If you know me, then you might know that I drive for a rideshare company in the Los Angeles area. As you might imagine, this line of work lends itself to an unusual story, every now and then. Recently I've received a few messages encouraging me to add to the Squirm File Collection and I thought it might be time to share a RideShare adventure.
This particular adventure happened on a crisp Autumn morning, a little before 6am, it was twilight - that enchanting time right before daybreak,, and my GPS was guiding me to pickup "Brandon" off of Sunset Blvd. in Hollywood. He was a good-looking young man - my guess is between 20 and 24 years old - tall and lanky, sandy blonde hair and a million dollar smile. This happened back when face masks were required for all rideshares in L.A. county due to Covid and Brandon didn't have one. He sheepishly stood outside my car, pleading with me to NOT cancel the ride as his phone was dying and he might not be able to get a new ride before it actually died. Not to mention that it was cold outside ... so of course I told him to hop in. He was quite grateful for both the warmth of the car and the iPhone charger I offered to him so he could charge his phone. As he settled in, we set off to his destination, about half an hour away in Encino. We started chatting and he proceeded to tell me that I had just picked him up from a crazy sex party and he had been there since 10pm the previous night. I didn't quite know how to respond and he sensed my hesitation - which then made him feel awkward and had him apologizing all over again! As he was apologizing, he tells me that he doesn't know why he's telling me all this, oh maybe it's because he's "as high as a kite", he says ... which leads to nervous reassurances that he is not a danger to me. At this point I just interrupt him and tell him it's fine, I dont feel threatened in any way and if I become uncomfortable with our conversation I will let him know. 

Alcohol, cannabis and cocaine were available in abundance at said party. Brandon was definitely feeling the effects as he shared that he was a tit guy and he got to see ALL sorts last night. He explained to me how he loved all kinds: big ones, small ones, flat ones - and the most wonderful thing about tits is how unique they are ... he went on and on about how amazing and varied they are - consider the size and the weight of the actual tit, not to mention the size, color and shape of both the areola and the nipple ... the way he spoke of all the different variations of a woman's breast - he spoke with such wonder and awe, I was quite mesmerized - until he jolted me right back to reality when he suddenly started talking about MY boobs and how he could tell how full and heavy they were and how he wondered what my nipples might look like. I told him that he was just high and that I was old and both time and gravity had taken their toll. He reminded me that he was a connoisseur of boobs and I should allow him to be the judge of that.  From where he was sitting, he only wanted to see more of them and if I might consider taking a break from driving; he had some energy that he wanted to expend. I told him that I already had another ride after his and so I couldn't. He then informed me that all of our naughty talk had him rock hard and fixated on my boobs. My response was probably a bit flirty when I said ... "Oh really?" He affirmed "Yes, really! Would you like to see?" I replied with a breathy "Maybe", to which Brandon proposed "if you show me under your bra, I'll let you feel how hard you make me." 

 (As a side note ... if you have read the Experiment Series ... this incident happened during the same time frame and so I was extra motivated to do something this bold so that I could report it back to the dom that was "training" me at the time. He was very much into public play and I knew this would tickle his fancy! So, yes ... you guessed it.)

Once we arrived at his destination, I didn't immediately end the ride, but I did pull my bra up and allowed my very ample breasts free from their confinement ... I twisted in my seat and raised the sweater I was wearing so Brandon got a full view of both my boobs in all their glory ... he reached out and gently cupped my left boob and rolled my nipple between his thumb and his forefinger. I gasped as I pulled my sweater down and moved just out of his reach. He muttered a quick "Thank you" and went to unbutton his pants. I leaned over to get a better look and there he was, in all his glory. Now mind you, I had not seen a real, live, actual cock other than my husband's in 38 years ... so I was not only staring but my mouth was wide open. Brandon was definitely very hard and his cock may have twitched a bit. I reached in, gently wrapped my fingers around him and took a firm grip, appreciating both his girth and the rigidity of his member ... I couldn't resist - I just had to stroke him. I watched as his eyes closed and he reveled in my touch. I knew I had to stop at that point. So I thanked Brandon for the fun ride and he thanked me for the hard on. We ended the ride and went our separate ways. He did leave me a 5 star rating and a very generous tip. 

 As for me, Brandon will always be a very fond memory and a very hot fantasy. Have you ever fantasized about your RideShare driver? Well, if you're ever in Los Angeles ...