From Mentor to Big Brother

Chapter 5

I know you guys have been waiting for a while, and I do apologize for that, it’s been quite busy these days with work and life in general. But I didn’t forget about you. So here it goes. This happened in September and I can’t wait to share the rest with you



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Our nights stayed within the same vibes, somehow planning for a drink, a dinner or an outing and we end up in my apartment doing the same thing. Drinking, massages, and sleeping next to each other. Not to mention the occasional happy endings that wouldn’t occur as much as I wanted them to but still someone with hint it out and it would happen.



What surprises me is that in day to day life, we do not discuss this topic. He goes on about his day, he has his own group of the most straight guy vibe I’ve seen doing their random shit and being guys. I hear all about the stories as he’s either texting me about it or when I see him.



Our situationship at this point has been an on and off one. Either I see him a lot or I don’t see him for months. It doesn’t bother me and I do just take it for what it is.



On a random Tuesday night he texts me about a stand up comedian we were watching one of the nights and the conversation continues. Then he dropped the “where you’ve been haven’t seen you in a while” and I say what I always say “you’ve got my number and you know where I live, drop by anytime”. He said “how about tonight? Maybe I can come over and hang?” I responded “sure just let me know when”



A couple of hours later he texted me saying he forgot about some gathering he’s going to and he won’t be long but he wants to see me tonight.



Around 10 pm I got a text from him saying “is it too late to come?” I said “not really, but if you’ve got school tomorrow I believe you won’t be hanging for long”. He said “well, maybe I’ll just sleep over and go to class from your house”



I responded “sure we’ll make sure you get your 8 hours of sleep somehow haha” and then he responded with what just made me giggle and got me anxious a bit, he said “ I don’t think we’ll sleep, maybe I wouldn’t want to sleep. Maybe I won’t let you either”



I didn’t know how to take that, but as always I’d leave the ball in his court and I wouldn’t want to have any expectations.



Night time came, he texted me around 10:30 saying he’s leaving the gathering and if it’s still cool if he comes. I said yes.



Door knocked, I got excited. I opened the door and there he was, oversized jeans, and a black t-shirt. Something about him was different. Not sure if it’s the workouts he’s been doing with the boys or his vibe but I let it slide.



He said hello and he walked in. We had a small talk, he told me about the outing and this girl who he’s into that came there and they had their flirting moment with, he started showing me the texts and IG messages they send each other and I was happy that I wasn’t too bothered by it. It was kind of a turn on.



Then i said “so you told her that you’ve got to end the night quickly because you want to come see your big bro?” He said “nah, I wanted to see my big bro because I’ve missed him” and he gave me a hug.



I could smell him, a bit of sweat and a bit of cologne. Perfect combination to get me turned on.



We had a couple of drinks in the living room, I didn’t want to hint at anything. Then he randomly took off his shoes and socks, then his T-shirt and he started asking me if I see any progress. I was pretty surprised he’s pumped like that. He said he’s been working out pretty regularly with the boys. And that he’s pretty sore, but the good kind of sore.



I didn’t give in or say anything about it, instead I asked if he wanted another drink. He said “nah can we go chill on your bed instead? I could use your hands tonight”



“My hands? For what exactly?” He laughed and said “a massage I promise, I would kill for one right now from you”



“Fine fine I’ll just give you a massage then” I said. “Well you know if I ask for anything else I’d convince you to do it” “sure whatever you say”.

He smirked and said “well I don’t just come see you because of that, I hope you know. But I truly love hanging out with you and being with you” I said “I know I know get to bed”



Our massage routine was the usual, I did his body first, then he did mine. We were both in our underwear just hanging on the bed. Then he said “get closer, get cozy next to me” and I moved a bit closer until I was inches away from his body. Until he moved his hand around me, and pulled me to his chest, then he said “ahh better”



So I was in a position on my side while he’s on his back, my hands on his chest and my legs on his body. I was cuddling onto him, which I didn’t mind.



We talked a bit and I started caressing his chest and belly with my hand. I’d make the occasional trip to his nipples and I could feel that he enjoys it.



He broke the silence after a while and said “lower” and I took the hint but refused and said “not tonight”. He made a sad face and I laughed. He said “please” and I said no. He said, aren’t you comfortable with me? I nodded. He continued, well maybe we get to try things my way, and I want to try a few things and if things gets uncomfortable for you just let me know how about that?



I freaked out internally and didn’t know what exactly does he mean by that. So I asked him”what do you mean?”



He said, just trust me, and once you feel like you think it’s too much we will stop and never talk about it again.



I was thinking about so many scenarios in my head, and I was getting more anxious. Still I said “sure”



He said “but just so you know, I’ll take the lead this time, at my own pace”. Again I just said “sure thing”



He went from a cute puppy eyed face to a more dominant one somehow and he said “lower”



I lowered my hand a bit until I reached the top of his briefs, I slid my hand inside and I felt his hard rock dick. I grabbed it and started slowly massaging it and jerking him off.



His hands are still allover me holding me tightly and my body on his side as I’m jerking him off.



Then he took his hand closer to my face, pulled it closer to his chest and arm pits, I felt his fingers crawling on my face and then he placed in his fingers on my lips as I was jerking him off still and whispered “open”



With still an open mind to this experience I opened my mouth and he placed a finger inside my mouth, then two fingers. I was automatically sucking on them as he discovered my mouth with his fingers and still holding me tightly in place.



He was using his fingers as a hook inside my mouth as I was drooling a little being held closer to his body and I’m still jerking his dick. I felt like I was completely under his control.



He moaned a little and then after a while he flipped me on my back. Took his fingers out of my mouth. He slid down my briefs, grabbed my dick and started jerking me off for a change. He got up to his knees jerking me off with one hand and another hand he went back to sliding his fingers in my mouth.



I never understood sucking on fingers during sex but somehow this made me feel like I was being dominated and I enjoyed it a lot.



He shoved his fingers deeper and I took 2 of them while having tears in my eyes, hoping I wouldn’t gag. Then he did the unthinkable, he went down and sucked my dick.



My mind was allover the place. His fingers in my mouth, my dick is in his mouth and he was going at it like a pro but also like somehow who didn’t do this before.



I could sense the dominance but also sense the inexperienced aspect as well.



He got my dick wet, a little too wet and saliva was drooling everywhere. He jerked me off with this hand while sucking me, then he slid his hand down to my ass crack and placed a finger on my hole. He started rubbing it, getting it pretty wet form his spit, then he took my dick out of his mouth, looked me in the eye as his fingers were in my mouth and he slid his finger inside me as flinched. He held me in place with the fingers in my mouth as he pushed his finger deeper into me. All the way in.



I felt like a pig on a spit roast just being filled from both holes, but yet again i still let it be because somehow I know he’s not using me for what it is but we do have a genuine friendship behind all of this.



I spread my legs open for him to know it’s okay, he kept fingering my hole, then he used a second finger. When he found that it was tight, he took his fingers out of my mouth and used those fingers to finger me a bit since they were wet.



Then he went back to laying down on his back, got me closer and said “now go low”

I took his dick in my hand, I got my head lower.



I could smell his dick, it was sweaty a bit but all in the right way. I got excited even more, I held his thick shaft in my hand and I tasted the tip with my tongue for the first time and he moaned.



I sucked on the tip for a bit and then started going a bit lower. I couldn’t get the whole thing in my mouth it was pretty big and thick, but I sucked him slowly as much as I could, I took it out of my mouth, I licked it a bit running my tongue allover his dick and then went to his balls and sucked on them. He wasn’t expecting that since he was moaning loud.



I got up and went between his legs, I spread them and went down on his dick, balls, and the occasional thighs kissing.



He didn’t say anything he was just moaning softly with a deep voice. I sucked some more while jerking him off and then he moved his feet on my back and pushed me deeper into his dick, and his hand was holding my head in place and then he started to face fuck me slowly trying to get it to fit inside my mouth even more.



I could sense his body starting to sweat and his movement was happening in a sense of pleasure, I kept sucking him deeper and harder until I felt he was about to cum. I didn’t know what to do then since he started moaning Harder.



I tried to take my mouth off from his dick but he shoved it back in and held me tightly as he started face fucking me.



He moaned hard, his body was twitching and he held me tighter in place with his hand and his leg on my back. and then I felt it in my mouth. He started cumming and he moaned “swallow” and I obeyed.



There was a lot of cum and I tried my best to swallow as much as I could. But some was dripping out of my mouth.



After 6 or 7 shots of cum he calmed down and he was breathing heavily. I took my mouth off his dick and held it in my hand jerking what’s left of his cum out of his dick. Then I saw him looking at me with that dominant face, and he took his fingers and swooped the cum from my lips and shoved them back into my mouth and he fed me all the cum that was leaking. Until his dick was cleaned somehow.

All of this and I forgot to even jerk off at the same time, all I was focused on was his needs at that moment and I forgot to please myself and cum at the same time.



After all this was done he laughed a bit and I laughed to break the tension. He said come up here, and I did. He held me tight back to his chest but this time he was sweating and I loved it. He asked “was this okay?” I said “yeah it was an experience, we did”



He paused for a second and said “we did? I’m not done and this is just the warmup. You didnt get to finish and I wouldn’t want that now”