[M]y [F]un run in with Jenny with a Y.

Greetings GW Stories, long time fapper/reader first time I’ve had a decent story to share. (please forgive typos, I’m doing all this on my phone)

BACKSTORY
I was recently let go at my job and am starting a new one next week. The last week or two I have been trying to get back into running because I used to be in a lot better shape (mostly from running cross country in high school and college) prior to previous job. There is a gorgeous river walk and running trail about 1/4 mile from my house and I had been running there for the last week, every morning.

The second day I was running and doing the usual runner wave to fellow runners or a polite “Good morning” as most people do. About half way into my 5 mile run, this super cute brunette with short hair crosses my path going the other way. I didn’t really take notice of it. The next day, I’m running and near the end of my run, we cross paths again. I say “Good morning!” with a little more enthusiasm then my previous ones because I remember her. She responds with, “Same time tomorrow?” I chuckle and shout back, “Of course!” The third day comes and we cross paths again, we chat for a little bit but both of us have other things to do so it doesn’t last long.

DAY OF
The fourth day, I run across her about halfway through my run and she is just starting. She asks if I’ll run with her as she would like a pace partner to help encourage her to go further. How could I say no?! I find out her name is Jenny, with a Y, her boss is apparently also Jennie so hence the with a Y. She is probably, 5″ 6′, short, pixie style brunette hair and a nice little body, in good shape and probably DD, but I didn’t ask. She broke up with her boyfriend a month or so ago and has been running ever since to get in shape. I comment on her strong pace throughout the 3 mile run.
Near the end of the 5th mile, I say that I probably should be wrapping it up as I’ve been going a bet longer than her. She says we can just do a cool down lap or two. I gratefully agree and we start to walk and talk more. She asks how far I am from here and I say not far. She asks if I can help her with a cool down stretching as I’m more used to long distance runs. How can I say no?! At this point I had no idea anything would come of this so was a caught a little off guard when we got to a shaded, high tree area near where she parked and took her shirt off, showing only her running bra and her large breasts squeezed inside of the. I must have been staring for a little bit, because I was brought back to reality by her asking if I wanted some water a second time… oops! I say yes and she jogs to her car, her hips shaking a little more than normal and I just keep staring.

She comes back with a large bottle to share and asks me to hold her legs as we stretch out. She removes her shoes since we are in the grass and I follow suit. We start doing different stretches and cool downs to relax our muscles, all the while I start to stare at her more and more. Her sexy tits swaying in the tight bra, begging for freedom, her thick ass bouncing and shaking in her leggings/jeggings/running pants (whatever they’re called)
She had to have noticed my long stares because she asked me to come behind her and help her stretch down and touch her toes. I’m hesitant as I clearly have at least a mid-sized hard on at this point, mostly hidden from my running underwear.

I help stretch her out from behind, and then feel her ass slowly rub against my crotch. I freeze! Stunned at her forwardness. She rubs a little harder and a low moan escapes me. I grab her shoulders and help press her down to almost all the way down and she rubs once more. I was obviously very slow on the uptake, but finally realize I need to make a move.

I move my hands to slowly grab her massive tits that I had been thinking about for so long and start to kneed and squeeze them. Lightly pinching her nipples every now and then. The charade is up, we are both very interested in the other. She start to rub hard on my now almost fully hard cock as my hands move faster and harder on her. I reach one hand down to start to feel her pussy under her pants and realize she has no panties! I move to grab her hips and a moan now escapes from her. Suddenly, she stops. “Wait! Let’s go to my car!” I nearly sprint there and as soon as the doors are closed I grab her and start to passionately kiss and nipple on her. Our hands exploring every little part. I start to finally rub her pussy through the pants and she offers to take them off. I can’t only stare, mouth wide at that perfect little pussy. I humbly ask to taste it and she nods. I slide one finger just through her lips and instantly feel her warmth and wetness. If I wasn’t at full mast before then, I certainly am now. I can’t contain myself and dive down to my knees (giving oral is my favorite!) I grab her hips and pull her slightly off the car seat and basically inhale her now wet pussy. I start to kiss around the lips and spread her wide with my tongue. She tastes perfect and I won’t stop. I see her swollen clit and decide that is my next target! I lightly hold it in my lips as I tongue the fuck out of it. She starts to moan and gasp as I speed up and increase my pressure on it. I grab on tighter as she starts to buck and shake and I keep on licking and teasing her. I long moan and gasp and then a small chuckle and I know that she has cum!
“My turn!” She says. We swap spots and she starts to take my average sized cock in her mouth. Sucking and slurping with so much enthusiasm! I can’t believe this is actually happening and the she stops. I look up and see her standing best she can in her car ready to mount me. I grab her hips and guide her in as she slowly slides onto my cock. One hand is wrapped around her waist as the other plays her her amazing tits while her hands hold the front seats. We ride for a few minutes and then I ask to swap. I place her spread eagle on the back seat, with her legs on the front seats and start to slide fully in and then out, letting my head tease her as I rub her swollen clit. I speed up and feel her start to shake and moan more. I start to slam full force into her, my balls slapping the bottom of the seat, her rocking against the top.
She leans up as far as she can and whispers, “Cum for me!” I fuckin’ lose it! Wave after wave or orgasm bliss shakes off of both of us and I feel her pussy tighten on me as she joins me in cumming.(luckily she’s on the pill)

After a few minutes to recover and clean up best we can. I try and get dressed again and ask when we can do this again.
“I’ll be her most mornings.” she says with a wink. We kiss and part ways. Only after I see her drive away do I remember that I start my new job on Monday and won’t be able to run in the mornings…and I failed to ask for her number….
Fuck me.
Hoping to run into her before then!

Source: reddit.com/r/gonewildstories/comments/6n1ji2/my_fun_run_in_with_jenny_with_a_y