It’s hard to believe that it wasn’t until my mid-30’s when I hooked up with a woman that I had just met that same night. I have had plenty of fun encounters but they were always with someone that I had gotten to know beforehand. This story happened just over a year ago. There is no cheating element in this story, and I did not write extensively about the actual fucking we engaged in. However, when you get to that part, feel free to indulge in your devious imaginations….
A former coworker of mine was getting married and I flew into his city on a Friday for the Saturday wedding. Having never been there before, I selected a Monday return flight so I could explore the area a little bit more on Sunday after the wedding. Upon checking in at the hotel, I met some older couples (probably 60+ years old) who were all related, and also going to the wedding. We chatted and with me being solo at this wedding and not knowing many people other than my friend, it was great talking to them.
Fast forward to the Saturday wedding – it was a beautiful ceremony and there were 12 bridesmaids and 12 groomsmen. I chatted politely with other people at the wedding and then also at the reception. I ended up in a great sports-related convo with another guy at the wedding and I was planning on a very early night for me. There was a hot 47-ish woman dancing near me who kept eye-fucking me as she ground on her dance partner. Flattering? Yes. I liked the glint in her eyes. But I passed, perhaps out of habit. I went to get another drink, and ran into one of the older couples that I had originally met the day before at the hotel. Then another, middle-aged couple came up and started talking to them. They introduced me to them and I had quite the convo with the guy. We talked a lot of sports and had quite a few things in common. Again, I enjoyed just talking to people. After 10 minutes of conversing, him and his wife took their leave and I went back to the dance area.
I took some pics with the groom and he told me to go to a balcony where people were smoking cigars. I never made it to the balcony because I ran into that guy I had just been talking to. Again, we spoke again, at length. Turns out the bride was his niece, and that he has a son and daughter of his own. I didn’t think anything of it. Eventually, I went back to the dance floor.
I love dancing so I made my way into the dance floor. There had been a cute blonde that I had seen earlier, and there she was on the dance floor. I made my way near her and started chatting her up as we moved to the beat. Almost as soon as we were talking, a woman’s hand reached out over her and pulled me towards her – it was yet another cute blonde, but one I had not seen yet, and she was wearing a bridesmaid dress. She was around 5’5″, 140, long blonde hair, blue eyes, and as I would find out later, has incredible breasts (think: bigger than you thought). Like I mentioned, I love dancing, and pretty soon we had a fun innocent-wish dancing group going. The blonde bridesmaid was definitely into me and invited me to the after-party that the wedding group was going to – I didn’t even know about an afterparty, so of course I accepted. During one of the songs, a middle-aged woman came and started dancing with us and I recognized her – she was the wife of the guy I had been talking to earlier in the evening. She left after a couple songs, and my new bridesmaid friend told me that was her mom. It was then I made the connection about who this girl was (unbeknownst to me, her parents and friends had been telling her to meet me throughout that night, talking me up, essentially being wing-people for me).
The reception finished and we all went to a nearby hotel lounge. It became clear that everyone was wrapping up their night, and it was only around 11pm. My new bridesmaid friend and I kept talking – she was so interesting and we had such a wide-ranging conversation about many topics. It was very refreshing. I found out she was about 11 years younger than me, which I thought was hot. For most of my life, I’ve mostly engaged with women 10-20 years older than me. She and I then went outside for a walk, where we continued to talk. I told her about my kids (and that I don’t want anymore), we talked about the last time we fucked (it had been a few months for both of us), and we laughed how I had met her entire family that night. We arrived back to the hotel and she hesitated. You know that “I don’t want to uber home and I’m going to stare in your eyes saying nothing” look? That was it. I asked if she’d like to come up to my room, and she said, “Yes, I would.” So up we went. Having never hooked up like this before, I was thinking thoughts like – “I can’t believe I asked her this, this feels really natural with her, we’ll probably just make out and fall asleep together, it’s hot she’s 25, etc….”
We get to my room, put down our half-full drinks, and our eyes connected. I moved in closer to her and kissed her gently. She responded in kind. I consumed her lips a bit more, and she responded to me. We passionately made out for at least 10 minutes just standing there. She was a very good kisser and I liked how she smelled – those are two big things for me. My hands started to roam all over her body, and she could feel how hard I was. I moved her to a wall and pressed my body into hers, my hard cock on her thigh, pulsing and throbbing. I pulled up her dress on one side and ran my hands up her bare leg. Goosebumps appeared on her skin and I didn’t stop until I got to her ass. She was wearing a thong (yet another green light for me) and I began to massage her ass while our mouths became hungrier and hungrier. I started to kiss her jawline, neck, and ears, and she lustfully moaned, “you’re making it really difficult to behave myself”, to which I replied, “what if I don’t want you to behave yourself?”
Eventually we moved to the bed. We stripped each other and I started to slowly enter her tight, soaking wet cunt, pressing her back into the bed. She groaned at my size, her eyes open wide, mouth open, her breathing ragged, crying out my name, clawing at my body. Our eyes were locked the entire time. Once I was all the way in her, I held her there as she adjusted to me and we kissed passionately. Then I slowly started to move my hips in and out, a little bit at a time. After a few minutes, my cock was covered in her cum, she was screaming my name and calling me “babe”, and her body was seizing up as her first orgasm ripped through her. I stayed in her as she recovered and then I slowly began again, building up more and more speed.
We did several more positions throughout the night and fucked the rest of the night (around 5 hours), literally until the gray of dawn started to appear. I lost track of her orgasms and I had a few of my own. There were more than a few moments where she needed me to go slowly. I thought that maybe she just liked gentle sex but that wasn’t the case – she told me that she had never, ever fucked like this before and all of these sensations were new. This girl definitely was not a virgin, either. We eventually fell asleep for a few hours, and woke up and fucked again. Then we showered together and made plans to go on a date later that afternoon at a local museum. The date was great, dinner was excellent, and then we went back to her home and fucked all night again. The next morning, we ubered to her work, kissed, and then I went back to my hotel to get ready for my flight back home.
We ended up spending a weekend together a few weeks later, and it was much of the same. ;) But with her eventually wanting to have kids and a family, and me already being beyond that stage, we ended up going our separate ways very peacefully and made some amazing memories for the both of us. And now my eyes have been opened to younger women, as well, thanks to her.
Source: reddit.com/r/gonewildstories/comments/z0b2zw/i_m_fucked_a_bridesmaid_f_who_was_also_the_brides