How a vacation with fa[m]ily [f]riend's turned into me hooking up with a 30 year old mother as and 18 year old. (Part 2) | 2016

The link below is to the first story.

https://www.reddit.com/r/gonewildstories/comments/407rrx/how_a_vacation_with_family_friends_turned_into_me/ That night, after Elena and I descended down the bluff and made it to the fire, we met the others. I remember being in sort of a dazed state, and I decided to separate myself from her and the group consciously. At one point, I caught her eyes across the fire, but she turned away from me quickly and I later saw her leave back up to the cabins with the Uncle and her Sister.

That night my friend and I also got very drunk. There was a good vibe, and my friend was having some success with an older girl he had met earlier in the week. When I woke up the next morning, it took me a moment to remember that what happened between Elena and I actually did happen. I went down to breakfast and I suddenly had this weird paranoid thought that everyone knew what had occurred, which was impossible, but still an awkward state to be in considering my mother was probably serving me and my little sister pancakes that morning.

When I got to the beach that day, Elena and everyone else was already there. I could tell most of the group was quite hung-over and the general mood was laziness. Elena had positioned herself on the far end of the group with her son, which was odd because she was usually sat right in the middle with the younger people, and she was wearing these large black sunglasses, which hid a lot of her face and her eyes that were usually so animated when she spoke.

I remember lying on the beach most of the morning reading, avoiding the world around me and trying to figure out if anyone except Elena knew about what happened between us. Or if she, for some reason, was angry with me.

Almost everyone went back up to the cabins at different points for lunch, and my friend and myself stayed to watch over the beach stuff. I decided to take a swim on my own to try and shake off the hangover. I spent a few minutes in the ocean wading around looking out to the horizon contemplating my life, when I turned around and saw Elena slowly wading through the surf in her bikini. She was completely alone and, but most of the family had returned to the beach. My heart began pounding as I debated how to deal with the situation, or if I should say anything at all.

When she was finally within earshot of me she said ‘hey’ and swam up beside me. She was still wearing the black sunglasses and I couldn’t gauge her voice or mood. We sort of waded in silence for a few moments before she broke it by saying that she was very hung-over. I sort of laughed and replied that I also was. She then looked at me and asked if I had mentioned anything to my friend about what had happened between us. I replied that I hadn’t, and would not say anything to him or anyone else about it.

Then she asked me to hold on to her sunglasses while she dunked her head under. When she took them off I saw her eyes for the first time and they smiled at me. She plunged down into the ocean for a few moments and when she bobbed back on a near sand bar, she ran her hands through her thick dark hair to remove it from her face, then facing me - and out into the ocean - adjusted her bikini which was just above the water surface, letting me briefly see her large, tan-lined, white, round breasts and perky cold nipples.

She waded back over to me slowly and we talked casually about the night avoiding the subject of what had happened between us. Then she as she waded closer to me, I felt her foot brush up against me in the water. She had stretched herself out, so that her head was the furthest point away from me, and smiled and looked toward the shore. I let her foot meet my crotch in the water, and she stared at me. I became hard instantaneously.

She then said that the dynamics of the weekend made it impossible for anything to happen between us. I completely understood, but her foot hadn’t left my crotch area. I then asked her if there were a chance of us being alone in the next few days, would she take it. She never really responded – but she playfully took her sunglasses back from me and swam back into shore. I watched her adjust her beautiful Ukrainian bum in her bikini a few times as she exited the long, shallow water and ascended up to the beach. At that point, every man on the beach was probably watching her walk through the sand.

The next few days passed in a haze of looks and lust from my point of view. I remember taking a few ‘long showers’ to try and control my thoughts about Elena. It was virtually impossible for us to find time together, as the adults partying at night slowed, and her son had developed some sort sickness. Every night I went to the beach and hoped that she would somehow turn up alone, but I knew that hoping for it was irrational - and I began chasing the girls my own age again. Elena was 30, a mother of a young son, my best friends sort-of-auntie’s sister, and was currently part of a vacation party that included my parents and little sister. My horny, 18 year-old wisdom, tried to push these thoughts of practicality into my mind every time I saw her, and I began trying to avoid her gaze, even when it was directed at me.

Elena had also cooled down on the flirting with me in public. I was starting to get signs that maybe it was best that nothing else happened, as her son was sick, and the drinking at night had died off.

The final night of trip was my father’s birthday, and the whole group was going to the areas best restaurant for seafood. Everyone got dressed into less casual beachwear and loaded up into the two of the three vehicles to head out for the meal. During the dinner I sat at the opposite end of the table from Elena, and neither of us could see each other. My parents, the Henderson’s and the Uncle and Auntie were all enjoying the wine that flowed throughout the dinner and towards the later part of the evening, my friend was after me to leave to go to the beach for the final night of our vacation.

We decided that I would drive the younger people back in one of the vehicles, and as we were about to leave, Elena popped her head up and asked if there was room for her and her son. Her son was still under the weather, and was fading quickly as the night carried on and she was rightly feeling that her duty was to leave the ongoing dinner party, which was promising to pick up as the adults were figuring out a taxi situation home for later. So, Elena and her son piled into the mini van with us, that I drove for ten minutes down the highway back to our cabins.

When we arrived, Elena’s son had fallen to sleep and she asked if anyone would help her carry some things back to her cabin. My friend said that he would bring me take a backpack full of beer down to the beach with our little sisters and that I could come meet him. I quickly offered Elena my services and followed her with her bag to the empty her empty cabin, which she shared with the Uncle and Auntie. When we got inside she took her son to the bedroom and I placed the stuff on the counter. I sort of waited there alone, tensely for a moment, hoping she was going to pop her head out of the room at any moment and look at me. When she didn’t, I called to her that I was going and she faintly replied from the bedroom that everything was okay.

As I walked down to the beach I sort of figured that my moment had passed and that what happened between Elena and I, was something that wouldn’t happen again. The dynamics of it were rightfully impossible and the fact that something had happened was already implausible and had given me feelings of unease.

When I arrived at the closest beach fire, I couldn’t find my friend and I was thirsty for a beer, so I decided to turn around and run quickly back up to our cabin which had a cooler full of beer on the deck of it. I was intending to get drunk that night and hoping to meet another girl my age – maybe someone to get a kiss from and to take my mind off Elena.

When I got to the deck, I looked over at the cabin Elena was staying at and saw her reading a magazine a drinking wine in the living room. She had this light summer dress on, which wrapped around her breasts and revealed her shoulders and chest completely. I stared at her on the porch, before turning and taking a beer from the cooler. When I turned around, I saw that Elena was quickly walking on to her deck.

When she got outside she looked at me and said in honesty that she thought I was someone stealing beer from our deck. I said I was just back grabbing a few beers and that I was going back to the beach. She sort of looked at me for a moment, and her body language shifted. I don’t know what happened in that moment, but it just clicked that I was supposed to be there and I was supposed to go to her.

I bravely asked if I should come over, and I could sense her hesitation. The adults were probably going to be home sometime within the hour and her son was sleeping inside. She sort of nodded and walked back inside, leaving me to walk around the deck and up to her place alone.

When I got inside the cabin my heart was pounding. I hadn’t had anything to drink at dinner and my nerves were starting to get the best of me. Elena stood inside the living room and watched me. I could feel her eyes on me and could tell that she was thinking. We both stared at each other, wondering what to do. We both sort of looked at the clock then suddenly Elena turned and walked up to the steps of the loft above the living room. At the foot of the steps, she motioned for me to follow her and watched her slowly climb them in front of me, out of sight of anyone below.

The loft had a pull out sofa at the back of it and a small bathroom off the side of the staircase and most of it was occupied with Elena and her sister yoga mats.

We stood up there for a moment in silence. I really couldn’t believe what was about to happen, or where I was and both of knew we shouldn’t have been there.

Elena looked gorgeous in the dress she was wearing. She had her hair pulled back into a bun revealing her beautiful neck and perfectly round sun tanned face. Her breasts were basically busting out of it and I could feel her soft warmth as she approached me. At this point I could barely breath out of anxiety and nerves.

Then – in an instant - she approached me, looked up at me, and pulled herself towards me. They were so soft and round, and her tongue was strong and womanly. We kissed in silence for a few moments. She slowly pressed her body against mine and I remember grabbing her bum and running my hands along the soft of her back.

She parted from me for a moment and sort of looked up at me. She whispered that we had to be quiet and that we didn’t have much time. She led me over to sit on the sofa bed against the back wall of the loft.

Elena climbed on top of me and when she did, I pulled down her dress to reveal her large, round, mother breasts to the height of my face. I began to kiss them again, putting each nipple in my mouth as Elena ran her hands through my hair. She began riding her dress up her legs, until only our waists were separated by her underwear and my shorts, and my hands made there way to her parted lips beneath her underwear. Next thing I know, she had undone my shorts and pulled them down enough so that she could stroke my cock while she kissed me.

Then suddenly, she paused and stood up. We both went silence as we listened for signs of someone below. I literally looked at the pitch of the roof out the window incase I had jump out of it.

We stood there in silence as the noise passed. I could tell that she knew we should stop, but something about her eyes made me realize she wasn’t going to.

As she stood there, she broke the silence by lifting up the front of her dress and then removing her underwear. She let her dress fall down again and she walked over to and positioned her knees on either side of me, letting my cock fall inside her dress.

She then hiked her dress up around her stomach, and keeping her breasts revealed. She lowered herself back down in front of me. Her pussy had a tuff of kept hair grown over it - very feminine and well kept - and womanly. I put my hands up to feel her warmth and soft wetness and she looked at me with a sense of longing.

She could see my hesitation - nervous about the fact I didn’t have protection. She looked at me and assured me that she was on birth control and that she was clean, and that she wouldn’t put me in the position unless I was safe. It was with the almost motherly re-assurance that she calmed me down enough. At this point, how could I have said no to her?

A second later she was lowering her beautiful wide hips and soft pussy lips, onto my cock. Neither of us breathed at first. I think it was out of fear. Then I was suddenly inside of her, and as my fear subsided, her breasts began bobbing up in down in front of my face and I realized I was actually having sex with Elena.

Everything about the motions was slow and yet forceful. I remember how warm she felt to me and how wet my cock felt as she slowly bounced and rubbed herself up and down on my lap, using every inch of me. There was no hesitation or awkwardness. It was just sex on a loft couch in silence.

I watched her face as she closed her eyes and bit her lip, and increased her thrusting on top of me; always conscious of the noise level of the sofa we were on. Elena began to go deeper and deeper, riding and pulsating on me for her own pleasure as much as my own as her dress dropped down over our waists. I tried to kiss her everywhere I could, but she wanted me to focus on her breasts as she wrapped her arms around my neck and rubbed her hands through my hair.

During it I remember being aware of how insane the whole thing was. This beautiful Ukrainian woman was on top of me, and she wasn’t fucking me, but more releasing herself on to me. She maintained me inside of her the whole time, and I began to clench my inner organs, trying with all my might not to cum in her every moment I was inside of her. I held on. I held on to the sound of the sofa bed squeaking and Elena’s faint moans and grasps for breath.

I pulled her closer to me, and I whispered to her that I was going to cum. She looked at me and kissed me. I changed my arms from grabbing her ass to keep it on me, to trying to lift it off of me so I could release myself. I told her again that I was going to cum – and sensing my reluctance to cum inside her – she let me remove myself from her and lifted up her dress, placing my cock between us as she leaned back and I came all over her stomach, her dress, pussy and our entwined legs.

I don’t think I lasted longer than five minutes, but I could sense her looking at me, and when our eyes met her face was flushed red and she was panting. We sat there for a few moments looking at each other until Elena stood up.

She didn’t say anything, but she let me look at her, while keeping the front of her dressed raised, avoiding getting my cum on more. She gave me this sincere look of happiness and then asked if she had been moaning loudly, which I honestly couldn’t remember. I don’t think it was loud, but I remember her breathing and her faces animated looks of pleasure. Cum was dripping down her stomach and her into the light mesh hair of her pussy.

That image of her, dress rolled only around her mid stomach, her large breasts covered in my spit and her stomach, groin and thick thighs full of my cum, the sparse and maintained crotch hair glistening with our juices. That was what a woman looked like after making private love.

After this moment, she walked to the bathroom to clean herself off while I stood up and did my shorts up.

A sense of urgency set in, as we both realized that I had to leave as quickly as possible. She gave me a towel to wipe myself off with, and told me that I should go.

We didn’t kiss, there wasn’t a long a goodbye. I looked at her once more and she smiled, and then I ran down the loft steps and exited onto the balcony.

Here is what is really messed up about this. As I get outside and the rest of the adults had all just arrived on my cabins deck for a drink. They could have easily seen me exit the living room of the cabin from the deck. I knew that none of them had seen me because all of their attention was focused down toward the beach. I slowly slipped down the stairs on the opposite side of the deck and was planning on maneuvering around the front of the house, under our cabins deck and back to the beach. But on the path, just as I l tuned away from the deck - I ran almost square into my friends Uncle.

We stopped and looked at each other, and he gave me this, what the hell type of gesture. I said that I was just grabbing some beer. He actually stopped me and asked me if I wanted to come in for so more. I declined and walked away slowly.

From a bush not far away, I watched him through the bay windows walk into the house - that were essentially the front wall of the cabin - and I saw Elena descend from the loft above. There was something (well to me at least) that was obvious about her body language being off, and it looked like she had just changed or re-arranged herself, not realizing who was actually inside the cabin. I remember watching the Uncle sort of stare at Elena, and then motion to ask if I was just in the cabin. At that point, I just ran to the beach. I didn’t even want to think if he had seen us from that pathway.

I also realized that from the angle I was standing at, which was mostly thick brush, someone could have seen Elena or I standing in the loft naked together.

When I got to the beach to meet my friend, I began drinking quickly. I couldn’t believe what had just happened, and the rush of almost getting caught was making me nervous. I think I told my friend I had eaten some bad fish, which had caused me to sit on the toilet for 20 minutes. He didn’t question me, which is good because the reality of where I had just been sitting was something I didn’t want to discuss.

I found out a few years later that the Uncle and Auntie both knew about what happened between Elena and I. I guess Elena confessed to her sister about the ordeal after a few bottles of wine later that evening. Like I said in the last story, both of them are very cool and open-minded people and at the time I was legal. Neither of them lead on that they knew anything, but I could definitely tell that my friends Auntie looked and me differently and treated me differently after that.

After all, I was 18 and from that point on, I guess I was one of the young adults at the family functions we would attend together with the Henderson in the years to come. Some of which were before the time Elena was remarried.