Watching a Couple [MF] in the back seat of [M]y Uber

I started driving Uber last fall when my business hit it’s slow season. I typically only drive during the day as I have zero desire to deal with drunk people. There have been a few, but I can count them on one hand. During the holidays last year there were a few days where I worked into the evening.

One of these evenings I picked up a couple from a downtown restaurant after a work related holiday party. Both appeared to be in their late 20’s/early 30’s, white, average appearance. He was pretty well lit, but she seemed only a little tipsy with a case of the giggles.

When they got in the car, he leaned forward and loudly asked “Hey driver, got any weed?”

“Can’t say that I do”

“It would’ve been cool if you did!”

Alright then, it’s going to be one of THOSE rides.

[M]y birthday present from a [F]light attendant

Since Covid has effectively killed my food business, I’ve been driving Uber for extra cash. Birthdays stopped having a lot of importance a while ago, so driving on such an auspicious day as my 50th birthday didn’t bother me. 

Around noon I pinged for a ride at an older Holiday Inn that’s downtown right on the lake. My passenger’s name was Claire. I wondered what she was up to in the middle of the day. 

When I pulled up, I could see a woman wearing something kind of tropical with her phone in her hand. This is usually a good sign that that’s who I’m looking for. Her dress was green with a tropical floral print. Below the waist it looked like a wrap while baring her midriff, and wrapped her boobs almost like a bikini top. Plenty of cleavage. Her black hair was cropped at her shoulders in a cute, professional Mom cut. She was wearing a mask, so I couldn’t see her full face but didn’t mind the view so far! 

She got in the car, and we immediately started chatting on the way to her destination. Turns out she was a flight attendant, and had just checked into the hotel for a layover until 6am the next morning.

Adventures with Grace: The Day She Got Two Cocks [MFM] (long w/ a pic)

After [our first threesome](https://www.reddit.com/r/gonewildstories/comments/iadyz4/adventures_with_grace_our_first_mff_long/), Covid started becoming serious. It was only a few months ago at this point, so you probably remember how life changed drastically in mid March for most of the US outside of NY.

Grace and I weren’t an exception, the weekly routine of 3-4 dates per week we had enjoyed came to a crashing halt. We started squeezing in quick lunch dates here and there where our schedules allowed.

As horny as we were, we started having car sex. I never thought I’d be 49 years old, and regularly getting it on in the back seat like I was in high school. Surprisingly, it was a lot of fun! Granted, I was still having sex with my girl, but the car brought a new, unexpected dynamic. I think it was a combination of the uncertainty of the time, the possibility of getting caught (we were usually in a deserted parking garage in the middle of the day), the chemistry we had with each other, and just being super horny whenever we were in the other’s presence. It was definitely a memorable few weeks.

Adventures with Grace: our first [MFF] (long)

I was seeing Grace for a few months in the spring. We met in February with an instant attraction that was undeniable. At 22 she wasn’t my normal type, I’d describe her as tall (5’10”), willowy, long brunette hair, dazzling smile, amazing blue eyes that suck you in if you stare into them. Her chest was on the smaller size, but her ass made up for it. Round, firm, solid from years of swimming in high school, gorgeous. I still dream about her ass. Objectively speaking, she’d easily be a 7 out of 10.. Maybe an 8 if you’re into women like her…. Personally, I thought she was off the charts gorgeous. I look at her pictures now and wonder how such an amazing, smart, funny, brilliant, and beautiful woman was into me. I learned a long time ago not to ask too many questions, and just go with it. ;-)  

Me? I’m 49, tall, heavy where I used to be athletic, more gray in my beard than I like to see, a thinning bald spot in the back that seems a little larger every time I look. I’m the funny Dad next door type.  

The One Where I [M] Fucked A College [F]reshman

I started chatting with Alison last September (2019). She’s a cute, short, asian, 18yo (at the time) freshman at a local university. She started messaging me, and while I typically don’t go for 18 year olds (I’m 49, father of 4… all teens) I will flirt with anyone. That’s all it was during September, into October, the occasional flirty text here & there.

In late October that changed. This is that story.

She started texting me early one Saturday morning wanting to hook up. There was a tonal change in her messaging, I could tell she was serious about meeting. Alison said her roommate was out of town, leaving her the apartment. She was at a friend’s place but was heading home. She quickly shifted to a direct sexual conversation. Being so young, there were still a lot of things she hadn’t experienced. She’d only been with 4-5 guys at this point, and I would be the oldest. She said she wanted me to cum in her mouth and in her pussy, since she hadn’t had anyone do either before. I knew from previous conversations that no one had ever gone down on her. There were three things we could easily knock off her to-do list!

Whisper

This was a short, creative exercise this morning.

—————————————————————————————————

I lean into your ear, inhaling your perfume. I’m instantly transported to the first time we were together, the first time I smelled it.

I walked into the apartment where you were waiting. Wearing nothing but a t-shirt that barely covered your ass, you looked at me anxiously as I entered. There was uncertainty in your eyes, a little nervousness. You bit your lower lip while looking for reassurance in my eyes.

I locked the door, and confidently walked over to you. I slipped my arm around your waist, pulling you in close. This was the first time I’d set eyes upon the woman I’d been texting with for a few weeks. You delivered on the promise of your verse and exceeded my expectations. You were finally in my presence, in my arms. The world outside that small apartment ceased to exist, there was only you and I.

I looked into your blue eyes, swimming in them in my mind for a heartbeat that seemed to never end. Having you close felt right, all the thoughts & desires coming to the surface. All the hesitancy & nerves succumbing to the moment.