I took my brother's friend's virginity

NSFWFirst Time

I’m (22f) a college student and home for the summer before senior year. My little brother is 19 and one of his friends (I’ll call him Jake) has had a crush on me for forever.

Three years ago (I was 19 and already in college and he was this skinny 16 year old still in HS) he sent me a this long DM about how he's had this mega crush on me for years, which I had kinda suspected. Super flattering but obviously he was way too young, my brothers friend, and honestly not really my type. But ive known him forever and let him down easy, and he took it really well and I got the feeling he just needed to tell me to get it off his chest. We chatted like once more a bit and then that was the end of it, other than he always likes anything I post on Instagram without fail lol.

This summer Ive been back in our hometown for summer break. He sent me a DM again out of nowhere a few weeks ago. We start chatting casually cause why not hes older and kinda cute now, and were getting to know each other better a little. He's also in college (he's a smarty pants and studying engineering). He's still on the skinny side but definitely started to fill into his body more and tells me how he's been working out a ton, but still no gf. He said it's mostly because he goes to an engineering school with very few girls at all. Eventually he tells me he’s still a virgin.

I've been a bit bored over the summer and not seeing anyone, and I'm a bit of a hornball but I don't like hooking up with total randos. I know him enough to know he's a sweet guy and not a creep. Also, I low key always wanted to be a guys first but I never have before. I offered to take his virginity if wanted. I’ve been kinda a tad slutty in college ngl, so I know what I’m doing and knew I'd probably be a much better first time for him than most. It took a bit to convince him I wasn't messing with him lol. Obviously he wanted to.

I knew my parents and my brother would be out of the house all day this past Saturday, so I invited him over. I wanted to see how excited I could get him so I answered the door in this little black see thru lace chemise I had. He turned bright red when he saw me it was super cute.

I could tell he was crazy nervous so I thought I should maybe slow it down a tad. I took him up to my room and we just sat on the bed talking and eventually he relaxed a little. Then I leaned in and kissed him. The second our lips touched his pants turned into a tent lol.

I helped him take his pants off and he had a nice cock. It wasn't huge or anything, but I dunno just nicer looking than most I've seen. He was very hard and already had a little precum at the tip. I just wanted to tease him a little and just ran my fingers gently along his cock and balls, but he immediately started cumming. He kinda panicked and was saying sorry, and i tried to at least finish him with my hand but it caught me off guard. Jake got super embarrassed and turned bright red. I rubbed his back and told him it was nothing to be embarrassed about and that I was actually really flattered at how excited he got for me. I told him that didn't count and we can keep going and he seemed relieved.

I asked if he wanted to try going down on me and he did. He was surprisingly good at it. At first he lapped at me like a dog which made me laugh but did actually feel good. I showed him how I like it (tracing little circles around my clit with the tip of the tounge gets me there) and he figured it out quickly, and he actually got me to orgasm.

He was already hard again, so I sucked his cock a little just so he could experience a blowjob, before I helped him put a condom on. I showed him how to do it right, leave some room at the end and pinch the tip before rolling it down. He was so excited it got me excited. I told him he could choose the first position and he asked for missionary. I lay back and spread open for him and the look on his face got me dripping. When he pushed inside of me his arms started trembling, and I've never felt sexier in my life. I pulled him close and let him fuck me how he wanted to with his face nuzzled against my neck.

I asked if he’d like to try fucking me doggy style and he did. I was surprised when he said he preferred missionary. He said he liked looking at my face because I'm so pretty, which made me want fuck his brains out lol.

I told him to lie on his back and got on top. I decided to make his first time a little more special so I asked if he wanted to see what I feel like without the condom. I don't normally fuck guys without condoms unless we're in a relationship, but I do prefer it like that, and knowing he's clean since hes never had sex before, I figured why not. His eyes lit up, but then he asked if that was safe. I explained I'm on birth control and I do get tested so it would be safe and he said yes right away.

I took the condom off and sank down onto him. I could tell right away he was not going to last long like this lol. He had this helpless look in his eyes when he looked up at me, and It just made me feel so hot and naughty. He tried to warn me he didn't think he could last long like this. I whispered in his ear he didn't need to last long, and started encouraging him to just let go and cum inside of me. That mad him start to cum pretty much on command lol. And it was A LOT, I could feel it.

Afterward he just stared at me with this dazed smitten look. Kept saying thank you and that it was better than anything he’d imagined and that he’d never forget it.

He’s been texting me almost every day since saying he can’t stop thinking about it. He knows I did this to help him out and we're not in a relationship, and I don't want to lead him on cause he is a really sweet guy. But I am already thinking about maybe inviting him over again one more time before I go back to school next week.

Idk if that makes me a good person or a terrible one. But it was honestly really hot.

Posted Aug 13, 2026, 4:57 PM UTC

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