A Family Affair

After a few serious posts, I thought I would give you guys something a little more juicy. I don’t want to give away the story in the title so please, read on!

I have been involved in the swinger/lifestyle scene for many years, starting in Chicago and then around the world in the various places I have lived. Whenever I move I always look for the scene but sometimes the scene comes to me. I meet people randomly who are involved in a more sex positive lifestyle. Like attracts like. But that is not what this story is about.

A few years ago I was walking on the promenade in my city headed to meet my partner for a date when I saw some scene friends I had known for a few years (Jake and Kelsie). They are a great couple. Super fun, sexy, and would recommend other people for the parties my partner and I host. I always counted on them to bring a lot of life to the parties with good conversation (and a lot of play). Sadly Jake and Kelsie moved away. They started a family and are likely living a more family oriented lifestyle. I am quite happy for them!

As Jake waved me over to say hello, I noticed something strange. Kelsie looked really different. I knew they were looking to have a baby, and it had been a few months since I had seen them but something was off.

As I got closer I realized it wasn’t Kelsie at all! Jake was sitting with Kelsie’s sister. The resemblance was striking. I didn’t even know Kelsie had a sister – we don’t talk a lot about our families when we are busy with other activities.

Jake introduced me to Carmen (these names are all fake) and we had a quick friendly conversation before I continued down the promenade to meet my partner. “Nice to meet you” and “lovely to meet you, but I must be going now.”

A few hours later Jake sent me a message. “Hey man, what did you think of Carmen?” I said she seemed quite sweet and cute, was nice to meet her and get to know them even more. Jake responded, “Cool man. Kelsie and I were talking and we we’d like you to fuck her.”

At this point I was understandably shocked! From our quick conversation I could tell Carmen knew absolutely nothing about Jake and Kelsie’s extracurricular activities. So why was he asking me to play with her? Did he tell her about the parties and lifestyle? Also, I had played with Kelsie many times. Wouldn’t it be weird for me to also play with her sister??? These are all questions I asked Jake.

He responded that Carmen was currently in an unhappy marriage and could really use some fun. It had been a while since she was intimate with her husband, and they were headed for divorce. Both Jake and Kelsie thought it would be a nice thing for me to help Carmen take her mind off her troubles and let loose a bit.

I thought about it (not too long) and agreed. I’d love to “help out.” Carmen was quite attractive so it was not like I was doing anyone a favor. I actually couldn’t believe one of my fantasies that I never thought possible was actually going to come true – having sex with sisters (not at the same time – that would have been a bit weird for everyone).

Jake told Carmen I was a good dude whom he trusted. And that he and Kelsie thought I would be the perfect person for her to have some fun with. I was honored to be thought of this way. I really appreciate having friends that would trust me with someone close to them in a most intimate way. I even told my partner and she was pretty shocked as well. This isn’t a normal “can you do me a favor” type of ask from friends.

I got Carmen’s contact and sent her a message. We chatted a bit and set a date. I met her at a local bar near my place, chatted more face to face. I asked about her experience, what she wanted out of the experience, and if she also thought it was a strange way to “meet” someone. She agreed.

We laughed a lot and had a good time. Carmen had actually not been with many people other than her husband; and she’d been married for a long time. She talked about the marriage, that is was pretty rocky, and how she did not think it was going to last much longer (they got divorced within 6 months).

Carmen and I headed back to my place shortly thereafter. I was not expecting much as she mentioned she had limited experience. I thought I would be leading the entire way and she would be very shy. Boy, was I wrong!

Carmen was a ball of energy, a sexpot! I could tell she really loved sex in every aspect. For a gal with not much experience she knew how to handle me! I’ll refrain from getting into the specifics (I think it is quite crass), but from the foreplay to the sex and orgasms – the whole experience was amazing. It felt like Carmen had been having sex for years, trying out many of the non-vanilla aspects of play, honing her craft along the way. She truly enjoyed herself and her body. And that turns me on more than anything. A confident woman who enjoys herself and is not afraid to ask for what she wants.

Jake called me up a few days later asking how everything went. I told him how much fun I had and that my expectations were blown away. He said Carmen also reported she had a very nice time – always good to get positive feedback! And that was pretty much it. Both he and Kelsie were happy to hear all had gone well. (FYI – Jake had also told me not to let Carmen know about their lifestyle or that I had been with Kelsie).

I saw Carmen a few more times throughout the next year until she met a new guy and fell in love again. I was happy for her. She had gone through a lot, and to hear she was now getting what she was missing from her marriage was really nice to hear.

Reflecting as I write about this now, I’m reminded of the unexpected and sometimes unconventional ways life brings people together. Carmen’s story is a testament to finding joy and liberation even in challenging times. It’s been rewarding to be part of her journey.

Have you had any experiences like this? Would love to hear the most unconventional sexy story you are brave enough to share!