Best Ride Share of My Life

It was a random Friday night. I was feeling a little frisky but didn’t have anything specific in mindA friend of mine works at a gay bar not too far from my house. Knowing my friend worked there I figured I could head over around midnight and see if there was something worth getting up to and if not I could chat with my friend and catch a ride home. So I called a ride share and tossed on some jeans, t-shirt, jacket and backwards baseball cap and headed out of the door.
As I climbed into the back seat to my pleasant surprise my driver was a gorgeous trans woman. She had long black hair and her make up was done in a way that said I am here to work but her smile said “I wanted more”, the sun reflecting off of her red lips creating a beautiful orange outline.
We proceeded to chat away the whole way to the bar. We had similar interests and I said we should hang out sometime as we arrived at my location. She said “are you asking me for my number?” and I being such an idiot I should have asked her said “yes”
Numbers were exchanged and I walked into the bar with a glow with already having a good start to the night.
The evening did not amount to much. Remembering that lets call her Rachael (the gorgeous trans rideshare driver) mentioned she worked late, I figured I would shoot her a text. To my excitement she responded. After a few texts back and forth I invited her over. She showed up to my door wearing a nice little short black dress to match her sexy black hair with a nice tight top. I welcomed her in and got her a drink and we moved to the basement where there is a lounge area and then another bedroom.
We got situated on the couch and started chatting and sipping drinks as I rubbed my hand over her arm and she responded by rubbing her hand up my thigh. I then placed my drink down and slowly leaned in and asked if I could kiss her neck, she said “have your way with me, I like it all”. Upon agreeing on boundaries and such I slowly kissed her neck and then began moving my way from her neck to her ear with my tongue and from her ear to her mouth.

2024-01-16 by baldbeardbottom 5,308 Views

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