It had been a LONG time since a first date with someone in the lifestyle. I went back and forth about going on this one; my husband gently encouraged me to “get back out there” while leaving the decision up to me. I decided to bite the bullet and go for it. And I am so glad that I did. A little backstory - he (let’s call him Jake) is polyamorous. He has been with his current partner for almost three years and he has a lot of experience in this lifestyle. Pretty much the opposite of me. He knew I was nervous coming into the date so we met at his place, grabbed a drink and ordered some food. We started to play a game where we could ask each other sexual questions and, if we couldn’t answer, you had to drink. It turned out to be useful later on in the night as we were asking questions about favorite positions, where we loved to be touched, hard stops, fantasies, etc. Eventually, he gently suggested that I suck on his cock while I think I thought about what my next question should be. I happily obliged and gently put his semi-hard cock into my mouth slowly and gently. A deep groan came from his mouth as he growled, “fuck. Yes.” I continue to slowly suck on his dick, feeling it grow inside my mouth as I, myself, was becoming wetter. I sucked his cock for about 15-20 minutes until the food arrived. He went to get it and left me with the direction of “having less clothes on when he returns.” So I took my shirt and bra off.

Jake came back, put the food in the kitchen, and returned to the bedroom. I continued to suck his cock while he fingered me. He slipped his fingers inside me and knew exactly where to hit the spot and went to town finger banging me. I had to stop sucking his dick bc I was about to explode. I could feel my pussy dripping as he continued. He stopped RIGHT before I squirted so we could prep the bed.

Once the bed was prepped, he told me to get into doggy - my favorite position. I obliged and he slowly slid into me, as we both groaned with pleasure. For the next 15 minutes, Jake fucked me like this, but while varying his speed, pressure, rhythm, etc. When he would just put his tip in and fuck me like that, I was begging for me. He would shift between that and move to pounding me hard. Jake would alternate between slapping my ass, spreading my cheeks, holding my hips and putting pressure on my lower back. I lost count with how many times I came, to be honest.

One thing that I have never truly had the opportunity to enjoy was anal. I have had it before, but it has been painful and not as enjoyable as I had hoped. We had talked about this prior to playing and Jake mentioned that he loves anal but he also knows the approach to it. He said there is a method to do it safely and in a way that, ultimately, is enjoyable. I was intrigued when he told me that, but told him we would have to work up to that.

Well - fast forward to 20 minutes in - and I wanted it. Jake had repositioned me to prone and has started fucking me again. He was moving his thumb around the outside of my ass and I was moving my ass in a way that would guide his thumb in. He took the signal and started to work some lube on my ass so he would use that hole. With his finger, he slowly worked his way in while fucking my pussy. The sensation was…amazing. I was moaning and begging loudly and he was groaning and moaning - equally turned on.

Slowly and gently, with lots of lube, he worked his cock into my ass. Jake was gentle and slow, while rubbing my clit. Admittedly, I was nervous about anal, so I was unintentionally stiff. Jake reminded me to relax, and after a few gentle thrusts, I was able to relax my body and mind and truly enjoy the experience. Again, he varied the angle, pressure, motion and it was jaw dropping. I could feel my pussy dripping as he fucked me in the ass.

We fucked for about 45 minutes before ending dripping wet with sweat and exhaustion. The bed was…a sign of a good time. I was slightly self concious about it, but he was so open and prepared for it, that it made it easier to deal with. I ended up taking a quick shower to clean up while he cleaned up the bed. When I was done, he showered and we finally ate dinner.

A few things really stood out to me about this experience: - being with someone experienced and used to the lifestyle does make a difference - Being with someone who took the time to learn and understand me, sexually and personally, made a huge difference. - When I was able to truly let me guard down, I’m able to thoroughly enough an experience that is normally anxiety-inducing for me. - The sex was amazing. This was the first time in the LS that I was able to really fuck someone without that emotional investment. The emotional piece usually causes me to catch feelings which is tricky. This approach, while based on trust and openness, is what the LS is about for many people…and I completely get it now. - I am excited for our next round - whenever that may be.