I am 37 and recently divorced. The dating scene as a late 30s divorcee armed with dating apps is more nuts than it was at any point in my 20s. As with so many divorces there was a pretty significant dry spell in the bedroom through the later portion of the relationship. This is the story of my first encounter as newly single.
Eventually I decided I was ready to start dating so I did what everyone in the 2020s now does, I downloaded some apps. I started with Bumble and Tinder and eventually learned how the game is played again. One of my first connections on Bumble was with a woman named Allison. Her profile gave the impression of a slightly hippy-ish 41 year old. A free spirit type. Which is definitely not my usual type, but I had decided to expand my experiences and to date women of different types.
We exchanged the usual getting-to-know-the-basics messages and numbers. I texted her to see when she wanted to hang out in person. Her response was “how about tonight”. I responded with “yeah, sure, why not” and I was set to go out with a new woman for the first time in a long time. We settled on meeting at her place and having some wine and figuring out what to do after that. And then she texts me one more time and says “oh, and wear something with buttons”. So internally I’m thinking, ‘hmm, that’s interesting’.
I eventually show up at her address and text my friends where to start the search if I disappear (be safe out there y’all). She is about 5’5″ with long wavy brown hair and pleasing curves underneath a casually sexy black dress. We sit down and chat for a good while and eventually end up out on her balcony at sunset. Allison was giving me what felt like signals as the rust on my skills was slowly being worked off. I stand behind her and wrap my arms around her to kiss her cheek. She turns around in my arms and we start to makeout.
It wasn’t long after that I learned why she wanted me to wear buttons. She started undoing my shirt as we made our way kissing into her bedroom, seemingly relishing each stage of my shirt coming undone. My hands were not idle either as we each ended up mostly undressed on her bed stroking and squeezing each other in places newly accessible. I ran my hands down her sides, stroking her breasts, squeezing her ass and holding her hips firmly. I took my opportunity to kiss down her neck, along her chest and ending at her nipples where I used my lips to rub, squeeze and suck her nipples while my tongue explored the now firm nubs inside my mouth.
A glimmer then came to her eyes and a smirk to her mouth as she started kissing down my chest and stomach while sliding down the bed. She had been lightly stroking me for some time so I was hard as a rock. When her face got even with my dick she said “tell me what you want”. Still feeling like I’m swimming, I told her simply “I want you”. That wasn’t good enough. She followed with “no, tell me exactly what you want”. So I did “I want to be in your mouth”. And then I was. And it was good. She had done this before. But to my frustration it didn’t last that long as she just wanted to tease me for now.
We somewhat switched positions and though she didn’t want me to go down on her (her loss) we did focus on her pleasure for a while. This included lots of stimulus from different sources at the same time. Kissing, nibbling her neck and suckling her breasts was paired with fingers on her clit, inside her and eventually one of her toys from the bedside table. It was my first experience with one of those toys with the tip that sucks the clit. Now I’d like to say I gave her an otherworldly orgasm in no time. In my experience that doesn’t normally happen my first time with a woman. I haven’t learned her buttons yet. But, I did end up finding her buttons after a little exploring and she came hard, arching her back and tipping her head back to the wall.
Next she told me to grab a condom from the same bedside table. At first I declined, still feeling like my feet weren’t quite under me with all this. But a bit more teasing from her mouth and I was always going to give in. Hey. I’m only human. So I said fuckit, can’t be afraid to live a little. I rolled the condom on and she straddled me. She leaned forward, snaked her hand down between us and put my head right where we wanted it to be. She then rocked back and we both savored the sensation. We ended up going back and forth with cowgirl and missionary. Eventually she was riding me while I squeezed her breasts. She looked down and said “they’re pretty good for 41 aren’t they?”. I said “shit they’re fucking good for anyone”. And that was no lie. They were very nicely shaped, and frankly insanely firm for a woman in her 40s. I think the compliment helped put her over the edge (compliment your person, people!) as her back and neck arched again. As soon as she relaxed I rolled her over and was soon joining her in a very fun climax to our evening activities.
Source: reddit.com/r/gonewildstories/comments/xeknfj/fm_wear_something_with_buttons_a_newly_divorced
Hey that’s great! Glad you got back on that horse!