There was a time when Craigslist had a hookup purpose. Yeah you had to weed through spam, credit card scammers, dudes posing as chicks, and pic collectors but goddamnit if you were diligent, you had a real chance. I met some really cute girls there including Diane.
We corresponded for a day or so after meeting on the casual encounters section. I was 33 at the time and she was 34. She was petite, very tiny, maybe 5 ft tall and 95lbs and looked cute in the pics we exchanged. She was mixed Latina and white so she had a nice natural tan and we met on a warm spring day for lunch at a local sub shop called Thundercloud.
After lunch, we took a stroll around the nearby park / lake where the convo turned more sexual. She seemed so reserved but she had replied to essentially a hook up post I made (a rarity as I usually preferred to reply rather than post) so I figured I would at least toss out the idea of stopping by my place… she was down and it was only about 5 minutes away so she followed me home to my condo.
Once inside it was straight to the bedroom where we laid on top of the covers and playfully teased each other as the tension began to build. We had only met an hour beforehand but here we were in bed. I toyed with her long brown hair and rubbed her legs leading up to her pink denim mini skirt and white tank top progressively getting a little higher on the smooth skin of her thigh.
Diane returned the favor, caressing my legs and we began to kiss softly then more passionately as she delicately touched the bulge forming in my shorts.
The next few minutes were a blur as clothes hit the floor. I slid my middle finger into her dripping wet pussy while I kissed her neck and sucked on her perky little boobs. She rolled me onto my back and positioned her tiny body between my legs. My rock hard erection pointed at the ceiling was hers for the taking and take she did…. every inch of it into her mouth. She devoured my cock, alternating between softly kissing and tonguing the head, gazing up at me for approval of her head skills, and aggressively deep throating me.
I easily could have blown my load down her throat but I wanted to fuck her so I tossed her tiny body to my side and rolled on top of her. I slipped a condom on from the night stand and positioned the tip of my dick to enter her little pussy. It seemed like it was as tiny as the rest of her. She helped me work my dick inside of her and we started to find a rhythm. I was worried about hurting her, holding back a little and I think she sensed some reservation on my part to really give it her (for perspective, I’m an athletic 6 ft, 200lb white guy so twice her size and have a thick cock). She sexily assured me she could take a pounding and not to worry. “Wow, okay. This chick is fucking sexy,” I thought to myself as I began to get more aggressive thrusting into this pint sized good girl gone bad. She moaned in approval, the harder I gave it to her, the more she seemed to want it.
I needed to cum so badly and she knew it. Finally I released my swimmers in the condom deep inside of her and collapsed, both of us sweaty and exhausted.
We had spent an hour at lunch and then another hour having naked fun. I don’t think either of us had really known what to expect nor did we know where to take it from here.
We got dressed and I returned to my office with a big smile on my face. Later that night I discovered her necklace on my nightstand. Ironically we had actually joked about her “forgetting” something at my place earlier. I texted her and she **swore** she didn’t do it on purpose. In any case, I met her the next day at a downtown bar to return it. After a drink we walked to our cars in the parking garage and being the nice guy that I am I offered her to hop in my backseat for some slutty fun. She agreed with absolutely zero hesitation, what girl!
I had a fairly big back seat, tinted windows and the garage was pretty quiet… within a minute she was slurping my cock in the backseat. I pushed her off of me into the other seat and slid her shorts and panties down and flicked my tongue on Diane’s clean shaven pussy. She was already soaking wet and moaning softly in ecstasy. After a few minutes we were both eager to get to the main course. I slid inside her and we went at it hard. Suddenly the stairwell door swung open nearby and we paused momentarily as voices got close then disappeared in the distance. Back to the action and it was super hot after nearly getting discovered. I plowed into her and released again inside the condom.
After that, I kinda lost touch with her. She was going through some fucked up emotional shit. She had a daughter when she was in her teens and had recently been living with a guy that started fucking her 18 year old daughter too.
Maybe 6 months later she texted me that she needed to blow off steam and wanted to come over to my place. She even specifically said she can’t have sex but would love to come over and blow me. How could I turn that down? That night she stopped by and we caught up a little… maybe 5 minutes worth of chit chat before she had my penis in her mouth. Her oral skills were just as I remembered but this time I knew I was going to get to cum in her mouth. I laid back on my couch and let her work me for a good 15 minutes before exploding in her mouth. Diane didn’t miss a beat swallowing it all with a smile and staying on me til the last spasm.
We had sex every few months for the next year. It was low key, no pressure, just every so often when she needed an escape. She knew she could count on me for some laughs or a drink or a hard penis with no judgement or expectations. She was a cool chick and I gave her what support I could and hope things got better for her.
**If you’re a cute chick in #Austin and want to play, DM me.**
Source: reddit.com/r/gonewildstories/comments/eeb9oc/met_a_girl_on_austin_craigslist_fun_ensued