First post here. I love reading other’s stories and decided today I want to start sharing my own. It’s a long story, so skip to ***** if you’re just here for the juiciest details. I’m also new to writing like this, but I hope you enjoy my recollection of events.
I’m 27 now, but this happened 5 years ago just after I graduated college. At the time, I had just gotten out of a serious long-term relationship of 3 years. So, It had been awhile since I was in the dating game. I started by hopping on a famous hook-up app. I’m 6’2” dark brown hair, bright green eyes, with an athletic build. I didn’t have much trouble getting a few matches to start chatting with. I didn’t realize how much I had missed sexting until I started up with these 3 women. After having some fun, one really rose to the top. Let’s call her Jaz. Jaz was Latina, 5’4”, deep dark eyes, long black hair, 32C, fit, with the best ass I have ever seen. I couldn’t believe the conversations I was having with Jaz. She was incredibly sexual, which is something I hadn’t experienced up until this point. We spent days flirting, chatting, and sexting with each other.
On day 2 of talking, Jaz and I made plans to meet up for a whole weekend starting on Friday. I felt it was a little risky going away with a girl I had never seen in person, but we started snap chatting and FaceTiming, talking about where we worked, our hopes and dreams and all that. Even if it was a bad idea, I was definitely planning to do it. We found a nice resort hotel where we could spend our time.
On day 4 (Wednesday night) of chatting, Jaz sent me a picture of some new toys she had received in the mail. There was a smattering of fun looking toys and games that Jaz picked up for our weekend of fun. The toy that caught my eye most was a jeweled butt plug. I told Jaz to put it in her purse for me without asking questions. We had been talking for awhile at this point, so I knew she liked to be ordered around. We spent the night sexting back in forth talking about all the things we would do over the weekend. We were both incredibly horny and excited to explore each other. Skip to the next day.
On Thursday morning, Jaz and I started chatting. She sent me snaps of several of her outfits and asked me to pick one for her. I chose a tight tan office dress that looked amazing against her dark skin. I told her to skip the panties for the day and wear a thin bra. She was nervous that her nipples would show through her dress at work, but ultimately, she obliged. I facetimed her before she left for work and gave her commands to play with herself. I got her incredibly close to cumming and then told her to stop. Get up. Go to work. As frustrated as she was, she pulled down her dress, stood up, looked me in the eyes, and said “yes, daddy” and hung up.
Now, this was the first time anyone had ever called me “daddy” and I had no idea how much I wanted to hear it. I was incredibly horny at this point. I worked from home at the time, so rather than working, I continued to text Jaz while she was at work. We continued to talk about what we would spend the weekend doing, both sexual and otherwise. By 11 AM, we had both gotten incredibly horny. Jaz sent me a snap from her office bathroom with her top down and her dress pulled up with the caption, “do you like your choices, daddy?”. In the photo I spotted her purse and remembered the butt plug I remembered telling her to put in there the night before. I told her that I liked my choices very much and asked her to put the plug in for me. She was nervous to do it at work, even more nervous that she would soak through her dress while sitting with it in. She responded, “uhhg”, but 2 minutes later she sent me a photo from the bath stall with the blue jewel plug in. When she went back to her desk she sent me another photo from under her dress showing off her soaking pussy (to this day, it’s the best picture I have ever seen). I asked her to start touching herself at her desk. “Uhhg” again, she couldn’t say no.
Jaz was a receptionist at a real estate office and said people regularly come into her cubical for supplies or to the front desk. While we were chatting, she said a women walked in behind her to grab some sanitizing wipes. I could tell the excitement of getting caught was turning her on, so I asked her to take lunch in her car. At this point, I had a plan to go see her, I already knew where she worked which was only about 10 minutes from my apartment. She obliged and went out to her car, letting me know she’s pretty sure everyone in her office knows that something is up.
While driving to her complex, I started to send voice commands. I told her to drive her car to the most inconspicuous area of the lot. She worked at a large business complex, so it was pretty easy for her to get away from her coworkers coming and going, but overall, the lot was still pretty busy. I told her to get in her backseat. She sent me snaps of all the people walking through the parking lot, worried someone would see. I told her not to worry and to pull up her dress, again giving her voice chat commands on how to play with herself. I spotted her car and pulled up beside it in my truck. Her windows were dark, but I could see her in the backseat, legs spread, phone in one hand, pussy in the other. When she saw a truck pull up, she shot up with a terrified look.
*****
I stepped out and as soon as she realized who it was, her look of terror turned into a devilish smile. She was clearly surprised and happy to see me. This is the first time I had seen her in real life, she was as beautiful as her pictures. She unlocked her backseat door, pulled down her dress and shot up to me, embracing and kissing me intensely. Biting at my neck, wrapping her legs around me. I slowly set her back down on her seat, still making out intensely. I slid my hand up her tight tan dress, as I went toward her pussy, my hand brushed against the plug in her ass. She moaned. She whispered in my ear that she was so happy that I showed up. I slid into the backseat and closed the door behind me.
I was straddled over top of her, with her dress pulled up I fingered her pussy. While I did my knuckles were brushing up on her plug, every time it hit she would moan. Next, I flipped her onto her knees. At this point, I was pretty visible from the back window, but didn’t care. I pulled the dress up fully over her ass, getting my first amazing view of her ass IRL. The blue jewel plug was more beautiful than I could have imagined. At this moment, I was blown away at the situation I was in. Hornier and harder than I could remember.
I slowly played with the plug, tugging and pushing. While I did, I slid three of my fingers in and out of her tight pussy. After about a minute, I pulled the plug slowly out, continuing my pace in her pussy. When I pulled the plug, her asshole just snapped shut giving me an idea of how tight it was. I was in awe staring so closely at her pussy and asshole. I dove in and started licking her tiny asshole. She loved it. Her moans turned even more primal.
She started rocking her hips back and forth, fucking herself with my tongue and fingers. I could tell she was close. Not a minute later she was cumming, her pussy clenching hard around my three fingers. Her asshole convulsing. I was in heaven, savoring every moment. In all honesty, I felt like I could cum right then.
Shortly after her orgasm stopped, in a breathless voice, she asked me to fuck her ass. She turned around and began giving me the sloppiest blow job if ever gotten. She immediately deep throated me and gagged. While she bobbed, she stroked my shaft, fully covering my cock in her saliva. It had been awhile since I’d had sex and I had been sexting with this amazing women for days, so needless to say I was close.
I pushed her back on her knees, spat on her asshole, I used her pussy to wet my fingers and add more lube, spreading it on her hole. Then I started to press the tip of my dick in. Slowly at first. It was the tightest hole I’d ever felt in my life. Jaz moaned hard as I pushed in. Her blowjob added a lot of lube to my rock hard cock. A few slow attempts back and forth and I was finally sliding about 3/4 of my cock in and out.
Her hips rocked, she began using my cock, just like she used my fingers a few minutes before. I reached around and rubbed her clit. She loved it, moaning, “yes, daddy, please fill me. Please give me your cum”. That is literally all I needed to hear. I slammed into her fully, shooting ropes of cum deep into her tight ass. I came harder and more than I ever had in my life in the backseat of that car. Jaz began to cum seconds later. I felt her squeeze every last drop of me into her. She fell face down toward the backseat, my cock still in her ass. It pulled me forward on top of her as I pulled out. I saw a tiny drip of cum on the outside of her asshole. Imagining how much was inside her sent me over the moon.
Still laying there with everything exposed, Jaz grabbed the plug that was sitting on her center council and slid it back into her ass. She said in the most seductive voice, “now I can feel you the rest of the day”. I was amazed. We sat there and talked about how relieving that was and realized that her lunch was nearly over. We kissed again and made plans to meet up at a nearby bar after work and start our weekend trip early.
Jaz and I had a lot more fun for months after this. We opened each other up sexually and experimented with all sorts of new kinks. If anyone is interested to hear more about our experiences, or others that I have, let me know. For anyone wondering, no, Jaz was not caught and there were no repercussions for these actions in the parking lot, as far as I know, nobody she worked with ever knew, with the exception of one of her work friends.
Source: reddit.com/r/gonewildstories/comments/tutxkp/when_i_m_had_risky_anal_with_jaz_f_in_a_parking
Damn, keen to hear about how the weekend went!
Definitely wanna read more about the weekend!