Alright alright, I know it’s not a mom. But she was older then me, not a MILF (no kids). But fuck it, who cares. It happened and I’m telling y’all about it. :)
Also, I keep saying this will be short and end up writing a mini novel. So in that spirit, I’ll try and keep this short and fail miserably at it.
For context, this happened midway through my daycare career. It was a community centre that had multiple services running out of it. This is a coworker from one of those services (So not a daycare worker herself). We had huge sexual chemistry but didn’t do anything due to work. So this happened as she was leaving to take a job elsewhere.
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Fast forwarding this to our 4th date. We had talked on the phone (no texting remember, 2000s), we were very sexual with each other. On all our previous dates. We had made out in her car. Felt each other through our clothes. She loved to tease, loved it. I was a walking hard on…always was but even more so now that she would edge me. And for context, she said that she was super tight.
We had our fourth date doing a dinner and a movie. She picked me up in her car and drove. We talked very sexually on the ride there. When we got out of the car. She asked me to surreptitiously feel her ass. She was wearing this nice burgundy dress that had a bit of sparkle on it and ended at mid thigh. She asked if I noticed anything. So I made sure to feel and grip her butt and then it hit me. I wasn’t feeling the bands or straps of any underwear. She winked at me and walked towards the restaurant and I was just admiring that ass on the way there. She was Hungarian, white, about 35 years old at the time. She was 5’6, very blonde (whitened-like) hair, hazel eyes. She worked out a lot and had very defined shoulders and arms, A cup breasts. Fantastic ass – sculpted almost. She also had very protruding lips which looked very sexy on her. Also her legs were long, toned and tanned. Made for a great combo. Not the most beautiful, but she was beautiful to me and we had crazy chemistry so far.
Dinner was fine. Lots of innuendo, teasing, etc. Nothing happened.
Went to a movie. Can’t remember the name, it was trash/boring. Not many people in the theater. We were up at the back. Near the end, she took off her shoes. Switched her body to lay sideways with her head and hands on my lap (the arms could swing up and down). I don’t care about this movie when this happens. I start growing in my crotch with the pressure of her head and hands on it. She starts moving her hand back and forth across my bulge. It was very sexy, here I am thinking she is going to whip it out and do something right there. Alas no, she was smiling as I looked down on her…that’s as much as I was going to get. Damn tease.
I very slowly and gingerly ease myself out and walk out of the theatre beside a woman walking with a smug smile knowing why. We get to her car, we talk idly. My hand on her inner thigh, rubbing, caressing. Without any direction from her we go to this abandoned mall parking lot. We start making out again. Her hand reaches out to unzip my jeans and I’m like, fuck it, we are doing this now and I help by undoing the button and rolling my pants and underwear down just below my knees. We continue to make out but her hand is trailing up and down my shaft. Not stroking it, just rubbing it over her palm back and forth. It feels good and I moan in her mouth.
She then gets up, gets on her knees on the driver side seat and bends over to place her face in my crotch. With her hand at the base of my shaft she starts to rub her cheek against my cockhead. It feels great. With my cock never leaving contact with her face, she starts rubbing her other cheek, her forehead, even over her eyes while looking up at me. It’s so erotic. Never had this done before for so long. Every now and then her tongue would snake out and lick my cock up and down before going back to rubbing it vigorously over her face. I tried to control where my cock was going and slide it in her mouth, but she would smile and pull her face back. Then take my cock and slap it against her cheek a few times before going back to rubbing. Clearly this was on her terms.
I was loving all the attention but I wanted to please her too. Knowing she was commando, my left hand reached out under her skirt and started to rub her pubic area. My fingertip found her clit and I started to rub it slowly in circles. She really enjoyed that, her breathing got heavier, she would moan and move her hips in circles to grind against my finger. I increased the pace of my rubbing and she responded by opening her mouth and engulfing my cock halfway down the shaft.
Oh my that felt great. She became motionless from the neck up. Her head didn’t move. Her pouty lips wrapped around the shaft of my cock, her staring up at me. Her tongue licking all over the parts of my cock inside her mouth. Felt so good that I moaned and started thrusting myself into her mouth. She put her hands on my thighs to control how much went inside her probably. It was just so hot to look down on her and slide my cock in her mouth the visual alone was enough to make me throb.
With my finger on her clit, it was getting drenched in her fluids and I took that same finger and slowly slid it inside her pussy. As soon as it started to enter, her eyes closed and her mouth opened in a big moan. I slid my finger all the way inside her….rubbing her gspot. I made sure to run my finger back and forth and hook it to really hit that spot. Her mouth left my cock, she was totally in her feels . She looked at me and saw me smiling down on her like “gotcha”. We were competitive with each other so that renewed her assault on me. She started to go down on me. I mean, really went down. Her head was bobbing up and down on my cock. Going 3/4 down on my cock, popping back up and going back down again on a torrid pace. And never letting go, all her moaning and groaning was done with me in her mouth which made it vibrate and feel much better for me. She was going to win this battle unless I stepped up my game.
I slid a 2nd finger inside her. Holy shit, she was tight. She wasn’t kidding. It was almost a struggle to get 2 fingers inside her. They managed to fit and sink all the way inside her. She was so wet and as I started to finger fuck her more vigorously, she couldn’t take it. Her mouth left my cock and her hand held my shaft in a death grip, seriously, she squeezed it hard. Occasionally stroking it and rubbing it on her face. But she was lost to what my fingers were doing to her. She was moving her hips back and forth trying to get more. What sealed the deal and her cum first was when I moved my thumb up to try and rub her clit. It was awkward with the position we were in but more often then not, my thumb was able to hit/rub her clit while I was thrusting inside her and she gave a half yelp/moan, stopped moving, thighs shivering, head down in my crotch and let the orgasm wave cascade over her.
After her orgasm subsided somewhat, she let go of my cock and sat back down on the drivers seat. I’m sitting there with a hardon looking at her like…umm…hey, I’m still here. Nothing was said but after her breathing return to somewhat normalcy she just declared, we are getting a hotel room now.
So fast forward to hotel room. We are both naked. We have been 69ing until she raises up and switches positions so that her pussy is over my cock. “You ready” she says, I nod. And then she tries to sink my cock inside her. Tried is the operative word. She was wet, she was stimulated, she was ready. It was sooooooo tight. I’m not toilet paper roll thick or anything but damn, it was a struggle to get it in.
It felt like a long time, maybe it was. At least a few minutes, maybe 5. I wasn’t timing it. I don’t care. But eventually I got myself inside her. A lot of trying, a lot of saliva, and sheer determination. What ket me rock hard was her constantly saying ‘your so big, oh your so damn thick’ etc. I’m not, but it was a good ego trip to think so. It actually hurt at first having myself inside her. That’s how tight she was. Both of us couldn’t move at first, we were both feeling a bit uncomfortable. But eventually she started making very minor motions. Just a rocking of the hips slightly. That really seemed to help and get both of us back on track and focused on the sex.
Eventually we got to the point where she was sliding up and down my hard shaft and cumming repeatedly on it. Her extra orgasms helped make it more slick and easier to slid in and out of her. She was loud too, thank goodness for the hotel and not in the car. Having it painful at first really helped hold off my orgasm but it was fast approaching. When it came time I told her I was going to cum (on pre arrangment talks) she got up and laid on her back and I got on top of her and let loose a huge blast on her tummy and chest. I’ve always cum a lot (as feedback from multiple sources) and this was no different. Ropes and splats of cum littered her torso as I came almost violently. It was one of my more intense orgasms.
We did it a few more times that night. Always her on top cowgirl or reverse cowgirl. We struggled in the other positions due to her tightness. But I wasn’t complaining. It was great for both of us.
End of story. As always, comments and feedback is appreciated.
Source: reddit.com/r/gonewildstories/comments/ihs795/mf_daycare_adventures_6_a_coworker
Wow.