[m]y first online hookup

I have been in a very vanilla relationship for the past 4 years (since high school). She has never been into trying kinky or new stuff during sex and I have always been curious so I got on fetlife and decided to test the waters. I ended up meeting a woman ( we will call her J). We end up messaging a lot on kik and decide to meet up. So far from our messaging and exchanging pictures, she has a lot of things I find attractive: she’s shorter than me, she’s blond, and she is thick. So we agree on a time to meet up. She ends up being almost an hour late to the restaurant. I never went in due to having to go back to work really soon. She showed up and greeted me in the parking lot. She apologized for being late and we engaged in some small talk. I said I couldn’t stay long and needed to go back to work. I could tell she was upset for being so late so I said “I do have a back seat ya know” she said “ok let’s go”. We get to the back seat of my car and immediately begin making out. I grab her tits and feel up her body and slide my hand up her dress to start fingering her. Then I remembered she was into being a sub. So I pull down my pants and grab her by her throat and say “show me what you said your mouth can do” and shoved her face onto my cock. She immediately starts sucking. Using her hand to move along with her mouth. I’m grabbing the back of her head and then proceed to put both hands on her head and fucked her mouth. It had been a while since I’ve had a good blowjob so I got close to cumming really fast. I told her I was about to cum and she kept sucking until I came in her mouth. She swallowed it all while still sucking my dick. I pushed her on her back and began to fuck her drenched pussy hard. Next thing I know I’m close to blowing my load in her so I pull out and end up doing it in my hand. I clean up with some napkins and we get dressed again and I head back to work.

[M]y first anal play

So to start, no I am not gay but this will make you question that lol. So about 3 years ago, some buddies of mine gave me a huge black dildo as a gag gift. I kept it as a joke and show it to people randomly.

So recently I have been taking an interest in anal play. So when I was masturbating today, I stuck a finger in my ass. It went in easily amazingly (this is seriously my first time trying this) I start trying to push my prostate to make my orgasm a lot better but it wasn’t working out to well. So since I was about to shower, I decided that I was going to get the dildo and see if I could get it in. As an experiment.