Joyriding with my Executive Assistant’s Daughter [MF] [M]

Spice starts after the *

As mentioned previously, I once worked for a big bank and was awarded several promotions pretty quickly. Prior to leaving the bank I was running a big department and one of the perks of this position was my very own Executive Assistant who helped me schedule my calendar, manage my time and travel, and screen out the weirdos. As described earlier, she was old enough to be my mother, probably in her early 60s and her name was Donna. She was tiny and Portuguese with short dark hair, a twinkle in her eye and a big laugh. And she was incredibly effective.

It was Donna who witnessed Tina stumbling disheveled out of my office in the aftermath of her wild mid-afternoon orgasm (Mentoring the Nerd). I felt that Donna’s jaw dropping disbelief ruined her impression of me that day.

I assumed incorrectly.

A couple months after the Tina episode, Donna set up a one-on-one meeting with me in my office. Considering that we basically worked hand-in-hand all day, this was highly unusual. I suspected that Donna was going to resign or retire.

Instead, she wanted to have a serious discussion about her daughter Francesca. I didn’t even bother to know that Donna had a family, so it was a bit of a shock that she wanted to talk to me about her kid.

“647Stealth, my daughter Francesca quit university and moved back home. She is depressed and lonely because she misses all of her friends. I don’t want to be too forward or out of line, but I’m wondering if you would…maybe…and if you say no I’ll understand…invite her out to dinner? Just to get her out of the house. I’ll pay!”

STILL shocked.

Donna’s eyes were pleading. This was a very serious matter to her. She was so good at her job that I couldn’t say no and simply agreed immediately.

“Thank you soooooo much, I will arrange everything!” And she sprinted out of my office delighted.

Within a couple of hours my calendar was updated for 7PM on Friday night at a very hipster eatery in the downtown core. “Dinner with Francesca”.

I got there a few minutes ahead of 7PM and took a seat at the table. The place was packed full of lumberjack shirts and designer jeans.

Soon the restaurant hushed momentarily. A young 5’4” brunette with teased out shoulder-length hair strode into the restaurant wearing a shimmering black and silver lacey mini-dress and four-inch heels. The dress was nearly transparent and so tight and short that she had to hold the hem against her thigh as she walked so that it wouldn’t run up and reveal her crotch. Even from across the room, her black thong was clearly visible underneath the dress. She had a large set of breasts that were pushed together and lifted up by the dress and…listen I have no idea what her cup size was…all I know is that they entered the room first. Not only that, she also sported a perfectly flat stomach and a large curvy derriere. Honestly, she was almost like a cartoon character – like Jessica Rabbit or Betty Boop personified.

And she walked straight to my table. Assuming this was Francesca, she was exactly the opposite of what I was expecting based on my Executive Assistant’s overall size and proportions and the emotional state that she was supposed to be in based on her mother’s concerns. She looked more like a stripper.

As she closed in on me from across the room, I stood to greet her. Francesca came in for a big hug, smashing her large breasts into me, and kissing me…on the lips (WTF?). She let out a little moan.

“Hi, I’m Francesca and my mom has told me a lot about you” She winked. “and so far…you exceed my expectations.”

The evening was immediately heading in completely different direction than I could ever have anticipated.

Francesca ordered a martini and downed it in about 10 minutes while we were going through the basic introductions. After some appetizers and during her third martini Francesca leaned in close to me with a glint in her eyes and proposed that we go for a ride down to a local beach. Now, its like November so its chilly and the sun had already set so I had no idea where this was going. But there was no way I would say no.

Just before I settled up the bill, she leaned over, parking her tits on the table top, and whispered into my ear.

“I’m really strong, ya know” She smiled lasciviously at me. “ let’s arm wrestle. If you win, I blow you, if I win, you eat me.”

I’m not sure what the expression was on my face, but I tried to hide my shock while I placed my elbow on the table.

“yer on!”

As a gentlemen, I made sure that my arm was a noodle and she won easily. After her surprise victory Francesca captured my gaze and moaned with appreciation.

“Next round.” I had an idea. “If I win, you go to the bathroom and remove your thong for me.”

*

Francesca giggled, knowing that she would soon be commando under her shimmering little dress.

When Francesca returned from the bathroom, I noted that it was good that she was perfectly shaved because otherwise, her bush would have been on full display through that ridiculous transparent dress. As we prepared to leave, Francesca leaned into me for a deep kiss exploring my mouth with her tongue and surreptitiously sticking her sticky thong into the inside pocket of my jacket. No doubt that Francesca could feel my penis hardening against her hip as I squeezed her big, toned ass. This girl did a lot of squats. Our PDA was completely inappropriate for that restaurant and a couple patrons gave us disapproving looks as we exited.

On the walk to the get my car in the parking garage, the sexual anticipation was ridiculous. She pulled me into the doorway of an old building and kissed me hard, driving her body against mine, grinding and moaning into my mouth as or tongues intermingled. Francesca grabbed my hand and slid it up and down against her wet slit. Then she moved my sticky fingers to my mouth and fed them to me. I complimented her on how sweet she tasted as I licked them clean.

“I can’t wait to collect on my win”

She didn’t wait long.

My car was on the second floor of the parking garage overlooking the street. Before I could close my door, Francesca was already in her seat leaning back against the passenger side door with her dress hiked up to her waist, her knees pulled up high with her bald pink slit dripping in front of me.

“Eat me!” she demanded right there in the front seat of my car under the florescent parking garage lights.

I complied with enthusiasm. It took some maneuvering around my stick shift and console to comfortably get into a good cunnilingus position.

First, I teased her by running my tongue in large circles around her vulva from her asshole all the way up and around her labia and clit that was beginning to protrude from between her lips. Francesca squirmed as I began to squeeze her vulva between my fingers and lick millimeters above her clit. Then I ran my finger lightly up and down her slit, her juices sticking to my fingers. Francesca was groaning loudly and pumping her hips against my fingers. I flicked my tongue against her clit which elicited a sharp gasp.

Then I finally ran my tongue up and down her labia and used it to scoop her honey that was pooling at her entrance. I didn’t notice when Francesca had wiggled her tits out of the dress, but she was twisting her nipples that topped her huge globes. Actually, her tits were really unique because her nipples were the same color as her flesh. I could not tell where her areolas started or ended. Ghost nipples! Francesca knew exactly where they were as she twisted them hard while I was licking her labia.

By her moans. her rotating hips, and the liquids pouring out of her I knew she was already close to orgasming, and I had only touched her clit once with my tongue. I inserted two fingers into her vagina and swiped my tongue with as heavy pressure as I could muster across her little pink nub in back and forth motions. Francesca moaned loudly as I did this and within only a couple of minutes, orgasmed against my mouth. Her opening swelled and her little clit throbbed against my tongue.

So, there was my EA’s twenty-two year old daughter, who slumped against my passenger side door with her big tits hanging over the top of her dress and her swollen vulva glistening under the florescent parking garage lights, heaving in the afterglow of her orgasm.

Soon, Francesca popped her big breasts back into her dress, turned forward and put on her seatbelt. She didn’t bother lowering her dress and it was still hiked up to her waist.

“Let’s hit the beach!”.

During the 15 minute or so drive to the beach, Francesca teased me by rubbing my stiffened dick over my pants. I was afraid the precum was going to leave a stain. To add to the tease, periodically she would reach between her legs and scoop up her fluids and feed them to me as I drove. It was excruciating.

We arrived and parked in the nearly empty lot that ran for almost a kilometer along the beach. There were maybe three or four other cars. Luckily, this was perfect condition for Francesca’s plan.

“I always wanted to fuck on a beach!” Francesca was already getting out of my car, dress still hiked to her waist. “You coming?”

She skipped through the bushes and disappeared towards the sand. Despite the chilly night, my dick led me to her. Francesca had removed her high-heel pumps and was spinning and dancing in the sand naked below the waist. Her white skin sometimes glowed in the faint light of distant streetlights as she twirled.

Notwithstanding her momentary display of joy, it was damned cold, and soon she was shivering. I placed my jacket over her shoulders to warm her. She leaned up and kissed me grabbing my now softening cock through my jeans.

“I’m not fucking you on this cold sand.” Despite my initial eagerness, I knew the logistical limitations.

“I have an idea!” Francesca grabbed my hand and led me back to the top of the beach where there were bushes and a few small sapling trees. She pushed me against a sapling, squatted in front of me, and tore my pants and boxers down to my knees. Within a few seconds, the combination of her hands and tongue had me hard again, despite the uncomfortable breeze. Francesca was really good. She would fondle my balls, lick up and down my entire shaft, and then pop the head of my penis into her mouth and swirl her tongue around it. Then she would swallow it and tease me with her lips and throat. This went on for a few minutes, and I forgot that we were actually on a public beach.

She was bringing me close, but I had a duty to fuck her “on the beach”, so I pulled her up to me.

“You ready?”

Francesca moaned, wrapped her hands around the sapling, bent at the hips and lifted her big ass to expose her pussy to me. Even in the semi-darkness, her pussy was slick and puffy between her slightly spread legs. Without her pumps on, the angles were a little challenging a first but we worked it out and I pushed into her.

I guess it was because we were outside and apparently alone, Francesca felt comfortable being really vocal.

“OOOOOOOHHHHH…YESS!!” and she continued to moan dramatically as I stroked into her. Soon Francesca’s back arched, her mouth was slack and her moans were interspersed with grunts and the odd squeak. I was pounding her in a way that made little ripples in her ass as I stroked into her. I wondered how she would feel if I grabbed a ball of her hair. Her response was glorious.

“OH…FUCK…YESSSSS!”

One of her big tits had fallen out of the top of her dress, so I also squeezed it and pinched her ghost nipple as best I could. Francesca’s knees buckled as she came. I had to quickly change positions to grab her around her hips to protect her from falling.

“You ok?” I was holding her up as she shivered.

“Oooh….fuck……….oh yeah.” Giggling, she turned and hugged me around the waist. My hard wet cock mashed in between us, staining her dress, my jacket and shirt. After I got my pants up, we walked hand-in-hand back to the car.

As I was getting into my side of the car, Francesca waited momentarily and then jumped in straddling me and kissing along my neckline. It sent shivers throughout my body. We struggled monetarily to move the seat back far enough and low enough to make room. It took a couple more minutes to get my pants out of the way, but once we were settled, Francesca went to work. She found a way to massage my dick by sliding her wet pussy up and down my shaft, making me hard again. She popped her giant tits out of her dress again and fed her nipples to me, which I sucked and nibbled on gleefully. Francesca moaned.

After a few minutes Francesca reached down and inserted my cock back into her vagina and lowered on it until she fully engulfed me. We sat like this for while as Francesca savored the pleasures from my mouth and cock.

Then she went to town.

Francesca started to ride me hard in long deep strokes. It wasn’t obvious to us at the time, but the car was bouncing along with her hips as she yelped and groaned above me. I held on as best I could by her hips and ass.

It was then that I noticed in my peripheral, someone standing near the front fender of my car. Although I was startled, Francesca’s aggressiveness made it hard for me to react. I looked around her shoulder and made eye contact will a tall skinny dude, probably in his fifties, with his running shorts around his thighs and his skinny dick in his hand, jerking away.

Illuminated by the dashboard light and nearby streetlights, he was watching Francesca’s pussy engulfing my cock and her big, beautiful butt bouncing to the rhythm of her thrusts. I’m certain that he could also faintly hear Francesca moaning and grunting with pleasure. She was getting close again, but I was still a bit further away, mostly because the guy jacking off in front of my car was a pretty big distraction.

I quickly ascertained that the guy was probably out for a run and came across our bouncing car in the parking lot and decided to investigate. Although creepy, he seemed harmless as he stroked his skinny dick.

Rolling with it, I decided to give him a bit of a show. I pulled Francesca’s ass cheeks apart, revealing more of her dripping opening gripping my cock and also her pink puckered asshole.

The dude immediately pushed his hips forward and shot a thick stream of semen that arched almost to his shoulders and splashed a few feet in front of him. Instantly afterwards, he pulled his shorts up and disappeared through the bushes in front of us. If Francesca knew we had an audience, she never let on, and I held that secret till now (Thanks Reddit!).

When I stretched her ass out, Francesca moaned “OOOH…YES!!” encouraging me to keep her cheeks spread apart as I took over and began to thrust into her from below. Within only a few strokes, I felt the weirdest feeling of warm mist on my balls and inner thighs. And then Francesca exclaimed “OH…FUCK!” before beginning to convulse and whimper above me.

“What WAS that?” My balls were drenched.

“I just squirted, silly.” She was gazing down at me like I had three heads. “My god, that was a great one.” She was referring to her orgasm. “Did you cum?”

“Ahhh…no but that’s ok, it was great.”

Francesca was visibly frustrated and promised to get me off before we got back to her car.

When we untangled, it was clear that she sprayed all over me, my pants, my steering wheel, and half of my driver side seat. Francesca was helpful by licking up her sticky cum from my balls and inner thigh, which was nice, but my cloth seat was deeply stained.

The night ended with Francesca giving dutiful road head. She worked my shaft with her tongue and lips and hands. It was a mess down there between her drooling on my cock and her cum all over my front seat, thing were pretty slick. Maybe it was a bit of latent frustration, but as I got closer to finishing I was a little less considerate and at one point was fucking her mouth from below while holding her head in place by her hair. This cause me to drive erratically, so I had to pullover and park on a side street. She remained dutiful despite the odd gag until I finally spurted down the back of her throat. We got back to her car and I could tell she was expecting an invite to my house. It never came. She gave me her number and tried to make me promise to hook up again. I was elusive.

I had my car detailed the next day.

On the following Monday morning, Donna breezed into my office smiling and as bubbly as I have ever seen her.

“Francesca thinks you’re amazing! Whatever you guys did together really meant the world to her!” If only Donna knew.

I wonder now how much Francesca shared of that evening?

I saw Francesca once more at my final bank Christmas Party about a month later. She was the “Plus-One” with her mother, who was clearly still trying to set her up with me. Francesca was just as inappropriately dressed that night wearing a too tight little black dress that rode up to sometimes reveal the underside of her impeccable ass. I brought another date to the party, but that didn’t stop Francesca from approaching me near the end of the night.

“I bet I’m better in bed than that little slut.” She was referring to my date with a sneer. Then she leaned in against me and slipped her damp red thong into my breast pocket.

“Call me whenever.”

I never called her. And my date ended up becoming a favorite FWB.

Source: reddit.com/r/gonewildstories/comments/yckkhh/joyriding_with_my_executive_assistants_daughter