F(25) First Time I Slept with an Older Man(55) (throwback)

When I was 18, and a struggling college student, I was so desperate for a promotion. My boss was a handsome, mid 50’s guy- who had it all. The dream company, homes, cars, women- all of it. I was the nerdy intern working the desk in the warehouse- but I knew he respected me and provided me with my first big opportunity, and I felt as though I would always owe him for that.

I was working late one night, and had to get ready to go out with my friends while still at work. Aside from a few shop guys, everyone else was gone, so I felt comfortable sneaking off into the back room and sliding into some barely there micro dress and some unnecessarily high heels (the obvious choice for trying to look older and get past club bouncers). Just as I was about to leave, the main desk phone rings… and in my new and in no way work appropriate outfit – I had to walk past those last remaining shop guys to answer it.

Their jaws probably stayed on that cold concrete floor til the next morning.

It was my boss- drunk, and needing a ride from the restaurant he had a client dinner at to meet one of his girlfriends – and he offered to pay me $100 to come get him.

“Oh, and bring my other Range, not that ugly truck of yours” he requested… I may have felt somewhat slighted by the comment, but I felt like a bad b!tch walking down the halls, hips swaying, long legs on full display into his office to snatch those keys and take his SUV to go and get him.

As I left the building, I heard a cat call and a whistle, and let the door slam.

I rolled up to the restaurant and of course- he’s at the bar. Not ready to go. My phone was blowing up, my friends are no longer waiting for me- so I’m on my own. Pissed- yes, but excited to snag that extra cash and roll around town in his car for the night.

As I walked up to the bar to collect him, his client and him first saw the nude platform pumps, then the long tanned legs leading to my wide hips, a black garment barely holding on to the curve under my ass, narrowing at my waist before finally seeing long blonde hair and my pouty dark red lips, with dark eyes glaring back at him.

I felt as though they stripped me with their eyes and could see what every inch of my naked body looked like under that dress. I saw his glazed expression come into focus as he realized exactly who was addressing him…

“Well- you ready or what?” I was indignant.

“Did you have other plans?” He shot back. “I’m sorry, I didn’t know you to be the type with other plans- you’re always buried in a book”

“You only see that side of me, but yea, I was planning on going out.” I retorted. In my mind, I’m just begging him to pull his sh!t together and let me drop him off, get paid, and go out… but suddenly a part of me wanted to know more of what he thought he knew about me…

“Well girl, let’s go out then- where did you plan to try to get in?” I was shocked- what would my friends think? I didn’t give him the real place- instead I decided to challenge him more- and picked the most exclusive club this college town had to offer- the Mint. He sent a quick text, finished his whiskey double, and grabbed my hand.

My body flushed red and I matched his long stride out of the restaurant’s bar. His client watched my ass cheek creep out from under this skimpy black dress as I sauntered away.

Safe to say- he became a repeat client, and always came to see me in the years moving forward.

As I pulled in front of the club, a valet met me in the street and took over- I had never had valet parking before, and I was used to dropping a friend and parking for free in the park ten blocks down and walking- praying the line had moved up in the meantime. My boss tipped him with a $100 right then- and a part of me was jealous that this valet and I made the same convenience wage.

I stopped to dig for my fake Hawaiian ID but to my surprise the velvet ropes opened and we were immediately let in… no ID necessary.

We were taken to a booth overlooking the dance floor- the second floor was somewhere I didn’t even realize college students could go to. Looking around I saw other high profile and high powered businessmen with beautiful model like women gathered around, or draping long legs across their laps.

My boss didn’t ask me what I wanted, ordered me a whiskey double- the same as him- and sat down. I stood there- still in shock like a deer in the headlights of an oncoming big rig.

I felt his hand caress the inside of my thigh and tighten his grip to pull me down. I sat next to him – and slowly lifted my glass to my lips, when he said “I know you’ve never been up here before- what do you think?”

Before I could give him a good answer, I felt his fingers plunge into my slick folds- and saw the realization cross his face as he discovered i wasn’t wearing panties. I panicked, as any naive 18 year old would- and blurted out “what about your girlfriend?”

Immediately I was kicking myself- I honestly couldn’t give a single f•ck about her in that moment. I realized my boss had noticed I was way more than some bookish nerd who kept things running smoothly- and he was very clearly and quite literally- into me. Knuckles deep actually, and petting my insides. I was soaked already.

I hated that I was willing to be *that girl* who fucked her boss to maybe have a shot at a higher paid gig- but I was also giving in to my slutty side. I dressed like this wanting to get fucked. I was going out tonight with this in mind anyway- and from whom? Some douchebag frat kid named Kyle or Chad who would dump his load in me after two minutes and never call me back?

This was a way better offer. So I leaned in.

And so did he. I felt his bulge harden through his slacks as I slid my bare pussy onto his lap and started to run my fingers through his salt and pepper hair. He had broad, strong shoulders, the slightest curls poking out from under his dress shirt, and his big hands gripped my thick ass.

“What girlfriend? Just another girl who wants me to f•ck her for some red bottom shoes or a nice bag she will spill her makeup in? No, I’m good right here”

I started to make out with him, whiskers scratching my face, grinding my pussy against his bulge. The dance floor was going crazy, the music was so loud, and I genuinely thought I could get away with unzipping his pants and fucking him right there….

Until he pushed me off of his lap, and told me to go down and dance with my friends. That is why I was here, right?

I was hesitant, given I told him the wrong club, but I didn’t want to lose his interest so I went. The whiskey had really started to hit me and I was tipsy- 18 year old girls can be like that. While bouncing and shaking my ass, I felt two strong hands grip my hips and start grinding into me- and I was sure it was him. So I started doing my best to grind on him back- including reaching back and massaging his bulge…

Weird though- I could have sworn he had slacks on, but I was feeling denim. I didn’t question it- as I guided his hands to my tits and reached around to pull his face in for another kiss…

I noticed that his skin was smoother than I recalled from just a few minutes ago- and when I opened my eyes, I saw my boss grinning from the upper deck- winking at me. I pulled away- and saw some frat guy wearing his stupid polo shirt and left his grasp immediately.

I went to leave- embarrassed that I fucked up what was maybe my only shot, potentially just lost my job, just bruised his ego- but was met by my boss at the foot of the stairs.

“That was hot as hell girl- you’re a real slut when you aren’t at work, aren’t you?” I looked down, and sheepishly nodded, admitting that the glasses wearing workhorse he knew- wasn’t the real me.

“I f•cking knew it” he chimed in. “Let’s call a cab, there’s some things I’d like to see”

On the cab ride to his house, I had started to sober up again- knowing I needed to make a big rebound. I knew he wanted to f•ck me- there was no doubting it now- but I wanted to shock him even more.

We walked up his long red brick driveway, in under his marble arches and onto an exquisite tiled floor- and I kicked out of my heels so as not to fall. He towered over me now- the power dynamic between the two of us remained. As he walked off to the kitchen to fix us a snack and another round, he directed me toward the restroom- almost like he knew my next move.

I walked in, freshened myself up- and slipped out of that black dress, and silently padded my way into his kitchen, before quietly hopping up onto the counter behind where he stood at the microwave. As he turned with two beers and a plate of mozzarella sticks – he was clearly shocked to see my now naked but extremely perky 18 year old body behind him.

I couldn’t even the get words out before that plate was set down next to me and his lips locked onto my neck, with that cold beer bottle pressed against my nips.

My body shuttered in surprise and I let out an unexpected moan- as he dragged his lips to my now erect nipple and locked on. I took a drink and let my head relax as I gave in to the feelings of his knowing mouth massaging my tits. His fingers teased the opening of my slit and my clit, flicking across with the added wetness of the cold condensation from the bottle itself. I melted.

As I lay back against the counter top, his lips moved to my lower lips and his tongue darted in and out of me, before locking onto my clit as a single finger began to fuck me. My body began to get hot with wanting and I absentmindedly grinded into his touch. Another finger penetrated my wet cunt and I started to cry out for even more. A third finger probed, and then a fourth- and he realized I was more experienced than he ever could have expected.

I was already on the verge of cumming when I heard him pour out what was left of his beer and I felt the cold opening of the bottle enter me. I couldn’t take it anymore and reached down and started to fuck myself with it. He leaned back against the other counter top, eating a mozzarella stick, watching my every move.

I saw him slide his phone out of his pocket and start recording. I have a huge kink for being watched and recording while playing so I really turned up the heat on my moans. It wasn’t long before my orgasm rolled over me like a huge tidal wave and I squirted right there on his counter.

I didn’t have time to recover when he drove into me with his huge, pulsating cock. He gripped my wide hips and drove into me, and I couldn’t care less about the lack of condom as he plowed deeper into my 18 year old pussy. I watched in the reflection of the great kitchen window as my pale nude form contrasted with his nearly fully clothed form as his darker shaded cock fucked me against the marble counter. I wondered if anyone could see this semi taboo entanglement unfolding- and these thoughts overwhelmed me as I gave into my carnal desires and kinks and allowed another wild orgasm to take me over. I soaked his cock and the hem of his shirt, just as he unloaded into my depths- filling me to the brim.

Needless to say, he didn’t have many more disposable weekend girlfriends, and we relived that experience with regularity.

I also got my promotion, and several more in the years that followed.

I proved myself worthy in many, many ways.

Should I do a part 2?

Source: reddit.com/r/eroticliterature/comments/n54rc2/f25_first_time_i_slept_with_an_older_man55