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🤣

[chuckfinly]

I was spending the the summer working for my best friend's family ranch after his dad died unexpectedly and they needed the help. My family basically loaned me to his family. My dad dropped my horse and I off the day after school got out and I did not hear from my family for almost three months. I had my horse, my saddle, my rifle, my rope, my knife, and some clothes. He had a super hot older sister who was home for the summer from college and also working on the ranch. I had a crush on her for years.

When we were out checking fences we found freshly killed calves we determined based on foot prints and scat were killed by bears. Grizzly bears have long been extinct in California and it is not very common for black bears to kill cattle. When they develop a taste for them though, it is a problem. We went back to the ranch house and told my friend's mom about the kills and she sent us up to camp out and watch over the cattle until I killed the bear. At this point there had been some flirting between my friend's sister and I and she had kissed me a week or so earlier but nothing had gone farther. It is also worth mentioning that my friend had been injured in a ranching accident a couple weeks earlier as well which is why his sister "B" we will call her and I were spending so much time alone when he normally would have been with me or with us. Anyway back to the story, by that time it was too late in the day to ride back out to the herd so we decided to take the risk of another kill and ride out at first light. We packed our saddle bags with several days worth of gear that night so we would be ready.

In the morning we saddled our horses, grabbed our rifles and set off. Now I still remember some details about the day and setting you probably are not interested in but I am going to throw them in there because they are part of the experience and part of what makes back country fucking a kink for me to this day I believe. I remember the early morning air was crisp and cool, a welcome relief from the heat of the valley. As we rode higher, the views became more breathtaking. The meadow pasture where the bear had been killing calves was next to a mountain lake was surrounded by wildflowers of all colors, and the mountains in the distance were still snow-capped. We picked a spot to set up camp that was sheltered by some trees, but still had a clear view of the lake and the meadow so we could watch the cattle. B and I worked together to set up the tent and build a fire pit. We gathered some firewood and started a fire. I am not sure why we started a fire early in the day, it just seemed like part of setting up camp... Plus she wanted coffee which we made over the fire so maybe that was it. We then unpacked our saddle bags and set up those umbrella type camp chairs by the fire.

As we sat by the fire, we took in the stunning view in front of us. The lake was crystal clear. The mountains were majestic, and I felt small in comparison. The sky was so clear. We sat there in silence for a while, just enjoying the beauty around us. As the day wore on, we explored the area around the lake, taking in the stunning views and the wildlife. We saw deer and other wildlife. The sun was beating down on us, and the cool water of the lake beckoned. I could feel the sweat on my back and could tell B was feeling the same. I said something about wishing we could go for a swim but not packing suits. I still remember the way she smirked and said, "So what?" Without saying anything else she stood up, took a couple steps forward, and started undressing. I stood petrified. I was about to see the crush of my life naked. I had seen bits of casual nudity spying on cousins and other family exposures growing up and had seen some fuck mags at school that friends had swiped (this was before the days of the internet being prevalent) but that was different. I can close my eyes and replay every detail of the next probably five seconds that unrolled in slow motion to me. She kicked her boots off, then turned around and started to peel her Wranglers off looking back over her shoulder at me with a playful grin. Fuck, those wranglers...yoga pants have nothing on a hot girl in good fitting wranglers or even levies but that is a tangent for another time. She slid them off and was wearing lavender boy short type panties. She turned to face me. I was still frozen in place just staring. I could not believe this was happening so casually. She laughed and said something about how I needed to hurry up, get my shit off, and get in the cold water before I made a mess in my pants. She unsnapped her shirt revealing a plain sports bra underneath. That quickly came off and I saw those 32B gravity defying 20 year old tits in all their glory for the first time. She then dropped her panties and she was smooth except for a neatly trimmed patch just above her slit. I was feeling super self conscious as I had never been naked with a girl before much less with a raging hard on. I quickly stripped off with my back to her trying to hide my package, dove in and swam a few strokes before coming up for air. B followed, and soon we were both splashing around like kids. The water was refreshing and invigorating. I was still mesmerized by her perfect body but the setting was so casual I got comfortable with the situation pretty quickly. Maybe it was the cold water or maybe it was just being relaxed but my dick softened up pretty quickly. We swam out to the middle of the lake, and I floated on my back, gazing up at the cloudless sky.

After a while, we swam back to the shore and climbed onto a flat rock to sun ourselves/dry. We lay there, side by side, without speaking for a few moments. As we laid there, I couldn't help but notice how stunning she looked in the sunlight. Her hair was damp from the water and her skin was glowing. She had goose bumps on her boobs (more than that but I was fixated on the boobs) and her nipples were rock hard. I couldn't resist the urge to lean in and kiss her she kissed me back passionately. We continued to kiss as we held each other tightly, and I felt as though I was on top of the world. In that moment, nothing else mattered. In seconds I was hard again. I nervously let my hands explore her body. I wanted badly to feel those magnificent boobs but was not sure if I could get away with it (I was so naïve). I tried to make it seem like an accident and quickly brushed her right tit. I did not fool her for a second because she took my hand and cupped it over her right boob. I just let it sit there for a second savoring the moment before squeezing gently. Fuck yeah… I had finally made it to second base. We continued to kiss while I felt her up. Eventually, we pulled away from each other, panting and smiling. She later told me she was waiting for me to stick it in right there but I once again was chicken/ inexperienced/ taking cues from her (at least the ones I picked up on). I will save you the boring details of the rest of the day where we ate, talked, and kissed a little.

Eventually, we crawled into the tent to settle down for the night, cuddled up next to each other kissing and embracing. I did not yet know, my life was about to change forever. I was about to make it to home base. We had zipped our sleeping bags together. We were both wearing flannel PJ’s (which we changed into in front of each other). As our kissing intensified, I felt her reach into my pants and grab my dick which was already hard. I had never been touched like that before. The feeling was like nothing I knew. She started sliding her grip up and down. I am embarrassed to say, I think I only lasted about 20 seconds before shooting my load. B started laughing and said, “Now look, you made a fucking mess. Now I am going to have to get you out of those things.” The next couple minutes were a blur. The next thing I knew, we were both naked in the combined sleeping bag. We were making out passionately and I was starting to get hard again. I was feeling her up and getting bolder. My hands groped her firm ass and eventually found their way to her amazing pussy I would come to love. I remember being surprised at the dampness. I remember my first thought wondering if the dampness was from piss. I knew so little about the female anatomy at the time. I pushed the thought out of my head and kept doing what felt natural. For that moment, time stood still. It is still a bit of a blur. The next thing I knew, she laying on me kissing and straddling me. She was quite a bit shorter than I am and I vaguely remember her pussy being above my abdomen and my dick touching her legs. I remember the feeling of my dick against her legs because it felt amazing but nothing like what was to come. She reached down and took hold of my dick and started to slide down never breaking our kiss. She positioned me right and slowly slid down onto my shaft. Slowly. Tenderly. She then worked up and down on me. The feeling was out of this world. I remember feeling the warmth, softness, slipperiness, and the gentle pressure. Having climaxed about 20 minutes earlier, I lasted a bit longer this time but not that long. It was probably only five to ten minutes before I erupted deep in her. She continued to grind on my softening dick until I was completely done. I started to say something (I really can't remember what I was going to say) but she put a finger on my lips and shushed me. She rolled off me and we cuddled in silence. To this date, it was a top five or maybe 10 most amazing days of my life.

Now the really sexy part is over but I will share the rest of the night. We eventually fell asleep but were suddenly awoken by the sound of the cattle being spooked. The sound was loud and chaotic, and it jolted us both out of our sleep. Without a second thought, I quickly jumped out of my sleeping bag and reached for my Winchester. The cold air hit me like a wall, and I realized that I was still naked. B laughed as I ran out into the open, naked and charged across the meadow wearing only boots carrying a rifle. I made my way towards the noise and saw the bear in the moonlight . The beast was massive for a black bear and it was trying to attack the cattle that were getting agitated with fear. I took aim and fired a shot, which hit the bear square in the chest. The bear roared and came running towards me. I fired another shot, which hit the bear in the head through its open mouth and brought it down instantly. It was over in a matter of seconds, and the cattle calmed down soon after. We had a good laugh about my running out there naked

When the sun came up I skinned the bear to make a bearskin rug. I rolled up the bearskin. He was old so the meat was not worth saving. As I said earlier, that skin is now a rug in my den and I never told my wife the full story about that night. That was an amazing summer. We fucked every chance we got for the rest of the summer and off and on for the next couple years. We were in drastically different places in life. I really never asked her what she saw in me. I think she was horny and it was scratching an itch. I think she also enjoyed the effect she had on me/control. My friend found out about it later towards the end of the summer when he healed up enough to start working with us some. We fought. I won but felt bad. Eventually he was okish with it and he never told his mom.

[rudolfm]

Wonderful story Chuck.