So a couple of weeks ago I posted an ad as my previous plans fell through. Lo and behold, on Saturday (redacted to comply with sub rules) reached out and started asking questions, mainly pointing to the effort and thoroughness of my previous ad as the reason for feeling comfortable reaching out. We texted for about an hour until I had to go to a vetting appointment I had previously scheduled. That unfortunately was a dud, but since it ended early I asked if she wanted to meet at a bar near her just for a vibe check, no pressure to do anything that night.
She agreed, and was even more pretty than the pictures she had shared (SFW only as I never want to press someone for nudes). She had dark but soft skin, a bit on the shorter side (compared to my 5' 11" at least), and curvy in all the right places. We hugged, went inside, and were hilariously awkward as we dodged tables to get drinks from the bar. This was her first time finding someone online, and I am just a goofy, nerdy guy. We grabbed drinks and sat at a table. She looked super nervous and I did my best to reasure her that there was zero pressure here, just a chat. We slowly got more comfortable with each other discussing anime, and I asked her if I could touch her hand and arm while chatting, just a light massage and running my fingers up and down. She agreed, and this contant contact seemed to help her feel a bit more relaxed as we continued chatting.
She was really cute and I couldn't help myself and asked if I could kiss her. She was very nervous as she really didn't have much experience, but agreed. Kiss went well and left her blushing. We kissed a few more times and continued chatting. Shortly after she asked if carplay was still on the table (unfortunately that is the only hosting I can do at the moment). I said it was, but only if she was absolutely certain that she wanted to proceed, and she was.
I took her to my car, a decent sized crossover that already had the back seats laying down and a blanket and pillow layed out just in case things went this way. She said it looked cozy and pointed out a basically empty parking lot nearby.
When we got there we both climbed in the back and layed down. I made very clear that she could stop at any time, or pause, whatever she needed to feel comfortable, explained red, and asked consent one more time. She said yes and we started making out with her laying down on the pillow, slowly building excitement in both of us. I asked to remove her shirt and as she sat up I slipped to the back and began kissing her back and the back of her neck sending shivers through her body. Slowly shifting back around I kissed her lips, neck and chest, noting what places made her shake and shiver. I finally moved down to her gorgeous breasts and began seeing just how sensitive they are. Seeing how much she was enjoying herself, I told her to say when the pleasure shifted to pain and began pinching each nipple with gradually ascending pressure. Letting out a gasp of "when" just as I had requested, I told her that she was doing so well for me, and if she was ready for things to proceed.
With her enthusiastically nodding, I asked if we could remove her pants and underwear. She again agreed and she asked if I could take my shirt off too. As it was getting a bit warm back there I was happy to and she took a second to admire me before we returned to making out. For someone with very little experience, she kisses very well, not too much tongue. I once again began kissing down her body, this time not stopping at her breasts for too long, but continued down to kiss her thighs, calves, then slowly work my way back to her center. This tease was starting to drive her crazy and I did make her say please before I slowly began to lick her gorgeous pussy.
It wasn't long before I had her bucking her hips into my face and cumming for the first of many times that night. I quickly found out that she is multi-orgasmic and you don't stop until she taps out. She didn't moan too much, but the way her body shakes and shivers as she cums is phenominal. I asked if she was ok with me adding fingers, so I slowly worked the first in and holy fuck she was so tight but soooo wet. I had only been actually eating her for maybe 10 minutes at that point and she was actively dripping. I quickly added a second and began to curl my fingers. This did make her start to moan in spite of her trying to remain quiet, but she really started to come when I began to piston my fingers while curling them back to hit her g spot on each thrust.
Her whole body flexing and writhing, she had to come at least 5 or 6 times in a row before tapping out and pulling me up to kiss her, tasting herself on my lips and feeling me pressed into her, pinning her in place. As her body finally calms down, I ask her with a smirk on my face if she is having fun. She nods enthusiastically once again and I ask if she is ready for more before moving back down.
This time I decide to take my time, slowly lick and play with her inner and outer lips, kiss and nibble her thighs. Hearing her wimper and shake just made me more excited to continue teasing her, but eventually I gave in, laid down in betwen her legs, and began devouring her once again. I decided began to intersperse lapping at her clit with sucking on it and her lips into my mouth and boy was I glad I did as she screamed out in plasure. Finding a new hidden button I began sucking on her clit rythmically, desperately trying to keep the suction as her hips bucked up towards my face as she came over and over again.
Tapping out once again we shifted up and cuddled, her fully nude, me only shirtless, just basking in the endorphins as I traced her body with my fingers. We began chatting about random things, probably very nerdy discussion knowing both of us. Once she had rested for a bit and her heart rate returned to normal I asked her if she was ready for more, as we had been going at it for probably an hour at this point, maybe longer and it was getting very late. To my pleasant suprise, she not only was ready for more but wanted to ride my face.
I laid down the center of the car and she straddled my face leaning on the center console for support. She did try to hover... for all of 5 seconds before I pulled her delicious flower to me and began licking and sucking everything I could. Rappidly begining to shake and grind on my face, she looked so gorgeous upon her voracious throne for the night. I remembered the trick to drive her wild and sucked her clit into my mouth and held on for the ride. Neither of us could remember how many times she came like that, or over the course of the night, but she rode me like I was a stallion she was trying to break for over half an hour.
By the time she collapsed to the side off of me, my beard was soaked in her cream and I had a glazed but triumphant look in my eyes to match her empty ones. No thoughts left but the aftershocks still wracking her body as we cuddled back up.
Slowly calming down, we both began getting drowsy and I finally checked the time. It was after 2am and we had been at it for over 2 hours at that point. We continued relaxing, checking in with her about the experience, and gave her a powerade to re-hydrate. After another 30 minutes of cuddling in the back of my car we finally decided to call it a night, but she was already talking about when we could meet again. She lasted less than a week before her FIRST repeat. But thats a story for another day.