A couple weeks ago, I (30M) took a cute little Asian ~24F out for some cocktails. Within a few minutes of sitting down at our table, her legs were pressed into mine and she made a joke about how hot she thought I was, so I figured the date would go well.
We finish our drinks and lean in for a little make out at our table. She stops after a couple minutes to tell me how hot I am and how into this she was. I go get us another round to let her cool off, but we pick up where we left off when I returned with a second round of drinks. We down our cocktails between makeouts, and less than 30 minutes after sitting down, she wants to head back to mine.
I give her a quick tour of my apartment before she heads into my room and strips off her clothes before jumping in my bed. I leave my pants on and climb into bed and continue making out with her as my hands wonder down to her pussy. I rub her clit until she asks me to slide my fingers inside her, and she moans heavily as my fingers stroke the inside of her tiny little pussy. She slides her hand down my pants and takes a little feel before stopping to say “dude…you’re huge”. I help her get my pants off and she asks what I need, so I tell her “I want you to use your mouth on it”. She repositions herself so her head is between my legs, but she was not used to someone as girthy as I am, and could only get the tip of my cock in her mouth before she started gagging.
I got bored of the gentle sucking, and we agreed to fuck if I used a condom, so I repositioned her in missionary. It took a lot of gentle easing, but eventually the tip of my cock penetrated her, but she yelped if I tried to push anymore of me inside of her. After a few strokes and me trying to go deeper, she asked to stop said I was waaaay too big for her. I helped her get dressed, and she said she was super horny, but my dick was just too big for her to enjoy.
A blessing and a curse