I was wearing jeans and a t-shirt, not gym clothes.
As last time, I was still cautious. When approaching her apartment complex, I still circled the block a couple of times, making sure I wasn’t being followed, making sure I wasn’t driving into a trap. Yeah, a little paranoid, but I was new at this. We’ve all seen episodes where the bad guys went to great lengths to con someone.
How did I know this wasn’t an elaborate ploy of someone for some sadistic fun and games? You don’t think screenwriters make that stuff up out thin air, do you?
After parking, again, at the far end of the apartment complex, so that my car was less likely to be associated with her, I messaged her, telling her I was a minute from the front door. And despite my angst, reduced as it was, I was already aroused. I adjusted myself so that my cock was pointing up, not bent over as it tends to get when I’m seated, like in my car.
Her apartment was on the second floor, but she met me at the front door of the foyer on the front door. I was confused for a second, until I realized she was wearing a skirt that was clearly too short for outside wear. She gave me a big hug and a very long, wet kiss, and reached down to grab my crotch, making sure I was already hard. Then she turned around and walked up the stairs, As I followed, she hiked her skirt up even more, purposely flashing her purple panties at me.
Once we got inside her apartment, she shut the door, I emptied my pockets on the kitchen table, and she led me to her living room couch, the site of our last adventure. This time, though, we didn’t sit down. Instead, she sat down, with me standing in front of her, and she pressed her hand against the bulge under my zipper again, and began moving her hand, stroking me, encouraging me to grow even more.
She looked up at me, purring, and said, “I’ve been dreaming about this all week. Every night when I fall alseep, every morning when I wake up, I think about you and relieve myself. I can’t wait to touch you in person!”
“But first….” she added, taking my hand, and then leaning back on the touch and turning, so she was on her back, lying the length of the couch. She pulled me toward her, making it clear she wanted me on top of her.
Who was I to say no?
I knelt between her legs, her skirt hiking up enough to flash her panties at me again. I laid down on top of her and felt her arms around me. For the first time in a long time, I felt a woman who wanted me close to her.
We hugged and kissed for a while, occasionally groping each other. She kept her legs apart, letting me grind into her, while I kept myself suspended above her occasionally, then letting myself back down to press our bodies against each other again.
I kept grinding, wondering what would come next. I wasn’t ready for intercourse, I was still married, I wasn’t sure if I could go that far. And I didn’t know anything about this woman, how do you bring up the STD conversation? For that matter, she had just turned 50, could she still get pregnant? Those seemed like a lot of worries to deal with in the heat of the moment, and I hadn’t come prepared with condoms.
As with our last meeting, I decided to let her control the pace. I continued our kissing, fondling, grinding, but not taking it to a new level myself.
The more I drove myself into her, the higher her skirt rose, and once her panties were completely exposed, she spread her legs, helping me dry hump her. I imagined her getting wet, that I had been lucky enough to catch her in just the right spot, but shortly I didn’t have to imagine any longer.
Her chatty demeanor as we had been making out and grinding slowly disappeared, replaced by regular breathing that became deeper and more intense, which in turn was replaced by quiet moaning. Our lips spent more time together, our tongues finding each other more and more actively.
I *was* hitting her in the right spot, and it was clear she was enjoying it. And then enjoying it a LOT more. She quietly shuddered, unexpectedly for both of us.
After a few moments, she opened her eyes. “That was new!” A few moments later, she wiggled underneath me, pushed me up, so that I was kneeling above her. She reached for my belt buckle, then unbuckled and unzipped me. Spreading open the sides of my zipper, she ran a finger up and down the bulge inside.
Then she giggled, reached down to her waist, and pulled at her waist. I realized she was tugging the bottom of her tank top out of her skirt, and then after a bit of wiggling, had pulled it all the way up, exposing her breasts. She looked up at me inquisitively, and I reached down and helped her slip her top off over her head.
Tossing her top on the floor, I looked down at her, breasts spread for me, hair spread out over the arm of the couch. She shook her shoulders, jiggling her chest for me.
Then she reached down to my jeans again, and tugged them down a bit, exposing my underwear, and the very visible ridge pointing up to my chest. She ran her finger up and down the ridge.
“I’ve been looking forward to this since you were here last week!”
She placed her thumb and forefinger on each side of the ridge, and stroked up and down a few times.
Source: reddit.com/r/gonewildstories/comments/bq1311/risking_my_second_craigslist_encounter_f_pt_2