told Alex he’s prolly only framing you because he’s actually gay and knows you wouldn’t do nothing to him.
When we got to his house, I decided to stay for a while or until someone arrived home. “Did you actually meant what you told me last night through text,” Alex asked. “It was just a joke please don’t tell your sister,” I said. “Oh no, this is a you and me thing only. I was just saying because I actually thought you were willing to do it,” he said to me. “Do what? Fuck you as in having sex with you,” I questioned him. He said yes and told me that he’s willing to letting me fuck him.
“You’re only 14 years old though,” I said. “I don’t care and no one would ever know about it,” he said. So I gave in and I pulled him up to my chest, getting him to sit on my lap. I kiss him on the lips in which he didn’t resist and kissed me back. I started to take his shirt off and rub his nipples, making them get hard. We go to him room where he pulls his pants down, gets on his bed, and gets on all fours facing away from me. Seeing a young 14 year old bare hole is so hard to believe. But my own uncle raped me when I was only 15.
I take his shoes and socks off and take the rest of his pants and boxers off. Getting him completely naked. “Now you relax your ass hole and let me please you,” I told him. He didn’t say anything, which made me know he was nervous so I stopped talking and started caressing his ass and spreading his cheeks to unveil his very tight and cute pink hole. I spit on it and he giggles softly. I started licking his hole gently and slowly just to try and get him to relax. “Mmmm, this feels good,” Alex said softly. I proceed to shove my tongue deeper in his hole gently which made him moan pull away from me.
“Did I hurt you I’m sorry,” I said. “No no, you didn’t I don’t why I reacted like that,” he replied. So I continued to lick and spit on his hole for 6 minutes. After that I got naked and luckily for him I have an average 5.8 inch dick which isn’t that painful for a first time. I turn him on his back and started to suck his dick. He has a cute small dick (about 3 inches, he hasn’t hit puberty yet). He moans loud and tells me he never felt this kind of pleasure on his dick. I continue sucking until he busts in my mouth. “Did you like that,” I asked him. He nods as I clean his dick. I get him to the edge of the bed in missionary position.
“If you enjoy this part a lot then you’re going to be gay or bisexual. That’s what my first time told me and he was right,” I told Alex. “Is it going to hurt a lot,” he said. I was straight up honest and told him yes but that the pain won’t hurt as much if he relaxes his hole and a lot of lube is used which we did use. After putting a lot of lube on his hole and on my dick I slowly started penetrating him. He starts whining a bit but not loud so I stop and get him to catch his breath. I tell him that he’s doing good at relaxing. As restart on penetrating him, this time I slide in easily and he moans loudly.
“Good boy Alex I’m inside you now,” I tell him as I begin thrusting my hips back and forth. Alex has a bit of trouble trying to speak but his moaning is telling me that he’s liking it. I pull his feet up to my face and suck his toes. “I lost my virginity to my sister’s guy best friend can you believe that,” Alex says as he rubs his feet against my face. I start pounding him a bit harder but he begs me to slow down, so I did. “Do you like this Alex,” I tell him. “It feels better than I was expecting it to feel like and maybe I could turn out to be like you and like boys and girls,” he told me.
I proceeded to fuck Alex for 5 more minutes before I pulled out and had him suck me off until I finished in his mouth. I made sure he swallowed my load which he confirmed to me that sucking dick isn’t really that exciting for him. But that’s what my best friend’s brother and I did. Would I do it with him again, yes but when he’s 18 and older. The only time I’ll do it with him when he’s 17 or younger is if he’s the one who offered to have sex.
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