Best friend's sister

[EltonC]

Scott’s house was right behind ours, so we hung out a lot. Irene was his older sister, around four years older than us. She really wanted to be a hippy chick and certainly dressed the part. Never wore a bra, commonly wore cotton tops that made the outline of her nipples quite visible, also would wear these oversize dashikis that would gap open when she bent over giving me a great view of her tits. I think she did this intentionally to tease me. It worked, I thought about the tits more than a few times while beating off.

Its the summer after my senior year of high school, I had been out of town for about six weeks, two on a family vacation, followed by a four week gig as a camp counselor. Gave Scott a call and he told me to come on over so I did. His bedroom was in the basement, so I would just go in the basement door and go over to his room. So I walked into his room and found myself face to face with Irene, wrapped in a bath towel. She asked me what I was doing in her room and I apologized and told her I didn’t know she and Scott had switched rooms.

She told me not to worry about it and dropped her towel to the floor. She came over and took my hand and walked me over to her bed, pulled my clothes off and had me lie down on my back. She knelt over me, mounted me and started fucking me hard and fast. I split time between kissing her and licking and sucking her nipples. I warned her to slow down because I was about to cum and she said don’t worry about it. After I came, she rolled over so I was on top, then reached into her bedside table and pulled out a vibrator and told me I could finish her with it. So I vibed her clit while feasting on her nipples until she told me she was done.

I had gotten hard again, so she took the vibrator from me and started rubbing it back and forth on my dick. It didn’t take to long for me to cum and she drained me all over her boobs. She grabbed her towel and wiped up the mess, then told me to get dressed. She warned me not to tell anyone, but its not like you can tell your friend you had fucked his sister. I would still see her over at Scott’s and I swear the teasing got even bolder. I decided to take in any view the would give me, screw the discreet glance down her blouse. Never hooked up with her again, unfortunately. My parents moved to a smaller house at the end of the summer, I went away to college and never saw her or Scott again.

[Gnome72141]

During college, my then-best friend called me and told me to drive to a hotel he was staying at with his family for winter break. I started the three-hour drive, just because I had nothing else to do.

I get to the hotel and found everyone at the pool...my friend and his sister (only 10.5 months apart, no joke, so we were all in college), his parents, and a family "uncle" figure. I walked alone to their hotel room, put on my swimsuit, then walked back to the pool. His sister's tiny bikini top on her enormous boobs was slipping a little, I was caught staring several times, and her mom kept telling her to adjust her top.

After swimming, my friend, his sister, and I walked back to the hotel room. While waiting for my friend to dig out the room key, I thought that maybe I would be daring and change clothes in front of his sister. It was worth a shot. I started getting hard in the hallway thinking about it.

We get into the room, and within 10 seconds I have my swimsuit off and I am totally naked. My friend said, "Gnome, my sister is here!" I said, "so?" and dried off with a towel while she was staring, and my friend took his swimsuit off, too (they shared a room at home their entire lives and and seen each other a million times, so this wasn't anything of note).

His sister said, "I would let you see me change but my mom would get mad if she finds out," (even though she was like 19-20yo), then she walked into the bathroom to change, which I thought was too bad. The bathroom had a sliding door, but she didn't close it all the way, so I moved to the side to see her. My friend said, "Gnome is trying to watch you!" and I heard her giggle. She leaned her head back to look out the door and stared at my totally hard cock now.

She untied her top, but she was juuuuuust inside the door enough that I just saw sideboob. And there was zero sag, even though she was at least a DD. It was unreal.

But then she closed the door the rest of the way to take her bottoms off.

She came out in a loooong t shirt to sleep in, clearly no bra, and possibly no panties, but I couldn't tell.

I was still naked because she was really fast and I literally couldn't find my own clothes. Their hotel room was a mess and I found them under the top of a suitcase, and I got dressed while she stared at me.

Then I ended up driving back to my college (why didn't I stay the night???? I don't remember why), and I remember jerking off to that evening for years to come.

[raysallx]

Long ago, my best friend, his sister (a nursing student) and another male friend drove down to Mexico. After an evening of drinking cerveza, we got back to the hotel. There were only two rooms, one with two beds and one with a single bed. It was decided (by whom? Not me) that I would sleep in the room with the sister. I was pretty shy in those days, but there was only one bed so we both jumped in. This sister was very cute and before long she was kissing me and we ended up fucking. I was pretty surprised by the entire situation, but she didn't act like it was a big deal. Nobody said anything the next day, sort of like it never happened. I wrote to her later and tried to get something going, and even though the sex was great, she lived far away and didn't seem interested, almost like it was an FWB thing, although FWB hadn't been invented yet.

[piecenick]

Growing up, my best friend's little sister was always trying to hang out with us, much to her brother's annoyance. I had no idea that she had such a crush on me until one of my sisters commented on it in front of everyone at the dinner table. I didn't know how a 16 y/o guy was supposed to deal with a 13 y/o girl, so I didn't, I just ignored her.

My friend her brother went in separate directions in HS, I was into sports, he wasn't, so we didn't spend as much time together, so I saw less of Deb, his sister. Fast forward a few years and when I was home from the summer my old friend gets in a car wreck and is has some pretty bad injuries. I go to the hospital to see him, and while his parents and sister are pretty shaken up, his injuries are not life threatening. I spend a lot of time talking to Deb and we decide to go out to grab a bite to eat and catch up on old times.

In a short lunch Deb confessed to her crush on me, I commented that she seems to have gotten over it, she gave me this smile and said "who said I'm over it". Deb was cute when she was little and she had grown even more attractive as an adult. I told her my way of handling her crush, she told me that she even wore short skirts and no panties to try to flash me and get my attention. Luckily I was house sitting for a friend, so Deb and I had a place to have some sexy times.

But by then end of the summer we had to go our separate ways.

[chuckfinly]

I lost my virginity to my best friend's older sister. I am 98% sure I have talked about it on here before. Their dad died and my family basically loaned me to their family (sounds worse than it is... I was not a slave) to work their ranch for the summer. My best friend's sister who was five years older than me was home from college and working the ranch too. My best friend got injured and his sister and I started spending a lot of time one on one working together mending fences and other ranch work. She was (and still is) hotter than Dante's inferno. I had a major crush on her. She initiated it (I was a very willing participant just to chicken to make the first move). Most of our encounters including the first were out under the open sky in the back country. Our first time was by a mountain lake we stopped at for lunch. She convinced me to go skinny dipping then it went from there. It was an amazing summer. We really never had a romantic connection. We were in very different stages of our lives. It was just fucking and scratching an itch. She was a great teacher. We fucked off and on for the next few years when we were in the same area... kind of a FWB type thing I guess. Eventually she got married and that put an end to that phase.

Her brother is still my best friend 25ish years later. I still see her several times a year at certain events and gatherings. Very few people know our history. My friend/her brother is one of them. We got in a fist fight over it when he found out. I told one other person. My wife doesn't even know though I think she suspects it she has never asked and I have never told her.

[mangomunkey]

Originally Posted by chuckfinly

I lost my virginity to my best friend's older sister. I am 98% sure I have talked about it on here before. Their dad died and my family basically loaned me to their family (sounds worse than it is... I was not a slave) to work their ranch for the summer. My best friend's sister who was five years older than me was home from college and working the ranch too. My best friend got injured and his sister and I started spending a lot of time one on one working together mending fences and other ranch work. She was (and still is) hotter than Dante's inferno. I had a major crush on her. She initiated it (I was a very willing participant just to chicken to make the first move). Most of our encounters including the first were out under the open sky in the back country. Our first time was by a mountain lake we stopped at for lunch. She convinced me to go skinny dipping then it went from there. It was an amazing summer. We really never had a romantic connection. We were in very different stages of our lives. It was just fucking and scratching an itch. She was a great teacher. We fucked off and on for the next few years when we were in the same area... kind of a FWB type thing I guess. Eventually she got married and that put an end to that phase.

Her brother is still my best friend 25ish years later. I still see her several times a year at certain events and gatherings. Very few people know our history. My friend/her brother is one of them. We got in a fist fight over it when he found out. I told one other person. My wife doesn't even know though I think she suspects it she has never asked and I have never told her.

Great story - can you recall more details of the first time?

[chuckfinly]

Originally Posted by mangomunkey

Great story - can you recall more details of the first time?

Yes I remember it like it was yesterday even though it was 25+ years ago. I will tell a more detailed story when I have time to type it out and do it justice. I really over simplified it above. We were eating lunch at the lake but we were camped out there for a couple days watching the herd because a bear had been killing calves. It started with skinny dipping after lunch, progressed to sunning on the rocks and some wondering hands, progressed to full on fucking later that day, if I tell the whole story it even has me running across a meadow by moonlight naked except for boots with a 110ish year old rifle and killing the bear. The funny part about that is I tanned the hide and made a bear skin rug which is now in my den. My wife knows I killed that bear that had been killing calves the summer I worked on my friend's family's ranch. What she doesn't know is that I killed that bear the same night I lost my virginity.

[fuzzylover]

Originally Posted by chuckfinly

The funny part about that is I tanned the hide and made a bear skin rug which is now in my den. My wife knows I killed that bear that had been killing calves the summer I worked on my friend's family's ranch. What she doesn't know is that I killed that bear the same night I lost my virginity.

Talk about snagging pelts in their youth🤣

[rudolfm]

Wonderful story Chuck.