All right, this is actually a true story. It’s one that’s been imprinted into my minds sexual history gallery because when it happened, it was completely unexpected. (first post – a little long)
I was 18 on a family vacation to a summer cabin on the West Coast. My family was meeting our closest friends, including my best friend and my sister’s best friend at the time. This family’s name is the Henderson’s and they were also bringing along the Henderson’s father’s brother (around 35) his fiancé (early 30’s) and the fiancé’s younger sister (around 30) who had a son who was around 7 at the time. So as it goes it was my family in one cabin, the Henderson’s in another, and the Uncle and his fiancé and her sister’s in another.
My parent’s are liberal people, and having just graduated high school, my best friend and myself were considered adults throughout the trip. The older adult’s on this trip loved to party, and wine and beer flowed from the porches to the beach all throughout the early afternoons and into the nights of perfect weather. My best friend and I had access to beer and wine whenever we wanted, and often spent the evenings after the large group dinners lugging hidden beers in our pockets down to the beach. We met a bunch of other young vacationers our age and partied on the beach early into the morning’s aiming to meet girls at the various fires that littered the coastal beach.
I had known the Henderson’s uncle and his fiancé for a while as I grew up so close to the nephew. I had never met the fiancé’s sister or her son, and as this is whom the story is about I should probably describe her. Her name was Elena and like her older sister, she was an extremely beautiful woman of Ukrainian descent. She had dark tanned skin and really thick brown bushy hair that she kept up in a ponytail. She was around 5’5, with large breasts and an hourglass figure that had only been accentuated from childbirth. She had these big blue eyes, and round cheeks, that were kind and red and extremely feminine. She was the definition of a MILF, and one that when I first met couldn’t believe that she was a newly single divorcee.
Now being my best friends sort of auntie put Elena (and being only 18) in my mind completely off limits. I remember her giving me a hug after my friend introduced us, and saying that she had heard so much about my family and me from her sister. They had arrived at the cabins before us, and she was wearing a sarong and a bikini top, and had a glass of white wine in her hand. When she bent over and hugged me in front of my parent’s and I had to awkwardly adjust myself afterwards because of her attractiveness.
Throughout the week my parent’s, the Henderson’s, and the crazy “Ukrainian girl’s” would gin and tonics every cocktail hour, take turn’s making dinners, and generally just have a good time between the cabin and the beach every day. During the beach day’s, we would all be lying together in a group and Elena’s young son was constantly after me and my best friend to play soccer with him. Elena, in her sexy mom bikini, would often join in playing along with my friend’s uncle, and enjoy chasing her son around while her breasts bounced in the sun.
After playing, we would all go for swim’s in the ocean together to cool down, and being the 18 year old I was, I couldn’t keep my eyes off of Elena, despite the family surroundings. I mean she was beautiful, and in a bikini basically the whole time, transitioning between being the cool ‘older auntie to my friends and their friends’, to being a mother to her son the next minute.
Elena really took a liking to her sort of nephew and me and was always asking us about what we did when we took our beers down to the fires in the evening. We were the next ‘youngest’ people at the cabins and I could tell she was enjoying herself, but a little bummed out that she was essentially the 7th wheel of the adult couples.
As the week went on I could tell more and more that Elena liked me looking at her, especially when she had something to drink. She was never flirty with my friend for obvious reasons, but whenever I was alone with her I could tell she enjoyed my company and conversation. She would always get me to help her with things, be that bringing chairs to the beach or helping her open a bottle of wine. She probably caught me a dozen or so times checking her out in her bikini. I also noticed her watching me walk out of the ocean a few times, and as the week went on, I tried more and more to hide the glances I was giving her because or our surrounding company.
At the time, I was about 6’2 and 170 pounds at the time and quite fit from playing soccer on my high school team. Despite being deemed attractive by all of the high school metrics, I had only been with one girl, who was my high school sweet heart until the Christmas of senior year. I was always sort of nervous around girls, and having heavy academic and athletics schedule, I was never really into the party scene.
The first time I realized Elena may be enjoying my company on more than just an older friend level was one afternoon when coming back from the beach. Our cabins were a short walk up the hill, and before walking up, many people showered in these cabanas you had to put a quarter in to use.
So on the 5th or so day I went to open the door to the first cabana and when I did I found Elena helping her son change into his shorts. Elena was only in a towel, and her son had just put on his underwear. I apologized and quickly went to shut the door when she said that I should just come in and wait for the shower. When she got her sons top on, she sent him outside to her sister who had just finished showering and was waiting for Elena. I stood there awkwardly as Elena put her shorts on with her towel around her making small talk to me. She could tell I was ogling her and she sort of smiled at me while she questioned how my day was.
Then, in an instant, she dropped her towel off of her and was standing there topless looking right at me before she quickly put a tank top on. In that instant, I saw a pair of the most beautifully shaped, round and voluptuous breasts I had ever seen. They were a real woman’s breasts, weathered and beautiful. She did this like it was no big deal, but could totally tell that I was stunned by it. She turned to grab her stuff, told me to have a nice shower and then winked at me before she left.
So there I was, rock hard in the cabana shower having just seen Elena topless. I was asking myself what the hell just happened, and decided to chalk it up to a European thing and just go with it. Elena probably didn’t care if I saw her tits, but the way she did it, and the fact that my she was like my friends aunt made things seem like they had crossed the line, but that it was a good thing they had.
Later that night, Elena and her sister were making dinner for everyone and the whole time I couldn’t keep the image of her breasts out of my mind. At the dinner table I constantly caught Elena looking at me, while everyone was starting to get drunk a lot quicker than normal. The out of nowhere Elena asked if she could accompany me and my friend down to the beach, or if that was off limits because we were meeting girls that night. We obviously had no objections to it, and then my friend’s uncle and his fiancé said they wanted to come party on the beach as well. The alcohol flowed and my friend’s uncle put on some music on the main cabin’s deck and we all had a mini dance party, parents included, while drinking gin.
We were about to leave, when Elena noticed us going and decided to put on a hoodie and join us. My friend’s uncle and fiancé said they would come later, so it was only me and Elena and my friend walking down to the numerous fires that scattered along the beach bluffs. On the walk down, Elena grabbed my friend and my arms and walked between us. She sort of rested her head on my shoulder and I could feel her warmth against me each time she grabbed my arm tightly. We each had beers in our pockets and began drinking them while she questioned us on who were the cutest girls and if any of us had gotten any action at the beach.
We arrived at a fire that was packed full of some college aged people, who happened to have a keg. Elena, being the oldest one of us there, politely declined doing a keg stand when some of the older guys had begun to notice and hit on her. She was enjoying herself, and every so often I could see her blue eyes look for me in the crowd when she was talking to someone else. She would look at me and smile.
We began sitting on a log together by a fire and Elena began trying to scope out girls for us to hit on like she was someone our age, having fun at a party. Then the uncle and his fiancé arrived and everyone kept drinking and socializing. My friend had followed a girl to another fire just down the beach, and Elena wanted myself and her to go and join him.
We left to stumble on the beach to the next fire in complete darkness, only the stars over our head, and Elena grabbed my arm and wrapped herself around it. We were both drunk and she was starting to become more flirtatious. Half way between the fires, engulfed in the darkness, Elena stopped and said that she had to pee. She grabbed my hand and scrambled up one of the beach bluffs to the top of it, pulling me along with her. My heart began pounding and I could feel myself sweat as we reached a suitable destination away from the beach. Elena true to form stopped, pulled up her dress and down her panties and peed behind a bush. I stood there in silence as she giggled and told me not to be ashamed of watching her while she peed. I couldn’t see anything and I was only escorting her. My brain began to calm itself. Nothing was going to happen.
Elena finished and we walked along the bluff for a bit. She began holding my arm and I could feel her pace slow. She didn’t actually want me, did she? Then, out of nowhere she asked me if I liked what I saw earlier in the cabana. I was sort of stunned and mumbled that I did. Then she stopped me, and turned to stand in front of me. She unzipped her hoodie slowly while looking up at me. I was drunk, but I saw the look in her eyes that were focused on me. They were full of a lusting desire I hadn’t seen from her.
She asked me quietly and with a smile if I wanted to see them again. I didn’t know what to say, so I just sort of nodded in shock. Then she opened up her hoodie and slowly pulled down her dress so that both of large breasts busted out of the top of it. She looked at me for a moment, then took my hands and put them on them. She looked at me and said “they are wonderful breasts, aren’t they.” I stood there for maybe a minute with her eyes fixed on me, hands on her breasts, and completely breathless. She then pulled me close to her and we began kissing softly.
I was in complete shock. This was my friend’s sort of auntie. She was 30 years old, she had a kid, and she was staying with us. After a total what the fuck moment, I began to realize I was rock hard in my board shorts. She stopped kissing me and asked me if everything was okay. All I remember is I pulled myself back to her breasts like a child and began sucking on her nipples as quickly as I could, and I let my hand reach between her legs and began petting her pussy over the top of her panties. In a minute, she was moaning, and softly kissing my ear as I kept on sucking on her wonderfully shaped breasts. Then she grabbed my hand under her dress and stuck my fingers past her panties and I got to feel how wet she was. My fingers were sliding slowly in and out of her lips that I had yet to see, but that were so wet that my fingers were drenched in her juices.
She began fondling my cock over my shorts and feeling it, gripping it in her hands as I continued to touch her breasts. I was surprised that despite how forward she was with me, everything about her was gentle. Nothing was forced. She was sensual.
She pulled my head up to her and began kissing me again, and she slowly undid my shorts and pulled cock out of them. She stroked it slowly while we kissed and then she pulled away from me for a second and surveyed the bluff. I nervously began to pull my shorts up when she turned to me and said that she just wanted to make sure no one was near us.
Then she looked up at me and said “I’d really love to fuck you right now, but were not doing it in the sand.” She then reached her hands back down my pants and pulled my cock out, bent over and put it in her mouth. She then lowered herself to her knees and began stroking me while surveying the bluff again.
She looked up into my eyes and whispered that “she didn’t remember her boyfriend at 18 having a cock the size of mine.” She then began to slowly suck on it, going deeper and deeper with each motion of her head. I was rock hard, despite being drunk and within 30 seconds I felt like I could cum into her soft cheeks. She stopped again and looked up to me and whispered, ‘Jesus, you have a nice cock’ then began to lick the shaft of it before swirling her head around the nob of it. These movements, and her stroking could have only been going on for maybe a minute and a half. I think she could feel how tense I was, and she began to pick up her pace, and removed her hands from my cock and put them on my bare legs as she bobbed her head back and forth on it. After 30 seconds of that motion I couldn’t hold it any longer, I grunted and tried to warn her, but she just kept going and going, sliding my cock in through her thick gorgeous lips. I began to come, and she was ready for it because her motions and the power of her mouth only became stronger. I came and I came and she hadn’t let the nob of my tip go past her lips. Her fingernails began to drive into my legs scratching me, as I filled her mouth and she just kept taking my cum in her swallowing it and sucking. I was finished, and she slowly released my cock from her mouth and swallowed again before wiping her face with the arm of her hoodie.
She stood up and looked at me. I was completely dazed. She looked around again and slowly pulled my shorts up over my cock. She put her breasts back into her dress and zipped up her hoodie. She turned and walked to the fire down the bluff like nothing had happened and I followed, still in complete ecstasy from what had just occurred.
The trip went on for two more days after that, and as this is already long enough, I won’t continue with that story now. Needless to say the reality of what occurred is still with me today. Elena still is a beautiful woman, having re-married now and I am a still close friend with the Henderson’s. When I am home, I still occasionally run into Elena at their house, but it’s been a decade since this first secret encounter happened.
Source: reddit.com/r/gonewildstories/comments/407rrx/how_a_vacation_with_family_friends_turned_into_me
Bravo. That was perfection mate. And one hell of an 18 year old’s wet dream!
Wowza…that’s one awesome tale! It sounds like there may be more to this…if so, I can only hope you’ll be willing to share it. :)
I do hope you write another story to detail the rest of that trip!
Wow
Great story but holy hell, research plural vs possessive.
>I decided to chalk it up to a European thing and just go with it. You are kind of right in fact, I am from Russia, and I don’t know about the rest of the world, but here most Ukranian women have reputation of being easier, sometimes much easier than any other women. And they do dress more revealing and wear excessive makeup, yes, even more than Russians. So it gave me a slight hehe feeling when I’ve read she’s Ukranian, like, oh, I see, everyhting adds up.
yo. where are you from? where is this taking place. Curious minds want to know
Agreed, this is annoying the hell out of me.
ya. I understand why the reddit world gave you a minus upvote for your bigoted opinions about Ukrainians. Although I live in Bali with a lot of Russians and Ukrainians so I have heard these feelings from Rusky’s and it always cracks me up. But seriously could OP let us know where this is taking place. I though in the states at first until he said board shorts which I really don’t hear too much of in Murica.
So did a second "encounter" happen? Will be looking forward to another story!
I wouldn’t say it if my experience didn’t prove it;)
spoken like a true bigot. hahah
Began, began, began! So much beginning in this story, it was difficult to focus on the events when you’re getting tangled up in the repetitive writing style. The comfort in this is that unpolished writing gives an authentic feel sometimes, as the better written stories sometimes play out too much like erotic fiction.
Well, no one ever gave me counterarguments. And there is hardly any evidence against it, so one’s own experience and word of mouth is all you can basically rely on.