Writing this as best I remember, some parts are stylized for sake of entertainment but are still true.
Going onto my third year of college, I had a summer job far from my student apartment so I subletted my apartment and lived with a friend’s family across the city. It was a really nice arrangement and I was very lucky to have a caring and generous friend. On the weekends, her and her mom would visit family so my other friends staying at my apartment would ask me to come visit or sleepover (that part was weird I know, but we were all close friends so it was fun. I often told them they could tell me to leave but I think they liked that I would clean while I visited and cooked.)
One of my friends, Shane, was subletting from one of our roommates that was in California for the summer. Shane was my age, 6’2, Indian, lean/muscular, and very much a pretty boy. He would model for the college fashion magazine and show every year. He often asked me questions about chores and his relationship, both things he was still new with. There were two moments that I think about still.
The first moment: I had worked for a sexual health organization that summer and everyday I would bring back something new: condoms, lube, dental dams, candy, shirts…etc. However, one day, Shane came to me and told me while trying to put on a condom I brought, it kept ripping, until he gave up. In my head, I was still in sexual health mode so I taught him the right way to put it on. I gave him a couple different sizes and told him to let me know which type to bring home. I told my other roommates to let me know as well if they needed any so none were wasted.
The next week, Shane asked me to come to his room to talk. After sitting on his bed and him closing the door. Shane whisper screamed to me that he was ripping the XL condoms. I asked if he was being too rough putting them on but he said no and that he felt they were too small for his girth. I had some XXL condoms in my bag that I had brought back home for another roommate so I gave him one. Before I could leave the room, he asked me to stay to see if he’s doing it right. He assured me it was just to be sure and to not get any ideas. I sat back down and looked at him as he hurriedly stroked his dick. I could tell he looked a bit embarrassed, ensuring me that it doesn’t take long but he feels weird. I was super horny at the time and found Shane very hot. I knew it was wrong but asked if I could just help quickly for the sake of time. He nodded and I spat onto my hand and stroked him.
Shane had told me about his dick before, saying that he was big but I always took it as him exaggerating like other guys. However, I was wrong. He was huge. His dick was at least 7 inches long and extremely thick all around, slightly curving to the left. He was uncut and shaven, with his big balls hanging full. I remember being a bit surprised but used both hands to stroke him. It didn’t take long for him to get hard. He tried on the XXL condom. I watched to check his way of putting it on but also in heat for his dick. After he did it, I took it off and showed him by putting it on him myself. Afterwards, we both cleaned up his room and I left to the living room.
The second moment: Shane and his girlfriend were struggling and had taken a break. Shane had blown up at our other friends so I was the only one left in the apartment to talk to him. I knocked on his door. It was close to the summer internship sessions end so he was packing to leave in a couple days. I asked to talk and he didn’t hesitate to accept. Shane and I were close and had just grown closer, going to hangout and eat, watching movies, talking about deep thoughts and sex. I sat in his bed with him while he cried and comforted him. We were able to talk until we got to a point of him calming down and going back to laughing at my jokes.
Shane confessed to me that he wasn’t able to use the condoms even thought they fit because his ex wasn’t able to take his dick since his head and shaft was extra girthy and hurt her even her mouth. I told him that someone else would be able to, it wasn’t the end of the world. I told him that I’d deepthroated bigger. Shane laughed but after moments of silence, he asked if I could try on him. I had a crush on Shane for so long that it took no time to be on my knees. I always thought he would never want to do this felt like a dream.
Shane undid his usual jeans and pulled down his boxers to a semi hard dick. His size was truly scary but in college, I always wanted to challenge myself. I remember him saying he didn’t like that his ex would only put her lips on his dick and not use her tongue. I asked him to let me know if it felt good or not. I started by exclusively using my tongue on his dick, spitting on it slowly and focusing on his tip, sucking on it and trailing my tongue around it. I wanted to prove I could take it so I started to force his dick down my mouth and into my throat. I really wanted to let him have the experience of being rough like he wanted to. I guided his hands on my head and on my ass since he liked big asses and his ex didn’t have one. He quickly got used to being rough and started to be verbal as well. He used my mouth at least three times, cumming down my throat then taking a break to lay together. When he first came, he loudly moaned and pushed my head down his shifter, choking me as my throat filed with salty cum. By the third time, he could barely cum.
We stayed friends for a bit but never talked about this as he returned with his ex for a year. After that, he dropped out mutual activities and stopped talking to me. I was always confused but it just seemed he was ready to make new friends and I wasn’t going to force anything.