I’ve been reading this sub for a bit and finally decided to share. Sorry for the length, but I wanted to give all the details.
I was 23 at the time and back at my parent’s house visiting for a week. A friend of mine who I’ve known for years lives next door so I was hanging out over at his house a lot that week. His sister, who I’ll call Anna, is 3 years younger than us (20 yrs old) and was on spring break from her last year in college. I’ve known Anna for a long time, and we’ve always been friendly, but I never thought of her as anything other than my friend’s younger sister – until that week.
My friend has a pool so we were chilling out there, enjoying the sun, having some beers, when Anna came out wrapped in a towel. When she took it off I couldn’t help but check her out. I hadn’t seen her in probably 2 years, but she really grew into herself at college. She’s short, probably 5’3, dark hair, but was in incredible shape and had perky full tits that I hadn’t noticed in the past. She grabbed a beer and hung out with us, and immediately I felt a vibe – she was laughing at my jokes, playful touches, a lot of eye contact. Some thoughts went through my head, but I thought that’s all it would be.
The next day though I came back over to my friends house, and sure enough, as soon as I get there Anna comes down from her room to hang out with us. This time wearing a tight tank top and super short shorts. She kept staring at me while leaning over across the kitchen counter from me, giving me a great view of her tits and eventually made her way next to me and would occasionally brush up against me or touch my arm if she was laughing at something. My friend meanwhile didn’t seem to notice a thing. A few more buddies came over that afternoon, and we all hung out, drinking and grilling out into the evening, and Anna stayed with us the whole time. At one point she brought up the fact that we didn’t have each others phone numbers, so we exchanged them. At this point I really felt like something’s up, but I wasn’t gonna make a move at my friend’s house, and I didn’t want to misread the situation.
I walked back home next door a few hours later, kind of tipsy, and once I was back in my room I worked up the courage to feel it out. I sent her a text saying “sorry if I was super flirty with you all day” and she quickly texted me back “haha, don’t be sorry, I liked it” with a winky face. I swear I got hard right then. I got a little bolder and asked her what she was up to right now, and she said nothing, so I asked her if she wanted to hang out, and she said “definitely.” I couldn’t go over there and my family was home so didn’t want her to come over to mine, so I told her to sneak out to the end of her driveway and I’d pick her up in my car.
5 minutes later I drive over and she’s there with a smile on her face and a dirty look in her eyes. It was warm out so she was still in the tank top and jean shorts. She got in and we drove to the secluded dead end of a nearby street. As soon as I parked and looked over at her she was on me. Making out super hot and heavy, our hands were all over each other. I started kissing her neck, making her moan, and I fondled her tits over her shirt. We stopped for a second, both giggling slightly at how hot this whole situation was. She suggested we move to the back seat, so we both got out of the car and moved to the back.
Once in the back, Anna straddled me and took off her tank top, so I buried my face in her tits. I unclasped her bra so I could suck on her nipples which really drove her crazy. Being in the car, undressing was a little awkward, but we couldn’t get out of clothes fast enough.
I thought she had looked good in a bathing suit the day before, but she looked stunning without clothes on. Freshly shaved and tight in all the right places. She told me how badly she had wanted to go down on me all day and I said I had been thinking the same thing. She took me in her mouth while I reached over and put my fingers inside her. She was already soaking wet and she thrust her hips against my hand while giving me an incredible blow job.
After a bit I stopped her and told her to get on top of me, which she readily obeyed. I reached over to my pants to get a condom but she stopped me, saying she was on birth control and wanted to feel me raw inside her. She grabbed my cock and put me inside her, making us both gasp with pleasure. She rode me for a bit with one hand on my chest and one hand pushing on the roof of the car. It turns out she cums really easily on top, so after she had two shuddering orgasms I pushed her off me and made her bend over, both of us with one knee on the backseat and the other leg on the floor.
At this point the windows were totally fogged up and even though we were in a secluded place I’m sure anyone outside on this nice Summer night would have heard us. I proceeded to fuck Anna from behind and she immediately grabbed my hand and made me pull her hair. After a few minutes I knew I wasn’t going to be able to contain myself, so I told her I was going to cum and asked her where she wanted it. She told me she wanted me to cum in her mouth so she flipped around and took my cock super deep in her mouth. She was touching herself while I was fucking her face and finally I exploded. She kept jerking me off and swallowed every last drop, as though she couldn’t get enough.
We laid against each other in the back seat for a while longer, both catching our breath and caressing each other’s bodies, still in disbelief about what just happened. Eventually we got dressed and I drove her back to her house before I headed home next door. We ended up meeting up a few more nights that week, and would do the same whenever we were both home over the next couple of years until both of us ended up in relationships. It’s still some of the best sex I’ve ever had and her brother still has no idea.
Source: reddit.com/r/gonewildstories/comments/olr4kc/mf_the_first_time_i_fucked_my_friends_younger
Well done
Awesome.
Even if your friend knew, if he was a good older brother, he wouldn’t care. The way you described it, it was a good, consensual interaction. If I found out one of my sisters got some nice, consensual dick, I’d be congratulating them
This is her brother. I know. High five!
Tell us about the other times!
What kind of car was it?
It’s good her brother doesn’t know. I don’t know the reaction you might’ve gotten from your friend. Obviously if it was consensual he shouldn’t care if he ever finds out. I had consensual sex with my friend’s sister too alongside my brother and being straightforward I just told him. Mainly cos I wanted to piss him off since we had a brawl and weren’t on good terms. Showed him proof too and labeled it as revenge although it was nothing to do with her. I did feel like i used her but anyhow she enjoyed it. And ever since that happened he and his other friends are still after me. It’s been years and they still looking for me.
My sister is 18 months younger and we used to date one another’s friends a lot. It was a good way to screen for people and to use social pressure to keep them from being jerks during breakups. Plus, our friends blended anyway thanks to the close age. You probably should’ve told your friend/her brother; he probably wouldn’t care. It’s not lost on him that little sis’ isn’t so little anymore and he’d probably prefer she plays with people he knows and trusts than strangers.
She probably crushed on you starting in middle school but didn’t know how to proceed. Then she went off to college and got some sexual experience and confidence and Bam! There you go.
Good story, thanks for sharing.
The lengthy ones are always better, don’t worry about it 😉 Great read!
Yeah! 👌 Great story!🤩
Great story, and I bet she has had her eye on you, big brother’s friend, for a while, and you helped her fulfill a long time crush. It was very hot she wanted to feel you bare, and I hope you got to finish inside her in subsequent meetings.