I met Darren after a meeting with a client in their San Francisco office. I was making idle chitchat about dead celebrities and upcoming music festivals when he walked by. He stopped to add in his two cents. I had never seen him before, as his department was unrelated to my visit. Darren was tall at 6’3″, lean, stormy blue eyes, a slight facial scruff, and spoke with an incredibly thick Irish accent.
As I stepped in the elevator to get back to my office, Darren jumped in at the last second to join me. He asked about my weekend plans (I had none) and then asked if I’d like to have a drink with him on Saturday.
I was surprised at how forward he was and after looking at him for a moment I said he may be too young for me. After asking my age (43), and seemingly genuinely shocked, he told me he was 29 and that I should at least have a drink with him. He was new to the city and hadn’t really met many people outside of work. By the time I made it to the building exit I had relented.
Saturday night while I was walking into the pub to meet him, the bartender was studying his ID, which apparently was his Irish drivers license. It took the bartender a moment to find his birthday and when he did, he read it out loud. Within the first two minutes, I caught Darren in a lie. He wasn’t 29 at all- he was barely 21, exactly half my age. I thought about leaving but I had already gotten dressed and drove from the 45 minutes the east bay to meet up.
We decided to take an Uber to a new bar, and we shared the ride with two older and definitely wild women. They turned our ride into a party and as they were the first to be dropped off, they invited us to party with them. We stopped at a huge Victorian house off Haight where they said there was a hot tub, a lot of alcohol and some other party substances, and being that I was already with a complete stranger manchild, why not.
Inside, we started doing shots, rolling joints, and bumping a line or two. These ladies were out for extreme fun. As delirium started to hit, they went to the back of the house, got naked and jumped in the hot tub. I followed their lead.
Darren stood there trying to figure out what to do and decided, fuck it, got naked and jumped into the hot tub too. I honestly didn’t have anything sexual in mind, but Darren thought otherwise. Hidden by the bubbling jets I felt his hand squeeze my thigh. Instinctively, my knee moved closer to him, spreading my legs apart slightly. Without missing a beat, his hand quickly slid up the inside of my leg until his pinky was just grazing the lips of my bare pussy.
I tried to play cool in front of our naked hostesses, and even though I was shocked by his bold move, the mix of alcohol, pot, coke, and hot tub had me stirring in every sort of way imaginable. His hand turned inward to cup me, and I felt his finger hook and slide between my lips. As he probed in and out of me, I felt myself close my eyes and sink into the tub. His finger found my clit and began quickly teasing it. By this point, it was fairly obvious that something was happening under water, and our rambunctious hostesses made a comment about an empty bedroom if we wanted to use it and got out of the hot tub to leave us alone (and pour more shots and do more lines).
The heat of the hot tub started to get to me so I moved to sitting on the outside ledge. Darren stood up and moved to face me and moved in to kiss me hard.
“I want you,” he said with a breathy determined accent.
We moved out of the hot tub, grabbed our clothes, and ran dripping into the house, finding our way into an empty guest bedroom. As we dropped our clothes onto the floor, it was my first time really seeing him fully naked in front of me. His body was athletically lean and lanky with very little body hair. Naked he definitely looked his age. His cock was long and semi soft, probably because we were suddenly cold from being wet without towels.
He pulled me into to the bed and we got under the covers to warm up and began kissing again. His head started to travel down my body and his mouth found my breasts. At this point he seemed a little loss on what to do next, again, a telltale sign of his young age.
“Bite my nipples,” I directed. “Harder. Hurt me. Yes. Just like that. Now put your fingers inside me and fuck me hard with your hand and don’t stop.”
Darren listened to every word I said and began to take cues from my body when he was getting it right. I could feel heat of my body rise as it began to tense up around his fingers.
“Darren look at me right now. I want you to look at me while I cum. FUUUUCK!!!”
Suddenly, the intensity of it all, my body released into a puddling wet orgasm all over a stranger’s spare bed. Darren’s dark blue eyes were wide and bewildered. He began to stroke his now hard cock, and I told him to get out of the bed and stand up. I sat at the edge of the bed and put his uncut cock in my mouth. I worked the tip with my lips and circling his foreskin with my tongue before working my mouth down his shaft. He wrapped his hands in my wet hair, while thrusting himself into my mouth.
He then pulled his cock out of my mouth, and flipped me onto my stomach, ass in the air, and suddenly I felt his cock sliding inside me. He began to pound me hard and fast. Almost a little too fast- like an eager jack rabbit. Again it was time to direct Darren into how to properly fuck so that two people can enjoy it. We took turns asking for what we wanted, switching positions, and being audibly loud when it was feeling amazing. He found the right positions inside and soon he got me to cum all over his cock. And when he was ready to cum we switched to missionary so that again I could look him in the eyes, this time, while he came all over my stomach.
Darren managed to find something to clean us up, and as we began to refocus, we heard multiple voices laughing over loud music. Except. It wasn’t just two women. A small party had sprung up in the house while we were fucking. We threw on our clothes and straightened up. We cautiously entered into the main part of the house where our hostesses were partying it up with 4-5 more friends. No one gave us an odd look, or teased us about what we had just done. Instead, casual introductions, new drinks, and a freshly sparked joint made its way around, like it was just another Saturday night in San Francisco.
Source: reddit.com/r/gonewildstories/comments/618mb5/this_is_the_story_about_a_first_date_that_turned
Nice
Good ok city parties. Sounds like a blast
Lucky boy.
Damn that’s hot as fuck! Love cougar sex!!!
First date? Is there a part two to the story?
And this, ladies and gentlemen, is how women will rule the world. They will find the young and train them in the art of life and demand nothing less than perfection.
Have you been with any younger men since?
Great story! Very enthusiastic to read. :) hope to hear more stories from you.
Great story. Glad you took the reigns to teach this young stud, he’ll be a great lover for others to enjoy
That was hot! As are you! You should write more stories…
After reading your story and seeing you past posts, I have determined, in my opinion of course, you are incredibly sexual/sexy and your past pics stir an incredible desire. As a man, slightly older than you, I can say I am utterly turned on by your prose and you pics… well done in deed! (insert golf clap here)
How big is your penis, man who wrote this?
Love the story, sounds like you had quite the night. I especially love the bits of dialogue you added into the story, especially the part of you directing. Being someone who loves older woman, I love stories like that. I would love to have a wild night like this with you ;)