Okay so in my home town there was a notoriously raunchy “Steak n Shake” restaurant. The food would sometimes take up to 20 minutes to come out of the drive thru window. Really really bad service, but still very much drawing a crowd. Being open nearly 24/7 also made it the hangout for many high schoolers and young people who were bored of walking through Walmart. I lived within a 2 minute drive, had disposable income and I would often go there late at night (2-3 am) and smoke weed in the parking lot. Anyway…. when I was 18 or so during one such night during the summer I decided I wanted a shake. I pulled through the drive thru. There was a big red headed woman (she was pushing 250-300) who was always my cashier. Extra nice to me always. One night I asked for her number as she hands me my food because I was working on being more assertive with women (lol)
A week goes by of flirty texts and such. She’s 27. Is named Sam. Has a boyfriend who is in jail. Typical shit.
Friday night I pack my bowl and drive to S’n’S to go see my girl Sam. Probably 2 am. I get my stuff. Sam asks if I want her to sit with me in my car. I say yes. She comes out the back door and jumps in my car. We smoke the bowl I brought and talk a bit. I can tell she is really into me. I’m very nervous. She asks me if I’ve ever seen boobs not on a screen. I stutter and say no. She pulls her uniform off exposing her massive breasts. Biggest I’ve seen to-date. The kind of giant boobs you see when you’re discovering porn and are mesmerized by. She definitely knew by my lack of experience she had the upper hand and literally anything she did would blow my mind.
She kisses me and sticks her tongue in my mouth. Weird tongue texture. I aggressively grab her breasts and she stops kissing me and says very calmly in a breathy voice “gentle” and starts kissing me more. Soon I’m sucking and kissing on her nipples. Sometime goes by and she brings moving her hand up my leg. Slowing creeping up towards my very hard cock. When she gets to the tip of my penis pressed against my leg she stops. She pulls away from kissing me too.
Sam looks me in the eyes and says “is this okay?”. Me very horny with probably a very wild look in my eye says “of course” and she pulls my pants down and then being rubbing directly on my underwear. She works her chubby hand into my fly and I feel her fingers touch my shaft very lightly. She pulls my dick out and brings to move her hand up and down. I’ll never forget the smile on her face.
At this point I should be exhilarated. Going further than I’ve ever been. Getting to suck titties. Getting my dick touched. But my mind I was in panic mode. From the time she began rubbing I was worried about cumming too early. I knew that I was not going to have sex because we were in the front of an SUV but I didn’t want to see like a punk and bust my nut 5 seconds in. I think I made it 30 seconds. Just as she put her spit covered palm on my cock I came more than I had ever cum before. It went everywhere. I was very embarrassed and she didn’t really help but said “that was quick and I’m flattered.” Despite coming too quick, I felt pretty good about myself.
She left my car soon after. Probably had a weird shift after that. We met up another time but that was less eventful and the coolest thing we did was smoke weed in the back of the restaurant. She was pretty crazy. Would call me to talk. Dropped out of contact with her. Those big titties made an impression and Sam if you’re reading this thanks for being the first girl to jerk me off.
Source: reddit.com/r/gonewildstories/comments/bvqmpw/steak_n_shake_mf