Episode 3: Cindy

Cindy was a cute short white hooker that I had multiple encounters with over the years, the first time around 1996 and the last time around 2003. She was in her 20s when I met her for the first time.

It had been about two months since I broke up with my first long term girlfriend of three years. While I was relieved from the toxic relationship, I had started to miss female companionship. I needed the female touch.

It’s was a very cold night in the dead of winter, I had just got off work delivering chicken and I kept thinking about being with a woman and thinking that I should get me a new girlfriend.

As I drove home at three am, I saw this long haired blonde woman walking the sidewalk slowly and I slowed down next to her after going around the block once checking for cops.

As I stopped, she turned and looked in my window. I rolled it down and she stuck her head in the car. My god she had a cute face.

She tried to start talking, but I interrupted her, “Just get in.”

She got in and was wearing jeans over the multiple layers needed in our northerly winter weather.

She had big tits, cute round face and long blonde hair that reached her ass. She was hot.

The usual questions about being cops were exchanged and she said her name was Cindy.

“So Bob, what are you looking for tonight?”

“Depends.” I said as I drove around in the looping streets of the neighborhood. She was good looking so I expected her to ask for a high price.

“Depends on what?”

“Come on Cindy, you know. Depends on the price of course.”

“Of course.”

“How much for head?”

“$20.”

Twenty was cheap.

“How much for a lay.”

“No lay. I don’t have a condom and I don’t fuck without a condom on.”

Huh, so condom-less head for only a $20, that was a very good deal.

“Ok then, a blow it is.”

Cindy directed me to a dark spot right on the street under a burnt out street light. It wasn’t even 50 meters from where I picked her up.

I paid her and pulled down my pants.

She was very good and enthusiastic. She made me cum in less than five minutes and actually swallowed!

I pulled my pants up and expected her to exit the car but she just sat tight and started some inane small talk.

After chit-chatting for nearly five minutes I was bored and tired and wanted to go home to sleep.

“So, Cindy, we’re done. Aren’t you getting out?”

“It’s cold out. I would rather stay in a warm car.”

“So that’s why you’re chatting with me.”

“Well, yeah, but also you’re very cute. I’ve never had customer this cute before.”

“I’m flattered, but I’m tired and need to go home to sleep.”

“Can you drop me at my place on your way, if it’s not too much trouble?”

“Depends. Where?”

Her place was a street over from mine. So I drove her home and took a detour to my apartment. I don’t know why, but somehow I didn’t want these working girls to know where I lived.

The second encounter with Cindy was a bit upsetting. It was a couple of months later.

She did the same with the bareback blowjob, but as I was about to shoot the first shot, she pulled it out of her mouth and it was aimed back and the first squirt landed on my fucking face. Jeazus!

I quickly pushed her head by force back towards my cock and the second squirt got her in the face, so she put my cock back in her mouth to avoid a full on facial and swallowed the rest.

The third time was about a year after the second and it was around June. So it was warm.

I had condoms with me so I went for a lay with her.

As I drove around looking for a spot, many of the usual ones were full of cars, so I headed towards the cemetery’s edge where it was quiet and quite dark.

After paying Cindy, I took off my pants and underwear while she pushed the passenger side seat down to a fully down position and lay back and pulled off her signature jeans, then panties, jacket, t-shirt and bra. Cindy got fully naked in my car!

“What are you doing? You’re completely naked.”

“Thank you captain obvious.” She quipped.

“Why?”

“Sometime I like to be fully naked. It feels better with special customers.”

I found it weird, but what the hell, she had very big firm tits and looked extremely cuddly on my car’s seat.

I moved in front of the passenger seat as Cindy pulled back her chubby legs and spread wide, then scooted down so that her butt was at the edge of the seat offering her shaved pussy to my use.

I pushed my sheathed cock into her surprisingly tight pussy to find it very wet and slippery, in two strokes I felt my cock head against her cervix. Nice.

I fucked her for what seemed like a long time. Every time I sped up aiming to cum, she would do something to slow me down, which made me look at her closely and I found her making an almost-there-with-orgasm face.

“Fuck me, fuck me,” she chanted few minutes later, and she pulled me down to press my body against hers hard, as sweat poured off me and her down onto the car’s seat.

“Yes, yes, yes...” She squealed as her pussy clamped really hard and twitched on my cock. I shot a big pent up load inside the condom, grinding my pubic bone hard against hers, and collapsed onto her comfy body.

She kept her hands around my back keeping me on top of her, with her heels hooked under my ass keeping me inside her. I was tired enough that I tolerated the sweaty heat as I caught my breath.

Finally I pulled away and out of her embrace as my cock softened, and stood on my knees on the floor of the car between Cindy’s legs.

“Oh Bob, that was so nice. It’s been a long time since somebody made me cum by fucking me long enough.” She exclaimed.

“It was nice. I enjoyed myself too.” I answered her as I pulled off the condom and tied it.

It was the first time a hooker orgasmed with me. I liked it as it boosted my ego a lot.

Being a delivery driver I always had a paper towels roll in the car and we put it to good use wiping all the sweat the covered both our bodies. Good thing the car seats were vinyl, as they needed a good wipe down too.