This is the first fully true story I’ve written (minus details needed to keep everyone’s anonymity) to the best that I can remember it. If you enjoyed it, I'd love to know what you liked about it in the comments or privately!
My wife and I engage in ethical non-monogamy. What this has meant for us and how we’ve done it has changed and evolved over the years. This was one of my first experiences a few years ago.
We had set up separate OkCupid accounts and, as you’d expect, the number of women reaching out to a married man with kids in his 30s was fairly low, even with all the advantages of NYC. I also decided not to use a photo that would reveal who I am, mostly to protect my kids until they were old enough to understand. And of those who did reach out to me, many either hadn’t read the profile initially, or were disappointed to learn that I wasn’t cheating. One day, however, I logged in to a waiting message from a cute mid-30s black woman named Rachel.
We chatted briefly in OkCupid before moving over to text messages, which is always a good sign. We seemed to be hitting it off. I shared a full-face picture with her, and she thought I was cute. She was clearly intelligent (and not just because she found me cute!) and was finishing grad school. I found out she was the secondary to another man in a poly relationship although she only saw the man occasionally. We agreed to meet up at a bar in between us in Brooklyn in a couple weeks when we both had the time.
We met, had some wine and some snacks, and chatted. She was more beautiful and sexier in person than I expected from the photo she had shared. She was several inches taller than me, in good athletic shape, with gorgeous long brown hair. Her legs had some muscle on them, she probably was a runner, and her large mouth and thick lips made me think dirty thoughts.
But it was also more awkward than I expected, and I wasn’t sure if she liked me or not. But we had good conversation, spending a lot of time discussing books, culture, and everything we thought about non-monogamy and how the culture viewed it. The meeting was intentionally short, I had to get back to watch the kids, and I had already decided in my head that maybe the night hadn’t gone well, despite the good conversation.
I offered to walk her home and we talked on the way back to her place. Outside her apartment building, I asked, with little hope, if she’d like to meet up again? To my surprise, she smiled and readily agreed. It seems she had thought that I wasn’t into the date either and didn’t expect me to ask. Before I knew it, we were making out on the sidewalk and running our hands over each other’s backs. Well this was a surprise. We sat on a bench and made out a little more.
Then, I stopped her, “I’m really sorry. I really do have to go,” I said, “I’d stay longer if I could.”
She responded by slowly running her hand from where it was placed on my leg onto the erection pushing out of my pants. “Damn it, are you sure?” she asked, smiling, and looking me in the eyes.
Sadly, I was, and we soon left each other. We scheduled another date to meet up, this time planning to watch some Netflix and order some food.
On my way out that night, my wife gave me a kiss and pinched my butt. “Have fun,” she said smirking at me. “Did you remember the condoms?” she asked. I nodded affirmatively. Of course.
Rachel met me at the door with a sloppy kiss and a slight taste of whiskey on her lips. She offered me some and I accepted. It was a good whiskey. We settled down onto the couch, placed an order, and then started talking while we swiped through Netflix. There was a bit of sexual tension, but neither of us chose to make a move, opting to talk a while, and enjoy our whisky. Finally, the food arrived, which we consumed watching some sitcom that I don’t even remember.
When we finished, Rachel tilted her head back and finished the rest of the whisky in her glass. She filled my empty glass up again about halfway and said, “You should finish that,” and then looked at me and bit her lip. I did. She kissed me, pushing me back on the couch until she was on top of me. I kissed back. She kissed differently than I was used to, but it was very hot. We remained that way for a while and then I started running my hands over her body, her ass, and her sides, slowly moving up her stomach and over the sides of her breasts.
She started unbuttoning my shirt while kissing me, giving me more access to her breasts underneath her shirt. When she finished, she sat up, lifted off her shirt while I did the same. I reached around her and undid her bra, immediately cupping her bare breasts with my hands. They fit my hands well, with large dark areolas, and long, sticking out nipples on her breasts. I licked them and Rachel moaned and started grinding herself against my pants. We continued to explore each other with our tops off for a while, and then she stood up and grabbed me by the hand and brought me into her bedroom.
We kissed by the side of the bed and unbuttoned each other’s pants they fell to the floor.
“Do you have any condoms?” she asked. I nodded, pulling out a stack of them. “Thank god,” she responded.
Eventually we were able to get each other fully naked, my hard cock sticking out and into her hand, my hands roaming her body all over. Her pussy was wet and neatly trimmed with a landing strip on top. I pushed her onto the bed and continued to kiss her. Our tongues played and ran over each other’s lips and teeth. I moved on to her neck, then her shoulders, then her breasts. I stayed there for a while, enjoying the novelty of her large nipples in my mouth and sucking on them.
“Bite them,” she urged, moaning. I had only ever tried that with my wife, and her nipples were too sensitive, so I did it very tentatively and softly. “No, bite them!” she said insistently. I bit them and sucked on them. Rachel let out a deep moan. My cock was throbbing, but I moved down from her breasts, glistening from my spit, down her athletic stomach to her legs. I kissed down her legs, kissing and licking almost to her ankle and then bringing myself back up on the inside of her legs. Rachel wiggled some as I got close to her pussy and the smell of her sex was strong and wonderful. I took a minute to lick and kiss around her, running my tongue between her thick, sexy labia.
I penetrated her vagina a few times with my tongue, tasting her before running it over her clit. I was surprised too at the size of her clit. I knew that a woman’s clitoris, like everything else, could vary, but this was the largest I had ever encountered. It made it easier to lick and suck and rub, and Rachel moaned and moved in enjoyment. She ran her hands through my hair while I continued to pleasure her clit. I moved one of my hands up her leg and then entered her with first one, then two fingers while I continued to lick her rhythmically.
Suddenly, she grabbed my hair and moved my head to the side, much more suddenly than I expected. “Huh?” I basically said in confusion. I looked over at her and watched as a liquid literally squirted out of her right at where my face had been just a moment ago.
“Sorry,” she said, looking embarrassed as I brought my face up to hers.
“I didn’t tell you, that… sometimes… I squirt” Rachel said a little shyly.
I smiled. “That’s awesome,” I told her and started kissing her, the smell and taste of her still all over my face and beard. We kissed with our naked bodies pressed against each other and she quickly relaxed again, forgetting her embarassment.
Soon, she pushed me back and started playing with my cock with her tongue and lips. She was good at it. She took my cock into her mouth, and she took it all the way into her mouth. She put her hands on my thighs and started bobbing her head up and down on my cock. It was amazing feeling, her wide mouth and thick lips increasing the pleasure. I laid there for a little bit, just appreciating the feeling. I noticed Rachel was looking up at me while she sucked me. That was sexy, my god.
I could feel myself getting close and had to make a decision. “I want… to come in your mouth.” She stopped sucking for a moment to look at me, smile, and nod, and then run lips ever so slowly over my cock. It wasn’t long before I came. Rachel kept her mouth on my cock while it came, more than I usually came, and remained there while it continued to throb. Finally, she swallowed, got up and kissed me.
After more kissing, she got up and got herself some water. We kissed again and laid on the bed. I ran my hands over her, exploring her body. Soon we were full on making out again and I went down on her again. Within minutes she grabbed my hair and said, moaning, “again, I’m going to again.” I nodded but stayed where I was. This would be interesting.
She grabbed my head more frantically, trying to pull me away, but I kept licking her. “Oh my god fuck yes,” Rachel practically yelled. Her body shuddered and suddenly it started squirting at me in the face. I put up my hand to block it and kept licking her, liquid dripping off my beard and face and hand. She continued to moan and shudder and soon squirted again. Everything was soaked.
“OK, I want you in me now. Where are those condoms?” She asked. While I slid off the bed to grab them, she said softly “Nobody ever keeps going. That felt amazing.”
We slid the condom on my cock, and I started fucking her. I fucked her on top. She fucked me on top. I fucked her from behind. With her back on top of me, I grabbed her breasts and brought them to my lips, giving her nipples a bite again. “Yes,” she said, barely. “Yes”
I kept sucking and biting her nipples while she ground herself into me ever harder. Rachel put my hands back on her breasts. “Squeeze them. Hard”
I nodded, squeezing them with what I thought was decent strength.
“No, really hard.”
I squeezed them harder than I’d ever squeezed a breast before, certain it must be hurting her, but she just started moaning and gasping and grinding into me harder.
“Don’t stop,” she said, while I kept my grip on her breasts. Soon I felt her pussy squeeze my cock and a new rush of warmth and wetness run over me as she squirted again. She laid down on my breathing heavily. She kissed me gently, my hard cock still in her. We laid there together, not moving for minutes.
Rachel slid off me and then turned away and got on her hands and knees, pulling me up to her. I started fucking her from behind and she started really rubbing her ass against me and slamming into me hard. I felt more liquid trickle down her legs. I grabbed her ass and continued to pull her against me. She didn’t stop, her ass massaging me as I fucked her. She buried her head into the bed and started rubbing herself with one of her hands, her fingers brushing my cock. She gasped again and pushed herself into me hard and I could again feel her pussy contract tight around my cock. That was all I could handle, and I came pulling her into me again at that moment.
We lay on the bed, soaked in sweat and sex juices, catching our breath.
Afterwards, we took a shower together, I couldn’t go home to the babysitter smelling like I did (or maybe that would have been another story!), relaxed on the couch for a while enjoying more Whiskey, before I went home.
We met up a few more times after this, before deciding to part, but I’ll always remember the woman who introduced me to squirting.